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YY =~ - “ ns g cents — <= e ‘ sal ; > Maes a seen en Se Scots a ae . ok . ~ > perpeny eh Semen ‘ re iain ba Aan Aten to en Mee sae : . woekan ins oe . - at Soren cee ee S — So at ree eas emnenoo nts tonne Renita aa ocr no fea annem ho onl es oh ha Hints Moe to", Byes Poo He . = ban fame Sey oes LA Seto : So reactive coer earn epee NT oad eg mate eames omen ene aE ay ee eect eens eae Sars penttrn torent een nee ene anes oat Seentameone == en pe toe oly am emcee SE: — an oe So te ae eH i a nae eee en son om om! SESS SSE SSST SSS SS SESS SSeS So ag ee EE Se ee FRANKLIN INSTITUTE LIBRARY PHILADELPHIA Class.G.6./..2 Book LTE Accession.../.G..2.L Aa Given by... lg.1. A222. boBlildhA22 72 DIGEST OF PATENTS Relating to COAL-TAR DYES AND ALLIED COMPOUNDS United States patents issued prior to January 1, 1924 , Prepared DY, ’ s oo 2", go 2° an - - 5 > ” ) s © fee. “AIDA: ME GONLE 2 3 2 4c) 2. Special Agent, Bureau of the Census DEPARTMENT OF COMMERCE, BUREAU OF THE CENSUS, Washington, March 25, 1924. I hereby certify that, the following report is a true and complete transcript of the data gathered and compiled for use in “Digest of Patents Relating to Coal-Tar Dyes and Allied Compounds,”’ the original of which is in the files of the Bureau of the Census, U.S. Department of Commerce. W. M. STEUART, Director. Publication of the above-named report by The Chemical Publishing Company is hereby authorized. HERBERT HOOVER, Secretary of Commerce. EASTON, PENNSYLVANIA, U. S. A. THE CHEMICAL PUBLISHING COMPANY 1926 PREFACE DIGEST OF PATENTS RELATING TO COAL-TAR DYES AND ALLIED COMPOUNDS. This digest contains abstracts of patents issued prior to January I, 1924, arranged by chemical groups. The abstracts are thoroughly indexed according to name of patentee, name of assignee, color produced on fiber, and by intermediates em- ployed in the process of manufacture. A cross reference index giving corresponding numbers and names in the German work by Schulz (“Farbstofftabellen,” 1914) is included. The digest was begun in December, 1917, in the Color Laboratory of the Bureau of Chemistry, U. S. Department of Agriculture, at the suggestion of one of the leading coal-tar dye manufacturers, work being continued at intervals for a little over a year until abstracts to date were finished. Later the work was resumed and the digest completed in the Bureau of the Census, Department of Commerce, the author being em- ployed by that Bureau in connection with the census of manu- factures as an expert on the subject of chemicals and allied industries. FE Eg Ace CONTENTS Page INTRODUCTION Outline of work). co 6 oe oa nade ole sw ee oa wan tise a IV Abbreviations 35.0006. 4605 <4}. 0 ou dale a yeecn a ee play ho ee V Chemical nomenclature . .. 4.5.4 005 neta pli ole okies oe V PATENT ABSTRACTS Coal-tar dyes: Group T—Acridin . 2.0.29. 00004002 0 I Group II.~Anilin. black 0... 00. dese sa sas 6 5 Group TT.—Anthraquinone- ... 025. 26. 92) ie. 8 Group 1V:—Auramin= «0.45% ss sine aes Sak pe ST ott 61 Group V.—Azin, including indulin ...... ..7 .a.aes ee 61 Group VI—AZ0 oi ed a ee alk aie ld. Hee oe 67 Group. VIlL—Indigo and indigoid ..:......... 32 eee 190 Group VIII.—Indophenol...3)%.5094.......445. eee 226 Group TX.~-Nitro oi. bee iei ee cue os cere «chee aay Group Se NIEFOSO uly ates oe eet PR ee 230 Group KU ——OXAZIN. oi css ce ele os 0's wre ip ae ane 231 Group: > All Pyrazolone {9.2 an oe so 6 Si dee etki alguna aa 240 Group XII]—Quinolin ~.... 0 202... e ess 243 Group’ XIV.—Stilbeme oc... 0c 56 yous bss ss ue 245 Group SV. piltur Soeur: Re Ae 247 Group . XVI—Thiazin 22. 6... 5 ose cs. oe ce ee 281 Group ‘XVIT.—Thiobenzenyl. 6. 0) a. ss oe os i 284 Group X VIII.—Triphenylmethane, etc. ..........2.. 0) =e ee 285 Group “XIX.—Xanthone (02.05 5.00.0. /s,0% 40 = bee 304 Allied Compounds: Group. XX.—Mineral dyes .........) i. 1. 3, 25 eee Pre or 311 Group XX1—Vegetable and petroleum dyes |... 2... 6se ee 314 Group XXIJII.—General processes and intermediates ................. 317 Group XXIII.—Applications, by dye groups and in general ........... 392 Group XXIV.—Finished products other than dyes ...........5....... 443 Explosives (€) 00. $0.2 sa0 2) 443 Flavors and perfumes (f) ¢.). .¢.00) eae 445 Medicinals (m) ..2..3....2: 545 5 ope 448 Photo chemicals (p) ... 2.24.40 ee heetOr Plastics (pl) 2... seed. A 470 Tannins (t) 0 o.....< cesses 2 oe see 476 INDEXES Assignee index 2.0... oeedee ea ceca es cee any tines 5 oa Hine ce se ene 478 Color index’. 6.6 o sc ee ba eee ene dee oo a W sin ok oy 6 ont Seele glrr 483 Intermediate andes’ <5 Guy ao eg eee oe ee MO Oy 496 Patéentee Index vidas ca dee ee bet ce meen 3 aie aes eo as One nee nn 532 Schulz index! (1914) 2.6 ac cbc cece ode wd ovine pitt o 8a en 577 DIGEST OF PATENTS RELATING TO COAL-TAR DYES AND ALLIED COMPOUNDS-’* INTRODUCTION Outline of work.—The patents covered by this digest* have been gathered from all available sources, including classes and subclasses of the United States Patent Office bearing upon chemicals and allied products; Schulz’ Survey of the Coal-Tar Dyes, (1914); Winther’s “Patente der organischen Chemie;” Dr. Seaman’s list of coal-tar colors and lists furnished by dye manufacturing companies, as well as patent citations gathered from other sources. Classifications of abstracts follow commonly accepted chemical groups. No divisions of the main dye groups have been made, since multiplicity of subdivisions increases the difficulty in locating patents, and raises questions as to accuracy of classification in a subject of ex- treme flexibility. When a patent claims the application of a dye to fiber, as a mordant or de- veloped dye, or as a lake or printing compound, and there is no patent for the dye as such, the abstract is included with the dye series. If, however, the dye is the subject of a patent, and there is also a patent for an application process or compound of the dye, the second abstract is placed with applications Group XXIII. Where products are known, but their dyeing properties have not been previously ascertained, the patent necessarily takes the form of application to the fiber, but is herein grouped with the dyes. When a patent claims only an intermediate, and indirectly the derived dye, either in the title or the text of the patent, the abstract is grouped with dyes. A large number of patents claim both process and product, while some cover one or the other or both, in separate patents. In the abstracts, each patent is con- sidered as process-product, whether both are claimed or not, and therefore two separate patents for process and for product are practically duplications. Foot- notes accompanying abstracts explain conditions. The general form of presentation of the information in the abstracts is fairly obvious, but certain features may need explanation. Differences between claims and title are shown in parentheses on line. with the title. Following this the chemical constitution of the product except in Groups VI and XV is expressed as clearly as possible without employing graphic formulas. Then follows an out- line of the process and the properties of the product, as given in the patent. The number and name of the dye as it occurs in Schulz’ Survey of the Organic Color- ing Matters, (1914 edition) is placed at the bottom of the abstract together with cross references to other patents, notes, and remarks. In outlining the process of manufacture, intermediates appear with chief function in bold-faced type as an aid in referring to them in the Intermediate In- dex. When several processes and intermediates are mentioned in the patent, not more than two or three are cited, either in abstract or index. Brief reference is 1 All patents, under the present law, expire 17 years from the date of original issue. 2See Vol. X, Twelfth Census of the United States,—Manufactures, Part IV, for Digest of Patents relating to Chemical Industries issued prior to Jan. 1, 1902—particularly Group XI, Dyestuffs and Extracts, artificial, organic, pp. 879-909, and Carbon Compounds, subgroup Nitro- gen compounds, pp. 962-966. ‘ Vi INTRODUCTION made to additional materials, to variations in process conditions, and to one or more intermediates, with a general class reference, such as “ANILIN, and other aryl amins” or “1-Chlor ANTHRAQUINONE-2-aldehyde, or deriv.,” or “2-Amino- 3-methyl-ANTHRAQUINONE, isomer or homolog,” or in some cases simply “or other,” to indicate that other similar compounds are enumerated in the patent. In the Intermediate Index, these will appear under the specific intermediate and under the class designation. Abbreviations. Much has been omitted concerning processes of a self-evident character. The main steps in the synthesis are noted, but filtration, precipitation, purification, drying, cooling, diluting, salting out, the kind of acid or alkali and the oxidizing or reducing agents used, frequently are not specified. Such phrases as “the separated product” or “the dried and purified material” imply that the suc- ceeding operation requires the product to be isolated at this point. This may mean one or a series of operations. In general, abbreviations of common words are used as in Chemical Abstracts, Journal of the American Chemical Society. Standardized phrases are used, in abbreviated form, especially with respect to properties of dyes. Superlative terms for fastness or other properties are ignored. The fibers, wool, silk, or cotton, are not mentioned in connection with dyeing properties, as the method of application indicates the kind of fiber. General reference to acids, alkalies, or caustic implies diluted solutions unless strength is specified. Parts means parts by weight; strengths of solutions are expressed in per cent or degrees Baumé; specific gravity is shown by figures in parentheses; temperatures are reported in degrees centigrade. In giving the properties of dyes, letters in parentheses following names of re- agents show the color of the solution or precipitate. The customary method of employing the initial letter or abbreviation of a color has been followed—violet (V), blue (B), green (G), yellow (Y), orange (O), red (R), brown (Br), black (Bk), and gray (Gy), with combinations for modifiers, such as green-gray (GGy), violet-red (VR), etc. Modifiers of color shade take the nearest secondary or primary color, for example, violet-blue, not reddish blue; orange-yellow, not reddish yellow; orange- red, not yellow red; violet-red, not bluish red. Violet is used in all cases for purple, orange-red for scarlet or scarlet red, and violet-red for magenta red. The termination “ish” for modifiers has been omitted—blue-green, not bluish green; green-yellow, not greenish yellow; etc. Dyes have been classified in relation to their application to the fiber into acid, acid mordant, basic, basic mordant, direct, developed, and reducing and sulfide vat. In addition there are lake making and oil soluble dyes. To some extent the classes overlap. Acid mordanting methods include the usual addition of dyes to previously mordanted fiber, the after treatment of dyed fiber with a mordant (after chroming, coppering, etc.,) and the one bath or metachrome process. Developed dyes include those capable of coupling with diazo compounds on the fiber or of diazotation on the fiber and developing with a coupling agent (ice colors, ingrain colors, etc.) ; those developed by oxygen of the air (Anilin Black) or oxidized by chemical salts such as chromates or copper compounds and by after treatment with formaldehyde. Vat dyes are roughly separated into reducing or hydrosulfite vat, and sulfur or sulfide vat, but sulfur dyes though frequently precipitated from NazS solvent and applied as reducing vat colors, are included among sulfide vat dyes. Chemical nomenclature.—In the use of chemical terms the rules adopted by the American Chemical Society in chemical abstracts have been followed, modified somewhat in accordance with common usage and for brevity, in order to make the digest as concise as possible without sacrificing clearness. INTRODUCTION vii 99 «66 9» 66 ” ’ Names of compounds ending in “ane,” “ene,” “ole,” when the vowel has the long sound, retain the final “e.” So also with the ending “ine” when pronounced as in “line;’ but with amin, anilin, toluidin, benzidin, etc., the final “e” has been omitted. “Oxy” is used for “hydroxy;” “o” has not been employed to separate syllables except as usage has sanctioned it; “sulfo” and “carbo” are used for sul- fonic and carboxylic acids; salts and esters are given as the free acid or base. The Intermediate index is a subject index with chief functions or index com- pounds arranged alphabetically. This chief function is shown in the index and the patent abstracts by bold-faced letters. Choice of chief function and order of precedence of substituents follow com- mon usage, index compounds being made as comprehensive as practicable. Sub- stituents that precede the index compound in the abstract follow the index com- pound in the index. For example—“4’/-Oxy phenyl 1-NAPHTHYLAMIN sulfo,” appears in the index as “I-NAPHTHYLAMIN, 4’-Oxy phenyl, sulfo.” A certain amount of standardization of nomenclature and of numbering was necessary, and all compounds were made to conform to such chosen standards. This necessitated some very careful work, the importance of which can readily be recognized. When the order of substituents or their positions was not clear, or was lacking in the patent, information in regard thereto was entered unaltered in the abstract and in the index. Numerals to designate positions of substituents with periods and hyphens to separate them have been employed, and Greek letters avoided as far as possible. The work has been brought down to January 1, 1924. PATENT ABSTRACTS. Dyes are classed in accordance with their final character. Anthraquinone derivs. fused in Na,S, etc., to convert into reducing vat colors are placed with suLFuR dyes. Pyrazolone derivs. used in usual way as coupling agents are to be found among Azo colors. COAL-TAR DYES. Group I.—ACRIDIN, 382,832—May 15, 1888. Christian Rupo.pH, Germany. (Oehler.) Production of yellow coloring-matter. (Product also claimed.) Diamino ditolyl acridin. Hydro diamino ditolyl AcrIDIN is oxidized by air or preferably by slowly acting agents such as FeCl, in dil. HCl soln., containing ZnCl, to ppt. metal salt. YELLow direct and basic mordant dye. . S. 605.—“Benzoflavin.”” Note 395,080. 395,080—Dec. 25, 1888. Christian RupoLtpH, Germany. (Ocehler.) Coloring-matter. 4-Amino benzoflavin. Hydro acripin base is dissolved in dil. HCI containing ZnCl, to which twenty per cent soln. of FeCl, is slowly added. Green YELLOW basic mordant dye. Near S. 605.—‘‘Benzoflavin.”’ Addition to 382,832. 503,305—Aug. 15, 1893. Fritz BEnpER, Germany. (Leonhardt.) Orange dye. Tetra methyl diamino acridin or homologs. 3-Amino dimethyl ANn1ILIN, or other substituted meta diamin, or dimethyl anilin, etc., is con- densed in alc. HCl with ForMALDEHYDE, benzaldehyde or formic acid (oxalic acid and glycerin) separated product further condensed by heating at 150° in autoclave with aq., leuco dye oxidized in HCl soln. with FeCl, and pptd. with ZnCl, Orancg basic mordant dye. S. 603 and 604.—‘‘Acridin Orange.” 516,577—Mar. 13, 1894. Erhart SCHLEICHER, Germany. (DPadische.) Basic yellow dye. Diamino phenyl acridin carbo acid, ethyl ester. FLUORESCEIN is treated with NH, so as to obtain a diamino acripiIn and product then re- fluxed in ninety-five per cent alcohol through which a stream of HCl gas is passed. Closed vessels under pressure and other alcohols and acids may be used for the esterification. YELLOW to ORANGK basic mordant leather dye. $37,723—Apr. 16, 1895. Jakob Scumip and Karl Jepuicxa, Switzerland. (Basle.) Orange dye. Alkylated dyes of acridin group. ACRIDIN YELLOW, benzoflavin or other, together with methyl alc. and HCl, or other, heated in closed vessel to 160-200°. YELLOW to ORANGE basic mordant dyes, for leather, etc. S. 603—‘‘Acridin Orange;’’ also 604, 605, etc. _ 546,177—Sept. 10, 1895. Carl Mutier, Germany. (Badische.) Brown-yellow dye. Product like Phosphine in properties. Tetra methyl diamino BENZOPHENONE condensed with 3-PHENYLENE DIAMIN HCI and 3- PHENYLENE DIAMIN by heating with ZnCl, in closed enameled vessel, on oil bath to 195-215°. The 3-amino phenyl auRAMIN first formed combines with diamin to form the new dye. S. 607—‘‘Rheonin A.” 617,340—Jan. 10, 1899. Paul Jutius and Georges E. DarirEr, Switzerland. (Badische.) Phosphin dye and process of making same. as-Diphenyl dimethyl triamino phenyl ditolyl acridin. Dimethyl 4-amino BENZALDEHYDE heated at 140-150° with phenyl 3-TOLUYLENE DIAMIN. YxLLow basic mordant dye, for leather, etc. Note 619,577. 619,577—Feb. 14, 1899. Paul Jutius and Akim Txatscu, Germany. (Badische.) Process of making yellow phosphin dye. Diphenyl triamino phenyl! ditolyl acridin. Phenyl 3-TOLUYLENE DIAMIN or homologs condensed by boiling with 4-amino BENZALDEHYDE or homologs, in presence of FeCl,. preferably in alc. soln. Completely oxidized dye thus ob- tained in larger yield and greater purity because by-reactions are avoided. YELLOW basic mor- dant dye, for leather. Addition to 617,340. 2 DIGEST OF PATENTS 637,183—Nov. 14, 1899. Henry TerrissE and Georges Daritr, Switzerland. (Badische.) Yellow basic dye. 2-Amino 3-methyl phenyl 1.2-naphth acridin. 2-NAPHTHYLAMIN is heated to 150° and to this is added a mixture of 2.4-diamino 5-methyl ToLUYL alcohol and 2-NAPHTHYLAMIN HCl then temp. raised to 170°, diluted, filt. hot, cooled, filt. to remove naphthylamin HCl, and base pptd. by alk. YxrtLow basic mordant dye, for leather. 643,569—Feb. 13, 1900. Fritz ULLMANN, Germany. (Berlin.) Yellow acridinium dye. Acridin dyes substituted in N position to form acridinium salts containing pentavalent nitrogen. Amino tolu napth AcRIDIN, two parts in boiling nitrobenzene soln., to which one part of DIMETHYL sulfate is added. Other components claimed. Orange-yELLOW basic mordant dye, fast to alk. carbonates. 644,324—Feb. 27, 1900. Paul Jutius and Walther Reiss, Germany. (Badische.) Process of making yellow basic dyes. Probably an amino tolu naphth-acridin. Diamino TOLUYL ALCOHOL, derived from 3-TOLUYLENE DIAMIN and FORMALDEHYDE, mixed with cryst. FeCl,, added to molten 2-NAPHTHOL at 140° then heated to 150-170°. YELLOW basic mordant dye. 666,095—Jan. 15, rgo1. Carl Jepuicxa, Switzerland. (Basle.) Orange dye and process of making same. Alkylated diamino ditolyl acridinium derivs. or other. PATENT PHOSPHIN G derived from ACRIDIN YELLOW and METHYL sulfate ‘‘a’’,* heated in autoclave at 100—110° with alcohol and METHYL chloride. If an alkyl sulfo acid is used solvent should be aq. free (Nitrobenzene, etc.), or diamino ditolyl methyl acridinium ‘‘b’? is heated in methyl alcohol-sulfuric acid at 160-170°. Other components claimed. *For alkylation in amino groups “a” or in N of nucleus “b” see 537,723 and 666,096. 666,096—Jan. 15, 1901. Karl JEDLICKA, Switzerland. (Basle.) Yellow acridin dye and process of making same. Diamino ditolyl N-ethyl acri- dinium. ACRIDIN YELLOW, alkylated by ErHy1 chloride, or other as in 537,723 to PATENT PHOSPHIN Gc. is then heated in alk. carb. or NH, soln. YELLOW to orange-YELLOW basic mordant dyes, fast to alk. 675,568—June 4, 1901. Oscar NastvocGELt, Germany. (Elberfeld.) Yellow acridin dye and process of making same. Phenyl tolyl acridin. Dimethyl diamino puENnyL tolyl methane, dinitrated (ortho), reduced to diamino compound, condensed and oxidized. YELLOW basic mordant dye. Near S. 60z2—‘“‘Acridin Yellow.” 709,187—Sept. 16, 1902. Arthur WEINBERG, Germany. (Cassella.) Yellow acridin dye and process of making same. Tetra amino pITOLYL methane heated at 145-150° with dil. HCl in autoclave, cooled, one mol. each of ANILIN and FORMALDEHYDE added and again heated at 105—110° in autoclave. Jeuco dye oxidizes in air. Alphyl, alcoyl, and leuco derivs. as well as other aromatic .amins are claimed. Orange-rREpD basic mordant fast dyes. 712,421—Oct. 28, 1902. Otto Soust, Germany. (Ho6chst.) Yellow to red acridin dye and process of making same. Tetra alkyl diamino benzyl acridinium or other. ACRIDIN YELLOW base or homologs, heated with BENZyL chloride in nitrobenzene as solvent or in slightly moist condition. YELLOW to RED basic mordant dyes, fast to sodium carbonate and NH,. 716,084—Dec. 16, 1902. Oscar NastvocEeL, Germany. (Elberfeld.) Yellow acridin dye and process of making same. Formate of acridin base. _ AcrIpDIN base or benzoflavin base, in dil. soln. of ForMIc acid or other mono basic fatty acid, evaporated to dryness at 100°. Green YELLOW basic mordant dyes. GROUP I.—ACRIDIN 3 716,264—Dec. 16, 1902. Carl L. MuuiEer and Ernst Scumip, Germany. (Badische.) Acridin dye. Phthalyl 3-roLUYLENE DIAMIN, or phthalic anhyd. together with 3-ToLUYLENE DIAMIN and its HCl salt, heated in enameled vessel to z00-210° with ZnCl, YELLOW to orange-RED basic mordant dye. 730-771—June 9, 1903. Karl Jepuicxa, Switzerland. (Basle.) Yellow acridin dye and process of making same. Diamino dimethyl! acridin. 3-TOLUYLENE DIAMIN and FORMALDEHYDE, acetic aldehyde, or other, heated in dil. HCl soln. at 130-140° in an autoclave, cooled and with ACETALDEHYDE heated at 80-90° in aq., pptd. as ZnCl, double salt. YELLOW to ORANGE basic mordant dyes, easily soluble. S. 60z2—“‘Acridin Yellow.” 739,117—Sept. 15, 1903. Otto Soust, Germany. (Hoéchst.) Yellow acridinium dye and process of making same. Acridinium dyestuffs, alky- lated at the acridin N and in amino groups. 3-TOLUYLENE DIAMIN or other in strong HCl soln., FoRMALDEHYDE added and equiv. amount of ACETALDEHYDE, or other, slowly added at common temp., soln. then heated with more HCl in closed vessel to 140°, cooled, METHYL alcohol added and heated to 170°, finally oxidized by air and FeCl,. More methyl alcohol and higher temp. gives redder and ethyl alcohol a yellower product. YELLOW basic mordant dye. Near S. 602—“‘Acridin Yellow.’? Note related pats. 666095 and 96. 740,468—Oct. 6, 1903. Christopher Ris and Albert Myzius, Switzerland. (Geigy.) Acridin dye and process of making same. Diformyl 3-TOLUYLENE DIAMIN and 3-TOLUYLENE DIAMIN, heated with anILIN HCl gradually to 160° till maximum color develops. Other components claimed. YELLOW to ORANGE and BROWN basic mordant fast dyes. 746,981—Dec. 15, 1903. Carl L. MuLuerR, Germany. (Badische.) Acridin dye and process of making same. ACRIDIN YELLOW with two parts GLYCERIN heated to 170—-180°, diluted, pptd. with NaCl and HCI salt formed. Other acridin dye-glycerin comps. claimed. ORANGE to YELLOW basic mordant dyes. 766,540—Aug. 2, 1904. Otto Soust, Germany. (Héchst.) Orange dye and process of making same. Alkylated glycin acridin. 3-TOLUYLENE DIAMIN condensed with FORMALDEHYDE in HCl soln. to form leuco acridin, then with CHLORACETIC acid to form leuco glycin acridin, alkylated and finally oxidized. ORancxr to RED basic mordant dyes. 794,052—July 4, 1905. Otto Soust, Germany. (Hoéchst.) Orange-red acridin dye. (Process also claimed.) ACRIDIN YELLOW, or leuco dye, salt or base, alkylated with HCl and atconon then product heated in dil. H,SO, with FoRMALDEHYDE. Dye pptd. as Zn salt. Orange-rEpD basic mordant dye. 1,005,176—Oct. 10, 1911. Paul Enriicu and Louis Benpa, Germany. (Cassella, N. Y.) 3.6-Diaminoacridinium and its salts. 3.6-Diamino N-alkyl acridin and salts. 3.6-Diamino acRIDIN is diacetylated, separated as NH, salt, heated to 180° in 10 parts nitrobenzol and one mol. ToLUENE 4-sulfo, methyl ester, added, crystals separated and saponified in HCl at 110°. YELLOW to ORANGE basic mordant dye, fast to soda and soaping. 1,255,739—Feb. 5, 1918. Heinrich GRUNHAGEN, Germany. (Berlin.) Halogenated dye of the acridin series. (Process also claimed.) Halogen as-dialkyl diamino acridin. 2-Amino formyl 4-amino CHLORBENZENE melted together with 3-amino dimethyl ANILIN at 180°, diluted, filt. and pptd. by NaCl or ZnCl,. Process is essentially the same as that em- ployed in 1889 by Bender. (S. 602). Orange-yELLow basic mordant dye. : Near S. 602—“‘Acridin Yellow G.” Note addition pat. 1,226,740. 4 | DIGEST OF PATENTS 1,255,740—Feb. 5s, 1918. Heinrich Grunuacen, Germany. (Berlin.) Dyes of the benzene-naphthalene series and process for their manufacture. Naphthyl dialkyl amino acridin. Formyl 2-NAPHTHYLAMIN, or other, melted together with 3-amino dimethyl an1zr1n HCl, or other, to 160-190°. ORANGE to orange-YELLOW basic mordant dyes. Addition to 1,285,739. 1,418,852—June 6, 1922. Charles VAUCKER and Rene SpEITEL, Switzerland. (Durand.) Halogen derivatives of basic acridine dyestuffs and process of making same. Acridin dyes with more than one atom halogen in molecule. ACRIDIN ORANGE sulfate (tetramethyl 2.7-diamino acripIN disulfate) mixed with NaBr added to 8 parts conc. H,SO, at 0° for several hours then heated at 50° till sol. in aq. with red color. Br vapor in nitrobenzene soln. aided by NaClO,, or excess Br alone may be used. Red basic mordant dyes. Note 1,255,739 for halogen acridin dyes by another process. 1,427,431—Aug. 29, 10922. Louis Benpa, Germany. (Cassella.) Compound of the acridine series and a process of making same. Acridin dyes condensed with formaldehyde. 3.6-Diamino N-methyl acripiIn HCl, homologs or analogs, in dil. HCl condensed with FORMALDEHYDE at usual temp. Amount of formaldehyde may vary greatly. YELLOW basic mor- dant dyes, useful also for medicinal purposes. Note 1,427,432 among applications. 1,427,432—Aug. 29, 1922. Louis Benpa, Germany. (Cassella.) Acridinium compounds and a process of making the same. Tannin lakes of acridin dyes. 3-6-Diamino N-methyl acriptn HCl*, homologs, etc., in aq. soln. mixed with 2 parts TANNIC acid containing sod. acetate. Compounds are suitable for lake colors and for medicinal comp. *T rypaflavin.” 1,455,486—May 15, 1923. Heinrich Grinuacen, Germany. (Chem. Found.) Dyes of the acridine series and their manufacture. as-Dimethyl 2.7-diamino 3.6- dimethyl acridin, or other. Formyl 4.3-TOLUYLENE DIAMIN and equimol. 3-amino dimethyl ANILIN are heated at 185- 190° with or without a diluting agent such as glycerin or naphthalene until no more H,O is evolved (about 6 hours). Homologs and diformyl derivs. of toluylene diamin may be used. Yellow-brown powds., sol. in aq.; YELLOW to orange-RED to BROWN basic mordant dyes for leather. Near S. 602 or 603—‘‘Acridin Yellow” or “‘Acridin Orange.”’ 1,455,487—May 15, 1923. Heinrich GriNHAGEN, Germany. (Chem. Found.) Dyes of the acridine series and process for their manufacture. Ethyl dimethyl 2.7-diamino 3.6-dimethyl acridin. Process is same as 1,455,486 except that both amino groups are substituted by alkyl. Red- brown powds.;.yELLOwW basic mordant dyes for leather. Near S. 602—‘“‘Acridin Yellow.” 1,455,488—Sept. 10, 1923. Heinrich Griinnacen, Germany. (Chem. Found.) Dyes of benzene-naphthalene-acridine series and their manufacture. 2-Amino 3-methyl phen naphthacridin. Process is similar to 1,455,486, except that one of the components is 2-NAPHTHYLAMIN Of deriv. 1,473,550—Nov. 6, 1923. Heinrich GriinHacen, Germany. (Berlin.) 2.7-dialkyl-3-dialkylamino-6-amino-10-alkylacridinium salts. One part 2.7-dimethyl dimethyl 3-amino 6-amino AcRIpDIN suspended in 2.5 parts methyl alc. with a soln. of 0.47 parts METHYL bromide or other alkyl halogen in 1 part methyl alc. is heated in an autoclave for 6 hours at 130°. Alcohol is removed by distn., boiling aq. soln. of product made weakly alk. with Na,CO, and pptd. by salt. Heated with excess NaOH the acridinium base is sepd., and HCl salt may then be formed. YELLOW basic dyes. GROUP II.—ANILIN BLACK 5 Group I1—ANILIN BLACK. 38,589—May 109, 1863. Re. 4,746—Feb. 6, 1872. Div. A. John Licurroot, England. (Pack.) Improvement in dyeing and printing textile fabrics and yarns with anilin black. ANILIN is oxidised by KC1O,, perchloride of copper, NH,Cl, etc. Methods for dyeing and printing are given. A BLAcK developed dye that resists chemical reagents. S. 922—“‘Anilin Black.” Note also 79,942 (Benoit Bloch) in which arsenic acid is used as oxidizing agent; 96,242 (Charles Lauth) in which permanganate salts are used; 111,654 which employs chromates, chlorates, copper, iron, uranium, or vanadium salts; and 193,158 (W. J. S. Grawitz), which employs sesquioxide of iron, chromates, or chlorates. 38,589—May 10, 1863. Re. 4,747—Feb. 6, 1872. Div. B. John Licurroot, England. (Pack.) Improvement in fabries dyed with anilin black. ANILIN in HCl soln. added to soln. of KCI1O,, acetic acid, perchloride of Cu, and NH,Cl etc. Fabric or yarn is steeped in this solution, wrung out, dried, steamed, or aged at 10-20°, then passed through alk. aq. Printing process described and other components claimed. S. 922—‘“‘Anilin Black.” 79,942—July 14, 1868. Re. 3,103—Sept. 1, 1868. Benoit Biocu, France. Improved anilin dye. ANILIN on fiber oxidised by arsenic acid. Used in dilute solution, gray is produced in- stead of black. Gray to sLAcKk developed dyes. S. 922—“‘Anilin Black.” 96,242—Oct. 26, 1860. Charles Lautu, France. Improved coloring-material for dyeing and printing. (Process, not product, claimed.) ANILIN, toluidin, cumidin, napthylamin, etc., and an oxidising agent, preferably per- manganic salts, applied and developed on fiber as dye or print. Buiacx developed dyes. S. 922—“‘Anilin Black.” 111,654—Feb. 7, 1871. (See Re. 7,429-7,432.) John LicutTrFoor, England. Improvement in dyeing and printing textile fabries. ANILIN, oxidised in printing paste or on fiber using chlorates, copper salts, chromates, iron, uranium or vanadium salts. A BLACK developed dye. Method of producing cream of tartar by double decomp. of sod. or ammonium acid tartrate and KCIO, is also claimed. Re. 7,429—Dec. 12, 1876.—-Division A claims use of chlorate of soda as oxidizer with sol. salts, oxides, sulfides or finely divided metallic Fe as catalysts. Re. 7,430—Dec. 12. 1876.—Division B claims chlorate of ammonia as oxidizer, also with sol. salts, oxides sulfides or finely divided metallic Fe, as catalyst. Re. 7,431—Dec. 12, 1876.—Division C claims use of an alkaline chlorate as oxidizer with vanadium, its salts, oxides or sulfides as catalyst. Re. 7,432—Dec. 12, 1876.—Division D claims use of an alkaline chlorate as oxidizer with uranium, its salts, oxides or sulfides as catalyst. S. 922—‘“‘Anilin Black.” 134,076—Dec. 17, 1872. Francois Lamy, France. Improvement in dyeing fabrics with naphthylamine colors. NAPTHYLAMIN and derivs. oxidised by chloric, chromic and hydrofluosilicic acids, iron or copper salts and further treated with chlorine or ammonia, etc., to develop brown violet shade. Rep to vioLEt developed dyes suitable for printing, equal to madder dyes. 138,155—Apr. 22, 1873. James Hiccin, England. Improvement in dyeing with aniline black. Use of disulfocyanide of copper as an assistant oxidizer, with anilin HCl free of excess acid. AniuIn base, com’l., 100 parts mixed with soln. of 250-280 parts of iron sesquichloride or 400-450 parts chromium sesquichloride (50° Tw.). For printing pastes, this is compounded with copper disulfocyanide paste made by mixing 2 parts cryst. CuSO, and 3 parts cryst. FeSO, in aq. soln. and adding KSCN. ; S. 922—“Anilin Black.” 6 DIGEST OF PATENTS 189,538—Apr. 10, 1877. Justus WouFr and Ralph Betiey, England. Improvement in production of coloring matters from aniline. ANILIN, with or without toluidin or xylidin, oxidized with nitro benzene or nitro toluene by heating gently with SnCl, crysts. then raising temp. to 200-220° until sol. in aq. with brown yellow color. Instead of SnCl, may be used either HCl or arsenic acid, Cl gas, Br, I, MnO,, PbO,, HNO,, or nitrate, chloric, bromic, or iodic acids, with oxygen, metallic perchlorides, CuSO,, etc. Gray to BLack developed dyes. S. 922—“‘Anilin Black.” 193,158—July 17, 1877. William J. S. Grawitz, France. Improvement in dyeing yarns and fabrics in anilin-black. Process for apply- ing anilin black or gray to cotton, flax, wool, silk, feather, etc. ANILIN oxidised by perchloride of iron and chromates or chlorates, manganates, permanga- nates, tungstates, vanadates, bivanadates, uranates, ferricyanides and cerium, nickel, cobalt, etc., comps. of metals whose salts are readily converted to lower degrees of oxidation. Gray to BLACK developed dyes. S. 922—‘‘Anilin Black.” 298,998—May 20, 1884. Prosper Monnet, France. (Monnet.) Obtaining brown dyes from the aromatic diamines. 4-PHENYLENE DIAMIN HCI, or other, in dil. H,SO, soln. thoroughly impregnated on fiber which is wrung out and oxidized in bath containing KClO, and salt of vanadium for slow action, or bichromate to develop more rapidly. Fabric may be immersed more than once and may be mordanted; cotton must be mordanted with sumac for deep shades. Brown developed dyes. S. 923—‘‘Ursol D.” Schulz credits patent to E. Erdmann, 1888. 355,934—Jan. 11, 1887. Thomas Hoturpay, England. Dyeing textile animal fibers. Dyeing animal fibers with product of oxidization of napthol. Fiber steeped in dil. H,SO, soln. of bichromate washed and dyed in 1-NapPtHorn soln. with or without other colors such as Indigo extract to obtain mixed shades. Shade varied by quantity of material. Brown to BLAck developed dyes (not claimed). 387,097—July 31, 1888. Prosper Monnet, France. Dyeing colors by the simultaneous oxidation of diamines and monamines. (a) 4-PHENYLENE DIAMIN HCl and anizt1in HCl in molecular proportions. (b) Sodium chlorate, and ammonium vanadate in HCl soln., largely diluted. Fiber is dipped in mixture of equal vols. of (a) and (b) then aged in air. Briacx developed dyes. S. 922—“‘Anilin Black.” 681,613—Aug. 27, 1901. René Boun, Germany. (Badische.) Process of dyeing. Dyeing with tetroxy naphthalene. Wool fiber is treated in dil. acetic bath with tetroxy NAPHTHALENE, bichromate added to bath, which is further heated for three-fourths hour. Methods for dyeing silk and cotton given. Brown to BLACK acid mordant (Al) or developed (CrO,) dyes. 739,071—Sept. 15, 1903. Emile A. Fournraux, New York. (Metz.) Process of dyeing brown. Fabric padded or printed with soln. containing 3-TOLUYLENE DIAMIN, or other, with acid (preferably mineral), gum, tragacanth, NaClO,, AICI, and a little cerium or copper chloride as catalyzer (or mixture of these) steamed or aged as usual. Product differs from diamin browns. Brown developed dye, suitable for printing. 787,221—Apr. 11, 1905. Alexander S. Ramacg, Michigan. Electrolytic method. Electrolytic mfr. of anilin black. An aq. soln. of a metallic salt is electrolyzed with an insoluble anode, cathode product is recovered, and an ANILIN comp. oxidized at the anode to anilin black, which is separated and acid anode liquor again used. Sod. sulfate with lead anodes, NaCl with graphite anodes and FeSO,, etc., using H,SO, or HCl and corresponding anilin salt are claimed. S. 922—“Anilin black.” GROUP II.—ANILIN BLACK 7 796,715—Aug. 8, 1905. Victor Fusscancer, Germany. (Hochst.) Process of dyeing violet to black. (Product also claimed.) 4-Amino DIPHENYLAMIN or its derivs. jointly oxidized on the fiber with rEsorcin, or other phenol or amin, one mol. each, by applying the two together with a chlorate or other oxidizing agent and various assistants to the fiber, drying, developing, fixing, etc., by heat or steam. BLUE, VIOLET to BLACK developed dyes fast to alks. acid, light, and organic solvents. 800,735—Oct. 3, 1905. Hugo GELDERMANN, Germany. (Berlin.) Diamidodiphenylamin sulfonic acid and process of making same. 4-Methyl 3-amino 4’-nitro DIPHENYLAMIN 2-sulfo derived from 4-nitro CHLORBENZENE-2-sulfo and 3-PHENYLENEDIAMIN, boiled in dil. HCl with Zn powd., soln. made alk., filt., made slightly acid with HCl and pptd. by salt. Buur developed dye when oxidized on fiber. (Not claimed.) 863,761——‘‘Anthraflavon G.” 844,835—Feb. 19, 1907. Karl Tuun, Germany. (Bayer.) Anthracene derivative. N-Methyl 4/-tolyl anthraquinoyl azin and derivs. 4/-Tolyl 1-amino 2-amino ANTHRAQUINONE, 1 part, with 1 part forty per cent FORMALDEHYDE heated to 100° in 10 parts glac. acetic. Other amino aryl amino anthraquinones, with the amino group in ortho position to the aryl amino, and other aldehydes are claimed. Dark cryst. powds., insol. in aq. unless sulfonated; sulfo derivs. are BLUE acid dyes. 844,914—Feb. 19, 1907. Rene Boun, Germany. (Badische.) Process of making an anthracene dye. Halogen indanthrene faster to Cl than 739,579. INDANTHRENE treated with Sb,Cl, in nitro benzene solution to form chlor derivatives. BLuE 34 DIGEST OF PATENTS vat dyes (properties not claimed), fast to Cl. Note 753,659. 847,078—Mar. 12, 1907. Michael Inyinsxy, Germany. (Wedekind.) Production of organic sulfonic acids. Poly sulfo acids of anthraquinone, containing one sulfo group in the (1), position. ANTHRAQUINONE 2.6- or 2.7-disulfo acid, sodium salt, heated at 160° in 2 parts fuming sulf. (forty per cent SO,), containing one per cent HgSO,. Melting with lime yields an oxy an- thraquinone sulfo acid which is a violet RED acid mordant dye. 853,041—May 7, 1907. Paul THoMAsScHEWSKI, Germany. (Badische.) Anthraquinone derivative. Methyl anthra-pyridone and derivs. Methyl 1-amino ANTHRAQUINONE, the para nitro, para methoxy, or other alfa aryl amino an- thraquinone, boiled with acrric anhyd. to form acetyl deriv., then condensed by boiling in 50 parts alkali, separated and sulfonated by heating gently with 20 parts monohydrate acid. A table of reactions is given. Prods. are cryst., insol. in aq., sol. in pyridin, and in conc. sulf. (Y-R), the sulfonated products are sol. in dil. alk. (VR); and are violet RED acid or acid mordant (Cr) dyes. Note 875,390. 855,248—May 28, 1907. Max IsiterR, Germany. (Badische.) Process of making anthracene dye. Indanthrene by another process. 1-Amino ANTHRAQUINONE one part heated with 1 part twenty to thirty per cent HCl or other condensing agent (acids and salts enumerated) with or without oxidizing substance, either dry or in condensed or dil. soln., to form an azin. A BLUE vat dye. Probably S. 837—“‘‘Indanthrene Blue R.” Note 682,523 for alkali condensation, and also 724,789. 856,811—June 11, 1907. Roland H. Scuont, Germany. (Badische.) Dye of the anthraquinone series and process of making same. Pyranthrene and derivs. Halogen 2-methyl ANTHRAQUINONE or derivs., condensed, using copper or other metal capable of withdrawing halogen, to 2.2’-dimethyl 1.1’-dianthraquinonyl comp. then refluxed in methyl or ethyl alcohol with KOH or other condensing agent to, further condense to a pyranthrone which is oxidized by air to pyranthrene. Yellow to brown powds., insol. in aq. and dil. acids and aiks., sol. in conc. sulf. (B) and in hot C,H,NO, and C,H;NH,; YELLOW to ORANGE vat (R) dyes. S. 760—‘‘Indanthrene Gold Orange G.’’ Addition to 828,778. 860,480—July 16, 1907. Max IsuerR, Germany. (Badische.) Anthracene dye and process of making same. Probably an indanthrene. 1-Amino ANTHRAQUINONE and 2-chlor ANTHRAQUINONE condensed to 1.2/-DIANTHRAQUINONYL- AMIN, nitrated in 20 parts nitrobenzene soln. by 1 part ninety-three per cent HNO, to dinitro- dianthraquinonylamin which is melted at 100° in 5 parts Na,S. Blue powd. or paste, insol. in aq., dil. acids and alks., sol. in conc. sulf. (GBr) pptd. on diln. (B); BLUE vat dye. Addition to 814,137. 863,397—Aug. 13, 1907. Max Ister and Philip: Kacrer, Germany. (Badische.) Anthraquinone compound and process of making same. 2/.2’/-Dianthraquinonyl 1.5-diamino anthraquinone, isomers and derivs. 1.5-Diamino ANTHRAQUINONES, or isomers, derived from nitro comp., refluxed with 2 mols. 2-chlor ANTHRAQUINONE or other beta halogen comp. in 20 parts naphthalene, toluene or nitro- benzene, containing anhyd. sod. acetate and Cu,Cl,. Products are insol. in aq., dil. acids and alks., diff. sol. in organic solvents, sol. in conc. sulf. (G), bluer on heating; rED vat (R-Br) dyes, or in sulfonated form are green GRAY and RED acid dyes as fast to acids, alks., Cl and light as vat dye. S. 826—‘Indanthrene Red G,”’ S. 828, “Indanthrene Bordeaux B,” S. 830, “‘Indanthrene Red R.” Schulz uses the formula 1’.1”%-dianthraquinonyl 2.6-diamino-anthraquinone. 863,401—Aug. 3, 1907. Filip Kacer, Germany. (Badische.) Anthracene dye and process of making same. 4.4’-Diamino 1.1’-dianthraquinone or halogen deriv. Acetyl 1-amino ANTHRAQUINONE, or halogen deriv., refluxed with POCI,, etc., and separated @ eigenen is GROUP III.—ANTHRAQUINONE 35 halogen product condensed in nitrobenzene, acetic anhydrid, alcohol, naphthalene, etc., using cuprous, aluminum or ferric chloride as condensing agents. Products are insol. in caustic, sol. in conc. sulf. (R-BrR); slur vat (YBr) dyes, blue color being developed with neutral hydro- sulfite. 868,399—Oct. 15, 1907. Rene Boun, Germany. (Badische.) Anthracene dye and process of making same. Probably a poly oxy dianthraquinone xanthone. Hexaoxy ANTHRAQUINONE (Anthracene Blue WR ext.) or other oxy anthraquinone heated in alk. sulfite with FORMALDEHYDE, then pptd. by acid. Products are sol. in aq. (BR-YBr), in dil. NaOH (VR-RBr), in conc. sulf. (OR-V), on diln. (R-YG); violet BLUE to red BROWN acid mordant (Cr) dyes. 8$74,743—Dec. 24, 1907. Joseph Drinet, Germany. (Bayer.) Anthracene dye. Probably a dianthraquinone. _ANTHRAQUINONE, heated with powd. copper or other metal and 20 parts 66° sulfuric acid to 100-120°. A black paste diff. sol. in organic solvents, in conc. sulf. (dull Br); a Brown vat (dull V) dye. S. 872—“Leucol Brown B.” Note 874,744, and also that Schulz gives different materials and method. 874,744—Dec. 24, 1907. Joseph Dertnet, Germany. (Bayer.) Anthracene dye. Probably dimethyl 1.1’-diamino dianthraquinone or N-dimethyl indanthrene. Methyl 1-amino ANTHRAQUINONE heated at 90-100° with aluminum bronze (or copper, silver or the like) in 20 parts 66° sulfuric acid. Green black paste diff. sol. in conc. sulf. (dull V); olive GREEN vat (R) dye. S. 866—“‘Leucol Dark Brown B.” Addition to 874,743. 875,390—Dec. 31, 1907. Paul THoMASCHEWSKI, Germany. (Bayer.) Anthraquinone derivative. 2-Anthraquinonyl N-methyl 1-anthrapyridonyl amin or di-1.1’- anthrapyridonyl amin. Acetyl methyl 1-amino 4-brom ANTHRAQUINONE treated with alkali to form 4-brom anthra pyridone, which is condensed with 1 mol. 2-amino ANTHRAQUINONE by heating in naphthalene soln. with Ca(OH), and Cu,Cl,. See list of reactions for other components, Method for dyeing in vat given in detail. Dark brown powds., sol. in hot quinolin (R) and conc. sulf.(V);- RED tO BLUE vat dyes or as sulfo derivs. RED to BLLUE acid dyes. S. 825—‘“‘Algol Red B.” Addition to 853,041. 876,190—Jan. 7, 1908. Max H. Isuer, Germany. (Badische.) Anthracene dye and process of making same. Probably an indanthrene nucleus. 1- or 2-Amino ANTHRAQUINONE or derivs., heated at 90° in sixty per cent sulfuric acid with powd. copper or other metal. Products are insol. in aq. and caustic, sol. in conc. sulf. (GBr-RBr) not changed by boric acid, sol. in seventy-eight per cent HNO, (YBr-RBr); brown GREEN to BROWN vat (BrV-V) dyes. S. 867—“Indanthrene Brown B.”’ 876,810—Jan. 14, 1908. . Max. A. Kunz, Germany. (Badische.) Anthracene dye and process of making same. Halogen pyranthrones. 2.2’-Dimethyl 1.1/-DIANTHRAQUINONYL, or similar comp., heated with alc. KOH in nitrobenzene asin 299,775, and product heated at 60—-70° with sulfuryl chloride, Cl gas, or other halogenizing agent in nitrobenzene soln. then pptd. by alc. Yellow to brown powds., insol. in aq., dil. acids and alks., sol. in conc. sulf., in hot C,H,NH, and C,H,;NO,; orange rED vat (VR) dyes. Addition to 299,775. 885,577—Apr. 21, 1908. Johann H. Boner, Germany. (Badische.) Process of making alizarin. Dioxy anthraquinone. ANTHRAQUINONE heated at about 200° in mixed NaOH and KOH soln. with KCIO, or other oxidizing agent, dissolved in aq. and air blown through to reconvert oxanthrol present to anthra- quinone and alizarin, pptd. by Ca(OH),, purified, etc.; a RED acid mordant dye. S. 778—‘‘Alizarin.” 30 DIGEST OF PATENTS 893,412—July 14, 1908. Hugo Wourr, Germany. (Badische.) Anthracene dye and process of making same. Benzanthrone indanthrene and derivs. Amino BENZANTHRONE (from nitro compound), heated in nitrobenzene soln. with anhyd. sod. acetate and a metallic salt or oxide such as Cu,Cl, as condensing agent. Brom, di and tri amino, and quinolin derivs., etc., also claimed. Products are insol. in aq., in dil. acids and alks., diff. sol. in quinolin (Br-BrR), sol. in conc. sulf. (RBr-VB); yELLow, RED to violet BROWN vat (BrGr-BrR) dyes. 893,508—July 14, 1908. Max H. Ister, Germany. (Badische.) Anthracene dye and process of making same. Probably indanthrene derivs. 4.4’-Diamino 1.1/-DIANTHRAQUINONYL amin, the dinitro compound of 860,480, or any dianthra- quinone compound united by an imino group having an amino group in ortho position to a car- bonyl group, heated in fuming sulf. with glac. acetic, or with acetic anhyd. and sulfur when nitro comps. are used. Products are insol. in aq., and alk., diff. sol. in alc., glac. acetic, and acetone, sol. boiling C,H,;NO, and quinolin; pLuE vat dyes. Note 860,480. 893,837—July 21, 1908. Joseph Drinet, Germany. (Bayer.) Green anthracene dye. Probably an oxy indanthrene. INDANTHRENE of 682,523, 1 part, in 15 partS NITROBENZENE to which 1 part ninety-five per cent HNO, is added, held at ordinary temp. for several hours, then heated to 60-65° for 0.5 hour. Gray green powd., sol. in cone. sulf. (YBr) pptd. on diln. (G); GREEN vat (B) dye. 902,895—Nov. 3, 1908. Bertram Mayer and Alfred ScHaarscHmip?, Switzerland. (Basle.) Orange-to-yellow vat dye and process of making same. Composition not in- dicated. w-Dichlor 2-methyl] ANTHRAQUINONE, the mono chlor deriv., the crude mixture of both, or other, is heated with 0.3 to 3.0 parts sulfur at 200-290° for 3-4 hours; melt freed of sulfur by extraction with CS, or aq. Na,S, aq. paste of product heated to 100° and NaOCl added. Yellow to orange powds., sol. conc. sulf. (BR-RV), in fuming acid (BkG), slightly sol. in organic sol- vents; ORANGE tO YELLOW vat (RBr-VBr) dyes, fast to washing, light and chlorine. S. 795—‘“‘Cibanone Yellow R.” 906,367—Dec. 8, 1908. Oscar Baty and Hugo Wo.rr, Germany. (Badische.) Anthracene dye and process of making same. (Process not claimed.) Iso violan- throne and derivs. Chlor BENZANTHRONE, or other halogen deriv., (prepared as in F. P. 6,719, ninth addition to 349,531), heated at 150° with potassium or sodium alcoholate. Products are sol. in conc. sulf. (G), in C,H;NO, (RV); red vioLET to BLUE vat (B) dyes. S. 766—‘‘Indanthrene Violet R.”? Note 809,894 and 818,336 for isomeric comps. 909,800—Jan. 12, 1900. Max H. Ister, Germany. (Badische.) Anthracene dye and process of making same. Probably an indanthrene. 2-Amino ANTHRAQUINONE heated at 250-280° in 10 parts nitrobenzene with equal weight AICI,,. Products are insol. in aq., in NaOH, in alc., sol. in sulf. (BBk-GBk), partly sol. in C,H,NO, (YBr-GBk); red Brown vat (RBr-YBr) dyes. Product differs from that obtained in absence of a solvent. 915,385—Mar. 16, 1909. Alfred ScHAARSCHMID?T and Bertram Mayer, Switzerland. (Basle.) Brown vat dye and process of making same. Probably an indanthrene thiazin. 1-Amino 2-methyl ANTHRAQUINONE or other amino, or alkyl or acidyl deriv., heated to 240- 280° with 3 parts sulfur. Dark brown to black powds., sol. in conc. sulf. (Br-VBr), insol. in alc., glac. acetic, and C,H,; yellow Brown to violet BROWN vat (Br-V) dyes, fast to washing and light. S. 868—‘“‘Cibanon Brown B.” 916,154—Mar. 23, 1909. Julius HorFMANnNn, Switzerland. (Basle.) Gray vat dye and process of making same. Phenyl derivs. of indanthrene thiazin. Phenyl amino 2-methyl ANTHRAQUINONE or other aryl amino deriv., heated in 3 parts S. at 280-290°. Black powds., sol. in conc. sulf. (GBk-BrG) in twenty-four per cent oleum (BrG-Bk), insol. in organic solvents; GRAY vat (Br) dyes. ieee mel GROUP III.—ANTHRAQUINONE 37 922,282—May 18, 1900. Max IsiErR, Germany. (Badische.) Anthracene dye and process of making same. Composition not shown. ANTHRACENE, or a non oxidized substitution comp. such as the di or tri-chlor, chlor-brom, methyl or amino deriv., is heated at 250-360° with 3 parts sulfur until evolution of H,S ceases. Prods. are insol. in aq., in alks., in dil. acids and common organic solvents; and are green YELLOW to BROWN vat (Br-B) dyes. S. 791—‘Indanthrene Olive G.” 925,917—June 22, 19009. Filip Kacer, Germany. (Badische.) Compound of the anthracene series and process of making same. Probably anthrapyridone derivs. Acetyl 1-amino ANTHRAQUINONE or other acetyl or diacetyl diamino deriv., refluxed with 2 parts POCI, or other halogenating comp., such as sulfuryl chloride, etc., as reagent. Products which are weak bases, are light brown to red powds., insol. in aq., dil. acids or alks., diff. sol. in organic solvents, sol. in conc. sulf. (R), unchanged at 70°; orange RED, BROWN to YELLOW vat dyes. S. 812—“‘Indanthrene Orange RT,” and S. 813, “Indanthrene Copper R.” 928,891—July 20, 1909. Paul THOMASCHEWSKI, Germany. (Bayer.) Wat dye. 2’-Anthraquinonyl 4-anthriminonyl amin. 1-Nitro 4-amino ANTHRAQUINONE condensed with 2-chlor ANTHRAQUINONE and reduced to form 2/-anthraquinonyl 1.4-diamino ANTHRAQUINONE, which is condensed with vurREa in phenol soln. Dark red cryst. powd., diff. sol. organic solvents, sol. conc. sulf. (VB); fast violet RED vat dye. 929,442—July 27, 1909. Max H. Isier, Germany. (Badische.) Anthracene dye and process of making same. Halogen pyranthrones. 3- or 4-Chlor PHTHALIC anhyd., condensed with TOLUENE by Friedel-Crafts reaction and re- sulting chlor methyl deriv. nitrated, reduced, diazotized, and treated with Cu, to form 6.6’- dichlor 2.2’-dimethyl 1.1/-DIANTHRAQUINONYL, or 7.7’ deriv., which is refluxed in alc. KOH. Halo- gen is not lost in reaction. Yellow to brown powds., insol. in aq., acids., alks., sol. in conc. sulf., hot C,H,NO, and C,H,.NH, (R); orange RED vat (VR) dyes. Addition to 856,811 and 876,810. 929,443—July 27, 1909. Max H. Isier, Hugo Worrfr and Filip Kacrer, Germany. (Badische.) Anthracene dye and process of making same. alfa-beta-Dianthraquinonyl imines with two ketonic groups of each anthraquinone intact, and at least one anthraquinone having a nonreactive substituent. Methyl 1-amino 6- or 7-chlor ANTHRAQUINONE, or other beta chlor deriv., condensed with 1- amino ANTHRAQUINONE, or other alfa amino deriv. by boiling in nitrobenzene soln. with CuO and calcined soda, etc. Products are sol. in cold conc. sulf. (BrR-VB) containing boric acid, when heated (R-B); RED to violet BROWN vat dyes. Note 814,137. 931,618—Aug. 17, 1909. Filip Kacrer, Germany. (Badische.) Anthracene dye and process of making same. 2’-Anthraquinonyl 2-methyl 1-an- thrapyridonyl imin, and derivs. 4-Amino 2-methyl ANTHRAPYRIDONE, refluxed in nitrobenzene soln. with 2-chlor ANTHRAQUI- NONE, using CuCl, and anhyd. sod. acetate. Other components claimed. Products are insol. in aq., acids, alks., alc., and C,H,, sol. in C,H;NO, and quinolin, and conc. sulf. (V); RED vat dyes. 932,290— Gray dye. (Process also claimed.) Probably an intramolecular condensation of safranin and formaldehyde. Dimethyl saAFRANIN, or homologs, condensed in 2 parts conc. HCl with 1 part FORMALDEHYDE (forty per cent) by heating at 100°, soln. diluted and pptd. by ZnCl,. Gray basic mordant dyes, fast to soap and alk. 592,608—Oct. 26, 1897. Bernard Heymann and Rudolf Reyvurr, Germany. (Bayer.) Red azin dye. (Process also claimed.) Ethyl tolu safranin and derivs. 4-Amino ethyl 2-toluidin HCl (ethyl 3-roLtuyLENE DIAMIN) and ethyl 2-TOLUIDIN, 1 mol. each in aq. soln. and to this at common temp. is slowly added a soln. of bichromate to condense to an INDAMIN. More bichromate and one mol. ANILIN are added, mixture boiled and dye filtered out and purified. Rep basic or basic mordant dyes, fast to alk. and light. S. 684—“‘Brill. Rhodulin Red B.” 602,544—Apr. 19, 1808. Philip Orr and Thilo Krorser, Germany. (Elberfeld.) Blue azin dye. (Process also claimed.) N-Phenyl dimethyl 2-amino 4.8-disulfo 9-phenyl imino rosindulin. sym-Diphenyl 1.3-NAPHTHALENE DIAMIN 8-sulfo acid, or derivs., 1.5 mols., and 1 mol. dimethyl 4-amino DIPHENYLAMIN 2-sulfo are heated in amyl alc. at 100-130°. Homologs and derivs. claimed. Buivus acid dyes, fast to acids, alks., and rather fast to light. 603,013—Apr. 26, 1808. Philip Orr and Thilo Krorsrer, Germany. (Elberfeld.) Blue azin dye. (Process also claimed.) N-Phenyl ethyl 4/-sulfo benzyl 2-amino 8-sulfo g-phenyl imino rosindulin. sym-Diphenyl NAPHTHALENE DIAMIN 8-sulfo, or derivs., dissolved at 80° in abs. alc. containing sod. acetate and one mol. 4-nitroso ethyl 4’-sulfo benzyl aniL1In and more alcohol slowly added. BuveE acid dyes, fast to acids, alks. and somewhat fast to light. 606,295—June 28, 1808. Philip Orr and Thilo Krorser, Germany. (Elberfeld.) Blue-azin dye and process of making same. N-Phenyl phenyl 2-amino 3.8-disulfo 9-phenyl imino rosindulin. sym-Diphenyl 1.3-NAPHTHALENE DIAMIN 8-sulfo acid and 4-amino DIPHENYLAMIN 2-sulfo, 1 mol. each, dissolved in strong alc. containing sod. acetate heated at 82-85° and soln. of bichro- mate slowly added. Homologs and 6-sulfo derivs. are claimed, and other oxidizing agents. BuveE acid dyes, fast to acids, alks. and milling. 609,352—Aug. 16, 1808. Paul Junius, Germany. (Badische.) Blue dye. (Process also claimed.) Diethyl 2-amino oxy 8-sulfo rosindulin. Nitroso diethyl 3-amino PHENOL, or other, condensed in sixty per cent acetic acid at 100° with 1 mol. 1-NAPHTHYLAMIN 6- or 7-sulfo acid in presence of sod. acetate. BLug acid dye, fast to alks. 617,703—Jan. 10, 1899. Wilhelm Urrrserc and Henrich Hrimann, Germany. Blue safranin dye. (Process also claimed.) N-Phenyl dimethyl 2-amino 4’-dimethyl amino phenyl 9-imino rosindulin. Neutral Blue, derived from nitroso dimethyl ANILIN and phenyl 2-NAPHTHYLAMIN oF homologs, heated with 1 part bisulfite in 5 parts aq. at 100°, until brown color is pptd. and soln. nearly colorless, then 1.5 parts HCl added and again heated at 100°. Resulting 9-sulfo acid is dissolved in 10 parts alc. and 1.5 parts dimethyl 4-PHENYLENE DIAMIN added and boiled until SO, ceases to escape. Biux basic mordant dyes, fast to light and washing, adapted for printing. 66 DIGEST OF PATENTS 673,640—May 7, 1901. Arnold Hess, Germany. (H6chst.) Blue wool dye and process of making same. 1.5-Dinitro NAPHTHALENE heated in chlor sulfo acid soln. with H,S to 70-90° when vigorous reaction sets in and temp. rises to 130-140°. ‘Temp. is reduced and kept at 110-1209 for some hours while H,S is passed in. Biur and Gray acid and developed (CrO,) dyes, which when chromed are fast. 726,667—Apr. 28, 1903. Emil A. Fourngaux, New York City. (Metz.) Blue basie dye and process of making same. as-Dimethyl or diethyl PHENOSAFRANIN (Methylene Violet 3RA) derived by oxidation of dimethyl 4-PHENYLENE DIAMIN and ANILIN, diazotized with o.5 mol. NaNO,, soln. nearly or quite neut. with NaOH and let stand 1 day. Soln. is made acid with acetic, boiled, and dye pptd. by ZnCl, and NaCl. Brug basic dye. 872,815—Dec. 3, 1907. Heinrich Heimann, Germany. (Berlin.) Safranin dye and process of making same. 4’-Sulfo N-phenyl ethyl 4”-sulfo benzyl 2-amino 4”’-amino 2”’-sulfo phenyl 7-imino phenazin. 4-Nitro 4'/-amino DIPHENYLAMIN 2-sulfo, Na salt, and ethyl 4’-sulfo benzyl aniiin, Na salt, in aq. soln. are treated with soln. of bichromate and HCl and when InpAMIN has formed more bichromate and suLFANILIC acid are added and the mixture warmed till clear red-violet color. Resulting nitro comp. is reduced in HCl soln. by Fe to amino deriv. shown by blue color. . BuvE acid dye. 900,302—Oct. 6, 1908. Adriano Ostrocovicu, Roumania, and Theophile SILBeERMANN, Germany. Process of producing indulin colors. Producing indulins by use of halogen instead of acid for condensation. ANILIN and iodin, equal parts, are mixed and as temp. rises to 70° heat is applied, at 100° mass thickens and at 140° crystallizes. At 180° reaction ceases, but temp. is maintained for short time. When chlorine is halogen used, several methods may be employed. PbO, and anilin HCl or di-iodo ethylene, etc., may also be used. S. 697—‘‘Fast Blue, sp. sol.’”’ or “Indulin, sp. sol.’ 940,354—Nov. 16, 1909. Philip Orr, Germany. (Bayer.) Azin dye and process of making same. N-Phenyl 4’-amino sulfo phenyl 2-amino 3-methoxy 8-sulfo 9-phenyl imino rosindulin. sym-Diphenyl 1.3-NAPHTHALENE DIAMIN 8-sulfo acid, isomers or homologs, and 4-amino 2’- methoxy amino DIPHENYLAMIN sulfo, 1 mol. each in alc. soln. containing Na,CO,, heated to 30- 50° with ammoniacal CuSO, while air is passed through. Other para diamins and naphthalene 1.3-diamins can be used and sulfonation may take place after oxidation to azin. BLukr to VIOLET acid dyes. Note 603,013 and 606,295. 1,015,354—Jan. 23, 1012. Otto Soust, Germany. (Hoéchst.) Trisulfonic acid of the safranin series and process of making same. 4’-Sulfo N-phenyl 4-sulfo benzyl ethyl 3-amino 4”’-ethoxy 6-imino phenazin. 4’-Tolyl 4-PHENYLENE pIAMIN sulfo acid, homologs or derivs., and ethyl benzyl METANILIC acid, Na salt, in dil. Na,CO, soln., cooled to 5° and bichromate with HCl and acetic acid added, neut. with chalk and then boiled with suLFANILIc acid and more bichromate. Other sulfo acids of primary and tertiary amins with free para positions, are claimed. BuLiuer acid dyes for wool, that leave intermixed cotton fibers white. 1,174,820—Mar. 7, 1916. - Rudolf Burcxuarpt, Switzerland. - (Durand.) Basic yellow-red dyestuffs of the safranin series and process of making same. N-Ethyl 6-ethyl tolazin. Nitroso ethyl 2-roLuripIn condensed with ethyl 3-ToLUYLENE DIAMIN by boiling in alc. HCl soln. Other components claimed. Orange-rEep direct or basic mordant dyes, suitable for printing. 1,340,696—May 18, 1920. Andrea ANGEL, dec’d., England, by Mary L. ANGEL. Dyestuffs and process of making same. Parazin or benzenoid quinonoid dyes of new heterocyclic grouping of atoms. 4-Chlor ANILIN, or 1.4-halogen amino naphthalene or anthracene comps. or derivs. heated at 200° with condensing agent such as ZnCl, FeCl,, AICl,, P,O;, etc., to a dihydro parazin which is oxidized to a parazin. Auxochrome groups can be introduced and special dyes produced. VARI-COLORED acid and basic dyes. GROUP VI.—AZO 67 Group VI.—AZO. In the abstracts for Azo dyes the line giving the composition of the final product has been omitted, since this would be a repetition of the abstract itself. The word coupled is used as an abbreviation for diazotized and coupled. Combining weights are in the proportion of mol to mol, unless otherwise specified. 204,799—June 11, 1878. Re. 9,144—April 6, 1880. Heinrich Caro, Germany. (Badische.) Dye-stuff or coloring-matter. NAPHTHYLAMIN coupled with 1- or 2-NAPHTHOL, then sulfonated or not, or either component may be sulfonated before coupling. Three methods of producing naphthylamin sulfo acids are given. Dark brown powds. strong organic acids, sol. conc. H,SO, (VB); rep acid dyes. S. ros—‘‘Sudan Brown” and S. 106, 111, 160-2, 166. 210,054—June 10, 1878. F. X. Roussin, France. (Poirrier.) Improvement in coloring-matters derived from aniline and its homologs. SULFANILIC acid coupled with 1-NAPHTHOL, 2-napthol, resorcin, diphenylamin, or other phenol, amid, amin, or sulfo acid of same. RED, ORANGE, or YELLOW acid dyes. S. 136—‘‘Helianthin,” S. 139 “Orange IV,” 143, 144, 145, etc. : 210,233—Nov. 26, 1878. Re. 9,986—Dec. 27, 1881. Heinrich Baum, Germany. (Hoéchst.) Coloring-matter or dye-stuff. : Xyiipin coupled with 2-naPHtTHOoL 3.6-disulfo. A red powd., easily sol. aq., sol. conc. H,SO, (YR), diff. sol. alc. (YR), gives usual azo separation when reduced with Sn and HCl; an orange RED acid dye. S. 82—‘‘Ponceau 2 R.”’ Note Re 9,987 for making and separating “‘R’’? from “G’’ salts. 210,233—Nov. 26, 1878. Re. 9,987—Dec. 27, 1881. Heinrich Baum, Germany. (Hochst.) Coloring-matter or dye-stuff. XYLIDIN coupled with 2-NaAPHTHOL 6.8-disulfo, which acid is more soluble in alcohol and is thus separated from the insol. ‘‘R” salt. An orange red powd., freely sol. aq., sol. H,SO, (OR) and in HNO, (Y), diff. sol. alc. (OR), aq. soln., pptd. white by Br., sol. in excess; an orange RED acid dye. 211,180—Jan. 7, 1879. Alcide F. Porrrier, Daniel A. RosENsSTIEHL, and Zacharie Rovussin, France. Improvement in colors from crude naphthylamine. PHTALAMIN and sulfo derivs. coupled with 2-NAPHTHOL, phenols, amins, and sulfo derivs. Phtalamin accompanies crude naphthylamin among the liquid products, its sulfo deriv. being more easily aq. sol. Dyes miy be further transformed by action of heat with aq. and alk. into different coloring matters. They are RED (orseille) acid dyes. 211,525—Jan. 21, 1879. Zacharie Roussin and Alcide F. Porrrier, France. Improvement in colors derived from nitraniline. NITRANILIN*® and similar nitro naphthylamin, toluidin, or xylidin compounds coupled with NAPHTHIONIC acid, phenic acid, resorcin, phenylenediamin, 1- and 2-naphthols, amins, amids, phenols and sulfo comps. of same. YELLOW to RED acid or developed dyes, some sol. in aq., others insol. S. 52, etc.—‘‘Archil Substitute V.’’ *Obtained by action of alkalies on ‘‘nitrous acetanilid.” 211,671—Jan. 28, 1879. Zacharie Roussin and Alcide F. Porrrisr, France. Improvment in colors derived from toluidine and xylidine. TOLUIDIN, XYLIDIN or sulfo deriv. coupled with 1-NAPHTHOL, 2-NAPHTHOL, DIPHENYLAMIN, OF other amin, amid, phenol or sulfo deriv. sulfonated before or after coupling. RED, ORANGE, or YELLOW acid dyes. byl S. zo—“‘Brill. Orange O,” and S. 76 “Sudan II,” etc. 213,563—Mar. 25, 1870. John P. Grikss, England. (Badische.) Improvement in coloring-matters. ANIsipIn coupled with 1- or 2-NAPHTHOL disulfo (preferably beta). A red brown cryst. powd., sol. in aq. (R), and alc. (O), insol. in hydrocarbons, with alk. more yellow, with acids. 68 DIGEST OF PATENTS more violet, sol. conc. H,SO, (V), decomp. on acid reduction into two amins; a RED acid or acid mordant. (Al) dye. S. 95—‘‘Azo-Cochineal.” 213,564—Mar. 25, 1879. John P. Grisss, England. (Badische.) Improvement in coloring-matters. ANIsIDIN coupled with 2-NAPHTHOL sulfo, or other. A dark red cryst. powd., sol. in aq. and alc. (R), insol. hydrocarbon, soln. with alk. more yellow, with acid more violet, sol. conc. H,SO, (V), decomp. by acid reduction, giving anisidin, etc.; a RED acid or acid mordant (zinc aluminate) dye. Near S. 94—‘‘Azo Eosin G.” 221,114—Oct. 28, 1879. James H. Sressins, Jr., New York. Improvement in colors from diazo-benzole nitrate and pyrogallol. Aniuin coupled with pyrocaLLoL in alk. soln. Dye is sol. in alc. and benzene, very readily sol. in acetic acid, insol. in aq. except as alk. or sulfo salt; a yellow BRowN direct or basic mordant (tannin) dye. “Pyrogallidine.” 221,115—Oct. 28, 18709. James H. Sressins, Jr., New York. Improvement in colors from picric acid. ANILIN coupled with Picric acid in dil. alc. soln. Dark orange crysts., easily sol. alc. ether, and dil. HCl, as free acid is inso]l. in aqg.; an orange YELLOW direct or light YELLOW basic mordant (tannin) dye. “Picridine.”’ 221,116—Oct. 28, 1870. James H. Sressins, Jr., New York. Improvement in coloring-matters obtained from diamido-naphthaline and diazo-naphthaline nitrate. NAPHTHALENE dinitrated in fuming HNO,, pptd. by diln., filt., dissolved in hot glacial acetic acid and cooled to separate the alpha dinitro product. This is reduced by Sn and HCl and freed from Sn by H,S, free diamino naphthalene being separated from soln. by heating with NaHCO,, which is coupled in alc. soln. with diazo naphthylamin nitrate. Browwn cryst. powd., upon recrystn. gives dark red star shaped crysts. easily sol. alc. and conc. H,SO, (deep B), slightly sol. aq.; BROWN acid and VIOLET (Sn) or BLACK (Fe) acid mordant dyes. 221,117—Oct. 28, 1879. James H. Sressins, Jr.. New York. Improvement in coloring-matters obtained from cresol. ANILIN coupled with crEsoL in alk. soln., sulfonated before or after coupling. Brown crysts., easily sol. alc. (Y), insol. aq. as free acid, K salt sol. in boiling aq.; a YELLow direct Or ORANGE acid mordant (Sn) dye. “Cresolidine.” 221,118—Oct. 28, 18709. James H. Sressins, Jr., New York. Improvement in coloring-matters obtained from salicylic acid. ANILIN coupled in alc. soln. with saticytic acid. Brown cryst. powd., easily sol. alc., sparingly sol. aq. as free acid, but sol. as Na salt or sulfo deriv.; an orange RED direct pale orange RED basic mordant or RED acid mordant (Sn) dye for silk or wool. 221,119—Oct. 28, 1879. James H. Sresgins, Jr., New York. Improvement in coloring-matters obtained from naphthylamine and diazo- benzole nitrate. ANILIN coupled in alc. soln. with NAPHTHYLAMIN. Brown crysts., easily sol. cold alc., insol. in aq. as free acid, as K salt sparingly sol. aq., very sol. alc., easily sol. glac. acetic; a dark BROWN (silk), orange RED (cotton) or RED (wool) direct dye. ‘‘Naphthylamidine.” 221,120—Oct. 28, 1879. James H. Sressins, Jr., New York. Improvement in coloring-matters derived from toluol. ANILIN coupled in alc. soln. with TOLUYLENE DIAMIN. Orange cryst. powd., easily sol. boiling aq. or alc. (O), aq. soln. with HCl gives blood red crysts. of hydrochloride which are dine ae Sey J er ped. May O Luba. ee +s GROUP VI.—AZO 69 sol. in aq. and alc.; an ORANGE acid dye or acid mordant (lead oleate or zinc aluminate) dye for cotton. S. 34—“Chrysoidin R.” 224,927—Feb. 24, 1880. F. Kouuer, Germany. (Badische.) Dye-stufi or coloring-matter. Amino azo BENZENE mono sulfonated in 4 parts fuming H,SO, (twenty to twenty-five per cent SO,) at 60° then coupled with NaPpHTHOL disulfo in alk. soln. A brownish paste, sol. hot aq.; a RED acid dye. Called in patent ‘‘Fast Crimson, bluish shade.’’ Near S. 248—‘“Fast Scarlet B.” S. 247—‘‘Double Scarlet.” Schulz’ dye has two sulfo groups attached to the first component. Note 224,928. 224,928—Feb. 24, 1880. F. Kouier, Germany. (Badische.) Dye-stuff or coloring-matter. Amino azo BENZENE sulfo coupled with 2-NAPHTHOL. A brownish paste, sol. in hot aq.; a RED acid dye, suitable for printing. S. 247—“‘Double Scarlet.”? Note 224,927 and S. 246, ‘‘Cloth Scarlet G’’ have one sulfo group and S. 247, two sulfo groups in first component, while above has none. Called ‘‘Fast Crimson’’ in patent. 225,908—Mar. 23, 1880. F. X. Roussin, France. (Poirrier.) Artificial coloring-matter. (Process also claimed.) NAPHTHIONIC acid coupled with suLFANILIC acid, with other amins, amids, or phenols, their salts and sulfo acids except 1 or 2-naphthol and dioxy naphthalene (claimed in other patents), sulfonated before or after coupling. YELLOW to ORANGE to RED acid dyes. 233,465—Oct. 19, 1880. H. Baum, Germany. (Hochst.) Red coloring-matter. Amino azo BENZENE coupled with 2-NAPHTHOL 3.6-disulfo acid in NH, soln. Product may be sulfonated. A RED acid dye, fast to washing and light. Near 227—“Brilliant Crocein M.” Note 210,233 for disulfo acid mfr. 242,707—June 7, 1881. J. H. Srespins, Jr., New York. Azo color. ANILIN and NAPHTHYLAMIN mixture coupled 2-NAPHTHOL sulfo. Red brown crysts., easily sol. aq., sol. conc. H,SO, (V), aq. soln. with strong alk. KMnO, turns (YG), with Br aq. is decol.; a RED acid dye, fast to soap and light. 246,221—Aug. 23, 1881. J. ScuuncKE, Bavaria. (Badische.) Azo color. Amino azo XYLENE coupled with 2-NAPHTHOL disulfo. in alk. soln. A black powd. of green metallic luster; a violet RED (archil or garnet) acid dye. S. 238—“‘Union Fast Claret.” 246,272—Aug. 23, 1881. H. Baum, Germany. (Hochst.) Azo coloring-matter. Amino azo BENZENE sulfo coupled with 2-NAPHTHOL, sulfo (from 2-naphthol sulfonated in 3 parts conc. H,SO,, at 25°), in alk. soln., preferably NH,. Product is freely sol. in aq. and dil. mineral acids, sol. conc. H,SO, (B), thus differing from 2-naphthol disulfo (V) or 2-naphthol deriv. (G), aq. soln. with alum gives no ppt.; a RED acid dye for wool and acid mordant (Al) dye for cotton. 249,926—Nov. 22, 1881. J. H. O. Gurxr, Germany. (Hoéchst.) Coloring-matter. (Process also claimed.) 4-Amino cINNAMIC acid, methyl ester, coupled with 2-NAPHTHOL 3.6-disulfo. —‘“Naphthol Black 6B” and S. 272—‘‘Naphthol Black B.” 354,746—Dec. 21, 1886. L. Scuap, Germany. Production of coloring-matter. Amino azo BENZENE disulfo, coupled with 4-tolyl 2-NAPHTHYLAMIN. A blue BLAcK direct dye. The working of patent is so obscure that it is difficult to determine whether a mono or disazo dye is described. ‘The color indicates disazo. 356,672—Jan. 25, 1887. H. Voiisrecut and C. Menscuince, New York. (Schoellkopf.) Red coloring-matter from alpha diazo beta-naphthylamine sulphonie acid. I-NAPHTHYLAMIN 5-Sulfo coupled with 2-NAPpHTHOL in alk. soln. A Rep acid dye, more yellowish shade than “Rocelline” which is made from Piria’s naphthionic acid. Rocelline is sol. in conc. H,SO, (B), while new dye is (RV). “Brilliant Red.” 357,273—Feb. 8, 1887. C. Duisserc, Germany. Blue coloring-matter from tetrazodiphenyl. (Process also claimed.) DIANISIDIN (by reduction of NITRANISOL and treatment with conc. acid) coupled with 2 mols. 1-NAPHTHOL 4-sulfo. A black powd. with bronze hue, easily sol. aq. (VB), sol. in alk. (R), sol. conc. H,SO, (deep B); a deep siue direct dye, fast to warm soap and mineral acids. S. 411—‘“‘Benzo Azurin 3G.” Note 213,563-4, 481,054, and 357,274. 357,274—Feb. 8, 1887. C. Duiszerc, Germany. Red coloring-matter for dyeing by the action of tetrazo dyes with beta- naphthylamine sulpho acid. (Process also claimed.) DIANISIDIN, coupled in organic acid soln. with 2 mols. 2-NAPHTHYLAMIN sulfo. A red powd., easily sol. hot aq., insol. in alc., sol, conc. H,SO, (B), decomp. on reduction; a deep BLUE (strong acid bath) to violet RED (alk. bath of phosphate or carbonate) direct dye, fast to dil. acids and alk. Near S. 405—‘‘Benzopurpurin, 10B.” Isomer of Benzopurpurin, which is the 1-naph- thylamin sulfo product. 358,865—Mar. 8, 1887. C. A. Martius, Germany. Production of mixed azo coloring-matter. BENZIDIN, TOLIDIN, or other diamin, coupled with 1-NAPutHoL sulfo, then with 1I-NAPH- THYLAMIN sulfo. The second coupling agent may or may not be the same as the first, a long list of different components being given in six classes. VARI-cOLORED direct dyes. S. 312—‘‘Congo Corinth S$.” Note 344,971. 359,57 6—Mar. 15, 1887. A. Romer, Germany. (Badische.) Manufacture of red coloring-matter. I-NAPHTHALENE DIAMIN diazotized in presence of large excess HCl, coupled with 2 mols. NAPHTHIONIC acid in organic acid soln. Tests for end of reaction and for diamin in reduced dye to distinguish same from benzidin, etc., are given. Dye soln. with conc. HCl ppts. (dull YG), while Congo Red and Benzopurpurin ppt. (B); decomp. by Zn dust, amin extracted in CS, and Br added gives (RT), while other two dyes are (intense B); a rep direct dye. Near S. 432—‘‘Diamin Catechu.” ae Re ee ee ee etre. ee GROUP VI.—AZO 77 360,792—Apr. 5, 1887. F. Benper and G Scuuitz, Germany. (Leonhardt.) Obtaining diazo colors by means of diamido-stilbene and diamido-fluorene. Diamino STILBENE or diamino FLUORENE tetrazotized and coupled with 2 mols. of an amin, a phenol, their sulfonates or carbonates, or with two different mols. of an amin or phenol, etc. Lists of these are given. VARI-coLORED direct dyes. 361,404—Apr. 19, 1887. Paul FrrepLAENDER, Germany. (Oehler). Combination of tetrazodiphenyl chlorire with resorein. (Process and product claimed.) BENZIDIN, tolidin, etc., coupled with 2 mols. RESoRcINoL in alk. carb. soln. A red brown cryst. pwd., diff. sol. aq. (BrR), aq. soln. turns red with NaOH and is pptd. (Br) by acids; a direct RED dye. S. 317—‘“Pyramidol Brown BG.” Schulz states that by coupling with diazo solns. a brown color is produced. 3862,813—May 10, 1887. Friedrich Bayrer, Germany. (Bayer.) Yellow-red dye-stuff from tetrazo-diphenyl. (Product.) BenzipIn coupled in organic acid soln. with 2-NAPHTHYLAMIN 7-sulfo (Bayer’s or d-acid). A red pwd, easily sol. hot aq., soln. not changed by acetic acid, pptd. by HCl (Br), sol. conc. H,SO, (B); an orange rep direct dye. Note 363,502. 363,502—May 24, 1887. Friedrich Bayer, Germany. (Bayer.) Manufacture of dye-stuffs and coloring-matter. ToLIDIN coupled in organic acid soln. with 2 mols, 2-NAPHTHYLAMIN 7-sulfo (delta acid.) A brown red pwd. easily sol. in aq., sol. with HCl ppts. free dye acid (Br), sol. conc. H,SO, (B); a violet rEp direct dye, fast to acetic acid. S. 367—‘“Diamin Red 3 B.’’ Schulz credits this dye to Weinberg, 1886. Note 362,813. 365,409—June 26, 1887. Joseph Rouner, Switzerland. (Basle.) Production of new coloring-matter. (Product, not process, claimed.) Amino AZO BENZENE or other amino azo comp., coupled with 3-TOLUYILENE DIAMIN or 3- PHENYLENE DIAMIN. Products are diff. sol. aq.; BROWN to brown vIOoLET direct dyes. 365,666—June 28, 1887. Paul Borrricrer, Russia. (Berlin.) Manufacture of new red dye-stuffs or coloring-matters. Benzipin coupled with 2 mols. 1- or 2-NAPHTHYLAMIN or their sulfo acids, or mixtures thereof. Dye may be mono- or di-sulfonated after coupling, with conc. H,SO,, the anhydride, or monochlorhydrin. Rep direct dyes. 365,667—June 28, 1887. Paul Borricer, Germany. (Berlin.) Combination of the salts of tetrazo-diphenyl and the naphthylamines,. BENz1pIN coupled with 2 mols. 1- or 2-NAPHTHYLAMIN, NAPHTHIONIC acid or other sulfo acids. Rep direct dyes. S. 307—“‘Congo Red.” Note 365,666 for process. 366,078—July 5, 1887. Carl Duisserc, Germany. (Bayer.) Manufacture of dye-stuffs or coloring-matters. 2- or 4-TOLIDIN coupled with 2 mols. 1-NAPHTHOL 4-sulfo. A black pwd., easily sol. hot aq., (RV), conc. soln. pptd. by mineral acids (RV), diff. sol. alc. and glac, acetic (VR), insol. conc. NaOH, easily sol. dil. NaOH or twenty per cent NH, (R), Sol. conc. H,SO, (B); a violet BLUE direct dye (alk. bath with silicate or phosphate of Na), fast to mineral acids. S$. 377—“‘Azo Blue.” 375,848—Jan. 3, 1888. A. WEINBERG and H. Sigepert, Germany. (Cassella.) Manufacture of dye-stufis. TouipIn coupled with 2 mols. I1-NAPHTHYLAMIN sulfo in presence of excess Na acetate or carbonate. A red pwd., easily sol. in aq., sol. conc. H,SO, (B) turning brown on diln; a rp direct dye, fast to alk. and weak acids, and of good covering power. S. 367—“‘Diamin Red 3B.” Dye is isomeric with 329,635 (Duisberg). 78 DIGEST OF PATENTS 375,930—Jan. 3, 1888. P. FRIEDLAENDER and B. Priress, Germany. (Oehbler.) Production of orange azo dye-stuffts. (Product also claimed.) ToLipIN coupled with 1 mol. each of 3-TOLUYLENE DIAMIN sulfo and gsaLicyLic acid in alk. soln. A red brown pwd., easily sol. hot aq. (O), insol. in hydrocarbons, soln. pptd. by acids (BrR), sol. conc. H,SO, (V); an orANGE direct dye, fast to soap and dil. mineral acids. Near S. 592—‘‘Toluylene Orange G.”’ 376,392—Jan. 10, 1888. Adelbert Myutins, Switzerland. (Geigy.) Production of a new red azo color. 4-NITRANILIN coupled with 1-NAPHTHYLAMIN 4.7- or 4.6-disulfo; a RED acid dye. S. 54—‘‘Apollo Red B.” 380,067—Mar. 27, 1888. A. WEINBERG, Germany. (Cassella.) Production of new diamid compounds and of azo colors produced therefrom. 2-Ethoxy BENZIDIN, or other ethers of oxy diphenyl comps., coupled with 2 mols. SALICYLIC acid, or 1 mol. each of two amins, phenols, or sulfo or carboxyl derivs. thereof. YELLOW, RED, BLUE Or VIOLET direct dyes. S. 401—‘“‘Diamin Blue 3R.” S. 404—‘‘Diamin Yellow N.” 380,098—Mar. 27, 1888. T. DieHL, Germany. (Zimmer.) Coloring-matter from the sulpho-acids of ethyl or diphenylamine combined with tetradiphenyl or tetrazoditolyl. (Process, not product, claitned.) BENZIDIN, TOLIDIN, or similar comp., coupled with 2 mols. ethyl ANn1ILIN sulfo or other sulfo acids of ethyl anilin or diphenylamin, in acetic soln. or with 1 mol. above and 1 of an amin, phenol, salicylic acid, phenol or naphthol or naphthylamin sulfo acid. YELLOW to RED to VIOLET direct dyes, of fiery tint and fast. 380,402—Apr. 3, 1888. L. Paut, Germany. Production of disuipho and dicarbo acids of the diamidoazo-benzidines. (Product claimed.) 3.3’-Diamino DIPHENYL 4.4/-dicarbo acids, coupled with 2 mols. 1- or 2-NAPHTHYLAMIN, OF with 1 mol. each of two coupling agents, again tetrazotized and coupled with 2 mols. 2-NAPHTHOL 3-6-disulfo, or other. Or tetrazo comp. coupled with one mol. coupling agent, then boiled in dil. acid to give hydroxyl comp. Very long and complex claims. Vari-coLorEp direct dyes. 380,403—Apr. 3, 1888. L. Paut, Germany. Production of disulpho and dicarbo acids of the diamidoazo-benzidines. BENZIDIN, TOLIDIN, or diamino dixylyl, coupled in organic acid alc. soln. with METANILIC acid, then in alc. alk. carb. soln. with another mol. of same. Other anilin sulfo acids, amino benzoic acids, toluidin or xylidin sulfo acids as second components are claimed. YELLOW, RED to BROWN direct dyes. Note 358,865 (Martius) for same components combined in aq. soln., which yields mono azo only. Patent claims different product in alk. soln. giving reason and tests, “not a disazo compound.” 380,927—Apr. 10, 1888. A. F. Porrrier and D. A. RosEenstTigHL, France. (Soc. Chim.) Production of azo colors. (Product claimed.) . 3-NITRANILIN, 3- OF 4-nitro toluidin (m.p. 107° and 78°), nitro-xylidin, (m.p. 123°), or other nitro aromatic amin, reduced in dil. NaOH with Zn powd. at a boil, separated, tetrazotized, and coupled with 2 mols. 1-NAPHTHOL 5-sulfo ‘‘Piria’ or other phenol, oxyphenol, naphthol, oxynaphthol, primary, secondary or tertiary amins diamins, and alkyl., sulfo and carboxyl derivs. of these. Long list given. Soluble vari-coLorEp direct and acid mordant dyes. 380,92S—Apr. 10, 1888. A. F. Porrrrer and Z. Roussin, France. (St. Denis.) Production of diazoic coloring matters. (Product claimed.) 4-NITRANILIN, nitro toluidin, or nitro xylidin, coupled with Witts (Ber. 79, 578) 1-NAPHTHY- LAMIN sulfo in acid soln., or with other isomer of naphthionic acid. YELLOW, RED, to BROWN acid dyes. S. 55—‘‘Archil Substitute 3VN.” Se ee a ee ae GROUP VI.—AzO 79 381,045—Apr. to, 1888. O. N. Wirt, Germany. (Badische.) Manufacture of purple-black azo dye-stuff. (Product, not process, claimed.) @S-DINITRANILIN (Gottlieb), coupled with 2-NAPHTHYLAMIN sulfo, (Brénner) in acetic acid soln., or with delta sulfo acid, but not other isomer. —“‘Wool Violet S.’’ 525,657—Sept. 4, 1894. P. Jurius, Germany. (Badische.) Azo dye. 4-NITRANILIN coupled with dimethyl mxEraniiic acid, or diethyl comp. —“‘Diamin Rose R,” S. 418—‘“‘Brill Blue C.”? Addition to 592,125. 536,431—Mar. 26, 1805. M. Kaun and F. Runxet, Germany. (Bayer.) Black dye. (Process also claimed.) 4.4’-Diamino DIPHENYLAMIN 2’-sulfo coupled in alk. soln. with 2-AMINO 8-NAPHTHOL 6-sulfo “G,” tetrazotized and coupled with 2 mols. 3-PHENYLENE DIAMIN, or other. A BLACK direct dye, fast to acids, alks. 536,532—Mar. 26, 1895. R. KircuHHorr, Germany. (Derlin.) Blue azo dye. 4-NITRANILIN coupled with 2-amino 4-crRESOL, methyl ether, (OH=1), reduced with alk. sulfid, tetrazotized and coupled in alk. soln. with 2 mols. 2-AMINO 8-NAPHTHOL 6-sulfo ‘‘Gamma.” A BLUE to BLACK direct and developed dye, can be coupled on fiber to deeper and faster shades. 536,878—Apr. 2, 1895. R. KircHuoFFr, Germany. (Berlin.) Black dye. 4-NITRANILIN coupled with 2-amino 4-cRESOL, methyl ether, reduced to diamino comp. by alk. sulfids, tetrazotized and coupled with saLticy1ic acid, and 2-AMINO 8-NAPHTHOL 6-sulfo. S. 353—‘‘Direct Indigo Blue BN” and S. 439—‘‘Direct Indigo Blue A.’’ Note 536,879-80. Schulz gives above pat. under S. 353, but there is no apparent connection, one being a tris-, the other a disazo dye. See 557,438 for same Schulz number. 536,879—Apr. 2, 1895. R. Kircuuorr, Germany. (Berlin.) Blue-black dye. 4-NITRANILIN coupled with 2-amino 4-crEsoL, methyl ether (OH=1) reduced then tetrazotized and coupled with 1-NAPHTHYLAMIN 6- or 7-sulfo and 2-AMINO 8-NAPHTHOL 6-sulfo “G.” A BLACK to violet GRAY direct and developed dye, can be developed on fiber. Note 536,880 and 536,878. 536,880—Apr. 2, 1895. R. KircHuorr, Germany. (Berlin.) Blue dye. 4-NITRANILIN coupled with 2-AMINO 4-CRESOL, methyl ether, (OH=1) reduced then tetrazotized and coupled with 2 mols. of 2-AMINO 8-NAPHTHOL 6-sulfo. Note 536,878 and 536,879. 102 DIGEST OF PATENTS 539,699—May 21, 1805. M. MoeE.ier, Germany. (Berlin.) Blue dye. (Process also claimed.) BENzIDIN coupled in alk. soln. with 2 mols. 1-aMINO 8-NAPHTHOL 2.4-disulfo or with 1 mol.. each of this and of a phenol, amin, sulfo or carbo acid. A sBiug direct and acid dye. Note Ser. 466,691 for original claim. 541,750—June 25, 1895. W. Herzperc and O. Weser, Germany. (Berlin.) Black dye. I-AMINO 8-NAPHTHOL 3.6-disulfo disazo di-anin1In coupled in alk. soln. with 2 mols. 3- TOLUYLENE DIAMIN, or Other. 541,859—July 2, 18905. R. Korerr, Hungary. (Kinzlberger.) New amido base and colors therefrom. (Process also claimed.) 2.2/-TOLIDIN, 2.2/-dianisidin, 1-naphthylamin, 2-toluidin or other primary amin or diamin condensed with FORMALDEHYDE in conc. H,SO, to form new base with amino groups intact. Products are non cryst., (m.p.'60°), sol. in ether, with acids give ppts. (white), readily form diazo to tetrazo comps. to give VARI-COLORED acid and direct dyes. Note 542,073 (Brack). Dyes are not claimed except in title of patent. 542,022—July 2, 18095. EK. Lauser and L. Caserti, Italy. (Bayer.) Process of dyeing. (Product also claimed.) Any antimonious salt, such as the double fluoride (SbF,NaF) is pptd., with sufficient alk. carb. as Sb (OH),,* the latter mixed with glycerin or other diluent, then with the Na salt of 2-NAPHTHOL and with dil. NaOH to a thick liquid which is applied to the fiber, and a diazo comp. is allowed to react upon the fiber. Vari-coLorED developed dyes are produced. *Antimonious oxide preserves the 2-naphthol from decomposition for a long time. §42,073—July 2, 1895. J. J. Brack, Switzerland. (Durand.) Substantive cotton dye. (Process also claimed.) Base derived from DIANISIDIN and FORMALDEHYDE coupled in alk. soln. with 2 mols. 1- AMINO 8-NAPHTHOL 3.6-disulfo or other. A GRAy to BLACK direct dye. Note 541,859 for comp. condensed differently (Koreff). 543,212—July 23, 1895. R. Korerr, Hungary. Azo dye. (Process also claimed.) Tetra amino DITOLIDINO methane, obtained by condensing 2-tolidin and formaldehyde, coupled with 4 mols. NAPHTHIONIC acid, or other. A RED, VIOLET or BLACK direct dye. Differences from Brack condensation noted. 543,539—July 30, 1805. K. Patrue and A. IsragL, Germany. (Bayer.) Brown azo dye. (Process also claimed.) Dehydro thio totumpin sulfo coupled in acetic soln. with I-NAPHTHYLAMIN 6-sulfo, separated, re-diazotized and coupled with PHENOL, and purified product alkylated by heating in alk. fifty per cent alcohol at 100° in closed vessel with EtHyL bromide. Other components claimed. A yellow-Brown direct dye, fast to light, alk., and acid. 543,747—July 30, 1895. M. Moe.ier and Carl OE£LscHLAEGEL, Germany. (Berlin.) Black azo dye. I-NAPHTHYLAMIN coupled in alk. soln. with 1-AmINo 8-NAPHTHOL 4-sulfo acid No. II, made acid with acetic and combined with diazo sunFANILIc acid. A BLAcK acid dye. Note isomeric dye from 1.8.5-acid (acid No. I) in 324,665. (Biilow). See also 543,748. 543,748—July 30, 1895. M. Moexi.er and Carl OriscHLarceL, Germany. (Berlin.) Black azo dye. r I-NAPHTHYLAMIN coupled in alk. soln. with 1-AmiINo 8-NAPHTHOL 4-sulfo then combined in acetic soln. with diazo I-NAPHTHYLAMIN and with diazo sULFANILIC acid, one mol. each. The first coupling may also be in acid soln. A BLacxk direct dye. Addition to 543,747. Ay GROUP VI.—AZO 103 544,699—Aug. 20, 1805. M. Uxricu and J. BamMmMann, Germany. (Bayer.) Blue dye and process of making same. Benzipin coupled in alk. soln. with 2 mols. 1-AMINO 8-NAPHTHOL 3.6-disulfo. A BLUE direct dye, fast to alks. S. 337—‘‘Diamin Blue BB.” Note 544,700. 544,700—Aug. 20, 1895. M. Uxricu and J. BammMann, Germany. (Bayer.) Blue dye and process of making same. ToLipIn, coupled in alk. soln. with 2 mols. 1-AMINO 8-NAPHTHOL 3.6-disulfo. A BLUE direct dye, fast to alk. Near S. 337—‘‘Diamin Blue BB.’ Addition to 544,699. 545,333—Aug. 27, 1895. H. A. BERNTHSEN, and P. Juzius, Germany. (Badische.) Azo orange dye. BENzIDIN disulfo, tetrazotized and coupled with 2 mols. of nitro 3-PHENYLENE DIAMIN, OF other. An ORANGE, direct dye, fast to acids, washing, and light. S. 360—‘‘Pyramin Orange R.” 546,068—Sept. 10, 1895. F. Krecxe and I. Rosenserc, Germany. (Kalle.) Blue-black disazo dye. (Process also claimed.) I-NAPHTHYLAMIN 3.6-disulfo coupled in alk. soln. with 1-NAPHTHYLAMIN 7-sulfo, rediazotized and coupled with 2-NAPHTHOL 3.6-disulfo. Other components claimed. A VIOLET, BLUE, to BLACK acid dye. S. 273—‘“‘Biebrich Patent Black 4 AN” etc. Note 546,069 and -7o. 546,069—Sept. 10, 1895. F. Krecke and I. Rosenserc, Germany. (Kalle.) Blue-black disazo dye. I-NAPHTHYLAMIN 3.6-disulfo coupled in alk. soln. with 1-NAPHTHYLAMIN 7-sulfo obtained by nitration and reduction of NAPHTHALENE 7-sulfo, rediazotized and coupled with 1-NAPHTHY- LAMIN. A blue BLAcK acid dye. S. 278—“Biebrich Patent Black.” Addition to 546,068. 546,070—Sept. 10, 1895. F. Krecxe and I. Rosensperc, Germany. (Kalle.) ‘Blue-black dye. Amino SALICyLIc acid coupled in alk. soln. with 1-NAPHTHYLAMIN 7-sulfo, rediazotized and coupled with 2-NAPHTHOL 3.6-disulfo. A blue BLacK acid mordant dye, fast to milling and light. S: 278—‘“‘Biebrich Patent Black.” Addition to 546,068. 548,416—Oct. 22, 1805. A. AsHwortH and J. Burcer, England. Brown dye. (Process also claimed.) I- Of 2-NAPHTHYLAMIN coupled in alk. carb. soln. with nitroso NAPHTHOL bisulfite comp. A Brown acid mordant (Cr) dye, suitable for printing. 548,460—Oct. 22, 18905. C. Ris, Switzerland. (Geigy.) Brown dye and process of making same. 4-Amino PHENOL or sulfo acids, coupled with PyRoGALLIc acid in alk. carb. soln. A BROWN acid mordant (Cr) dye, suitable for printing. S. 84—‘‘Azochromin” and S. 138—‘‘Chrome Brown RR.” 555,359—Feb. 25, 1806. H. A. BeRNTHSEN, and Paul Junius, Germany. (Badische.) Red dye and process of making same. Brenzip1n coupled with 1 mol. each of saticyLtic acid and 2-AMINO 5-NAPHTHOL 7-sulfo. When diazotized on fiber dyeing turns black and couples to dark shade. ) sod. acetate in alc. soln., or with (c) air in alk. aq. soln. to form brom indigo. Chlor or iod indoxyl by same process yields nonhalogenated indigo. Brom indigo is a blue powd., sol. in cold C,H,NH, or CS,; a BLUE vat dye giving shades redder and more brilliant than indigo. Reactions of indigo and four brom indigoes are tabulated in patent. Near S. 879—‘“‘Brom indigo.” Note 713,437 for brom indoxyl. 726,688—Apr. 28, 1903. Benno Homo.ixa, Germany. (Hochst.) Indigo mixture and process of making same. _ Indigo sulfo acid. 2-Nitro BENZALDEHYDE, or other ortho nitro aromatic aldehyde and acrToner condensed in dil, alkali to form 2-nitro phenyl @-lactic acid methyl ketone, 2 mols. of which mixed thor- oughly with at least 1 mol. of benzyl aniLiIn sulfo, sod. salt, or salts of other benzylated ar- omatic bases, are sol. in aq. and when made alk. yield indigo sulfo. Products are easily sol. in hot aq. and are stable. Near 877—“‘Indigo sulfo acid.” 7 27,270—May 5, 1903. Augustus BiscHLER, Switzerland. (Basle.) Process of making indoxyl. Indoxyl produced at low temp. Phenyl cGiycin, its carboxylic acid salts, or other, heated with 2 parts anhyd. KOH at 200° and o.7 part Na,O added, or three ingredients may be mixed cold and gradually heated. The caustic acts as flux and oxide, being more powerful dehydrating agent, causes reaction to take place at lower temp. S. 874—‘“Indigo.” 729,217—May 26, 1903. Arnold Rautyen, Germany. Process of making brom indigo. Mono or dihalogenated indigo. Indigo saturated with acids, organic or inorganic, or with CS,, to which 1 or 2 mols. bro- mine or chlorine in same solvent are added at moderate temp. Dibrom indigo has the appear- ance of indigo, soln. in H,SO, is yellow green, it sublimes, and may be sulfonated; it is a BLUE vat dye. S. 879—“Brom indigo.” Note 807,782 for similar dye by different and more detailed process. 730,148—June 2, 1903. Paul EF. Oserreit, Germany. (Badische.) Indigo coloring-matter containing halogen and process of making same. Dibrom indigo. Phenyl ciycocot 2-carbo or cyan methyl ANTHRANILIC acid mono brominated in glac. acetic acid, (ligroin, benzene or other), separated, and product boiled with alk. then with acetic an- hyd. The latter solvent is distilled off in vacuum, residue saponified with NaOH and oxidized with air. Dibrom indigo resembles indigo, is insol. in cold glac. acetic, CS, CHCl,, and hot alc., contains bromin, and is a BLUE vat dye of slightly redder shade than indigo. Near S. 879—‘“‘Brom indigo.” Note 662,754. 731,385—June 16, 1903. Paul E. Oserrert, Germany. (Badische.) Process of making indoxyl. Indoxyl and indoxylic acid with improved yield. Phenyl ciycin 2-carbo, disodium salt, in strong caustic alk. soln. evaporated dry in vacuum, 202 _ DIGEST OF PATENTS then heated above 200°. Mixed alkalies may be used in melt. The expensive and tedious op- eration of grinding ingredients together is avoided, and decomp. of glycin by evaporation in air. S. 874—“Indigo.” 737,836—Sept. 1, 1903. Willibald HentscHEL, Germany. (Heyden.) Process of making indoxyl and indigo preparations. Indoxyl and indigo with increased yield. ’ Phenyl ciycin, homologs or derivs. (esters, amids, anilids, etc.) heated with caustic alkalies and alk. alccholates, with or without alkali earths, to 100-250°, to form INDOXYL. S. 874—“Indigo.”’ 746,965—Dec. 15, 1903 Rudolf KnigrscH and Henry S. A. Hout, Germany. (Badische.) Process of making indoxyl and derivatives thereof. Indoxyl and indigo. 2-tolyl ctycin, K salt, or homologs, heated with 3 parts of an oxide of an alk. earth such as barium oxid at 290-300°. Strontium oxid gives less yield but both SrO and BaO produce more indoxyl than CaO. S. 874—“‘Indigo.” 756,171—Mar. 20, 1904. Rudolf Knirrscu, Paul SrrpEL and Georg. W. Meisrer, Germany. (Badische» \ Process of making indoxyl and derivatives. Indoxyl. Phenyl ciycin, K salt or other, heated at 250° without air, with an alk. oxide such as sod. oxide dil. with NaOH, KOH, CaO, SrO, BaO, or mixtures of these. Free alkali metal must not be present. Caustic may be converted to oxide by electrolysis or the oxide may be obtained by heating Na with Na,O, or K with KOH, S. 874—“Indigo.”’ 761,007—May 24, 1904. Paul E. Oxsrerreit, Germany. (Badische.) Chlorinated indigo and process of making same. __ 5.5'.7.7’-tetra chlor indigo, or di deriv. Phenyl ciycoco. 2-carbo or cyan methyl ANTHRANILIC acid, in glac. acetic, or other soln., to which 1 or 2 mols. chlorine are added. Anthranilic acid comp. then must be boiled in 15 per cent NaOH. Resulting mono or dichlor phenyl GLycocoL 2-carboxylic acid separated, acet- ylated, acetic anhyd. recovered by distn. in vacuum, product saponified in dil. NaOH and oxidized by air. S. 885—‘‘Brill. Indigo.” BASF /B. Note 662,754. 765,996—July 26, 1904. Albrecht Scumipt and Rudolf Mixier, Germany. (Héchst.) Manufacture of brominated indigo. (Product not claimed.) Brom indigo by elec- trolysis. Finely divided InpDIGO or indigo white mixed with HBr, 4o per cent, electrolyzed, with or without diaphragm, using carbon electrodes, current of 2.5 V. and 3 amp., to form mono or dibrom product according to amperage and time applied. Sulfuric acid, 20-80 per cent, con- taining HBr, may be used with a bromide present, or not. Strong acid solns. required. The composition of product is not known, but properties resemble those of brom indigo from dry bromination or by synthesis from indoxyl. A BLUE vat dye. 768,455-—Aug. 23, 1904. Benno Homo.xa and Friedrich von Bowzano, Germany. (Hochst.) Glycollie acid anilid-orthocarboxylic acid and process of making indigo. Indigo. : ANTHRANILIC acid and GLYCOLLID fused together at 180—200° to form GLycoLic acid anilid 2-carboxylic, Na salt, which fused in alkali at 240-300° yields leuco indigo. Glycolic acid an- ilid 2-carboxylic acid when purified forms colorless crysts., m.p. 167°, slightly sol. cold aq., very sol. hot aq., alc., ether and acetone. S. 874—‘Indigo.” 772,560—Oct. 18, 1904. Sylvain Ercuwart, France. (Soc. Chim.) Printing compound of orthonitrophenyl lIactoketone. 2-Nitro phenyl lacto ketone compound for indigo dyeing. 2-Nitro phenyl methyl LAcTO KETONE mixed with 3 parts 4-TOLUENE sulfo salt, or other ar- omatic or fatty sulfo acid or salt, or sulfonated oleic acid, Turkey red oil, esters thereof, etc. Se gg tne GROUP VII.—INDIGO AND INDIGOID 203 For printing pastes a thickener is added. Print or dye material, dry, and pass through 15 per cent NaOH. S. 874—“Indigo.” 772,775—Oct. 18, 1904. Wilhelm BEHAGHEL and Gustav C. Schumann, Germany. (Badische.) Process of making indoxylic compounds. Indoxylic compounds. Hydroxy ethyl ANILIN, or any aromatic amin containing a hydroxy ethyl group attached to the amino N, heated in autoclave at 280-290° with 3-4 parts caustic alkali. Lime sodium oxid, or sodamid may replace some of the caustic. S. 874—“Indigo.” 776,884—Dec. 6, 1904. Augustus BiscHLER, Switzerland. (Basle.) Process of making indoxyl. &e. Indoxyl. Phenyl cGiycin, or other aryl glycin, salts, homologs, or derivs., heated to 250° in alkali melt containing some alkali metal (Na), then ANILIN, ammonia, acetylene or other agent to re- move H,O is introduced and heating continued till reaction is complete. S. 874—‘“‘Indigo.”? Addition to 761,440. 778,725—Dec. 27, 1904. Daniel VorRLANDER, Bruno DrEescHER and Paul SemeLt, Germany. (Badische.) Aeylated indoxyl and process of making same, ' Acet-indoxyl. InpoxyL and 1npoxy.ic acid melt, or other, (from phenyl GLiycocoL 2-carbo acid and KOH) neut. with acid, then acetic anhyd., (benzoyl chloride, or other) added to form mono acetyl deriv., filt., and acet indoxyl separated from acet indoxylic acid by dissolving the latter in ice water. Acet indoxyl alone produced by boiling dil. alk. soln. of mixed melt and acetylating. S. 874—“Indigo.” Note 690,332 and 546,165. 778,752—Dec. 27, 1904. Rudolf Knigerscu, Paul SerpEer and Otto J. Graut, Germany. (Badische.) Process of making indigo. Improved yield of indigo from phenyl glycocol and derivs. Improvement consists in conducting melt under substantially anhydrous conditions. A mix- ture of mol. NaOH and KOH, as near water-free as possible, to which an alkali earth oxide is added in excess of that sufficient to combine with all the water in the melt, (1 part CaO to 3.6 parts alkali), is heated to 265° and phenyl cLycocot or deriv. added. Yield is about 50 per cent of theory and becomes greater as amount. of water present is reduced by more alkali earth oxide, the amount of which is limited by the difficulty in stirring the melt. S. 874—“‘Indigo.” Note 617,652 and 622,139. 798,077—Aug. 29, 1905. Paul SerpEL, Germany. (Badische.) Process of making indolic bodies. Indolic bodies as by-product in indigo mfr. Phenyl cLycin 2-carboxylic, or derivs., heated in alkali at 280-300° with or without re- ducing agents such as Fe powd. sulfites, etc., dild., oxidized, indigo removed by filtration, and indole recovered from soln. by ether, benzene by steam distn., or as picrate, etc. Higher temp. of melt and presence of reducing agents increase yield of indole. Addition to 794,049. 807,782—Dec. 10, 1905. Albrecht Scumipt, Germany. (Héchst.) Process of brominating indigo. Brominated indigoes (mono, di, tri, etc.) with least formation of isatin. Indigo in inorganic acid soln., subjected to the action of 1 mol. Br at ro-15° till Br is absorbed then cooled to O° and filt. More Br, with or without carrier, gives higher bromina- tion. Br may be produced by electrolysis, with or without diaphragm. Liberated HBr may be recovered. Acid solvents may be H,SO,, HCl, HBr, HF or H,PO. Stronger H,SO, than 78 per cent, or heat, results in sulfo indigo, while weaker acid than 50 per cent converts into bromisatin. S. 879—“‘Brom indigo Rathjen.” Note 729,217, for another process. 812,598—Feb. 13, 1906. Albrecht ScHMipt and Erich Kronuouiz, Germany. (Hochst.) Process of chlorinating indigo. Chlorinated indigo. Inpico white, or indigo, containing some dry hydrosulfite N. F. mixed in CCl,, CS,, or similar solvent, treated with sulfuryl chloride in amounts according to chlorination desired. 14 204 DIGEST OF PATENTS a Gaseous SO,Cl, can be applied to dry indigo white or to this in solid solvents such as Na,SO, or FeSO, and carriers such as iodin may be used. Near S. 885—‘“‘Brill. Indigo.”” Note 807,782 for brom product. 818,341—Apr. 17, 1906. Wilhelm BrHacuet and Gustav K. Schumann, Germany. (Badische.) Process of making phenylglycin salts. Phenyl glycin salt in improved yield. Chlor acetic acid with 5 parts ANILIN heated 3 hours at 100° temp., then aq. evaporated in vacuo at 120-140°, alk. carbonate or caustic added, excess anilin distd. over with steam, the phenyl crycin anilid separated, heated in an autoclave with one mol. caustic alk., the liberated anilin distd. off and soln. evapd. dry in vacuum. 8$19,348—May 1, 1906. Paul FRIEDLAENDER, Germany. (Kalle.) Red sulfur dye and process of making same. ‘Thio indigo. Thio INDOXYL or its carboxylic acid dissolved in dil. alk. and treated with oxidizinz agents, as K,;Fe(CN),, air, Fe,Cl, or K,Cr,O, in acid soln. Thio indigo is a red powd., sublimes to form bronze colored needles, is diff. sol. in usual solvents; and is a fast RED vat dye. S. 912—‘“‘Thio indigo Red B.”’ 823,294—June 12, 1906. Karl ScHIRMACHER, Germany. (Hdchst.) Vat-dye and process of making same. An indigo from the glycin of dianthranilic acid. DIANTHRANILIC acid and chlor acetic acid, Na salts, are refluxed in aq. soln., product sepd. and converted into Na salt by adding carbonate. The resulting glycin of DIANTHRANILIC acid, sod. salt, is heated in mixed KOH and NaOH melt in presence of a chemical capable of bind- ing water, to 270-280°, dild. and oxidized. Dyestuff is green-black powd., insol. in aq. and usual solvents, and sol. in conc. H,SO, (G); a fast GREEN vat dye. 831,844—Sept. 25, 1906. Gadient Ener, Switzerland. (Basle.) Process of making a red vat-dyeing dye. Thio indigo. Saticy, thio acetic acid, refluxed for about 5 hours in 5 parts nitro benzene soln. or other aromatic nitrohydrocarbon. Diphenylamin or other indifferent solvent may be used with the nitro solvent. Dyestuff is violet red powd., insol. aq. and cold alc., slightly hot alec. (VR), more sol. in hot benzene (R, fluor), sol. conc. H,SO, (BG), pptd. on diln.; a violet RED vat dye, fast to washing, light and Cl. S. 912—“‘Thio indigo Red B.” 836,309—Nov. 20, 1906. Gadient Ener, Switzerland. (Basle.) Red violet to violet-blue dye and process of making same. Thio indigo. Isatin a-arylids, such as IsATIN a-anilid, in acetic anhyd. or other solv., refluxed with sat- IcyL thio acetic, which forms thio 1npoxyL then combines with first component. Pure dyestuff consists of blue violet needles, sol. in conc. H,SO, (B), pptd. on diln., sol. in warm benzene (RV-BrR, fluor); red vioLetT to violet BLUE vat dye. S. 900. “Ciba Violet’? (non halogenated). Note 841,003 and 848,356 for halogenated dye and 848,355 for lower homolog. 839,099—Dec. 25, 1906. Augustus BiscHuER, Germany. (Badische.) Process of making indoxyl, &c. Indoxyl homologs or derivs., with higher yield and less decomp. Fifteen parts Na and 4o parts K salt of phenyl cGiycin or other aryl glycin or derivs., added to 240 pts. NaOH at 250° and to parts abs. alc. as vapor introduced by means of cur- rent of hydrogen, heating being continued until indoxyl does not increase. Previous methods give low yields or impure product, (sodiamiiietal). Use of alc. considerably increases the yield, S. 874—‘Indigo.” tei ait 9 ~% 841,003—Jan. 8, 1907. Gadient Ener, Switzerland. (Basle.) Yellow-red dye and process of making same. Thio indirubin. Thio sALIcyL acetic with 1saT1n or homologs in nitrobenzene soln., heated to 225-230° on oil bath for 2-3 hours. Orange red crysts., insol. in aq., diff. sol. hot alc., aniline and nitro- GROUP VII.—INDIGO AND INDIGOID 205 benzene (Rt.), sol. hot benzene and chloroform (VR-fluor), sol. cold conc. H,SO, (Br) and hot (VR), pptd. on diln. (Br); an orange rep vat dye. S. 905—“‘Thio Indigo Scarlet.” 841,456—Jan. 15, 1907. Robert ScHMiptin, Germany. (Hochst.) Process of making phenylglycin. Phenyl glycin or homologs. Sixty-two parts NITROBENZENE ‘or homolog, 100 parts ground cast iron and 7 parts ANILIN are heated to 70° in reflux app. and 47 parts chlor acetic acid in 100 parts aq. are gradually added, while keeping at boil. Temp. is kept at 98—-100° for two hours, mass neut. with Na,CO,, excess aniline distilled off, soln. filt., and phenyl glycin pptd. from conc. filt. by acid. S. 874—‘Indigo.” $48,354—Mar. 26, 1907. Gadient Encr, Switzerland. (Basle.) Halogenated red dye and process of making same. Dichlor thio indigo. 4-Chlor or brom 2-amino BENzoIc, diazotized, and combined with thio cGiycotic acid to form chlor thio saLicyL acetic in which the halogen is in para position to the carboxylic group. In nitro benzene or other nitro-hydrocarbon soln. this is heated to 225-228°. Reddish cryst. powd., diff. sol. alc. ether and CHCI,, sol. warm C,H, (VR-fluor), sol. boiling C,H;NO, (R), in conc. H,SO, (G), in fuming H,SO, (R); an orange rep vat dye. S. 909—‘*Ciba Red B.”’ Note 831,844. 848,355—Mar. 26, 1907. Gadient Enci, Switzerland. (Basle.) Red-halogen vat-dye and process of making same. Halogenated thio indirubin. Thio SALICYL acetic or thio indoxyl condensed with 1sarin, and product suspended in nitro- benzene or glacial acetic, slowly heated to a boil in reflux app. with bromine, chlorine, or with sub- © stances able to deliver up halogens. Brown to orange red cryst. powds., diff. sol. hot alc. and C,H,, easily sol. hot C,H,NO, (R), in conc. H,SO, (BrBk), in fuming H,SO, (RV), on diln. clear (BrR); a RED vat dye, faster to washing than a non-halogenated dye. S. 906—‘“‘Thio Indigo Scarlet, G.’? Note 841,003 for non-halogenated dye, 848,356 for an- ilid, and 836,309 for non-halogenated anilid. 848,356—Mar. 26, 1907. Gadient Ene1, Switzerland. (Basle.) Red-violet to blue vat-dyes and process of making same. Halogenated mono thio indigo. Thio InpoxyL or thio salicyl acetic condensed with a-1sar1n anilid, or other alfa isatin ar- ylid, using nitrobenzene or other indifferent diluent, then heated gently with bromine or other halogen. Dyestuffs are sparingly sol. in alc. and hot C,H,, easily sol. in C,H;NO, (BV), soln. in conc. H,SO, or in fuming acid (B), unchanged by heating and pptd. on diln.; red vioLET to BLUE vat dyes. S. 900—“Ciba Violet 3 B.” Note 836,309 for non-halogenated dye, 954,273 for mono. hal. dye, and 848,355. 850,444—Apr. 16, 1907. Arnold Rantyen and Carl StepnHan, Germany. (Rahtjen.) Process of making indigo. Indigo from isatin a-anilid. IsaTin a-anilid in alc., acetone or benzol soln., into which H,S is passed until colorless, di- luted and oxidized with air and alk., or simply heated. S. 874—‘Indigo.”’ 8$50,827—Apr. 16, 1907. Paul FRIEDLAENDER, Germany. (Kalle.) Thio-indoxyl derivative and process of making same. Thio indoxyl and carbo deriv. (Leuco thio indigo.) Cutior acetic and thio satrcytic condensed to form thio saLicyt acetic acid, heated with NaOH at 160-250° or with acetic anhyd. at 50-80°, to thio 1npoxyL carbo, then heated or acid added to form thio Inpoxyt. Derivs. are claimed. Carboxyl group eliminated by heating with or without acids and by steaming. Products are diff. sol. aq., easily sol. alk., and form RED dyes when oxidized. S. 912—‘“‘Thio Indigo Red B.” 856,687—June 11, 1907. Gadient Enc1, Switzerland. (Basle.) Tribromo derivatives of indigo and process of making same. _ Tribrom indigo. Inpico refluxed in nitrobenzene or 2-nitrotoluene soln., to which sufficient bromine is added to form tri-brom indigo; glacial acetic, or trichlor benzene or 2-nitro toluene also may be used 206 DIGEST OF PATENTS as solvents. Dark blue to brownish violet powd., insol. aq., sol. hot aniline or nitrobenzene (B-Bv), sol. conc. H,SO, (GB), in fuming sulf. (B); a BLUE vat (GY) dye, fast to washing light and chlorine. S. 880—‘‘Helindon Blue BB.” Note 729,217, 807,782, 856,776 and 883,703 for other brom products. 856,776—June 11, 1907. Gadient Enc1, Switzerland, (Basle.) Tetrabromo derivative of indigo and process of making same. ‘Tetra brom indigo. InpIGo or its mono-, di- or tri-brom substitution product brominated in nitrobenzene, or other soln. by refluxing at 225° for 1.5 hours or allowing to stand at room temp. 3-4 hrs., then refluxing at 130-135°. Blue to blue-violet powds., insol. aq., diff. sol. hot chloroform, aniline or nitrobenzene (B-BV), sol. conc. H,SO, (B); BLuE vat (Yt) dye, fast to washing, light, chlorine. S. 881—“‘Dianthrene Blue BB.” Note 916,217 and also 883,703 for modified process. 860,900—July 23, 1907. Nikodem Caro, Germany. (Cianamide.) Process of making indigo. Larger yields of indigo. Phenyl Guycin, derivs. or salts, added to hot melt (350-400°) consisting of disodium cy- anamid, 1 part, with sodium cyanide, 5 parts, as an inert flux of low melting pt., cooled, diluted and oxidized by air to produce dye. S. 874—“Indigo.” 867,305—Oct. 1, 1907. Karl ScHIRMACHER and Bernhard Deicke, Germany. (Hdéchst.) Vat-dyestuff. 6.6’-Dialkoxy thio indigo. 3-Amino 4-CRESOL is acetylated then ethylated to form acetyl 3-amino 4-cresol ethyl ether, oxidized (KMnO,) to 4-ethoxy acetyl ANTHRANILIC acid, separated by acid, saponified in NaOH soln. and diazotized. Diazo soln. treated with alk. xantHocENic acid then alk. chlor AcETIC to produce 4-ethoxy thio saLicyL acetic acid which, heated in NaOH to 180-200° yields 4- ethoxy thio NAPHTHENE carbo. Oxidation in alk. soln. (ferricyanide) produced dye. Methyl deriv. also claimed. Orange red powds. insol. aq., slightly sol. hot alc., C,H,, acetic and CHCl, (OR), sol. conc. H,SO, (VB), heated with HCl splits off alkyl chlorides; an orange RED vat (Y) dye. S. 913—‘‘Helindon Orange R.” 867,306—Oct. 1, 1907. Karl ScHIRMACHER and Richard Letopotp, Germany. (Ho6chst.) Vat-dyestuff. Diethyl 6.6’-dithio thio indigo. 3-Nitro 4-AcETOLUIDIN (NH, = 1), oxidized and reduced to give 4-acetamino ANTHRANILIC, diazotized, potass. xanthogenate added in alk. soln., then heated with alk. chlor acetic at 100° for 3 hours, and the 4-acet amino 2-thio SaLIcyL acetic pptd. by acid. Separated product is saponified, diazotized, potass. xanthogenate again added in alk. soln. to form 4-xanthogenyl thio salicyl acetic, which is pptd. by acid, then refluxed with caustic and sod. ethyl sulfate to yield alkyl-4-thionyl thio salicyl acEric, which, pptd. by acid, heated again in caustic at 180— 190° gives alkyl 4-thionyl oxythio naphthene carbo acid. This will yield on oxidation in alk. soln. (ferricyanide) a thio indigo. Red powds., insol. aq., slightly sol. hot alc., acetic, C,H, and CHCl, (OR), in conc. H,SO, (GB), heated with HCl splits off alkyl chloride; an alizarin RED vat (Y) dye. S. 916—‘‘Helindon Scarlet S’’ 867,679—Oct. 8, 1907. Albrecht Scumipt and Wilhelm Bertram, Germany. (Hochst.) Red-violet dye and process of making same. Tetra chlor thio indigo. 2-ACETTOLUIDIN dichlorinated, oxidized (KMnO,) to dichlor acet ANTHRANILIC acid, hydro- lyzed, diazotized, transformed into dichlor thio saLicyLic acid, or its di- or tri-thio carbonic acid ester, then by means of chlor acrETic in alk. soln. changed to 3.5-dichlor phenyl thio cLy- COLLIC 2-carbo acid. Heating with 4o per cent bisulfite at 150° under pressure or in acetic acid, forms dye. Brom comp. also claimed. Violet black powds., diff. sol. conc. H,SO, (G), in hot C,H,NO, (RV); red vioLeT vat (Y) dyes. | GROUP VII.—INDIGO AND INDIGOID 207 867,714—Oct. 8, 1907. Gadient Enc1, Switzerland. (Basle.) Process of making a halogenated red dye. Halogenated thio indirubin. Thio INDOXYL (a-oxy thio naphthene) or salicyl thio acetic condensed with rsatIN, hal- ogenated with mixed conc. HNO, and HCl and pptd. by diln. A rep vat dye of same prop- erties as 848,355. i S. 906—“Thio Indigo Scarlet G.” Note 867,715 for isomer and 848,355, 887,609 for hal- ogenated dyes by other processes. 867,715—Oct. 8, 1907. Gadient Enc1, Switzerland. (Basle.) Halogenated red vat-dye and process of making same. Dibrom thio indigo. Thio InDIGO (from sALicyL thio acetic heated in soln. of nitrobenzene or other nitro hy- drocarbon) brominated at 130-135° by refluxing with bromine, also in nitrobenzene soln. Other halogen compounds claimed. A gray violet cryst. powd., sol. conc. H,SO, (BG), pptd. on diln. (RV), diff. sol. hot C,H, (VR), easily sol. hot C,H;NO, (VR-Y flour); a violet rep wat (Yt) dye. S. 915—“Ciba Bordeaux B.” Note 851,844, isomer 848,354 (S. 909) and 867,714. 761,440—May 31, 1904. Augustus BiscHLER, Switzerland. (Basle.) Process of making indoxyl, &e. Increased yield of indoxyl, homologs and derivs. PHENYL glycin sodium salt, or other aryl glycins or derivs., and caustic alkali heated in alkali melt at 230° then to 260°. Melt is formed from metallic Na, in dry KOH, with or without a little reducing substance such as sodium sulfite, in absolute alc. distilled in vacuum on oil bath until all alc. is removed. S. 874—“‘Indigo.”’? Note 776,884. 868,294—Oct. 15, 1907. Robert ScHMipLIN, Germany. (Hdéchst.) Process of producing phenyl glycin and its homologues. Phenyl glycin and homologs. Chlor acetic acid and ANILIN or other primary base are refluxed in a suspension of freshly pptd. ferrous hydrate in a satd. soln. of NaCl or other indifferent alk. salt. The ferrous hy- drate is prepared from ferrous chloride or carbonate soln. to which sufficient NaOH or Na,CO, is added, followed by alkali salt to saturation and heating to 90-100°. Phenyl glycin iron salt formed is decomp. by NaOH or Na,CO,, anilin distilled off, iron removed by filtration and glycin pptd. by acid. S. 874—“Indigo.” 868,295—Oct. 15, 1907. Albrecht Scumipt, Germany. (Hochst.) Vat-dye and process of making same. Thio indigo and halogen derivs. Phenyl thio GLycocot 2-carbo (salicyl thio acetic) the tolyl, chlor phenyl or other aryl or halogen aryl deriv., heated with 6 parts bisulfite to 150-190° under pressure. Claims same dye as is produced by alk. fusion. Red powd., sol. conc. H,SO, (dark YG), in hot C,H,NO, (VR), giving red streak on porcelain; a violet RED to orange RED vat dye. S. 912—“*Thio Indigo Red B.”’ 868,755—Oct. 22, 1907. Hans Beart, England Process of making indigo, &e. Improvement in yields of indoxyl and indigo. Phenyl ciycin 2-carbo, di sodium salt, refluxed dry with ANILIN and metallic sodium (sodium anilid) or other aryl sodamid, or mitxures of sodamid with aryl amins, or other glycins. S. 874—“‘Indigo.” 872,085—Nov. 26, 1907. Albrecht Scumipt, Germany. (Hoéchst.) Brown vwat-dye. Acet-s-amino thio indoxyl-2-carboxylic or leuco 6.6’-diamino thio indigo. Acet 4-amino ANTHRANILIC acid, diazotized, treated in alk. carb. soln. with XANTHOGENIC acid, then chlor acetic acid to form acet 5-amino thio salicyl acetic acid, which is condensed in alkali then oxidized in neut. or faintly alk. soln. with ferric salts. Brown powd., insol. in aq., alk. or dil. acids, sol. conc. H,SO, (B), diff. sol. in C,H;NO, (OBr); a BRown vat dye. Isomer of S. 927—‘‘Helindon Gray 2B.” Note 872,585 for hal. dye, 872,086 and 959,617 for isomers. 208 DIGEST OF PATENTS 872,086—Nov. 26, 1907. Albrecht Scumipt, Germany. (Hochst.) Green-black wat dye. Acet.-5-amino thio naphthene indoxyl carbo or leuco 5.5’-diamino thio indigo. Acet. 5-amino ANTHRANILIC acid treated by same process as 872,085, with amino group in para, not meta, position to the sulfur. A black powd., insol. aq., caustic, dil. acids, alc., ether, or benzene, sol. conc. H,SO, (dark GB); a green BLacK vat (YG) dye. Isomer of S. 921—‘‘Helindon Gray 2B.”’ Note 872,085 and 959,617 for 3.3’ and 2.2’ iso- mers and 872,585 for hal. dye. 872,115—Nov. 26, 1907. Gadient Ene1, Switzerland. (Basle.) Mixed chlorobromo derivatives of indigo and process of making: same. Mixed mono or dichlor, mono, di, or tri brom indigo. Mono or di-chlor INDIGO, suspended in nitrobenzene or other indifferent medium, di- or tri-brominated at 225-228°. Blue to violet powds., insol. aq., somewhat sol. hot C,H,NH, or C,H,NO, (B-V), sol. fuming H,SO, (B-V); vioLeT to BLUE vat (Yt) dyes, fast to washing, chlorine and light. Near S. 884 or 887—‘“‘Brilliant Indigo.”? This patent apparently antedates S. 884 or 887 (1911) by four years. 872,227—Nov. 26, 1907. Gadient Enc1, Switzerland. (Basle.) Green vat-dye and process of making same. Halogen-1.2-naphthindigoes, or di- brom 1.2-naphthindigo. I.2-NAPHTHISATIN, brominated, refluxed with POCI,, containing PCI, added to 1o per cent HI in glac. acetic, boiled, cooled, and poured into aq. SO, or NH,SH and alc., made alk., di- luted and oxidized by air. Other halogen derivs. claimed. Dark green cryst. powds., sol. conc. H,SO, (GB), easily sol. hot C,H,NO, (GB); vivid GREEN vat (RBr) dyes, fast to washing, light, and chlorine. S. 891—‘‘Ciba Green G.”’ 872,280—Nov. 26, 1907. Gadient Ene1, Switzerland. (Basle.) Monochloromonobromo derivatives of indigo and process of making same. Brom chlor indigo. Inp1co, mono-chlorinated in nitrobenzene soln. suspended in C,H.NO,, refluxed with a little more than two atomic proportions of bromine at 226° on oil bath for 2 hours. A blue cryst. powd., sol. conc. H,SO, (YG-BG), sol. fuming H,SO, (B), nearly insol. alc. and C,H,, some- what sol. hot C,H, NH, (GB) and hot C,H,NO, (B); a violet BLUE vat (Y) dye fast to washing, chlorine and light. 872,585—Dec. 3, 1907. Albrecht Scumipt and Carl Prerzerr, Germany. (Hochst.) Orange vat-dye and process of making same. _ 5.5/-Dibrom 6.6/-diamino tho indigo. Acetyl 4-amino thio sALIcyL acetic, heated with alkali, leuco body oxidized to thio in- digo then chlorinated or brominated in nitrobenzene, chlorbenzene, glac. acetic acid, or other diluent. Brown powds., insol. aq., alk., dil. acids, alc., acetone, diff. sol. hot C,H,NO, (OBr), sol. conc. H,SO, (B); oRANGE vat dye, fast. S. 914—‘‘Helindon Orange B.’”? Note 963,813 for ethoxy deriv. 874,649—Dec. 24, 1907. Karl ALBrEcHT, Germany. (Kalle.) Thio-indoxyl derivatives and process of making same. ‘Thio indirubin. Thio InDOxYL (a-oxy thio naphthene) or its carboxylic acid in hot alk. aq., condensed with ISATIN. Scarlet red needles, insol. or diff. sol. usual solvents, sol. conc. H,SO, (Br); an orange RED vat dye, fast to all agents. S. 905—‘“‘Thio Indigo Scarlet R.’? Note patent apparently duplicates 841,003 issued nearly 12 months earlier to Engi, Basle. 876,158—Jan. 7, 1908. * Gadient Enc1, Switzerland. (Basle.) Vat dye derived from indirubin and process of making same. [Di, tetra or poly brom indirubin. INDIRUBIN, from INDOXYL and ISATIN, refluxed in nitrobenzene for 3-4 hours at 130-140° with two or more atomic proportions of bromine. Violet cryst. powds., sol. conc. H,SO, (GB- G), sol. hot C,H,NH, and C,H,NO, (V); vioLtET vat (Y) dyes, fast to washing and chlorine. S. 897—“Ciba Heliotrope D.” GROUP VII.—INDIGO AND INDIGOID 209 876,839—Jan. 14, 1908. Rudolf Pummerer, Germany. (Badische.) Red dye and process of making same. Thio indirubin, homologs and derivs. 2.3-Diketo dihydro thio NAPHTHENE (thio ISATIN), homologs or derivs, condensed with 3- oxy thio NAPHTHENE (thioindoxyl), or other aryl thio glycolic acid or ortho carboxyl derivs., by heating at 140° with exclusion of air, with or without diluents such as C,,H,, C,H,NO, or C,H,,OH and with or without a condensing agent such as (CH,CO),O, ZnCl,, CaCl, or min- eral acid. Products may be sulfonated. Violet to brown red powds., sol. in C,H, (V-YR), sol. conc. H,SO, (Br-G); BLUE to RED vat dyes or in sulfonated form blue vioLET to brown-RED acid dyes. 877,702—Jan. 28, 1908. Ernst Bryx, Germany. (Hochst.) Process of making arylthioglycollic-orthocarboxylic acids. Phenyl thio gly- colic 2-carbo acid, or other aryl derivs. ANTHRANILIC acid diazotized, soln. neut. with Na,CO, and at o-10° allowed to run slowly into an excess of Na,S soln., chlor acetic acid, Na salt, and NaOH added, heated for one hour at 100° and pptd. by acid. 877,743—Jan. 28, 1908. Albrecht ScHmMiprt and Ernst Bryx, Germany. (Hochst.) Violet dye and process of making same. _5.5’/-Dimethyl thio indigo and homologs or derivs. ps-CumipIn, chlor toluidin or other amin, substituted in para position, but not in one ortho position, diazotized, condensed with xANTHOGENIC acid, then with chlor acetic in alk. soln. to form a para substituted aryl thio glycolic acid, which is heated gently with several parts H,SO,, monohydrate or 66°. Accelerators such as bisulfate, pyrosulfate, boric or phosphoric acids, chlorides, aromatic sulfo acids, or sulfur, increase yields. By regulating quantity and strength of sulfuric acid, and temp. and time of heating, an unsulfonated condensed di- or poly-alkyl thio-indigo results. Dyes are insol. aq., alk., dil. acids, sol. hot C,H,;NO, (RV), sol. conc. H,SO, (G); blue vioLer vat dyes. Near S. 912—‘‘Thio Indigo Red B.” 881,157—Mar. 10, 1908. Karl ScHIRMACHER and Richard Leoporp, Germany. (Ho6chst.) Dark-green-black dye. Methyl or ethyl 5-thio indoxyl or leuco dimethyl or diethyl 5.5/-di- thio thio indigo and homologs. : Acet 5-amino ANTHRANILIC acid diazotized, combined in alk. soln. with xANTHOGENIC acid, then warmed in alk. soln. with chlor acEtic to form acet 5-amino thio SALICYL ACETIC, which is separated, hydrolyzed, diazotized, again combined with xanthogenic acid, refluxed in alk. soln. with METHYL or ETHYL sulfate, heated with NaOH to 180-190° to close ring, and finally oxidized to dye by alk. ferricyanide. Dark green black powds., insol. aq., sol. in alc. glac. acetic, C,H, and CHCl, (V), in conc. H,SO, (BG); black crrEN vat (Y) dyes. Thio isomer of S. 913—‘“‘Helindon Orange R.”’ 881,158—Mar. 10, 1908. Karl ScuriRMACHER and Bernhard Deicke, Germany. (Hochst.) Dark-blue-violet dye. 5.5’/-Dimethoxy or diethoxy thio indigo. 4-Amino PHENOL 5-carbo, acetylated, alkylated in alk. soln. with pIMETHYL sulfate, or other, to form 4-acetyl amino ANisoL 5-carbo, which is saponified, diazotized, condensed with xanTHo- GENIC acid then with chlor acetic, pptd., fused in alkali to close the ring, and oxidized. Dark violet powds., insol. aq., sol. hot alc., glac. acetic, C,H, and CHCl, (V), in conc. H,SO, (G); blue vioLeET vat (Y) dyes. Isomer of S. 813—‘‘Helindon Orange R.”’ 881,159—Mar. 10, 1908. Karl ScuIRMACHER and Arnold Brunner, Germany. (Héchst.) Red vat-dye. (Product.) 4.4’-.6.6’-Tetra methyl thio indigo. 6-Nitro 4.2-xYLIpINn diazotized, nitrile form, d by CuSO, and KCN, hydrolized in acid soln., the resulting 6-nitro 4.2-xyLIc acid reduced, ‘diazotized and condensed with xANTHOGENIC acid in alk. soln. then with chlor acetic acid to form 4.6-dimethyl thio salicyl acetic, which is con- densed in alkali to 4.6 dimethyl oxy thio naphthene carbo and oxidized with alk. ferricyanide. Red powd., insol. in aq., very diff. sol. hot alc., more sol. hot C,H,, glac. acetic and CHCISCR); sol. conc. H,SO, (G); a pale rep fast vat (Y) dye. Note 881,624 for similar dye by slightly different process, 210 DIGEST OF PATENTS 881,624—Mar. 10, 1908. Albrecht Scumipt and Ernst Bryx, Germany. (Héchst.) Making vat-dyestuffs. (Product claimed.) Tetra- to hexamethyl thio indigo, or other. 2.4-XYLIDIN, 2.4.5-cumidin, or similar amin, diazotized and combined with XxANTHOGENIC then with chlor acetic acid to form 2.4-xylyl thio GLyconic acid, or other para methyl substi- tuted aryl thio glycolic acid, such that one hydrogen in ortho position to the sulfur is not substituted,_-which is condensed in chlor sulfonic soln. Violet powds., insol. in aq., alk., dil. mineral acids, sol. conc. H,SO, (G), in hot C,H;NO, (RV); blue vio.er vat dyes. Note 811,159 for similar dye. $83,703—Apr. 7, 1908. Gadient Ener, Switzerland. (Basle.) Process of making dibromindigo. Dibrom indigo. INDIGO in nitrobenzene soln. to which a theoretically sufficient amount of bromine, 4 atoms, is added to form dibrom indigo, heated to 225—-228° for 1.5 hours. Process adds 37.5 per cent Br as compared with 33 per cent by former methods. Deep blue cryst. powd., a violet BLUE vat (Y) dye, more intense and faster than indigo to washing and chlorine. S. 880—‘‘Helindon Blue BB.” Note 729,217, 807,782, 856,687, 856,776. 887,609—May 12, 1908. Gadient Enc1, Switzerland, (Basle.) Red halogen wat-dye and process of making same. Halogenated thio indirubin. IsaTin, brominated in glacial acetic soln. to mono or dibrom isatin, or other halogen deriv., boiled in nitrobenzene, or other solvent, with 3-oxy thio naphthene, from sAticyLic thio acetic, using a condensing agent such as acetic anhyd. Dyes are slightly sol. in hot C,H, or C,H,;NO, (Rose-R), sol. conc. H,SO, (dull Br); RED vat (Y) dyes, fast to washing, light, and chlorine. S. 906—“Thio Indigo Scarlet G.”’ Note 867,714 and 848,355, etc., which employ different processes to obtain halogenated dyes, and also 841,003. 888,230—May 109, 1908. Gadient Ener, Switzerland. (Basle.) Process of making monobromo indigo. Brom indigo. INDIGO in nitrobenzene soln., refluxed 1.5-2 hours at 225-228° with sufficient bromine (2 atoms) to form mono brom dye. Dye contains theoretical amount of bromine, 24 per cent. A blue cryst. powd., giving a sLuE vat (Y) dye faster to washing and chlorine than mono brom deriv. Indigo R. Near S. 880—Helindon Blue BB.” Note 856,687 and 856,776. $91,690—June 23, 1908. Armin Gros, Switzerland. (Basle.) Red vat-dye and process of making same. Thio indole acenapthene indigo. Phenyl thio GLiycoco, 2-carboxylic, or 3-oxy thio naphthene, and ACENAPHTHENE quinone, heated dry to 230—250° or refluxed with sodium acetate in acetic anhyd., or alc. soln. Dye may be sulfonated. It is sol. in hot glac. acetic and hot C,H,, sparingly sol. in alc., sol. conc. H,SO, (G); an orange RED vat (V) dye. S. 907—“Ciba Scarlet G.’”’ 888,852—May 26, 1908. Karl ScuirMACHER and Arnold Brunner, Germany. (Hodchst.) Brown vat dye. I-NAPHTHYLAMIN 2-sulfo diazotized, changed by CuSO, and KCN to 1-cyan NAPHTHALENE 2- sulfo, then by PCI, and POC, to 1-cyan naphthyl 2-sulfo chloride, which is treated with dil. H,SO, and Zn dust, separated and heated in alk. chlor acrrTic, resulting naphthalene 2-thio glycolic 1-carbo acid heated at 180-190° in NaOH, to oxy thio PHRENTHRENE carbo acid, or fur- ther saponified to oxy thio PHRENTHRENE. Latter comps., oxidized in alk. soln., form dye. Properties of purified intermediates are given. Brown powd., insol. aq. and alk., sol. in hot alc., CH cet, 891,708—June 23, 1908. Hans Lasuarpt, Germany. (Badische.) Process of producing indoxylic compounds. Indoxyl compounds. Acetyl phenyl ciyc1n homologs, analogs and derivs., dry and finely powdered, mixed with 1-4 parts freshly prepared, finely ground aluminum chloride, heated to 220-250° in a closed vessel in vacuo, in atmosphere of hydrogen, nitrogen, CO, or other indifferent gas, cooled, added to boiling dil. NaOH to saponify then oxidized by air. Other aluminum halides and acylated aryl glycins claimed. S. 874—“Indigo.” GROUP VII.—INDIGO AND INDIGOID 2I1 hot 892,897—July 7, 1908. Karl ScHIRMACHER and Hermann Lanpers, Germany. (Hochst.) Red vat dye. 4-Methyl 6-chlor thio indoxyl or leuco 4.4’-dimethyl 6.6’-dichlor thio indigo. 4-Chlor 6-nitro 2-roLuyLic acid, reduced with Na,S to an amin, diazctized, then combined in alk. soln. with xANTHOGENIc and chlor acetic acids to form 4-methyl 6-chlor thio salicyl acetic acid, which when heated with alkali to 180-190° and prtd. by acid forms 4-methyl 6-chlor oxy thio naphthene carbo acid. Alk. oxidation gives dye. Dyes are red powds., insol. aq., alc., ether, sol. in hot C,H,NO, and glac. acetic (R), in H,SO, (G); a pale RED vat (Y) dye. S. g10—‘Helindon Blue, BN.” 894,004—July 21, 1908. Benno Homo.ka and Richard Wepre, Germany. (Hochst.) Process of making alpha-oxythionaphthenes. Thio indigo from a-oxy thio naph- thene, homologs or carboxyl derivs. Methyl thio saticytic acid, methyl ester, heated with about equal parts alk. alcoholate and 4 to 6 parts molecular mixture of NaOH and KOH, at 150 to 200°, to form a-oxy thio NAPH- THENS. Other condensing agents may be used, such as dialk. dicyanamid, amalgams or alloys, alk. alcoholates, alk. earths, metals, etc. Products are RED to VIOLET vat dyes. S. 912—‘Thio indigo Red S.’”’ Note 894,005. 894,005—July 21, 1908. Benno Homo.ika and Richard We.pe, Germany. (Hochst.) Process of making sulfurized dyes. C,,H,S,0,. a-Oxy thio NAPHTHONES or a-oxy thio NAPHTHENE carbo acids heated at roo—130° in closed vessel with 10 parts cryst. Na,S,0,. Red cryst. powds., insol. aq., sol. conc. sulf. (G), in CHCl, (R), reduced by alk. agents; RED reducing sulfide vat dyes. S. 912—‘*Thio Indigo Red B.” Addition to 894,004. 894,006—July 21, 1908. Benno Homo.xka and Richard WeE.tpEe, Germany. (Hoéchst.) Sulfurous leuco body and process of making same. _ Leuco thio indigoes. a-Oxy thio NAPHTHENES, or carboxyl derivs., heated with to parts cryst. sod. thiosulfate (6 aq.) or other soluble thiosulfate and 10-15 parts comm’! GLYCERIN in closed vessel to temp. above 100°. Leuco body is colorless, little sol. in aq., readily sol. in alc., wood alc., acetone and dil. alk., not fusible without decomp., alk. soln. exposed to air ppts. REpD, BLUE, VIOLET to red BROWN vat dyes. Near S. g912—‘‘Thio Indigo Red B.”’ §$94,149—July 21, 1908. Georges Imsert, Germany, Process of producing glycin derivatives. Phenyl glycin and derivs. Dichlor ethoxy ETHYLENE or dibrom deriv., 1 mol., prepared as in 894,148 (see Intermediates) refluxed with 3 mols. ANILIN or other aromatic amin in aq. or dil. alc. soln. with or without HCl, or heated at 150° in an autoclave. The excess halogen salt of aromatic amin may be re- covered. 894,579—July 28, 1908. Augustus BiscHLEeR, Switzerland. (Basle.) Process of making indoxyl, &c. Indoxyl or leuco indigo. ANILIN, or other amin, added to a heated mixture of NaOH and Na, followed by PHENYL glycin, or other, and heating continued at 225-235° until 1npoxyL is formed. Difficulty caused by foaming from evolved hydrogen, in processes where the glycin is first added then the amin, is avoided by reversing this order. S. 876—‘“Indigo White.” Note 776,884. 898,452—Sept. 15, 1908. Gadient Enc and Jaroslav Frouiicu, Switzerland. (Basle.) Vat-dye from indirubin and process of making same. as-Dibrom indirubin, or other dihalogen deriv. InpoxyL, phenyl glycin, methyl indoxyl or derivs., boiled with dibrom 1satin, or other dihalo- gen isatin (see list) in alk. soln. Brown red powds., sol. conc. H,SO, (dull BrV-V), sol. fuming H,SO,, 24 per cent (V), sparingly sol. hot C,H,, more sol. hot C,H,NO, (V); a pale vioLEeT vat (Yt) dye, fast to washing and chlorine. Near S. 897—‘‘Ciba Heliotrope B.” 212 DIGEST OF PATENTS 898,738—Sept. 15, 1908. Benno Homorixka, Germany. (Ho6chst.) Oxid of thioindigo dyes. Thio indigo oxide, C,,.-H,0,5,, and derivs. (constitution not given). Thio INDIGO or substituted thio indigo oxidized by strong agents such as HNO,, CrO,-H,SO,, etc. Red cryst. powd., insol. aq., ether and ligroin, sol. in boiling CHCl, and xylene (R), in conc, H,SO, (RV), in dil. caustic or neut. sulfite (OY), latter soln. when heated with dil. mineral acids yields red ppt., which can be produced on the textile fiber; fast RED vat dye. 889,152—Sept. 22, 1908. Wilhelm Baver, Germany. (Bayer.) Process of making red vat-dyes. 6.6’-Dihalogenated thio indigo, or other. 4-Chlor phenyl thio Giyco1ic acid or other halogenated aryl glycolic acid, mixed with chlor sulfonic acid (free from sulfuryl chloride but containing some moisture) keeping temp. low. Red powds., bronzy luster, sol. conc. H,SO, (YG); a RED vat (Y) dye. Near S. go09—‘“‘Ciba Red B.” 899,863—Sept. 29, 1908. Gadient Ener and Herman Krart, Switzerland. (Basle.) Trichlorindigo and process of making same. Improvement in process for tri- halogenated indigo. Inp1co, treated in nitrobenzene, or other aromatic nitro hydrocarbon solution, with Cl gas aided by SbCl, or other halogen carrier to trichlor indigo. A violet bronze powd., insol. aq., diff. sol. CHCl, and C,H,, more easily sol. in hot C,H,NO, (VB), sol. in conc. H,SO,(GB); a BLUE vat (Yt) dye, fast to washing, light and chlorine. Note 915,338. 899,994—Sept. 29, 1908. Hermann Kraft and Gadient Enc1, Switzerland. (Basle.) Violet vat dye and process of making same. Brom thio indigo, or other. NITROBENZENE condensed with 3-oxy thio NAPHTHENE in alc. soln., form the a-anilid of thio ISATIN, (2.3-diketo dihydro thio naphthene) or other alpha arylid, then boiled 3 hours together with ACETINDOXYL or indoxyl and Na,CO, in alcohol or nitrobenzene soln. and violet cryst. product separated, suspended in nitrobenzene, heated in oil bath at 220-230° and bromine added. Dark violet powds., sol. conc. H,SO,(B-GB), in hot C,H,NO,(V); vIoLET to violet BLUE vat (BrY) dyes, fast to washing, light and chlorine. Near S. 906—‘‘Thio Indigo Scarlet G.” 904,867—Nov. 24, 1908. Armin Gros, Switzerland. (Basle.) Violet vat dyestuff and process of making same. Acenaphthene indigo. ACENAPHTHENE quinone condensed by heating in 90 per cent alc. soln. with INDoxyYL, adding trace of piperidin or calcined soda to ppt. dye, while hot. Dye is sol. in conc. H,SO,(G), diff. sol. hot alc. (BV), more easily sol. hot C,H,(RV); a vioLEeT vat dye. Near S. 907—‘‘Ciba Scarlet G.”? Note 891,690 for thio dye of same form. 906,029—Mar. 23, 1900. Albrecht ScHmMipt and Ernst Bryx, Germany. (Héchst.) Red-violet dye and process of making same. _ 5.5/-Dichlor dimethyl thio indigo, or homologs. Chlor tolyl thio ciycocor acid (from 4-chlor 2-toluidin xANTHOGENIC and chlor AcETIC acids) or other aryl thio glycolic acid with halogen in para position and one ortho position free, heated at 100° with conc. sulfuric acid, then poured into aq. List of substituted amins possible to use (8) is given with color and reaction of dyes. Dyes are insol. in aq., alk. and dil. acids, sol. hot C,H,;NO,(VR), in conc. H,SO,(G); red vioLeT to violet RED dyes. S. 917—‘“‘Helindon Red B.” 910,839—Jan. 26, 1900. Eduard Mitncu, Germany. (Badische.) Process of making thioindigo leuco compounds. Leuco thio indigo compounds (3- oxy thio naphthene carbo acids). w-Dichlor vinyl thio saticyLic acid (from thio saticyuic acid and trihalogen ETHYLENE) heated in mixed caustic and carbonated alkali to 125-150° then at 200-210°, dissolved and pptd. by HCl. Boiling in sod. alcoholate gives same product. Rep vat dye. S. 912—“‘Thioindigo Red.” ae ae Oe a | GROUP VII.—INDIGO AND INDIGOID 213 815,338—Mar. 16, 1909. Gadient Enc1, Switzerland. (Basle.) Mono-brom-trichlor indigo and process of making same. Mono brom ttrichlor indigo. Trichlor InDIGO made as in 899,863, suspended in nitrobenzene, is mixed with bromin and refluxed at 220-230°. Small violet brown coppery crysts., sol. conc. H,SO,(B), in fuming sulf. (GB), in hot C,H,NH,(B), in C,H,NO, (BV); a violet BLUE vat (Y) dye, fast to washing, light and chlorine. Addition to 899,863. 915,346—Mar. 16, 19009. Armin Gros, Switzerland. (Basle.) Vat dye and process of making same. Halogenated thioindole acenaphthene indigo. 4-Chlor thio sALIcyL acetic acid and finely powd. ACENAPHTHENE quinone are heated to- gether at 220-250° or heated in an indifferent solvent like naphthalene, or in acetic anhyd. and dry sod. acetate. Other halogens and substituents claimed. 3-Oxy-thio naphthene is formed during the process. Near S. 908—‘“‘Ciba Red R.” Note 891,690, 904,867 and 965,170. 916,030—Mar. 23, 1909. Albrecht Scumipt and Ernst Bryx, Germany. (Hochst.) Vat dye and process of making same. _ 7.7’-Dichlor thio indigo or other substituted 7.7'-dihalogen thio indigoes. 2-Chlor phenyl thio GLycotic acid from (2-chlor ANILIN diazotized and condensed with xan- THOGENIC and chlor acetic acid) added to cHLORSULFONIC acid with or without boric acid as accelerator, keeping temp. low. List of examples of other halogen aryl thio glycolic acids that may be used is given with colors produced on fiber. Dyes are insol. aq., alk., dil. acids, ligroin, alc. and ether, sol. hot C,H,NO, (VR), in cold conc. H,SO,(G), pptd. on diln.; RED VIOLET to BLUE vat (Y) dyes. S. 916—‘“‘Helindon Red B.” and 917 ‘“‘Helindon Red 3B.” Addition to 916,029. 916,031—Mar. 23, 1909. Albrecht ScuMipT, Germany. (Hoéchst.) Highly-brominated indigoes and process of making same. Highly brominated leuco indigo, with at least two atoms bromine in excess of tetrahalogen indigo. Dibrom INDIGO mixed with an excess of liquid bromine, with or without solvent such as CCl, CS, etc., and with or without a bromine carrier such as iodine or POCI,, to form a green- black unstable highly brominated product which loses bromine with heat or with hydrosulfite, etc., to form leuco dye. Products are green-black, insol. in aq. and in CCl,, sol. in alk. hydrate and dyeing wool and cotton BLUE from these solns. Note 918,920. $18,820—Apr. 20, 1909. Albrecht ScuMipt, Heinrich RossnErR and Hans Batyorn, Germany. (Hoéchst.) Highly-brominated halogen indigoes and process of making same. _ Highly halogenated indigo, containing at least five atoms of halogen. Dibrom 1npIGo gently heated to 20—-40° in 85 per cent sulfuric acid to which a large excess (more than 5 atoms) of bromine is added. ‘The green black mass loses bromine in aq. or bi- sulfite soln., turns blue and forms tribrom (45 per cent) leuco indigo. Higher temp. in sulfuric acid treatment gives tetra brom (55 per cent) product. Other halogen derivs. and homologs claimed. Products are sol. in much conc. H,SO,(BrG) and in alk. hydrosulfite soln. yield BLUE vat (gray G) dyes. Addition to 916,031. 920,156—May 4, 1909. Emil Kraus, Germany. (Cassella, N. Y.) Brominated indigo sulfid and process of making same. Halogen derivs. of indigo sulfid containing one atom S to two mols. indigo. InDIGO, in nitrobenzene or other diluent, to which is added bromine in same solvent, then sublimed sulfur and mixture allowed to stand, then heated to 120° and finally to 160-200°. Dark blue powds., almost insol. in alc., C,H,, CHCl, sol. in boiling C,H;NO, and C,,H,(GB), in conc. H.,SO,(BG), in 20 per cent oleum (sky B); a BLUE vat (Y) dye. 923,959—June 8, 1909. Gadient Enc1, Switzerland. (Basle.) Red vat dye and process of making same. _ dAcetyl thio indirubin. Acetyl 1sat1n and 3-oxy thio NAPHTHENE or derivs., boiled together in alcohol, or the oxy thio naphthene can be produced in the reaction mass by heating thio salicyl acetic acid with a ‘ 214 DIGEST OF PATENTS condensing agent (nitrohydrocarbon) and acetyl isatin. Products are diff. sol. cold alc. and C,H,, more sol. hot C,H, and C,H,NO,, sol. conc. H,SO, (dull Br); rep vat (Yt) dyes, fast to washing, light, and chlorine. Near S. 905—‘‘Thio Indigo Scarlet.”” Note 841,003, 848,355, 874,649 and 887,609. 932,334—Aug. 23, 1909. Albrecht Scumipt and Robert Voss, Germany. (Hoéchst.) Brominated beta-naphthylindigo. (Process claimed.) Brom naphthyl indigo and higher brominated indigoes. 2-Naphthyl rnp1co is suspended in CCl, and bromine added at low temp., product filtered and purified by bisulfite, alcohol, etc. Or 2-naphthyl indigo is refluxed in CCl, with sufficient bromine to form dibrom indigo (2 mols.) or is mixed at O° with liquid bromine, stirred for two days and diluted with CCl,, etc., to form higher brominated derivs. Dark green powds., sol. in conc. H,SO, (VB-B-BV), diff. sol. in usual solvents, somewhat sol. in C,H;NO, and C,H.NH,; fast GREEN vat dyes. S. 892—‘‘Helindon Green G.”’ 937,040—Oct. 19, 1909. Wilhelm Baver and Alfred Herre, Germany. (Bayer.) Tribromindigo and process of making same. Tribrom indigo. Inpico, finely powdered, dissolved in cooled conc. sulfuric acid, bromine, HBr, or NaBr, slowly added, gently heated to 30° and added to aq. containing some bisulfite. Less than theoreti- cal amount of bromine may be used as HBr is decomp. by conc. sulfuric. Cooling the H,SO, prevents sulfonation. Violet blue powd., sol. conc. H,SO, (GB), sol. hot glac. acetic, phenol and benzaldehyde (B), on oxidation gives brom isatin m. p. 215; a green BLUE vat (Y) dye. S. 881—‘‘Dianthrene Blue 2R.” Schulz places this with the tetra brom product, while patent expressly states tri brom. See also 856,776, 937,041. (Tetrabrom). 937,041—Oct. 19, 1909. ' Wilhelm Bauer and Alfred Herre, Germany. (Bayer.) Tetrabromindigo and process of making same. _ Tetrabrom indigo Inp1Go, finely powdered, added to conc. sulfuric acid, cooled to prevent sulfonation, bromine or other halogen slowly added and the whole heated to 45° then poured into aq. containing some bisulfite. Patent differs from 937,040 only in using sufficient bromine for the tetra brom deriv. instead of tri brom. Violet blue powd., sol. conc. H,S0O, (GB), sol. glac. acetic, phenol and benzaldehyde (B), oxidized gives brom isatin, m.p. 215°; a green BLUE vat (Y) dye. S. 88:1—‘‘Dianthrene Blue 2B.” Note 856,776, 916,217 and 937,040. 937,194—Oct. 19, 1909. Carl StepHan and Arnold Rantyen, Germany. Process of making sulfurous-acid compound of alpha-isatin anilid. Sul- furous acid compounds of a-isatin anilid and homologs. Diphenyl oxALAMIDIN thio amid, or homolog, dissolved in hot dil. sulfuric to form soln. of ISATIN a-anilid, which is poured into aq. containing SO,, one mol., or its equivalent as bisulfite sulfite or thio sulfate salt. Only slightly acid soln. is required. S. 874—‘Indigo.” 940,586—Nov. 16, 1909. Gadient Enc1 and Hans Kapreier, Switzerland. (Basle.) Brown vat dye and process of making same. Halogenated diamino indigo. 4.4’-Diamino INDIGO one part, mixed with 15 parts bromine for 48 hours at ordinary temp. then diluted by CCl,, or it may be heated with 1 part Br 2-3 hours at 110-120°, or with 1 part Br. it may be stirred in 66° sulfuric acid at or below O° for 12-15 hours. Other solvents, such as glac. acetic or di and tri chlor benzene may be used and halogen carrier employed. Brown powds. sol. in conc. H,SO, and oleum (B), in hot C,H,NO, (Br); red Brown vat dyes. 941,152—Nov. 23, 1909. Hermann Krart, Switzerland. (Basle.) Vat dye and process of making same. Halogen thio naphth-indigo. Brom b-NAPHTHYLAMIN chloride, from brom b-naphthisatin and PCl,, and 3-oxy thio NAPH- THENE, boiled in xylene soln. Dibrom derivs., halogen salts, and alfa as well as beta naphthisatin may be used in nitrobenzene, xylene or other solvent. Brown-red powds., sol. conc. H,SO, (G-GB), in hot C,H,NO, (R-V); brown VIOLET, gray VIOLET to vioiet BLACK vat dyes, fast to washing, light and chlorine. ' f ‘ ‘ GROUP VII.—INDIGO AND INDIGOID 215 943,560—Dec. 14, 1909. Eduard Mincu, Germany. (Badische.) Thiosalicylic compound and process of making same. Ethylene (‘acetylene’) bis thio salicylic acid for thio indigo mfr. Thio SALICyLIc acid, dipotassium salt, its sulfur or halogen derivs. or esters, and dichlor ETHYLENE or other symmetrical dihalogen acetylene in alc. soln. containing a little KOH, refluxed at 100°. Sulfo cyan benzoic acid may be used and anthracene o-sulfoxy carbo acid also. S. 912—““Thio Indigo Red.” Note 943,561 . 943,561—Dec. 14, 19009. Eduard Mitncu, Germany. (Badische.) Thiosalicylic compound and process of making same. w-Dihalogen vinyl thio salicylic acid for thio indigo. Thio saticyiic acid, homologs, analogs and derivs., refluxed in alc. KOH with trichlor etuy- LENE, and pptd. with acid. Process and components the same as 943,560 except trichlor ethylene is used instead of dichlor ethylene. Colorless or slightly colored crysts., easily sol. in alc. or C,H,, more diff. sol. in ligroin, insol. in aq., alk. condensing agents give leuco thio indigo colors. S. 913—‘*Thio Indigo Red.” $43,678—Dec. 21, 19009. Benno HomoiKa and Robert WeEtp£, Germany. (Hochst.) Leuco bedy containing sulfur and process of making same. Leuco thio indi- rubin. Drox1NDOLE (by reduction of IsATIn with Zn and HCl) or derivs., mixed in aq. with a-oxy thio naphthene or its carbo acid, with or without -acid or alkali carbonate as an accelerator. White or reddish cryst. powds., slightly sol. aq., sol. in alc., acetone and dil. alk., the alk. soln. on exposure to air or other oxidizing agent deposits an insol. thio indirubin dye. S. 905—‘“‘Thio Indigo Scarlet R” etc. 947,030—Jan. 18, 1910. Albrecht Scumipt and Ernst Bryx, Germany (Hochst.) Vat dye and process of making same. Amino 5.5/-dichlor-7.7’-dimethyl thio indigo. Thio rnpi1co, chlor or methyl derivs. or other, nitrated in absence of aq. and reduced or not or halogenated or not. Nitro group when present as such is reduced in the dye vat. Violet to dark powds., insol. in aq., dil. alk. and acids, ligroin, alc. and ether, sol. conc. H,SO, (G-GB); VIOLET to violet GRAY to BLACK vat dyes. Near S. g10—‘‘Helindone Rose BN.” 948,241—Feb. 1, 1910. Paul E. Oserreit, Viktor VitzicerR and Paul Nawrasky, Germany. (Badische.) Halogenated indigo and process of making. = 5.5’-Dibrom-7.7’-dichlor indigo. 4-Brom 6-chlor phenyl GiycIN 2-carbo, methyl ester (from phenyl glycin carbo acid, chlor- inated, brominated, then methylated), condensed in alc. soln. containing metallic sodium as con- densing agent to 5-brom 7-chlor indoxyl carbo acid ester, which when saponified and oxidized in alk. soln. forms a tetra halogen indigo. Dye is sol. in’ boiling dimethyl anilin, in conc. H,SO, (B), when oxidized by mixed acid gives 3-chlor 5-brom isatoic acid, (m.p. 260°); a BLUE vat dye. Near S. 884—‘‘Brilliant Indigo 2B.” 949,592—Feb. 15, 1910. Eduard Miincu, Germany. (Badische.) Process of making a thioindigo dye. Sulfonated thio indigo red. Ethylene (‘‘Acetylene’’) bis thio saticyLtic acid or derivs. obtained as in 943,560 added rapidly to eight parts chlor sulfonic acid at 25-35°. Fuming sulfuric acid, trichlor-benzene with P.0., or other acid condensing agent may be used and diluting agent or flux may be present. Sulfuric acid as solvent produces a sulfonic acid or not according to temp. and speed of reaction. Rep to violet RED vat dyes or in sulfonated form violet RED acid dyes. Sulfonated S. 912—‘‘Thio Indigo Red B.” Addition to 943,560. 954,273—Apr. 5, 1910. , Gadient Enc1, Switzerland. (Basle.) Process of making fast-gray prints. (Product not claimed.) ‘Treatment of fibers dyed or printed with mono halogen, mono thio indigo. ; Fiber dyed, or printed with brom mono thio 1np1Go, from 3-oxy thio naphthene (thio indoxyl) and 1saTINn a-anilid, treated at 90° with hot water with or without soda or soap, alkali, acid, neu- 216 DIGEST OF PATENTS tral or acid salt, bichromate, etc., gives fast GRAY prints and dyeings, greenish in artificial light. Dyes may be used in combination with other dyes. S. 8099—‘‘Ciba Gray G.” Note 848,355 and 848,356. 955,410—Apr. 19, 1910. Paul Juxius, Viktor V1ILLIGER and Paul NawiAsxy, Germany. (Badische.) Tetrachlor-indigo and process of making same. _ 4.4/-5.5’-Tetrachlor indigo. 3-4-Dichlor phenyl GLycIN 2-carbo acid methylated, condensed in alc. soln. with sodium to 4.5-dichlor INDOxYL carboxylic acid ester, saponified with alkali and oxidized. Green blue powd., sol. conc. H,SO, and hot dimethyl aniline (B), oxidized with HNO, gives 4.5-dichlor isatin m.p. 247°; a green BLUE vat dye, fast to washing, light and chlorine, and unchanged in artificial light. S. 886—‘‘Brilliant Indigo G.”’ 955,699—Apr. 19, 1910. Albrecht Scumint and Karl Turrss, Germany. (Hoéchst.) Thioindigo vat dye. (Process also claimed.) Brom toluidino thio indigo, or other halo- gen nitrogen indigoes. Thio 1npIco, brominated in presence of SO,Cl, to penta or tetra brom product, then heated to 120-170°, with amins such as TOLUIDIN, anilin, or 30 per cent ammonia, with or without BEN- ZENE or other solvent and preferably with sodium acetate and copper powder to assist replacement of halogen by amin. Blue violet to blue powds., sol. conc. H,SO, and hot C,H,NO, BV-B), almost insol. in alc., C,H,, CCl,; fast violet BLUE to BLUE vat dyes. Near S. 903 or 904—‘‘Helindon Brown.” 957,683—May 10, 1910. Paul Jutius, Viktor VitLicErR and Paul Nawzasxy, Germany. (Badische.) Dichlor-dibrom-indigo and process of making same. = 4.4'-Dichlor-5.5/-dibrom indigo or 4.4’-dibrom-s.5’-dichlor indigo. 3-Chlor 4-brom phenyl Giycin 2-carbo acid, or 3-brom 4-chlor deriv., methylated in alc. sodium and condensed in acetic acid soln. to 4-chlor 5-brom 1nroxyL carbo ester which is saponified with alkali then oxidized. A green blue powd., sol. conc. H,SO, and dimethyl aniline (B); green BLuE vat dyes, fast to washing, light and chlorine, and shade unchanged by artificial light S. 887—Brilliant Indigo 4 G.” 958,464—May 17, 1910. Wilhelm Bauer and Alfred Herre, Germany. (Bayer.) Blue wat dye. A dihalogenated 2-indoxyl 4-brom 1-naphthol. Dibrom ISATIN, or other halogen or methyl substituted isatin, converted into chloride by PCI, in dry benzene soln. then added to 4-brom 1-NAPHTHOL in same solvent. The oxygen of the alfa beta group in the isatin may be replaced by easily replaceable substituents other than Cl, such as other halogens, sulfur, NH,, alkoxy, etc. Blue cryst. powds. with metallic luster, sol. hot C,H,NO, (B) in conc. H,SO, (GB); BLUE vat (Y) dyes, especially fast to Cl. Near S. 985—‘‘Halogen-Alizarin Indigo 3 R.”’ Note 958,465 and for non halogenated dye, 999,439. 958,465—May 17, 1910. Wilhelm Bauer and Alfred Herre, Germany. (Bayer.) Blue wat dye. Same constitution as 958,464 with Cl for Br in naphthol rest. Dibrom ISATIN, or other, in dry benzene soln. converted to chloride by PCl, then mixed with soln. of 4-chlor 1-NAPHTHOL, also in dry benzene. Dark blue cryst. powds., of coppery luster, sol. hot C,H, or C,H.NO, (B), in conc. H,SO, (GB); siug vat (Y) dyes, especially fast to Cl. Near 894—‘‘Halogen-Alizarin Indigo 3R.” Note 958,464 and 999,439 for non halogenated dye. Oa 959,617—May 31, 1910. Albrecht Scumipt and Ernst Bryx, Germany. (Héchst.) Vat dye and process of making. 7.7’-Diamino thio indigo or its 5.5’-dichlor deriv. 2-Nitro phenyl thio Giyconic acid or halogen derivs. condensed with SO,Cl, to 7.7/-dinitro thio INDIGO, or derivs., then reduced with Na,S with or without sulfur present, or ‘with other reducing agents. Black to dark blue powds., insol. in aq., alk., dil. acid or alk., sol. conc. H,SO, (B), diff. sol. hot C,H.NO, (VBr-V); dark BLUE to BLACK vat dyes. S. 921—‘‘Helindon Gray 2B.” a ae ae ee ed 960,098—May 31, 1910. : Hermann Krart, Switzerland. (Basle.) Green vat dye and process of making same. Brom b-naphthindol indigo. Brom b-NAPHTHISATIN Chloride, or other, and INDOXYL or ACETINDOXYL, heated in dry alcohol soln. with dry anhyd. Na,CO;. Dye may be further brominated in nitrobenzene by heating to GROUP VII.—INDIGO AND INDIGOID my 100-120° with Br, giving dye of hluer shade and faster to washing and Cl. Green black powds., sol. conc. H,SO, (G); GREEN vat (O) dyes fast to washing, light and chlorine. Note: One half the molecule is like S. 891—‘“‘Ciba Green G.”’ 960,671—June 7, 1910. Martin Mucpan and Willy Herrmann, Germany. (Cons. Elek.) Process of making indoxyl, &c. Indoxyl or leuco indigo. Phenyl GLYcIN potassium, or other aryl glycin, mixed with Ca-Si alloy, or other, added to caustic melt at 220-250°. Indoxyl may be isolated as such or oxidized at once to indigo. S. 874—“Indigo.” 961,396—June 14, 1910. Wilhelm Bauer and Alfred Hrerrt, Germany. (Bayer.) Vat dye. a-Anthrol dibrom indole, homologs and other halogen derivs. IsaTin, treated with PCl, in benzene soln. to form chloride, added to a-AntTHROL, also in dry benzene, or acetic anhyd. soln. Dibrom isatin and other isatin derivs. in which the oxygen of the alfa keto group is replaced by easily replaceable substituents, halogen, sulfur, NH,, alkoxy, etc., and anthrol or other comps. having a free ortho position to the hydroxy group are claimed. Dye- stuffs are dark blue cryst. powds., sol. hot C,H,NO, (B), in conc. H,SO, (BrG); BLuE to green BLUE vat (OY) dyes, especially fast to Cl. S. 893—‘‘Alizarin Indigo O.’’ Note 999,439 (Elbel and Wray) which employs naphthol instead of anthrol. Also 961,397, 961,398, 961,399, 980,140, 998,596, 1,001,919, 1,005,140, 1O05,141, 1,101,778. 961,397—June 14, 1910. Wilhelm Bauer and Alfred Herre, Germany. (Bayer.) Vat dyestuff. Dibrom indole-naphthol. Dibrom 1saT1N, converted to chloride by PCl., then combined with 1-NaPHTHOL in dry benzene soln. Other substituted isatin derivs. containing halogen in the nucleus and in which the oxygen of the alfa keto group is replaced by easily replaceable substituents such as halogen, S, NH,, alkoxy, etc., are claimed. Dark blue cryst. powd., sol. hot C,H,NO, (B); BLUE vat dyes, fast to chlorine. S. 895—‘‘Alizarin Indigo 3 R.” Addition to 961,396. $61,398—June 14, 1910. Wilhelm Bauer and Alfred Herre, Germany. (Bayer.) Blue dye. Dibrom indole-4-methoxy naphthol. 7-Methyl 1saT1n, converted to chloride by PCl,, then combined with 4-ethoxy NAPHTHOL in dry benzene. Same general claims as 961,396 and 961,397. Dark blue cryst. powds., sol. hot C,H,NO, (B); violet BLUE vat (Y) dyes, especially fast to Cl. Near S. 895—‘“‘Alizarin Indigo 3 R.” 961,399—June 14, 1910. Wilhelm Bauer and Alfred Herre, Germany. (Bayer.) Blue dye. Dibrom indole-4-ethoxy naphthol. Dibrom 1saTIN, converted to chloride by PCl,, then combined with 4-ethoxy NAPHTHOL in dry benzene. Same claims as 961,396 et seq., and same properties for dyes. Buiur vat dyes, fast to Cl. Near S. 895—‘‘Alizarin Indigo 3 R.” 963,377—July 5, 1910. Otto LigEBKNECHT, Germany. (Roessler.) Manufacture of indigo leuco bodies. Indoxyl or leuco indigo, homologs and derivs. Phenyl ciycin, K salt, heated in alkali melt with alkali metal (Na) and ammonia (alkali amid formed in situ). Aromatic comps. capable of forming indigo leuco bodies in an alkali melt are claimed, together with use of alkali metal in melt and addition of NH, to form an alkali amid which eliminates water from the mass. Brive vat dyes. S. 874—“Indigo.” 963,813—July 12, 1910. Albrecht Scumipt and Ernst Bryx, Germany. . (Hochst.) Red halogenized dye and process of making. MHalogenated 6.6’-diethoxy thio indigo. 6.6’-Diethoxy thio 1np1co allowed to stand or gently heated with halogen or SO,Cl,, diluted with CCl,, or C,H,NO,, etc., and separated by filtration. Other 4-oxy ethers of this indigo or 218 DIGEST OF PATENTS their leuco comps. are claimed, with use of low temps. Dyes are insol. in aq., dil. acids, or alk., alc. and ether, sol. in hot C,H,NO, (OR) in conc. H,SO, (B); fast RED vat (Y) dyes. Near S. 914—‘“‘Helindon Orange D.” Addition to 872,585 and 812,508. 965,170—July 26, 1910. Karl Exper, Germany. (Kalle.) Process of condensing reduction products of acenaphthene-quinone, &c. (Product also claimed.) Leuco thio indol hydro acenaphthene indigo. ACENAPHTHENE quinone ground with alcohol then slowly added to Fe in dil. acetic acid, warmed to 80-90°, filt., purified and refluxed with 3-oxy thio NAPHTHEN#, indoxyl, or derivs. in alk. alcohol soln., excluding air. Patent claims use of mild reducing agents to form from the quinones water soluble bodies whose alkali salts will condense with oxy thio naphthene. A color- less or almost colorless powd., insol. aq., diff. sol. alk., sol. dil. alk. (RV) which soln. is decomp. by acids; BLUE vat (RV) dye. Near S. 907—‘‘Ciba Scarlet G.”? Note 891,690 for unreduced dye of similar constitution. 968,697—Aug. 30, 1910. Albrecht Scumipt, Ernst Bryk and Robert Voss, Germany. (Héchst.) Vat dye and process of making same. Halogen indoxyl thio indigo, thio indirubin, or other. 4-Acet amino thio saLicyL acetic acid or 6-amino oxy thio naphthene and 1saTIN, or brom nitro amino isatin, heated in nitrobenzene soln. to 160° with bromine. Other amino-oxy thio naphthenes and other derived isatins are claimed. Products are dark powds., insol. agq., alc., C,H,, ether, dil. acids and alks., sol. in conc. H,SO, (BrV-B), diff. sol. in hot C.H,NO,, C,H.NH,, etc; yellow BROWN, BROWN or GRay vat (YB) dyes. S. 902—‘‘Helindon Brown 2 R.’”? Schulz bases three dyes, 902, 903 and 904 on this patent. 980,140—Dec. 27, 1910. Wilhelm BaveEr and Alfred Herre, Germany. (Bayer.) Blue wat dye. a-Anthrol dichlor indole. Dichlor 1sat1n converted to chloride by PCI, in dry chlor benzene soln., then combined with a-ANTHROL, also in dry chlor benzene. A blue cryst. powd., sol. hot C,H, (B), in conc. H,SO, (olive); a BLUE vat (O) dye. S. 893—‘“‘Alizarin Indigo G.” Addition to 961,396. 984,442—Feb. 14, 1911. Arnold Rantyen, Germany. Process for preparing indoxyls and indigo by electrolysis. Indoxyls and indigo by electrolysis. Phenyl GLycin, phenyl hydantoin, homologs, salts, ethers, acetyl derivs., etc., electrolyzed at 220-260° in caustic alkali soln., with or without diaphragm or flux and in vacuo if preferred, . with cell as cathode and carbon as anode, using current of 4-6 volts and 2-5 amps. per sq. dem. During electrolysis ammonia or hydrazin vapor is passed through the mass to form metallic amids or imids from metal set free. Reaction should be rapid at first to remove free aq. Yield 70 per cent and upward. S. 874—‘“Indigo.” 985,767—Mar. 7, 1911. Wilhelm Baver, Alfred Herre and Rudolf Mayer, Germany. (Bayer.) Vat dye. Halogen naphthindol hydroxy a-b-anthraquinonyl compound. Brom b-NAPHTHISATIN heated with PCl, in dry chlorbenzene to form chloride then added while hot to @ANTHROL in same solvent. General claims same as with 961,396 et seq. Dark blue cryst. powds., sol. hot C,H,NO, (B); Gray to BLACK vat dyes, fast to Cl. Note 958,464 and 985,768,-69,-70. 985,768—Mar. 7, 1911. Wilhelm Bauer, Alfred Herre and Rudolf Mayer, Germany. (Bayer.) Vat dye. Dihalogen naphthindol hydroxy a-b-anthraquinonyl compound. Dibrom b-NAPHTHISATIN converted to chloride by PCI, in dry chlorbenzene soln. then added to a-ANTHROL in same solvent. Same general claims as 985,767. Dark blue cryst. powds., sol. hot C,H,NO, (B), in conc. H,SO, (BBk); blue Gray to BLAcK vat dyes, fast to Cl. Note 958,464 and 985,767. GROUP VII.—INDIGO AND INDIGOID 219 985,770—Mar. 7, 1911. Wilhelm Bauer, Alfred Herre and Rudolf Mayer, Germany. (Bayer.) Vat dyestuff. Dihalogen naphthindole 4-halogen 1-naphthol. Dibrom b-NAPHTHISATIN converted to chloride by PCl, in hot dry chlorbenzene then added hot to 4-brom 1-NAPHTHOL in same solvent. General claims similar to 985,767 and products with similar properties. Gray-BLUE to BLACK vat dyes, fast to Cl. 985,769—May 7, 1911. Wilhelm Baver, Alfred Herre and Rudolf Mayer, Germany. (Bayer.) Vat dyestuff. Halogen naphthindole 4-halogen or ethoxy 1-naphthol. Brom 6-NAPHTHISATIN converted to chloride by PCI, in dry chlorbenzene soln. then added while hot to 4-brom I-NAPHTHOL in same solvent. Same general claims as in 985,767. Dark cryst. powds., sol. hot C,H,NO, (B), in conc. H,SO, (BG-Br); Gray to BLAcK vat dyes, fast to Cl. Addition to 985,767. 9$94,988—June 13, 1911. _ Gadient Ener and Jaroslav Frounicu, Switzerland. (Basle.) Yellow-colored derivatives of indigo and process of making same. Benzyli- dene substituted for two N hydrogens of indigo forming additional heterocylic ring, and sulfo derivs. Indigo, heated to 150-160° in nitrobenzene soln. containing Cu powder, with BENZOYL chloride. Soln. in fuming H,SO, yields sulfo dye. Instead of Cu, Co, Hg, or Ni salts such as ZnCl,, AICl,, may be used as condensing or contact substance. As solvent nitrobenzene may be omitted or replaced by naphthalene, xylene, etc., and for benzoyl chloride the trichloride or other haloid of an aromatic acid. Green to brown yellow powds., insol. aq., diff. sol. in alc., ligroin, easily sol. hot C,H,NO, (Y), in conc. H,SO, and oleum (Br), on diln. (Y); YELLOW acid dyes. S. 889—“Indigo Yellow 3G Ciba.” Note 997,766 and 1,026,574. $97,260—July 11, 1911. Wilhelm Baver and Alfred Herre, Germany. (Bayer.) Vat dye. a-b-Anthraquinonyl thio indoxyl compound and derivs. Dimethyl 4’-amino a-anilino thio 1Inpoxyr, from nitroso dimethyl ANILIN and thio INDOXYL in glac. acetic soln. heated in water bath with a-anruHrot. Halogen derivs. and other aryl amins claimed. Violet powds., sol. hot C,H, (VR-R fluor), in conc. H,SO, (G); viotet vat dyes. $897 ,766—July 11, rort. Gadient Ener and Jaroslav Frouuiicu, Switzerland. (Basle.) Halogenized vat dyestuffs and process of making same. Halogenated Indigo Yellow 3 G Ciba, S. 889 or derivs. Inpico substituted in two N. hydrogens by benzylidene (see 994, 988) by action of BENZOYL chloride, mixed in a diluent, such as sulfuric acid or nitrobenzene, with bromine at ordinary temp. then heated to 170-175°. Other halides of aromatic acids are claimed. Products are yellow powds., containing 33 per cent Br., insol. in aq., diff. sol. in alc., more easily in C,H,NO, (Y), sol. in conc. H,SO, (BrR), in oleum (BR); YELLow vat (BR) dyes, fast to washing, light and Cl. S. 890—‘“‘Ciba Yellow G.” 998,596—July 25, 1911. Wilhelm Bauer, Alfred Hrerre and Rudolf Mayer, Germany. (Bayer.) Vat dye. Oxy acenaphthene 5.7-dibrom indoxyl compounds resembling indigo. Dibrom 1satTIn converted into the chloride by PCI, then added to hot soln. of 4-oxy Acz- NAPHTHENE in dry benzene. Other derivs. of isatin may be used with any easily replaceable alfa-keto group. Claims similar to 961,396. S. 894—‘“‘Alizarin Indigo B.” $99,439—Aug. 1, 1911. Karl Erse, and Edward Wray, Germany. (Kalle.) Vat-dyeing coloring-matter. Dibrom indoxyl 1-naphthol compound resembling indigo. 4-Methoxy I-NAPHTHOL or other oxy derivs of cylic hydrocarbons, combined with ISATIN a-anilid or derivs. to form an indigoid dye, which is added slowly at ordinary temp. to a conc. sulfuric acid bromine mixture, (or SO,Cl,). Less Br is required when components already 15 220 DIGEST OF PATENTS contain bromine or other substituents. Blue powd., insol. aq. and alc., sol. H,SO, (GB), in hot C,H,NO, and C,H,NH, (B); Biur vat (Y) dyes. S. 893—‘“Alizarin Indigo G.”’ Although patent reference in Schulz is to this dye, the formula there given belongs to 961,396 by Bauer and Herre. S. 895—Alizarin Indigo 3R is correct Schulz number. 1,001,457—Aug. 22, ro1t. Karl ScHIRMACHER and Richard Lrorotp, Germany. (Hdchst.) Green to black dyestuff. 6.6’ Dialkyl dithio deriv. of indigo. 5-Ethyl thio phenyl GLycIN 2-carbo acid, from 4-ethyl thio ANTHRANILIC acid and chlor ACETIC, condensed in boiling acetic anhyd. Other s5-alkyl thio derivs. of phenyl glycin carbo acid are included in claims. Products are green black powds., sol. conc. H,SO, or glac. acetic (G), sol. in ale. or C,H,NO, (dichroic BrR-G); GREEN to BLACK vat (Y) dyes. 1,001,919—Aug. 29, 1911. Wilhelm Bauer, Alfred Herre and Rudolf Mayer, Germany. (Bayer.) Vat dye. Dibrom indoxyl acenaphthenone indigo. Dibrom IsaTIN or derivs., converted to chloride by PCI; in dry benzene, then condensed with ACENAPHTHENONE in dry benzene soln. Claims similar to 961,396. Dyes are red brown cryst. powds., sol. in hot C,H, (BR), in cold conc. H,SO, (G), in hot sulf. (B); violet rep to VIOLET vat (V) dyes. 1,005,140—Oct. 10, 1911. Wilhelm Baver, Alfred Herre and Rudolf Mayer, Germany. (Bayer.) Wat dye. 2-b-Naphthindoxyl-4-brom-1-naphthol compound resembling indigo. b-NAPHTHISATIN converted to chloride by PCI; in chlor benzene, then condensed with 4q- brom I-NAPHTHOL in same solvent. Claims similar to 961,396 with naphthisatin instead of isatin derivs. Dark cryst. powds., sol. hot C,H,NO, (B); Gray to BLacK vat (Y) dyes, fast to Cl. 1,005,141—Oct. 10, 1911. Wilhelm Bauer, Alfred Herre and Rudolf Mayer, Germany. (Bayer.) Vat dye. 2-a-Naphthindoxyl a-anthrol indigo. b-NAPHTHISATIN converted to dichloride by PCI, in chlor benzene soln. condensed with a- ANTHROL. Claims similar to 961,396 with naphthisatin derivs. instead of isatin. Violet cryst. powds., sol. hot C,H,;NO, (B), in conc. H,SO, (B); violet Gray to red BLack vat (Y) dyes, fast to Cl. 1,012,363—Dec. 19, 1911. Tudwig Kars, Germany. (Badische.) Indigo coloring-matter and deriwatives thereof and process of making them. Dehydro indigo or derivs. as stable, easily sol. bisulfite compounds. Inpico, halogen compound or other, oxidized in dry benzene soln. by PbO, with a little glac. acetic acid and dehydrating agent to form dehydro INnpiIGo or its diacetate which can be halogenated at once, or later. Bisulfite compound is formed by adding powd. dehydro indigo to cone. soln. of bisulfite (40°). Other dry solvents, CHCl, or C,H;NO,; other oxidizing agents, MnO,, permanganates, etc. and soluble dehydrating agents, such as anhydrous acids, glacial acetic, benzoic or HCl may be used. Products are specially adapted to light effects, printing, etc.; BLUE vat dyes. Near S. 874—“Indigo.” 1,015,495—Jan. 23, 1912. Joseph Kortscuret and Andre Barrer, France. (Soc. Chim.) Process of producing indigo-o-nitrophenyl-lactic acid ketones. Indigo 2- nitro phenyl lactic acid ketones. 2-Nitro PHENYL nitro methane, homologs or derivs, in aq. acetone soln. containing NaOH cooled, powd. KMnO, added slowly, filtered to remove MnO, and ketone in soln. converted to indigo with alkali. S. 874—“‘Indigo.”’ 1,025,138—May 7, 1912. Erwin Horra, Germany. (Hochst.) Violet-blue dyestuffs. 4.4’-Dimethyl 5.5’-dihalogen 7.7’-dialkoxy thio indigo. 6-Methoxy 4-chlor 3-methyl thio ciyconic acid, 1 part, condensed in 5 parts chlor sulfonic acid, by stirring at ordinary temp., poured on ice, filt. and purified by boiling NaOH. Other GROUP VII.—INDIGO AND INDIGOID 221 halogen and alkyl derivs. claimed. Violet blue powds., insol. aq., almost insol. alc., sol. C,H,NO, (V), in conc. H,SO, (G); violet sug vat (V) dyes. S. 920—“Helindon Violet BB.” Note the isomeric dye with chlorine in 6.6’ positions is of a violet red color. 1,025,174—May 7, 1912. Robert WeELDE and Benno Homoika, Germany. (Hochst.) Blue vat dyestuff and process of making same. Indoxyl oxy anthranol indigo. IsaTin a-anilid, or other alfa substituted isatin, treated in benzene soln. with PCI; to form chloride then condensed with a-oxy ANTHRANOL (produced by gentle reduction of a-oxy anthra- quinone) by heating to 100° in acetic anhyd. soln. Dyestuffs are blue cryst. powds., insol. in aq., slightly sol. in alc., easily sol. in xylene, phenol, C,H,NO, (B), in conc. H,SO, (V); BLuE vat (OY) dyes. S. 896—‘‘Helindon Blue 3 GN.” Note this patent claims a process previously used by Bauer and Herre (961,396 et seq.) and by Elbel and Wray (999,439). 1,028,911—June 11, 1912. Albrecht Scumipt and Karl Tuirss, Germany. (Héchst.) Reddish-blue vat dyestuffs and process of making same. Tribrom-7-methyl in- dirubin. IsaTin condensed with 7-methyl 1npoxyLt and halogenated in nitrobenzene soln. 2 to 5 atoms halogen being added. Other solvents and varying amounts of bromine or chlorine are employed. Products are blue violet powds., insol. aq., very diff. alc., diff. sol. CHCl, (V), sol. in C,H,NO, and C,H,NH,, diff. sol. H,SO, (dark G); violet BLUE vat (Yt) dyes. S. 898—‘“‘Helindone Violet D.” 1,042,679—Oct. 29, 1912. H. S. A. Hout, Germany. (Badische.) Halogenized indigo compounds and process of making such bodies. (Process only claimed.) Tri or tetra chlor dehydro indigo salts. Dehydro 1npico, a salt homolog or deriv., or the indigo itself, chlorinated in glac. acetic soln. in absence of comp. capable of fixing HCl but in presence of organic acid capable of forming salt with halogenized dehydro indigo, then reduced. Other solvents, such as nitro- benzene, acetyl chlorid, CCl,, etc., and other halogens or halogen derivs., such as sulfuryl chlor- ide in different proportions, may be used. A BLUE vat dye. Near S. 885—‘‘Brilliant Indigo, etc.” 1,043,468—WNov. 5, 1912. Albrecht Scumipt, Heinrich R6ssNER and Hans BatHorn, Germany. (Hochst.) Manufacture of brominated blue indigo dyestuffs. (Product also claimed.) Bro- minated indigo containing at least 4 atoms Br. Dibrom 1npico or dichlor indigo of 856,776, converted into green black perbromid as in 918,920, filtered from sulfuric acid, pressed and added to a conc. bisulfite soln. diluted with ice. Pptd. dye contains 55-58 per cent bromine (4 atoms at least), sol. conc. HOO GB); oxidized in glac. acetic by HNO, yields 5.7-dibrom isatin, m.p. 249-250°; BLUE vat dyes of green hue by artificial light. Leuco products are gray green, insol. in aq., sol. in dil. caustic (YBr). S. 881 to 887. Note 856,776 for tetrabrom indigo. 1,043,682—Nov. 5, 1912. Gadient Ene, Switzeriand. (Basle.) Colored condensation products and process of making same. Diphenyl diacetoyl indigo condensate with two additional closed six membered rings joining CO of one indoxyl with N of the other. ; Inp1co and 2 mols. PHENYL acetic acid chloride, refluxed till HCl ceases to evolve, diluted with nitrobenzene or xylene and again boiled to close rings. Halogen or alkyl substituted in- digoes up to six or more substituents, and any other halide of an arylated fatty acid may be employed. Dyes may be sulfonated. Red to violet powds., insol. in aq., sol. hot xylene or C,H,NO, (BR-Y fluor), sol. conc. H,SO, (YO-O), pptd. on diln. (R-V); vaRI-coLoRED vat or acid dyes. : 1,050,179—Jan. 14, 10913. August Stock, Germany. (Hochst.) Violet tetrachlorindigo and process of making same. _5.5’.6.6’-Tetra chlor indigo. 4.s-Dichlor 2-nitro BENZALDEHYDE obtained by nitrating 4.5-dichlor BENZALDEHYDE, mixed in acetone soln. at 5° with aq. sod. sulfite to form dichlor phenyl lacto methyl ketone, then 222 DIGEST OF PATENTS . calcined Na,CO, added and heated to 30-40°, Violet powd., insol. aq., very slightly sol. ace- tone and CHCl, (V), in glac. acetic (B), in cold conc. H,SO, (dull YGy) turning (G) when heated; a red vioLeT vat (Y) dye. Isomer of S. 885—‘‘Brill. Indigo.” 1,051,856—Feb. 4, 1913. Wilhelm Baver, Alfred Herre and Rudolf Mayer, Germany. (Bayer.) Vat dye. = 5.7-Dibrom indoxyl 3-carbazole compound, homologs and derivs. 5.7-Dibrom IsaTIN converted to chloride by PCI; in dry benzene suspension and added to hot soln. of CARBAZOLE in same solvent. Other isatin derivs. in which the oxygen of the alfa keto group is replaced by easily replaceable substituents (halogen, S, NH,, alkoxy) and other carbazol comps. may be used. Dyes are cryst. powds. with metallic luster, sol. hot. C,H,;Cl (V); RED to VIOLET vat (Y) dyes, fast to chiorine. Addition to 985,767. 1,061,781—May 13, 1913. Albrecht Scumipt and Karl Turgess, Germany. (Hoichst.) Greenish-blue hexabromindigo. Hexabrom indigo. Inp1G0, or halogenated derivs., heated with excess Br to 100—120° under pressure, excess Br removed by distn., air, etc. and perbromide pptd. by bisulfite as hexabrom indigo. Halo- genation can also take place in fuming sulfuric (2-5 per cent anhyd) or in chlor sulfonic. Product is insol. aq., sol. conc. H,SO, (B), in cold C,H,NH, (GB-dark B), oxidized in glac. acetic by HNO, gives 4.5.7-tribrom isatin, m.p. 257°; a green-BLUE vat dye. S. 883-—‘Indigo M.L.B./6B.”” Note 1,070,541. 1,070,541—Aug. 19, 1913. Albrecht Scumipt and Karl Tuiess, Germany. (H6chst.) Pentabromindigo. 4.5.7.5'’.7’-Penta brom indigo 59.8 per cent Br (theory 60.88 per cent). Inp1co or brom derivs., dissolved in 10 parts liquid. bromin while cooling, then gently heated to 80° under pressure, excess Br removed and resulting penta brom indigo heated with soln. of bisulfite, etc. Sulfuric acid soln. of Br may be used and preferably halogen carrier such as iodine. Dark blue powd. sol. in conc. H,SO, and cold C,H,NH, (B), much more sol. in organic solvents than tri and tetra derivs., on oxidization gives 4.5.7-tri- and 5.7-dibrom isatin; a BLUE vat dye with green tint perceptible by artificial light. S. 882—“Indigo, M.L.B. 5B.” Note 1,061,781. 1,074,405—Sept. 30, 1913. Wilhelm Bauer, Alfred Herre and Rudolf Mayer, Germany. (Bayer.) Vat dye. 5.7.6’-Trichlor indirubin or other. 5.7-Dichlor 1saATIN or deriv. in hot glac. acetic acid to which 6-chlor 1npoxyL or derivs. in same solvent then conc. HCl are added and whole heated. Red brown crysts., sol. hot C,H,NO, (R), in conc. H,SO, (BrR-RV); rep vat dyes, fast to Cl and light. Near S. 897—‘‘Ciba Heliotrope B.” ; 1,074,850—Oct. 7, 10913. Gadient Enc1, Switzerland. (Basle.) Vat dyestuffs of the indigo series and process of making same. Halogenated leuco form of S. 890. Inp1co condensed with sBenzoyut chloride, halogenated, then boiled with NaHS, or other inorganic solvent that is water miscible (alcohol, etc.) in absence of caustic alks. Orange to orange brown powds., insol. aq., diff. sol. hot alc., more easily in hot C,H,NO, (BrY), in conc. H,SO, (RBr), pptd. on diln.; orange YELLOW vat (R) dyes, fast to washing, light and chlorine. Near S. 890—‘‘Ciba Yellow G.’? Note 994,088 and 997,766 (S. 890) for first part of process. Treatment with NaHS claimed above. 1,081,898—Dec. 16, 1913. Gadient Enc1 and Jaroslav Froéuuicn, Switzerland. (Basle.) Orange vat dyestuffs and process of making same. Amino thio indoxyl acenaph- thene quinone. ACENAPHTHENE quinone or other, condensed with 6-amino thio INDOxyL or its carbo acid, product added at O° to a mixture of 97 per cent sulfuric and Br then heated to 20-25°. Heat- ing in nitrobenzene soln. or other with Br to 200-220° gives halogenated product. Brown to brown yellow powds., insol. aq., sol. in conc. H,SO, (B); ORANGE to brown ORANGE vat (VBr) dyes. S. 911—‘“‘Ciba Orange G.” p ¢ 1 & a ‘ % 2 GROUP VII.—INDIGO AND INDIGOID 223 1,101,778—June 30, 1914. Wilhelm Bauer, Alfred Herre and Rudolf Mayer, Germany. (Bayer.) Vat dyestuffs, o9-Chlor naphthindoxyl a-anthrol indigo. g-Chlor NAPHTHISATIN or other halogen deriv. of same, converted to chloride by PCI, in chlor benzene, then condensed with a-ANTHROL in same solvent. Dark powds., sol. conc. H,SO, (B-G), sol. hot C,H;NO, (GB); rEp to BLUE to GREEN fast vat (RBr) dyes. Addition to 961,396. 1,108,056—Aug. 18, 1914. - Edward Wray, Germany. (Kalle.) Manufacture of vat dyestuffs. (Product also claimed.) 5-Chlor indoxyl 2’.1’-pheno s’-oxy 6’-naphthcarbazole, homologs and derivs. 5-Chlor 1satin 4/-chlor a-anilid, or other reactive isatin a-deriv., condensed in acetic an- hyd. soln. with 2.1-pheno 5-oxy NAPHTHCARBAZOLE (from PHENYL hydrazin and 2.5-amino sulfo NAPHTHALENE fused with alkali) or other o-phenoxy carbazoles. Dyes are powds., insol. in usual solvents, sol. in conc. H,SO, (GB); BLuE to vioLET vat (Y) dyes. Note 1,108,057. 1,108,057—Aug. 18, 1914. Edward Wray, Gerimany. (Kalle.) Manufacture of vat dyestuffs. (Product also claimed.) Thio indoxyl 2.1-phen 5-oxy naphthcarbazole indigo. 2.1-Pheno 5-oxy NAPHTHCARBAZOLE or other phenoxy naphthcarbazole, dissolved in glac. acetic containing sodium acetate to which is added thio 1npoxyL dibromide, or other alfa derivs of thio indoxyl in small portions. Products may be halogenated. ‘They are red violet powds., insol. aq., slightly sol. alc., sol. hot C,H,NO, and quinolin, in conc. sulf. (G); red violet fast vat (Y) dyes. Addition to 1,108,056. 1,122,790—Dec. 29, 1914. Edward Mtncn, Germany. (Barlische.) Vat coloring-matters and process of producing them. Indoxyl perimidin (or thio perimidin) indigo. Isatin chloride or other isatin a-halogenid (from 1sat1n and PCI.) in benzene soln. added to boiling benzene soln. of PERIMIDIN (peri-napthimidazole) thio urea of same, or other. See table of components and properties. Blue tinted powds., sol. conc. sulf. (BG), sol. C,H,NO, (BG-VB); blue crEEN to violet BLUE vat (Y) dyes. 1,144,577—June 29, 1915. Edward Wray and Fritz Hrss, Germany. (Kalle.) Manufacture of vat dyestuffs. (Products claimed.) 2-Indoxyl-6-benzoyl amino-1-naph- thol indigo. 6-Benzoyl AMINO I-NAPHTHOL 5.5’-dioxy 2.2/-dinaphthyl urea or other acidyl amino naph- thols, and 1saT1IN a-anilid, or other alfa isatin deriv. boiled together in acetic anhyd. Dark blue to black powds.; BLUE to violet BLACK vat (Y) dyes. Note 1,147,778 and 1,157,485 for related dyes. 1,147,778—July 27, 1915. Wilhelm Bauer and Alfred Herre, Germany. (Synthetic.) Red vat dye. Dichlor indoxyl phenyl a-indanon indigo. 5.6-Dichlor 1sat1n a-anilid, or other halogen deriv. of isatin in which the alfa keto oxygen is replaced by a mobile substituent, heated in acetic anhyd. with 3-phenyl INDANONE, or other aryl indanon. Reddish powds., sol. conc. H,SO, (B); RED to vioLet fast vat (Y) dyes. Note 1,144,577 and 1,157,485 for related dyes. 1,157,.485—Oct 19, 1915. : Edward Wray, Germany. (Kalle.) Manufacture of black dyestuffs. (Product claimed.) Chlor indoxyl oxy naphtho-car- bazole indigo. 5-Chlor 1satin 4’-chlor a-anilid, boiled in acetic anhyd with 5-oxy 2.1-NAPHTHCARBAZOLE. Other mono chlor isatin alfa derivs. are claimed. Black powds., insol. in aq. and alc., sol. hot C,H,NO, and quinolin (B), in cold sulf. (slate B); fast BLackK vat (Y) dyes. Note 1,108,056, 1,108,057, 1,144,577 and 1,147,778. 1,211,413—Jan. 9, 1917. Lee E. H. Const, Michigan. (Dow.) Method of making indoxyl and derivatives. Indoxyl or leuco indigo, and derivs., with improved yields. 224 DIGEST OF PATENTS Phenyl ciycin, phenyl glycocol, etc., fused with caustic alkali, alk. earth oxide, and metallic sodium, present as such, and melt passed into water out of contact with air. The proportions of the ingredients in the melt are important. Yields are 65-75 per cent. S. 874—“‘Indigo.”’ 1,211,413—Jan. 9, 1917. Lee E. H. Cont, Michigan. (Dow.) Re. 14,364—Sept. 25, 1917. Method of making indoxyl and derivatives. Phenyl ciycin, phenyl glycocol or similar body, added to hot melt consisting of NaOH and KOH in molecular proportions, also of quicklime, or other alk. earth oxide and metallic Na. The latter must be present as such in the fused mass. Melt is: maintained at 250° for half hour, then poured into water out of contact with air. S. 874—“‘Indigo.” Note 617,652, 727,270, and 756,171. 1,243,170—Oct. 16, 1917. ‘Richard Herz, Germany. Vat dyes and process of making same. Thio indigo and derivs. AniL1In HCl, or other aromatic amin, dried, ground, and heated with SO,Cl, to 50-70° until it will not diazotize, ppt. dried in vacuum, heated in alc. NaOH containing sod. hydrosulfite until aq. soluble, cHLOR ACETIC in alk. soln. added and heated to 70-80°; product diazotized, combined with Cu(CN),, nitrile saponified, ring closed by heating in Na,S soln, boiled with acids and oxidized. Dark colored powds., insol. aq., dil. alks. and acids, sparingly sol. in alc., hot C,H, and other organic solvents, diff. sol. C,H;,NO, (R-V—Br); ORANGE, RED, VIOLET, BROWN and BLACK vat (Yt) dyes, fast to washing, scouring, bowking and Cl. Note 1,243,171 for more specific claims. 1,243,171—Oct. 16, 1917. Richard Herz, Germany. Vat dyes and process of making same. Thio indigo. 2-or 3-TOLUIDIN or 4-xylidin, subjected to same process as anilin HCl in 1,243,170. Red powd., sol. hot C,H,NO, (BR), in warm conc. H,SO, (dark G); a pale rep vat (Y) dye of great purity of shade and fastness. 1,253,252—Jan. 15, 1918. Michael Karpos and Paul Nawrasxy, Germany, (Badische.) Bluish-green vat dyes and process of making them. Diaceanthrene quinone oxim indigoes. ANTHRACENE 1.9-dicarbo acid methyl imid (from METHYL amin and ANTHRACENE-1.9-di- carbo anhyd.) heated in KOH at 210°, melt dissolved and oxidized with air. The hydrogen of the imid must be substituted before alk. fusion, but dye can be alkylated or halogenated after it is formed. Blue GREEN fast vat (R-V) dyes. Note that specific claims are given above while generic claims may be found in 1,216,134. 1,266,092—May 14, 1918. Wilhelm Baver and Alfred Herre, Germany. (Synthetic.) Yellowish-brown vat dyes. 6-Amino 5.7’-dichlor indirubin. 5.7-Dichlor 1saATIN, indoxyl or acidyl derivs., and 6-nitro diacetyl Inpoxyzt heated in glac. acetic containing HCl. Product may be halogenated. In the vat it is converted into the amino comp. Nitro products are violet crysts., sol. conc. H,SO, (BV); yellow BRown vat dyes, fast to washing, light, Cl. The amino derivs. are dark brown powds., insol. in usual organic sol- vents, sol. conc. H,SO, (RV). Near S. 897—‘“‘Ciba Heliotrope B.’’ 1,293,680—Feb. 11, 1910. Emmanuel A. Bourcart, France. (Comp. Paris.) Manufacture of indoxyl, its homologues and their derivatives. Higher yields in indigo manufacture. To a molecular mixture of NaOH and KOH, in an autoclave, sodamid, or other water de- composing agent, is added, and pressure raised to 6-10 atmos. by means of NH, or C,H,NH, vapors. At 180° one part phenyl glycin or other aryl glycin is added to the fused mixture, keeping temp. below 190°. When NH, ceases to evolve, melt is dissolved in ice water, and indigo pptd. 1,322,052—Nov. 18, 1919. Ralph S. Porrer, New Jersey. (Barrett.) Process of producing anthranilic acid. Anthranilic acid from phthalimid by more economical process. PHTHALIMID is converted to ANTHRANILIC acid, Na salt, by NaOCl and NaOH, the carbonate in soln. recovered as ppt. of bicarbonate by addition of Co, gas, filtered, and free anthranilic GROUP VII.—INDIGO AND INDIGOID 225 acid pptd. from filtrate by excess SO, gas, which will not cause loss by forming soluble salts with product. t,412,038—Apr. 11, 1922. Maurice BouviEr, France. (Soc. Chim.) Dyestuffs of the indigo series. Dibrom 5.5’-dimethyl indigo. 5.5’-Dimethyl 1np1co, derived from a) 2-nitro 5-methyl BENZALDEHYDE by condensing with ACETONE in an alk. medium, or b) by alk. melting of 4-tolyl glycin, is halogenated by direct treatment with halogen in hot C,H, soln., in conc. H,SO,, or in cold SO,Cl, A dark blue powd., sol. in conc. H,SO,, cold C,H,NH, and alc. (G), sol. in hot C,H.NH,, in C,H,NO,,CHCI,, acetone, C,H,, CCl,, CS, and acetic acid (B); a sLuE vat (GY) dye, which unlike unhalogenated dimethyl indigo, gives deep, sharp shades. 1,414,335—May 2, 1922. Maurice Bouvirer, France. (Soc. Chim.) Process for obtaining halogen derivatives of indigo and of its homologues. Improved chlor sulfonic acid process for halogenating indigo. 5.5’-Dibrom indigo, its homolog or deriv., is mixed at -10° with 8 parts chlor sulfonic acid, 1 part Br or alk. bromide, and about 1 part P,O, or other substance having greater affin- ity for water than SO,. Products are sol. in conc. H,SO, (G), in C,H;NH,, C,H,NO,, CHCL, CCl,, acetone C,H, and alc., (B—G); violet to green BLUE vat (GY) dyes. 1,419,720—June 13, 1922. Lee E. H. Cong, Syracuse, New York. (Dow.) Method of making phenylglycine bodies. Improved process for making phenylglycin bodies. A salt of chlor acetic acid is dissolved in cold aq. soln. of anizin and gradually added to a hot aq. satd. soln. of anilin with undissolved anilin present in sufficient amount for the re- action. Excess anilin is distilled off, soln. cooled, the cryst. phenyl glycin filtered and washed with cold aq. anilin. 1,427,863—Sept. 5, 1922. Carl SrEpHEen, Germany. Process for the preparation of compounds of isatin-a-arylides with sulphur dioxide. Separation of isatin-a-arylids economically from sulfuric acid used in conden- sation. Reaction mixture containing the thio amid in 4 parts sulfuric acid is run into soln. of 5 parts ammonium sulfite in 20 parts water, keeping temp. low. The sulfite comp. of isatin a- anilid is pptd. nearly quantitatively, and SO, set free. Less ammonium sulfite may be used and filtrate neut. with gaseous NH, to recover (NH,),SO,. Excess SO, may be used in amounts corresponding to the arylid. Vigorous stirring is recommended or acid mixture can be sprayed into the basic sulfite soln. whereby strong decomp. results. 1,431,606—Oct. 10, 1922. Charles J. StRosAcKER and Howard J. Rupricut, Michigan. (Dow.) Method of making brominated indigoes. Mono to hexa-brom indigoes by improved process. Liquid bromine in quantity from 15-25 per cent in excess of theory to form desired prod- uct is added, at atmospheric temp. and pressure, all at once to finely divided dry indigo in ab- sence of any diluent, two ingredients ground together, gradually heated and kept s50-60° for 6-7 hours, then at 90° for 7-9 hours. Charge is neut. with NaOH then sod. bisulfite added, grinding being continued meanwhile. Suggested form of apparatus is described with drawing shown. 1,4384,983—Nov. 7, 1922. Wilhelm BaveEr and Alfred Herre, Germany. (Bayer.) Vat dyestuffs. 1.2-Naphth oxy thiophene 5.7-dichlor isatin, etc. Equimols 5.7-dichlor 1saTin and 1.2-naphth oxy THIOPHENE are dissolved in hot glac. acetic, mixed, and with conc. HCl are heated at 100° for 1 hour. Red brown crysts., sol. hot C,H,NO, (RBr), diff. sol. conc. H,SO, (RV) and in monohydrate (BV); Brown reducing vat (Y) dyes, fast to Cl, washing and light. 1,442,743—Jan. 16, 1923. Charles J. SrrosackER, Michigan. (Dow.) Process of making phenyl glycine. Three parts ANILIN and 1 part chlor acetic acid with 25 per cent aq. are slowly heated 226 DIGEST OF PATENTS until reaction starts then reaction allowed to reach completion without further heating. Reac- tion takes about 45 mins. Brive reducing vat dye. S. 874—“Indigo.”’ 1,444,277—Feb. 6, 1923. Maximilian P. Scumipt and Heinrich Rorss, Germany. (Kalle.) Manufacture of dyestuffs. (Product, not process, claimed.) Thio indigo derivatives. NAPHTHALENE 2.6-disulfo chloride in about 4 parts diluted alcohol (4:1) is reduced with 2 parts Zn dust to disulfinic acid, then by further reduction with HCl to insol. disulfid, again reduced by alk. hydrosulfite to NAPHTHALENE 2.6-dimercaptan, condensed in same soln. with equimol. chlor acetic acid and naphthalene 2.6-dithio cLycotic acid pptd. by HCl. The latter may be oxidized or dissolved in 10 parts chlor sulfonic acid or other reactive CO or CS comp. at O° with YBr color to form naphthalene 1.2.5.6-bis (oxy thiophene), which on standing is transformed into thio indigo. Other naphthalene dithio glycolic acids,’ brom and chlor de- rivs., etc., are claimed. GrrEn, dull vioLET to BRowNn reducing vat (VR-BrY) dyes. 1,461,435—July 10, 1923 Hermann SraupIncER, Germany; Hans Veracuts and Richard TosierR, Switzerland. (Basle.) Indigoidie dyestuffs and process of making same. 2-Thio NAPHTHISATIN, m.p. 153°, derived from oxatyt chloride and thio 2-NAPHTHOL, and equimol. oxy thio NAPHTHENE or other cylic comp. with reactive methylene group, such as ind- oxyl, thio indoxyl, pyrazolone, acenaphthenone, 1-oxy anthracene, 1-naphthol, or derivs., are added with cooling to about 6 parts H,SO,, then an equal amount glac. acetic further added. Dark powds., sol. in 98 per cent H,SO, (BrV-BG); fast RED to BRown reducing vat dyes. 1,466,687—Sept. 4, 1923. Wilhelm Bauer, Germany. (Bayer.) Indigoid wat dye. 5’7'-Dichlor isatin a-6-methoxy 1-naphthol. 5.7-Dichlor 1saTIN in dry benzene soln. is converted to alfa chlor deriv. by PCI, and con- densed with equimol. 6-methoxy 1I-NAPHTHOL, also in benzene soln. Dibrom isatin is also claimed and the black dye obtained by treating product with SO,Cl, at 70° in chlor benzene soln. Dark blue coppery powds.; gray-BLUE, oOlive-GREEN or green-GRAY to BLACK reducing vat (Y) dyes. 1,467,598—Sept. 11, 1923. Max Wyter, England. (British Dyes.) Manufacture of phenyl glycine compounds. Producing phenyl glycin with less anilin. One mol. trichlor ETHYLENE is gradually pump d into 1 mol. (plus 5 per cent) ANILIN and excess milk of lime, keeping temp. in pressure vessel at 170-180°. Excess anilin is always present as it first enters into combination to form ethylene triphenyl triamin then is hydrolyzed in same mixture to phenyl glycin, thus releasing anilin for further reaction. 1,473,887—Nov. 13, 1923. Charles J. StrosacKER and Howard J. Rupricut, Michigan. (Dow.) Method of making brominated indizgos. Dry INDIGO is brominated at 7o-80° under atmospheric pressure by allowing varying amounts of bromine to react directly with or without presence of an inert diluent such as CCl,. From 1-8 bromine atoms can be introduced by employing an excess of Br varying from 15 to 60 per cent and by varying the time of reaction up to 10-12 hours. Buiuer reducing vat dyes. Group VIII.—INDOPHENOL. 261,518—July 18, 1882. Horace Korcuiin and Otto N. Wirt, Germany., Manufacture of blue and violet coloring-matters. (Product also claimed.) Indo- phenols. Nitroso dimethyl anit1n HCl, reduced in aq. soln. at 50° with Zn to 4-amino dimethyl ANILIN and to this is added a mixture of pHENoL, NaOH and K.Cr,0,, then excess acetic acid. BLvE to vioLet direct or developed dyes that can be developed on fiber as dye or printing comp. Patent claims action of nitrosamins or phenols, chlorquinonimid, etc., upon a phenol in pres- ence of a reducing agent or of a para amino comp. in presence of oxidizing agent. Brug hydro- sulfite vat dyes. S. 619—‘‘Indophenol.”’ > es ee a a ae ! ; GROUP IX.—NITRO DYES 227 263,341—Aug. 29, 1882. Horace Korcuuin and Otto N. Witt, Germany. Manufacture of blue coloring-matters called ‘“Indophenols.’”’ (Product also claimed.) Indophenols by improved method, sol. in aq. Mixture of nitroso dimethyl aniuin, free base, of 1-naphthol and alcohol heated at 100°, NaOH added and alcohol distilled off. No reducing or oxidizing agent employed, simply heat, for condensation. Brug reducing vat dyes. S. 619—‘‘Indophenol’’-naphthol derivs. 275,774—Apr. 10, 1883. Horace KorcHiin and Otto N. Wirt, Germany. Treatment of indophenols. lLeuco indophenols. INDOPHENOL as fine paste is made strongly alkaline, heated gently, and grape sugar or other reducing agent added till liquid is yellow green. Leuco dye bath may be used at once or leuco dye pptd. by acid. Acid reducing agents also claimed. Dye must be oxidized on fiber and is suitable for printing. Note 261,518 and 263,341. 617,628—Jan. 10, 1899. Heinrich A. BErRntHSEN, Ger. and George F. JauseErt, France. (Badische.) Blue dye and process of making same. Oxy naphth InpopHENoL thio sulfo, derived by oxidation of equimols. of para diamin thio sulfo acid and 1-AMINO 2-NAPHTHOL 6-sulfo acid, is dissolved in 5-10 parts conc. H,SO, and heated at 1oo° till soln. is green and is pptd. on diln. Buus direct or acid mordant (Cr) dye, fast to light and washing. Note Ser. 662,179. (12/27/97). Group IX.—NITRO DYES. [bee note with Explosives, Group XXIV (e).] 225,108—Mar. 2, 1880. Heinrich Caro, Germany. (Badische.) Coloring-matter obtained from alpha-naphthol. 2.4’-Dinitro-1-naphthol 7-sulfo. I-NAPHTHOL, sulfonated, then nitrated. Methods for using conc. and fuming sulfuric given and tests for end of reaction and purification. The free sulfo acid is easily sol. in aq. and alc., insol. in hydrocarbons, CHCl,, CS,, ether and conc. mineral acids, soln. is yellow and strongly acid, its salts with alks., alk. earths, Al., and Zn are sol. in aq., the K., Ba and Pb salts only sparingly in hot aq.; it is a yELLow acid dye that will not rub off, suitable for print- ing and for mixtures with other acid dyes. S. 7—“‘Naphthol Yellow S.” 244,757—July 26, 1881. Emil LasyHarpt, Germany. (Hochst.) Coloring-matter from tetranitro-naphthol. Tetra nitro naphthol. Brom NAPHTHALENE, 3 parts, added to 12 parts fuming HNO,, dild., dinitro derivs. sep- arated, washed, then heated with 8 parts sulfuric (1.84) containing fuming HNO,, to obtain mixture of isomeric tetra nitro brom naphthalenes, from which the one claimed in patent is separated by greater soly. in acetic acid, benzene, etc., then digested in warm dil. soda soln. to form naphthol. Chlor deriv. of naphthalene may be used. A yELLow and orancE acid dye. - No S. number—‘‘Heliochrysin.” 256,379—Apr. 11, 1882. Carl Rumprr, Germany. Manufacture of dye-stuff or coloring-matter. A mono, di, or tri nitro 2-naphthol sulfo. 2-NAPHTHOL 1-sulfo nitrated, with 50 per cent HNO,, at 30-40°, and soln. neut. with K,CO, or other. Proportions of ingredients and temp. may vary. Product is yellow cryst. powd.; a YELLOw acid dye. 289,543—Dec. 4, 1883. Ivan L&vinstern, England. Manufacture of yellow coloring-matter. Nitro oxidized nitroso-1-naphthol sulfo. I-NAPHTHOL disulfonated with H,SO, (170° Tw) at 130°, treated with nitrous acid below 10°, then allowed to stand 3 days with dil. HNO, (1:1) or heated to boil (less satisfactory). Product forms yellow earthy lumps, easily pulverized, is odorless and has acid properties; it is a YELLOW acid dye. Probably S. 7—‘‘Naphthol Yellow S.” 228 DIGEST OF PATENTS 300,874—June 24, 1884. Fritz Krucer, Georg Tosras and Eduard Krcrr, Germany. (Beyer, Kegel.) Production of coloring-matter from dinitro-phenol. 2.6-Dinitro phenol sulfo. 2-Nitro PHENOL 4-sulfo acid or phenol 4-sulfo, nitrated, using H,SO, and saltpeter or mixed acids, then pptd. with potash, Ammonia salt is formed by evapn. to dryness with excess NH,OH. It is an orange-rEp acid dye. Near S. 5—‘‘Picric Acid.” 324,615—Aug. 18, 1885. Leo VicGnon, France. Manufacture of coloring-matter from alpha-naphthol and dinitro-naph- thol. Mixture of disulfo 1-naphthol and trinitro 1-naphthol. I-NAPHTHOL, I part, sulfonated in 6 parts 66° H,SO, near boil till liquid, cooled and dild. by ice and nitrated with 40° HNO, below 30°, heated to 40°, cooled to 12-15°, filt. redissolved and pptd. with potash. Product is a yELLOwW acid dye. Near S. 7—‘‘Naphthol Yellow S.” 333,036—Dec. 22, 1885. Heinrich Voitiprecut and Carl Mznscuinc, New York. (Schoellkopf.) Nitronaphtholsulphonie acid. Nitro 1-naphthol sulfo. NaPHTHALENE 1-sulfo, lime salt, mixed with 2 parts H,SO, (66°) and less than 0.5 part HNO, (40°), heated at 90-100°, two resulting nitro sulfo acids convertel into amino derivs., sepd. by unequal soly. in aq., less sol. deriv. diazotized, diazo body boiled in dil. H,SO, to form naphthol, disulfonated by heating to 80-90° with 2-3 parts H,SO, (66°) till sol. in aq., and Na salt formed. Resulting 1-NAPHTHOL disulfo acid is nitrated at 60-70° with 54 per cent HNO, and potash salt formed. It is a yvELLOw acid dye, of redder shade than Naphthol Yellow S. Note 333,034 to 9, inc., and 144, 652. 666,627—Jan. 22, 1901. Max NEUMANN, Germany. (Westfalisch.) Process of making picrie acid. sym-Trinitro phenol from anilin. ANILIN converted by fuming H,SO, to suLFANILIc acid, diazotized, sepd. and added to HNO,, so that final conc. is 40°,. gently warmed till N begins to evolve, then let stand 36 hours. Yield is 90 per cent. S. 5—‘‘Picric Acid.” 743,778—Nov. 10, 1903. Joseph Turner, England. Yellow dye and process of making same. Tetra to hexanitro diphenylamin. 2.2'-Dinitro DIPHENYLAMIN 4.4/-disulfo in 25 per cent HNO, heated to 80~-g90° till partly pptd. Dyestuff is a yellow powd., easily sol. hot aq., sol. conc. H,SO, (OY); a greenish YELLOW acid dye, fast to light, that levels and penetrates well. (1904) S. 6—‘‘Aurantia.” 763,756—June 28, 10904. Benno Homo.ixka and Josef Erser, Germany. (Ho6chst.) Process of reacting on nitramins with formaldehyde and a product there- of. 5.5’-Dinitro 2.2'-dinitroluidino-methane. : 5-Nitro 2-TOLUIDIN, m.p. 107°, or other primary aromatic nitramin, as salt, mixed with sufficient 40 per cent FORMALDEHYDE. Products are yellow to orange yellow powds., insol. aq., little sol. in org. solvents, sol. in hot glac. acetic acid; YELLOW lake dyes. S. 8—‘“‘Pigment Chlorine GG.” 932,266—Aug. 24, 1908. Ernst Fuss—ENEGGER, Germany. (Badische.) Yellow dye and process of making. 5.5’-Dichlor 2.2’-dinitro diahilino methane. 5-Chlor 2-NITRANILIN aS IO per cent paste, two mols., heated in closed vessel at 70-80° with 1 mol. FORMALDEHYDE, 30 per cent soln. Product is yellow powd. m.p. 210°, diff. sol. alc., easily sol. hot xylene; a greenish YELLOW lake dye, fast to lime, light, aq., and alc. Note 955,080. GROUP IX.—NITRO DYES 229 955,080—Apr. 12, 1910. Paul Jutius and Ernst Fuss—ENEcGER, Germany. (Badische.) Yellow dye and process of making same. 4.4/-Dichlor 2.2’-dinitro dianilino methane. 4-Chlor 2-NITRANILIN heated to 7o—80° in closed vessel with FORMALDEHYDE. Product is a yellow powd., m.p. 262°, fairly sol. hot xylene; an orange YELLOW lake dye, fast to light. Near S. 8—‘‘Pigment Chlorin.” Note 932,266. 1,059,571—Apr. 22, 1913. Robert ScuMipLin, Germany. (Héchst.) Yellow to brown wool-dyestuffs and process of making same. 2.4-Dinitro 4’- anilino 3’-sulfo diphenylamin and homologs. 4-Amino DIPHENYLAMIN 2-sulfo, Na salt, in aq. soln. mixed at 100° with 1-chlor 2.4-dinitro BENZENE, a little powd. chalk being present to neut. acid, and product converted to Na salt. Tolyl and other aryl derivs. are claimed. Products are dark colored cryst. powds., easily sol. hot aq., and are YELLOW to BROWN acid dyes, fast to light and alk. 1,162,109—Nov. 30, 109015. Robert ScHMIDLIN, Germany. (Hochst.) Brownish-yellow wool dyestufis and process of making same. _§ 4.4'/-Diamino 3-sulfo 2/-amino diphenylamin, in which one para amino group contains an aryl and the other a 2”.4”-dinitro residue, while the 2-position may or may not contain an aryl-oxy residue. 4-Phenoxy 2’.4’-diamino DIPHENYL METHANE 3-sulfo with 2 or 4 position substituted by aryl amino or aryl oxy residue, in dil. Na,CO, soln. stirred for several hours at 100° with 1 mol. 1-chlor 2.4-dinitro BENZENE. Products are brown to black powds., diff. sol. cold aq., easily sol. hot aq. and alc.; brownish YELLOW acid mordant (Cr) dyes, fast to washing, light and alk. 1,166,80S—Jan. 4, 1916. Louis BLancry, Germany. (Badische.) Pigment. Nitro amino benzophenone or nitro amino sulfo benzid and derivs., in which the nucleus consists of two phenyl groups united by a polyatomic group of less than four atoms and containing oxygen. 3.3/-Dinitro 4.4’-diamino sulfo BENZID, or 3.3/-dinitro 4.4’-diamino BENZOPHENONE, or other, mixed in dry or paste form with Al (OH),, dried and ground. Other components and lake bases claimed. Resultant lakes are YELLOW with good covering power, fast to aq., oil, lime, alc., and light, and suited for printing, lithographic inks, and fine pigments. 1,299,171—Apr. 1, 1919. Arthur G. Green, England. Manufacture of picric acid. 2.4.6-Trinitro phenol by improved process. Dinitro PHENOL, (produced by chlorinating BENZENE, nitrating the chlor BENZENE with mixed acid, and converting the dinitro chlor BENZENE into dinitro phenol by boiling with caustic alk.), nitrated at 100° in mixed acid containing 1 mol. HNO,. Yield is nearly theoretical. Patent gives detailed advantages of new method. S. 5—‘Picric acid.” 1,349,802—Aug. 17, 1920. lL. G. BapirEr and lL. B. Horiipay, England. (Holliday.) Process of manufacture of picric acid. 2.4.6-Trinitro phenol, from a commercial product. Dinitro PHENOL mixed with 2.5 parts or 98 per cent H,SO, then about 1 part mixed acid (98 per cent H,SO, and 42° HNO, 1:1) with HNO, from 3-7 per cent in excess of theory is added, keeping temp. at 20-30° for 12 hours. Temp. and conditions may vary. No nitrous fumes are evolved and temp. is a normal one. S. 5—‘‘Picric Acid.” 1,380,186—May 31, 1921. Theodore J. Brewster, New Jersey. Process of making nitrophenolic compounds. 2.4.6-Trinitro phenol by more eco- nomical method, with less loss and increased yield. BENZENE, PHENOL, or other appropriate ring comp. is mono nitrated with a limited .quantity of HNO,, keeping temp. below 60° by artificial cooling; or a phenol is first sulfonated then nitrated at low temp., and then tri-nitrated with HNO, at 100°. Sy s—‘Picric Acid.” Note 1,380,185. 230 DIGEST OF PATENTS 1,393,714—Oct. 11, 1921. C. M. A. Stine and J. L. Gitson, Delaware. (du Pont.) Process of producing picric acid. 2.4.6-Trinitro phenol in reduced operating time, and more economically. Dinitro PHENOL suspended in H,SO, (1.5 parts of 92-98 per cent) at room temp., heated to 71° and mixed acid (80 per cent HNO,) gradually added during 2 hours with temp. 71-94° until 15 times the theoretical quantity HNO, is present, then temp. raised to 94-113° for one hour, cooled to 25-52°, and spent acid containing 75 per cent H,SO,, 2 parts, further added. 1,396,001—Nov. 1, 1921. David B. Macponatp, England. Manufacture of picric acid. 2.4.6-Trinitro phenol, pure, of high m. p., and free from metallic contamination, with reduced danger to workmen. BENZENE is nitrated by usual methods with HNO, and Hg as catalyst or with action of alk. nitrate on a sulfonated PHENOL, at a low temp. of 35°, thus restraining the nitration and oxida- tion, excess NITROBENZENE is driven off by steam, residue recryst. from benzene, and benzene recovered. Apparatus is described in detail. S. 5—‘‘Picric Acid.”’ 1,412,707—Apr. 11, 1922. W. B. RicHarpson, North Carolina. Brown dye and process of making same. Possibly a mixture containing some mono nitro 1.5-dioxy naphthalene. 1.5-Dioxy NAPHTHALENE slowly added to 10 parts HNO, (1.3), stirred 1 hour, then 15 parts HNO, (1.42) further added, stirred, let stand half hour and poured into water to ppt., all being carried out at room temp. A brown powd., slightly sol. aq., dil. HNO, and H,SO,, sol. in NH, and Na,CO, solns., decomp. by HNO,, 1.42, containing 3.75-5.5 per chat N; a BROWN direct axe for silk and wool and grey brown on tannin mordanted cotton. 1,413,914—Apr. 25, 1922. lL. B. Horttipay and J,. G. Baprer, England. (Holliday.) Process of manufacture of picric acid from dinitrophenol in crystal form and the elimination therefrom of the sulphate of lead. 2.4.6-Trinitrophenol pure and free from lead. Dinitro PHENOL is dissolved in 25 parts conc. H,SO,, to which HNO,-H,SO,, (about 1:1 with 3.7 per cent HNO, in excess of theory), is added, keeping at 20-30°, then the mass is heated to 85°, steam blown in to raise the temp. above the m. p. of picric acid, stirred, cooled, and filtered at 25-30° to separate the picric acid from the bulk of PbSO, in soln., and crysts. washed with dil. H,SO, of sufficient strength to dissolve PbSO, at 25°. SS. .s—“Picric Acid.” Group X.—NITROSO. 316,036—Apr. 21, 1885. Otto HorrMann, Germany. (Cassella.) Coloring-matter derived from naphthol. (Process claimed.) Ferro bis=(nitroso 1- naphthol 4-sulfo). Nitroso 1-NAPHTHOL 4-sulfo, or any nitroso naphthol sulfo except 2.1 and disulfo 2.6.8, oxidized with FeCl. or other iron salt. Or naphtholsulfonic acids may be treated with nitrous acid and iron or its salts. Dye is a green powder, easily sol. in cold aq. (YG), insol. in alc., benzene, or glac. acetic., unaltered by alks., destroyed by strong mineral acids, iron component pptd. by (NH,),S; a GREEN acid dye that may be mixed with indigo carmine. S. 4—‘‘Naphthol Green B.” 862,835—May 10, 1887. Thomas Hoiuipay, England. Process of dyeing. (Product claimed.) Metallo bis=(nitroso 1-naphthol sulfo.) Wool fiber mordanted with bichromate immersed in bath containing nitroso 1-NAPHTHOL (or beta comp.). Other chrome, iron, copper or lead salts and nitroso naphthols are claimed, and re- verse process—wool first in nitroso bath, then mordant bath. Near S. 4—‘‘Naphthol Green B.” Note 355,933, 34 and 35. 386,247—July 17, 1888. Thos. Hotiipay, England. (Holliday.) Process of dyeing. (Product also claimed.) Metallo-bis-nitroso-1-naphthol-sulfo. Process of mfr. is practically the same as in 362,835, the color being applied in the latter to wool fiber and in the present patent to cotton or other vegetable fiber. Near S. 4—‘‘Naphthol Green B.” 413,724—Oct. 29, 1889. Henry D. Kenpatut, Massachusetts. Brown dye _ (Process claimed.) Dinitroso RESORCIN, 3 mols., or other, treated with sodium hydrosulfite (from Zn and Sr ee ee ee a ee ee ee GROUP XI.—OXAZIN 231 NaHSO,). A Brown acid mordant dye, fast to soap, light, air and acids, and may be mixed with anthracene colors. 420,311—Jan. 28, 1890. Alcide F. Porrrier, France, Nitroso dye. An azin dye, see Group V. Group XI.—OXAZIN. 252,273—Jan. 10, 1882. James H. Srespins, Jr., New York. Purple dye-stuff or coloring-matter. Dimethyl 3-amino phen naphth oxazin. Nitroso dimethyl anit1n HCl with Na salt of 2-NAPHTHOL sulfo to 119° then 121°. VIOLET acid mordant dye. (Fe or AI.) S. 649—‘“‘New Blue R” sulfo. Note 255,349 for similar dye developed on fiber. 252,274—Jan. 10, 1882. James H. Sressins, Jr., New York. Manufacture of blue coloring-matter. (Product, not process, claimed.) Dimethyl 3- amino phen naphth oxazin sulfo. Nitroso dimethyl anrLt1n HCl reduced in aq. by Zn dust to 4-amino dimethyl anriLin, and filtrate with 1-NAPHTHOL sulfo condensed and oxidized in alk. bichromate soln., then pptd. by acetic acid. BLur to GREEN acid mordant (Cr) dyes. Note 255,350. 253,4435—Feb. 7, 1882. James H. Srepsins, New York. Coloring-matter or dye-stuff. Dimethyl 3-amino 5-methyl phen oxazin. Nitroso dimethyl ANILIN reduced with Zn dust in acid soln. to dimethyl 4-rHENYLENE DIAMIN which with 2-cRESOL, is oxidized in alk. soln. with Ca(OC1),. BLvuE acid mordant (Cr, Al) dye. Note 253,444 oxidized with bichromate. 253,445 employs phenol (for cresol) and CaQOCl,; 254,064 employs 1-naphthol sulfo and bichromate; 254,065 employs 1-naphthol. 253,444—Feb. 7, 1882. : James H. Sreszins, Jr., New York. Coloring-matter or dye-stuff. Dimethyl 3-amino 5-methyl phen oxazin. Patent is similar to 253,443 but oxidized with bichromate instead of Ca (OC1),. BuvE acid mordant dye. (Cr- AI.) Addition to 253,443. 253,445—Feb. 7, 1882. James H. Sressins, Jr., New York. Coloring-matter or dyestuff. Dimethyl 3-amino phen oxazin. Patent similar to 255,443 but employs phenol for cresol and oxidizes with Ca (OC1),. BLuE acid mordant (Cr.Al) dye. Addition to 253,443. 253,721—Feb. 14, 1882. Horace Korcuiin, Germany. Manufacture of colors or dye-stuffs. Dimethyl gallocyanin. Nitroso dimethyl ANILIN or other tertiary amin heated in aq., in alc. or acetate soln. with GALLIC acid or other principle analogous to tannin. VuonEtT acid mordant (Cr) dye. S. 626—“Gallocyanin D H.”’ Note 257,498 for leuco dye formed by reduction with Zn in neut. or alk. soln. and 962,712 (Lommel) by reduction with Zn and HCl or electrolytically. 254,0G4—Feb. 21, 1882. James H. Sressins,Jr., New York. Dye-stuff or coloring-matter. Diethyl 3-amino phen naphth oxazin sulfo. Similar to 253,443 but employs 1-NaPHTHOL sulfo instead of cresol, with bichromate as oxidizing agent. Biur direct or acid mordant (AI,Cr) dye. 254,065—Feb. 21, 1882. James H. Stessins, Jr., New York. Dye-stuff or coloring-matter. Diethyl 3-amino naphthoxazin. Similar to 253,443 but employs 1-NAPHTHOL, and bichromate. Buuk acid mordant (Cr, Al, etc.) dye. 255,350—Mar. 21, 1882. James H. Srespins, Jr., New York, Manufacture of blue coloring-matter. Diethyl 3-amino phen oxazin. Nitroso diethyl anriL1n HCl reduced in aq. at 60° with Zn dust to form diethyl 4-PHENYLENE DIAMIN, filtrate condensed and oxidized with PHENOL, in alk. bichromate soln., then*pptd. by acetic. Brive acid mordant or direct dye, fast to alk. Addition to 252,274. 232 DIGEST OF PATENTS 348,816—Sept. 7, 1886. Haydn M. Baker, New York. Resorcin-blue compound. (Process also claimed.) Two amidogen groups combined with three resorcin rests C,,H,,N,O,. Resorcin dissolved in dil. NH,, with equal weight of cuprammonium carbonate and copper plate dipped or rotated in soln. keeping alk. with NH,. The ammonia suboxide of copper formed dissolves in excess NH, and acts like battery. Soln. is neut. with HCl, filt. etc. or treated with sheet of Zn metal to ppt. Cu, then dye pptd. by acid. Buiur acid mordant dye giving dyeings like indigo, suitable for lakes. 364,320—June 7, 1887. Eduard Uuuricu, Germany. (Hochst.) Nitrosophenyl-blue dye-stuff. Nitroso phenyl blue, or tolyl gallocyanin, etc. 4-Nitroso phenyl ToLtyL amin from nitrosoamin by treating with alc. HCl, condensed in glac. acetic with GALLIC acid or other phenol or oxy carbo acid at 100°. Green-BLUE acid mordant (Cr, Fe) dye, suitable for printing. Note 366,356. 366,356—July 12, 1887. Eduard Uuiricu, Germany. (Hochst.) Blue coloring-matter formed by the action of paranitroso-diphenylamines on phenols or oxycarbonie acids. Phenyl gallocyanin. 4-Nitroso DIPHENYLAMIN prepared from diphenyl niTtrosamin and alc. HCl, condensed in 20 per cent acetic soln. with GaLLic acid by heating at 100°. Buus acid mordant (Cr, Fe) dye, suitable for printing. Addition to 364,320. 366,357—July 12, 1887. Eduard Uuiricu, Germany. (Hochst.) Blue ecoloring-matter formed from paranitroso-methyldiphenylamine on phenols or oxycarboniec acids. Phenylated gallocyanin. 4-Nitroso methyl DIPHENYLAMIN in glac. acetic or alc. soln., heated at 100° with GaLuic acid. BuveE acid mordant (Cr, Fe) dye, suitable for printing. Near S. 626—‘‘Gallocyanin DH.” 396,574—Jan. 22, 1880. Alfred Kern, Switzerland. Formation of purple coloring-matter. (Product, not process, claimed.) Alkyl ester of dimethyl gallocyanin. Nitroso dimethyl ANILIN and methyl Gauuic acid, 1 mol. each, condensed by boiling in methyl alcohol. Blue vioLtet acid mordant dye, suitable for printing. S. 636—‘‘Prune.” 404,309—May 28, 1889. Jakob Scumip, Switzerland. (Basle.) Blue azo dye. Dimethyl 3-amino phen-naphth oxazin. I-NAPHTHYLAMIN coupled with diethyl 3-amino PHENOL, or other, in glac. acetic soln., reduced with HCl and Zn dust, and resulting amino compounds oxidized with bichrom. BLveE basic mor- dant dye. Probably S. 655—‘‘Nile Blue A.”’ Note 402,980 and 431,541. Patentee calls this an azo dye. 410,733—Sept. 10, 1880. Rodolph Gerrcy, Switzerland. (Geigy.) Process of making a violet dye. Dimethyl 3-amino phen-naphth oxazin. Amid of dimethyl ANILIN nitroso DIMETHYLANILIN condensed with GALLAMID by heating in acetic acid soln. VuioLer acid mordant (Cr) dye, suitable for printing as bisulfite comp. S. 637—‘‘Gallamin Blue.” 413,562—Oct. 22, 1880. Alfred Sarauw, Switzerland. (Durand.) Production of coloring-matter. Apparently a double oxazin similar to S. 649. Nitroso dimethyl ANILIN, 2 mols., or other tertiary aromatic amin, gently heated in alc. soln. with 2.7-dioxy NAPHTHALENE (m.p. 186°) until nitroso comp. disappears. Buiuer direct or acid mordant, dye. Near S. 649—‘‘New Blue,” ‘Meldola’s Blue,” or 635, ““Muscarin.” Patent claims azo dye. See also 252,273. GROUP XI.—OXAZIN 233 420,164—Jan 28, 1890. Johannes Mouter, Switzerland (Basle.) Blue dye. Anilid of dimethyl gallocyanin, or other. Nitroso dimethyl anILIN or other, condensed with anilid or other amid of GaLuic acid or other tannin by boiling in dil. acetic acid or in alc. Buur to blue viotet acid mordant (Cr or Al) or acid dye, suitable for printing, used as a bisulfite comp. to render soluble in aq. S. 639—‘“‘Gallanil Violet” or B S (bisulfite comp.). 440,359—Nov. 11, 1890. Carl A. Mayer, Switzerland. (Durand.) Blue dye. (Process also claimed.) Naphthylamid of dimethyl gallocyanin. Nitroso dimethyl ANILIN condensed with GALLO NAPHTHYLAMID derivs. from tannin GALLIC acid, or other and 1- or 2-NAPHTHYLAMIN or other. Violet RED to blue vioLEtT acid mordant and acid dyes, reduced with alk. bisulfite for dyeing purposes. S. 639—‘‘Gallanil Violet.”” Note 253,721 for original gallocyanin patent. 440,536—WNov. 11, 1890. Rene Bown, Germany. (Badische.) Blue dye. Dimethyl-3-amino-6-oxy phen oxazin carbo-8-carbo acid. 3.5-Dioxy BENzoIc acid made by melting 3.5-disulfo BENzoIc in KOH, is heated in much water to 70° and 2 mol. nitroso dimethyl anin1n HCl slowly added. Buus direct or acid mordant (Cr) dyes that dye well in mixtures with such colors as alizarin. 431,541—July 1, 1890. ' Theodor Reissic, Germany. (Badische.) Blue dye. as-Diethyl-3.6-diamino phen. naphth-oxazin. I-NAPHTHYLAMIN HCl condensed in glac. acetic soln. with nitroso diethyl 3-amino PHENOL. BuvE basic mordant dye. S. 658—‘‘Nile Blue A.”’ Apparently same dye as 404,509 (Schmid). 442,680—Dec. 16, 1890. Meinhard Horrmann and Arthur WeinBrrc, Germany. (Cassella.) Blue dye. Tetramethyl 3.6-diamino naphth phenoxazin. Dimethyl 3-amino naphth PHENOxAzIN HCl (‘‘Meldola’s New Blue R’’) powd., mixed with aq. 40 per cent soln. of DIMETHYL amin, product oxidized by air at 15°, and pptd. as HCl salt. Bichromate, FeCl, or peroxide in acid soln. may be used for oxidation. Green BLUE basic mor- dant dye. S. 651—‘‘New Methylene Blue GG.” Inventor claims addition of basic N(CH,), group and loss of H, probably with formation of new chromophore. 444,538—Jan. 13, 1891. Johannes Monier and Carl A. Mayer, Switzerland. (Durand.) Blue dye. (Process also claimed.) Sulfo derivs. of alphyl gallocyanin anilid. Dye obtained in 420,164, from nitroso dimethyl ANILIN, ANILIN, and TANNIN, heated with 10 parts ANILIN on oil bath at 158°, and product heatéd in 4 parts conc. H,SO, at 100° or fuming acid, (20 per cent SO,) at 15-18°. Buiue acid and acid mordant (Fe, Cr) dyes. Near S. 646—‘‘Corein AR.” Note 420,164 and 440,359. 451,502—May 5, 1801. Johannes Mouter and Carl A. Mayer, Switzerland. (Durand.) Blue dye. Gallocyanin anilid. Nitroso dimethyl aniz1n HCl acted upon by condensation product of TANNIN with ANILIN and product heated in 4 parts 90-95° H,SO, containing no anhyd., at 80°,— see test for end of re- action. Buus acid dye. S. 639—‘‘Gallanil Violet R.” Note 420,164, 444,533 and 440,359. 454,535—June 23, 1891. Albert CorBENzL, Germany, (Hochst.) Gray dye. Diethyl amino naphth phenoxazin sulfo. Nitroso diethyl ANILIN, 1 mol., and 1 mol. 2-NAPHTHOL 6-sulfo “Schaeffer” heated at 100° in glac. acetic or alcohol, or in aq. with ZnCl, at 70-80°. Blue-cray basic mordant dye, fast to light and suitable for printing. Sulfonated S. 649—‘“‘New Blue R.”’ 494,838—Apr. 4, 1893. Fritz Benprer, Germany. (Leonhardt.) Blue dye. Tetra methyl diamino methyl phen-oxazin. Dimethyl 3-amino creEsor, condensed with nitroso dimethyl ANILIN or other. Buiugx basic mor- dant dye. S. 620—“Capri Blue GON.” 234 DIGEST OF PATENTS 497,114—May 9, 1883. Jacob Brack; Switzerland. (Durand.) Blue dye. (Process also claimed.) Alkyl amino derivs. of gallocyanins. GALLOCYANIN from GALLIC acid or other and nitroso dimethyl aniLIN, heated with mMETHYL- AMIN or other fatty amin. VIOLET to green-BLUE acid mordant (Cr) dye, suitable for printing. 499,243—June 13, 18093. Emil Meyer, Germany. (Bayer.) Blue dye. (Process also claimed.) Dimethyl amino phen-naphth oxazin with tetra methyl diamino diphenylmethane substituted for alfa hydrogen (4) in naphthalene component. NEw BLUE R, from nitroso dimethyl ANILIN and 2-NAPHTHOL, condensed with tetra methy\ diamino BENZHYDROL. BLuE basic mordant dye, by heating in alc. soln. suitable for printing. S. 652—‘‘New Fast Blue F,”’ etc. 518,458—Apr. 17, 1894. Karl KrexKELER and Paul Krais, Germany. (Bayer.) Blue dye. (Process also claimed.) Amid of diethyl gallocyanin. Nitroso diethyl an1L1n boiled in alc. or acetic soln. with GALLAMIc acid. Brive to blue-vioLEer acid mordant (Cr) dye. S. 641—‘‘Corein RR powd.” Similar to Bierer’s patent, see second part of method S. 641. §24,235—Aug. 7, 1894. Oscar Batty, Germany. (Badische.) Blue dye. (Process also claimed.) Gallocyanin. (?). Ga.Lic acid and dimethyl an1L1Nn or other, 2 mols., in dry condition, mixed with POCI,, then ZnCl, added. BuiveE acid mordant (Cr) dye, fast to light. 531,148—Dec. 18, 1894. Joseph BiererR and Charles De La Harpr, Switzerland. (Durand.) Blue dye. (Process also claimed.) A naphthol deriv. of gallocyanin similar to the resorcin deriv. S. 642. ‘‘Phenocyanin.” GALLOCYANIN from nitroso dimethyl] ANILIN and GaLLic acid, or other, combined in acid soln. with 2-NAPHTHOL 6-sulfo, oxidized in alk. soln. by air, then reduced in carbonate soln. by bisulfite. Buus and blue-vioLetT acid mordant (Cr) and acid dyes. S. 645—‘‘Gallazin A’ etc. See discussion of formula of this product in 992,613, which combines in alk. soln. 534,809—Jan. 26, 18905. Joseph Birerer, Switzerland. (Durand.) Blue dye. (Process also claimed.) Mono-, di- or tri-sulfo deriv. of the anilid of diethyl amino | gallocyanin. Diethyl amino azo BENZENE sulfo or other di-alkyl amino azo benzene sulfonated in the second benzene nucleus, condensed with GALLAMIc acid or other in glac. acetic soln. BLUE, VIOLET to GREEN acid and acid mordant (Cr) dyes, fast to light and fulling. S. 628—‘“Gallocyanin MS.” §S. 641—‘“‘Corein RR.” Incorrectly described in Schulz 646 as “faction of anilin on Coreine (641) and sulfonation.”’ 547,173—Oct. 1, 1895. Carl A. Moyer and Charles p—E LA Harpe, Switzerland. (Durand.) Leuco compound and process of making it. Leuco form of resorcin dimethyl gallocyanin. Nitroso dimethyl anILIN, or other, condensed with Gatiic acid or other to form GALLOCYANIN or amid thereof, which is heated in strong acid soln. with rREsorcIN. Lvs to blue-vioLEr acid or acid mordant (Cr) dyes, suitable for printing. S. 642—‘Phenocyanin V S.” Note 585,934 uses gallamic acid, ‘sulfonates and oxidizes in alk. soln. with air, while 616,622 oxidizes in alk. soln, excluding air. 548,158—Oct. 15, 1895. Emil Exsarsser, Germany. (Dahl.) Green dye and process of making it. 3.4-Dioxy 4’-sulfo 1.2-dinaphth oxazin (Schulz). 2-AMINO I-NAPHTHOL 4-Sulfo (or 1.2.4) 1 mol., condensed with 1 mol. 1.2-NAPHTHOQUINONE 4-sulfo by heating in alk. soln., then another half mol. of naphthoquinone added to boiling soln. Better yield obtained by excess quinone. GREEN acid mordant dye. S. 656—‘‘Alizarin Green G.” 548,344—Oct. 22, 18905. Arthur AsHwortu and Joshua Burcer, England. Brown dye. (Process also claimed.) 3.4-Dioxy naphth phenoxazin 1-carbo acid. I-AMINO 2-NAPHTHOL added to a sulfuric acid soln. of GaLiic acid, or tannin, then heated gradually to 85-90°. Brown acid mordant (Cr) dye, fast to light and soap. Note 548,345 and 46 and 548,416 (Azo) for related dyes. GROUP XI.—OXAZIN 235 548,345—Oct. 22, 1895. Arthur AsHwortH and Joshua BurceEr, England. Brown dye. (Process also claimed.) 3.4-Dioxy naphth phenoxazin 1-carbo acid. Nitroso 2-NAPHTHOL or (2.1) added gradually to a soln. of tannin or GaLLic acid in cone. H,SO,, keeping below 25° at first, then raising temp. slowly to 90°. Addition of bisulfites to. color paste improves it. Brown to almost BLAcK acid mordant (Cr) dye, fast to light and soap. — 585,934—July 6, 1897. Charles p—E LA Harpe, Switzerland. (Durand.) Bloue dye. (Process also claimed.) Amid of resorcin diethyl gallocyanin sulfo acid. Nitroso diethyl ANILIN or other condensed with GALLAMIc acid or any gallic acid deriv. to GALLOCYANIN, and this condensed with rEsorciNn, then sulfonated before or after oxidation in alk. soln. with air. Brug acid and acid mordant (Cr) dyes, suitable for printing. S. 643—‘‘Phenocyanin T V.” Note 547,173 and 616,622 for modifications. Schulz 643 re- ports dye process as “Heating of phenocyanin (642) with sulfites.” 613,578—Nov. 1, 1898. Charles p—E LA Harpe and Charles VaucueEr, Switzerland. (Durand.) Blue dye from gallocyanin and process of making same. Leuco sulfo gallocya- nin, Nitroso diethyl an1LIN or diethyl amino azo benzene condensed to a GALLOCYANIN then treated with bisulfite in neutral or acid soln. Buur acid mordant (Cr) dye. S. 631—‘‘Chromocyanin V paste.’’ Note 518,458 for gallocyanin mfr. and 638,576 for closely similar specifications. 616,622—Dec. 27, 1808. Charles p—E LA Harper, Switzerland. (Durand.) Blue dye from gallocyanin and process of making same. Nitroso diethyl ANILIN or other combined with GALLAMIc acid to form a GALLOCYANIN, then with RESORCIN as in 547,173, and boiled in alk. soln. with exclus‘on of air. Violet BLUE acid mordant (Cr) dye, suitable for printing. -S. 644—“Ultracyanin B and R.” Apparently same as Steiner’s pat. S. 644 but ten years earlier. Note also 585,934 in which dye is heated_in alk. soln. with air, while above method excludes air. 638,576—Dec. 5, 1890. Charles p—E LA Harpe and Charles VAucHER, Switzerland. (Durand.) Oxazin dye. Leuco sulfo gallocyanin. Same as 613,578 except slightly different proportions of ingredients used. Comparison with 410,733 Made and different color reactions of product from those of 613,578 reported. No process claim. Near S. 631—‘‘Chromocyanin V.” 643,338—Feb. 13, 1900. Arnold SYt5INER, Switzerland. (Sandoz.) Blue dye from gallocyanin. Alphyl sulfone radical substituted for H in OH of gallocya- nin dye. GaLLOcYANIN HCl stirred into soda-soln., heated to 70° and BENZENE sulfo chloride slowly added. Buve acid, acid mordant (Cr), and developed (CrO,) dyes, fast to light and milling when chromed, 654,087—July 17, 1900. Bruno Bryer and Friedrick SCHAARROSENBERG, England. (Badische.) Blue-green oxazin dye. Possible tetra methyl triamino oxy phenoxazin. Nitroso diethyl 3-amino PHENOL HCl or other heated at 100° in aq. soln. with SnCl,, pptd. with HCl and Na salt formed as usual. Blue-creEN acid mordant dye, suitable for lakes, fast to milling and light. 662,224—Nov. 20, 1900. Charles p—E LA Harpr, Charles VAucHER and Herman Loretan, Sw’'tzerland. (Durand.) Gallocyanin sulfite dye and process of making same. Probably a bisulfite comp. | of a sulfo gallocyanin anilid that may be further sulfonated. Nitroso dimethyl an1L1In condensed with CALLANILID to form GALLOCYANIN, sulfonated, then heated with bisulfite. Buus acid mordant (Cr) dye, suitable for printing. S. 633—‘“Indalizarin R.” Note 613,578 and 638,576 which also apply bisulfite to a sulfonated gallocyanin. 16 236 DIGEST OF PATENTS 663,221—Dec. 4, 1900. Charles pE LA Harpe, Switzerland. (Durand.) Leucogallocyanin-sulfonic acid and process of making same. Leuco gallocya- nin sulfo acids, dyeing chromed cotton blue, discharging white. Leuco dye from GALLAMIC acid and nitroso dimethyl AaNnILIN, or other, (‘‘Corein 2 R,” “Gallamin Blue,’ ‘‘Prune,” etc.) slowly added at ordinary temp. to sulfuric acid (100 per cent) and let stand. Chlor sulfonic acid also can be used to advantage. Note 534,809, 629,666 and 663,220. 707,832—Aug. 26, 1902. Charles pE ta Harps, Switzerland. (Durand.) Blue dye and process of making same. A sulfonated alkyl benzyl gallocyanin. Nitroso alkyl benzyl aniLin sulfo condensed with Gatiic acid or derivatives. BuLusg acid mor- dant (Cr) dye. S. 625—‘‘Chromheliotrop. sulf.” 707,833—Auzg. 26, 1902. Charles p— LA Harpe, Switzerland. (Durand.) Blue dye and process of making same. _ Resorcin deriv. of sulfo ethyl benzyl gallo- cyanin amid. Nitroso ethyl benzyl aniLin sulfo condensed with GALLAMIc acid to form GALLOCYANIN then condensed with RESORCIN in acid soln. Brug acid mordant (Cr) dye. Near S. 642—‘‘Phenocyanin V S” sulf. 807,181—Dec. 12, 1905. Charles Oswatp, Herman Loretan and Charles p— La Harper, Switzerland. (Durand.) Yellow-green dye and process of making same. Formaldehyde deriv. of dimethyl gallocyanin amid. GALLOCYANIN dye, from nitroso dimethyl ANILIN and GaLLAmic acid, or other, and FORMALDE- HYDE, heated in dil. HCl at 100°, or in conc. H,SO, at room temp., then pptd. by alkali. Sub- sequent heating in aq., dil. acid or aq. CaCl, etc. at 100° or higher, gives a blue dye. Yellow- GREEN and BLUE acid mordant (Cr) dyes. 842,303—Jan. 29, 1907. Charles p—E LA Harpe and Rudolf BurckuHarpt, Switzerland. (Durand.) Leuco products from gallic compounds and alkyl-diamino-arylIthiosulfonic acids, &c. (Process also claimed.) Thio sulfonated amid of dimethyl gallocyanin. Dimethyl 4-PHENYLENE DIAMIN thio sulfo or diethyl compound condensed with GaLLamic acid, gallic acid, methyl gallate or gallanilid. Blue-vioLer acid mordant (Cr), fast to light and washing. Near S. 637—‘‘Gallamin Blue” or 641 ‘‘Corein.” 844,156—Feb. 12, 1907. Herman Loreran, Switzerland. (Durand.) Greenish-blue dye and process of making same. Dimethyl gallocyanin amid, in which H and OH are substituted by diamins. Nitroso dimethyl ANILIN, or other, and GALLAMID, methyl gallate, etc., condensed to GALLo- CYANIN, then heated at 70° with dimethyl or diethyl 4-PHENYLENE DIAMIN, or 3-phenylene diamin or other aromatic diamin with one free amino group, and with dinitro benzene or other nitro body. Green-BLUE acid mordant (Cr) dye. S. 627—‘*Modern Cyanin.” 856,536—June 11, 1907. William LomMMmEL, Germany. (Bayer.) Leueco derivative from gallocyanin. Leuco gallocyanins by alkaline reduction and condensation to pyrogallol. Dye of 856,537 heated for long time with alkaline reducing agents until after oxidation it is insol. in dil. Na,CO, and sol. in HCl with blue color. Pyrogallol condensation as in 856,537, and reduction to leuco form take place in one operation. VuioLEer acid mordant (Cr) dye, suitable for printing, more sol. than original gallocyanin. (No claim for dye.) 856,537—June 11, 1907. Wilhelm Lommet, Germany. (Bayer.) Gallocyanin dye. Pyrogallol deriv. of gallocyanin. GALLOCYANIN from nitroso dimethyl ANILIN and GaLiic acid heated with ag. sod. acetate until sol. in HCl and insol. in alk. carb. soln. VuioLet acid mordant dye, suitable for printing, of redder and purer shade than original gallocyanin. No claims as dye. GROUP XI.—OXAZIN 237 Note 856,536 and 884,745 for leuco form and also 863,907 and 629,666 for similar processes using sodium acetate. 863,907—Aug. ‘20, 1907. Charles pe 1A Harpz, Switzerland. (Durand.) Process of making leuco gallocyanin. Leuco gallocyanin corresponding in pyrogallol. Nitroso dimethyl ANILIN and GALLIC acid condensed to GALLOCYANIN, heated in vat or auto- clave in water to 100°, with or without an alkali, and alkali acetate or sulfate. VuioLEt acid mordant (Cr) dye, suitable for printing. S. 624—‘‘Modern Violet N.” Patent is process classed as dye. Note 629,666 and 884,745 for leuco gallocyanin and 856,536-7 for similar process using sodium acetate. 884,745—Apr. 14, 1908. Wilhelm LommeEt, Germany. (Bayer.) Leuco derivative of the gallocyanin series. Pyrogallol derivs. of amino gallocya- nins. Celestine Blue S. 641 or Gallamin Blue S. 637, heated in vat or autoclave with a) glycerin to 150°; b) water to 125°; or with c) alcohol to 140°. Note 410,733, 534,809 and 863,907, etc. 893,855—July 21, 1908. Wilhelm LomMeEL, Germany. (Bayer.) Leuco derivative of the gallocyanin series. (Process also claimed.) Leuco derivs. of substituted gallocyanins. “Celestin Blue,” derived from nitroso dimethyl ANILIN and GALLAMINIC acid, 2 parts, added to heated mixture of 1 part phenyl GLycin and 2 parts glycerin, at 115°, then dissolved in dil. HCl. Or without glycerin, mixture can be boiled in dil. HCl. Other components claimed. Buius to VIOLET acid mordant dyes. Near S. 637—‘‘Gallamin Blue paste.” 895,635—Aug. 11, 1908. Carl Hemwenreicu and Eduard Martz, Germany. (Bayer.) Gallocyanin dye. Amid of chlor diethyl gallocyanin. 4-Nitroso 3-chlor diethyl anrL1n condensed with GALLAMiIc acid. Green-B1uE acid mordant dye. Chlor deriv. of S. 641—-“Corein R R.” Note 534,809 for S. 641. 897,619—Sept. 1, 1908. Charles p—E LA Harpe, Switzerland. (Durand.) Process of condensing gallocyanins with amins. Anilid of dimethyl gallocyanin. Improved process for condensing amins with gallocyanins. (General claims.) Nitroso dimethyl anin1in or homolog, condensed with Gatuic or gallamic acid to form GALLOCYANIN then with ANILIN or other amin in presence of nitrobenzene or other, to prevent reduction and secure full yield of anilid deriv. Buiug acid mordant dyes. Near S. 522—‘‘Delphin Blue.” 898,0389—Sept. 8, 1908. Charles pz 1A Harpr, Rudolf BurcKHarpt and Ernst ZEHNTNER, Switzerland. (Durand.) Gallocyanin dye and process of making same. Dialkyl gallocyanin sulfo acids (general claim.) Nitroso dimethyl ANILIN or other nitroso alkyl amins or sulfo acids of same, condensed with PYROGALLOL sulfo or other related sulfo compound. VuioLET to BLUE acid mordant dyes. S. 633—‘‘Pyrogallocyanin, Sulfo Acid.” Note 898,040 for unsulfonated mono alkyl comp. 898,040—Sept. 8, 1908. Charles p—E LA Harrse and Rudolph BurcKkuHarpt, Switzerland. (Durand.) Gallocyanin and process of making same. Mono alkyl gallocyanins (general claims). Nitroso ethyl an1Lin or other nitroso mono alkyl arylamin or amid thereof condensed with GALLIC acid or derivs. VroLet acid mordant dye. S. 625—‘‘Chromheliotrope.” Original patent makes no reference to ‘“‘reduction” of product. Schulz tables call for this subsequent process. 898,098—Sept. 8, 1908. Charles p—E 1A Harper, Karl Oswatp and Ernst ZEHNTNER, Switzerland. (Durand.) Condensaton dye from gallocyanins and process of making same. Leuco form of methyl deriv. of dimethyl gallocyanin anilid. Nitroso dimethyl aNILIN, ANILIN and methyl Ganiic acid condensed to GALLOCYANIN anilid, then reduced in acid soln. with Zn dust. Brive acid mordant dye, used for printing. Near S. 640—‘‘Modern Azurin DH.’” 238 DIGEST OF PATENTS 898,842—Sept. 15, 1908. Charles p—E LA Harpe and Rudolf Burcxuarpt, Switzerland. (Durand,) Gallocyanin dye and process of making same. Product from condensation of nitroso diethyl ANILIN with GALLAMID is heated in autoclave at 110°-130° with 2 parts alcohol, 0.17 parts DINITROBENZENE and 3.33 parts 15 per cent alc.-NH, and separated product converted to HCl salt of leuco deriv., which is sol. in aq., in cone. H, So, (RBr) and is a green BLUE acid mordant (Cr) dye. S. 638—‘‘Amido Gallocyanin Blue.” 901,65 7—Oct. 20, 1908. Arnold STEINER, Switzerland. (Sandoz.) Gallecyanin dye and process of making same. Quinhydrone formed by action of a gallocyanin on a leuco gallocyanin. GALLOCYANIN from nitroso dimethyl ANILIN and GaALLic acid suspended in dil. HCl and Zn dust equivalent to 0.5 mol. added slowly. Or a leuco gallocyanin is partly oxidized by ammonium persulfate, or other. Or equimolecular amounts of a gallocyanin and leuco gallocyanin are heated at 50° in dil. HCl. Any mixed combination may be made. Vu1oLEtT acid mordant dye. S. 632—“Ultra Violet L, G P.’ 902,154—Oct. 27, 1908. Wilhelm LommeEt, Germany, (Bayer.) Celestin-blue sulfonic acid. Sulfa acid of diethyl gallocyanin amid. “Celestin Blue,” from nitroso diethyl ANILIN and GALLAMIC acid added to 4 parts cooled chlor sulfonic acid then heated to 90°. Brus acid mordant dye. Near S. 637—‘“‘Gallamin Blue.’”’ Addition to 663,221. 929,350—July 27, 1900. Charles VaucHER, Switzerland. (Durand.) Leueo derivatives of gallocyanin arylids, &c., and process of making same. Producing stable leuco forms* of gallocyanin arylid or sulfo derivs., that may be fixed on mordant cotton by short steaming. GALLOCYANIN anilid obtained by condensing anilin with product from nitroso dimethyl ANILIN and GALLAMID, boiled in dil. alc. soin. while HCl and formaldehyde hydrosulfite are gradually added in absence of excess free acid sufficient to split off amino-aryl group. Other components claimed. BuLur acid mordant dyes. S. 630—‘‘Cyanazurin.”’ * Classed by Schulz as dyes. 936,247—Oct. 5, 1909. Wilhelm LommeEL, Germany. (Bayer.) Gallocyanin dye and process of making. Sulfonated anilins diethyl gallocyanin. Nitroso diethyl ANILIN and GaLLic acid condensed to GALLOCYANIN, then combined with ANILIN or other, oxidized, carbo group split off and then sulfonated. Green BLUE acid mordant _ (Cr) dyes, used for printing. S. 622—‘“‘Chrom Azurin” see footnote. This patent covers specific claims, for general claims see 926,248. : 936,248—Oct. 5, 1909. Wilhelm Lommet, Germany. (Bayer.) Gallocyanin dye and process of making same. Gallocyanin aryl amids. GALLOCYANIN or derivs., condensed with ANILIN or other amin at common temp. by passing air through mixture. Green BLUE acid mordant (Cr) dyes, suitable for printing. Note Ser. 466,489. 955,040—Apr. 12, 1910. Charles Barsezat, Switzerland. (Durand.) Derivatives of gallocyanins and process of making. To obtain oxy gallocyanin without reduction to leuco dye. Anilino CELESTIN BLUE (diethyl GALLOCYANIN) heated in 37 per cent H, SO, to 75°, diluted, filtered hot. Other gallocyanin dyes are heated as above, varying acids, temps., concentration, etc. to suit dye. Tests for end of reaction are given. BuLuk acid mordant dye. Note 698,098 for leuco non hydroxylated dye. 961,361—June 14, 1910. Wilhelm Lommet, Germany. (Bayer.) Leuco derivative of diethylgallocyanin. A leuco decarboxylated diethyl gallocyanin by improved process. Nitroso diethyl ANILIN and GaALLIc acid condensed to form GALLOCYANIN as in 961,362, re- GROUP XI.—OXAZIN 239 duced with Zn and HCl, filt. and heated to 95-100° some hours, preventing access of air, till soluble in acid and insol. in carbonate solns. Brug acid mordant dye. Note 961,362 for same dye by another process. 961,362—June 14, 1910. Wilhelm LomMMmeEL, Germany. (Bayer.) Galloeyanin dye. Decarboxylated diethyl gallocyanin. Nitroso diethyl aninin and GaLLic acid condensed and boiled with alkali till soluble in acid. Buiugr acid mordant dye. Note 961,361 for leuco form by another process. 962,712—June 28, 1910. Wilhelm Lommet, Germany. (Bayer.) Leuco diethylgallocyanin. Leuco form of diethyl gallocyanin carbo acid, No. 253,721. Nitroso diethyl anin1n and Gatiic acid condensed to form GALLOCYANIN then reduced electrolytically, by Zn and HCl or by other means. S. 635—‘“‘Blue 1900, FC.” This appears to be a duplication of 639,666, (Harpe, 18099) which includes diethyl gallocyanin leuco comp. or of 257,498 which reduces with Zn. in alk. soln. 985,424—Feb. 28, 1911. Wilhelm Lommet, Germany. (Bayer.) Oxazin dye. GALLAMIC acid heated in 60° sulfuric acid with 4-nitroso PHENOL slowly to 70°. Product gives leuco comps. on reduction, modified leuco comps. with SO, or its salts, which latter are further modified by acids, all of which form chrome lakes. Brown to vioLeT acid mordant (Cr) dyes, suitable for printing, fast to washing, Cl. 992,613—May 16, 1og11. Arnold StTEe1nER, Switzerland. (Sandoz.) Process for the manufacture of coloring-matters derived from gallocyanin. Decarboxylated naphthol dimethyl amino gallocyanin. (Product also claimed.) GALLOCYANIN, from nitroso dimethyl anit1n and catuic acid, or other, condensed with RESORCIN, naphthol sulfo, or other in alk. soln. in presence of an oxidizing agent. Leuco form is made by reduction with Zn in acid soln. or by bisulfites in alk. soln. BLur to vioLer acid mor- dant (Cr) dye. S. 644—‘“Ultracyanin B.” 1,000,899—Aug. 15, 1911. Charles p—E tA Harpe and Rudolf Burckuarpt, Switzerland. (Durand.) Leuco dyestuffs of the gallocyanin series and process of making same. Leuco gallocyanin benzyl amin compounds. GaLLocyaNIN, from nitroso dimethyl aninin and Gatiic acid, condensed in alc. soln. at 50° with benzyl ANILIN, in presence of air or easily reducible comp. Product is reduced to leuco form or is dissolved and boiled in aq. Na,CO, soln. to decarboxylate then reduced. Green BLUE acid mordant (Cr) dye. Note 697,610 for use of air or nitrobenzene to prevent reduction during condensation. 1,028,045—May 28, 1912. Hans MAnsFIELD, Germany. (Badische.) Gallocyanin compounds and process of making them. Leuco form of gallocyanin compounds with dioxy tartaric acid, etc. Prune S. 636, a GALLOCYANIN from nitroso dimethyl anin1in and methyl Gatiic acid, or other, and dioxy TarRTaRIc acid or tartronic acid heated in acid soln. Brur acid mordant dye. 1,065,063—June 17, 1913. Rudolf Maac and Paul Jorc, Germany. (Hochst.) Benzoquindne derivatives and process of making same. 1.4-Dichlor 4',4”- diethoxy triphen dioxazin and derivs. CHLORANIL condensed with 4-PHENETIDIN by boiling in alcohol to form 4.4/-diphenetidin dichlor BENZOQUINONE and product boiled in nitrobenzene with sublimed FeCl,. Red powds. insol. aq. and alc., sol. in conc. sulf. (B) in boiling xylene (B-Y flour); fast violet RED pigment or lake dye. 1,138,670—May 11, 1915. Georg KrANZLEIN and Rudolf Hacenspacu, Germany. (Hoéchst.) Arylaminoanthraquinone dyestuffs and process of making same. _1-Toluidin 4-0xy 2.3-anthraquinone phenyl oxazin. OxazoL.E derived from 2-amino ALIZARIN and BENzOYL chloride or other, nitrated or chlorinated and condensed with 4-roLvIpIN or other, then sulfonated. Or oxazole first sulfonated, 240 DIGEST OF PATENTS then nitrated and condensed with amino-sulfo group in another nucleus. VioLEtT and GREEN acid and developed (CrO,) dyes. 1,188,259—June 20, 1916. Gadient Encr and Fritz GriksHABER, Switzerland. (Basle.) Leuco derivatives of sulfureted gallocyanins and process of making same. Leuco form of thio gallocyanins, GALLOCYANIN sulfur compound, derived from nitroso dimethyl ANILIN, GALLAMIC acid and Na,S, or other, reduced in acid soln. to form stable leuco dye compound. Buivug acid mordant (Cr) dye, suitable for printing, fast to washing, light. Near S. 631—‘‘Chromocyanin.”” Patent emphasizes that leuco compound is stable. 1,199,458—Sept. 26, 1916. Gadient Enc1, Switzerland. (Basle.) Halogen derivatives of gallocyanin dyestufis and process of making same, Leuco form of amid of brom dimethyl amino gallocyanin. GALLAMIN BLUE, derived from nitroso dimethyl ANILIN and GALLAMIC acid, or other gallo- cyanin, brominated or chlorinated in sulfuric acid soln. with NaBr or Br, etc., then reduced to leuco form for printing. Buus acid mordant dyes, faster to washing, light and Cl. than parent dyes, suitable for printing. } 1,268,455—June 4, 1918. Armin Gros and Jakob WurRGLER, Switzerland. (Basle.) Condensation product of gallocyanin dyestuffs with amins and process of making same. Anilin gallocyanin or other. GALLOCYANIN HCl mixed with ANILIN poured into strong peroxid soln. then heated at 100°. Other components and peroxids claimed. Green BLUE acid mordant dye, suitable for printing. Near S. 639 or 640. 1,299,070—Apr. 1, 1919. Emil WALDER, Switzerland. (Sandoz.) Manufacture of blue to greenish-blue coloring-matters of the gallocyanin series. Leuco gallocyanin amino aryl amid comp. 3- or 4-Amino BENZAMID heated with CELESTIN BLUE, or other gallocyanin at 100°, with or without oxidizing agent such as air or aromatic nitro comps. Alc. soln. can be used. Leuco comps. are formed by reduction with Zn and HCl, by hydrosulfite, etc. Bruxr to green BLUE acid mordant dyes, fast to light, soap and chlorine. Group XII.—PYRAZOLONE. 324,630—Aug. 18, 1885. H. Z1EGLER, Switzerland. (Badische.) Coloring-matter from phenylhydrazine. (Product.) 4’-Sulfanilic acid 4-azo 4”-sulfo- phenyl pyrazolone 3-carbo acid. Dioxy TARTARIC acid, Na salt, is heated at 40° in acid soln., filt., then heated at 80° in alk. ; soln. with 2 mols. phenyl HyDRAzIN sulfo acid. Product is sol. in aq. (Y), and in cone. H,S0O, (Y), almost insol. boiling alc. or glac. acetic acid, aq. soln. becomes redder with NaOH, conc. aq. soln. pptd. by alc., soln. with Pb (NO,), ppts. (OQ), with BaCl, ppts. (RO), with acid or alk. reducing agents is decol.; a YELLOW acid dye. S. 23—‘‘Tartrazin.” 627,690—June 27, 1899. J. Herpasny, Germany. (Oehler.) Yellow wool dye and process of making same. 4’/Sulfanilic acid 4-azo 4’-nitro phenyl pyrazolone 3-carbo acid. Oxalo-acetic ester, heated at 45-50° with 4-nitro PHENYL hydrazin in dil. sod. acetate soln., then at 90-100° in alk. soln. Separated 4-nitro phenyl PpyRAZOLONE carbo acid: is coupled with 1 mol. diazotized sulfanilic acid. Orange yellow powd., easily sol. aq. (Y-O), greener with acids, darker with NaOH, slightly sol. 90 per cent alc. (Y), sol. conc. H,SO, (YBr); a green YELLOW acid dye, fast to milling. S. 23—“*T'artrazin.” . ~ ; i 8 5 ; | 4 4 § ..: 2 656,857—Aug. 28, 1900. Franz ScHoLL, Germany. (Hochst.) Yellow dye and process of making same. Sulfo primulin azo phenyl methyl pyrazo- lone. PRIMULIN sulfo is diazotized and coupled in alk. soln. with phenyl methyl Pyrazotonge. A yellow-brown powd., easily sol. hot aq., (Y), fairly sol. alc., insol. ether, petroleum and benzene, sol. conc. H,SO, (Y), aq. soln. pptd. by mineral acids as gel; a direct yELLOW dye. S. 26—‘‘Dianil Yellow R.” Note 656,858 and 59. GROUP XII.—PYRAZOLONE 241 656,858—Aug. 28, 1900. F. Scuoii, Germany. (Hoéchst.) Orange dye and process of making same. Sulfo primulin azo 4’-sulfo phenyl pyra- zolone carbo. acid. PRIMULIN sulfo is coupled with 4-sulfo phenyl PyRAZOLONE carbo acid. An orange-red powd., easily sol. cold aq. (OY), almost insol. alc., insol. ether, benzene and petroleum, sol. conc. H,SO, (OY), pptd. from aq. soln. by acids; a direct orRANGE dye, fast to acid, alk., and light. Near S. 27—“Dianil Yellow 2R.’’ Note 656,857. 656,859—Aug. 28, 1900. F. Scuoiit, Germany. (Hdéchst.) Yellow azo dye and process of making same. Sulfo primulin azo 4’-sulfo phenyl methyl pyrazolone. PRIMULIN sulfo is coupled with 4-sulfo phenyl methyl pyrazotonre. An orange yellow powd., easily sol. cold aq. (OY), diff. sol. alc., insol. benzene, petroleum and ether, pptd. from aq. soln. by acid; a direct YELLOW dye, fast to acid, alk. and light. S. 27—‘Dianil Yellow 2R.” Note 656,857. 658,593—Sept. 25, 1900. F. Scuoii, Germany. (Hochst.) Green-yellow dye and process of making same. Primulin azo aceto acetic acid, ethyl ester. Primulin sulfo or xylidin deriv. is coupled with aceto acetic acid, ethyl ester, or other aliphatic beta diketones. Or primulin bases and aceto acetic acid may be coupled first and then sulfonated. Yellow powds., easily sol. aq. (Yt), soln. not changed by dil. acids or alks., darkened by strong alk., soln. conc. H,SO, (Y); direct green yELLOow dyes for cotton and acid dyes for wool. S. 25—‘‘Dianil Yellow 3G.” 679,172—July 23, 1901. Paul Juxtius, Germany. (Badische.) Orange dye and process of making same. Oxalyl acrtic ester with 2-tolyl Hyprazin HCl or other, in xyYLENE soln. is condensed at 100° and saponified to form 2-tolyl PyRAZOLONE carbo, or other, which is combined with diazo PRIMULIN sulfo. Product is diff. sol. in cold aq. (O), redder with NaOH, reduced with Zn dust in NaCl soln. yields primulin sulfo acid; orANGE developed dye, fast to soap, alk. carb., acids and light. Near S. 26—‘“‘Dianil Yellow.” 731,670—June 23, 1903. W. DotiFus and R. HacEnpacu, Germany. (Héchst.) Yellow monoazo dyestuff rand process of making same. 4-Sulfo anthranilic acid azo phenyl methyl pyrazolone. 4-Sulfo ANTHRANILIC acid is coupled in alk. carb. soln. with phenyl methyl PyRAZOLONE. A yellow powd., sol. hot ag.; a YELLOW dye suitable for lakes, fast to aq., acid, lime and light. S. 28—‘‘Pigment Fast Yellow.” 808,919—Jan. 2, 1906. J. Hacenzpacyu, Switzerland. (Geigy.) Red azo dye and process of making same. Amino naphthol sulfo phenyl methyl pyrazolon. 1-Amino 2-NAPHTHOL 4-sulfo, or other ortho amino naphthols is coupled with phenyl methyl PYRAZOLONE or other pyrazolone free to combine in position 4. Dark brown powds. with metallic luster, sol. in aq. (OY-RBr), with acetic (YR-BR), sol. conc. H,SO, (O-R); yellow-srown to violet brown acid dyes, becoming orange RED to violet red when after chromed. S. 29—‘“‘Eriochrome Red B.”’ 935,370—Sept. 28. 1909. P. Jutius and E. Fusseneccrer, Germany. (Badische.) Pyrazolone dyes and process of making them. A pyrazolone dye in which 3-chlor 5-sulfo 2-toluidin substitutes N-hydrogen in position 1 of the ring, or constitutes the azo rest, or occupies both positions. Dioxy TARTARIC acid, Na salt, heated in aq. to 50° then 70-80° with 2 mols. of 3-chlor 5-sulfo 2-tolyl hydrazin. Or 3-chlor 5-sulfo 2-roLuIpDIN may be coupled with 4/-sulfo phenyl PyRAZOLONE carbo acid in alk. carb. soln. Yellow powds., sol. in aq. (Y-YG); YELLOW acic dyes for wool or for yellow lakes, fast to light. S. 24—“‘Pigment Fast Yellow R.” 242 DIGEST OF PATENTS 935,880—Oct. 5 1909. P. VoLKMANN, Germany. (Bayer.) Yellow azo dye. 4”-Toluidin, or other toluidin, azo 4’-sulfo phenyl methyl pyrazolone. 4-TOLUIDIN, or other toluidin, is coupled with 4’-sulfo phenyl methyl PyrazoLONE or other pyrazolone. Or unsulfonated dye may be sulfonated after coupling. Yellow powds., sol. in aq. (Y), acid reduction yields original amin, sol. conc. H,SO, (Y); yELLow acid dyes of great tinctorial power, and fast. S. 21—‘Pigment Chrome Yellow L.”’ Note 935,830 and 969,428. 935,880—Oct. 5, 1909. P. VotKmMANN, Germany. (Bayer.) Azo dye. (Product.) 2”-Toluidin 5’’-sulfo azo 4’-sulfo phenyl methyl pyrazolone. 2-TOLUIDIN 5-sulfo, or other toluidin sulfo acid, is coupled with 4'-sulio phenyl methyl PYRAZOLONE or other sulfo aryl methyl pyrazolones. Or nonsulfonated pyrazolon may be coupled and later sulfonated. Yellow powds., sol. in aq. (Y), sol. conc. H,SO, (Y), giving the usual azo separation upon acid reduction; yELLOow acid dyes, level, fast to light, and of great tinctorial power. Near S. 23—‘‘Tartrazin.” 969,428—Sept. 6, 1910. P. VotKmann, Germany. (Bayer.) Greenish-yellow dye. (Product.) 2”-Sulfo-anilin azo 2/-sulfo phenyl pyrazolone carbo acid. Phenyl HypRAzIN 2-sulfo, 2 mols., condensed with 1 mol. dioxy TartTaric acid, Na salt, by boiling 2 hours in aq. containing H,SO, to neutralize the sodium present. A yellow powd., sol. conc. H,SO, (Y), giving usual azo reduction products with SnCl, and HC!; a green YELLOW acid dye, fast to light. Isomer of S. 23—‘‘Tartrazin.”” Note 972,951, which employs mixed ortho and para derivs. of first component. 972,951—Oct. 18, 1910. _ ~P. VouKmann, Germany. (Bayer.) Yellow dye. Mixture of tartrazin and 2-sulfo isomer. Phenyl uyprazin sulfo (0o- and p- sulfo mixed), 2 mols., condensed with 1 mol. dioxy. TARTARIC by boiling 2 hours in aq. soln. with sufficient H,SO, to neut. Na present. A yellow powd., sol. conc. H,SO, (Y); a green YELLOw acid dye. Near S. 23—‘‘Tartrazin.”” Note 969,428. 982,050—Jan. 17, 1911. Hugo GELDERMANN, Germany. (DBerlin.) Yellow pyrazolone dye for wool. 2”-Chlor anilin azo 2/-chlor 5’-sulfo phenyl methyl pyrazolone. 2-Chlor anILIn coupled with aceto acETic ester, then condensed with 2-chlor 5-sulfo phenyl HYDRAZIN, or pyrazolone ring first condensed, then coupled. A yellow powd., sol. in aq. and — alc., sol. conc. H,SO, (Y), pptd. on diln., pptd. by acid, with NH, or NaOH redder, neut. soln. decol. with Zn becomes violet with air; a fast yELLow acid dye. Isomer of S. 22.” Xylene Yellow 3 G.” a ee 988,870—Aug. 4, 1911. H. GeLpERMANN, Germany. (Berlin.) Yellow monoazo dye and process of making same. (Product only claimed.) 2”-Chlor anilin azo 4’-nitro phenyl methyl pyrazolone. a) 2-Chlor ANILIN is coupled with 4-nitro phenyl methyl PyRazoLoNE, or b) diazo 2-chlor anilin may be coupled with aceto acrtTic ester, then condensed with 4-nitro PHENYL hydrazin. A yellow powd., insol. in aq., alc., linseed oil varnish, diff. sol. benzene (OY), sol. conc. H,SO, (Y), pptd. on diln., decol. by Zn dust, with air (Rt); suitable for yELLOw lakes, fast to light. 1,010,919—Dec. 5, 1911. Paul Juuius and Ernst FussENEcGER, Germany. (Badische.) Pyrazolone dyes and process of making same. _ 6/-Brom 4/-sulfo 2/-tolyl azo 4- pyrazolone carbo acid azo 6”-brom 2”-toluene 4’’-sulfo. Dioxy TARTARIC acid in aq. soln. with 2 mols. of hydrazin of 6-brom 2-ToLuIDIN 4-sulfo acid Se eS ee ee ee he ar en | ery ee heated gradually to 70-80°, and product salted out. Or 1 mol. diazo deriv. of first component is coupled in alk. soln. with 4’-sulfo phenyl PyRAZOLONE carbo acid. Yellow powds., sol. in aq. (Y-GY), splits at azo bond when reduced with SnCl,; yeLLow acid dyes forming lakes fast to light. Near S. 23—Halogenated homolog of Tartrazin. GROUP XIII.—QUINOLIN 243 1,026,257—May 14, 1912. Karl Evset, Germany. (Kalle.) Manufacture of a new pyrazolone-azo dye. Chlor 1”-amino 2”-naphthol 4’-sulfo phenyl methyl pyrazolone. 1-Amino 2-NAPHTHOL 4-sulfo, chlorinated in sulfuric acid soln., neut. and condensed in alk. soln. with phenyl methyl pyrazotonr. A red powd., sol. in aq. (OR), becoming bluer with alk., sol. conc. H,SO, (VR); a red orancr acid dye which becomes violet RED when after chromed. Near S. 29—‘“‘Erio Chrome Red.”’ 1,098,600—June 2, 1914. P. VoLtKMANN, Germany. (Synthetic.) Yellow azo dyestuffs. 5”-Sulfo 2”-toluidin azo 2’-chlor 4’-sulfo phenyl methyl pyrazolone. 2-TOLUIDIN 5-sulfo acid or other toluidin or its sulfo derivs., coupled in neut. soln. with aceto ACETIC ester, then condensed with 2-chlor PHENYL hydrazin-q-sulfo, by heating to 95° in alk. aq. Or diazo comp. may be combined with a 2-chlor aryl methyl pyrazolone sulfo acid. Yellow powds., sol. in aq. and conc. H,SO, (Y), azo bond split by reduction with SnCl,; green- YELLOW acid dyes, level and fast to light. Near S. 23—‘‘Tartrazin.” Group XIII.—QUINOLIN 256,599—Apr. 18, 1882. C. H. Rupvo.pu, Germany. (Héchst.) Production of coloring-matter. (Product not process claimed.) Probably flavanilin admixed with diphenyl acetamidin and dimethyl quinolin (Richter). ACETANILID heated with ZnCl, to 230-250° with or without anittn HCl. Homologs formed by condensing with halogen alkyls or other. A YELLow basic dye. 257,717—May 9, 1882. E. Jacossen, Germany. Manufacture of red coloring-matter. Quinolin iso quinolin benzyl methane. Quinolin (crude), pyridin or other, heated with Benzo trichloride with or without ZnCl, or other condensing agent. A RED basic mordant dye, fast to soap. S. 610—“‘Quinolin Red.” 290,585—Dec. 18, 1883. E. Jacossen, Germany. Production of yellow coloring-matter., (Product also claimed.) Quinophthalone. QuINnaLDIN condensed at 190-210° with PHTHALIC anhyd by ZnCl, then sulfonated to render aq. sol. A YELLOW basic mordant and acid dye. S. 612 and 613—‘“Quinolin Yellow.” 752,323—Feb. 16, 1904. © R. Berenpes, Germany. (Elberfeld.) Sensitizing dyestuff. QuINALDIN heated at 100° with piETHYL sulfate to form NH, comp. which is dissolved in warm alc. and KOH slowly added. Methods of purification given and other components claimed. Sensitizers in distinct parts of spectrum for photo emulsions. 780,741—Jan. 24, 1905. R. BERENDES, Germany. (Elberfeld.) Sensitizing-dye. An N substituted toluquinaldin.* Tolu QUINALDIN 2.6-dimethyl quinolin or other, heated with ethyl ester of TOLUENE 4-sulfo -or other to form ammonium base then with KOH in alc. soln. A rep basic dye, used as sensi- tizer for photo emulsions. 805,143—WNov. 21, 1905. FE. K6nic, Germany. (Hoéchst.) Cyanin dye and process of making same. 4-Tolu QUINALDIN, methyl iodide, and 4-tolu QuinoLIN methyl iodide, condensed in boiling alc. soln. by adding KOH. Other components claimed. Sensitizers in red region of spectrum for photo emulsions. * According to Beacall, page 139, it is—‘‘Perikol’”? (Bayer) used for sensitizing plates to a maximum between wave lengths 590 to 560 uw. 244 DIGEST OF PATENTS 844,804—Feb. 22, 1907. B. Homoixa, Germany. (Hoéchst.) Blue quinolin dye and process of making the same. QUINOLIN, ethyl iodid, and guINALDIN, ethyl iodid, homologs or other salts warmed with alkali and FORMALDEHYDE, methylal or other body, then formaldehyde, alc. or other eliminated as solvent. A BLUE basic dye, used for sensitizing photo plates, very sensitive to light. S. 611—‘“‘Pinacyanol.” 852,158—Apr. 30, 1907. A. BERTSCHMANN, Switzerland. (Basle.) Yellow sulfin dye of the quinophthalone series and process of making same. A thio phthalo naphthoquinone. b-Sulfo pHTHALIC acid (or disulfo) treated with PCl, to form the sulfo chloride, reduced with Zn to b-thio FHTHALIC acid, then heated with 2-naphtho QUINALDIN, or homologs. An ORANGE or YELLOW sulfide or reducing vat and developed (CrO,;) dye, which when oxidized on fiber is fast to washing and light, and is suitable for printing. 890,58S8—June 9, 1908. E. Mrtyer, Germany. (Elberfeld.) Yellow dye. Sulfonated chlor quino phthalone. 4-Chlor ANILIN, ACETALDEHYDE and HCl condensed to form 4-chlor QttINALDIN, heated at 210° with PHTHALIC anhyd., and resulting chlor quino phthalone sulfonated. A green-YELLOW acid dye, (in alc. soln.), suitable for lakes, faster to light than those of Quinolin Yellow. S. 613—“‘Quinolin Yellow, aq. sol.’? (chlorinated). 1,197,632—Sept. 12, 1916. E. Horra, Germany. (Hochst.) Quinophthalonesulfonie acids containing halogen and process of making same. Chlor iso-quino phthalone. Chlorinated in ortho position to N, thus differing from 890,588. 3-Chlor ANILIN condensed at 100° with PARALDEHYDE to form 2-chlor 8-QUINALDIN then heated at 200-210° with PHTHALIC anhyd, separated and sulfonated. A yELLOW acid dye, fast to light. S. 613—“Quinolin Yellow, aq. sol.’ 1,338,346—Apr. 27, 1920. L. E. Wist, New York, and E. Q. Apams, California. (U. S. Gov't.) Process of making photographic sensitizing-dyes of the isocyanin type. Isocyanin dyes from quinolin by improved process. 4-Tolu QUINALDIN, methiodide, or ethiodide, and 2 mols. QUINOLIN methiodide (anhydrous) heated in open vessel in absolute methyl alcohol, sodium methylate added, and soln. evaporated to 0.8 volume to cryst. dye. 1,338,349—Apr. 27, 1920. E. Q. Apams, California, and L. E. Wisz, New York. (U. S. Gov’t.) Process of making photosensitizing-dyes effective for infra-red radiation. Infra-red sensitizers from quaternary halide derivs. of a, y dimethyl quinolins. 2.4.6-Trimethyl QurINoLIN ethiodide dissolved in abs. methyl alcohol, sod. methylate added and let stand 2 days in open vessel at room temp. Photo sensitizing dyes in infra-red. 1,374,871—Apr. 12, 1921. E. Q. Apams, Cal., and H. L. Hauer, Ohio. Photosensitizing dye of the isocyanin type. Action of strong bases on quaternary addition products of y methyl a-unsubstituted pyridin bases. Lepip1n methiodide, or deriv., heated to boil in abs. methyl alcohol, sod. methylate added, boiled, cooled slowly and let stand 24 hours. Other alfa methylated and gamma unsubstituted pytidin bases are claimed. 1,374,872—Apr. 12, 1921. Elliot Q. Apams, California, and Herbert L. Haier, Ohio. Photosensitizing dye effective for infra-red radiation. Same process and claims as in 1,374,871, using quinolin bases instead of pyridin. GROUP XIV.—STILBENE 245 1,437,674—Dec. 5, 1922. Samuel PaLx1n, Connecticut. (U. S. Govt.) Process of making photographic sensitizing dyes of the dicyanin type. 2.4-Dimethyl 6-ethoxy QUINOLIN ethiodide or derived ethnitrate in soln. of Na,S in 95 per cent alc. (1:4) is heated at 50° or let stand at usual temp. with 4 parts CHCl,. The trimethyl deriv. may be used, and other quaternary addition products of alfa gamma dimethyl quigolin derivs. Group XIV.—STILBENE. 350,229—Oct. 5, 1886. F. Benper, Germany. (Leonhardt.) Yellow coloring-matter. 4.4’/Diamino 2.2/disulfo stilbene disazo diphenol, or other. _ 4-Nitro TOLUENE heated with fuming sulf. acid to form ortho mono sulfo comp., converted to the Na salt, 2 mols. of which are condensed by heating with conc. NaOH to a sTILBENE, then reduced in acid or alk. soln. to the amino sulfo deriv., which is tetrazotized and coupled with PHENOL, 2 mols. salicylic acid, or other. Brown powds., easily sol. cold aq. (O), soln. turning red with NH, or NaOH, pptd. blackish blue by HCl, sol. conc. H,SO, (V); direct yELLow dyes for cotton. S. 303—“Brilliant Yellow’; S. 305, “‘“Hessian Yellow.’’ Note 350,230 and 395,115. 350,230—Oct. 5, 1886. F. Benner, Germany. (Leonhardt.) Red coloring matter. 4.4’/-Diamino 2.2’-disulfo stilbene disazo dibeta dinaphthylamin or a disulfo deriv. 4-Nitro TOLUENE, sulfonated, Na salt of sulfo comp. condensed in conc. NaOH to a sTILBENE, reduced to amino comp., tetrazotized and coupled with 2 mols. 2-NAPHTHYLAMIN, its 6-sulfo acid, or other. Brown-red powds., sol. in aq. (V) and in conc. H,SO, (B), aq. soln. with HCl gives blue ppt.; direct vioLer dyes for cotton. S. 301 and S. 302—‘‘Hessian Purple.’”? Note 350,229 and 395,115. 360,553—Apr. 5, 1887. F. Benper, Germany. (Leonhardt.) Production of disulpho-acid of diamido-stilbene. Distilbene tetra ortho sulfo azoxy azo or disazo diamino or diphenol comp., etc. 4-Nitro TOLUENE 2-sulfo, 2 mols., condensed in strong alk. soln., then reduced with Zn dust in alk. soln. or SnCl, in acid soln., tetrazotized and coupled with amines, phenols, etc. 2.2!- Disulfo 4.4’-diamino st1LBENE is a yellowish powd., slightly sol. aq. and alc., easily sol. alk., which solns. are pptd. by acids. The derived azo dyes are yELLOW direct dyes for cotton, acid dyes for wool. S. 9—“Sun Yellow.”’. Note 350,229 and 30. 386,709—July 24, 1888. W. KELBE, Germany. (Berlin.) Production of coloring substances by the reaction of aromatic hydrazin sulphonie acids on retenchinon. Compos. probably retene disazo di-sulfanilic acid, or other. One mol. RETENQUINONE boiled in aq. soln. with 2 mols. PHENYL hydrazin sulfo acid, or other aromatic hydrazin sulfo acid, néut. with soda and salted out. Products are orange RED to violet red acid dyes, fast to soap and alk. 395,115—Dec. 25, 1888. F. Benner, Germany. (Leonhardt.) Production of coloring-matter. (Product, not process, claimed.) Benzylated Cur- cumin S, or other. 4-Nitro TOLUENE 2-sulfo, 2 mols., condensed to yellow dye by NaOH, as in 350,229, refluxed with 30 per cent NaOH, alc. and BENzyt chloride, or other. Or nitro toluene sulfo acid may be nitrated, brominated, alkylated, etc. Product is sol. in aq. (Y), pptd. by NaCl or BaCl, (Y), not reddened by NaOH; a yeELLow direct and acid dye for cotton and wool, fast to soap and alk. S. 304—‘‘Chrysophenine G.” Note 350,229 and 30. 396,527—Jan. 22, 1889. F, Benner, Germany. (Leonhardt.) Production of coloring-matter. (Product, not process, claimed.) Azoxy azo and disazo distilbene tetra ortho sulfo acid. 4-Nitro TOLUENE 2-sulfo, 4 mols., condensed and reduced by boiling in dil. alk. soln. with ale., glycerin, and an oxidizable substance, inorganic or organic. Part reduction gives azoxy 246 DIGEST OF PATENTS azo and complete reduction the disazo form. A brown powd., sol. in aq. (Y), soln. scarcely altered by NaOH, pptd. by BaCl, (BrR), decol. by NaOH and Zn dust, and reoxidized by air (R), sol. conc. H,SO, (R-BV); a direct yELLow dye, fast to alk. and soap. S. 1r1—‘‘Mikado Orange G.” Note 360,553. 455,952—July 14, 1891. C. Ris, Switzerland. (Geigy.) Brown dyestuff. 4.4’-Dipara-diamino diphenyl disazo 2.2 -disulfo stilbene. 4-Nitro TOLUENE 2-sulfo, 2 mols. condensed with 2 mols. 4-PHENYLENE DIAMIN, or other, in hot NaOH soln. A brown powd., sol. aq. (YBr), conc. H,SO, (RV) and methyl alc., less sol. in ethyl alc. and glac. acetic, scarcely sol. in benzene and ether; a Brown direct dye for cotton, that may be diazotized and coupled on the fiber with naphthols, phenols, or amins, to obtain RED, BROWN, or BLACK developed colors, fast to soap. S: 15—‘‘Polychromin B.” 601,063—Mar. 22, 1808. C. Ris. (Geigy.) Benzidin-orange. (Process also claimed.) 2.2’-Disulfo stilbene disazo di-benzidyl. 4-Nitro TOLUENE 2-sulfo, 2 mols. condensed in alk. soln. with 1 mol. BENzIDIN, or other. A direct ORANGE dye for cotton. S. 15—‘‘Chicago Orange.” 613,911—Nov. 8, 1808. C. Ris, Switzerland. (Geigy.) Yellow dye and process of making same. Diphenyl 4.4’-disazo stilbene 2.2’-disulfo or 4-phenyl azoxy 4/-nitroso 2.2/-disulfo stilbene. 4.4/-Dinitro DIBENZYL 2.2/-disulfo condensed at 40-80° with ANILIN or other base of this series, and oxidized with NaOCl or persulfate at 60-80°. An orange-yellow powd., easily sol. aq. (Y), and cone. H,SO, (O), scarcely sol. alc., azo bond severed by reducing agents (Zn and HCl), becomes greener on treatment with hypochlorite or persulfate; green yELLOW direct dyes for all fibers. S. 12—“‘Diphenylcitronin G.”’ 636,065—Oct. 31, 1899. C. Ris, Switzerland. (Geigy.) Stilbene azo dye. 4-Nitroso 2.2’-disulfo stilbene 4’-azo para amino benzene, para ethoxy benzene, the disazo distilbene comp., or others. 4-Nitro TOLUENE 2-sulfo, 2 mols., condensed in hot, strong NaOH soln. with 1 mol. 4-PHENY- LENE DIAMIN by heating to 98°. Alkylated components are claimed and other amins, phenols and aryl acids containing at least one amino group. Products are sol. in aq. (Y-O) im cone. H,SO, (R-VR), diff. sol. alc., insol. ether and benzene, pptd. with mineral acid (BrBk-BBk), upon reduction yield one original component unchanged; YELLOW to ORANGE tO BROWN direct dyes for cotton. ‘ S. 13—‘‘Polychromin B.” 951,046—Mar. 1, 1910. A. Buanxk and W. Ropionow, Germany. (Bayer.) Yellow to brown dye. Direct yellow with N-oxygen replaced by phenetidin. ; Azoxy azO DISTILBENE tetra-o-sulfo (Direct Yellow from 4-nitro TOLUENE 2-sulfo and NaOH), or other dye produced from 4-nitro toluene and NaOH, condensed with 4-PHENETIDENE or other aromatic amin by refluxing in alk. soln. for 20 hours. A yellow-brown powd., sol. in ag. (Y), in conc. H,SO, (BR), and pptd. on diln. as brown flakes; direct YELLOW to ORANGE to BROWN dyes, fast to light and oxidizing agents. S. 14—‘‘Diphenylchrysoin G.’”’ Note 951,047-48, S. 16—‘“‘Curcuphenine” and 951,049. 951,047—Mar. 1, 1910. A. Bianx and W. Ropionow, Germany. (Bayer.) Yellow to brown dye. Direct yellow with N-oxygen replaced by amino azo benzene. Azo azoxy DISTILBENE tetra-o-sulfo, or other dye obtained by treating 4-nitro TOLUENE sulfo acid with NaOH, condensed with amino azo BENZENE sulfo or other aromatic amino azo comp. by refluxing 20 hours with dil. NaOH. Brown to black powd., sol. in ag. (Y-O-Br), sol. conc. H,SO, (VBk), pptd. on diln. (Br); direct YELLOW to ORANGE to BROWN direct dyes. Note 951,046. 951,048—Mar. 1, 1910. A. BLANK and W. Roptonow, Germany. (Bayer.) Orange to brown dye. Direct yellow with N-oxygen replaced by dehydro thio toluidin sulfo. Azo azoxy DISTILBENE tetra-sulfo (from 4-nitro TOLUENE 2-sulfo and NaOH) and dehydro thio ToLuIpIN sulfo or other heterocyclic amin condensed by refluxing 20 hr. in dil. NaOH. GROUP XV.—SULFUR 247 Brown powds., sol. in aq. (O to Br), sol. conc. H,SO, (BR), pptd. on diln. (Br); oraNcE to BROWN direct dyes. S. 16—“Curcuphenine.” Note 951,046. 951,049—Mar. 1, 1910. A. BLankK and W. Ropionow, Germany. (Bayer.) Reddish-brown cotton dye. Direct yellow with N-oxygen substituted by sulfanilic azo 1- naphthylamin. Azo azoxy DISTILBENE tetra-sulfo (from 4-nitro TOLUENE 2-sulfo and NaOH) condensed with SULFANILIC aZ0 NAPHTHYLAMIN. Yellow brown powd., sol. in aq. (Br), sol. conc. H,SO, (V), pptd. on diln. (Br); red-prown direct dye. Note 951,046. Group XV.—SULFUR. A distinction has been made between hydrosulfite or “reducing vat” dyes and “sulfide vat” dyes, in which NazS acts as a solvent of the reduced dye. Both are in fact in the reducing vat class and many sulfur dyes, thrown out of NaeS solution by acid, are subsequently dyed in hydrosulfite vat. 523,138—July 17, 1894. Raymond Vipat, France. Black dye. (Process only claimed.) QuINONE or other ortho or para dioxy benzene, heated with $, NH,Cl and NaOH in closed vessel at 160-210°. NH, must be freed. Treated with sulfuric acid, black dye is pptd. while soln. gives RED to BLUE direct dye on oxidation. Product is a BLAcK sulfide vat dye. 5623,138—July 17, 1894. (Re. 11,659)—Apr. 5, 1808. Raymond VipaL, France. Black dye and process of making same, : QUINONE, hydroquinone, or any ortho or para dioxy benzene, heated in open or closed vessel to 130-210° with S and NH,, or fatty amin. Product is sol. alk. and sulfites and may be sulfonated, ppt. forming sBLacxk sulfide vat dye, and liquor on neutn. and oxidation a BLUE direct dye in neut. bath or rEp acid dye in acid bath. 532,484—Jan. 15, 1895. Alcide F. Porrrier, France. (St. Denis.) Sulfur dye. (Process claimed.) p-Dioxy tetra phene trithiazine. (Green.) 2.7- or 2.6-Dioxy NAPHTHALENE or other doubly- substituted benzene deriv., with sulfur, NH,Cl and Na,S heated to 175-200° in open or closed vessel. Patent employs also naphtho- quinones, 4-phenylene diamins, 2-diamins, naphthalene diamins, nitramins, amino-azo-benzene, indamins, cresylene diamins, etc. Gray or bronzy powds.; BLack sulfide vat dyes. See 532,503. 532,503—Jan. 15, 1805. Raymond Vipayu and Alcide F. Porrrizr, France. (St. Denis.) Sulfur dye. (Process only claimed.) Nitroso I1-NAPHTHOL heated with S and Na,S to 190-200°. Other nitroso phenols, amino phenols, or nitro phenols, etc., are claimed, the latter being reduced by Na,S before sulfur is added to melt. Buracx sulfide vat dye. S. 717—“Vidal Black. Addition to 532,484. 545,336—Aug. 27, 1895. Réne Boun, Germany. (Badische.) Black dye. 1.8 or 1.5-Dinitro NAPHTHALENE boiled in aq. Na,S soln., then in strong HCl, or acetic acid. Ppt. contains two dyes, sol. and insol. in soda and methods for separation are given. Patent claims generically the mixed dyes and specifically the alk. insol. portion, which forms a blue black paste or black powd. with coppery luster, almost insol. NaOH, H,SO, and alc., and is a BLACK reducing vat dye. S. 740—‘“‘Fast Black B.” Note 545,337, for specific claims on alk. sol. portion. 545,337—Aug. 27, 18905. Rene Boun, Germany. (Badische.) Black dye. 1.8 or 1.5-Dinitro NAPHTHALENE stirred in aq. Na,S soln, cold, and acetic acid added to ppt. dye. Two products, alk. sol. and insol. are separated, the first being claimed by this patent. 248 DIGEST OF PATENTS Green blue paste, or blue black powd., sol. in boiling soda (V), in conc. sulf. (G) on heating (B-R), insol, in alc.; a BLACK alk. or reducing vat dye. S. 740—‘‘Fast Black B.” Specific claims for alk. insol. portion are 1n 545,336. 546,576—Sept. 17, 1895. Rene Boun, Germany. (Badische.) Black coloring-matter. (Process claimed.) 1.8- or 1.4-Dinitro NAPHTHALENE is converted as in 545,336, by boiling in dil. Na,S then with excess HCl, into a dye which is largely insol. in soda, dye ““B”, which is digested at 100° in equal parts 23 per cent NaOH and resulting bath used for dyeing, or dried. A black powd., easily sol. in aq. (BV-Bk), not pptd. by alk., pptd. by acids, sol. in conc. sulf. (dull G); a BLACK vat dye. S. 741—‘“Fast Black BS.” 560,334—May 109, 1806. Moritz Unricu, Germany. (Bayer.) Black dye. (Process claimed.) 1.4- or 1.5-Dinitro 8-cHLOR NAPHTHALENE, boiled in aq. soln. with 5 parts Na,S, filtrate acidified and boiled. Green black powd., insol. in aq., alc., H,SO, but sol. in hot NaOH or Na,S; gray BLUE to BLACK vat dyes, 561,276—June 2, 1896. Alcide F. Porrrrer, France. Sulfureted dye. (Process claimed.) Acetyl 4-PHENYLENE DIAMIN, or other diamin or corresponding azo or nitro derivs., etc., heated with 2 parts S to 200-250°. Alk. sulfide may be used with S. Froducts are sol. in aq., in alk. sulfids, sulfites, and bisulfites, insol. in acids; yELLOw to bronze YELLOW to BROWN reducing vat dyes. S. 715—‘‘Thiocatechine.’”’ Note 532,484 and 532,503. 561,277—June 2, 18096. Alcide F. Porrrier, France. (St. Denis.) Sulfureted dye. (Process claimed.) CRESYLENE DIAMIN, nitro 4-toluidin, or other meta diamin of benzene series heated at 200-225° in two parts Na,S. Products are sol. in aq., alks., alk. sulfide (BrR), insol. in acids; YELLOW to BROWN sulfide vat dyes, fast to washing and exposure. Near S. 710—‘‘Immedial Yellow D.” Addition to 532,503. 594,105—Nov. 23, 1897. Henry R. Vipat, France. Sulfur dye. (Process claimed.) Resorcin, heated with NH, and S to 260° in closed vessel. Other meta dihydroxy, or amino oxy, diamino, sulfonated or triamino derivs. of benzene are claimed. Products are brown to black powds., sol. in Na,S (Br); BROWN or BLACK sulfide vat dyes. Near S. 717—‘‘Vidal Black Y.” 594,106—Nov. 23, 1897. Henri R. Vina, France. Mixed sulfur dye. (Process claimed.) 4-PHENYLENE DIAMIN and HYDROQUINONE, equal parts, heated in sulfur. Two colors are formed, one soluble in acids, the other soluble in alkalies; BLAcK acid or dull BLUE alk. vat dyes. 594,107—Nov. 23, 1897. Henri R. Viva, France. Thiazin dye. (Process only claimed.) 4.4’-Dioxy thiazine, and 4-amino 4/-oxy thiazine. 1.4-Amino PHENOL, with or without 4-PHENYLENE DIAMIN, and HYDROQUINONE heated with S. Brack sulfide vat dyes, (not claimed). Note 601,363 and 601,364. 596,559—Jan. 4, 1898. Arthur WEINBERG, Germany. (Cassella.) Brown sulfureted dye. (Process claimed.) Dinitro crEeso, heated with 1-3 parts S and 4-6 parts Na,S to 100°. A BRown sulfide vat dye. Near S. 725—‘‘Immedial Dark Brown A.”’ GROUP XV.—SULFUR 249 597,983—Jan. 25, 1808. Max H. Isier, Germany. (Badische.) Black substantive cotton-dyestuff. (Process claimed.) 1.5-Dinitro ANTHRAQUINONE or other nitro, amino or sulfo anthraquinones, heated with Na,S and § till soluble in aq. Product is sol. in aq. (B), in conc. sulf. (GyBk), slightly sol. in alc. (G), insol. in acids, sol. in alk. and alk. sulfids; a spracx sulfide vat dye, fast to light, acids, soap, Cl. S. 749—“Anthraquinone Black.’’ 601,363—Mar. 29, 1808. Henri R. Vina, France. Thiazin dye. Tetraphene trithiazine products with OH or NH, in para position in each end nucleus. 1.4-Dioxy THIAZINE, Of 4-amino 1-oxy thiazin (or mixture of 4-amino PHENOL and 1.4-PHENY- LENE DIAMIN) heated with S and NH, to 170-220° in closed vessel. Para substitution products of thiazines, or mixtures yielding same, are claimed. Black powds., sol. in conc. sulf., in sulfites and hot alks.; puacKx sulfide vat dyes. (not claimed). Addition to 594,107. 601,364—Mar. 29, 1808. Henry F. Vipau, France. Process of obtaining dyes from sulfanilie acid. SULFANILIC acid and 4-amino PHENOL heated at 170° (boiling temp.) for 2-3 hours. Other amino phenols or naphthols and analogs of sulfanilic acid are claimed. Buiue to violet BLUE vat dyes. Note 608,354 for specific claims. 601,365—Mar. 20, 18098. Henri R. Vipat, France. Black dye. (Process also claimed.) SuULFANILIC acid, or other amino sulfo aryl derivs., 4-amino PHENOL, or other amino phenols, naphthols, diamins, etc., heated in strong NaOH till dissolved, sulfur added and temp. raised to 170°. Dark poreus mass, insol. in acids, sol. in alks. (BBk), darker in air; sBLacK sulfide vat dyes. Note 608,355 for specific claims. A 603,755—May 10, 1898. _ Robert Demutu, New York. (Bayer.) Brown sulfur dye. (Process also claimed.) CreEsoL, either crude, the separated isomers or mixtures, heated with strong NaOH and S to 270°. Brown black powd., insol. in aq., alk. carb., NH, alc., diff. sol. NaOH (GBr), insol. conc. sulf., sol. in alk. sulfids (GBr); fast Brown sulfide vat dyes. 606,193—June 28, 1808. Robert Demutu, Germany. (Elberfeld.) Yellow-brown cotton-dye. (Process also claimed.) 2.4-Dinitro TOLUENE 6-SULFO, heated with soln. of Na,S and S to 200-250°. Dark brown powd., easily sol. in aq. (RBr), not changed by Na,S, pptd. from soln. by acids (Br); yellow BROWN sulfide vat dyes, fast to alks. and light. Near S. 722—‘‘Auronal Black N.”’ 608,354—Aug. 2, 1898. Henri R. Vipat, France. Process of making violet dyes. SULFANILIC acid and 1.4-PHENYLENE DIAMIN or 1.4-naphthalene diamin heated to 170-225° (boiling temp.) 2-3 hours. Products are sol. in acids (V), in alks. (VBk); dark viouer direct dyes (not claimed). 608,355—Aug. 2, 1898. Henri R. Vipat, France. Brown-black sulfur dye. (Process claimed.) SuULFANILIC acid, or other aminobenzene sulfo acid, and 2-amino PHENOL, or other amino phenol or diamin, heated with sulfur to 170-200° and dye dissolved out with alkali. Dark mass, sol. in alks., insol. in acids; BROWN to BLACK vat dyes. Note 601,365. 250 DIGEST OF PATENTS 610,541—Sept. 13, 1898. Georg KaiscHER, Germany. (Cassella.) Black dye and process of making: same. 1.3-Dinitro 4-chlor BENZENE, or the nitro amino or diamino compound condensed with 4-amino PHENOL in alc. sol. in presence of acetates, to 4-oxy 2/.4'-dinitro DIPHENYLAMIN, which with Na,S and § is heated to 140-160°. A black mass, sol. in aq. (BBk), pptd. from soln. by acids; a blue BLACK vat dye. S. 724—‘‘Immedial Black.” Note 628,607 and 628,609 for sulfo derivs., 639,806 for similar components and process, 651,077 for chlorine deriv., and 692,174 for use of Cu in melt. 611,112—Sept. 20, 1808. Emil E.sarsser, Germany. (Dahl.) Blue-black dye and process of making same. 1.8-Dinitro NAPHTHALENE 4-sulfo soln. in cold aq. added to soln. of Na,S in® aqi=e “Dark powd., readily sol. in aq. (B-Bk), sol. conc. sulf. (BrBk), pptd. on diln. (Br); sLuE to blue BLACK (Cr and Cu) vat dyes, fast to washing and light. Near S. 740—‘‘Fast Black B.” 611,610—Oct. 4, 1898. Robert DEMutH, Germany. (Elberfeld.) Brown cotton-dye. (Process claimed.) I-NAPHTHOL 4.8-disulfo, treated with Na,S and S in aq. soln. in closed vessel at 260—-270°. A black mass or powd., sol. in aq. (RBr), unchanged by Na,S, pptd. from soln. by acids (Br); red BROWN alk. vat dyes, fast to alks. and light. 611,611—Oct. 4, 1808. Robert DEmutTH, Germany. (Elberfeld.) Indigo-blue cotton dye. (Process claimed.) | I-AMINO 8-NAPHTHOL, heated in closed vessel with Na,S, sulfur and aq. to 200-240°, melt extracted with aq., and soln. pptd. with NaCl, ZnCl,, etc. A black powd., insol. in aq., alk. carb. or HCl, largely sol. in NaOH, 40° (B), in conc. sulf. (dull VR), in hot aq. Na,S (Br), turning with air to (B); a BLUE alk. reducing vat dye, fast to alks. and light. Note 614,538. 614,538—Nov. 22, 1808. Robert DEMutH, Germany. (Elberfeld.) Indigo-blue dye and process of making it. I-AMINO 8-NAPHTHOL 2.4-disulfo, or other disulfo deriv., heated dry with Na,S and §S to 200-240°. Dye extracted from melt with hot aq. and pptd. by ZnCl, salt, etc. Dark powds., insol. in aq., alk., carb., and HCl, sol. in 40° NaOH (B), in conc. sulf. (dull VR), in dil. NaS (Br), turning in air to (B); BLuE reducing vat dyes, fast to alks., light. Note 611,611 618,152—Jan. 24, 1899. Henri R. Vipat, France. Black sulfur dye. (Process claimed.) 2.4-Dinitro PHENOL, 2.4-diamino PHENOL, the corresponding naphthols or other trisubstituted derivs., heated to 140° with Na,S and S. Black powds., sol. in alk. sulfide, in alks., and in acid bichromate solns.; BLACK sulfide vat dyes. S. 720—‘‘Sulfur Black.” This patent appears to duplicate 655,659. Schulz credits it to Priebs and Kaltwasser, 1899. 620,428—Feb. 28, 1899. Robert Demutu, Germany. (Elberfeld.) Blue cotton dye. 1-Chlor 8-NAPHTHOL 2.4-disulfo or mono sulfo, in alk. soln. with Na,S and S, or other poly sulfids, heated to 200-240°, melt extracted by aq., and pptd. by ZnCl, or salt, ete. Dark powd., insol. in aq., alk. carb., and HCl, largely sol. in 40° NaOH (B), in conc. sulf, (dull VR), in hot dil. NaS (Br), turning with air to (B); BLuE reducing vat dyes, fast to alk. and light. 622,299—Apr. 4, 1899. Henri R. Viva, France. Black dye and process of making same. Gun corron (hexa NITRO CELLULOSE) or other nitro aromatic substance from cellulose material heated with Na,S and S and water to 280°. Brown sLacK to deep sack sulfide vat dyes. +e: _ GROUP. XV.—SULFUR 251 626,897—June 13, 1890. Friedrich Fucus and Hermann GussmMAnNn, Germany. (Hochst.) Black sulfur dye and process of making same, 2.4-DINITRANILIN or diamino nitrobenzene heated with Na,S and S to 150° then to 230— 240°: Black hygroscopic powds., sol. in aq., pptd. by acids (Bk), sol. in alk. sulfide or caustic; BLACK sulfide vat dyes, (cold bath), fast to alks., acids, light. 628,607—July ‘Ti, 1899. . Bernhard Prigss and Oskar KattwassEr, Germany. (Berlin.) Black dye. 2-Nitro 1-chlor BENZENE 4-sulfo condensed with 4-amino PHENOL to form 4’-oxy 2-nitro DIPHENYLAMIN 4-sulfo, which with Na,S and S is heated to 140-150° then at 180-200°. Product is easily sol. in aq. (GB), in fuming sulf. (GyG-GGy), soln. pptd. by air (Bk-BGy); fast BLACK vat dye. Near S. 724—‘Immedial Black.”’ Note addition patent 628,609, original pat. by Kalischer, 610,541 and 641,100. 628,608—July 11, 1899. Bernhard Prigss and Oskar Ka.twassErR, Germany. (Berlin.) Black dye. 4.2-Dinitro 2’.3’-carbo DIPHENYLAMIN, obtained by interaction of 2.4-dinitro chlor BENZENE and 4-amino sALIcyLic acid, heated in sulfur melt at 130-140°, then at 160-170°. Product is sol. in aq., (GB), in fuming sulf. (GyG), pptd. on diln. (BBk), pptd. by air (dull B); fast deep BLACK alk. vat dye. 628,609—July 11, 1899. Bernhard Priess and Oskar Kaitrwasser, Germany. (Berlin.) Bluish-black dye. 4.2-Dinitro 1-chlor BENZENE, condensed with 4-amino PHENOL 2-sulfo to form 4’-oxy 4.2- dinitro 3’-sulfo DIPHENYLAMIN, which is heated with Na,S and S to 140-160°. Product is sol. in aq. (B), in fuming sulf. (GyB), pptd. on diln..(V), pptd. by air; blue BLacxk sulfide vat dye. Near S. 724—‘‘Immedial Black.’”? The same as 724 except above employs sulfo deriv. in first component. See also original patent by Kalischer, 610,541 and 628,607. 629,221—July 18, 1899. Henri R. Viva, France. Cresol-sulfur dye and process of making same. ANILIN diazotized and coupled with crEsoL (o or m), heated with soda and sulfur to 180° until anilin is distilled off, then temp. raised to 240°. Black brittle substances, sol. in aq., pptd. by acids, sol. in alk. sulfids; BLack (ortho deriv.) or BLUE (meta comp.) sulfide vat dyes that do not require oxidation on fiber. Note 523,138, 532,484 and 532,503. 630,952—Aug. 15, 1809. Henri R. Vipat, France. Substantive sulfur dye and process of making same. ANILIN and RESORCIN, the disazo resorcin or dioxy naphthalene comps. or the amino or diamino dioxy derivs. of naphthalene (products by reduction of above) heated with Na,S and S at 220-280°. Black brittle mass, sol. in aq., giving VARI-COLORED dark shades as sulfide vat dyes. 632,170—Aug. 29, 1899. Rene Boun, Germany. (Badische.) Blue dye and process of making same. 1.2-Dinitro NAPHTHALENE, reduced by alk. bisulfite, Na,S and glucose, or other, then heated with Na,S and S to 90-100°. Buiue reducing sulfide vat dyes. S. 743—‘‘Kryogen Brown A.” Note 674,137 for similar patent and apparent duplication. Addition to 609,327. 635,168—Oct. 17, 1899. R. KircHHoFF and E. HaussMann, Germany. (Berlin.) Black sulfur dye. 2.4-Dinitro 4/-oxy DIPHENYLAMIN, 1 mol., or derivs. and 1 mol. 4-amino PHENOL, heated with Na,S and S to 110-160°. 4-Phenylene diamin, or nitro derivs. may be used. Products are sol. in aq. (GB), with NaOH bluer, pptd. by acids, air or CO, (BrBk), sol. conc. sulf. (dull BrG), in fuming sulf. (BBk); green sLack sulfide vat dyes, that do not require oxidation on fiber. Patent does not state whether product is a single compound, or mixture of sulfur dyes produced from separate components. Note 610,541 and 625,717. 17 252 DIGEST OF PATENTS 635,169—Oct. 10, 1899. R. Krrcuuorr and E. Haussmann, Germany. (Berlin.) Black sulphutur dye. 2.4-Dinitro 4’-oxy DIPHENYLAMIN and equimolecular proportion of 3-PHENYLENE DIAMIN heated in Na,S and S at 120-125° then at 150-160°. Other components cla‘med. Brack sul- fide vat dyes. Near S. 724—‘‘Immedial Black.” Note 610,541 and 625,717, 561,277 and 594,105. 636,066—Oct. 31, 1899. Christopher Ris, Switzerland. (Geigy.) Black-cotton dye. 4-Amino PHENOL or deriv., mixed with ACETANILID or other acetyl aryl comp., with or without diluent such as GLYCERIN, etc., heated with sulfur at 210-230°,, till H,S ceases to evolve. Black powds., easily sol. in aq. (GBr), in conc. sulf. (GBk), insol. alc., ether, C,H,; BLACK sulfide vat dyes. 639,806—Dec. 26, 1899. W. H. Craus, A. REE and Leon Marcuiewsk1, England. Black sulfur dye. (Process only claimed.) 2/-Oxy 2.4-dinitro DIPHENYLAMIN, heated with Na,S and S to 140-160°. A BLAcK reducing sulfide vat dye, fast to light, acids, alks. Near S. 724—‘‘Immedial Black.”” Use of ortho hydroxy compound instead of para, claimed as new, see 610,541. 640,559—Jan. 2, 1900. Otto Hansmann, Germany. (Berlin.) Brown sulfur dye. 4-Nitro 1-chlor BENZENE 2-sulfo, condensed with 3-TOLUYLENE DIAMIN by refluxing with aq. in presence of CaCO, until CO, ceases to evolve, filt., filtrate pptd. by acid and dried product heated at 180-200° with Na,S and S. A brown black powd., sol. in aq. (Br), un- changed by NaOH, pptd. by acids (Br), sol. conc. sulf. (dull VR), pptd. on diln. (Br), diff. sol. alc. (Br); a Brown sulfide vat dye turning to bronze when after treated with CaSO, and KOCr0.. Near 737—‘‘Cotton Brown.” 641,587—Jan. 16, 1900. Arthur G. Green and A. Mryenserc, England. Process of making black sulfur dye. 4-PHENYLENE DIAMIN mixed in dil. HCI soln. with 1 mol. anrnin HCl, about 5 parts Na,S,0, dissolved in this soln., then Na,Cr,O, and excess sulf. acid added, keeping temp. below 5°, finally soln. is boiled. Para amino phenol and other paradiamines and bases of benzene series are claimed. : Note 641,588 and 89 for product pat. and homologous dyes. 641,58S—Jan. 16, 1900. Arthur G. Green and Alex. MEYENBERG, England. Blaek sulfur dye. oS oe ae 4-PHENYLENE DIAMIN mixed in dil. HCl soln. with anizin HCl, nearly 5 parts cryst. Na,S,O, added, then sod. bichromate and excess sulf. acid, with temp. kept below 5°, and soln. finally boiled. Other para diamines and other bases of benzene series are claimed. Brack reducing sulfide vat dyes, fast to acids, alks., soap, light, and air, and may be developed by copper salt and bichromate. This is product patent for process 641,587. Note also 641,589. 641,589—Jan. 16, 1900. Arthur G. Green and Alex. Mryenserc, England. Black sulfur dye. i ’ a * % 4-TOLUYLENE DIAMIN mixed in HCI soln. with 1 mol. anizin HCI or 2-toluidin HCl, nearly 5 parts Na,S,O, dissolved in bath, then bichromate and excess. sulf. acid added while temp. is kept below 5°. Later more sulf. acid is added and soln. boiled. Black powd., insol. in aq., acids, alk. carbonates, sol. in alk. sulfids and sulf. acid (BBk); siack reducing sulfide vat dyes, fast to soap, light, air, and may be developed by chromate or copper salt. Addition to 641,588. GROUP XV.—SULFUR 253 641,953—Jan. 23, 1900. Arthur G. Green and Alex. Mryenserc, England. Process of making fast brown dyes. 4-TOLUYLENE DIAMIN HCl, 2-PHENYLENE DIAMIN HCl, or other ortho or para diamino ben- zene deriv. in aq. soln. with Na,S,O, to which Na,Cr,O, and H,SO, in excess are added, mix- ture allowed to stand at 20-25°, then more sulfuric and bichromate added and soln. boiled. For product see 641,954. 641,954—Jan. 23, 1900. Arthur G. Green and A. Mryvenserc, England. Fast brown dye. 3-TOLUYLENE DIAMIN HCl, oxidized in aq. soln. by sulfuric and bichromate in presence of Na,S,0,. Brown black powd., insol. in aq., acids, diff. sol. in alk. carb., easily sol in Na,S (Br) and in conc. sulf. (GBk), may be reduced to leuco form and reoxidized; sprown reducing sulfide vat dye, fast to acids, alks., soap, air, light. Near S. 711—‘‘Immedial Orange B.”’ For process pat. see 641,953. 642,256—Jan. 30, 1900. Bernhard Prigss and Oskar Kattwasser, Germany. (Berlin.) Blue sulfur dye. 2.4-Dinitro 4’-oxy DIPHENYLAMIN sulfo, carboxy, or other derivs., heated in sulfur melt by usual process, product refluxed with to parts alc., and residue dried in air. Products after alc. treatment differ from original comps. in physical, chemical and tinctorial properties. Dark brown powd., sol. in aq. (VB), unchanged by NaOH, pptd. by excess NaOH (BBk), aq. soln. pptd. by acids (RV), sol. in conc. sulf. (VB), insol. in alc.; dark BLUE vat dye. Deriv. of S. 724—Immedial Black F. P.” or 737, “Cotton Brown.” 644,959—Mar. 6, 1900. Julius Ase,, Germany. (Badische.) Green-black dye. 2-AMINO PHENOL 4-sulfo acid condensed with 1.2-dinitro 4-chlor BENZENE, to form 2-hydroxy 2'.4’-dinitro DIPHENYLAMIN 5-Sulfo, which is heated with Na,S, sulfur and some water to 160-170°. Product is sol. in aq. (G), pptd. by HCl or NH,Cl (BrBk); green sBiack sulfide vat dye, fast to light, acids, alks., soap, unchanged by after treatment with copper salt or chromate. Near S. 738—‘“Cotton Black.” 645,738—Mar. 20, 1900. Christopher Ris, Switzerland. (Geigy.) Black sulfur dye. Probably 5-mercapto p-imino quinone N-(4”-oxy phenyl) 2-(2’.5’.- dimercapto p-imino quinone). 4-Amino PHENOL, or other para amino deriv., heated in sulfur melt with oxy azo BENZENE or other oxy azo comp. to 200-220°, with or without cGLiycErIN. Black powd., easily sol. in aq. (BGBr), pptd. by acids (Br), turned by bichromate to (Bk), diff. sol. alc., insol. ether and C,H,, sol. in conc. sulf. (dark G); blue siacx reducing sulfide vat dyes, turned deeper and faster black by oxidation by chromates, CuS,, FeCl,, H,0,, etc. 646,873—Apr. 3, 1900. Alcide F. Porrriger, France. Process of making sulfur dyes. PueEno., carefully mixed with 2 parts SO,Cl,, heated to 150-160°, 0.5 part 4-PHENYLENE DIAMIN added and temp. raised to 200°. For use in dyeing, product is melted in Na,S. Other phenols, amines, sulfo acids, or combinations of these are claimed. Black powds., sol. in Na,S, pptd. by acids, salt, and conc. alks.; Back sulfide vat dyes, deeper when oxidized by air, chromates, etc., and giving insol. combinations with metallic oxides. 647,846—Aug. 17, 1900. Richard Kircuorr and Emil Haussmann, Germany. (Berlin.) Black sulfur dye. 2.4-Dinitro 4’-oxy DIPHENYLAMIN and 2.4-dinitro PHENOL in equimolecular mixture, heated in sulfur melt to 140-160° till dry, or soln. of melt may be pptd. by acids. Product is sol. in aq. (GBk), pptd. by salt, acids, also CO, (BrB), pptd. by hot NaOH, (Bk), sol. conc. sulf. (BrG), in fuming sulf. (BBk), pptd. on diln. (GBk); deep BLack sulfide vat dyes. Near S. 725—‘‘Immedial Dark Brown A.” Note 647,847. 254 DIGEST OF PATENTS 647,847—Apr. 17, 1900. Richard Kircuorr and Emil Hausmann, Germany. (Berlin.) Black sulfur dye. 2.4-Dinitro 4’/-oxy DIPHENYLAMINE and PICRAMIC acid or picric acid in equimolecular parts, heated in sulfur melt to 140°. Products sol. in aq. (BBk), pptd. by salt, acids or CO,(GBk), bluer with NaOH, sol in conc. sulf. (B), in fuming sulf. (dark V), pptd. on diln. (dark V), can be reduced to leuco form and reoxidized; deep BLAcK reducing vat dye. Dye is compound one and is not a mixture of two sulfur dyes from components. Addition to 647,846. 648,597—May 1, 1900. Alcide F. Porrrier, France. Process of making sulfur dyes. (Product claimed.) 4-Amino PHENOL and I-NAPHTHOL, or nitroso deriv., heated to 200° with sulfur, then Na,S added and heated to 180-200°. 2-Nitranilin, 1.2-phenylene diamin, 1.3.4- or 1.2.6- triamino benzene, or other amino, azo, nitro aryl derivs. or other amino phenolic comps., may be used. Brown RED, BROWN, or BLACK sulfide vat dyes, fast to alks. 648,753—May 1, 1900. Paul Junius, Germany. (Badische.) Blue-black sulfur dye. 4'.4”-Dioxy 3'.3”-dicarboxy diphenyl 4.6-dinitro 3-PHENYLENE DIAMIN, heated in iron vessel at 140° with 2 parts sulfur, 6 parts cryst. Na,S, and a little aq. until dry. Product is sol. in aq. (BG), pptd. by acids (Br), reduced by alks., (BG); a blue sack sulfide vat dye not changed by after treatment with Cr or Cu, fast to soap, light, and acids. Note 648,754 and 55. 648,754—May 1, 1900. Paul Jutius, Germany. (Badische.) Green-black sulfur dye. 4'-.4”-Dioxy 3'.3”-disulfo diphenyl 4.6-dinitro 3-PHENYLENE DIAMIN, heated in an iron vessel at 140° with 2 parts sulfur, 6 parts Na,5, and a little aq., until dry. Product is sol. in aq. (G), pptd. by HCI (Br), resol. in NaOH (G); a green sBiack sulfide vat dye unchanged by Cr. or Cu. treatment, fast to soap, light, acids. Addition to 648,753. 648,755—May 1, 1900. Paul Junius, Germany. (Badische.) Black sulfur dye. 4’.4”-Dioxy diphenyl 4.6-dinitro 3-PHENYLENE DIAMIN, heated to 140° with 2 parts sulfur, 6 parts Na,S and a little aq. till dry. Product is sol. in aq. (B), pptd. by HCl (Br), resol. in alk. (B); a BLAck sulfide vat dye, unchanged by Cr. or Cu. treatment. Addition to 648,753. 649,218—May 8, 1900. Carl ScuiEussNER, Germany. (Hochst.) Process of making black naphthazarin sulfur dye. (Product claimed.) Intermediate product in mfr. of NAPHTHAZARIN from 1.5 or 1.8-dinitro naphthalene, heated with Na,S and §$, with or without ZnCl, to 150~-180°. Blue gray powd., sol. in aq. or NH,, caustic or alk. carbonate (B), pptd. by acids, diff. sol. in alc.; a BLAcK sulfide vat dye changing from blue to black with Cu on fiber. S. 745—‘‘Melanogen Blue.” Note 561,122 for use of naphthazarin and 667,486 for different method of using 1.5 or 1.8 dinitro naphthalene. h 650,292—May 22, 1900. Julius Apr, and Fritz Katxow, Germany. (Badische.) Brown sulfur dye. 4-Amino PHENOL 2-sulfo, nitrated and condensed with 2.4-dinitro chlor BENZENE to form 4- hydroxy 3-nitro 5-sulfo 2/.4’-dinitro DIPHENYLAMIN which is heated in sulfur melt to 140°. Dark powd. sol. in aq. (VBr), pptd. by acids (Br); dark Brown sulfide vat dye, darkened by Cu treatment. 9 Lal Ab eal aida ca 650,293—May 22, 1900. Julius ABEL and Fritz Ka,xow, Germany. (Badische.) q Black sulfur dye. 4-Amino PHENOL, its sulfo acid or other deriv. condensed with 2.4-dinitro chlor BEN- ZENE, 2 mols., to a tetranitro diphenyl amino phenol ether, then heated in sulfur melt to 140°. GROUP XV.—SULFUR 255 Products are sol. in aq. (BG), pptd. by salt (BG); green siacxk sulfide vat dyes, fast to alks., acids, soap, bluer when treated with bichrom and sulf. acid, then fast to soap, Cl and SO,. Near S. 724.—‘‘Immedial Black.” 650,826—May 22, 1900.° _ Paul Junius and Friedrich Reusotp, Germany. (Badische.) Brown-black sulfur dye. 4.6-Dinitro 1.3-dichlor BENZENE, 2-amino PHENOL HCl and 4-amino pHENor HCl condensed to form 4.6-dinitro 2’-4”-diphenol 3-PHENYLENEDIAMIN, then heated in sulfur melt to 140-160°. Product is sol. in aq. (V), pptd. by HCl (dull V); a brown srack sulfide vat dye, turned browner with bichromate or H,O, treatment. 650,327—May 22, 1900. Paul Juuius and Friedrich Reusoip, Germany. (Badische.) Black sulfur dye. 2.4-Dinitro 5-amino 4’-oxy DIPHENYLAMIN heated in 6 parts Na,S, and 1.67 parts sulfur at 140-150°. Product is sol. in aq. (GB), pptd. by HCl (YBr); deep sBLack sulfide vat dye not changed by Cu, Cr, or H,O,. 651,077—June 5, 1900. Oskar KattwassEr, Germany. (Berlin.) Green-black sulfur dye. 2-Amino 4-chlor PHENOL condensed with 2.4-dinitro chlor BENZENE to form 2.4-dinitro 5/- chlor 2-oxy DIPHENYLAMIN, which is heated in sulfur melt to 140-150°. Product is insol. in alc., sol. in aq. (BG), turning with NaOH (BrV), pptd. from soln. by salt (GBk) by acids or air (BrBk), sol. in conc. sulf. (dull G), on heating, (BkV), sol. fuming sulf. (BkG), pptd. on diln. (BkV), can be reduced to leuco dye and reoxidized; a green BLack sulfide vat dye. Near S. 724—‘“Immedial Black.”” Same components as 724, with chlorine atom in meta position, and hydroxyl group in ortho position, see 610,541. 651,122—June 5, 1900. Carl ScHLEUSSNER, Germany. (Hoéchst.) Naphthazarin sulfur dye and process of making same. NAPHTHAZARIN heated in sulfur melt with ZnCl, to 160-170°. Blue gray powd., easily sol. in aq. (B), diluted soln. (RV), pptd. by acids and resol. in alk. or alk. carbonate (RV-B); red VIOLET to fast deep BLACK when treated with Cu. Addition to 649,218. 653,277—July 10, 1900. Arthur AsHwortH and Joshua Bircer, England. Process of making black sulfur dye. 2-Nitroso NAPHTHOL, or other nitroso phenol or naphthol, condensed with PHENOL in strong sulf. acid, made alk. and heated with sulfur to 180°. Alk. salts of product are sol. in aq., insol. in ether, slightly sol. in hot alc., and the free color acid is insol. in aq. Dye not claimed. Process for 653,278. 653,278—July 10, 1900. Arthur AsHwortH and Joshua Burcer, England. Brown sulfur dye. 4-Nitroso PHENOL, 2-nitrosonaphthol, or other, condensed with PHENOL, then heated with sulfur to 180°. Alk. salts of products are sol. in aq., insol. in ether, slightly sol. hot alc., free color acid is insol. in aq.; green BLACK to BROWN alk. vat dyes, deeper in shade when oxidized. Near S. 717—‘“‘Vidal Black I.” For process see 653,277. 653,670—July 17, 1900. Ernst GorseL, Germany. (Elberfeld.) Olive cotton-dye and process of making same. 2.4-Dinitro chlor BENZENE and monomethyl or unsym. dimethyl diamins, condensed to pro- duce dimethyl 4’-amino 2.4-dinitro DIPHENYLAMIN, and product heated in Na,S and S melt in three stages, 90—-100°, then 150-160°, and finally 280-290°. Dark powds., sol. in aq., in 10 per cent NH, (GBr); green srown sulfide vat dyes. Near S, 728—“Immedial Pure Blue.” 655,659—Aug. 7, 1900. Bernhard Prizss and Oskar Kattwassrer, Germany. (Berlin.) Black sulfur dye. 2.4-Dinitro PHENOL, boiled in aq. with Na,S and S. Black powd., insol. in aq., sol. in Na,S soln. which with NaOH is bluer, pptd. by acids and air, insol. in alc., sol. in hot conc. sulf. 256 DIGEST OF PATENTS (dark B), pptd. on diln. (GBk), may be reduced to leucd form and reoxidized; a BLacK sulfide vat dye. S. 720—‘‘Sulfur Black textra.” Note 618,152, which apparently gives the same product. Process is different but no process claims are made. 656,631—Aug. 28, 1900. Robert Demutu, Germany. (Elberfeld.) Violet cotton-dye and process of making same. Nitroso 1.8-dioxy NAPHTHALENE 2.4-disulfo, or other, reduced to amino oxy compound, then fused with Na,S, S, and ZnCl, at 200-240°. Black powd., largely sol. in aq., in hot NaOH and Na,CO,, in conc. sulf. (RV), pptd. from soln. by acids; blue vioLET sulfide vat dyes, fast to alks. and light. 657,768—Sept. 11, 1900. Hermann GussmMann, Germany. (Héchst.) Blue cotton sulphur dye and process of making same. 4-Nitro chlor BENZENE 2-sulfo condensed with 4-amino PHENOL, reduced to amino comp., fused in alkali to 2.4’-dioxy 4-amino DIPHENYLAMIN, heated in sulfur melt to 160—200°, and finally oxidized. Dark brown powd., of coppery luster, sol. in aq. (B), pptd. by acids as free dye acid which is insol. in aq. but sol. in alks., sol. in conc. sulf. (dull BG), on diln. (B), and pptd.; a BLUE acid mordant dye. Note 657,769. 657,769—Sept. 11, 1900. Hermann GussMann, Germany. (Hochst.) Blue cotton sulphur dye and process of making same. 2.4'-Dioxy 4-amino DIPHENYLAMIN, derived from 4’-oxy 4-amino diphenylamin 2-sulfo by alk. fusion, heated in sulfur melt to 160-180°, dissolved and oxidized by air. Dark powd. of cop- pery luster, soi. in aq. (B), pptd. by acids (B), sol. in conc. sulf. (BG); a BLUE acid mordant dye. Addition to 657,768. 658,055—Sept. 18, 1900. Julius Ape, and Fritz KarKow, Germany. (Badische.) Brown cotton dye and process of making same. (Process not claimed.) 1.4-Dichlor 2.6-dinitro BENZENE obtained by nitrating 1.4-dichlor 2-nitro BENZENE, condensed with 4-amino PHENOL, or other, to form DIPHENYLAMIN deriv., then heated in sulfur melt to 140-150°. Product is BRowN sulfide-vat dye, fast to steam, soap, acids, SO,, and Cl., fastness increased by Cu. 658,286—Sept. 18, 1900. Nikolaus Schwan and Wilhelm ZrpEL, Germany. (Hochst.) Brown sulfur dye and process of making same. 1.3.8-Trinitro NAPHTHALENE, or deriv., is dissolved in aq. soln. of Na,S and S and evap- orated to dryness. Brown black products sol. in aq., pptd. by acids; Brown sulfide vat dyes. Near S. 745—‘“‘Melanogen Blue.” 660,058—Oct. 16, 1900. Meinhard Horrman and Georg KariscHEer, Germany. (Cassella.) Brown sulfur dye. (Process claimed.) 2.4-Dinitro 4’-oxy DIPHENYLAMIN, or other, from 2.4-dinitro chlor BENZENE and 4-amino PHENOL, boiled in alk. soln., then heated with Na,S and §, or other, to 160°. Dark brown powd., sol. in dil. alk., and alk. sulfids, pptd. by acids; deep BRowN sulfide vat dye, fast to washing, acids, oxidizing agents, faster and yellower when chromed. S. 725—“‘Immedial Dark Brown A.’ Note 665,726 for different process applied to sameé material, 660,067—Oct. 16, 1900. Arthur WEINBERG, Germany. (Cassella.) Brown sulfur dye and process of making same. ? s-Amino 2-crESOL, (OH = 1) condensed with 2.4-dinitro chlor BENZENE to form 2.4-dinitro- a phenyl oxy TOLYL amin, nitrated to tetra nitro product, then heated in sulfur melt to 120°. Black lumps or powd., sol. in aq. (dark Br), pptd. by acids; a BROwN sulfide vat dye that may — be diazotized and coupled on fiber, or treated with Cu or chromate to give yellower hue. Near S. 725—‘“‘Immedial Dark Brown A,” part 2. Note 660,058. GROUP XV.—SULFUR ac. 660,770—Oct. 30, 1900. Hermann GussmMann, Germany. (Hochst.) Blue sulfur dye. (Process claimed.) 4’-Amino 4-0Xy DIPHENYLAMIN 3-carbo, from sulfo acid of same, or nitro deriv., heated in sulfur melt to 160-200°. Dark powd. of metallic luster, diff. sol. aq., sol. sulf. (B), converted to leuco comp. on reduction; a BLUE reducing sulfide vat dye. 661,438—Nov. 6, 10900. Rene Boun, Germany. (Badische.) Black dye and process of making same. 1.8-Dinitro NAPHTHALENE dissolved at 130° in 10 to 20 parts 96 per cent sulfuric, H,S passed through or Sb,S, added. The accompanying naphthazarin is removed from pptd. dye by alum soln. If reaction be continued till all naphthazarin is converted, the color is less suited for dyeing. Dye paste is heated at 95° with bisulfite to give soluble comp. Product is diff. sol. in aq. (dull BV), sol. in fuming and conc. sulf. (23 per cent SO,) (dull RV); fast Biacx acid mordant dye, adapted to printing. ; S. 740—“Fast Black B.’ Patent claims product “Superior to that obtained with naphth- azarin.” 661,907—Nov. 13, 1900. Karl Exper and Ignaz Rosenperc, Germany. (Kalle.) Brown sulfur dye and process of making same. 2.4-Dinitro chlor BENZENE condensed with PyRIDIN by heating to 70-80° in aq. (or by heat- ing dry then dissolving in water). Soln. is made alk., warmed to 80-90°, and separated ppt. heated in sulfur melt to 120-280°. Product is sol. in aq. (YBr), less’sol. in alc. (GY), sol. in conc. sulf. (YBr), pptd. from aq. soln. by HCl or salt (Br); a yellow BrRowwn sulfide vat dye, fast to washing, acid, alk., and light. 665,547—Jan. 8, 1001. Alcide F. Porrrier, France. Black substantive sulfur dye and process of making same. 4-PHENYLENE DIAMIN, or 4-amino phenol, oxidized with 1-NAPHTHOL, or other aryl oxy comp., to form INDOPHENOLS, or indoanilines, not indamins, (must contain at least one OH group) then fused at 200° with sulfur, Na,S added and again heated to 200°. Products are sol. in aq., and are BLACK sulfide vat dyes, improved by oxidation on fiber with bichromate. S. 730—‘‘Pyrogen Black.”’ 665,726—Jan. 8, 1901. Albert BertscHMANN, Switzerland. (Basle.) Sulfurized indophenol dye and process of making same. 2.4-Dinitro 4/-oxy DIPHENYLAMIN indophenols, or other para oxy derivs., and sodium tetra- sulfide in alc. soln., heated to 145° with or without NH, NaOH, anilin, sulfanilic acid, or other amin. ‘Two dyes are formed for which a method of separation is given. Main product is a deep blue cryst. powd., with coppery luster, sol. in alk. sulfide (VB); violet spLuE to dark BLUE sulfide vat dyes, becoming more violet on treatment with oxidizing agent. S. 726—‘“‘Pyrogen Direct Blue.” Note 610,541 for other part of product, and 660,058 for use of same material by different process. 667,486—Feb. 5, 1001. Rene Boun, Germany. (Badische.) Blue sulfur dye and process of making same. 1.5-Dinitro NAPHTHALENE dissolved in 20 parts 96 per cent sulf. acid at 130° through which H,S is passed for 8-10 hours. Or H,S may be passed into a NAPHTHAZARIN melt at 130°. A blue black powd., sol. in hot aq. (GB), not changed by NaOH, or Na,CO,, sol. in dil. NaOH (GB), in conc. sulf. (Br), in C,H,NO, (BV), reduced with SnCl, and HCl gives brown yellow leuco dye; a BLUE sulfide vat or GREEN acid mordant (Cr) dye. : Possibly S. 745—‘“‘Melanogen Blue.” Note 649,218 for different process using same material. 667,689—Feb. 12, 1901. Karl Evze, and Ignaz RosENBERG, Germany. (Kalle.) Process of making black substantive sulfur dye. Dinitro 2-chlor BENzoIc acid and 4-amino PHENOL, or other chlor ortho carboxy derivs., con- densed to form 4-oxy dinitro DIPHENYLAMIN 2-carbo, the carbo group being in ortho position to imino or hydroxy group, then heated in sulfur melt to 140-150°. Black powds., sol. in aq. (GBk), diff. sol. alc. (GB), changed to (BBk) by NaOH, soln. pptd. by HCl (Bk), sol. conc. sulf. (GB), pptd. on diln. (Bk); fast BLack alk. sulfide vat dye, made faster by treating with metallic salts. S. 724—“‘Immedial Black” carbo acid. 258 DIGEST OF PATENTS 671,908—Aug. 9, 1901. Hermann GussMANN, Germany. (H6chst.) Black sulfur dye. (Process claimed.) 4-Nitro chlor BENZENE 2-sulfo and 4-amino crESOoL condensed to 4-oxy 3-methyl 4’-amino 2/-sulfo DIPHENYLAMIN, then reduced and heated in sulfur melt to 180—240.° Dark porous mass, sol. in aq. (GBr), turning with air to (VB-GB); a sBiack sulfide vat dye. 673,388—May 7, 1901. Robert DemutH, Germany. (Elberfeld.) Blue cotton dye and process of making same. I-AMINO 8-NAPHTHOL 2.4-disulfo, mono sulfo or other disulfo derivs. in alk. soln. with zinc, ZnCl,, or other zinc comp., heated in sulfur melt to 200-240°. Black powds., sol. in aq. (B), in hot NaOH or NH,OH (B), in conc. sulf. (dull VR), pptd. from soln. by acids; Brug sulfide vat dyes fast to alks. and light. Note 614,538. 674,137—May 14, 1901. Gustav Linx, Germany. (Hochst.) Brown dye and process of making same. 1.8-Dinitro NAPHTHALENE heated in Na,S to 160-180°. A brown mass, sol. in aq. (dark Br), pptd. by acids, sol. in NaOH, alk. carb., NH,OH and alk. sulfids; a Brown sulfide vat dye. Near S. 743—‘‘Kryogen Brown A.” Note 609,327 and 632,170 for similar process and material. 675,585—June 4, 1901. Melchior B6nicER, Switzerland. (Sandoz.) Black sulfur dye and process of making same. 1-Chlor 4.8-dinitro NAPHTHALENE or other mono or dinitro or nitro sulfo deriv., condensed with 4-amino PHENOL, or same with sulfo deriv. in ortho position to OH, to form 4’-oxy phenyl 4.8-dinitro I-NAPHTHYLAMIN which is heated in sulfur melt to 130-135°. Black powds., sol. in alk. sulfids (Bk), in conc. sulf. (BBk); blue BLacK sulfide vat dye, changed by oxidizing agents to dark BLUE (CrO,), fast to alks., acids. A nitro group in the benzene nucleus would change color from black to brown. 679,199—July 23, 1901. Re. 11,973—Mar. 4, 1902. Julius AsgeLt, Germany. (Badische.) Blue sulfur dye and process of making same. Dimethyl 4-PHENYLENE DIAMIN thio sulfo or analogous comps., and PHENOL or derivs., con- densed by oxidation with bichromate in acetic soln. to form dimethyl amino INDOPHENOL thio sulfo which is heated to 125° in sulfur melt. Products are insol. in aq., HCl or Na,CO,, may be reduced to leuco form; BLUE reducing sulfide vat dyes. S. 729—“‘Kryogen Pure Blue R.” Note 1,083,110 for further use of product. 681,689—Sept. 3, 1901. Wilhelm Epstein and Emil RosEnrtHAL, Germany. Brown sulfur dye and process of making same. BENZIDIN or derivs. nitrated to dinitro deriv., heated in sulfur melt at 260-265°. Product is sol. in aq., pptd. by acids; yellow Brown to brown BLACK reducing sulfide vat dye, fast to soap, acids, alks., deepened on fiber by oxidation with Cu, CrO,, etc. This compound-2.2’-dinitro-4.4’/-diamino diphenyl is termed in patent the meta dinitro deriv. of benzidin, counting from amino groups as 1.1’; not from common bond between phenyl groups. 687,072—Nov. 19, 1901. Max Scuumann, Germany. (Badische.) Brown sulfur dye and process of making same. ACETANILID, nitrated to 2.4-dinitro acetanilid and heated in sulfur melt to 200—-240°. Prod- uct is sol. in aq. (Br), pptd. by acid (Br), sol. in conc. sulf. (Br), in alc. (Y); a BRowN sulfide vat dye, slightly yellower when chromed, fast to washing, acids, light. Near S. 715—‘‘Thiocatechine.” 687,581—Nov. 26, 1901. Heinrich Srrpet, Austria Hungary. (Kalle.) Brown sulfur dye. Waste LYE from sulfite cellulose process, neut., conc., freed from Ca or not, and heated in sulfur melt to 120-180°. Black powd., sol. in aq., or conc. sulf. (Br), pptd. on diln. (Br), pptd. from soln. by acids, not changed by alks, insol. in alc.; a Brown sulfide vat dye the fast- ness of which is increased by after treatment with Cr, Cu or Fe salts. S. 708—‘‘Sulfanilin Brown 4-B.” GROUP XV.—SULFUR 259 688,646—Dec. 10, 1901. Paul Jutius, Germany. (Badische.) Black sulfur dye and process of producing same. 3.5-Dinitro 1,2.4-trichlor BENZENE condensed with 2 mols. 4-amino PHENOL to form 2.4-di- nitro 6-chlor 4’.4”-dihydroxy diphenyl 3-PHENYLENEDIAMIN by warming in alc. soln. in presence of sod. acetate then heated in sulfur melt to 140-180°. Product is sol. in dil. NaOH (V), slightly sol. in conc. sulf. (G), aq. soln. with Na,O, (dull RV); Biack sulfide vat dye, greener when chromed. (CrO,). Note 648,755, which is same product without halogen. 688,885—Dec. 17, 1901. C. Ris, Switzerland. (Geigy.) Brown sulfur dye and process of making same. 3-TOLUYLENE DIAMIN, 2 mols., and 1 mol. PHTHALIC anhyd., are melted together at 120-200° till aq. ceases to evolve, then heated in sulfur melt at 270-300.° Other diamins or nitro comps. which produce diamins upon reduction and other dicarboxylic acids may be used. Dark powds., sol. in aq. (OBr), in conc. sulf. (Y-OBr), in alc. (Y-O), pptd. from soln. by acids (Br), sol. in alk. carbonates (OBr), can be reduced to leuco form, insol. in ether and C,H,; orange BROWN reducing sulfide vat dye, oxidized on fiber to yellow Brown, fast to light, alks., acids and soap. 688,999—Dec. 17, 1901. Bernard Hrymann, Germany. (Elberfeld.) Process of dyeing on the fiber. Producing new dyes by alkylation or alphylation of sulfur dyes on fiber. Fiber dyed with 10 per cent sulfur dye obtained from 2.4-dinitro 4/-oxy DIPHENYLAMIN as in 610,541, is rinsed and passed a) into bath containing 5 per cent PHENYL dimethyl ammonium chloride and 10 per cent NaOH (40°) at 80° or b) bath of 3 per cent chlor ACETAMID at 90°, with addition of 2 per cent cryst. Na,S. Other sulfur dyes and other alkyl or alphylating agents are claimed. Products are fast green BLUE or violet BLUE developed dyes. 690,271—Dec. 31, 1901. Richd, O. Fr. Hatter, Germany. (Badische.) Brown sulfur dye and process of making same. sym-Hexa nitro DIPHENYLAMIN added to 5 parts Na,S at 45-50°, then 2 parts sulfur added and melt heated to 140°. Product is sol. in aq. (Br), pptd. by NH,Cl (Br), sol. in conc. sulf. (YBr); a Brown sulfide vat dye, deepened by chrome alum, and can be developed on fiber by diazo comps. or diazotized and developed with 2-naphthol, etc. 692,174—Jan. 28, 1902. Julius Aspet and Fritz Kautxow, Germany. (Badische.) Black sulfur dye and process of making same. 4’-Hydroxy 2.4-dinitro DIPHENYLAMIN, heated with copper sulfate, or other salt, in sulfur melt to 220°. Product is almost insol. in alc.; a deep siack sulfide vat dye, less green with CuSO,, dull blue Brack, not blue, with H,O,, fast to washing without after treatment with chromate. 7 Near 724—“Immedial Black.’’ Note 610,541, etc., for similar process without use of copper or its salts. 693,632—Feb. 18, 1902.’ Arthur WEINBERG and Richard Herz, Germany. (Cassella.) Blue sulfur dye and process of making same. Dimethyl 4-amino 4’-oxy DIPHENYLAMIN, is heated in sulfur melt to 115°, dissolved, pptd. by acids, redissolved and oxidized. Dark blue bronzy powds., sol. conc. sulf. (B), in caustic or alk. sulfids; a BLUE sulfide vat dye, fast to light, acids, washing and chlorine. S. 728—“Immedial Pure Blue.” Note 693,633 for salt of above dye with Ca, etc. 693,633—Feb. 18, 1902. Arthur WEINBERG and Richard Herz, Germany. (Cassella.) Process of making blue sulfur dye. Purifying dye of 693,632. Dialkyl 4-amino 4/oxy-DIPHENYLAMIN, is treated as in 693,632 at temp. below 140°, dye pptd. with CaCL, salt, or other metal giving soluble sulfid, filt., washed, redissolved in Na,S and Na,CO,, filt. and pptd. by NaCl. Impurities and, accompanying black dyes are thus removed and pure BLUE dye remains. S. 728—“Immedial Pure Blue.” 260 DIGEST OF PATENTS 695,533—Mar. 18, 1902. Anton Bonati, Germany. (Kalle.) Sulfur dye and process of making same. 4-Nitro 2-amino 4'-oxy DIPHENYLAMIN from dinitro comp., in alc. soln., heated with carbon bisulfide to form thio carbamid, then fused in sulfur melt at 110-145°. Product is sol. in aq. (GB), changing with Na,S to (B) and on boiling (Gt); a gray GREEN sulfide vat dye developed to green BLUE by H,O, and metallic salts, such as SnCl,. S. 736—‘‘Thionin Blue B.” Note 695,534 for process of purification, 695,534—Mar. 18, 1902. Anton Bonati, Germany. (Kalle.) Sulfur dye and process of making same. Air is passed through the aqueous soln. of crude melt of 695,533, while salt is added in portions till all dye is pptd. Product is sol. in aq. (GB), turning with Na,S to (B) and on boiling to (pale Y-G); green BLUE sulfide vat dye, brighter and more violet with H,O, and SnCl,. 695,835—Mar. 18, 1902. Friedrich Reuspotp, Germany. (Badische.) Black sulfur dye and process of making same. Dinitro m-dichlor BENZENE nitrated to tri comp. then boiled in alc. soln. with 4-amino PHENOL HCl and sod. acetate to form 4’.4”-hydroxy diphenyl 2.4.6-trinitro 3-PHENYLENE DIAMIN, which is heated in sulfur melt to 160-180°. Black substance, sol. in aq. (G), which with Na,S is bluer, sol. in conc. sulf. (dull G); green BLack sulfide vat dye, made bluer by H,O, and NH,OH. Near S. 724—‘‘Immedial Black.”’ 696,751—Apr. 1, 1902. C. Ris, Switzerland. (Geigy.) Blue sulfur dye and process of making same. The INDOPHENOL or dimethyl 4-amino phenyl quinone imid, obtained by oxidation of as- dimethyl 4-PHENYLENEDIAMIN and PHENOL with hypochlorite, reduced and sulfonated with sul- fite, pptd. by acid and heated in sulfur melt at 120-130°, then oxidized. Blue paste or powd. almost insol. in aq. and Na,CO,, sol. in hot NaOH (B), diff. sol. alc., insol. ether and C,H,, sol. in conc. sulf. (Br), insol. dil. acids, sol. in Na,S (B), in excess (GyV), with oxygen (B); fast BLUE reducing sulfide vat dyes. Note 698,555 for use of copper and its salt in melt. 698,220—Apr. 22, 1902. Anton PFENNIGER, Switzerland. (Brugg.) Greenish-black sulfur dye and method of making same. ToLUENE 4-Sulfo heated in Na,S melt to 130-250°, sulfur added and further heated at 280-300°. Green BLAcK sulfide vat dye, fast to light. 698,555—Apr. 29, 1902. C. Ris, Switzerland. (Geigy.) Green sulfur dye and process of making same. , Sulfo acid of dimethyl 4-amino 4/-oxy DIPHENYLAMIN (indophenol, from dimethyl 4-PHENYL- ENEDIAMIN and PHENOL treated with sulfites) heated to 125-130° in sulfur melt with copper or its salts. Dark powd., sol. in aq. (V), diff. sol. in alc., insol. ether and C,H,, aq. soln. pptd. by acids, (Br), insol. NH,OH and Na,CO,, sol. conc. sulf. (Br-GyV); GREEN sulfide vat dye, fast to soap and light. Addition to 696,751. 701,051—May 27, 1902. Werner Ketspe, Germany. (Héchst.) Black sulfur dye and process of making same. ; Chlor nitro PHENOL sulfo or 2.6-dichlor 4-nitrophenol or other derivs. in which the NO, is in ortho position to halogen or takes place of sulfo group, heated in sulfur melt to 160-190°. Deep black powd., insol. in aq., and alk. carbonates, partly sol. in caustic, sol. in alk. sulfids; green BLACK sulfide vat dyes, becoming deep black with copper salts. 701,435—June 3, -1902. Arthur WEINBERG, Germany. (Cassella.) Brown-violet sulfur dye and process of making same. 2.4-Dinitro chlor BENZENE and 4-amino sALicyLic acid, condensed to form 2-amino 7-oxy PHENAZIN, its sulfo, halogen or carboxy deriv., then heated in sulfur melt to 140-150°. Dark violet or black powd., sol. conc. sulf. (VBk), pptd. on diln., sol. in alk. sulfids; brown vioLET sulfide vat dyes, fast to washing, alks., acids, and light. S. 739—‘‘Immedial Bordeaux G.” . Note 866,939 for similar process, also 818,980. Sanne ee ne ee eee GROUP XV.—SULFUR 261 706,969—Aug. 12, 1902. Ivan Levinste1In and Carl MENnscuinc, England. Black sulfur dye and process of making same. 4-NITRANILIN, 2 mols., coupled with PHENOL and resulting disazo dye refluxed in aq. soln. of Na,S and S. Mixed disazo dyes using one mol. nitranilin and another diazo body claimed. Equimol. of 4-oxy dinitro DIPHENYLAMIN added to above melt give bluer blacks. Copper sulfate, etc., assists reaction. Products are insol. in alc. and conc. sulf., sol. in NaOH and Na,S, (GB); green BLACK sulfide vat dyes, fast to washing, light. 702,369—June 10, 1902. Ivan LkEviInsTEIN and Carl MENscuING, England. (Levinstein.) Black sulfur dye and process of making same. Dinitro PHENOL, trinitro phenol, picramic acid, or other nitro or amino derivs., heated with OXY azO BENZENE in soln. of sulfur in Na,S at boiling temp. or above, with or without zinc or other metal, pptd. by acids, bicarb., salt, or current of air. By mixtures in different propor- tions black dyes varying from red to violet to green black are obtained. (See table of pro- portions for various shades.) Black powds., insol. in aq., alc., sol. in conc. sulf., pptd. on diln., sol. in alk. sulfids; a red to green sLacx sulfide vat dye. Note 655,659. 708,662—Sept. 9, 1902. Alcide F. Porrriger, France. (St. Denis.) Blue sulfur dye and process of making same. INDOPHENOL derived by oxidation of equimols of 4-PHENYLENE DIAMIN and PHENOL or cresol, is heated in aq. Na,S and S$ to 120-130°, and to this is added the product of reaction of 2 mols. sulfur chloride on 1 mol. PHENOL and temp. raised to 150-160° till dry. Black powds., sol. in aq. (B), pptd. by acids, ppt. sol. in Na,CO,, and alk. sulfide; fast BLUE sulfide vat dyes. Near S. 735—‘‘Pyrogen Indigo.” Addition to 646,873. 709,151—Sept. 16, 1902. Richard Herz, Germany. (Héchst.) Blue sulfur dye and process of making same. 4-Amino tolyl 4’-oxy DIPHENYLAMIN, is heated in sulfur melt at 80° then at 120°. By modifying conditions, temp., etc., the shade of color is varied,—high temp. more green, lower temps. more red. Dark blue powd., sol. in aq. containing caustic or alk. sulfids, (dull RV), sol. conc. sulf. (B); piu sulfide vat dye fast to acids, light, and milling. S. 733—‘“‘Immedial Indones.” Note 742,089. 710,766—Oct. 7, 1902. Walter DotuFus, Germany. (Hochst.) Blue sulfur dye and process of making same. 4-Amino 4’-oxy DIPHENYLAMIN heated in sulfur melt to 120°, pptd. by acid, washed, and oxidized in alk. soln. by air. Blue black bronzy powd., somewhat sol. in usual solvents; a “BLUE sulfide vat dye, fast when coppered. Near S. 728—‘“‘Immedial Pure Blue.” 711,038—Oct. 14, 1902. Edward Cuumann, New York. (Schoellkopf.) Dark sulfur dye and method of making same. ' Dinitro saLicyLic acid heated in sulfur melt to 150-180° or boiled in soln. with sulfur and Na,S. If condensing agent such as ZnCl, is added to melt, dyes are bluer black. Product, which may be purified by usual methods for sulfur dyes, is blue black solid, sol. in caustic or alk. sulfids (BG), in conc. sulf. (dark V); deep siacx sulfide vat dye. 712,176—Oct. 28, 1902. Melchior BonicEer, Switzerland. (Sandoz.) Brown sulfur dye and process of making same. I.2-NAPHTHOQUINONE 4-sulfo, condensed with suLFANILIC acid to form 2-oxy 1.4-NAPHTHO- QUINONE 4/-sulfo phenyl 4-imid, which is heated in sulfur melt to 200-280°. Similar dyestuffs from related compounds are claimed. Dark brown powds., sol. in aq. (Br), unchanged by alks., pptd. by acids or BaCl,, insol. C,H, or C,H,CH,, diff. sol. boiling alc. (Br); Brown sulfide vat dyes. S. 747—‘“Thional Brown G.” 712,747—Nov. 4, 1902. Arthur Wernsperc and Otto Lance, Germany. (Cassella.) Yellow sulfur dye and process of making same. 3-TOLUYLENE DIAMIN melted in iron pot. in 2 parts sulfur, then temp. raised to 190° (not, exceeding 220°) to render soluble, and heated not above 150° with caustic alkali or Na,S. 262 DIGEST OF PATENTS Water must be present. Products are sol. in dil. NaOH or Na,S, almost insol. in conc. sulf.; YELLOW sulfide vat dyes, fast to washing, milling and acids. S. 710o—‘‘Immedial Yellow D.” %714,542—Nov. 25, 1902. Arthur WerINBERG and Otto Lancer, Germany. (Cassella.) Orange-brown sulfur dye and process of making same. 3-TOLUYLENE DIAMIN fused with sulfur at 250°, then after addition of Na,S, heated at 110—120° to render soluble. Product is sol. in dil. alk. sulfids (OBr), pptd. by acids (Br), almost insol. conc. sulf.; orange BRowN sulfide vat dye, fast to washing, milling, acids. S. 7x11—‘‘Immedial Orange N.” Note 712,747 and 895,637 for similar processes. 718,342—Jan. 13, 1903. Louis Haas, Germany. (Badische.) Sulfurized cotton-dye and process of making same. Dinitro BENZYL sulfo or mono nitro deriv., in aq. sulfur melt, heated to 150-200° then at 220° to 240°. Other nitro sulfo components claimed. 4-NITROBENZENE sulfo gives yellow dye and dinitro deriv. a brown. Products are not easily sol. in 10 per cent Na,CO, or 50 per cent Na,S; BROWN to YELLOW sulfide vat dyes, fast to chroming and can be diazotized and coupled with 2-NAPHTHOL, etc., on fiber to give redder shades. 722,6230—March 10, 1903. C. Ris and A. Myuius, Switzerland. (Geigy.) Yellow sulfur dye and process of making same, 3-TOLUYLENE DIAMIN and FORMALIN, condensed to mono or di-formyl deriv., then with or without BENZIDIN, 3-toluylene diamin, or other diamins, heated in sulfur melt. Light brown powds., sol. on hot dil. NaOH or Na,S, (Y), insol. in alc., ether, C,H,, sol. in conc. sulf. (Y, milky); yvELLow sulfide vat dyes. 723,154—Mar. 17, 1903. Richard Herz, Germany. (Cassella.) Blue sulfur dye and process of making same. 4-Amino DIPHENYLAMIN and PHENOL oxidized in acetic soln. with bichromate, then heated in alk. soln. with Na,S to form phenyl 4-amino 4’-oxy DIPHENYLAMIN which is boiled in alc. soln. with sod. pentasulfid, then oxidized. Or dye may be formed in sulfur melt at 140—-150° by usual method. Dark blue powd., sol. in alk. sulfids (GB), in conc. sulf. (B); an indigo BLUE sulfide vat dye, fast to washing, acids and light. S. 735—‘‘Pyrogen Indigo.” 723,448—Mar. 24, 1903. Hans Esetine, Germany. (Kalle.) Brown sulfur dye and process of making same. Amino derivatives of 3-TOLUYLENE DIAMIN or diazo deriv. of same, heated in sulfur melt to r10-120°, then to 200-2209. When azo deriv. is used, anilin splits off in first part of re- action. Products are sol. in aq., pptd. by acids, sol. in conc. sulf., insol. in alc.; red BROWN sulfide vat dyes, fast to soap and light, and can be diazotized on the fiber, and coupled with 2-naphthol, 3-toluylene-diamin, or resorcin. 727,387—May 5, 1903. Emil Kraus, Switzerland. (Basle.) Blue sulfur dye and process of making same. 4-Nitroso PHENOL, or homolog, combined at 20-25° with DIPHENYLAMIN, or other alkyl- ated aromatic amin, in strong sulf. acid, then treated with alk. Na,S to form phenyl 4-amino 4’-oxy diphenylamin derivs. or homolog, which is heated a) in alc. soln. containing Na,S, in autoclave to 150-160° or b) with Na,S without alc. in aq. suspension, with or without glycerin or metallic salts. Blue powds., sol. in aq. and alk. sulfids; BLUE sulfide vat dyes, fast to acids, milling, light. Near S. 728—‘‘Immedial Pure Blue.”’ 728,623—May 19, 1903. Albrecht Scumipt and Fritz BetuHmann, Germany. (Ho6chst.) Blue sulfur dye and process of making same. as-Dimethyl 4-PHENYLENE DIAMIN, or other, condensed by oxidation with 2.6-dichlor PHENOL to form an indophenol which is reduced by Na,S to dimethyl 4’-amino 4-oxy 3.5-dichlor p1- PHENYLAMIN, which is heated at 94° in Na,S-S mixture with Giycerin and alcohol. Blue black powds., sol. in conc. sulf. (B), diff. sol. in alc.; snug sulfide vat dyes, bluer or more violet with air or oxidizing agents. GROUP XV.—SULFUR 263 729,874—June 2, 1903. August L. Lasxka, Germany. (Oehler.) Olive-green sulfur dye and process of making same, Di-formyl 3-PHENYLENE DIAMIN, heated in sulfur melt containing ZnCl, to 110-275°. Color is not so bright without ZnCl,. Black brittle mass or powd., sol. in conc. sulf. (dull G), in aq. (GY), pptd. by HCl (YBr), sol. in dil. NaOH or NH,OH; brown GREEN sulfide vat dye, fast to light and soap. 731,669—June 23, 1903. Edward Curmann, New York. (Schoellkopf.) Green sulfur dye and process of making same. Amino azo BENZENE (or toluene) HCl and 4-amino PHENOL condensed by heating together at 180° then refluxed with Na,S-S soln. containing some copper sulfate, at 102-105°. Product is sol. in conc. sulf. (BBk), almost insol. in aq. Na,CO,; GREEN sulfide vat dye. 732,090—June 30, 1903. Ivan and Herbert LkEvinstEIN, England. (Levinstein.) Blue sulfur dye and process of making same. Ethyl 2-tToLuipIN or homolog and 2-chlor 4-amino PHENOL in sulfuric acid soln. oxidized with bichromate to indophenol then reduced with Na,S to ethyl 4-amino 3-methyl 4’-hydroxy 3/-chlor DIPHENYLAMIN, which is heated in sulfur melt to 115°, and pptd. by current of air. Blue substances, sol. in conc. sulf. (B), in NaOH (RV); BLUE sulfide vat dyes, fast to washing and light. 735,775—Aug. 11, 1903. . Paul Juuius and Friedrich Reusoitp, Germany. (Badische.) Substantive sulfur dye. (Process claimed.) 1.3-Dinitro 4.6-dichlor BENZENE, condensed in acetone or alc. soln. with KCNS or other thionizing agent, to form 1.3-dinitro 4.6-dithiocyan BENZENE, which is separated, purified, and with 4-amino PHENOL or derivs. and sod. acetate is heated in alc. to 65° to form 2.4-dinitro 5-thiocyan 4’/-oxy DIPHENYLAMIN, Separated product is heated in sulfur melt to 90° then 160—- 180°. Product is black substance, insol. in common solvents; BLUE reducing sulfide vat dye, oxidized by air, fast to washing, alks., acids. 736,380—Aug. 18, 1903. Richard Guiry, Germany. (Berlin.) Blue sulfur dye and process of making same. 4.4’-Dioxy DIPHENYLAMIN is fused with sulfur at 230-240°. A blue black powd., insol. in aq., sol. in caustic (B), in alk. sulfid (GB), in conc. sulf. (B); fast BLUE sulfide vat dye. . .736,403—Aug. 18, 1903. Oskar KaLtwassER and Max GaumeEr, Germany. (Berlin.) Indigo-blue sulfur dye and process of making same. INDOPHENOL, or homolog, is boiled in sulfur mixture containing at least 4 atoms of sulfur to 1 mol. Na,S and dye pptd. by oxidation with air. Products are insol. in aq., sol. in caustic alk. (dull GB), in alk. sulfids (B), in conc. sulf. (V); fast BLUE reducing sulfide vat dyes, after oxidation on fiber. Near S. 731—‘‘Thiophor Indigo.” Note 821,378 for similar patent. 738,027—Sept. 1, 1903. Richard Giry, Germany. (Berlin.) Yellow sulfur dye and process of making same. Nitro diacetyl] 4-PHENYLENE DIAMIN, the meta or ortho comp. or homolog, and equal weight | BENZIDIN or other heavy volatile amin, is heated in sulfur at 230-240°. Yellow brown powds., sol. in conc. sulf. (Br), in Na,S (Y); yELLow sulfide vat dyes, fast to washing and light, fast- ness increased by coppering or chroming. Near S. 715—‘‘Thiocatechine.” 740,465—Oct. 6, 1903. Alcide F. PorrriEr, France. (St. Denis.) Substantive black dye and process of making same. PHENOL, cresol, anilin, etc., mixed with sulfur chloride is heated to 150-165°, and product, together with substituted diphenylamins such as 4-amino 2-nitro 4/-oxy DIPHENYLAMIN, heated to 170° then 200° after Na,S has been added. The ratio of NH, to OH in the substituted di- phenylamin must be less than 2:1. Products are sol. in aq.; blue Brack sulfide vat dyes, not affected by bichromate, etc. Note 646,873. 204 DIGEST OF PATENTS 741,030—Oct. 13, 1903. Richard Guiry, Germany. (Badische.) Green sulfur dye and process of making same. I-NAPHTHYLAMIN or sulfo derivs. and 4-amino PHENOL, homologs or halogen derivs., is oxidized to an INDOPHENOL which is boiled in sulfur and Na,S mixture containing copper sulfate, diluted and pptd. by current ot air. Dark green powds., insol. in aq., sol. in alk. sulfids (G), slightly sol. in conc. sulf. (B), in caustic alks. (G); GREEN sulfide vat dyes. " 742,189—Oct. 27, 1903. Richard Herz, Germany. (Cassella.) Blue sulfur dye and process of making same. 4-Amino 3-methyl 4’-oxy 3’-chlor DIPHENYLAMIN is added to sulfur melt at 80-100° then temp. raised to 115°, diluted, filtered, and pptd. by current of air. Lower temps. give redder and higher temps. greener shades. Dark blue powd., nearly insol. in aq. or alc., sol. conc. sulf. (B), sol. in alk. sulfids; green BLUE sulfide vat dye, fast to washing, acids and light. Addition to 709,151. 746,926—Dec. 15, 1903. Edward Cuumann, New York. (Schoellkopf.) Orange to yellow brown sulfur dyes and process of making same. TOLUYLENEDIAMIN sulfo (2.6.4 or 2.4.5), the unreduced nitro or oxamin comp., is heated in shallow vessel at 120-130° with soda, sulfur and Na,S, then baked at 250°. Dark brown powds., sol. in aq., pptd. by acids (Br), sol. in conc. sulf. (YBr-RBr);oRANcE to yellow BROWN sulfide vat dyes that may be diazotized and coupled on fiber to deepen shade. Addition to 659,496 and 97. 747,643—Dec. 22, 1903. Niklaus Ronecer, Switzerland. (Sandoz.) Blue sulfur dyestuff and process of making same. 4-Amino 3-methyl 4’-oxy DIPHENYLAMIN is heated with sulfur and a little chromium hydroxid (Cr,O,.H,O) at 190-200° till H,S ceases to evolve and melt becomes thick. Without Cr the shade is duller and greener. Dark blue powd., insol. in aq. and alc., sol. in alk. sulfids (B), changed on boiling to (Br), sol. in conc. sulf. (B); BLUE sulfide vat dye, fast to alks., washing, light. Addition to 709,151. 750,113—Jan. 19, 1904. Arthur LurrrincHaAus, Germany. (Badische.) Green dye. METHYLENE VIOLET, the acetyl deriv. or dye of 678,199, Re. 11973, is refluxed in 3 parts Na,S, 1.5 parts CS, and 9 parts ale. CS, may be omitted and more alc. (14 parts) used. Prod- ucts are sol. in dil. Na,S; creEn sulfide vat dyes changing to BLUE with bichromate. 755,428—Mar. 22, 1904. Julius Apet and Arthur Lutrrincuaus, Germany. (Badische.) Blue-sulfur dye and process of making same. METHYLENE VIOLET or alkylated indophenol in 4 parts cryst. Na,S heated to 136° and to this is added about 1.5 parts PHENOL and 1 part S, temp. raised to 142°, refluxed, then diluted with aq., and oxidized by air. Product is sol. in caustic (B), not pptd. by air, pptd. by CO,; a BLUE sulfide vat dye. 760,110—May 17, 1904. Wilhelm EmmMericu, Germany. (Hochst.) Orange sulfur dye. ToLUYLENE di-urea (from 3-TOLUYLENE DIAMIN and KCNO) is added to 3 parts fused sulfur at 170-180° then heated to 220-230°. Dark red brown powd,, sol. hot NaOH and Na,S (Br); ORANGE sulfide vat dye, fast to light, soap, carbonate and acids. 763,193—June 21, 1904. Ernst Matus, Germany. (Hochst.) Blue sulfur dye and process of making same. sym-4”.4'"'"-Dioxy diphenyl 4.4’-diamino DIPHENYLAMIN, 3 parts, is refluxed with 8 parts Na,S, 3.4 parts sulfur, and 4 parts GLYCERIN at 100 to 110°. Dark blue powd., insol. in usual solvents, sol. dil. alk. (B), in conc. sulf. and in alk. sulfide (G); BLUE sulfide vat dye. 763,320—June 21, 1904. Alcide F. Porrrier, France. (St. Denis.) Process of making sulfur dyes. Dimethyl INDOPHENOL, or derivs. obtained by oxidizing dimethyl 4-PHENYLENE DIAMIN and PHENOL, is reduced in hot aq. with Na,S, dried to paste and at 120-130° equal part of product GROUP XV.—SULFUR 265 of reaction of sulfur chloride on comm’! cresox, or other phenol, is added, then further heated at 130-160°. Table of reactions is given. Product is sol. in aq., and is a BLUE sulfide vat dye. 764,733—July 12, 1904. Richard Laucu, Germany. Black sulfur dye and process of making same. 4-PHENYLENE DIAMIN is condensed with 2.4-dinitro chlor BENZENE to form 4’-amino 2.4-dinitro DIPHENYLAMIN, which is heated in sulfur melt with water and glycerin to 175-180°. Using more glycerin, a lower temp. and longer heating are required, and without glycerin a higher temp. and several additions of solvent. Series of: reactions is given. Product is a piacK sulfide vat dye, faster when chromed or coppered. S. 727—‘“‘Auronal Black.’ Note 764,734 for different process using same ingredients, and 764,735 for subsequent oxidation process. 764,734—July 12, 1904. Richard Laucu, Germany. Direct cotton sulfur dye and process of making same. 4-PHENYLENE DIAMIN is condensed with 2.4-dinitro chlor BENZENE to form 4’-amino 2.4-dinitro diphenylamin which is boiled in Na,S and S mixture containing water and preferably also some glycerin, at 115-125°. Longer heating at 120-130° gives black dye and fastness to washing in- creases with time of heating. Violet black powd., sol. conc. sulf. (V-B), pptd. on diln. (B), sol. dil. Na,S(V); violet BLUE to BLACK sulfide vat dyes. . S. 727—‘‘Auronal Black.’’ Addition to 764,733. ’ 773,346—Oct. 25, 1904. Albrecht Scumipt and Otto Ruopius, Germany. (Hochst.) Yellow sulfur dye and process of making same. 3-TOLUYLENE DIAMIN is allowed to react upon 1 mol. CARBON BISULFIDE, product added to melted sulfur at 110-130°, containing BENZIDIN or other aromatic amin (about 0.17 mol.), then temp. raised to 190-220°. Resulting powder is dissolved in 2.25 parts Na,S and dried in vacuum. Brown powd., insol. in aq., alc., ether and C,H,; a fast YELLow sulfide vat dye. Near S. 712 or 716—-“‘Kryogen Yellow G or R.” 775,570—Nov. 22, 1904. August L. Lasxa, Germany. (Oehler.) Dark-blue sulfur dye. (Process claimed.) 2’.4’-Dinitro 5-chlor 4-oxy 3-methyl DIPHENYLAMIN is added to aq. sulfur melt at 80-90°, refluxed, then dried at 1ros—110°. Higher temp. yields blackish dye. Product is sol. in conc. sulf. (B), in aq. Na,S (GB), pptd. by HCl (Br); sive sulfide vat dye. Near S. 726—‘‘Pyrogen Direct Blue.” 776,264—Nov. 29, 1904. Albrecht ScHMipt and Fritz BeErHmMann, Germany. (Hochst.) Blue sulfur dye and process of making same. Dimethyl 4’-amino 4-oxy 3-chlor DIPHENYLAMIN, from as-dimethyl 4-PHENYLENE DIAMIN, is condensed with 2-chlor PHENOL, then reduced or before reduction is heated in sulfur melt with glycerin and alc. to 94°. The proportion of S to Na,S in melt must be more than 1:4 Blue black powds., sol. in conc. sulf. (B), slightly sol. in alc. (RV fluor), almost insol. in glac. acetic; BLUE sulfide vat dyes. 776,885—Dec. 6, 1904. Melchior Bonicer, Switzerland. (Sandoz.) Green sulfur dye and process of making same. 4'-Tolyl 4”-oxy phenyl 4-NAPHTHALENE DIAMIN 6-, 7- or 8-sulfo derived from aryl 1-naphthyl- amin 5-, 6-, 7- or 8-sulfo acid is condensed with 4-amino PHENOL or its chlor deriv., heated with alkali polysulfides with or without Cu powder or salts, in alc. soln. or in presence of glycerin. Products are sol. in aq. (BG-YG), pptd. by acids (B), by caustic in excess (B), sol. in conc. sulf. (GyB), pptd. on diln. (B); Green sulfide vat dyes, fast to alks. and acids. S. 46—‘“Thional Green B.” Note 675,585. 77'7,.323—Dec. 13, 1904. Julius Ase, and Arthur LurrrincHaus, Germany. (Badische.) Blue dye and process of making same. METHYLENE VIOLET or its analogs, is dissolved at 10° in 7 parts 23 per cent fuming sulf. one part S,Cl, added and warmed to 30-35° then separated, and product heated in sulfur melt to 170°. Soln. of dried melt may be used as such or pptd. by oxidation with air, filt., etc. 266 DIGEST OF PATENTS Products are BLUE to blue vioLeT sulfide vat dyes, B being insol. in CHCl, and HCl while A is diff. sol. in CHCl, (B-BV non-fluor) and sol. in conc. HCl (B). Near S. 729—‘‘Kryogen Pure Blue R.”? Addition to 679,199. 778,478—Dec. 27, 1904. Karl Exvset, Germany. (Kalle.) Blue sulfur dye and process of making same. Chlor 1-NAPHTHOL and as-dimethyl 4-PHENYLENE DIAMIN, or other para diamin of benzene series, 1 mol. each in 40° NaOH, is mixed with NaOCl soln. to form INDOPHENOL, which is separated and reduced in 1o per cent soln. of Na,S to a phenyl NAPHTHYLAMIN deriv., and separated product fused in sulfur melt at 110°. Dark blue powds., insol. in aq., sol. in alc. (B), in dil. Na,S; green BLUE to vIOLET sulfide vat dyes. S. 731—“Thiophor Indigo.” 778,713—Dec. 27, 1904. Albrecht Scumipt, Germany. (Hoéchst.) Violet sulfur dye and process of making same. PHENOSAFRANINONE formed by decomp. PHENOSAFRANIN, is heated in sulfur to 190° with or without naphthalene as solvent and ANILIN, dimethyl anilin, phenol, or other, to form homolog of bluer shade. Violet black powd., insol. in aq., sol. conc. sulf. (VBk), in alk. sulfide (VR); VIOLET sulfide vat. dyes, bluer and faster when coppered, brighter when steamed. Near S. 729—‘“‘Kryogen Pure Blue.” 779,860—Jan. 10, 1905. Arthur Litrrincuaus, Germany. (Badische.) Violet sulfur dye and process of making same. (Process not claimed.) 2.6-Dichlor INDOPHENOL is heated to 120° in mixture of 4 parts Na,S, 4 parts aq., and 0.5 part sulfur, refluxed till indophenol disappears, diluted and oxidized. Dark powds., sol. conc. sulf. (B), in dil. Na,S (V); green Gray to blue Gray sulfide vat dyes. 782,905—Feb. 21, 1905. Richard Grey, Germany. (Berlin.) Orange sulfur dye and process of making same. 3-TOLUYLENE DIAMIN and 1 mol. diformyl 4-PHENYLENE DIAMIN (by action of formic acid on 4-phenylene diamin) are heated in sulfur at 200-220°. Yellow powd. insol. in aq. and alc., in dil. Na,S, (BrY); orange YELLOw sulfide vat dye, fast to washing and light. Note 813,643. 785,675—Mar. 21, 1905. August L. Lasxa, Germany. (Oehler.) ~ Orange sulfur dye and process of making same. Acetyl TOLUYLENE DIAMIN is coupled with diazotized ANILIN or other volatile aromatic amin and resulting dye melted with S and BENZIDIN or other base of diphenyl series, at 220-240°. Melt may be dissolved in aq. and pptd. with acid, or heated to 100° with Na,S and dried. Red brown powd., insol. in ale. or alk. carbonate, slightly sol. conc. sulf. and dil. caustic, sol. in alk. sulfide (YBr); orange YELLOW sulfide vat dyes. 790,167—May 16, 1905. Julius AsEL and Arthur LutrrincHaus, Germany. (Badische.) Blue sulfur dye and process of making same. Phenyl 4-amino 4’-oxy DIPHENYLAMIN, dichlor deriv., or other, is heated in strong NaOH soln. at 165°, sulfur added and heated again at 165-175°, more sulfur added and heated to 180-185°, dissolved in Na,S and pptd. by oxidation with air. Products are sol. in hot Na,S (Yt); BLUE to VIOLET reducing sulfide vat dyes, oxidized on fiber. 796,443—Aug. 8, 1905. Theodor MucHatt, Germany. (Kalle.) Red-violet sulfur dye and process of making same. ANILIN azO I-NAPHTHYLAMIN is boiled in strong HCl soln. with 4-amino PHENOL to form poly oxy ROSINDULIN which is heated in sulfur melt to 160°. Product is sol. in Na,S (VR), in conc. sulf. (B); a red vIOLET sulfide vat dye. 796,514—Aug. 8, 1905. Julius Horriein, Germany. (Weiler-ter-Meer.) Process of making a yellow sulfur dye. Nitro a-methyl BENZIMIDAZOLE, or amino deriv., and 1 mol. BENZIDIN are heated in 4 parts sulfur at 200-240°. Product may be dissolved in Na,S. Process compared with similar patents of numbers not shown. A green YELLOW sulfide vat dye. 4 GROUP XV.—SULFUR 267 8$01,598—Oct. 10, 1905. August L. Lasxa, Germany. (Oehler.) Brown sulfur dye and process of making same, RESORCIN and FORMALDEHYDE are condensed to form METHYLENE diresorcin then with 3- PHENYLENE DIAMIN or other meta diamin of benzene series heated in sulfur melt to 170—-220°. Black powds., sol. in conc. sulf. (YBr), in dil. Na,S (Br), pptd. by HCl (Br); fast Brown sulfide vat dyes. 802,049—Oct. 17, 1905. Ivan LEvINsTEIN and Ernest E. Nasr, England. Green-blue sulfur dye and process of making same, 4-Nitroso PHENOL 4-nitroso 2-cresol or ortho chlorine comps. of same is added to sulfuric acid soln. of an amino sulfo acid of benzene or naphthalene having free para amino positions, such as CLEVE’s acid, then pptd. by sod. carbonate, reduced by Na,S, heated with polysulfids to 110—-120°, and finally oxidized. If temp. is kept below 100° bluer shades result. Products are insol. in aq. and usual solvents, sol. conc. sulf. (GB); green BLUE reducing sulfide vat (Gy B) dyes. 813,643—Feb. 27, 1906. Richard Grey, Germany. (Berlin.) Orange-yellow sulfur dye and proeess of making same. 4-PHENYLENE DIAMIN and 1 mol. diformyl 3-TOLUYLENE DIAMIN, are melted with sulfur at 250°. Patent compares product with dye from closely related component. Brown red powd., fusol, ie ad., alc. sol. in NaOH (CY), pptd. by HCl (YBr), sol. in Na,S (Y); orange YELLOW sulfide vat dye, fast to washing and milling. Addition to 782,905. 818,980—Apr. 24, 1906. Albrecht ScuMip?t, Germany. (Hochst.) Sulfur dye and process of making same. 2-Amino 7-Oxy PHENAZIN HCl or other hydroxylated azin, is heated with alk. polysulfide containing CuSO, at 110°, then refluxed. Methyl and Cl derivs. of above, N_ substituted safraninones and derivs., etc., and copper or Cu,S equivalents, also claimed. Products are sol. in hot Na,S; rep, dark RED to vioLET sulfide vat dyes changing to BLUE when coppered on fiber. Note 829,740. 820,501—May 15, 1906. Paul Junius and Eduard Mincu, Germany. (Badische.) Green-blue sulfur dye and process of making same. CHLORANIL together with as-dimethyl 4-PHENYLENE DIAMIN thio sulfo are heated at 65 to 75° in aq. soln. containing Na,S, soda and sulfur. Mercaptans and disulfids may be used for thio sulfo comps. and diethyl deriv. also. Violet black powds., slightly sol. hot aq., (B), sol. conc. sulf. (BG), in hot Na,S (YBr), slightly sol. in CH;NH, (G), in C,H.OH (GB), insol. glac. acetic, alc., acetone, contains no Cu; green BLUE sulfide vat dyes, fast to washing, light, Cl. 821,378—May 22, 1906. C. Ris, Switzerland. Blue sulfur dye and process of making same. as-Dimethyl 4-PHENYLENE DIAMIN, or other para diamin, and 1-NAPHTHOL, are condensed to form INDOPHENOL which is heated in sulfur mixture at 115°, then dissolved in aq. and oxidized by air or pptd. in leuco form. Dark blue powd., insol. in aq., sol. in alc. or C,H, (B), sol. in Na,S (G), in conc. sulf. (Br), and decomp.; BLUE to VIOLET sulfide vat dyes. S. 731—‘“Thiophorindigo.” 829,740—Aug. 28, 1906. Albrecht Scumipt, Germany. (Hoéchst.) Bordeaux-red sulfur dye and process of making same. Ethyl tolu-sAFRANINONE HCl, or other safraninone of fatty series, is refluxed at 110 to 135° with Na,S and S. Higher temp. gives bluer products. Glycerin may be used. Bordeaux RED sulfide vat dyes changing to vIOoLET when coppered. Note 701,435 for related dye, and 818,980. 841,877—Jan. 22, 1907. August L. Lasxa and Georg List, Germany. (Griesheim.) Blue sulfur dye and process of making same. 4-Amino PHENOL and 2-chlor methyl ANILIN, or homologs, are oxidized to INDOPHENOL by bichromate in H,SO, soln. keeping below O°. On reduction in alk. soln. product gives 4’-oxy methyl 4-amino 3-chlor DIPHENYLAMIN, which is heated with polysulfids to 115°. Dark violet 18 268 DIGEST OF PATENTS powds., almost insol. in aq., alc., C,H, and glac. acetic, sol. hot glycerin and conc. sulf. (darkB), in dil. Na,S (V); BLuE sulfide vat dyes, fast to washing, light, acids. 843,156—Feb. 5, 1907. August IL. Lasxa, Germany. (Griesheim.) Green sulfur dye. (Process claimed.) 4-Amino PHENOL is mixed in alk. soln. with 1 mol. 1-naphthol 4-rotyzt sulfonamid, cooled and condensed, by adding hypochlorite, to an indophenol which may be reduced with Na,S to phenyl naphthylamin deriv. The INDOPHENOL or its leuco paste is heated at 120° with alk. polysulfids containing copper powder and CuSO, Dark green powds., diff. sol. in aq., sol. conc. sulf. (B), in Na,S(G); GREEN sulfide vat dyes, fast to washing. 864,644—Aug. 27, 1907. W. Herzperc, O. SCHARFENBERG and M. Ronus, Germany. (Berlin.) Sulfur dye and process of making same. 4-Tolyl sulfo 4-amino 4’-oxy DIPHENYLAMIN, chlor deriv. or analogous comps., is boiled with alk. polysulfids, diluted and pptd. by air, then treated with conc. sulfuric acid to remove the aryl sulfo group. Dark bronzy powds., insol. in aq., boiling dil. NaOH and usual organic solvents, sol. in conc. sulf. (B-V), pptd. on diln.; sLux sulfide vat dyes, that need not be coppered to be fast to washing, light, and acids. 866,939—Sept. 24, 1907. Fritz LEHMANN, Germany. (Bayer.) Reddish-brown sulfur dye. 4-Amino PHENOL and 3-TOLUYLENE DIAMIN with NH, and MnO, etc., are condensed to form amino oxy TOLU-PHENAZIN, whish is heated with sulfur and Na,S to 135°. Dark brown powd., sol. dil. Na,S (dark Br), insol. in 27 per cent NaOH, sol. conc. sulf. (dark Br ), pptd. on diln. (RBr); red Brown sulfide vat dye remaining brown when coppered. Near S. 739—‘‘Immedial Bordeaux G.” Note 701,435 and 818,980. 886,532—May 5, 1908. Miles R. Morrart and Harry S. Spira, Rhode Island. Brown sulfur dye and process of making same. Crude woop Tar is treated with alkali to remove phenols and cresols, and residual tar heated in sulfur melt not to exceed 200° until dry. Product is partly sol. in aq., sol. in alk. sulfids, pptd. by acids; Brown sulfide vat dye, fast to light, scouring and cross dyeing. 889,936—June 9, 1908. Georg List, Germany. (Griesheim.) Brown sulfur dye and process of making same. 2.4-Dinitro chlor BENZENE or other aromatic m-dinitro compound and GLYCERIN are heated with alk. polysulfids to 200-240°. List of components and color of resulting dyes given. Gray brown powds., sol. in aq. (Br), pptd. by HCl (Br); Brown sulfide vat dyes. 8§92,455—July 7, 1908. Werner Scumipt, Germany. (Cassella.) Yellow sulfur dye and process of making same. Dehydro thio TOLUIDINE, or analogous compounds such as primulin bases and BENZIDIN or thio benzidin, is heated with sulfur to 210° then Na,S added and again heated to 120-125° till sol. in aq., diluted and pptd. with HCl. Brown powds. insol. in ag., acids or organic solvents, sol. conc. sulf. (YGy), pptd. on diln. (Br), sol. conc. NaOH (YBr), sol. in Na,S; green YELLOw sulfide vat dyes. 893,499—July 14, 1908. Benno Homoika and Robert WeEtpE, Germany. (Hochst.) Process of making sulfur dyes and their leuco bodies. (Process classed as dye.) Two mols. 2-thio aceto phenones united as dithio comps. 2-Thio ACETOPHENONE or deriv., obtained from amino comps., is oxidized by air or other agent in alk. soln. Products must be reduced to leuco form for dyeing. Or dyes can be prepared in leuco form by melting thio acetophenone in Na,S, adding sulfur and heating until about one half water of crystn. of Na,S has evaporated. When oxidized same dyes as above result. They are insol. in usual solvents, reduced by alk. agents; violet Brug sulfide vat dyes. 895,637—Aug. 11, 1908. Alfred Herre and Bernhard JarcKet, Germany. (Bayer.) Brown sulfur dye. 3-TOLUYLENE DIAMIN, or other meta diamin, and 3-NITRANILIN or other meta amin, are heated in sulfur to 240-250° then boiled in Na,S soln. One component must be alkylated in GROUP XV.—SULFUR 269 nucleus. Dark powds., insol. in aq., sol. dil. Na,S (Br), diff. sol. NaOH and conc. sulf. (Br); yellow-BROWN to ORANGE sulfide vat dyes. List of components and colors of resultant dyes is given. Near S. 711—‘‘Immedial Orange B.” Note 714,542 for patent with similar process, and 896,916. $96,916—Aug. 25, 1908. Bernhard JAECKEL, Germany. (Bayer.) Yellowish-brown sulfur dye. 3-TOLUYLENE DIAMIN or Other aromatic meta diamin or triamin and 3-NITRANILIN or other nitro amin, are heated with BENZIDIN in sulfur to 240-250° then boiled in Na,S soln. One component must be alkylated in the nucleus. Yellow brown powds., insol. in aq., sol. dil. Na,S, (YBr), diff. sol. NaOH (YBr); vELLOW to ORANGE sulfide vat dyes. Homolog of S. 711—“‘Immedial Orange N.” Addition to 895,637. 897,873—Sept. 8, 1908. Emile T. Bunpsman, California. (Pt. Loma.) Sulfur dye and process of making same. SUGAR, grape sugar, glucose, cane sugar, etc., is heated in sulfur melt with or without 3-NITRANILIN, 3-phenylenediamin, sulfanilic acid, benzidin, diphenylamin, or other compounds, that may or may not themselves give rise to dye. Dark. powd., sol. in aq., alc., Na,CO, and NaOH; a dark Brown sulfide vat dye, which when heated with HCl forms another coloring “matter insol. in aq., etc., sol. in Na,S soln., also a dark Brown sulfide vat dye. Modification of S 706—‘‘Cachou de Laval.” 899,845—Sept. 29, 1908. Alfred ScHAARSCHMIDT, Switzerland. (Basle.) Orange to orange-yellow wat dye and process of making same. A sulfur containing anthraquinone deriv., probably a thiazin indanthrene. 2-Methyl ANTHRAQUINONE or halogenated derivs. with halogen in nucleus heated to 290—-300° then at 320-330° in sulfur, then oxidized by hypochlorite. Orange to brown yellow powds., sol. in cone. sulf. (V-VB) in 24 per cent fuming acid (G); ORANGE to orange YELLOW vat dyes fast to washing, light, Cl. Note 902,895. 901,970—Oct. 27, 1908. Gustav E. Junius, Germany. (Sanderson.) Black sulfur dye and process of making same. Nitroso 2-crEsot boiled in aq. soln. of Na,S and S. It is better to treat first with dilute sulfide soln., separate product and treat again with stronger Na,S and S. Product must be pptd. from soln. not evap. to dryness. It is insol. in aq., acids, alk. carb., sol. in alk. sulfids; a green BLACK sulfide vat dye, fast to Cl, light, milling, alkalies, acids, cross dyeing. 902,895—Nov. 3, 1908. Bertram Mayer and A. ScHaarscHMip?, Switzerland. (Basle.) Orange-to-yellow wat dye and process of making same. Probably an N-dichlor- methyl thiazin indanthrene. w-Dichlor methyl ANTHRAQUINONE (containing some monochlor) or related comp., is heated with sulfur, purified and treated with aik. hypochlorite. Orange to yellow powds., sol. in conc. sulf. (dull R-RV), in 24 per cent oleum (BkG-BrG); yELLow vat dyes, fast to washing, light, Cl. S. 7o5—‘“‘Cibanon Yellow R.” Addition te &99,845. 904,809—Nov. 24, 1908. Erich Saunt, Germany. (Cassella.) Yellow-olive dye and process of making same. 4-PHENYLENE DIAMIN heated in 2 parts sulfur with 3-PHENYLENE DIAMIN to 200-240°, cooled, pulverized and heated at 115° in 3 parts Na,S till aq. sol., diluted and pptd. by acids, by air, salts of lime or NH,. Or 3-phenylene diamin may be heated with S to form thio compound then para salt added. Dark powd., insol. in neut. or acid liquids, sol. in alk. sulfids; fast green BRowN sulfide vat dye. 904,224—Nov. 17, 1908. Alcide F. Porrrier, France. (St. Denis.) Process of making black sulfur dyes. Dinitro pHENoL, Na salt, instead of fusing with polysulfids is boiled in polysulfid soln. of definite compos. for long time, raising temp. to 106-108° by addition of salts to soln., the 270 DIGEST OF PATENTS proportion of polysulfid being such that the dyestuff as formed separates as a ppt. GROUP XXII.—INTERMEDIATES 323 and the benzidin comp. pptd. by neutn. with alk. Heated in closed vesse! at 170° with water the sulfo acid of 2-ethoxy benzidin is formed. 380,928—Apr. 10, 1888. A. F. Porrrter and Z. Roussin, France. (St. Denis.) Production of diazoic coloring-matters. 1-naphthylamin-6-or 7-sulfo acid. I-NAPHTHYLAMIN mixed with 3.5 parts fuming H,SO, (28-30 per cent SO,), below 25° and let stand 2-3 days, then converted to Na salt. Differs from Piria, Ewer or Pick’s acids. 381,471—Apr. 17, 1888. FE. Hass—ENKAMP, Germany. (Dickerson.) Process of producing blue-red coloring-matter. Alkyl-1-naphthylamin-sulfo acid. I-NAPHTHYLAMIN sulfo acid, Na salt, in aq. soln. with 1 mol. mMretTuyt sulfate Na salt, heated to hours in an autoclave to 180—200°. 382,832—May 15, 1888. Christian RupotpH, Germany. (Ocehler.) Production of yellow coloring-matter. (Product also claimed.) (a) Benzylidene 3-toluylene diamin. (b) Tetra amino ditolyl phenyl methane. (c) Hydro diamino dimethyl phenyl acridin. : 3-TOLUYLENE DIAMIN or other, mixed to paste with aq. and BENZALDEHYDE to form (a). Product heated in aq. to 60-70° with 3-toluylene diamin sulfate. Or in one operation benzalde- hyde heated with 3-toluylene diamin, NaOH and alc. (or 3-toluylene diamin HCl or sulfate and alc.) to form (b). Product (b) heated in autoclave at 160° with HCl to form (c). 389,127—Sept. 4, 1888. Hans Wo .rFrf, Switzerland. Production of new azo colors. (Product also claimed.) 3-Nitro-4’.4”-diamino triphenyl- methane or homologs and derivs. 3-Nitro BENZALDEHYDE, condensed with 2 mols. ANILIN, or other aromatic amin by refluxing 4 hours with HCl (21°) to form 3-nitro 4’.4”-diamino triphenylmethane, etc. 395,080—Dec. 25, 1888. Christian Rupo_pH, Germany. (Oehler.) Coloring-matter. Hydro triamino dimethyl phenyl acridin. Nitro tetra amino ditolyl phenyl METHANE HCl reduced in warm aq. soln. by SnCl, and HCl, diluted, Sn. pptd. by H,S and base pptd. from filt. by alkali, then product heated in auto- clave with HCl (16°). 395,474—Jan. 1, 1880. F. Bayer, Germany. (Bayer.) Manufacture of dye-stuffs or coloring matters. 2-Naphthylamin 7-sulfo ‘Delta’ or F acid. 2-NAPHTHYLAMIN sulfonated in 3 parts H,SO, at 150-170° for 1 hour, the alk. soln. pptd. at 80° with H,SO, and the new sulfo acid which remains in soln. crystd. on evapn. or pptd. as Ba or Na salt. 396,574—Jan. 22, 1889. Alfred Kern, Switzerland. Formation of purple coloring-matter. (Product, not process, claimed.) Alkyl ester of dimethyl gallocyanin. Gauuic acid, or tannin, in 2.5 parts methyl alc. soln., treated with dry HCl vapor or with conc. H,SO,. 403,678—May 21, 1889. Carl Kussmavut, Switzerland. (Basle.) Metaamidophenol. (Process, not product, claimed.) 3-Amino phenol, m.p. 121°. Caustic soda and a little aq. fused at 270°, to which aniLINn 3-sulfo is added and temp. kept at 280-290° for an hour, diluted, acidified, filtered to remove resins, neut. with alk. carb.; extracted with ether, purified, etc. : 405,938—June 25, 1889. Momme AnpreEsen, Germany. (Berlin.) Manufacture of a new alpha naphthol-disulphoniec acid. (Product, not process, claimed.) 1-Naphthol-3.8-disulfo or 1-naphthylamin-3.8-disulfo. NAPHTHALENE disulfonated in H,SO, and cHLoRHypRIN or in fuming H,SO, (23 per cent anhyd) below 60°, nitrated, reduced, neut. by CaO, sodium salt formed, soln. conc., then cooled and filtered to remove (4.8-) comp. Soluble salt of patent (3.8-) is pptd. out of filtrate by acid. Corresponding naphthol results by diazotizing then boiling in dil. acid. 324 DIGEST OF PATENTS 407,906—July 30, 1880. Bruno R. Sr1Fert, Germany. (von Heyden.) Process of making paraoxybenzoie acid. PHENOL, as dry K salt, is heated in closed vessel under pressure at 180-250° and dry CO, forced in until salt is saturated. Pressure may vary from a little more than one up to 20 atms. 410,295—Sept. 3, 1880. Rudolf Scumirt, Germany. (von Heyden.) Process of making beta-naphthol carbon acid. 2-Naphthol carbo acid, m.p. 216°, a stable form. 2-NAPHTHOL, alkali salt, is heated with CO, under pressure to 200-250°. Note 350,468 for unstable acid by similar process. 412,613—Oct. 8, 1880. Albert HEerrMANnN, Germany. (Hochst.) Coloring-matter. 3-Oxy tetra alkyl diamino triphenylmethane. 3-Amino tetra ethyl diamino TRIPHENYLMETHANE, or other, with HCl and nitrite is heated to 60°, then boiled. Free base is pptd. by alkali. 415,257—Nov. 10, 1880. Moritz Uxtricu, Germany. (Bayer.) Process of making dioxynaphthaline monosulpho-acid. Dioxy naphthalene sulfo acids. 2-NAPHTHOL disulfo (R or G) is heated to 200° with strong caustic alkali, 418,657—Dec. 31, 1889. Gustav ScHuLtz, Germany. Production of orange and red dye-stuffs. Diamino dimethyl stilbene sulfid. XYLIDIN, or other amino comp., 2 parts, is heated with 1 part sulfur as long as H,S escapes. 420,373—Jan. 28, 1890. Otto N. Wirt, Germany. (Badische.) Ammonium salt of beta-naphthohydroquinone-beta-sulphonie acid. 1.2- Naphthohydroquinone sulfo, NH, salt. Amino 2-NAPHTHOL b-sulfo purified, is oxidized with HNO, to 1.2-NAPHTHOQUINONE sulfo, then purified by forming soluble sulfite comp. and pptd. by acids. Product is used in 420,372 and 420,374 Group VI. 423,550—Mar. 18, 1890. C. DuissErc, Germany. (Bayer.) Process of making blue dyes. Benzidin sulfone disulfo. Benzipin sulfate converted to sulfone by heating to 80° with fuming H,SO, (40 per cent anhyd.) is then heated at 160° until sol. in alk. and not pptd. by acetic acid (evidence of mono sulfo acid). 425,525—Apr. 15, 1890. Jakob Scumip, Switzerland. (Basle.) Orthonitroparadiamido-diphenyl. 2-Nitro benzidin. BENnz1DIN sulfate dissolved in 10 parts (66°) H,SO, below 5° and HNO, added at this temp. 427,564—May 13, 1890. Robert GNEHM and Jakob Scumip, Switzerland. (von Heyden.) Carboniec-acid compound of meta-amidophenol. 3-Amino phenol carboxylic. 3-Amino PHENOL is heated with (NH,),CO,, or K or NaHCO,, and aq. in autoclave at 110°, soln. evaporated to small bulk, very slight excess of HCl added, impurities filtered off and carbo. acid pptd. by HCl. 4.27,565—May 13, 1800. Robert GnEHM and Jakob Scumip, Switzerland. (Basle.) Carbonic-acid compound of dimethyl meta-amidophenol. Dimethyl 3-amino phenol carbo acid. Dimethyl 3-amino PHENOL, Na salt, heated in autoclave at 120-140° with compressed CO,. 440,953—Nov. 18, 1890. W. Masgert, Germany. Blue dye. (Process and intermediate claimed, not dye.) 1.8-Dioxy naphthalene and mono or disulfo acids. NAPHTHALENE disulfonated by sulfuric acid cHLorHypRIN (C,H,.Cl1.0H.OSO,H), then fused in 3-4 parts NaOH, to form dioxy naphthalene (m.p. 248-252°), which may be mono sulfonated r | z : GROUP XXII.—INTERMEDIATES 325 by conc. sulfuric at 60° or disulfonated by heating to 90-130°. Properties of this in compar- ison with other dioxy naphthalenes given in detail. 444,679—Jan. 13, 1801. Moritz Utricu, Germany. (Bayer.) Dioxynaphthaline-mono-sulphonie acid. (Process also claimed.) 1.8-Dioxy naph- thalene-4-sulfo ‘“‘S.’’ I-NAPHTHOL 4.8-disulfo “S’’ heated in closed vessel at 240° with strong NaOH soln., etc. Open vessel may also be used. Azo dyes formed with derived diazo comps. are fast to light, air, and of bluer shades. Note 423,970 and 466,841 employ above acid Group VI. 447,189—Feb. 24, 1891. Paul Junius, Germany. (Badische.) Red dye. Diamino diphenyl ketoxim. Diamino BENZOPHENONE (obtained by reduction of dinitro diphenylene ketone in hot alc. soln. with Na,S), in hot dil. HCl soln. to which HypRoxyLAmin HCl or other, is added; soln. then made alk., boiled and pptd. by acid as KETroxim. Product not very stable. Note intermediate is not claimed in patent. 449,551—Mar. 31, 1891. Eugene Mentua, Germany. (Badische.) Dihydroxynaphthalene. 2.3-Dioxy naphthalene 6-sulfo ‘“R.’’ 2-NAPHTHOL 3.6-disulfo “‘R’”? fused in NaOH at 240—280° until test portion neut. with HCl, filt. and soln. pptd. by NaCl gives highest yield of comp. 449,551—Mar. 31, 1801. Eugene Mentua, Germany. (Badische.) Dihydroxynaphthalene. 2.3-Dioxy naphthalene. (a) 2.3-DIOXY NAPHTHALENE 6-sulfo is fused in NaOH at 300—320° until test portion, acid- ified, gives highest yield to ether, neutralized, filtered while hot, cooled and extracted with ether or fusel oil, etc. Product may be purified by crystn. from aq. (b) Or 2.3-dioxy naph- thalene 6-sulfo is heated in 25 per cent H,SO, in closed pressure resistant vessel to 200°. ‘Test for end of reaction is made by extracting with ether and coupling aq. ext. with diazo benzene in alk. soln. 454,645—June 23, 1801. Leo Gans, Germany. (Cassella.) Amido-naphthol-monosulIphonie acid. 2-Amino 8-naphthol 6-sulfo, “Gamma.” ” 2-NAPHTHOL 6.8-disulfo, “Gamma,” of 331,059 treated with NH, to form 2-naphthylamin di- sulfo, which is heated in strong NaOH soln. in autoclave at 210°. Couples easily with diazo comps. in both acid and alk. soln. For derived dyes, see same number, and 442,369 Group VI. 455,442—July 7, 18091. Jakob ScumMip, Switzerland. (Basle.) Betadelta-amidonaphthol. 2-Amino 7-naphthol. 2-NAPHTHOL 7-sulfo heated with NaOH at 260—300°, is dissolved, partly neutralized, impur- ities filtered off, fully neut., filt. and amino naphthol separated from unchanged sulfo acid by soln. in dil. HCl. Special reactions for identification are given. 456,081—July 14, 1801. Maurice CERESOLE, France. (Badische.) Red dye-stuff. Ethyl 3-amino phenol. Ertuyt chloride and METrANILIC acid are combined under pressure, then treated with alkali in usual way, or ethyl an1Li1Nn is heated at 60° in fuming sulf. acid (28 per cent SO,) then at same temp. or at 40° more fuming acid (75 per cent SO,) added. The dry sulfo acid, Na salt, is fused in KOH at 200-220° to form phenol. 456,627—July 28, 1891.- C. A. Martius, Germany. (Berlin.) Process of making azo dyes. 1-Naphthol 4.8-disulfo “d’” or “S.” NAPHTHALENE disulfo obtained from NAPHTHALENE by treatment with fuming H,SO, or sul- furic monochlorhydrin, nitrated in alfa position, reduced and converted into naphthol. (Process not given.) 456,897—July 28, 1891. C. A. Martius, Germany. Azo dye. (Process, not product, claimed.) 1-Naphthol 2.4-disulfo. NAPHTHALENE disulfo (from naphthalene and fuming sulfuric) nitrated, reduced, and con-. verted into naphthol deriv. 326 DIGEST OF PATENTS 458,284—Aug. 25, 1891. H. Kuzre.t, Germany. (Hochst.) Azo dye. Naphthol trisulfo acid monamid. NAPHTHALENE is trisulfonated, then nitrated and reduced to give NAPHTHYLAMIN trisulfo, which with nitrous acid and subsequent boiling with dil. acid yields a naphtho sultone disulfo acid which is converted by ammonia into naphthol trisulfo monamid. 458,285—Aug. 25, 1801. Hans Kuze.t, Germany. (Hochst.) Amido-naphthol monosulphoniec acid. (Process also claimed.) 2-Amino 8-naphthol 6-sulfo, diazotizable “R acid.” 2-NAPHTHYLAMIN disulfo (from 2-naphthol disulfo and NH, or by sulfonation of 2-naph- thylamin) is heated in open or closed vessel with 2 parts NaOH and some aq. slowly to 260-280°. The sulfo groups are removed successively, the first stage yielding amino naphthol mono sulfo of patent. 458,286—Aug. 25, 1891. Hans Kuzet, Germany. (Hochst.) Amido-oxynaphthaline disulphonic acid. 1-Amino-8-naphthol-3.6-disulfo. I-NAPHTHYLAMIN trisulfo obtained from NAPHTHALENE trisulfo by nitration and reduction, is heated with 2 parts NaOH containing % parts aq. to 220-260° till foaming ceases. Product may be combined in acetic or alk. soln. with diazo bodies. 464,135—Dec. 1, 1891. M. Horrman, Germany. (Cassella.) Blue dye. (Process also claimed.) 1-Amino-8-naphthol-3.6-disulfo, ““H’’ acid. NAPHTHALENE 2.7-disulfo, dinitrated and reduced to diamino deriv. heated at 1oo—130° in dil. sulfuric acid, gives fine yellowish needles of acid ‘“‘H.”’ 464,566—Dec. 8, 1891. M. Horrmann, Germany. (Cassella.) Blue dye. 1.5-Diamino naphthalene 3.7-disulfo. NAPHTHALENE 2.6-disulfo lime salt, dinitrated at common temp., is reduced with Fe and acetic acid. -471,659—Mar. 29, 1802. Eduard VoncERICHTEN, Germany. .(Héchst.) Process of making diamino-diphenylmethan bases. Diamino diphenylmethane bases. ANILIN is condensed with FORMALDEHYDE to form anhydro formaldehyde anilin which is heated at 100° with excess anilin and aninin HCl. Or DIPHENYLAMIN in alc. soln. at 60° is condensed with formaldehyde. Other components claimed. 473,467—Apr. 26, 1892. Hans Kuzet, Germany. (Hoéchst.) Process of making naphthosultondisulphonic acid. (Product also claimed.) Naphtho sultone disulfo, for making chromotropic acid. NAPHTHALENE trisulfo, nitrated and reduced to NAPHTHYLAMIN trisulfo which is acted upon by sulfuric and nitrous acids in boiling aq. soln. till N ceases to evolve. Resulting sultone forms sulfamid with NH,, and with hot aq. or dil. alk. reforms the trisulfo acid and when heated strongly with alkali yields chromotropic acid. Note 511,892 Group VI. 488,290—Dec. 20, 1892. Bruno R. Serrert, Germany. (von Heyden.) Process of making oxyuvitie acid. Cresot as dry alk. salt is heated to 160-220° in’ pressure vessel and CO, forced in to sat- uration. : 493,562—Mar. 14, 1893. Jakob Scumip and Robert Pacanrini, Switzerland. (Basle.) Monosulpho-dioxynaphthoie acid. (Process also claimed.) Sulfo dioxy naphthoic acid. 2-NAPHTHOL carbo heated in fuming H,SO, (24 per cent anhyd.) at 1oo-120° to form di- sulfo 2-NAPHTHOL carbo which is heated in conc. NaOH to 210-240° in’ closed or open vessel. Note 493,563 and 64 and 557,437. Group VI, which employ this intermediate. agi eg ea aa GROUP XXII.—INTERMEDIATES 327 498,404—May 30, 1808. P, Ort, Germany. (Bayer.) Greenish-blue dye. (Process also claimed.) 4’-Tolyl 1-naphthylamin 8-sulfo. I-NAPHTHYLAMIN 8-sulfo 1 part, is heated with 4 parts 4-roLumpDIN and 1 part 4-toluidin HCl at 160-180° for 10 hours. Note anilin deriv. in 498,404, dye patent Group VI. 498,882—June 6, 1893. © Meinhard HorrmMann, Germany. (Cassella.) Naphthylene-diamine disulpho-acid. (Process also claimed.) Naphthalene 1.5-di- amin 3.6-disulfo. NAPHTHALENE 3.6-disulfo nitrated below 10° to dinitro product, is reduced with Fe and acetic. Product can be tetrazotized and coupled with phenols, etc., to form valuable colors. 511,532—Dec. 26, 1893. R. Korue, M. Uxricu, and O. Dresser, Germany. (Bayer.) Blue dye. (Process also claimed.) 1-Amino 8-naphthol 2.4-disulfo acid. 1-Naphthylamin 4.8-disulfo acid, heated at 80-90° in 4 parts fuming H,SO, (40 per cent SO,) until a test gives no diazo deriv. or azo dye with a coupling agent; diluted, neut. with Ca(OH),, filt., and Na,CO, added to form Na salt then evap. and pptd. by alc. as yellow crysts. of the Na salt of naphthalene sodium imino sulfone disulfo acid. This is heated with 2.5 parts of potash or soda to 170°, and the amino naphthol disulfo acid pptd. from soln. as the acid Na salt by HCl. . 511,708—Dec. 26, 1893. Max Moetuier, Germany. (Berlin.) Production of amido-naphthol disulfonie acid. (Product also claimed.) 1-Amino- 8-naphthol-3.5-disulfo “Cleves”? (or 1.8.2.4). I-NAPHTHYLAMIN disulfo is trisulfonated in H,SO, (23 per cent anhyd.) and product fused in NaOH at 170-220° till fluorescence of alk. soln. disappears, and acid Na salt then formed. 511,898—Jan. 2, 1894. Hans Kuze.t, Germany. (Hochst.) Naphthol trisulfonic-acid monamid. (Process also claimed.) Naphthol trisulfo mono- amid. I-NAPHTHOL 8-sultone 3.6-disulfo, Na salt, is mixed at ordinary temp. with 2-3 parts 20 per cent ag. ammonia. Ca or Mg salts of sulfo acid and alcoholic ammonia or ammonia gas can also be used. Addition to 473,467. 516,585—Mar. 13, 1894. Heinrich A. BERNTHSEN, Germany. (Badische.) Red rhodamin dye. (Process also claimed.) Ethyl 3-amino-4-cresol. Ethyl 2-ro.uipin, or other, is heated in 2 parts fuming sulf. acid (23-70 per cent SO,) at 60° to form para sulfo acid, the Na salt of product fused in NaOH at 220-260°, cooled, pptd. by acid and extracted by ether from sat. soda soln. 516,752—Mar. 20, 1894. Johann J. Brack, Switzerland. (Durand.) Diamido base. (Process also claimed.) Asymmetric diamino bases suitable for production of substantive cotton dyes. ToLipIn, or other, and aniLin HCI condensed in alcohol with FORMALDEHYDE to form tolidin anilin methane, or other. Note 516,753, 54, 55, and 531,149. 516,753—Mar. 20, 1894. Johann J. Bracx, Switzerland. (Durand.) Diamido base. (Process also claimed.) Asymmetric diamino bases for substantive cotton colors. To.pin, or other, and 3-PHENYLENE DIAMIN that has been half neutralized with HCl, are condensed in alcohol with FORMALDEHYDE. Other components claimed. Addition to 516,752. 516,754—Mar. 20, 1894. Johann J. Brack, Switzerland. (Durand.) Diamido base. (Process also claimed.) as-Diamino bases for substantive colors. DIANISIDIN and basic 3-PHENYLENE DIAMIN (one-half neutralized with HCl) condensed in alc. soln. with FORMALDEHYDE. Other components claimed. Addition to 516,752. 328 DIGEST OF PATENTS 516,755—Mar. 20, 1894. Johann J. Brack, Switzerland. (Durand.) Diamido base. (Process also claimed.) as-Diamino bases, for substantive cotton colors. DIANIsIDIN and aniLIn HCl or 2-amino PHENOL are condensed in alc. soln. with FoRMAL- DEHYDE. Addition to 516,752. 521,095—June 5, 1894. H. A. Berntusen and P. Junius, Germany. (Badische.) Substantive blue dye. 2-Amino 5-naphthol 7-sulfo. 2-NAPHTHYLAMIN 5.7-disulfo is fused in caustic at 170-195°. Note Armstrong and Wynne, Proc. Chem. Soc., 1890, 128. 524,069—Aug. 7, 1894. C. O. Miuier, Switzerland. (Basle.) Blue tetrazo dye. 1.7-Dioxy naphthalene 4-sulfo. t-Oxy 4.7-disulfo 2-NaPpHTHOIC acid is fused in NaOH at 230-—290°. Note 524,070. 524,070—Aug. 7, 1894. C. O. Mi.uer, Switzerland. (Basle.) Blue tetrazo dye. (Process also claimed.) 1.7-Dioxy 4-sulfo 2-naphthoic acid. 1-Oxy 4.7-disulfo 2-NAPHTHOIC acid is fused in NaOH, or other, at 180-200°. In 524,069 the same material at a temp. of 230-290° yields dioxy NAPHTHALENE sulfo. §24,220—Aug. 7, 1894. C. Scurauset, Germany. (Badische.) Substantive blue dye. (Process also claimed.) Benzoyl 1-amino 8-naphthol 4-sulfo. I-NAPHTHYLAMIN 8-sulfo is fused in NaOH at 230-240° until all is sol. in dil. hot HCl, the resulting 1-AMINO 8-NAPHTHOL is sulfonated in conc. H,SO, below 20° till soluble clear in dil. NaOH, separated, dissolved in soda and BENzoyL chloride added, keeping temp. below 5°. 524,221—Aug. 7, 1894. Conrad ScHrAuBE and Eugen Romic, Germany. (Badische.) Phenylrosindulin sulfo-acid. Phenyl rosindulin mono sulfo acid.* 2-Amino 4-sulfo DIPHENYLAMIN and 2-OXY NAPHTHOQUINONE anil are boiled in diluted alc. (2:3) until dil. alk. soln. of separated ppt. is repptd. with excess alk. and mother liquor is not colored orange red on testing with naphthoquinone anil. Heated at 100° in 4 parts 96 per cent H,SO, the disulfo acids that are formed are violet-rED acid dyes. 524,261—Aug. 7, 18094. C. L. Mtuuer, Germany. (Badische.) Orange diazo dye. 3-Phenylene diamin disulfo. 3-PHENYLENE DIAMIN is mixed while cool with fuming H,SO, (40 per cent anhyd) then heated to 100-120°. At least 2 mols. of free SO, must be used, the amount of SO, above 2 mols., however, may be varied inversely with the temperature. ; Note 524,262 gives same process Group VI. 526,786—Oct. 2, 1894. Otto Manassrt, Germany. (Bayer.) Process of making phenol alcohol. 2- and 4-Oxy benzyl alcohol, homologs and derivs. PHENOL, or its di or trioxy, nitro, sulfo or carbo derivs. or alkyl esters, is condensed with FORMALDEHYDE by boiling in 10 per cent NaOH, or other caustic or carbonated alk. or cyanide. 531,149—Dec. 18, 18094. J. J SBEAGK; Switzerland. (Durand.) Substantive red dye. (Process also claimed.) as-Di-, tri-, or tetra-amino bases for sub- stantive colors. To.iipIn is boiled in dil. HCl soln. with FoRMALDEHYDE till pptd. base is completely sol. in acid. Amount of material, strength of acid, quantity of solvent, temp. and time of heating in- fluence character of product. Addition to 516,752. 532,125—Jan. 8, 1895. A. WEINBERG, Germany. (Cassella.) Blue disazo dye. (Process also claimed.) 1-Chlor 8-naphthol 3.6-disulfo. I-AMINO 8-NAPHTHOL 3.6-disulfo is diazotized, insol. diazo comp. filt. off and treated at 10° *Tsomer of 428,530 in that sulfo group is attached to benzene residue of naphth-phenazin nucleus Gr. V. i, il ee ili . NOR WAR ae 5h. 4 a x GROUP XXII.—INTERMEDIATES 329 with to per cent HCl and Cu,Cl, till all becomes soluble. Copper then pptd. by H,S and comp. in filt. pptd. by NaCl. Original patent for this compound is 464,135. 532,479—Jan. 15, 1895. K. PatHE and O. Dresset, Germany. (Bayer.) Red dye. (Process also claimed.) 2-Amino 5-naphthol 1.7-disulfo. 2-NAPHTHYLAMIN 5-Sulfo is further sulfonated at 100° in fuming sulf. acid (10 per cent $O,) to trisulfo comp. (2.5.1.7) then fused in KOH in closed vessel under pressure at 180° to form naphthol. 533,463—Feb. 5, 1895. M. Horrmann, Germany. (Cassella.) Black azo dye. (Process also claimed.) Naphthalene 1.4-diamin 6- or 7-sulfo. I-NAPHTHYLAMIN 6 or 7-sulfo is acetylated, nitrated, reduced and saponified. The nitro naphthylamin sulfo comp. (1.4.6 or 1.4.7) formed as intermediate will dye wool in acid bath a yellow color, like Naphthol Yellow S. The finished product diazotizes and couples to form val- uable dyes. 536,431—Mar. 26, 1895. M. Kaun and F. RunKxket, Germany. (Bayer.) Black dye. (Process also claimed.) 4.4’-Diamino diphenylamin 2’-sulfo. 1-Chlor 4-NITROBENZENE 2-Sulfo and 4-PHENYLENE DIAMIN are heated together in dil. alk. soln. and resulting nitro amino diphenylamin sulfo reduced. 536,524—Mar. 26, 1895. Wilhelm Herzsrerc, Germany. (Berlin.) Amidotriazin. (Process also claimed.) Amino triazins. Diamino azo BENZENE HCl (‘‘Chrysoidin’?) or other, and BENZALDEHYDE, etc., are heated in conc. HCl and acetic (1:4.5 parts) at 100°, diluted and pptd. by Na,CO,. Products are stable diazo comps. Sulfo acid may be formed by 3 to 6 parts fuming H,SO, (20 per cent anhyd.), at gentle heat for mono sulfo and at higher temp. for disulfo. 536,878—Apr. 2, 1895. R. Kircuuorr, Germany. (Berlin.) | Black dye. 4-Phenylene diamin azo cresidin. Diazo 4-NITRANILIN is coupled with crestpin (CH,.OCH,.NH,-4.1.2) and product reduced by alk. sulfids. 537,511—Apr. 16, 1895. Arthur WEINBERG, Germany. (Cassella.) Phenylamidonaphthosulfo acid. (Process also claimed.) Phenyl 2-amino 8-naphthol 6-sulfo. 2-AMINO 8-NAPHTHOL 6-sulfo ‘“‘Gamma’”’ and ANILIN HCl are dissolved in anilin and heated to 160°. Coupling test is made to determine end of reaction. 538,183—Apr. 23, 1895. Jakob Scumip and Johannes Mouter, Switzerland. (Basle.) Blue dye. (Process also claimed.) 1.2-Naphthoquinone 7-oxy 4-sulfo. 1-Nitroso 2.7-dioxy NAPHTHALENE is dissolved in cold bisulfite soln. to which conc. HCl is added to form 1-amino 2.7-dioxy NAPHTHALEND 4-sulfo, which is oxidized by HNO,. 539,699—May 21, 1895. M. Moeuier, Germany. (Berlin.) Blue dye. (Process also claimed.) 1-amino 8-naphthol 2.4-disulfo. I-NAPHTHYLAMIN 2.4-disulfo is sulfonated to trisulfo (1.2.4.8) then fused in NaOH to form naphthol deriv. 540,412-—June 4, 1895. Moritz Unricu and Johann BamMmann, Germany. (Bayer.) Amidonaphtholdisulfo acid. (Process also claimed.) 1-Amino 8-naphthol 3.6-disulfo “ey 7.2? I-NAPHTHYLAMIN 3.6.8-trisulfo obtained by nitration and reduction of NAPHTHALENE trisulfo, is fused with 2 parts NaOH at 180-190°, or higher temp., in open or closed vessels. Differences between acid of patent and of 458,285 are given in detail, For 1.8 dioxy acid, see 458,283. 541,750—June 25, 1805. W. Herzperc and O. Weser, Germany. (Berlin.) Black dye. 1-Amino 8-naphthol 3.6-disulfo disazo dianilin. 2-NITRANILIN, 2 mols. coupled in acid then alk. soln. with 1 mol. I-AMINO 8-NAPHTHOL 3.6-disulfo is reduced with Na,S. 330 DIGEST OF PATENTS 541,859—July 2, 1895. Richard Korerr, Austria-Hungary. (Kinzlberger.) New amido base and colors therefrom. (Dyes not claimed.) Tetra amino ditolidino methane. 2-TOLIDIN 2 mols., or other, in 66° H,SO, is condensed with 1 mol. 40 per cent FORMALDE- HYDE. Condensation product of 2-roLUIDIN is separated into two bases, § and L, by greater sol. of Na salt of latter in aq. and differs from product of Brack, 515,897 and 516,753, being a tetramino comp. united by two phenyl rests while Brack’s is diamino comp. united by two amino rests, etc. Note 543,712 for dye from above. §42,073—July 2, 1895. J. J. Bracx, Switzerland. (Durand.) Substantive cotton dye. (Process also claimed.) Probably two mols. dianisidin united by amino groups to form di-imino methane. DianisiDIN is boiled in dil. HCl soln. with FoRMALDEHYDE and base pptd. by ammonia. 543,894—Aug. 6, 1895. Rudolf ReyHER, Germany. (Bayer.) Azin dye and process of making same. Phenyl 3-toluylenediamin. 3-TOLUYLENE DIAMIN, or homologs, is heated in pressure vessel at 250-270° with 4 parts ANILIN, or homolog, and product purified and cryst. Note same process in 557,022 and 559,062 Group V. 546,604—Sept. 17, 1805. Johannes Tu1ELE, Germany, (Badische.) Amido-tetrazotie acid and process of making: same, Amino GUANIDIN, 1 mol., is mixed with soln. of 1 equiv. of mineral acid, diazotized below 40-45° and diazo salt recovered by crystn. Or to the soln. of diazo salt acetate or other weak alk., material is added in sufficient quantity to convert guanidin to acetate, and soln. evap. to dryness. 554,974—Feb. 18, 1806. Heinrich Baum, Germany. Process of making orthohalogenphenol. PHENOL is heated at 150° in closed vessel and vapor of Br or other halogen forced in. The resulting ortho deriv. contains but small amount of impurities that may be removed by addition of caustic alk. Fused with NaOH or KOH product gives pyrocatechin. 556,164—Mar. 10, 1806. C. Ris and C. Simon, Switzerland. (Geigy.) Gray dye and process of making same. Dialkyl 2-amino 8-naphthol 6-sulfo. 2-NAPHTHOL 6.8-disulfo ‘‘G” is heated in autoclave with ALKYLAMIN to 250° and the result- ing dimethylated amino comp. fused in alkalies above 200°, or 2-AMINO 8-NAPHTHOL 6-sulfo is alkylated. 563,382—July 7, 1806. Friedrich Krecxr and Ignaz RosEenserc, Germany. (Kalle.) Amidonaphtholdisulfo-acid “K.’? (Process also claimed.) 1-Amino 8-naphthol 4.6-di- sulfo “K.” NAPHTHALENE 1.5-disulfo stirred at 40° into sulfuric monohydrate containing o.2 parts of sulf. acid of 70 per cent anhyd., is heated to 80-90° to form trisulfo (1.3.5) then nitrated be- low 60°, reduced, separated as the acid and Na salt then fused in NaOH at 160-170°, Advan- tages of “K’’ over “H’’ acid given, and examples of azo dyes produced. : 564,801—July 28, 1806. Traugott SANDMEYER, Switzerland. (Geigy.) Greenish-blue dye. (Process also claimed.) 2-Sulfo benzaldehyde. 2-Chlor BENZALDEHYDE is heated in autoclave at 100—-200° with aq. sodium sulfite. 572,723—Dec. 8, 1806. Christian RupotpuH, Germany. (Oehler.) Trisazo dye. (Process also claimed.) 3-Amino phenol 6-sulfo acid III or 5-amino 2-cresol 3-sulfo acid III. ' ANILIN -3.4-disulfo, or 4-toluidin 3.5-disulfo, is fused with alkali. 574,395—Jan. 5, 1807. Robert W. Cornetison, New Jersey, and William H. Warren, New York. Process of obtaining aceto derivatives of aromatic amins. Acetanilid and homologs. GROUP XXII,—INTERMEDIATES Bot An acetic acid salt, preferably K or Na, and a salt of the amin with HCl or H,SO, in equimolecular quantities or with slight excess of acetate, are refluxed at 125° or other appro- priate temp. 574,396—Jan. 5, 1897. Robert W. CorneELison, New Jersey, and William H. Warren, New York. Process of obtaining aceto derivatives of aromatic amins. Acetanilid and homologs by less expensive process. Alkali acid salt of acetic acid with possibly a slight excess of acid is. heated at s50—-60° till dried, mixed with ANILIN or other amin, and refluxed at 100-125° for 12-24 hours. As acetan- ilid is formed the acetate returns to normal salt and absorbs excess moisture present. 575,237—Jan. 12, 1897. - Benno Homo.ixa, Germany. (Hochst.) Process of manufacturing aromatic aldehydes. Benzaldehyde and 2- or 4-nitro benzaldehyde, etc. Benzyl aniL1n or homolog or nitro deriv. in 5-10 parts aq. is raised to boil by live steam and o.5 bichromate with mineral acid slowly added. Aldehyde is recovered by distillation. 575,904—Jan. 26, 1807. J Christopher Ris, Switzerland. (Geigy.) Black azo dye. (Process also claimed.) 4.4’-Diamino ditolyl amin, or other. 4-TOLUYLENE DIAMIN, HCI salt, or other, oxidized with 2-toLuip1n HCI in cold aq. soln. by bichromate to an indamin, then reduced by Zn and HCl. 578,384—Mar. 9, 1807. Peter T. Austen and Herbert C. Tuttrr, New York. Process of making acetanilid, ete. Acetanilid mfr. using dilute acetic acid. ANILIN oil and 1.5 to 1.75 parts 50 per cent ACETIC acid are heated in autoclave at 150-160° and so lbs. pressure for 30 hours. Excess acid is preferable. 578,839—Mar. 16, 1897. Bruno R. SErFERtT, Germany. (von Heyden.) Process of making aromatie nitrosulfo chlorids. NITROBENZENE mixed with 2 parts CHLORHYDRIN sulfuric acid is heated by indirect steam until all HCl has been evolved, diluted with ice and filt. and nitrobenene sulfo recovered from mother liquor by converting to Na salt, which by treatment with chlorides of mineral acids forms further small quantity of nitrobenzene sulfo chloride. 587,75 7—Aug. 10, 1897. Ignaz RosENBERG and Friedrich Krecxrt, Germany. (Kalle.) Naphthylenediamin-sulfo-acid and process of making same. _1.3-Diamino mono-, di- or tri-sulfo naphthalene. 1-NaruTuor 3-sulfo, 1-naphthol 3.6-disulfo, 2.8-dioxy naphthalene 6-sulfo, or the 1.3.6-tri- sulfo acid, etc., is heated in autoclave with alk. and ammonia to 160—190°. : Note 588,180 Group VI. 593,347—Nov. 9, 1897. Fritz Benner, Germany. (Leonhardt.) Violet disazo dye. Ethyl 2-amino 5-naphthol 7-sulfo. Ethyl 2-NAPHTHYLAMIN HCl in conc. H,SO,, with fuming H,SO, (20 per cent SO,) at 40° gives two isomeric mono sulfo acids, one whose Na salt is soluble in alc., called ‘‘A,” and the other “B.”? More acid at 100-120° gives a disulfo acid which when heated with KOH at 200° produces above naphthol. Or 2-NAPHTHYLAMIN 5.7-disulfo is boiled with an1LIn to produce the phenyl deriv., then product fused at 210° in KOH. Note 521,095. 595,787—Dec. 21, 1897. Adolf Scumipt, Germany. Purification of crude acetic acid. Apparatus is shown whereby the impurities in crude acetic acid may be oxidized by the counter current principle. The warmed acid is introduced at the top of a tall cylindrical closed vessel filled with nut sized coal or coke, is distributed over the filter and meets a rising current of oxygen under pressure. 22 232 DIGEST OF PATENTS 595,897—Dec. 21, 1897. Henri R. Vina, France. Process of making paramidophenol. Paramino phenol by reduction process without loss of material. Oxy azo BENZENE or 2-nitro PHENOL or dinitro derivs., 2 parts, with 3 parts Na,S and 1 part NaOH, is heated to 180°. Presence of caustic prevents formation of by-products and loss. 596,043—Dec. 21, 1807. Carl von per Linpr, Germany. Process of distilling acetic acid. Pure colorless acetic acid, 65-85 per cent, free from sulfurous acid, acetone and empyreumatic products. Pyrolignite of lime is distilled with theoretical quantity of H,SO, in vacuum of not less than 600 mm. at a temp. such as 26° which is below that at which the acid attacks tarry matters and below decomp. temp. of acetate and acetic acid. Less material is used, purer and more conc. acid produced, brown acetate can be employed with sulfuric acid, time is saved and output of plant increased. 602,682—Apr. 19, 1808. Wilhelm Digrertt, Germany. (Hauff.) Process of producing orthotoluene sulfonie acid. Thio crEsoL is heated in alk. KMnO, (2.67 parts), until color disappears, then evap. to dryness. To oxidize still further and produce the benzene deriv. twice quantity of KMnO, is used and CH, removed by oxidation. 606,437—June 28, 1808. Fritz Benner, Germany. (Leonhardt.) Amidonaphtholdisulfo-acid and process of making same. 1-Amifo 8-naphthol 3.5-disulfo ‘‘B.” 1-AMINO 8-NAPHTHOL 3-Sulfo is further sulfonated in conc. sulf. acid at common temp. Heated in 6 per cent NaOH at 230° the dioxy comp. is formed. 606,470—June 28, 1808. Pierre P. Monnet, France. (Soc. Chim.) Process of making chlorin derivatives of tolaene. 2-Chlor benzylidin chloride, 2-chlor benzal chloride and other chlorin derivatives of toluenes ToLUENE 2- or 4-sulfo chloride is heated to 150-200° while stream of dry Cl gas is passed. The para compound yields much of the trichlor deriv., and is purified by distillation at 155— 165° under reduced pressure while the ortho comp. distils at 225-235° at ordinary pressure. A little PCl, aids chlorination. Product is used for making aromatic aldehydes, and acids. 607,056—July 12, 1898. Joseph Koetscuet, France. (Soc. Chim.) Process of making aldehydo-benzoie acid. (Product also claimed.) Naphthalene or deriv., is oxidized by KMnO, to 2-oxalyl BEnzorc acid and the latter after separation is warmed at 80-100° with 3 mols. ANILIN and resulting diphenyl diammonium phenyl imid deriv. refluxed in 5 parts xylene or other neutral solvent. CO, is evolved. 608,019—July 26, 1808. August BauscuiicHuer, Austria-Hungary. (Roessler-Hass.) Process of and apparatus for making acetone. Apparatus is shown in which dry acetate of lime (acrric acid, Ca salt) and 5 per cent Ca(OH), are treated with superheated steam, acetone vapors condensed and rectified under pressure. 613,460—Nov. 1, 1898. Pierre P. Monnet, France. (Soc. Chim.) Process of making aromatic aldehydes. Aromatic aldehydes by direct oxidation of side chain. TOLUENE, homolog or deriv., and 2.5 parts 65 per cent H,SO, are mixed and 0.3 parts powd. MnO, slowly added *t about 40°, so that large excess CH, compound is always present. 616,123—Dec. 20, 1808. Ivan Levinste1n and Carl MeEnscurnc, England. (Levinstein.) Process of making alphylamidonaphthol-sulfonie acids. Phenyl 1-amino 8-naph- thol 6-sulfo. 1.8-Dioxy NAPHTHALENE 6-sulfo “G’” is heated to 160° with anitin HCl and ANILIN, or homolog. GROUP XXII.—INTERMEDIATES 333 618,688—Jan. 31, 1890. Ernst Konic and Franz Scuoit, Germany. (Hdéchst.) Aromatic amidoammonium base and process of making same. 3-Amino pheny) trimethyl ammonium base that forms stable diazo comp. 3-Nitro PHENYL trimethyl ammonium chloride is reduced by Zn and HCl or other to amino compound that is stable and may be diazotized and coupled with amins and phenols to form basic azo dyes. 618,809—Jan. 31, 1809. Henry R. Vipat, France. Process of making amidophenols. SULFANILICc acid, or other aromatic amino sulfo acid, is mixed with 0.8 part MnO, to which 3.5 parts 66° H,SO, is added and temp. raised to 60°. When reaction starts, outside heat is removed. After dissolving in aq. and removing Mn. the product crysts. from cooling soln. 619,181—Feb. 7, 1809. Max H. Ister, Germany. (Badische.) Product from dinitro-naphthalene and process of making same. Dinitro naphthalene deriv. for mfr. of various types of brown, red or yellow dyes. 1.8 Dinitro NAPHTHALENE or (1.5 deriv.) in 5 parts fuming sulf. acid (12-23 per cent anhyd.) is heated at 40-50° until sol. in NaOH with yellow color. Product can be converted by treatment with fuming (40 per cent $O,) H,SO, in presence of sulfur to a sol. brown YELLOW acid mordant (Cr) dye fast to light and milling. With sulfuric and boracic acids BROWN to RED dyes are obtained. On reduction a base that may be used for azo dyes results. 620,368—Feb. 28, 1890. Jakob Scumip, Switzerland. (Basle.) Blue tetrazo dye and process of making same. 1.8-Naphthacetol 3.6-disulfo, or isomers. I-AMINO 8-NAPHTHOL 3.6-disulfo, heated to a boil in mixture of glac. acetic acid, acetic an- hyd., and anhyd. sod. acetate until no longer diazotizable. Diacet amino naphthol disulfo is formed as by-product but may be transformed into above by boiling in dil. acid or alk. 622,854—Apr. 11, 1899. Benno HomoiKa and August Stock, Germany. (Hochst.) Nitrobenzyliden sulfonic acid and process of making same. 2- and 4-Nitro benzylidene anilin sulfo acids for production of nitro benzaldehyde, etc. 2- or 4-Nitro benzyl aniL1In sulfo, Na salt, is oxidized in aq. soln. with KMnO,, or other, preferably in presence of CO, or MgSO,, while cooling and stirring. Products which exist only as salts decompose completely in aq. or dil. acid soln. to nitro benzaldehyde, etc. 625,174—May 16, 1889. Ivan Levinste1In and Herman Preirrer, England. (Levinstein.) Substantive red tetrazo dye and process of making same. Dichlor diacet benz- idin. Diacet. BENzIDIN is dissolved in conc. sulf. to which sufficient Ca(OCl), is added to form dichlor benzidin, then saponified by boiling in dil. HCl. Or diacet. benzidin is suspended in salt soln., a little Fe wire added as carrier and chlorin gas passed in. 625,637—May 23, 1890. Heinrich Berntusen, Germany. Oxynaphtindophenolthiosulfonice acid and process of making same. as-Dimethyl 4-PHENYLENE DIAMIN thio sulfo and 1-amino 2-naphthol 6-sulfo, in aq. soln. are made just neut. with NH,OH and at 12-15° a 24 per cent soln. of FeCl, is added. Nitroso naphthol or dioxy naphthalene derivs. may be used and other oxidizing agents. BLUE (Cr) to violet puuE (Al) acid mordant dyes fast to light and washing and adapted to printing. 628,025—July 4, 1899. Carl OFHLSCHLAEGEL, Germany. (Berlin.) Blue-black wool-dye and process of making same. 4’-Amino 2’-sulfo phenyl 2- naphthylamin. 4-Nitro chlor BENZENE 2-sulfo, heated for 12 hours at 160-170° in closed vessel with 1 mol. 2-NAPHTHYLAMIN and a carbonate to absorb acid, reduced by HCl and Fe or Zn, etc., and pptd. as Na salt. 628,5038—July 11, 1890. Ernst TwitcHELL, Ohio. Fatty aromatic sulfo compound and process of making same. Sulfo fatty aro- matic acids such as sulfo benzene stearic acid, C,H,(HSO,)C,,H,,0,, etc., stable catalyzers for hydrolysis of fats and oils. 334 DIGEST OF PATENTS OxeErc acid or other fatty acid is mixed with 40 per cent of an aromatic comp. such as naph- thalene, bénzene, phenol, etc. and excess conc. H,SO, added below 30°. After standing, the conjugated sulfo comp. is freed from excess acid, naphthalene, or similar sulfo derivs. 628,607—July 11, 1899. Bernhard Prigss and Oskar KaitwassEr, Germany. (Berlin.) Blaek dye. 4’-Oxy 2-nitro 4-sulfo diphenylamin. 2-Nitro 1-chlor BENZENE 4-sulfo in aq. soln., is heated in closed vessel for two hours at 140°, with 1 mol. 4-amino PHENOL and a tarbonate. 629,748—July 25, 1899. Ivan Levinsterin and Richard Herz, England. (Levinstein.) Blue-black disazo color and process of making same. Acetyl 1.4-naphthalene diamin 6- or 7-sulfo. ANILIN, coupled with 1-NAPHTHYLAMIN 6- or 7-sulfo, reduced as paste with Fe and acetic, is made alk., filt., and pptd. by slight excess acid, dried, powd., and acetylated by refluxing with 65 per cent acetic acid and sod. acetate. Acetylation may take place before reduction of azo dye. 631,606—Aug. 22, 1809. Oscar Batty, Germany. (Badische.) Halogen derivative of anthraquinone and process of making same. Halo- genated alphyl diamino anthraquinones. I.5-DINITRO ANTHRAQUINONE or crude dinitro anthraquinone, boiled in 10 parts ANILIN or other primary aromatic amin to alphyl amino product, is brominated (or Cl) in CS, or glac. acetic acid. Product condensed with an amin forms a dye that may be sulfonated. Table of reactions of various products is given. 631,607—Aug. 22, 1899. . Oscar Batty, Germany. (Badische.) Dibrom anthraquinone derivative and process of making same. Dibrom 1.5-diamino anthraquinone. Diamino ANTHRAQUINONE is suspended in 20 parts glac. acetic to which 2 parts Br are added at ordinary temps. A brick red powd., which crysts. from toluene in brown leaflets, diff. *sol. in alc. and glac. acetic, more readily in C,H,CH,, C,H, and C,H,NO, (YBr). 631,608—Aug. 22, 18099. Oscar BatLy, Germany. (Badische.) Anthraquinone derivative and process of making same. _ Tribrom 1.5-diamino anthraquinone. 1.5-Diamino ANTHRAQUINONE dissolved in 150 parts boiling glac. acetic acid, 2 parts Br added and soln. boiled until HBr ceases to evolve. A brown powd. or cryst. needles, diff. sol. cold alc., giac. acetic, CH, and C,H NO: Addition to 631,607, and note 632,621 for derived dye Group III. 634,009—Oct. 3, 1890. Ivan LEvINSTEIN and Richard Herz, England. (Levinstein.) Blue-black tetrazo dye and process of making same. _ 1.4-Naphthalene diamin 2-sulfo. ANILIN is coupled with 1-NAPHTHYLAMIN 2-sulfo, filt., dye reduced by Fe and HCl, soln. neut. by carbonate, anilin distilled off, and sulfo acid pptd. by HCl. 636,043—Oct. 31, 1809. Benno Homo.ixa and August Stock, Germany. (Hochst.) Process of obtaining nitrobenzylanilin. 2- or 4-Nitro TOLUENE chlorinated up to 50 per cent of w-chlor deriv. is mixed with equi- mols of ANILIN or homolog, and heated to 85-90°, when reaction starts temp. rises to 120-180° according to anilin base employed. Anilin HCl that forms as by-product is removed by boiling aq. and nitrotoluene in excess is distilled off. Other halogens may be used and part of anilin be replaced by alk. or alk. earth salt or NH. Note 636,994. 636,994—Nov. 14, 1899. Benno Homo.ika and August.Stock, Germany. (Hochst.) Process of obtaining ortho and para nitro benzaldehyde. 4-Nitro BENZYLIDENE sulfo, or ortho comp., Na salt, made as described in 636,043, is neut. in aq. soln. by HCl and the free acid thus liberated decomposes at once into 4-nitro benzalde- hyde which ppts., leaving anilin sulfo acid or homolog in soln. Or to original benzylidene comp. is added a soln. of 1 mol. anilin or other primary amin and separated 4-nitro benzylidene-anilin is boiled in dil. mineral acid. GROUP: XXII.—INTERMEDIATES 335 637,183—Nov. 14, 1899. Henry Trrrisse and Georges Darier, Switzerland. (Badische.) Yellow basic dye. 2.4-Diamino 5-methyl toluyl alcohol. 3-TOLUYLENE DIAMIN mixed in aq. soln. with FORMALDEHYDE at usual temp. 640,564—Jan. 2, 1900. Benno Homoika and August Stocx, Germany. (Héchst.) Process of making amidobenzaldehyd. 2-Amino BENZYLIDENE anilin sulfo acid or homolog is distilled with steam. Resulting 2-amino BENZALDEHYDE is carried over while anilin sulfo remains in soln. The corresponding para benz- ylidene comp. preferably is treated with bisulfite and aldehyde retained in soln. while anilin is distilled over because para comp. is not volatile with steam. 640,989—Jan. 9, 1900. M. Bonicer, Switzerland. (Sandoz.) Blueish-red azo dye. Alphyl 1-sulfamino 8-naphthol 3.6-disulfo or other. I-AMINO 8-NAPHTHOL 3.6-disulfo or other dissolved at 70° in aq. containing chalk and to this mixture is added 4-roLvENE sulfo chloride, or other, temp. raised to 80° until diazo test reaction fails, then boiled and NaOH added to split off alphyl sulfamino radical from hydroxyl group. The alphyl sulfamino group attached to NH, group is unchanged. Soln. is neut. with HCl and pptd. by Na,CO,, etc. 641,100—Jan. 9, 1900. Hermann Gussmann, Germany. (Hochst.) Process of making para-oxy-para-amido-ortho-oxydiphenylamin. 2.4’-Dioxy 4-amino diphenylamin. 4-Nitro chlor BENZENE 2-sulfo, is heated in sod. acetate soln. in closed vessel at 120° with 4-amino PHENOL to form 4’-oxy 4-nitro DIPHENYLAMIN 2-sulfo, which is reduced, then heated in strong alkali at 150-200° and pptd. by acid. Gray white needles, sol. in hot aq. 644,235—Feb. 27, 1900. P. Juuius, Germany. (Badische.) Black disazo dye. 2-Nitro 4-amino phenol 6-sulfo. 4-Amino PHENOL 6-sulfo is dissolved in 95 per cent sulfuric, cooled to 5°, and mixture of HNO, and sulfuric monohydrate added below 0°. 644,236—Feb. 27, 1900. P. Juuius, Germany. (Badische.) Black disazo dye. 4-Nitro 2-amino phenol 6-sulfo. 2.4-Dinitro PHENOL 6-sulfo in dil. KOH soln. is reduced by Na,S below 20°. 644,239—Feb. 27, 1900. P. Jutius, Germany. (Badische.) Black disazo dye. 2-Chlor 6-amino phenol 4-sulfo. 2-Nitro 6-amino PHENOL 4-sulfo is diazotized and diazo comp. chlorinated in HCI soln. with “molecular” copper (Gatterman), then reduced by Fe and acetic. 644,331—Feb. 27, 1900. Eugen Sapper, Germany. (Badische.) Process of making phthalic acid. NAPHTHALENE, I part in 15 parts sulfuric (100 per cent) and o.5 pts. HgSO,, is warmed until dissolved, then heated in retort gradually to 200° (reaction begins) then more rapidly to 250° (SO, and CO, evolved) then to 300° or higher until solid or viscous. . Distillate consists of dil. sulf. acid and phthalic anhyd. with some sulfo phthalic. Filter or centrifuge. Other original materials derived from naphthalene nucleus are claimed and proportions of ingredients given. 647,237—Apr. 10, 1900. F. Scumipt, Germany. (Hochst.) Diamidodiphenylamin sulfonic acid and process of making same. = 4.4’/-Di- amino diphenylamin 2.2/-disulfo (or 4.4’.2.3’ deriv.) 4-PHENYLENE DIAMIN 2-sulfo is refluxed with 4-nitro chlor BENZENE 2-sulfo in dil. alk. carb. soln., pptd. by acid and reduced with Fe and acetic, filt. and re-pptd. by acid. 648,261—Apr. 24, 1900. Benno Homo.ixka and August Stock, Germany. (Hoéchst.) Nitrobenzylanilin sulfonic acid and process of making same. 2- or 4-Nitro BENzyL chloride and aniLin sulfo or homolog in dil. Na,CO, soln. are heated at 60-100°. Or a mixture of nitro benzyl chloride with nitro toluene obtained by partial chlor- ination of the latter may serve as first component. Other alkaline reagents may be used. 330 DIGEST OF PATENTS 648,389—May 1, 1900. Harry O. Cuurts, Canada, Process of making acetone. Apparatus is shown and described whereby acetates or other salt of fatty acid, in finely divided state or in thin layers or films are subjected to the exact temp. to liberate ACETONE or other ketone which is simultaneously removed from hot alk. mass to prevent decomp. A cir- culating pump keeps reaction chamber free of acetone, a vacuum being maintained or steam or any oxygen free gas passed through. 648,753—May 1, 1900. Paul Jutius, Germany. (Badische.) Blue-black sulfur dye. 4’.4”-Dioxy 3'.3”-dicarboxy diphenyl 4.6-dinitro 1.3-phenylene di- amine. 4.6-Dinitro 1.3-dichlor BENZENE, 1 mol., is refluxed in aq. soln. with 2 mols. amino SALICYLIC acid and enough sod. acetate to bind liberated mineral acid. 648,754—May 1, 1900. Paul Jutius, Germany. (Badische.) Green-black sulfur dye. 4/.4”-Dioxy 3’.3”-disulfo diphenyl 4.6-dinitro 1.3-phenylene diamin. 4.6-Dinitro 1.3-dichlor BENZENE, is refluxed in aq. soln. with 2 mols. 4-amino PHENOL 2-sulfo and sufficient sod. acetate to bind mineral acid. 648,755—May 1, 1900. Paul Jutius, Germany. (Badische.) Black sulfur dye. 4'.4”-Dioxy diphenyl 4.6-dinitro 1.3-phenylene diamin. 4.6-Dinitro 1.3-dichlor BENZENE, is refluxed in alc. soln. with 2 mols. 4-amino PHENOL HCl and sufficient sod. acetate to bind mineral acid. 649,714—May 15, 1900. Johann BAMMANN and Walter Vorster, New York. (Elberfeld.) Dinaphthylamin sulfo derivative and process of making same. _ 5.5’-Dioxy 2-dinaphthylamin 7.7’-disulfo. 2-AMINO 5-NAPHTHOL 7-Sulfo, is heated to 80-100° in strong alk. soln. with bisulfite, 2 mols. condensing to dinaphthyl comp. Note 656,620 and 21 employ above as intermediate Group VI. 650,327—May .22, 1900. Paul Junius and Friedrich Revsoip, Germany. (Badische.) Black sulfur dye. 2.4-Dinitro 5-amino 4’-oxy diphenylamin. 4.6-Dinitro 1.3-dichlor BENZENE, is refluxed in alk. soln. containing sod. acetate with 1 mol. 4-amino PHENOL, and the isolated 2.4-Ginitro 5-chlor 4’-oxy DIPHENYLAMIN heated in alc. NH, at 150—-160°. ‘ 650,332—May 22, 1900. Max Manpt and Robert HotpMann, Germany. (Badische.) Process of oxidizing orthonitrotoluene. 2-Nitro benzaldehyde or 2-nitro benzoic acid made by regulating conditions of same process. 2-Nitro TOLUENE in 10 parts 35-48 per cent H,SO, is mixed with 2 parts MnO, and heated 4n pressure vessel at 140-165° for 2-3 hours at not more than 10 atms. to produce 2-nitro benz- aldehyde. For the benzoic acid deriv. stronger acid (62-78 per cent) and temp. of only 135- 145° should be used, and pressure vessel is not necessary. y L 2 2 692,863—Feb. 11, 1902. Joseph Korrscuet, France. (Soc. Chim.) 4 Substituted sulfinid and process of making same. (Product not claimed.) 4-Amino benzoic sulfinid produced directly from 4-nitro toluene sulfamid. 4-Nitro 2-TOLUENE sulfamid is dissolved in 10 parts of aq. containing 6.45 per cent sulfur and 12.9 per cent NaOH, boiled some hours, made acid, and ppt. extracted with ether. GROUP XXIV.—FINISHED PRODUCTS OTHER THAN DYES 447 714,931—+4ec. 2, 1902. Georg Merrutinc, Germany. (Hochst.) Hydrobenzaldehyde and process of making same. 2-Iso propyl 4-methyl hexahydro benzaldehyde, or other. Hydro BENZYL amin bases are transformed by oxidizing agents into hydrobenzylidine comps. that are decomp. by heating with acids. Patent gives reactions in extended detail. 743,305—Nov. 3, 1903. Georg Mertinc and Robert Wetpr, Germany. (Hochst.) Trimethyl-cyclohexenoncarboxylic-acid ester and process of making same. A parent material for perfumes. Ethyl ester and iso propylidene ethyl ester of aceto acetic acid, 1 mol. each, are condensed in alc. soln. by means of 1 atom metallic Na. by standing several weeks at low temp. Sod. ethyl carbonate separates, soln. is neut. with dil. H,SO,, alc. distilled off in vacuum and ester re- maining as layer of oil extracted with ether, dried, rectified, etc. 804,682—Nov. 14, 1905. Rudolf J. M. Sommer, Austria-Hungary. (Fritzsche.) Process of making protocatechuic aldehyde. Material for mfr. of vanillin, etc. HELIOTROPIN in alc. soln. mixed with excess NaHSO, and aq. is heated under pressure of not more than 12 atms. and below 190°. Variations of method are given. 1,329,272—Jan. 27, 1920. Elnathan K. Netson, Maryland. (U. S. Govt.) Vanillyl amin, vanillyl, acyl amid, and production thereof. _ VANILLIN in alc. soln. is treated with NH,OH.HCl and Na,CO, in warm place 24 hours, ale. evapd., aq. added to ppt. vanillin oxim which in alc. soln. is reduced with sod. amalgam while glac. acetic is slowly added to maintain acid reaction. To 2 mols. of purified vanillyl amin (dried at 110°), suspended in dry ether, 1 mol. acyl chloride is added, heated gently, aq. and HCl added and soln. extracted with ether, which is washed with dil. Na,CO, and evapd. Amids may be formed from a large number of organic acids, acid chlorides and acid anhydrides. 1,5345,649—July 6, 1920. Andre Weiss, France. (Soc. Chim.) Process for the manufacture of oxyaldehydes and of their ethers. Vanillin or 2-anisol 4-aldehyde, or other. GUAIACOL, or other aromatic oxyaldehyde, is mixed with FORMALDEHYDE in mol. proportions in alc. soln., alc. HCl and 0.5 mol. 4-nitroso dimethylanilin added, then heated at 100° several hours while HCl gas is bubbled through soln. Soln. is cooled, made alk. with dil. NaOH so that 4-amino dimethylanilin may be removed with ether, etc., then made acid and vanillin ex- tracted by ether, etc. 1,372,434—Mar. 22, 1921. Jacob M. Jouztin, New York. (Semet-Solvay.) Process of forming diphenyl oxid. Diphenyl oxide made in one operation. BENZENE sulfo, Na salt, and about 60 per cent of alkali required to combine with all the sul- fonate, is heated in closed vessel until aq. ceases to form then heated at 420° to condense tesidual sulfonate with phenate to form diphenyl oxide, which distils off. 1,418,904—June 6, 1922. Florentin Bripaup, France. (Soc. Chim.) Process for the manufacture of aromatie oxaldehydes. Vanillin from guaiacol. GuAIACOL, with 2.5 parts METHYLAL (dimethyl glycol) and nitroso DIMETHYL ANILIN derived from 2 parts dimethylanilin, in 12.5 parts methyl alc. are heated at 100° for 1-2 hours while HCl gas is bubbled through soln. Alcohol is removed by distillation and vanillin extracted from residue with benzene or ether, and purified. Methylene chloride, sulfate, diacetate or other, can replace methylal. 1,427,400—Aug. 29, 1922. Chauncey C. Loomis, New York. (Semet-Solvay.) Process of producing salicyl aldehyde. Saticyiic acid, 10 parts, is warmed with 8 parts borax, 10 parts boric acid and 3o parts aq. to form acid sod. boro disalicylate, cooled to 15° and 20 parts NaHSO, added with stirring and cooling. Fifty parts 10 per cent sod. amalgam are then added at 15°, Hg separated and soln. evap. to cryst. salts., filt., 200 parts aq. added and aldehyde distilled off. When formed in presence of excess alk. sulfite the sulfite addition product prevents decomp. of the aldehyde. 448 DIGEST OF PATENTS SUBGROUP (m).—MEDICINALS. 254,098—Feb. 21, 1882. Wilhelm PickHarpt and Hermann ENDEMANN, New York. Manufacture of chinoline. Purification of crude quinolin. QUINOLIN, crude, prepared according to Skraup pat. 241,738 is pptd. as tartrate, filt. base freed by alkali, distilled with steam and dried. It is colorless when exposed to air in soln. Addition to 241,738 (Gr. XXII.). 273,498—Mar. 6, 1883. Otto Fiscuer, Germany. (Hdchst.) Process of preparing oxyhydro ethyl chinoline. (Product also claimed.) QUINOLIN is converted to mono sulfo acid by heating at 100° in fuming H,SO,, neut. with lime, converted to dry Na salt, which is fused in 2-3 parts NaOH until converted to Na salt of oxy-quinolin and product thrown out of diluted melt with excess HCl. Two isomeric alfa and beta oxy quinolins are sepd. by crystn. from aq. The oxy hydro and alkyl derivs. are derived by usual methods of reduction with Sn and HCl and treatment with alkyl halides. 276,796—May 1, 1883. Otto FiscuHer, Germany. (Hochst.) Preparation of oxyhydro-methyl chinoline. (Product also claimed.) Oxy methyl quinolin. QuUINOLIN sulfo is converted to 1-oxy deriv. as in 273,498 and this is heated with 1 mol. METHYL iodide to form hydriodide of 1-oxy methyl quinolin, which base is pptd. by NaOH. 282,488—Aug. 7, 1883. Alexander BOuHRINGER, Germany. Method of producing monalecylised hydro-bases. Methyl hydro quinolin base. QUINOLIN, lepidin or other tertiary base is condensed with METHYL chloride to form chlor methyl quinolin, then reduced to methyl hydro quinolin base. 295,825—Mar. 25, 1884. Zdenko H. Sxraup, Austria-Hungary. (Badische.) Manufacture of parachinanisol. (Product, not process, claimed.) Parachinanisol. 4-Amino ANISOL and o.8 parts 4-nitro ANISOL, nitrobenzene, or similar nitro compound are refluxed with 5 parts GLYCERIN and 2.8 parts H,SO, (1.848) at 140-155°, and product recovered by distn. with steam from alk. soln. 307,399—Oct. 28, 1884. Ludwig Knorr, Germany. (Berlin.) Preparation of dimethyl-phenyl-oxypyrazol. (Product, not process, claimed.) Dimethyl phenyl oxy pyrazol, m.p. 115°. Aceto ACETIC ester is condensed with 1 mol. PHENYL hydrazin then heated to 1c0-150° whereby alcohol is eliminated, again heated with methyl chloride, etc., to form the dimethyl deriv. 318,662—May 26, 1885. Ernst W. R. ScHrOTER, Germany. Topical remedy. Ichthyol sulfonic acid. Oils containing sulfur in natural combination, such as schist oil, are sulfonated in 3 parts conc. H,SO, Product can be further sulfonated. 322,940—July 28, 1885. Theodor Krempr, Germany. (Chem. Fab.) Manufacture of iodoform, bromoform, and chloroform. ALCOHOL, aldehyde or acetone, is treated with potassium iodide or other alkali or alkali earth halide to form iodoform, chloroform, or bromoform. 343,803—June 15, 1886. Constantin FAHLBERG, New York. Medicated benzoic sulphinide compound. (Process also claimed.) Benzoic sulfinid compounded with organic alkaloid to neutralize bitter taste of alkaloid. Quinine, or other alkaloid is neutralized in alc. or aq. soln. with BENzoIc sulfinid to form a salt neutral to litmus. . Note 319,082 (Gr. XXIV f.) 428,286—May 20, 1890. Carl Paar, Germany. (Kalle.) Phenyldihydroquinazoline. 2-Nitro benzyl ANILIN* is refluxed with 20 parts conc. FORMIC acid or treated in benzene soln. with sodium formanilid to form 2-nitro BENZyL formanilid which is reduced in alc. soln. with Sn and HCl. The SnCl, double salt, the HCl, the base and derivs. are claimed. * For preparation of anilin comp. see Lellmann and Stickel, Ber., 19, 1604. CS EO ig) ee PPL aie GROUP XXIV.—FINISHED PRODUCTS OTHER THAN DYES 449 464,861—Dec. 8, 1891. Gustav Expert, Germany. (Hochst.) Process of making phenylethylmethylpyrazolone. (Product also claimed.) Phenyl ethyl PyRAZOLONE with equal part ETHYL iodide is heated in enameled vessel under pressure to 150° for 12 hours, purified and HCl salt formed. Product is sol. in usual solvents, except ligroin, deliquesces, with nitrous acid gives nitroso comp., with FeCl, a double salt (R). It is a homolog of antipyrin and may be used like this as a medicine. 466,70S—Jan. 5, 1802. Josef ZrEGLER, Germany. (Lembach.) Process of preparing oxychinoline sulphate. 2-Amino PHENOL 4-sulfo and equimol. 2-nitro PHENOL 4-sulfo are refluxed with GLYCERIN and H,SO, (60°), diluted and product pptd. by soda distilled with steam and again refluxed with 2 mols. dilute H,SO, (66°) then distilled in vacuum. 492,868—Mar. 7, 1893. Hermann JanssEN, Germany. (Bayer.) Salicylic-acid compound. (Process also claimed.) Acetyl 4/-amino phenyl salicylic acid. 4'-Nitro phenyl saLicyLic acid is reduced with Sn and strong HCl in presence of alcohol. H,SO, (60°), diluted and product pptd. by soda, distilled with steam and again refluxed with H,S to remove Sn, soln. pptd. by Na,CO,, ppt. sepd. and acetylated. 495,124—Apr. 11, 1893. Adolf SprecEL, Germany. Sulphur compound. (Process, not product, claimed.) Ichthyol sulfonic acid. Mineral oil distillate is purified by alk. and acid, residue treated with fuming H,SO, (10 per cent SO,), soluble portion pptd. by salt and purified from sulfones, etc. 501,235—July 11, 1893. Bruno R. Se1Fert, Germany. (von Heyden.) Creosote compound. Carbonic acid ethers of creosote. CREOSOTE is dissolved in alkali and treated with PHOSGENE, or is heated with ethers of car- bonic acid, or the carbonyl chloride of creosote is treated with creosoted alkali. 503,066—Aug. 8, 1893. Hermann Tuoms, Germany. Salicylate of para-tolyldimethylpyrazolon. (Process also claimed.) 4-Tolyl HyDRAzIN is heated with acetic ether, then with methyl iodide and methyl alcohol to form 4-tolyl dimethyl PyrazoLonr which is melted with saLicyLic acid. 503,748—Aug. 22, 1893. Leonhard LEDERER, Germany. (Boehringer.) Amido-crotonylanilid and process of making it. Acetyl acetanilid is treated with NH,. 512,590—Jan. 9, 1804. Gerhard N. Vis, Germany. (Dahl.) Orthooxyethyl-alpha-benzoylamido-quinolin. (Process also claimed.) Benzoyl s-amino 8-ethoxy quinolin,* m.p. 208°. 5-Amino 8-ethoxy QUINOLIN is boiled with 2 parts BENzZoyL chloride, mass boiled with aq. and'NH, added. Or these are mixed cold in dil. NaOH to fix HCl set free, then NaOH in excess added until odor of benzoyl chloride disappears. 513,204—Jan. 23, 1894. Ernst W. R. ScHrotrer, Germany. (Cordes.) Process of making pure sulfonin compounds. Purifying ichthyol sulfo acid and other sulfo comps. from mineral oils. Soln. of crude sulfo acids from mineral oils made as in 318,662 is acidified with HCl until color becomes paler. The desired sulfo acids crystallize and settle to bottom of liquid, are separated and purified by recrystn. 533,718—Feb. 5, 1895. Jacob Meyer, Germany. (Bayer.) Tannin compound. (Process also claimed.) Acetyl and diacetyl gallic acid. ; Dry TANNIN is mixed with 0.5 parts glac. acetic and 1 part acetic anhyd. and heated at 130-140° from 6-7 hours, then poured in thin stream into aq. and stirred to convert into light yellow powd. Instead of tannin other gallic derivs. and for acetic anhyd. other acid anhyd. may be employed. * For description see J. prak. Chem., new vol., 45, 541. 450 DIGEST OF PATENTS 537,841—Apr. 23, 1895. Joseph F. von Merino, Germany. Process of making ethers of paraoxyphenylurethane. (Products also claimed.) Acidyl derivs. of 4-oxy phenyl ethyl urethane. 4-Oxy phenyl ethyl URETHANE mixed with acetic anhyd. is heated under pressure. Glac. acetic or acetyl chloride may replace the anhyd. and propionyl and other acidyl derivs. are also claimed. 541,489—June 25, 1895. Joseph F. von Merrine, Germany. Acidyl compound of para-oxyphenylurethan ethers. (Process also claimed.) Acidyl derivs. of esters of 4-oxy phenyl ethyl urethanes. Process is similar to 537,841 using 4-oxy phenyl ethyl URETHANE esters as materials to be acidylated. 543,214—July 23, 1895. Wilhelm Mayert, Germany. Aromatic glycocol derivative. (Process also claimed.) Glycocol amids. ACETANILID is digested 12-24 hours at 50-60° in 25-30 parts strong alc. NH,, solvent re- covered and residue in aq. soln. with excess NH, gives cryst. glycocol anilid. Halogen comps. of acetanilid, etc., and substituted ammonias, such as DIMETHYL amin, glycocolethers and amids, or acetyl toluidin, anisidin and phenetidin derivs., etc., may be employed. 543,579—July 30, 1895. Leonhard Lreprerer, Germany. Process of producing phenoxacetic anilids, &c. Phen oxal acet 4-phenetidid and re- lated comps. Phen oxal acetic acid and 4-PHENETIDIN in equimols. are heated at 120-140° until no more aq. is given off. Residue is cryst. from boiling alc. List of comps. (21) with properties is given. 563,116—June 30, 1896. Josef ZiecLteR, Germany. (Fritzsche.) Process of making quinolin compounds. 2-Oxy quinolin pyrosulfate, K salt, an anti- septic comp. 2-Oxy QUINOLIN dissolved in 5-6 parts boiling alc. is refluxed with 1 mol. pulv. K,S,O, (pyrosulfate) for 10-12 hours. 563,993—July 14, 1896. Gustav A. WELTER, Germany. (Kuchler.) Amidoalkylsalicylic acid. (Process also claimed.) 5-Amino and acetyl 5-amino salicylic acid. Ethyl saticyiic acid is treated with HNO, (1.2), or preferably with mixed acids, to form s-nitro SALICYLIc acid which is separated and digested at roo° with HCl and Sn until dissolved, evapd. to dryness, Sn removed from aq. soln. of residue and evapd. to crystn. The acetyl deriv. results when glac. acetic acid and Sn are used for reduction. 567,968—Sept. 22, 1896. Arthur E1rcHencrttn, Germany lodoform combination with hexamethylenetetramine. Cryst. inodorous surgical compound which decomp. to give free CHI,. HEXAMETHYLENEAMIN is heated at roo° with equimol. CHI, in abs. alc. Phenol, chloral, alkyl iodide or other derivs. of hexamethylene tetramin in alc., chloroform or amyl acetate solns. may be employed. 569,416—Oct. 13, 1806. Oscar Hinsserc, Switzerland. (Hochst.) Ester of alkoylaminophenols and method of making same. Acetyl! ethyl 4-amino phenyl ethyl carbonate, etc. Acetyl ethyl 4-amino PHENOL dissolved in calculated quantity of NaOH is treated with slight excess ETHYL chlor carbonate, shaken well and cooled until reaction is complete. Other i alkoyl amino phenyl carbonic esters are claimed. 579,412—Mar. 23, 1897. Friedrich Stoiz, Germany. (Hochst.) Pyrazolon compound and process of making same. Phenyl 2.3-dimethyl dimethyl 4-amino pyrazolone, m.p. 107—108°. Phenyl 2.3-dimethyl 4-amino PYRAZOLONE is heated at 90° with equal parts alcohol and 2 mols. METHYL iodide for 1 hour; alc. distilled off and product extracted from its alk. soln. with benzene. Product is white cryst. comp. sol. in usual solvents except ligroin. Bregeat) Corporation of “America a6 sea cee eee Wilmington, Del. i British Alisarin’ Co Lid. f.i.%sscu le Oe on ee oe Manchester, England. British Dyestuffs Corp., Ltd...) 4.5.06 +0) pile elcp a uee London, England. Bronner, vormals Farbenfabrik Frankfort, Germany. > Brooke, Simpson’& Spiller iii. . Uae lek eee ee ee cue eee ee London, England. 2 Brown, William (Morgan (i500 859. Sa eae eee London, - England. iE Brugge, A. G., (Chemische Fabrik, vormals Dr. Zimmermann % & COD Wisc esp Bieves cue m eraee b pustaeca aves ince tacts lente aire oe ae Brugg, Switzerland. Me Bunnell, M:. Dick sige vist whisis aces cela dina ae ale ae et San Francisco, Cal. ff Burtnett, Abraham Garrison 6.030.550 0s nckot soon eee Lait Bronxville, N. Y. * Butterworth-Judson Corp. ........eccceevees PEE i ue, ate New York, N. Y. = 43 Cassella & Co., Leopold ............ ahd sig pips wo Rep epee ne Frankfort, Germany, % and New York, N. Y. te Carter, Dinsmore: & Cow cin ciiseice-as swab © 4s cel balou ane Brooklyn, N. Y. ig Celluloid Manufacturing Co. ie. ses sic ois) sienielal see reteousivereeanee New York, N. Y. Chadeloid.: Chemical. (Go. 0 yim acc aw coke ais os arereeie lei cetera e ee West Virginia. Chanee & Hunt, Ltd. (Alfred F. Holly and Owen E. Mott.) .... Oldbury, England. Chemical Development Or See Ere AC A oo Augusta, Maine. Chemische Fabrik auf Actien, vormals E. Schering ............ Berlin Germany. Chemische Fabrik, vormals Sandoz. See Sandoz. Chemische Fabrik von Heyden Actiensgesellschaft. See won Heyden. ASSIGNEE INDEX Name of Assignee Chemische Fabrik, vormals Weiler ter Meer See Weiler. MEL MIO? SR SRMAM LOTT L1G. 5's. occ so ee so 0,00 clan ans ov vicnsee vows Chemical Products Co. UNE ET RMD Ot) ee eerie ol cores esha lees c a,cnerecnileje elee ale cis Vege oie og EE MICRO R Ces s og Kos sacri sagevigcidesecsoeruceas vas Asasipsalhieiny & 5 OLE aS tld oct ROC CRE Toe ae ne een cea tee Sale o's) oe, 5.5 aioe vie <6 bcc seas obese eciees os Ree ROO Ee AUT UMC EC aeye ci gie's, tis; as cio 6.6 l0cs v0 o'ee's 6% vdieo sew encase SearEsbeerClal Ete S@mECMM. CO. . ccc oc seen cess ce cetncccsveeseeven Compagnie Nationale de Matieres Colorantes ............22000- Compagnie Parisienne de Coleurs d’Anilin ...........0. ee eeeee Consolidated Color & Chemical Co. ....... cc ccctcsccacscccens Consortium ftir ElekKtrochemische Industrie ..............-08. Cordes, Hermanni & Co., Ichthyol Gesellschaft .................. Granmaumigde, Societa General per la ..... ccc cece cess encnencvece Dahl & Co., Wiilfing—, Actiensgesellschaft. ........c..ceeeceees (peer, UCM SRALGS so SNE Sra Ge ee PivermxnttOlogical Research Faboratories .......ccenccecreeccscucs Deutsche Gold und Silber Scheideanstalt, vormals Roessler. See Roessler. Deutsche Luxemburgische Bergwerke. See S. Hilpert. eee iy and tT Raynolds Co. 2... ccncsetensersevaces basa ten CREE Cy em ATC CIN fsec se se cc macew s 28 eos au sais wales a es.s es MES M AV EE Sar CM eIIICAl BMC I cc dic vis sae o o0 sc 0 cleis wisn ove e's sss eeee oe LUetRvcny (Ci cgkrtesil) (GG) gk ast Sa aries trea ar ae ar aR ROTI TINE ATU COG e sere alee sigio snc siaccc sit ocisiv cesses. de teessetows Ulver nt, TRyesivece De sveeS. 5 eee Gio ae DOICEeL ona ROR MRI eee peepee oe Nemours w Co. WH. Dy ow. cee tee veces ecsvinnes Durand, Huguenin & Co., Dyeworks formerly ..............5008- PPE AIASU OR MICO CALC Olt tiie a releis. 3 oe sls 6.04 44> 400 60 6 0 0% 6 ose ws aiers oe RORECE SME Niatiitactiring CO. avis ccc tcc ese sec te ce eee nea wae ce Elberfeld Co., Farbenfabriken von, (see Bayer.) .......... aa ORR CMO Ns siege silat wes we oes ces esse sues be cow ace sienile eeceerer eee eee eee eee reese eeeeseseseeeeeoeseeneos Fabrik Chemische Praperate, von Dr. Richard Sthamer. See Sthamer. Fabric Ormnamenting & Manufacturing Co. ........-.eeeeeeeees Fabriques de Produits Chimiques de Thann u. Mulhouse. See ULER SN SRN lei iGrs ac aaie soso gics lewis kets 64s bin ere see a ae 8 8 80 Farbenfabriken, volmals Friedrich Bayer & Co. See Bayer. Farbfabrik, vormals Broénner. See Brénner. Farbenfabriken von Elberfeld Co. See Elberfeld. Farbwerk Miihlheim, vormals A. Leonhardt & Co., See Leon- hardt. UME EPCS E Witt, FIANMTON foe ee ce ee tee eset sede veces nesus NRC NM OCG) PTBNL Sac cic ewe ce reece rene ne esc arwese nes eee Bee was 20) SEE oe crc e ails ot 6) S216. oc s.01c.2 06.6 wiecieiene eo Wise 96.6 eles 6 eaislias Seem Licht & Cake Co. ... cnc cece sence cccscesesesngescevevens GesOlimne Recovery Corp, 2.2... ccc cc ccc cc ccc esccescccscces BRMROMMG WV TIATN ING occ cc ct cect cee ec eceee rs eenseteresetas Geigy, John R. Anilin Color & Extract Works ..........eeeeeees Wremeral Omemical Co. ....52.-. 00 c ecco cccces ae pub he in otiie General Motors Research Corp. ........ccceccccececerevsceece MRPUBOM gs FUUS oon ss ee cen eens ccc ees enrtocsceseneess fees Gilliard P. Monnet et Cartier, La Societe Chimiques des Usines du Rhone. See Soc. Chim. MEORERIIMTE So SPCHCEF 2. www cc ecw ce cr rem ce encsresecesennvuces Gold und Silber Scheideanstalt, vorm. Roessler, sche. See Roessler. Goodyear Tire & Rubber Co. .... cc ccc cece eee e cere e eres eeens Geeemells Chemical Co. ccc sce ccc ce cc nee teense ae sinevsseenic Griesheim-Elektron, Chemische Fabrik ..........eeeeeeeeeeeees Grunau, Landshoff & Meyer, Chemische Fabrik Aktiengesellschaff Hansmann & Co....... A RO A SF Eee oe TOE ONE on Ce NE ee ee hice ard bec ben ese co Were NOs gem ades sem sare oe PPRRPURIOM Se POWUCE CO.) occ ceed sciasc@awe ees e590 606.6 o¢ 90is0.9 6.01018 Heydem Chemical Co. .......ccccee cece see rccreseccereacs er Hilpert, S. Deutsch Luxemburgische Bergwerk und Hutten Alctiengesellschaft 22.2... 2.2 ccccccccntccesenencceeneesornces Hoehst, Meister, Lucius & Brtiming .... ee ee eee eee ee sere eeees 479 Address Delaware. Boston, Mass. Manchester, England. Clayton, England. Barmen, Germany. Arkansas. Sandusky, Ohio. New York, N. Y. Paris, France. Creil, France. Newark, N. J. Nuremberg, Germany. Hamburg, Germany. Rome, Italy. Berlin, Germany. St. Petersburg, Russia. Philadelphia, Pa. New York, N. Y. New York, N. Y. New York, N. Y. Wilmington, Del. Midland, Mich. Boston, Mass. Wilmington, Del. St. Fons, France. Rochester, N. Y. Philadelphia, Pa. New York, N. Y. New Jersey. Berlin, Germany. New York, N. Y. Thann, Germany. Basle, Switzerland. Hamburg, Germany. New York, N. Y. London, England. Wilmington, Del. Indianapolis, Ind. Basle, Switzerland. New York, N. Y. Dayton, Ohio. New York, N. Y. London, England. Akron, Ohio. Cleveland, Ohio. Frankfort, Germany. Griinau, Germany. Vienna, Austria Hungary. Feuerbach, Germany. Wilmington, Del. New York, N. Y. Bochum, Germany. Hochst, Germany. 480 DIGEST OF PATENTS Name of Assignee Eo ti mam 6@ Kaiessig 5 eis eaece. oe eevee cats Dn ee Oe ae + ete Hoffmann-La Roche Chem. Works. See La Roche ............ Holley, Alfred EK. and Owen E. Mott. See Chamce .............. Hollidgry; oh Bish Comm aie tee ns isen s cheile Wicks ister e Gist ete chee eee Holliday & Sons, Ltd. Read- See Read-Holliday. HookerElectrochemical "Cos ve s% sc ne uc cisco etenateere letersi eeneeeeete Hoops, Urs Henry W.e.ie we occa fctsis toe kee lolere occa eleva eis eerste Horowitz, Arthur ioe ec Felice 2 osticrcieie oo oelece oe ale ntaleis evereter ieee nee Huamt, Seth. cB. Get aicecic «| grit bisseieaie ori pinie sate el ete severe eee Ree ee Ichthyol Gesellschaft, Cordes, Hermanni & Co. See Cordes. Imperial Trust for the Encouragement of Scientific and Industrial eoeeveeceee RESGALGH. Vilace.sisidinyaighe.o-o t sveisie es Bivial ounces wisrersvarteelaeletebel tT Shehene ne Renee Import. & By=Products; Co. : tic cas + wets slecere tsite es sian et eaee eee Industrial Alcohol Co., U. S. See U. S. Ind. Ale. international) Coal (Products (Coss:2.5.. 6 eet ee ec eee eee PAREOE, Carl uss 55 occcécate haile ctereeier ete. oe: a oie eave tetas leetaroneve ten ue Renee KK... & -P.: Chemical | Corpic ic so vei cage nie © cesta wie) tue oes sient er a eee ae Kalles& Co., Aktiengesellsclatty ics ci. srerereusic cna lenlv eters teri etel enna Kalmus; Comstock & Wescott, Ince savas ss ca cies co eleieina seen Karerag, Patil op siiiecacis s clcteveeisis svete sities cvsie ene sue eal este) eaten a een Weller, Job) eon. co cio coo oo lece wie guest alle a) eineifele mie cle er eeetel tein aman Kellogg, Marie Loutse .cis0 ve ss eos ee © ore € shel ices aoa Kinzleberwer & oo. i. 6ag vuieie be actos bik nlele ole aleleerelaiercie eae eae KH pstein’ & Co. se. a re Se ls tenet cn eee Klimoseh,” Konrad Pdward sik, cys wesc osne aietee’e een ele nonin temas FRM OL & COs ee oe oes sevee pia tee oe terciare mice aay Rone ciel slerelee ry att ee Moppers (Co., The i. cece bic ies are hoes 8 aiecel e eete leit cae slated teres Kuchler’ & Butlin eulecs i ve cece wees eine 6+ wielacs oO alscciecs en ieee Kuttroff-Pickhardt & Co See Pickhardt. Lambert, Jr. Jean, and Chas. Rumpff (27-7... <1 -icisls olen teu Lapperr, Nathan Sos ii. oc ceo vce ts cuniy or atee cic eapeteiele Ste eee eneeeae La Roehe Chemical Works, Hoffmann- .........0..s+00+eeese> Laundry Bltre@ Cos iiss dice wicvovecnieicis a siu s heatiele etait ae eee Leeds: Manufacturing: Cos sins cc s/c alee )e lets nities aiatoys, comeleiettieaeteteieeninee Leipziger Anilin Fabrik. See Beyer & Kegel. Lembaceh, Adolf, Ulrich Schlicher and C. F. Wolff ............ Leonhardt & Co., Farbwerke Miihlheim, vormals .............. Levinstein. Co. [td., ‘The? oo. case cteistete 6's. la's)s nels aie ele cee LiZhtloots Job Pe. eee ce eiacsvaleuvle sue 4 arp) eos aren Shean ealng tote ne ae een en LAM y 8 Cor esate ee on ere erst care sine ete: bias bana oan oe ke List, Adolph? oy i Pele cies oes arenes tlale sll sis are ae sacle ene Onis ace ee Lonza,) ‘Blektrizitatswerk, , 2)... 5.0/0 stso'e 1 as elie slalots se ivi corona: saslene amen Macdonald, David Baird © isis vis alevs crs iole copele tise ere eerie Macdonald, Luachlan: Wa. ... v.05 vc ola cielo e oieronsleletn ele rele tetenaerntte nae McKee; Ralph od ieee wie 5 case eie eles te loo deeerta otis cette eee tetera ie eee eee Martinon, Barthelemy. ii) s sis 6 «0 415 Sleie a eles e oll e tials ete tsiereiy ten eanme Mather,’ Carl Noviuics. cre nua-stetictene marae oe tar eteheuetpstetetoaoteestene is oleaetese estes Matheson & Co., William Jo. o's. io. 6 iean 0 ote wis eb ele Saree Meister, Lucius and Brtining. See Hochst. Mlerelks: Fi 251 ooo sae w 6 econ gia ie vlere Sie eho elie! lets] elie rateuarss aus i teas ame Merrimac ‘Chemical (Cosi o0 succes wicca tiers) ie) olecele aie) oaleie sip icnet eee Merz, Kaard so. a as oes kG) iow coh ws Sree aie iene ete te ere Metalite Con Pardes Giee ee be Coie era ane ie che teeter ste eee Metz, Herman) As oiciic cic ie es tee eine o gin ee releieiti lene east ain anemone een Mitsui Mining (Cos (...\si ais os oo oenie pis se a a hiv nisl ate wade ee sive ee Monnet et Cie, Societe P. See Soeiete Chimique ............. Monsanto’ Chemical Works) 5. 7. 05 sienere wie pisiteveis e eiste eerie Morris, Edward (S.0 2h osc encase cle sce baw eee ete eee ene Mounsey, William. Edward 0.4.05... ss .cate ce eee eee Miuhlheim, vorm. A. Leonhardt & Co., Farbewerk See Leonhardt. Miiller-Jacobs, Catharina, & August Loos ............2.e0ee00- Mitlier-Pack, J J. vdkcs'ce va cseisns woh s biplalere ss otela Serenent a eres naene National Anilin & Chemical Co., Ine... oe ee oe eee tenet Oehler, Ke Fe. coed wile «cts Crete sete grace tele oe th ele ttetere he eete eee ana Parke, Davis & Co. (...66%8 cabs eckaivee oven ee eee een Parsisse, Societe Chimique de lg Grande ..........ccececccececs Pereira; Hansii sos nieces si ose h ow levee rotten luse leone lets tehette ele: tenetete nent etme ennms Address New York, N. Y. Oldbury, England. Huddersfield, England. Buffalo, N. Y. Jersey City, N. J. Berlin, Germany. New York, N. Y. Westminster, England. Trenton, N. J. Richmond, Va. Dusseldorf, Germany. New York, N. Y. Biebrich, Germany. Boston, Mass. Szolnok, Aus. Hung. New York, N. Y. New York, N. Y. Prague, Czecho-Slovakia. East Orange, N. J. Vienna, Austria Hungary. Ludwigshafen, Germany. Pittsburgh, Pa. Crefeld, Germany. New York, N. Y. Chicago, III. New York, N. Y. Illinois. Brooklyn, N. Y. Wiesbaden, Germany. Mihlheim, Germany. Manchester, England. London, England. Indianapolis, Ind. Leipsic, Germany. Gampel, Switzerland. Leicester, England. Isle of Skye, Scotland. Ridgefield Park, N. J. Lyons, France. Grand Rapids, Mich. Brooklyn, N. Y. Darmstadt, Germany. North Woburn, Mass. Frankfort, Germany. Amesbury, Mass. Brooklyn, N. Y. Tokyo, Japan. St. Fons, France. St. Louis, Missouri. Philadelphia, Pa Liverpool, England. New York, N. Y. Burnley, England. New York, N. Y. Offenbach, Germany. Detroit, Mich. Paris, France. Vienna, Austria. aes Sela NL are Se? ina ke a ate ae : » 4 dite te ae ASSIGNEE INDEX 481 Name of Assignee Pe WOAESCAIDS. (ie (Olas, NICE 1 ans (an EMER TE MOCO IS TRIRICEE ON coe pas eee ew swe nev reed nr aaeenennne BasmeeEEMED s OPRIS EE MON CTHIGAIY COP co ics co scsicc cs rissaiserceeconsseseess ROM LICE PE TATICOIS | 62. oe cc cece cece ese rcsccesrenesecees Posselt, Ernest, and Rudolf Peters. See Posselt & Co. Posselt & Co., E. Ponltene Freres, Les Establissements ............ ccc cceescccees SALE TV SMV CTO eels cis oleieke ccs oor. oe. sis eels Sind eldiwiele sade aaleiee Rasechig, Frederick Sac Ro! Goh i a ee rr RMP RTOS ORCL WE SONS LGW, cats sip cicieleig sles i cies sea sigeseieesse ee ipemmnanoel Chemical Products Co. wis eeccsccciwaicsccccccaivins Reilly, Peter C. meemewesekts Poward Sabine (Trustee) 2.2.00. .ccccccesccsccvcece Rheinau, Actien-Gesellschaft fur Chemische Industrie. .......... NEES RUMP GPIPSY iviaviris sa as cles ecco nen sinccsce re nnds res sencews PMRRSEAMEVENMRGE CECH CO Gee ian csc ce Sas gos 81es 6 2.0 ace nie wars eles ewes Rockefeller Institute for Medical Research ............eeeeee- eee RESTREAME ABT CRE Rr ree ccle os ois yokes weci elie ae gasegeta@ee sae Roessler & Hasslacher Chem. Co. ............0ccccccccccerces Roessler, vorm. Deutsche Gold und Silber Scheideanstalt ....... Doo leis (CSV ah 22 4 5 Di Gry Sy ieee Oe Ore RcnC enn ReneS ne Ir RnR ROR ac rae ar ec Rotman, D. R. RCN eM ATO Oceans = 6% ale $16.6 winis) cle 0s sieig bo ee we edie oweieee Rutgers Werke-Actiengesellschaft .........cceecceeeeeescrcoens St. Denis Societe Anonyme des Matieres Colorantes et Produits MRA Say ale see cach hrc c cee censseyeece nes deervcees Sanderson, R. E. B. Sandoz, Chemische Fabrik vormals ........-0ceeeeeere rene eeees ERE PC ee cess ca es ese secre see cce scot se tne serene Scheideanstalt, vorm. Roessler, Deutsche Gold und Silber. See Roessler. Schering, E., Chemische Fabrik auf Actien, vormals. See Chem. Fab. Meee EN TERTER@ DoT COU ae ccc ccs cc ete pws we cence ne cneeeesesennsne GSehloepfer, Wenner & Co. ......sceceewr creer eres ere sector eaes Schoelikopf, Jr. Jacob F., and C. P. Hugo. See National Schoellkopf, Hartford & Hanna Co. See National. Schoellkopf, Anilin & Chemical Co See National. Schweitzer, Hugo, and E. N. Dickerson .......-.e+ eee eeeeeee Schweiz Serum-und-Impfinstitut. Seottish Dyes, Ltd. .........-. ccc creer cccrcccscccccecesesees Selden Company, The ........cccceececcerece rece cecessereeeces BIPIRI@TOSOLWIY COl es cc ccc ccc ect ewe ses es seers nresasenss Shawinigan Laboratories, Ltd. ...... cece cece cere e crew erence Slater, John W. and Howard Richmond ........-+eeeeeeeeerees Societe Anglo Franeaise des Parfums Perfectionnes .......... Societe Anonyme des Matieres Colorantes et Produits Chimiques de St. Denis. See St. Denis. it Societe Chimique des Usines Du Rhone, La- (Gilliard P. Monnet REE Eee etelale 470) 4) 6) 670 Ke) we8 8b Se OKOs S186 ©1686 6 ee) e100) 8) 0:19 B81 Be eee se eo eee eee eee se eee eres reese essere eee ee ee eeeees eoceoeer roe er eee eee eee eee eee essere seeeeeseseeonseos eee ewe eee eee see eee woe eee eee ereseseese ere ee sere eeese eee ece oe ese ee ee eee ee ees eee eee ese eee esses esesre eee eoebe eres oeee sees nvvovreeeeereneeaeereeseeeren oeoeeererese eee eere ere eee eer eee ee Peritetree late. aisle 64 i ie ee rrcke hce ee aio yoke ip eseiene) ae: 6, 9, sc'eleoue Societe Anonyme VAirliquide .......... cece cere ee eee ee eees Societe Generale per la Cianamide. See Cyanamide. Society of Chemical Industry, The, See Basle. Societe Chimique de La Grande Parsisse See Parsisse. South Metropolitan GAS Co. 2... cece cece cee treet eee eee eeeneee Squibb & Sons, E. R StaMGArd Oil Co. 6... ccc cece cas ce cc crressrrcctansersseruerses Stearns & Co., Frederick ....... cece e reece cree ce eet ereecseces Stewart, Isabella Jessie Sthamer, Fabrik Chemische Praparate, von Dr. Richard,......-.-. Btolces, John Stogdell ..... 22.22. cece rece ese resets ecsecenrces Sunbeam Chemical Co. .....ceceecccccerserscrecrersesreceees Synthetic Hydrocarbon Co. 2... cece reece cece reer ere ecceeeees Synthetic Patents Co., Inc. 2.0... eee e eee eee eee e ence eee eeecees Tainan Seito Kabushiki Kaisha ...........-.- ste e nec ceeceenes Thann & Mulhouse. Fabriques de Produits Chimiques .......- Twitehell Process Co. ....ccc cece cee c cere eee eeeeceeseererere Union Carbide Co. ..........+-5- Tee ne aaay teem Tien aa els: stahesetsueemone ke U. S. Gow’t. (United States Government) ....-..eeeeeeeeeeres U. S. Industrial Ale@ohol Co. .... cece ee eee eee eee eee eeeenes ERGERLE Shs elieim © el S48 8) .e:.6 61818 8. 0a 52) SFO SSSle ONO S RNAs Ry Ree Sip (6 ToL adel ee eee 6) Sh: PST CBS, WSR AO Re OO) Oe eS Bh Ie Address Basle, Switzerland. New York, N. A Point Loma, California. Paris, France. Bradford, England. Paris, France. Hamburg, Germany. Ludwigshafen, Germany. New York, N. Y. Tumbridge, England. Chicago, IIl Indianapelis, Ind. News .York, | N. 0 Ys Mannheim, Germany. Charleston, West Va. New York, N. Y. New York, N. Y. Darmstadt, Germany. New York, N. Y. Frankfort, Germany. Hochst, Germany. New. York, N. Y New Jersey. Berlin, Germany. Paris, France. New York, N. Y. Basle, Switzerland. Alton, Ill. Leipzig, Germany. Fratte di Salerno, Italy. News Work, (Nea Ys Berne, Switzerland. Carlisle, England. Pittsburgh, Pa. Syracuse, N. Y. Montreal, Canada. Providence, R. I. Courbevoie, France. Lyons, France. Paris, France. Paris, France. London, England. New York, N. Y. Indiana. Detroit, Mich. Victoria, Australia. Hamburg, Germany. Philadelphia, Pa. Chicago, Ill. Pittsburgh, Pa. New) York, (Nveys« Tokyo, Japan. Thann, Germany. Cincinnati, Ohio. New York, N. Y. Washington, D. C. Baltimore, Md. 482 DIGEST OF PATENTS Name of Assignee von Heyden, Actiensgesellschaft Chemische Fabrik (von Heyden Nacthfolgers ® Dri, TH) a sisniie care oie faletaie paeate ante siela aielatn sun taco eee Wedekind sR S&S Gorrie e 8 cas Siac tebistele sy che boas, thanets ay deep enataente Weiler -ter-Meer. Chimesche Fabriken vormals ................ Westfalischanhaltische Sprengstoff-Aktiengesellschaft. ......... W. Va. Pulp (West Virginia Pulp & Paper Co.) ........000200- Williamsburg Chemical, Co., Une. ecco oe bisminie ne 6 sense sage (Wise, Morris, and, Louis Stettawer 2. cdisis «pe wine suaeiens nl enednsee teers IW eel fi mess} oan ASS hays ele dew clase sen wins we Wise eats ota) eleloieie la euenetche rene tas Rees Wilfing, Dahl & Co., Actiengesellschaft. See Dahl. MOUM yt CO, a eake ea eran ere ie iets tere Savevstaepapetetevote ce shetrid eaters Zimmer, Georg) Carle cick son ole sbeleelacers oleieres ine: sree seltteis teas Rees Zimmermann & Co., Chemische Fabrik, A. G. Brugg, vormals, Dr. See Brugge. Zimmermann, Emil and Chas. Rumpff ............. cece ewes Address Dresden, Germany. Uerdingen, Germany. Uerdingen, Germany. Berlin, Germany. New York, N. Y. Brooklyn, N. Y. New York, N. Y. Berlin, Germany. Hanover, Pa. Mannheim, Germany. New York, N. Y. ar oe COLOR INDEX. Patent numbers are here arranged by color on fiber, by method of application, and numerically by chemical groups. The method of application of each color is shown in bold-faced type, and the chemical groups are indicated by means of eo roman numerals. BLACK Acid 843,077 749,913 Basic 525,245 790,363 Ws 843,137 753,057 Mordant 525,626 790,364 VI. 843,149 754,264 530,532 797,441 354,746 843,756 750,571 V. 536,878 803,592 396,293 454,045 843,808 787,824 536,879 807,422 412,440 456,627 844,814 790,079 536,626 555,359 823,793 425,885 456,897 863,290 806,053 556,298 835,539 438,438 476,336 874,967 VE. 556,439 839,489 440,639 515,339 887,348 1,032,433 557439 843,137 449,629 543,747 899,171 536,626 578,580 843,149 ALE 546,068 906,421 Developed 582,958 844,814 462,415 546,069 912,356 VI. 582,959 863 290 466,202 557.440 921,239 II. 583,439 887,348 ieee 562,200 Re. 13,122 458,283 583,634 nas or tage 583,439 932,812 476,336 38,589 586,865 12,356 482,106 593,790 932,813 502,368 Re. 4,746 588,181 es So ees 602,856 935,031 546,070 Re. 4,747 588,182 eeaee ery 603,093 944,328 557,440 79,942 588,203 S703 $136 606,438 945,780 562,200 Re. 3,103 601,033 oe 045 ne 9 611,112 950,405 628,721 96,242 602,856 9 9,450 498,772 613,638 958,830 631,089 106,616 602,857 1,000,600 49 773 613,639 958,912 640,010 111,654 603,008 1,014,039 501,11 618,963 982,952 644,234 127,103 603,093 1,014,633 501,500 624,256 982,953 654,065 138,155 608,999 1,042,356 502,912 627,783 989,000 655,529 193,158 613,641 1,056,493 511,688 628,025 989,001 740,767 213,907 613,642 1,078,925 512,167 634,009 1,014,039 > 740,768 248,934 620,574 1,078,926 515,339 639,041 1,078,925 749,195 283,220 624,256 1,092,842 516,604 644,240 1,128,813 792,032 287,112 625,198 1,101,739 524,665 644,334 1,128,814 792,033 331,777 627,783 1,122,564 525,245 646,711 1,159,375 797,441 343,793 629,748 1,128,813 525,626 654,065 1,199,233 835,539 355,934 632,503 1,159,375 526,763 654,167 1,213,075 839,489 387,094 634,824 1,199,233 533,463 654,168 1,235,253 841,371 390,842 644,233 1,206,232 533,508 655,529 1,323,285 843,077 391,315 644,235 1,209,154 536,431 664,955 1,325,841 843,149 409,819 644,236 1,213,075 536,532 667,935 1,375,701 843,756 409,820 644,237 1,215,359 536,878 677,231 1,408,296 863,290 409,821 644,238 1,241,153 536,879 680,283 887,348 409,822 644,239 1,323,285 $41,750 688,647 XV. 924,231 409,823 644,230 1,328,841 542,073 716,242 933,841 452,324 664,955 1,363,886 $43,212 716,289 594,106 933,842 491,673 665,696 1,365,040 543,748 722,715 609,327 935,031 491,951 676,494 Payee 556,164 722,716 646,795 958,774 491,961 677,231 are yet 556,208 25,848 749,913 958,912 499,410 680,283 pees a pe 1,375,701 5572435 726,695 756,571 999,558 499,088 683,120 1.473.488 E4437 727,963 953,008 1,014,039 £29,499 692,675 Dies G8: 537,430 727,964 1,078,925 £39,550 692,676 ae a 560,448 727,965 XVIII. 1,233,433 §42,04€ 693,670 XIV Are 727,966 1,325,841 592,022 716,242 . meee 727,967 980,251 1,375,701 Re. 11,647 722,715 ees 728,021 999,028 1,408,296 787,221 722,716 455,952 oe 729,601 959,516 725,348 ne ene 737,967 Acid XV. 963,056 726,695 XV. aie 741,936 Mordant 1,105,554 727,962 $7095 Ss 765,581 661,438 1,144,181 727,963 639,806 57855 778,476 III. 1,144,325 727,964 675,585 ee 790,363 XVIII. 727,965 a eed 792,032 368,054 Il. 727,966 XVIII. et a8 792,034 . 450,037 999,028 727,967 Ate 7975441 452,210 646,795 729,001 980,251 soe tas 797,731 599,425 Basic 737,967 - sean 797,732 619,114 VI. 741,936 Direct apnas 803,592 623,638 VI. 759,613 200) : 823,793 631,613 473,928 765,581 Ill 591,61 835,539 631,614 1,028,140 493,564 770,177 . 594,996 839,489 646,795 1,029,639 501,160 778,476 595,021 841,371 653,492 1,032,433 501,500 778,610 653,492 599,532 484 DIGEST OF PATENTS BLACK—(Continued ) 601,033 683,120 1,092,842 102,270 Re. 11,659 646,873 764,734 602,856 688,478 1,099,676 1,079,568 532,484 647,493 901,970 602,857 692,675 1,101,739 1,261,858 532,503 647,846 904,224 603,008 692,676 1,209,154 1,464,079 545,337 648,597 909,155 605,103 693,670 1,215,359 546,576 648,753 927,868 608,999 717,550 1,235,253 VII. 560,334 648,754 935,009 613,641 748,076 1,241,153 594,105 648,755 961,387 613,642 759,613 1,363,886 872,086 594,106 649,218 961,388 613,645 770,177 1,365,040 881,157 594,107 650,293 1,026,881 615,47 778,610 1,371,979 941,152 596,559 650,326 1,099,039 618,963 807,422 1,3725439 947,030 597,983 650,327 1,105,515 61y,194 832,393 1,378,388 985,767 601,363 651,077 1,151,628 619,503 585,444 1,415,704 985,768 601,365 651,122 1,187,614 620,574 859,930 XIV 985,769 608,355 653,277 1,261,394 629,748 950,404 : 985,770 609,327 653,278 1,265,837 634,009 963,739 455,052 1,001,457 610,541 655,659 1,274,351 634,824 969,450 { 1,005,140 618,152 661,438 1,279,307 hoe 982,952 XV. 1,005,141 Sepp 665,547 1,316,742 39,041 987,417 1,144,577 26,897 644,233 999,558 546,576 1,157,485 628,607 aap ee! Stole 629,221 71,90 644,235 999,713 9» 1,243,170 628,608 peer 644,237 1,000,606 639,806 1,466,687 628,609 ie Lakes 644,238 1,014,633 647,846 629,221 ay 2 644,239 1,014,982 647,847 XV. 635,168 San 644,291 648,753 : 692,174 VI. 644, 9 1,014,983 Baers ; 635,169 695,835 eee es 1,014,984 667,689 ae 636,066 698,220 ioe 1,028,140 : 639,806 701,051 953,008 665,696 1,028,306 aati Sulfide Vat 641,587 702,369 671,543 1,029,639 641,588 706,969 XV. 673,079 1,056,493 Lid, mV. 641,589 711,038 676,494 1,067,881 644,059 740,465 679,221 1,078,926 975,863 523,138 645,738 764,733 1,206,232 BLUE I Acid Til. 5955349 5955350 605,508 605,921 617,981 623,219 623,220 632,621 648,271 648,332 654,294 656,668 656,669 656,670 656,730 658,513 658,514 666,594 666,702 668,445 669,894 673,691 675,572 675,574 675,575 682,523 687,658 688,645 692,762 704,798 7075373 707,374 71 1,31 16) 713,432 715,062 727,389 729,073 734,866 738,614 738,375 754,768 764,837 779,825 831,002 844,835 958,850 1,045,805 1,078,505 TIT, 510 1,207,981 1,280,648 V. 451,502 524,677 602,544 603,013 606,295 609,352 673,640 872,815 940,354 1,015,354 VI. 345,901 3575274 454,645 456,807 502,369 521,985 521,986 524,009 524,677 531,977 534,809 539,699 546,068 5573438 563,383 563,384 567,615 611,664 633,639 634,009 652,456 654,064 677,227 677,228 677,229 677,230 700,565 703,105 710,059 718,181 722,860 727,962 727,964 727,966 727,967 739,118 741,552 754,315 759,284 7973441 797,461 798,808 805,918 806,415 826,279 826,280 826,281 826,282 827,468 841,371 843,077 843,137 843,149 843,808 844,814 846,511 865,252 877,643 879,053 891,931 921,105 921,105 Xe. 13,121 032,812 932,813 958,830 1,014,039 1,023,199 1,024,308 1,028,006 1,052,262 1,128,813 1,128,814 1,188,421 1,216,760 I,235,253 1,316,781 1,323,285 1,325,841 1,375,701 1,402,350 1,429,781 VII. 524,256 540,564 620,442 621,652 622,139 677,239 677,240 XI. 348,816 444,538 451,502 531,148 534,809 547,173 585,934 643,338 XV. 594,106 609,327 953,008 XVI. 434,493 607,408 XVIII. 297,416 331,964 331,965 333,861 412,615 422,018 437,989 463,898 472,091 490,408 506,918 519,971 538,215 547,173 564,801 567,567 580,186 580,187 580,188 583,267 603,016 . 605,119 621,393 647,260 647,834 658,504 668,580 673,632 676,555 680,732 688,066 709,160 727,964 835,682 877,052 887,620 891,888 891,889 976,417 978,801 9955494 998,139 1,026,089 1,042,498 1,052,262 1,065,405 Re. 13,969 1,277,238 1,237,192 1,387,596 1,478,039 XIX. 413,049 551,885 1,054,247 Acid Mordant iit, 258,530 399,480 399,481 399,482 401,633 401,635 446,892 476,418 476,419 476,420 496,139 502,603 502,765 503,295 a 506,265 519,229 527,457 569,418 569,419 595,349 5951350 605,568 605,921 617,686 617,981 619,115 623,219 623,220 627,896 631,613 631,614 632,621 633,950 648,271 648,331 648,332 653,492 654,294 654,505 654,506 656,668 656,669 656,670 656,730 666,594 666,702 668,445 673,691 675,572 675,574 675,575 707,373 707,374 729,073 734,866 738,614 748,375 753,057 754,264 754,768 779,825 868,399 1,090,123 V. 536,626 VI. 420,372 420,374 447,302 502,369 654,064 683,119 684,065 718,028 749,195 797,441 805,918 806,415 826,279 826,280 826,281 826,282 827,468 841,371 843,077 843,137 843,149 846,511 865,252 999,558 1,014,039 1,025,267 1,114,771 1,221,849 1,233,433 1,234,094 1,237,192 1,237,193 1,259,499 1,203,231 1,292,385 1,316,781 1,323,285 1,325,841 1,375,701 1,408,297 1,419,501 1,426,189 1,426,190 1,431,655 1,437,758 VIII. 617,628 XI. 252,274 253,443 253,444 253.445 255,350 364,320 366,356 366,357 420,164 440,536 444,532 497,114 518,458 524,235 531,148 534,809 547,173 585,934 613,578 616,622 638,576 643,338 662,224 707,832 707,833 807,181 842,303 844,156 893,855 895,635 898,039 898,098 898,842 902,154 936,247 955,040 961,362 992,613 1,000,899 1,028,045 1,199,458 1,227,407 1,268,455 1,299,070 COLOR INDEX BLUE—(Continued ) XV. Basic VI. Mordant 657,768 447,302 657,769 V. 501,500 525,492 XVI. 352,361 536,532 392,723 556,298 323,514 458,281 558,344 332,514 491,378 558,438 469,329 511,653 569,392 524,322 536,626 578,432 520333 617,703 578,580 536,163 566,162 539,738 VI. 588,203 560,795 601,033 606,212 524,251 oo 524,252 602,85 XVIII. 524,253 611,597 524,254 613,641 331,964 613,642 333,861 Da, 614,391 478,005 629,748 484,697 254,064 644,233 538,215 254,065 644,238 377,052 255,349 pbs 877,053 369,764 676,495 877,054 404,309 677,227 976,417 413,562 677,228 998,139 431,541 677,229 1,004,610 442,680 677,230 1,042,498 494,838 692,675 1,044,836 400,243 710,059 1,065,405 1,188,259 718,028 Re. 13,069 eee T2375. 727,904 37> 93 XVI. 727,966 27,96 XIX | sogirgs | 7270902 1,88 eaeneT 797441 Pik 380 270,311 806,415 2194;3 362,502 ee Basic 366,639 843,137 366,640 g 43,149 V. gues 844,814 905! 393,300 oh ae one 456,201 2 1,378 879,053 ee XVIII. 888,030 578,003 916,323 613,920 263,420 920,151 726,667 207,413 969,450 900,302 207,414 999,797 207,416 1,000,269 VI. 308,748 1,010,433 471,638 1,014,039 476,413 1,014,633 613,920 496,435 1,020,670 649,727 517,473 1,023,199 649,728 525,627 1,024,081 1,032,433 CAESS TO 1,028,006 1,416,621 661.800 1,032,412 664,450 1,034,898 Kit: 816,457 1,038,209 1,004,609 Meee 263,341 1,149,575 1,042,35 1,470,555 bear I,07 92 ebets ra 6. 07043 1,057,430 43,066 1,054,247 1,088,735 248,153 1,090,379 263,420 Developed 1,099,108 207,414 688,067 G 1,113,468 1,232,550 392,723 1,125,050 1,470,555 673,640 1,128,813 1,150,675 1,160,406 9,344 1,180,985 1,183,378 1,188,545 1,215,359 1,237,192 1,316,781 1,319,852 1,323,285 1,325,841 1,365,040 1,371,979 1,375,701 1,378,388 1,416,621 1,422,866 VIII. 261,518 4 5 255,349 XV. 625,717 649,218 675,585 678,884. 688,999 XVIII. 877,052 877,053 877,054 887,620 976,417 978,801 995,494 1,026,089 1,237,192 Direct Til. 627,896 648,331 653,492 675,574 675,575 734,866 VI. 3573273 357,274 360,792 366,078 380,067 388,185 396,293 415,258 417,204 417,295 417,296 421,640 423,550 423,970 432,989 440,953 442,369 485 454,645 462,824 464,135 467,162 476,337 476,371 482,106 483,368 493,563 496,392 498,303 498,404 498,405 408,759 498,873 498,874 499,198 499,216 501,118 501,500 506,284 509,929 511,532 511,688 512,493 516,757 516,760 521,095 521,985 521,986 524,069 524,070 524,220 525,492 532,125 533,508 534,573 536,532 536,880 539,699 544,699 544,700 556,298 5575435 5571436 5573438 558,344 558,438 558,613 560,796 563,384 563,385 563,386 578,432 578,580 5795773 583,635 584,981 588,182 588,203 591,616 601,033 601,859 602,855 602,856 606,181 606,264 606,436 611,597 613,640 613,641 613,642 613,646 614,391 620,368 620,369 620,574 = DIGEST OF PATENTS 629,748 1,188 ; eocens 820,379 619,88 634,000 | 1,210,751 837,775 eipane eee 146 Gi687 893,499 yee 1,215,359 844,914 620,562 Pants 1,473,887 919,572 644,238 pga a Mlb er hier 620,563 pe: VIII. 931,598 648,623 | 1,268,031 sepa bg 894,579 956,348 652,456 estas Sol cos peers? 899 863 263,341 ere 656,6 Nae at , 43,502 ; 966,092 ae acne Beenie? 644,326 Sogee4 | guttide Vat | Ponscre 658,897 waa. , 40,841 f 1,083,110 ceaaee kre oats 948,204 647,279 sd ate xy 1,083,489 1,365,040 970,378 6 915,338 670,398 I 2 47,281 6 I,105,515 676,405 pila 985,352 651,453 910,030 523,138 1,128,371 682,510 1,378,388 992,567 657,539 916,031 Re. 11,659 1,175,230 ae 1,422,866 993,735 661,871 918,920 560,334 1,247,475 700,565 VIII. 993,736 662,073 920,156 594,106 1,265,836 709,186 994,756 662,703 937,040 601,364 1,302,671 724,893 261,518 998,156 662,754 937,041 609,327 1,329,898 728,477 XI 998,772 662,755 9375194 611,611 1,449,681 759,613 ; ant lee 669,794 943,560 614,538 1,465,853 792,600 254,064 1,008,906 675,217 943,561 620,428 1,471,854 860,220 255,350 1,008,908 677,239 948,241 629,221 L 860,221 413,562 1,014,204 680,395 955,410 632,170 akes 877,643 440,536 1,022,781 690,332 955,699 642,256 Tit. 877,644 1,032,216 697,545 957,683 649,218 888,036 XV. 1,038,589 704,804 958,464 657,768 1,090,123 °897,529 626.2 1,047,812 706,921 958,465 657,769 Vv 898,217 ae 1,052,507 712,190 959,617 660,770 : Teer oe : 1,052,520 712,793 960,671 665,726 378.003 920,151 59 1,063,000 713,437 961,396 667,486 617,70 031,423 XVI. 1,076,329 714,000 961,397 673,388 97 03 931,424 aPaO7 BE 714,042 961,398 675,585 VI. 933,446 #46,327 Brs07:982 715,074 961,399 678,084 033,447 XVIII 1,317,160 726,688 063,377 679,199 1,157,525 Seasaue 1,329,435 727,270 980,140 Re tems VIII 933,562 32,065 dices by 729,217 984,442 693,632 Ce 950,404 252,203 1,452,774 Reape 998,596 ee 261,518 969,450 327; 31,385 2 : 999,558 471,638 ns 737,836 909:439 695,534 as 999,797 688,967 233,458 746,965 1,005,481 aes 1,031,823 Leggs XIX 233,459 Nes 1,012,363 709,151 XI > ’ ri ’ . pouess : ahabe 7611440 mph 710,766 1,020,670 é 37698 240, 765,996 anes 723,154 420,164 I 020,756 17,628 ayo 768 455 1,025,174 727,387 616,622 1,024,081 Reducin 2 a 772,775 apaeth. 728,623 er 1,024,308 Vat auoteas 776,884 ae 732,090 898.098 1,032,412 III 250,036 778,725 me Sryek oe 1,032,433 : 251,499 778,752 1,042,679 haps 1362 1,034,898 682,523 251,500 2995077 1,043,468 ern XV. 1,038,209 692,762 251,501 807,782 Seta 742,189 1,038,210 724,78 251,071 812,598 f pape te 747,643 772,931 1,078,926 legis 257,812 823,204 eee 750,113 953,008 1,079 415 ye 9 257,81 836,309 1,057; 87 7555428 1,082,923 beget: Peas: 839,099 mite 7631193 XVI. j ‘ Ofns 763,320 vanes | Hits | Bred | gua | reume | geezse liao 1,088,735 Vacivae 259,261 850,444 Adaya Sd 7751570 pi 1,090,379 787,859 259,629 856,687 1,133,031 776,264 9097 1,101 262 856,776 1,144,577 777323 XVIII. ’ 9739 798,104 1695 977 1,175,63 8 8 1,125,050 801,418 276,888 860,900 peer. 779,47° »41 868 1,188,543 790,167 661,800 1,150,675 809,892 276,889 : 9755 1,211,413 802,040 1,232,551 Le eae 809,893 ad ar ge Re Tuas 818,980 1,383,710 1,169,344 809,894 ei gat he o 1,247,927 820,501 1,478,039 1,180,935 Sir 105 1,158 1,293,680 : 471 618,096 88 821,378 ’ 1,442,743 864,644 1,054,247 ane COLOR INDEX 487 BROWN Acid 1X: Basic geasee 535,036 Reeecoy 658,055 f 957,999 543,539 658,286 “a res. ies ge 558,612 III. 660,058 656,981 XII, 341,091 993,020 558,614 660,067 656,463 3 462.At4 997,061 563,386 186,032 660,097 707,374 OFS 879,424 1,009,952 567,413 791,869 661,907 1,196,422 XVHI Bae ato) | ot aets 588,180 874,743 665,547 Toyvao4e (| ose! eioes o7 490 674,137 VI. 980,251 1,021,364 588,182 893,412 681,689 Boe x6 Basic 1,021,365 588,183 909,800 687,072 210,233 “ner eicen Sper seh 403 915,385 687,581 257,242 1,021,365 I 1,025,983 602,858 922,282 688,885 257,243 | 1,021,366 1,025,984 603,009 925,917 690,271 260,242 1,023,977 1,455,486 gated yt ied OO 35290 9295443 712,176 261,175 1,052,135 603,648 935,827 714,542 261,766 Acid VI. 1,052,262 608,024 935,878 718,342 261,767 Mordant 1,052,647 611,111 938,565 723,448 262,620 221,114 1,056,080 613,643 938,566 746,926 269,359 III. 515,100 1,078,503 613,644 943,717 801,598 332,820 602,639 1,082,581 622,961 957,040 866,939 380,928 188,061 ee 1,092,842 644,462 957,041 886,532 384,316 443,402 1,123,263 647,237 957,042 889,936 454,645 452,210 420,311 1,126,466 665,696 957,125 895,637 456,627 511,901 XI 1,173,077 683,190 958,325 897,873 456,807 643,451 . 1,183,378 693,670 970,278 909,151 602,858 653,492 - 548,344 1,185,413 718,032 971,225 909,152 603,648 656,081 2 OE Diede hart 77e 1819 Bae 0a 909,153 610,349 656,463 985,424 Neha PHz65 06 9931992 909,154 624,256 686,356 ; 1,327,688 903,284 999,680 909,155 628,814 707,374 XVIII. 1,338,506 946,050 999,798 909,156 647,236 793,558 1,365,706 946,051 1,009,981 900,277 655,529 868,399 1,023,977 1,382,196 946,052 1,018,433 915.385 658,506 1,090,123 Diteleed 1,405,087 O7T,111 1,028,637 934,302 658,507 1,196,422 evelope 1,411,245 971,112 1,034,895 034,303 671,902 II. 1,419,500 978,580 1,044,933 960,652 671,903 2 XIV 982,250 1,047,813 961,387 671,904 298,998 ALY. 982,952 1,050,829 961,388 672,714 424,019 739,071 455,952 oeenee ti? 73553 996,485 679,053 431,297 ; ; O97;001 1,090,636 999,045 680,283 452,197 VI. XV. 999,713 1,095,780 1,061,714 688,647 509,623 1,009,952 1,120,475 1,081,601 716,289 548,416 515,381 561,276 1,019,321 1,162,496 1,081,602 719,048 584,460 588,181 900,152 1,023,120 1,209,212 1,096,715 754,856 602,641 588,182 909,153 1,024,308 1,216,921 1,098,259 767,069 602,858 588,203 1,025,983 1,261,858 1,098,260 790,363 655,529 602,858 XVIII. 1,025,984 1,266,896 1,099,039 823,793 657,064 603,009 1,045,196 VII 1,102,171 879,053 657,065 603,090 980,251 1,052,135 : 1,112,445 879,552 718,028 603,648 1,021,304 1,052,647 872,085 1,126,630 902,186 7371445 608,024 | 1,021,365 oe ah 888,852 1,128,368 906,421 807,289 610,349 1,021,366 1,074,046 940,586 1,132,922 053,033 870,552 624,256 1,023,977 1,078,503 943,078 1,165,531 953,034 936,321 628,814 Direct 1,082,581 968,697 1,187,614 953,035 981,276 632,503 1,087,428 1,243,170 1,199,697 964,919 987,362 647,236 III. 1,092,842 1,266,092 1,244,795 980,251 1,077,492 658,506 1,099,676 1,434,983 1,244,796 6,466 3 982,952 1,210,808 658,507 653,492 Ae rs 1,444,277 1,251,368 987,999 1,216,812 665,696 Tol TOOT 7 1,461,435 1,251,369 989,001 1,216,813 671,902 VI. 1,183,378 1,268,803 paate0 1,221,849 eats oye pire XV. 1,308,552 995,1 I I,2 71,904 2 ’ o I Io I 1,021,364 peed 672,714 221,116 1,282,355 561,276 Cee 1,021,365 1,235,253 680,283 221,119 1,283,296 Sulfide 1,318,022 1,024,308 1,264,604 688,647 302,170 1,310,532 Vat 1,327,862 1,027,132 1,281,243 693,670 365,409 1,327,688 1,358,490 1,043,873 1,283,296 718,028 380,493 1,292,385 XV. 1,405,446 1,052,262 1,292,385 718,032 384,315 1,365,706 ae 1,452,805 1,076,321 1,338,500 754,856 384,316 501,27 1,077,492 1,382,196 767,069 384,342 IX. 561,277 Lakes 1,106,781 1,408,363 778,610 399,581 eager III 1,199,234 1,411,245 790,363 430,534 599,559 : 1,199,890 823,793 440,288 1,412,707 603,755 1,090,123 1,210,808 $0 879,053 454,645 606,193 1,216,760 870,552 465,116 XIV. 608,355 VI. 1,216,812 413,724 906,421 491,422 611,610 82.8 1,216,813 548,236 046,050 503,748 ites 953,005 1,235,253 946,051 509,623 455,952 41,9 1,270,325 XVIII. 946,052 509,635 636,065 641,054 At rl 1,338,506 964,919 514,931 951,046 648,597 Betis 1,382,196 415,088 Q71,111I 515,381 951,047 650,292 VI. 1,395,238 998,139 071,112 516,380 951,048 653,278 1,419,500 1,023,977 980,251 534,539 951,049 653,670 409,384 488 DIGEST OF PATENTS a EE aE ESE N ne eee GRAY Acid XVIII. XVIII. Developed 493,564 euge 968,697 495,873 960,182 985,767 III. dager sbeebs ve 515,339 968,533 985,768 pearee 1,005,405 673,640 516,203 970,278 985,769 668,445 ermcetae Basic VI 516,203 971,224 985,770 723,125 Acid . Boe 975,863 1,005,140 556 30,079 1,005,141 863,397 Mordant XIX. eee hea 542,073 : 996,109 16h 6ee V. III 423,050 536,879 556,164) vegas i eee r 8 672, z : 6 68.084 stir as die! 571,933 1,044,933 Vat 73,640 adoas Basic XVIII. 603,646 1,047,940 XV mee Mordant 1,099,676 1,052,520 : yi: 623,638 4 9951494 1,270,290 1,169,404 668,445 Direct Reducing 1,464,079 560,334 515,339 790,079 420,311 Vat 779,860 672,714 oT VI. VII. 961,387 958,912 oh 449,629 at 941,152 | 1 ee: 1,402,350 958,912 454,535 476,393 767,259 954,273 | 1,151,628 GREEN Acid 1,021,364 Acid 1,237,193 661,800 Direct 893,8 ’ ? ’ ’ ’ 93,537 1,021,365 Mordant 1,242,536 664,450 ora aee III. 1,021,366 1,394,823 III. 992,567 1,199,233 III. eb pee 993,735 555,904 1,395,823 X. 154705555 631,605 * 993,736 599,426 xX 348,613 362,835 XIX. 648,331 995,936 599,427 ; 3991479 548,236 Graibor 1,022,781 or ’ Bee | sveme | derek | fe | comer 623,219 476,491 . . 1,052,507 623,220 555,904 eat, Developed ; 1,052,520 640,986 >a 0 569,405 : 421,040 1,093,427 548,158 ee spat | Biol | VE | Gs | sea “pleats 1,138,670 SOG 807,181 fo ” S42 sores, | Gores | Gort | ee ’ ? 0 , > ’ 675,573 XVIII. 617,981 pil Cnt FS af 563,384 1,207,982 687,657 623,219 XVIII. outils: 585,104 1,216,134 688,576 412,61 623,220 ‘ 591,616 1,396,483 707,373 Bae 3 631,605 501,104 980,251 603,645 1,464,598 715,662 2 the a 648,331 999,028 980,521 603,647 1,478,027 723,125 ere 654,295 1,460,315 988,000 606,439 729,073 ; 673,691 993,549 627,679 VII 734,325 ae aad 675,573 XIX. 1,006,051 628,233 j 738,614 615,472 688,576 1,021,364 655,013 647,280 5547 617.6 47; 778,036 615,485 7075373 el 1,021,365 950,404 699,581 ei arbee 623,346 Shed ied iia on 1,021,366 974,346 872,227 12,684 729,073 3 980,521 cea 826,750 Bees 734,325 si pps, a5) 988,000 360.008 ate: 8,61 1,024,081 I,00 900,09 996,487 630,976 738,614 6 2009745 1,001,457 Pee che eee 778,036 67,486 1,101,739 1,024,080 1,101,7 8 1,207,981 ead 812,599 Basi 1,150,656 1,024,081 rte 1,280,648 766,359 812,684 asic 1,150,675 4,802,790 1,444,277 886,815 996,487 VI 1,193,829 1,126,656 1,466,687 VI. 891,888 erates ; 1,199,233 the Br) 891,889 VI 613,920 1,237,192 rahe eee Sulfide 514,599 980,251 1,416,621 1,241,183 4) Gieae Vat 562,200 980,521 1,416,621 ee 563,384 999,028 464,77 ye ages: XV. 627,783 1,021,364 ge rid eons XI Reduci ; 646,711 1,021,365 585,104 423,341 Vat” 653,670 805,918 1,021,366 805,918 1,470,555 86 695,533 843,077 1,101,770 843,077 eagee III 698,555 879,053 1,470,554 961,354 Basic 729,874 906,421 1,478,015 1,155,765 Mordant sigh ons 739,145 731,669 932,813 1,478,039 1,217,042 6 : 8 7753397 741,030 958,830 1,219,954 950,458 8 961,354 XIX. 1,221,849 AVI: 1,021,364 z Yeak toe BE 980,251 1,234,994 222,257 1,021,365 Saree apa 993,549 1,054,247 1,237,192 266,912 1,021,366 876,190 843,156 s COLOR INDEX GREEN—(Continued ) 489 897,8 1,054,888 ee ce me | caper 927,868 1,081,599 1,251,368 1,076,8 gopaet . 1,081,600 I 251, 6 ITl. ah te 807,182 1,478,039 9345303 92515399 958,640 1,083,489 1,261,394 a gee 1,093,259 1,314,929 348,603 XVIII. XIX. hapless 1,100,877 1,405,446 615,232 901,53 1,102,171 1,440,833 1,090,123 1,031,823 661,800 1,054,247 ORANGE Acid 1,233,742 Basic 1,024,0 5233, 5024,031 5455333 1,342,134 678 1,270,325 Mordant 1,025,983 611,663 1,362,936 1,082,898 III. 1,314,921 1,025,984 631,610 1,365,706 1,243,170 9.35,506 iG 1,032,797 631,611 Meee? 6 1,407,711 £052,135 644,462 Mil: ee 70° eee 1,074,429 662,122 XII. x 510,577 1,078,503 663,498 VI. ey 1,078,504 675,629 656,858 852,158 43,509 1,094,448 675,632 : 211,671 740,4 1,126,489 677,517 22%,120 ALI. 746,981 1,128,813 678,423 601,063 XIII. 225,908 766,540 1,147,803 763,761 636.065 8 251,162 1,026,257 794,052 T,US3,355 889,016 weg eeak 52,158 207,852 1,005,176 1,133,370 902,186 sae 310,155 Acid 1,255,740 1,185,413 903,284 951,048 XV. 329,634 Mordant 1,418,852 I,210,808 916,161 ; 333,042 1,215,359 935,018 , 746,926 531,975 XIX. 1,270,325 936,367 Reducing 760,110 601,063 III. 1,314,921 959,109 Vat 895,637 659,497 625,536 1,338,397 982,507 896,916 716,289 702,445 1,338,506 993,073 III. 899,456 719,048 Developed 1,342,134 995,160 ie 719,049 1,362,036 999,944 1,115,1 724,078 vi. VER 1,365,706 1,001,183 sees. 1,251,368 767,070 1,405,687 1,006,929 993,992 787,767 221,117 241,661 1,453,660 1,015,375 999,798 Lake 798,098 225,120 631,610 1,457,114 1,024,031 : 022,781 VI 879,552 297,852 678,323 1,025,983 1,023,248 c 902,186 Ase 679,172 XIII. 1,025,984 1,025,195 8 6 943,536 Eee NS ee 1,032,797 | 1,034,895 ee te 949,633 Soar iret 852,158 | 17951859 | 1,044,603 a ‘ aye 718,028 765,080 i 1,052,031 1,052,480 860,575 he 7 870,552 865,587 Direct 1,052,135 1,087,243 912,138 989,954 936,367 879,552 aie? 1,067,881 aeaor: 914,146 991,750 943,536 889,016 1,074,429 1,067,046 935,371 993,549 1,014,114 914,144 VI. 1,078,503 a akg ae 959,078 1,005,233 1,210,808 916,161 1,078,504 eer 1,022,612 1,014,114 1,216,812 949,633 375,930 1,094,448 foanees 1,028,493 1,126,489 1,216,813 982,507 395,634 1,147,803 1,419,302 1,034,853 f 128.813 ae 991,750 401,483 1,153,555 115156 1,314,921 993,073 430,534 1,172,061 : 1,172,061 1,292,385 8 Oil and alc eee Bean cn6 993,549 447,303 1,183,37 VII a x4 1330,50 999,944 497,032 1,185,413 : Sol. 1,216,760 1,314,921 1,001,183 500,761 1,215,359 VI. 1,216,812 1,338,397 1,014,114 519,523 1,292,385 872,585 1,216,813 1,338,506 1,015,375 524,261 1,338,397 915,346 1,314,921 490 DIGEST OF PATENTS RED Acid 313,118 84 35137 XIV. P ae 314,938 843,149 si bar od at Basic ; 314,939 843,756 386,709 779,82 1,302,19 Mordant 6 8 329,634 846,511 Ra66 : xX Ape 332,528 863,290 XVII 826, a ve a oe 332,830 865,252 Me Bote saarge 333,038 865,253 8 + 3 440,359 666,095 ore 333,041 879,552 250,201 Spteey | 709,187 656.463 333,042 880,292 250,247 eee XVII. bir as 659,565 333,257 887,348 262,680 a pete | 716,264 65955 334,257 902,186 318,484 < 9123 262,680 766,540 8,576 344,971 906,421 333,049 siege 603,300 794,052 707,374 357,274 043,536 421,049 1,446,163 609,598 1,418,852 763,233 376,392 949,633 473,453 877,052 1,455,486 779,825 380,928 961,355 603,300 VI. 877,054 B06.054 441,045 982,952 701,427 947,876 Vv. glad 447,189 982,053 877,052 213,563 976,417 Eoeapee 454,645 982,954 877,054 213,564 978,799 543,894 ee 456,627 982,955 887,620 221,118 hese oo hhpeercd 75,390 456,807 986,287 947,876 256,380 999,028 559,062 932,290 458,283 980,054 950,359 207,852 1,023,977 559,063 958,850 458,284 993,549 076,417 314,9 592,608 994,803 466,841 1,008,907 978,799 senee XIX. 995,306 468,142 1,012,055 978,800 441,045 VI. 1,026,557 493,583 I,O014,114 980,251 458,28 573,299 1,026,621 500,762 1,023,199 999,028 prey 1,002,825 221,118 1,037,410 512,116 1,024,308 1,006,738 ORaee 1,055,864 602,637 1,062,990 515,764 1,042,198 1,023,977 512,116 1,055,885 626,935 1,086,123 525,057 1,054,348 4,020,059 631,685 1,403,888 531,07 1,075,30 1,219,166 VII. Vv. 558,613 eae is Basic : 561,615 1,113,622 XIX. 704,826 913,513 425,530 563,383 1,123,430 718,028 t 430,975 610,345 1,126,489 739,069 XI. 431,404 617,963 1,128,813 ees 787,046 516,588 Ee eke Wel ee Cae: Rowe oats hae 377,349 ’ 59,49 1,154,826 : 7 . 377,350 | Sees | ere | Sil | Rs 690,204 1,199,890 pyegak B06 ae Sa XIII. 204,799 695,238 1,201,544 eaett I 826 281 240,136 Re. 9,144 695,811 1,201,808 646,794 826. 28> 466,826 257,917 210,054 700,565 1,216,760 esog ih 827,468 567,473 pe ato283 704,825 1,216,813 apie 841,371 $98;508 XVIII. e. 9,986 704,826 1,233,742 yr rie as Spans tA 7 eons Re. 9,987 713,507 1,286,411 i He hs 50,335 211,180 716,289 1,314,921 Acid 843.1 ws 53,241 eae by hip) 1,316,781 Mordant 843,756 Sons 248,154 »071 722,71 ees ets : 02,037 213,563 724,078 a ari II. eevee St 6,352 283,766 213,564 727,962 1,358,007 865,253 879.424 310,128 224,927 727,065 1,359,069 : 6 879,552 Labeisigee 316,471 224,928 727,966 1,382,196 34:07 887,348 1,074,046 471,638 225,908 737,967 15393.712 924,232 1,087,427 580,766 233,465 739,069 1,395,238 Ill. 933,841 TAS 2 aS0% 602,637 242,707 741,930 1,408,405 936,367 609,598 246,221 754,315 1,419,500 95,465 043,536 aN 661,800 246,272 761,123 1,429,782 97,597 049,633 664,450 249,926 778,476 1,467,711 127,426 961,355 780,741 913,513 250,038 787,767 153,536 964,768 913,514 251,163 787,768 VII. 154,153 983,132 XX, 947,918 soe 790,364 188,061 986,287 949,906 ee 792,032 677,239 188,217 1,012,055 402,436 1,023,977 eid 792,034 891,690 446,893 1,014,114 425,504 gd 797,441 500,917 1,114,771 445,684 XIX. 56,37 7975731 X. 569,404 1,127,261 489,623 256,380 7975732 560,418 1,210,808 16,588 256,401 803,592 00.8 aide 510,5 425,504 300,874 646,795 1,216,81 516,58 oeR tre NAT pgs Re 3 »589 425,684 ee me Pais 650,756 ree oe aa ae ieee ’ 20,2 ? ’ 268,507 826-281 gore shied + ph 578,578 516,585 , 440,359 656,463 1,286,411 584,119 16,588 277,182 826,282 466,852 675,574 1,314,921 &. Sieg eRthae 827468 1314, 596,333 516,589. 688,576 1,316,781 613,926 8 meta ee tae XII. 797,373 1,323,285 625,641 78,578 ‘ 1,371 ‘ : 302,970 842,548 808,919 At et ee es ap oe eke ’ > ’ 3035335 843,077 1,026,257 763,233 1,338,414 821,452 fie Bl . . é i z 7 COLOR INDEX 491 RED— bas (Continued ) 536 625,6 999,2 yey ree 980,251 643,37 1,014,11 1,023,977 588,180 fag. ; 1.018, 4 1,026,08 588,18 1,024,308 45,781 2015,375 ,009 y1OI ’ 656,426 1,020,670 1,219,166 588,182 1,024,794 791,869 86 694,149 1,022,287 588,203 seabsse2 875,390 Slane 605,441 1,022,288 Direct 593,347 pn Oaae eal die 716,264 1,023,199 apeeihe Pe de Ed 939412 net ioe 738,227 1,026,902 IIT, pa cee gigas ake ee gee 821 1,032,7 22,961 041,146 928,891 2949 9452 I 97 62 I,051,8 92 876,3 D 3033,310 675,574 6 5,174 ae 3059 Pane 877, 39 eveloped 1,042,356 1,327,260 bie bio heat 459 entees I Reras® eae? Poets Li 887'6oo . 9052,137 VI ,O2T = 9137 97 OL 8 ’ ae 1,058,562 : alte 1,058,502 935,827 eee 076 1,058,692 3,498 ,058,692 35,878 897 : Jeb larttes 221,118 666,867 1,065,950 038,565 eee 646 1,074,429 56,375 675,629 1,071,833 950,344 5738 uae 1,075,305 Oe Sk: 675,632 1,074,429 955,105 99,152 VI. 1,078,504 tc ,380 677,516 1,074,946 957,039 910,839 1,082,925 a779102 677,517 1,076,756 957,040 915,346 211,525 1,087 59335 678,323 1,078,504 957,041 916,029 241,661 1,0 pare 329,632 679,9 1,082,92 957,0 916,030 404,097 Rooted 329,033 087.171 13082,925 057,125 923,959 578,580 1,09 342,432 700,565 1,087,430 961,047 949,592 588,181 Renee 344,971 718,032 1,092,842 961,612 963,813 588,182 1,122, 3575274 718,389 1,094,448 970,278 965,170 588,203 speree?: 359,576 724,894 1,098,388 986,521 para bt git | fact | Heat ee | baeee | Be pe 39,042 1,128,8 1806 79,177 1126,656 93,735 mares 6 ,O13 362 I 1,074, eroca | 1188825 2 ae hg Uressss sag 1308,778 Se hs ie lee 365,666 pea es Tere spre porate Pre a fos.812 rere ser 365,667 806,0 et aes 1,004,4 1,147,778 695/812 | 1'160,408 375,848 807,110 185,41 net ot tet Seseyet 718,028 eee bipan 380,067 ee Paib ex 1,009,081 Ageia 718,032 i eBe at beaten 813,155 I,215,359 1,010,463 461,435 722,715 1,188 $46 Sp ee 837,736 1,232,056 nat cs Sulfid 722,716 Tiger 301,132 839,360 1,282,354 1,011,068 ide Vat 724,078 aes hos seat: oleae 1,283,206 T,014,204 XV 727,962 1,215,359 : 9,127 Siem 1,292,385 epee : 727,965 1,232,056 94,425 873,798 93395397 Does 523 macs | tales | Bi eet ee are saat See gee 401,483 886,095 iesese 1026 5688 723,448 oie 1,316,781 404,331 888'so0 1363-886 1,028,6 818,980 770,1 z 1,323,285 406,669 888,8 1,365, 6 ama ey 829,740 778.476 — 410,057 889,016 114721333 ga lia oetene ’ ’ Mee | ate | Geek | Belt rapeaie | aseese | Hestzi 790,364 1,342,134 ce, 4 3,284 x pied ged 1,098,2 5 7975441 1,362 2149 912,182 VIII. ’ 3 »589 I,1I u 59 806,41 1936 416,145 916,16 1,047,831 115,188 807422 Gecgah 47,207 916323 318,48 71050;820 1,128,368 813,155 des ad eh 931,423 aN beet 28 1,129,875 ‘ ’ 423,56 931 : 1,065, 3129,575 a edhe 1,419,500 eh ds Le OLE: puttaee seer PE 1,261,304 Slegs340 aay 429,350 9330447 ssa 1070,106 1,452,005 ’ 4 ’ ’ gest wssio6o | aazrdo | agise2 |X 497 | Prosioos 147 4150 3,290 XIV. 2045 3562 xX ’ 3004 La ae sib) | bano8k vases | an 887,348 4551952 483,308 943,470 3775349 1,133,081 ae 889,016 XV 498,303 978,580 ae ony 1,162,496 1,090 ante | Bere | pases foes | bas726 Ag F, ’ ’ 2 m 916,161 829,740 516,756 982,952 pi se 1,285,727 916 16,75 989 ’ 9329 ed XVIII. $10,522 ear ee eat aae ds 941,088 19,523 999,230 Hthg VII. VI 949,633 tes See ede ie pe : ? ‘ ’ I 00, ’ ge 88, aoe 532, 6 91740 645,781 ral 650,747 ees ed 20 eeu »012,055 aa 690,294 982,085 9761417 $35,037 | or.a75 Reming 10.348 | Gg9181: 993,549 978,799 555359 5020.6 3 841,003 yee 978,800 572,723 ae 848 Te 578 1,022,28 IIl. 1354 718,356 1,022,288 9355 724,743 186,032 850,827 724,894 867,305 728,388 728,455 492 DIGES T OF PATENTS RED— (Continued) 733,280 g 30,312 741,029 8 ? 9 37,128 32,289 743,0 978,86 tgs 858,065 aca paatves eee XI Oil and 757,109 eae ees 983,486 scr ; Alc. Sol. ’ ? F 730,716 Sorte, 942,916 1,001,286 1,073,784 1,065,063 VI. 765,079 872,181 954,960 1,001,458 1,073,902 402,980 770430 878,96 955,068 1,032,055 ee waht th peda 786,767 888 81 964,786 1,014,539 gab ei XVIII. 789,096 oeoet “ 1,022,61 _ 1,073,951 661.8 792, : 908,580 964,918 I O28. 1,097,231 agate 307,401 ohehes 911,186 964,920 Phases 1,145,072 oe 589,766 ye peeaar oe ee XIX ggesior »401 1038.884 1,314,921 : XIX. 1,358,007 613 11 113 1,381,503 VIOLET Acid Pees 547,17 III. 41,936 9173 6 754,856 Neg yas peers 531,148 617,08 765,581 238,870 655 x5, 547 329,636 648.3 I 767,070 66,594 Bien 353,264 Goad 656,081 778,476 XVIII. ast 856.537 77279 | 947,918 656,463 792,032 7 ’ 3 863, 949,906 91 ’ 49, 3907 1,02 666,594 ‘heeded leet eet 893,855 XIX vous pase 523,703 346,022 763,233 Bat 1,402,195 432 ; : 77 2,8 »040 7291073 pices Ce. Tote | eee 41p048 | 2 3 ’ ’ 1,0 : 613 ’ set ety sees ees | ree || can 35233 Raa 498, : gees | 8437 sie | vt | Dereiaeae _os8,830 | Baa.zse Sonast | 42072 | 304708 Basic I. Foneats 843,808 611,628 420,374 Se Mordant 1,139,540 ene ase pe pis WI 134,076 Vv. 899,171 877,052 634,005 ya Be VI. 901,676 947,876 piece 877,052 503,295 940,354 912,356 950,359 eae 877,05 583,439 Vv 921,105 976,417 792,032 047,8 3 IV. 588,181 I. Re. 13,121 978,799 pete e aioe 603,008 921,239 978,802 35,539 EEE pope 677,279 608,999 356,672 Re. 13,122 980,251 839,489 I,o1 1799 689,025 610,349 381,045 935,031 986,287 841,371 ape bs 5 613,646 yi046 961,354 995,494 843,077 15034,173 V. 650,619 454,645 982,954 1,023,977 843,137 1,042, fe 664,955 456,627 ances 1,042,498 843,149 erpese 369,764 676,495 456,807 986,287 1,065,405 431756 1,065, ‘ 418,916 677,227 408,142 roaea6e Re. 13,069 865,253 Re. ieee 458,281 677,228 476,335 | 17014,039 1,217,238 887,348 ee 677,229 525,056 1,024,308 1,218,232 933,841 11375,701 VI. 677,230 546,068 1,028,006 1,219,166 935,031 iets 677,231 583,439 1,052,262 1,387,596 961,354 bt ot 221,116 692,675 5935347 1,054,348 986,287 sei 4 602,640 692,676 602,640 1,078,925 XIX pron doe XIX ' 710,05 paras 1,106,781 é : rie ‘ XI. 7i8vaa8 065 I,126,48 09, ’ 771 *< 2 655,520 sbiarteaa: 9,997 1,127,261 1,003,257 396,87 a 664,955 1,216,760 Acid 1,234,994 Basi mee 727,963 671,896 1,237,183 Mordant 1,242,536 : 985, : 727,965 677,227 1,325,841 1,292,385 V on 727,967 ee 1,359,969 Il. eee . XVIII 729,601 77,229 | 19375970 338,414 248 741,936 677,230 1,382,196 134,076 1,426,189 oe 754,836 677,231 1,395,238 Il E eaete Ped see = 10,059 1,402, . uh: ’ 2 ’ 6 725,848 /4t9, 800 446,892 VI mie: bee 726,695 1,429,782 446,80 252,273 i pr 778,476 727,963 496,1 S 252,273 6 or os 807,422 727,965 XI »T39 253 02,640 97,415 8 z ee ; ae ere 879,424 arate Sseees 728,021 4% 440, 308,748 839, : 920,601 440,359 509,439 ceraie XVIII. 325,827 ie 531,148 6 7,951 518, 3 325,828 8 3,077 43,451 045 329,636 43,137 524 ) 43,066 8 1235 290,892 pane 887,348 471 ’ 1638 912,356 COLOR INDEX 493 VIOLET— (Continued ) 916,323 XI. 468,049 1,009,796 707,813 VII. 779,860 920,151 483,368 1,009,797 931,598 760,167 935,031 1,138,670 493,563 1,012,960 ‘ 836,309 796,443 982,954 516,758 1,020,670 Reducing 848,356 818,980 982,955 XV. 516,760 1,020,756 Vat 872,115 821,378 999,797 521,096 1,024,308 876,158 829,740 1,003,26 778,713 534,573 1,038,209 III. 877,743 915,385 1,009,796 829,740 543,212 1,038,210 he 931,598 1,009,797 §57,43 1,049,109 647,280 894,00 960,919 1,014,039 XVIII. 563,386 1,052,136 781,085 898,452. 1,129,574 1,020,670 576,511 1,058,562 809,892 899,994 1,471,150 1,028,006 877,052 588,180 1,079,415 818,336 904,867 1,038,209 877,053 588,181 1,113,468 818,992 916,030 Lakes Re. 13,550 950,359 593,347 1,160,406 837,775 041,152 1,038,210 976,417 602,540 1,169,329 867,679 947,030 III. 1,052,136 978,799 603,008 1,209,154 906,367 955,699 1,052,262 978,802 608,999 1,210,751 935,827 997,260 10908124 1,056,080 980,251 611,507 1,282,354 938,565 1,001,919 Bae 1,058,562 995,494 613,646 1,282,355 938,566 1,050,179 V 1,078,925 1,023,977 656,619 1,282,356 950,343 1,051,856 : 1,079,415 1,219,166 671,896 1,292,385 950,344 1,108,056 1,113,468 676,495 1,338,414 957,041 1,108,057 418,916 1,126,489 Direct 687,171 1,342,134 957,042 1,144,577 60,406 692,675 1,472,333 961,047 1,147,778 VI. 1,160,40 boo kre 1,169,329 VI. Oa97 1,472,334 961,048 1,243,170 Say 724,893 970,278 1,444,277 420,372 1,209,154 724,894 VIII. 724,894 1,213,07 344,971 6 9935735 Iphid 8 1213,075 360,792 759,613 261,518 993,730 Sulphide 20,052 1,325,841 365,409 7705177 1,003,268 Vat 964,920 1,338,414 380,067 807,422 XIV. 1,014,204 1,003,266 1,342,134 380,098 860,221 1,016,604 XV. 1,016,307 1,375,701 401,483 Hla 350,230 1,032,216 1,073,905 1,382,196 406,669 775044 XV. 1,038,589 608,354 1,073,951 1,419,500 423,569 897,529 1,044,603 651,122 1,097,231 hes 440,639 898,217 608,354 1,047,812 656,631 447,302 er 656,631 1,047,813 665,726 mele 454,645 920,151 1,058,604 701,435 Vit. 456,628 9335447 pe Soe 1,062,075 7775323 396,574 462,824 999,797 32,965 1,128,836 778,478 410,733 261,518 464,566 1,009,741 471,638 1,200,848 G7os753 420,164 YELLOW Acid 798,098 1,216,813 Xd 980,251 431,297 XVIII. 839,605 1,270,325 999,028 452,197 III. 840,690 1,286,411 6 1,430,899 484,521 415,088 849,739 1,314,921 bale 528,965 603,300 621,679 879,053 1,338,506 ermeee Acid 555,058 999,028 656,463 880,203 1,447,485 59593 Mordant 626,913 XIX 1,062,990 901,675 935,370 695,238 : 1,076,249 902,186 VII. 935,829 III. 718,020 6 6 935,830 pte 906,422 ee 739,069 702,445 VI. 961,355 540,564 His des 348,613 818,981 1,055,864 965,882 994,988 972,951 443,402 936,367 “eben 978,438 982,050 452,210 961,354 210,233 978,439 IX. 1,010,919 618,000 961,355 Basic 211,525 980,251 1,098,600 619,574 1,075,134 211,671 980,521 225,108 1,109,919 621.679 1,114,750 A b. 329,908 984,900 2445757 623,069 1,127,234 253,598 987,999 256,379 XIII. BREE 1,127,261 1,418,852 289,613 ; 283,265 z 991,750 656,463 1,149,231 297,852 289,543 1,210,808 VI. 1,003,293 8 290,585 702,445 ’ ’ 333,035 1,028,139 sours 890,588 1,026,621 1,216,812 333,039 1,041,919 324,615 90, 1,216,813 aye 380,928 roe 333,036 1,197,632 SG 341,99 1,054,348 ge IV. 1,204,004 344,075 pet 1,075,305 . eee XIV 1,283,296 602,638 71544 1,084,363 743577 . 720 920 1,286,411 879,424 695,238 nea 6 1,059,571 , 113,022 1,314,921 902,021 719,048 6 1,162,109 719,049 1,157,109 1,299,171 395,115 VI. 1,338,506 1,087,427 739,065 #n186,346 1,349,802 1,474,587 739,069 1,172,061 1,380,186 XVIII. 253,598 XIII. 791,524 1,199,890 1,393,714 297,852 IX. 791,525 1,210,808 1,396,001 308,912 309,882 256,599 791,526 1,216,812 1,413,914 603,300 424,019 1,162,109 290,585 494 DIGEST OF PATENTS YELL ogee OW—( Continued) XVII. VI : 1,157,169 468,549 412,979 221,115 epetaeh! 588,180 cavans 1,065,440 III. ees 515,100 Dare : 619,518 406 1,070,196 446,009 602,638 rat 1325 622,961 shel 1,087,293 4a XV 626,913 2314,921 656,120 4 brie 1,089,221 1013 III. 1,338,506 663,498 per ees: 1,090,621 VI oa XIII. sean 806,077 ao 1,096,731 . 90 1,405,687 902,186 1,120,475 1,232,551 290,585 935,016 Pes 1,196,127 714,883 x XIII. 935,017 i166 1,209,163 844,845 IX. XVII. ah 935,018 6G Ce 935,371 115 936,36 1419,302 971,76 piricas 412,078 et necuee 1,431,656 eg 33,883 xV XV. 971,762 . riges 1,001,286 475,0 Basic III. uer ase spony III. 478,061 1,051,565 Mordant 283,766 738,027 999,230 730,1 XIII. 1,059,599 1 395,080 XVII 999,944 £08 765 ewe . 664,450 I. 1,001,183 Ss6sg0 852,158 We cc 1,012,853 a9: 9050,155 8 ’ 8 37,8 (8) wea | ne, |” ee | te | ea noon 526,577 Cree XXII. aagaae ee VII ae 546,177 eee 406,952 ee 922,282 : 1.266608 617,340 ; . 1,078,503 chap oF 1,074,850 1,314,921 619,577 Developed Direct 5.098 bo4 935,827 637,183 rekdone 935,878 XIII. IX. 643,569 II. I. 1,082,925 eb: 852,158 1324 1,087, ’ 763,756 666,0 382,8 pea gh 938,618 x 666,006 7395145 832 1,094,448 938,619 Me 932,266 675,568 VI VI. 911 4,044 941,320 561,276 955,080 yooares d 1,125,073 957,040 561,277 1,051,565 712,421 211,525 221,115 1,125,074 957,041 OT2.7 47, 1,059,599 716,084 aat.o6t 221,117 1,147,803 957,042 718,342 1,076,819 716,264 718,028 329,638 1,153,555 ae 722,630 1,086,155 7395771 765,080 329,639 1,159,386 i: ee 738,027 1,091,148 739,117 879,053 360,792 1,160,471 es, sie 7731346 1,166,808 740,468 980,251 380,067 1,172,061 paonee 782,905 746,981 980,521 380,098 1,210,751 onrak 785,675 | XII. 1,005,176 987,999 380,403 1,283,296 1,004,433 he 5 1,255,739 991,750 380,928 1,362,936 1,009,981 So a4en 9351370 1,255,740 ie 386,192 1,015,329 892/456 988,870 1,418,852 eons 396,204 XI. 1,076,036 896,016 1,427,431 ai asies 398,990 ue P NOLeeay 899,845 XIII. 1,455,486 1 24.0 : 401,024 se 9057 yee ree 904,809: 1,455,487 poeee. 401,634 56,859 ae 96 996,485 852,158 1,455,488 $ 9135 406,670 658,593 np »003 1,061,714 059,670 428,629 9042,931 1,100,877 XVIII. IV. 1,075,305 430,533 XIV. 1,044,602 1,115,188 1,078,503 430,535 ey OE 1,115,189 763,756 201,802 1,078,504 454,840 350,229 one 1,140,745 1,232,551 488,430 1,082,925 472,121 360,553 mB TS 1,440,833 ; 720,920 1,094,448 500,761 395,1I5 1,052,480 vI 1,114,844 515,807 396,527 1,055,287 Lakes 3 V. 1,123,263 516,468 613,911 1,059,607 Oil and 1,147,803 ep tea 636,065 1,062,975 I. alc. sol. 543,784 1,153,555 519,523 951,046 I 062, 88 524,262 951,047 bro 1,427,431 ’ 1,065,102 1,427,432 409,384 ’ 243 1,314,921 COLOR INDEX 495 VARI-COLORED Acid 1,314,926 1,259,499 X. 357,274 1,457;235 630,952 1,414,614 1,292,385 te eed 1,314,928 Y 420,311 390,79 irec ve Ix. 1,314,921 380,067 ea P 1,314,926 XVIII. 380,098 VI 1,346,154 1,340,69 1,059,571 1,414,614 380,402 . fl 1059, oes 350 segtoe 636,065 Lakes ‘ : 1,355,04 380,927 : XII. XVIII eee 401,483 ied VL Beles: 808,919 609,599 stad 438,657 951,048 221,119 1,026,257 999,028 VI. 421,640 1,314,921 225,908 423,569 XIV. 420,634 XIV. Basic 211,525 430,534 XVIII. 333,042 241,661 454,645 636,065 947,661 386,709 V. 517,533 462,824 951,046 1,232,551 357,274 588,182 oe 951,046 ee pours 980,251 VL 588:203 eae Reducing dtc teal 454,645 999,028 710,059 sbdkicid Vat , 456,627 ; 718,028 543,212 ’ 341,991 6 6 VI. 456,897 Acid ali i 563,38 III 541,859 M rd t Biases 980,251 588,180 ‘ 710,059 Aas Becton 1,052,135 588,181 ids 1,314,921 716,289 VI EsSt Ass * a ple 588,182 5s a aa 1,314,922 8 " 1,314,922 ate sh 04, 588,203 ayes 1,314,925 795552 1,183,378 1,059,607 02,186 887,348 297,852 1,314,925 1,210,808 hia 1,123,390 902,186 380,927 1,215,359 903,284 1,437,783 Photo Sen- - 906,421 424,019 XVIII. 1,314,921 933,447 sitizers 832,813 493,413 ; 1,414,614 eee pes VIL. 980,251 18,028 1,232,551 1,052,13 XIII. 1,024,308 if 1,232,552 XVII. 1,067,881 1,243,170 1,052,262 oleae 1,183,378 752,323 1,054,348 sit haa Basic P0254 1,210,751 Suifide 805,143 bak 465 933,841 Mordant 1,215,359 Vat ; 1,216,7 Direct 1,338,346 1,216,813 1,210,808 1,282,355 3 1,259,499 1,216,813 Vie vr 1,292,385 XV. 41331349 1,314,921 1,221,849 1,314,922 1,374,871 1,314,922 1,233,433 626,935 344,971 1,314,925 549,036 1,374,872 INTERMEDIATE INDEX. Intermediates listed in this index are those given in the patent abstracts as materials used for manufacture of dyes or other finished products, except Group XXII, in which methods of manufacture for intermediates themselves are given. The chief function of each intermediate in index and abstracts is shown in bold-faced type. Ring compounds are used as chief functions except derivatives in which a primary function exists in the side chain, such as phenyl glycocol, in the indigo group. Numerals multiplying the chief function are included as part of the index name. Diphenylamin and triphenylmethane, for instance, may be found under “D” and “T” respectively. The order of index compounds is from simple to more complex, regardless of figures for position numbering. That is, 2-amino phenol is followed by 3-amino phenol and by 4-amino phenol, before more complex compounds; 2-naphthol follows 1-naphthol and both precede derivatives of either. There is but one exception in the alphabetical order of chief functions. Amino naphthols and derivatives are not indexed with naphthols, since the method of numbering commonly employed is based on the position of the NH, and not on the OH substituent. That is, 2-amino 8-naphthol to be correctly classed as a naphthol, should read 7-amino 1-naphthol; I-amino 6-naphthol should be 5-amino 2-naphthol. Esters and ethers follow immediately after the acid or phenol. Letters in parentheses refer to subdivisions of abstracts in Group XXIV. For general pro- cesses see Alkylation, Carboxylation, Diazotization, Halogenation, Hydroxylation, Nitration, Oxidation, Purification, Reduction and Sulfonation. Abietie acid: VI. 1,414,614. Aceanthrene quinone: III. 1,216,134. Acenaphthene: XV. 1,358,490. XXII. 1,439,500. 4-Oxy VII. 998.596. quinone VII. eit 904,867; 91513405 a 905,170; 1,001,919; 1,061,596. XXII. 1,439,500. ; Acenaphthenone: (See Acenaphthene quinone). Acetaldehyde: XXII. poe 11306,9633 1,421,743; 429,050; 4373403 MRIV. Uh vekooes) Acetal, Amino: XXIV. (m) 1,432,291. accceraan TX. 759,657. Chlor XV. 688,999. eaeny ethyl oxy XXIV. (m) 1,375,949. Acetamidin: Diphenyl amino thio 647,281. Iso nitroso diphenyl 647,279. Acetanilid: XV. 636,066; 687,072. XXII. 574,395; 574,396; 578,384. XXIV. (m) 543,214; 615,828; 615,820. Aceto VI. 617,544; 990,173; 1,028,139; 1,082,719; 1,086,155; 1,125,074; T,150,350s55 1,210,512> XXIV. (m) 503,748. Aceto, 4-carbo VI. 1,125,073; 1,526,413. 3-Amino VI. 1,023;120: 4-Amino VI. 462,414; 599,532; 697,765; 969,450; 1,014,633; 1,014,984; 1,020,670; 1,074,429; 1,087,429; 1,090,379; I ,283,2313 1,378,388. 4-Amino, 3-sulfo 1,024,080. 2-Chlor aceto- VI. 1,051,565; 1,059,599. 3-Oxy XIX. 694,149. Acetic acid: XXII. 505,787; 596,043; 667,358; 715,748; 1,306,963; 1,430,304; 1,449,918. XXIV. (m) 801,158. anhydride TIL, 8§3;04 5s VII. 618,096; 690,332; 690,346; 778,725. XXII. 683,464; 1,298,356; 1,306,963; 1,311,158; 1,338,979; 1,368,789; 1,403,920; 1,425,500; 1,429,650; 1,430,304. XXIV. (m) 710,005. ethyl ester XXII. 1,425,625; 1,425,626. phenyl ester, (See Phenyl acetic acid). vinyl ester XXII. 1,449,918. Aceto-, ethyl ester VI. 818,981; 1,051,565; 1,166,346; 1,270,325. XII. 658,593; 982,050; 988,870, 1,098,600. XXII. “4,425,626: XXIV. (¢f) 743,305; (m) 307,399; 1,419,092; 1,429,922. INTERMEDIATE INDEX Aceto-, iso propylidene ethyl ester, XXIV. (£) 743,305. Chlor VI. 658,506; 671,902; 671,903; 671,904. VII. 540,564; 617,651; 619,884; 620,442; 621,652; 622,139; 699,581; 712,190; 818,341; 823,294; 841,456; 850,827; 867,305; 867,679; 868,294; 872,085; 877,702; 877,743; 881,158; 881,159; 881,624; 888,852; 892,897; 906,029; 1,001,457; 1,243,170; 1,419,720; 1,442,743. Mel, 15359,071. XXIV. (m) 624,772. Chlor, ethyl ester POPE 2 1,303,101. XXIV. (m) 1,086,881. Dichlor VII. 310,604. a-Diethyl amino ethyl aceto-, ethyl ester XXIV. (m) 1,429,992. Oxal-, ester — XII. 627,690; 935,370. Oxal-, phenyl ester XXIV. (m) 543,579. Acetindoxyl: VII. 899,994; 960,008. 2-Acetoluidin: VII. 867,679. 4-Acetoluidin 3-Nitro: VII. 867,306. Acetone: VI. 700,565. VII. 257,814; 257,815; 276,890; 540,427; 662,073; 677,239; 726,688; 1,412,038. XXII. 608,019; 648,389; 690,724; 1,411,529. XXIV. (pl) 1,397,144. Acetophenone: arsonic acid XXIV. (m) 1,425,929; 1,425,930. 2-Thio XV. 893,499. Acetothienone: XXIV. (m) 1,350,408. Acetyl, Brom diethyl, isocyanate: MXIV. (m) 1,424,236. Acetyl chloride: VII. 647,263. XXII. 910,648; 1,359,071. XXIV. (m) 1,350,408; 1,399,144; (p) 1,434,429. Chlor XXIV. (m) 619,549; 625,159. Trimethyl XXIV. (m) 1,338,297. Acid: anhydrides, Organic XXII. 1,326,040. chlorides, Organic XXII. 1,326,040. Acridin: Amino tolu naphth I. 643,569. Diamino XXII. 1,410,494. 3.6-Diamino N-methyl ‘ I. 1,427,431; 15427,432- XXIV. (m) 1,408,974. 2-7-Dimethyl, dimethyl 3-amino, 6-amino I. 1,473,660. |. . Tetramethyl 2.7-diamino, disulfate 1,418,852. Aerylie acid, 2-Nitro phenyl oxy: VII. 227,470; 228,300; 233,459. Adipie acid: LE. 9383565: 497 Aleohol: Lit, 25,300: XXII. 1,302,011; 1,311,824; 1,315,619; sesego) 1,425,625; 1,427,215; 1,437,483. XXIV. One ahs Aldehyde: ITT) -45204,6390. Alizarin: III. 186,032; 188,061; 258,530; 446,893; 503,295; 772,857; 826,509. XXII. 275,128. XXIV. (m) 966,820. 4-Amino III. 569,405. Eek II. 569,404 Blue III. 399,479; 399,480; 399,481; 401,633; 527,457; 790,079. Bordeaux III. 476,418; 476,419; 476,420; 476,491; 502,265; 608,238. Green IIT. 399,482; 401,635. 2-Nitro III. 790,079. pentacyanin III. 603,659. Alkylation: XXII. 1,426,380; 1,429,714; 1,431,470; 1,433,925. Alloxan: Anilin XXIV. (m) 676,859. Dimethyl XXIV. (m) 667,388. Allyl: alcohol XXIV. (m) 1,360,994. bromide XXIV. (m) 1,336,952; 1,415,700. 1-Amino 5-Naphthol: VI. 729,601. 1-Amino 5-or 8-Naphthol: VI. 1,029,639. 1-Amino 7-Naphthol: VI. 727,963; 874,968; 1,411,245. t-Amino 8-Naphthol: VIL 535)381; 524,665. OV Olt, Ola. 2-Amino 6-Naphthol: VI. 727,967. 2-Amino 7-Naphthol: VI. 656,619; 924,231. 2-Amino 8-Naphthol: III. 644,333; 687,171. 1-Amino 2-Naphthol, ethyl ether: WViIs) 11-550;656. 1-Amino 7-Naphthol, Acetyl: VI. 1,078,925. 1-Amino 8-Naphthol: Acetyl 3.6-disulfo VI. 1,034,898; 1,114,771. Acetyl, 4.6-disulfo VI. 916,323; 1,127,261- Acetyl, 4-sulfo Its 4085207- 2-Amino 5 Naphthol: Acetyl, 7-sulfo VI. 666,867; 941,088; 1,005,233. 4’-Amino 1/2/-azimino phenyl, 7-sulfo Vii or6,161- 583,635; 585,104; 591,616; 608,999; 611,597; 611,664; 618,963; 620,368; 620,369; 627,679; 627,783; 628,233; 498 DIGEST OF PATENTS 3’-Amino benzoyl, 1.7-disulfo VI. 889,016. 1-Amino 8-Naphthol, 3/-Amino benzoyl, 4-sulfo: Vii a51 83,835. 2-Amino 5-Naphthol: 3’-Amino benzoyl, 7-sulfo VI. 724,078; 1,185,413; 1,265,031; 1,282,354; 1,292,385; 1,342,134; 1,362,936; 1,365,706. 4’-Amino benzoyl, 7-sulfo VI. 888,837; 1,015,375; 1,022,287; 1,022,288; 1,032,797; 1,041,146; 1,065,950; 1,101,739; 1,150,675. 3”-Amino benzoyl 3/-amino benzoyl, 7-sulfo VI. 993,073. 2-Amino 8-Naphthol: 4'-Amino benzoyl, 6-sulfo: VI. 1,065,950. 4’-Anisidyl, 6-sulfo VI. 982,954. 2-Amino 3-Naphthol, Benzoyl: VI. 1,145,072. 6-Amino 1-Naphthol, Benzoyl 5.5’-dioxy 2.2/-dinaphthyl urea: VII. 1,144,577. 1-Amino 8-Naphthol: Benzoyl, 4.6-disulfo VI. 1,073,902; 1,073,903; 1,073,904; 1,073,905. Benzoyl, 4-sulfo 524,220. 2-Amino 5-Naphthol, Benzoyl, 7-sulfo: VI. 679,974; 931,423; 931,424; 1,027,148. 1-Amino 2-Naphthol, Brom, 4-sulfo: VI. 1,014,039. 1-Amino 7-Naphthol, 2/-Chlor benzoyl: VI. 1,188,545. 1-Amino 2-Naphthol, Chlor, 4-sulfo: MIT. 4,026;5257. Amino 5-Naphthol: 1.2-Di-, 7-sulfo VI. Serianee 813,155; 873,798; 886,9 sig” ane een 1.2-di-, 7-sulfo VI. 8395155, 2-Amino 8-Naphthol, Dialkyl, 6-sulfo: VI. 567,413. 1-Amino 8-Naphthol, 2’.4’-Dichlor benzoyl, 4.6-disulfo: VI. - 1,073,951. Amino Naphthol disulfo: VI. 501,500. 1-Amino 2-Naphthol 3.6-disulfo: VI. 521,985; 778,476. XII. 808,919. 1-Amino 2-Naphthol 4.6-disulfo: XII. 808,919. 1-Amino 8-Naphthol: 2.4-disulfo VI. 539,609; 560,449; 603,645; 683,119; 999,558; 1,426,190. XV. 614,538; 673,388. 3.5-disulfo, ‘*B” VI. 606,436; 606,438; 3.6-disulfo, “HH” VI. 462,415; 464,135; 468,040; 480,326; 482,106; 496,392; 498,759; 498,873; 498,874; 499,198; 509,625; 512,493; 514,599; 514,931; 516,203; 521,986; 533,508; 541,750; 542,073; 544,699; 544,700; 55794353 557,436; 557438; 557439; 558,613; 561,694; 561,709; 563,384; 563,386; 576,511; 57957733 583,634; 606,439. 639,040; 646,711; 652,456; 655,013; 666,866; 670,398; 684,065; 688,478; 717,550; 728,477; 792,033; 792,034; 843,808; 877,644; 932,813; 950,404; 950,405; 964,786; 987,417; 988,000; 1,014,982; 1,014,983; 1,023,120; 1,028,306; 1,052,262; 1,126,489; 1,199,233; Aa 1,259,499; 1,263,030; 383,711. 4.6-disulfo, Kh VI. 563,383; 563,385; 563,386; 06,181; 606,204; 611,597; 613,638; 613,639; 613,640; 613,641; 613,642; 613,645; 936,456; 969,450; 1,006,051; 1,128,814. XXIV. (m) 1,308,071. 1-Amino 8-Naphthol 4 or 5.7-disulfo: VI. 671,896. 2-Amino 1-Naphthol: 3.6-disulfo 4.8-disulfo XII. 808,919. 2-Amino s5-Naphthol 1.7-disulfo: VI. 532,479; 759,613; 763,761; 897,529; 933,448. 2-Amino 8-Naphthol 3.6-disulfo: VI. 516,604; 556,164; 556,298; 560,448; 578,432; 601,033; 601,859; 608,024; 1,076,756. 1-Amino 8-Naphthol: Ditolyl sulf-,3.6-disulfo VI. 640,989. Ethyl, 3.6-disulfo 7975732. 1-Amino 7-Naphthol, Methyl: VI. 874,067. 1-Amino 2-Naphthol, Phenyl: XXII. 1,460,774. 2-Amino 5-Naphthol: Phenyl amino acetyl, 7-sulfo VI. 1,092,842. Phenyl, 7-sulfo VI. 682,510; 843,137; 843,149; 843,736; 860,220; 860,221; 877,643; 933.447; 933,562; 935,031; 963,739; 1,009,741; 1,020,756; 1,049,109; 1,079,415. 2-Amino 8-Naphthol, Phenyl, 6-sulfo: VI. 953,033; 953,034; 982,952; 982,953; 993,020; 995,161; 1,045,196; 1,076,321; 1,077,492. 2-Amino s5-Naphthol, 4’-Sulfamino benzoyl, 7-sulfo: VI. 1,098,388. 1-Amino 8-Naphthol, sulfurus acid ester: VI. 897,529; 898,217; 912,356. Amino Naphthol sulfo: VI. 442,369, 560,448. 1-Amino 2-Naphthol 4-sulfo: VI. 790,363; 790,364; 805,198; 806,415; 807,422; 835,539; 839,489; 958,912; 1,014,114; 1,023,199; 1,233,433; 1,237,183; 1,402,350; 1,437,758. XII. 808,919. 1- Amino 2-Naphthol Gentian VI. 1,160,344. XII. 808,919. 1-Amino 2-Naphthol 6-sulfo, ethyl ether: VI. 1,150,675. INTERMEDIATE INDEX 1-Amino 2-Naphthol 7-sulfo: XII. 808,910. 1-Amino 5-Naphthol 7-sulfo: VI. 558,344; 654,064; 1,101,739. 1-Amino 6-Naphthol 3-sulfo: VI. 1,009,797; 1,052,135. 1-Amino 7-Naphthol 4-sulfo: VI. 727,966; 899,171. 1-Amino 8-Naphthol: 509,929; 54357475 509,088; 610,349; 683,120; 932,812; 1,009,745; 524,220; 543,748; 593,790; 638,127; 692,675; 958,830; 1,188,4213 1,363,886; 1,372,439; 1,415,704. 4-sulfo VI. 506,284; 533,508; 578,432; 603,008; 644,334; 88,036; 974,346; 5-sulfo VI. 615,497; 5 or 4-sulfo VI. 682,510. 958,774. 2-Amino 1-Naphthol;: 4-sulfo XII. 808,919. 5-sulfo XII. 808,919. 2-Amino 3-Naphthol 7-sulfo: VI. 2-Amino 5-Naphthol: sulfo VI. 1-sulfo VI. 7-sulfo VI. 521,095; 59353473 662,122; 678,323; 724,893; 740,768; 832,393; 859,930; 808,217; 982,507; 1,012,619; 1,210,751. 1,026,902. 521,096; 624,256; 663,498; 697,765; 724,894; 763,761; 839,360; 877,644; 941,088; 1,088,735; 1,338,414. 55553593 658,897; 673,079; 709,186; 740,767; 767,070; 839,382; 888,837; 969,450; 1,006,929; 1,009,796; 1,014,633; 1,024,308; 4Amino Naphthol sulfo: VI. 512,167. 2-Amino 8-Naphthol: eet 6-sulfo - 1,043,873. 3-Xylyl 6-sulfo 499 1,024,794; 1,079,415; 1,126,656; 1,160,406; 1,263,030; XIV. 951,047. 1,032,797; 1,092,842; 1,150,825; 1,213,075; 1,319,852; 2-Amino 8-Naphthol: 6-sulfo, ‘*G”’ 1,074,429; 1,113,468; 1,159,3753 1,216,760; 1,378,388. VI. 454,648; 501,500; 526,763; 536,431; 536,880; 557.4393 571,933; 595,021; 602,855; 613,641; 620,574; 639,041; 644,462; 654,167; 672,714; 683,190; 842,048; 945,780; Q71I,112; 491,410; 525,245; 533,463; 536,878; 556,164; 560,448; 575,904; 599,532; 606,204; 613,646; 622,961; 644,291; 647,237; 666,866; 676,494; 748,076; 858,444; 963,7393 982,508; 501,160; 525,626; 535,036; 536,879; 5574373 560,449; 578,580; 601,033; (ob segs Oe Ge 619,503 629,748; 644,292; 654,065; 671,543; 679,221; 832,393; 921,239; 971,111; 989,000; VI. 982,955. Amins: Aromatic III. 659,565; 666,594; 666,702; 669,894; 675,572; 687,657; 688,576; 723,125; 734,325; 734,866; 748,375; 749,913; 812,599; 996,487. ie 211,180. , » 350,230; 455,952; 951,046. XXII. 1,394,851. Rai aay Carboxylic XIV. 350,230. Heterocyclic XIV. 951,048. Nitroso-secondary 420,311. Nitroso-tertiary XM. 420,311. Sulfo XIV. 350,230. Amyl alcohol: XXIV. (m) 1,352,082. Anilid: Amino stearic acid 902,021. 4-Amino stearic acid VII. 879,424. 2-Nitro benzyl form- (See Benzyl manilid, 2-Nitro) bis=3’-Oxy XXII. 1,315,127. Stearic acid VI. 879,424. Anilin: II. 38,589 Re. 4,746; Re. 4,747; 79,942 Re. 3,103; 96,242; 111,654 Re. 7,429; Re. 7,430; Re. 7,431; Re. 7,432; 138,155; 189,538; 193,158; 387,007; 7 bese eM i III. 599,425; 623,638; 631,605; 631,606; 631,613; 632,621; 647,370; 659,565; 659,566; 668,445; 669,894; 688,576; 748,375; 754,264; 793,558; 809,894; 996,487; 1,015,329; 1,238,932; 1,280,648; 1,394,851. 2Prr.O7 rs 22t, TTA so22r. Lies VI. for- 22. Ul 7 2elolios 221,120; 247,601; 251,162; 253,598; 310,155; 333,039; 409,384; 421,640; 480,326; 485,283; 498,405; 516,756; 524,251; 524,665; 562,200; 563,383; 606,438; 613,638; 613,643; 619,194; 640,989; 656,621; 663,498; 673,079; 717,550; 722,860; 806,077; 843,808; 902,021; 902,186; 993,073; 999,230; 1,026,902; 221,119; 242,707; 269,359; 333,041; 431,297; 498,404; 516,757; 5571440; 59353473 613,639; 622,961; 662,122; 688,478; 724,078; 888,837; 944,328; 1,000,606; 1,024,080; 1,082,581; 1,154,826; 1,201,544; 1,365,040; 1,416,621; XIV. 951,047. 6 or 7 sulfo VI. 1,099,676. 1,009,741; 1,024,081; 1,123,430; 1,173,077; 1,270,290; 1,371,979; 1,429,781. 1,014,984; 1,056,493; 1,126,466; 1,199,2343 1,359,969; 1,408,405; 1,028,239; 1,042,198; 1,078,503; 1,126,489; 1,206,232; 1,286,411; 1,447,485. 620,562; 622,139; 647,279; 712,190; 776,884; 818,341; 841,456; 868,294; 868,755; 894,149; 894,579; 1,243,170; 1,442,743; 1,467,598. 666,627. 613,911; 951,047. VII. IX. XIV. 500 DIGEST OF PATENTS XV. 629,221; 630,952; 641,587; Apel TSS 785,075. : 796,443; 1,128,368; 1,329,808. XVIII. 32,065; 50,3353; 53,241; 248,154; 252,202; 283,766; 310,128; 471,638; 707,813; 1,042,493; 1,065,405. XIX. 516,580; 551,885; 646,794. XXII. 1,303,624; 1,422,494; 1,460,774. XXIII. (Ab) 1,277,056; 1,350,600. XXIV. (e) 1,401,631; (m) 615,829; 709,321; 741,585; 1,197,462; 1,405,228; (pl) 1,422,506; 1,477,805. Alkyl XXII. 1,413,494. 4-Amino 3-chlor dimethyl VI. 891,931. 3-Amino dimethyl I. 1,255,739; 1,255,740; 1,455,486; . 1,455,487. 4-Amino dimethyl PES r, 105; 501. 3-3/-Azoxy di- VIP 763,701 5 91,305,700. Benzyl ethyl, sulfo XVIII. 866,359. Benzyl methyl XV. 1,449,681. XVIII. 611,628; 684,367. Benzyl methyl, sulfo XVIII. 464,538. Benzyl sulfo I. 726,688. VI. 655,013; 906,422; 982,954; 987,417; 1,014,982; 1,051,565; 1,076,819. VII. 916,030. XII. 982,050; 988,870. 1,073,951. HIIs *1,002)066; 1,025,147. VI. 752,562; 789,096; 959,078; 987,417; 1,014,982; 1,014,983; 1,028,306. 2-Chlor, 5-carbo VI. 942,916. 2-Chlor methyl XV. 841,877. 3-Chlor 4-nitroso dimethyl VI. 891,931. 4-Chlor, 3-sulfo VI. 984,900. VI. 297,852. XVIII. 297,415; 297,416; 498,471. 2.5-Dichlor VI. 627,679; 652,456; 879,053; 932,813; 950,405; 1,003,295; 1,457,114. 3.4-Dichlor VI. 787,768; 830,312; 1,010,930. 2.5-Dichlor, 4- ‘sulfo VI. 949,633; 1,150,675. 3.4-Dichlor, 5-sulfo VI. 787,767. 3.4-Dichlor, 6-sulfo VI. 830,312; 849,739. 4. pret 2-sulfo I 1,270,290. Diethyl VI. 297,852; 313,118. XVIII. 290,893; 325,827; 329,637; 412,613; 412,614; 412,615; 1,478,015. Dimethyl VI. 297,852. XXIV. (m) 922,995. XVIII. 222,257; 263,420; 290,856; 290,891; 290,892; 310,128; 325,828; 329,030; 464,538; 519,971; 564,801; 709,160; 2-Anisidin: ES 4-Anisidin 3-sulfo: : 1,402,195; 1,470,554; 1,470,555. peeulre I. 974,346. Ethyl « 4205s res VILs (657665, XV. 1,140,745. Ethyl benzyl XVIII. 623,346; 668,580. Ethyl benzyl, disulfo XVIII. 501,069. Ethyl benzyl, sulfo 380,008. Vi eat, 253.0754 XIX. 641,184. Methyl, w-sulfo VI. 1,027,148. 2-Nitro benzyl XXIV. (m) 428,286. Nitro benzyl, sulfo XXII. 648,261. Nitroso diethyl 6044,402. XIX. 499,927. Dioxy di-, sulfide XXIV. (m) 1,422,869. iodide TIT. — 7,128,836. XVIII. 204,798. XXIV. (m) 464,861. Ethylene; chlorhydrin XXIV. (m) 1,358,750; 1,358,751. diamin diacetacetic ester. XXII. 361,690. Dichlor VII. 943,560. XXII. 1,430,324. Dichlor ethoxy VII. 804,149. XXII. 804,148. oxid III. 1,014,204. XXIV. (m) 1,418,900. ‘Trichlor VII. 943,561; 1,467,598. Trihalogen VII. 910,839. DIGEST OF PATENTS Ethylidene diacetate: XXII. 1,440,918. Flavopurpurin, Amino: III. 450,037. Fluorane, Dichlor dimethyl: XXII. 785,003. Fluorene: XXII. 1,374,605. Fluorenone, 3.6-Dibrom: Ii 91,216,027. Fluorescein: chloride XIX. Dibrom 493,241; 615,791. 617,627. 649,716. Formaldehyde: III. 658,513; 658,514; 704,798; 738,614; 765,576; 785,121; 785,122; 785,123; 790,079; 791,869; 868,399; 871,507. VI. 515,897; 516,468; 516,756; 516,757; 516,758; 516,759; 516,760; 519,522; 519,523; 541,859; 542,073; 1,122,564; 1,338,506; 1,362,936. VII. 662,754; 662,755. IX. 763,756; 932,266; 955,080. XV. 722,630; 801,598; 960,652; T,1O5,S3.0¢ ; 464,538; 538,215. 445,684; 613,113; 625,536; 643,371. 666,579; 704,490; 715,748; 875,415; 891,753; 910,648; 1,437,483. (f£) 1,345,649; (m) 598,914; 601,072; 811,884; 854,452; 1,056,881; 1,299,214; 1,426,348; (p) 1,297,685; (pl) 1,088,677; 1,088,678; 1,306,681; 1,310,087; 1,310,088; 1,345,694; 1,355,834; 1,368,867; 1,369,352; 1,374,526; 1,397;1443 1,414,139; 1,429,265; (t) 1,336,759; 1,344,950; 1,344,951; 1,344,952; 1,375,976; 1,399,510; 1,421,701. Para XIX. 1,403,888. XXIV. (pl) 1,429,267. hydrosulfite XXII. 769,593; 804,157; 812,124; 814,031; 814,032. sulfoxylate Ill. 1,204,639. XXII. 793,559; 841,999; 871,600; 885,566; 885,567; 887,050; . 935,815; 1,006,793. XXIV. (m) 1,053,300. Formalin: (See Formaldehyde.) Formanilid, 3-Amino: VI. 1,087,480. Formaurin, Dimethyl dicarbo, leuco prod- uct: XVIII. 976,417. Formie acid: III. 1,045,805. VI. 1,020,756. XXL. 14457062 XXIV. (m) 428,286. Chlor, ethyl ester XXIV. (m) 1,375,949. Fuchsin: XVIII. 250,207. Furfural: XXII. 1,322,054; 1,357,467. XXIV. (pl) 1,398,146; 1,441,598. Fustie: VI. 409,384. Gallamie acid: XIX. 551,885. Gallamid: XVII. 898,842. INTERMEDIATE INDEX Gallie acid: ITI. 348,613; 617,981; 623,069. Gamma acid: (See 1-Naphthol, 7-Amino, 3-sulfo.) Glycerin (Glycerol):, III. 786,085; 787,859; 790,079; 793,558; 898,104; 809,892; 809,893; 809,894; 811,471; 818,336; 818,992; 820,379. VII. 661,871, 894,006. XV. 636,066; 645,738; 728,623; 763,193; 880,936. XXIV. on 295,825; 466,708; 741,585; 1,424,137. Glycocol: 2 ene! VII. 669,794; 680,395. Ph Vene (ii) 16a T7107. Ethyl phenyl VII. 617,651. Ethyl 2-tolyl Glycol: acetate XXII. 1,430,324. chlorhydrin or bromhydrin XIV. (m) 1,308,414. Dimeth XXIV. (£) 1,418,904. Dithio XXIV. (m) 1,422,869. Trimethylene XXIV. (m) 1,286,944. Glyecolie acid: anilid 2-carbo VII. 768,455. 2-Chlor phenyl thio VII. 916,030. 4-Chlor phenyl thio VII. : 899,152. Chlor tolyl thio VII. 902,029. Di-, guaiacol ester XXIV. (m) 948,084. 6-Methoxy 4-chlor 3-methyl thio Wilewet.6025,135- Naphthalene 2.6-dithio VII. 1,444,277. 2-Nitro phenyl thio 959,617. VII. 848,354. Thio 2-carbo VII. 867,679. 2.4-Xylyl thio VII. 881,624. Glycollid: VII. 768,455. Glyoxylie acid: III. 1,079,568. 4-Amino phenyl XXII. 676,860. Methyl 4-amino phenyl XXII. 708,511. Guaiacol: XXIV. ester XXIV. Guanidin: XXII. 1,417,369. 5.5’-Dioxy 7.7/-disulfo 2.2'-dinaphthyl V. 677,517. : 5.5/5’'-Trioxy 7.7/7”-trisulfo, naphthyl Nia 67735 10. Gun eotton: (See Cellulose, Nitro.) (£) 1,345,649; 1,418,904. (m) 624,772. 2.2'2”-tri- H. aeid: (See 8-Amino 1-Naphthol 3.6- disulfo.) Halogenation: XXII. 721,961; 1,308,763; 1,345,373; 1,384,909; 1,420,346. Heliotropin: XXIV. (f) 804,682. 913 Hematoxylone, a-Anhydro tetra methyl: VE 17106,7515 Hexamethylenetetramin: XXII. 852,993; 860,636. XXIV. (m) 567,068; 607,172; 690,804; 852,993; 869,636; 1,076,160; (pl) 1,306,681; 1,375,959; 1,435,801. Hydantoin, aq-Phenyl: VII. 714,000. Hydrazin: Alphyl XXIV. (m) 1,425,929. Aromatic XII. 324,630. XIV. 386,709. 6-Biom 4-sulfo 2-tolyl XII. 1,109,919. 2-Chlor aryl, sulfo XII. 1,098,600. 2-Chlor phenyl, 3 or 5 sulfo XII. 982,050; 1,098,600. 3-Chlor 2-tolyl, 5-sulfo I. 935,370. hydrate Liter 285;727 Nitro phenyl XII. 627,690. 4-Nitro phenyl XII. 627,690; 988,870. 2-Oxy s5-sulfo 3-carbo phenyl N/T 2705325. Phenyl XVIII. 580,766; 609,598; 621,393. Phenyl, sulfo xX Tia 24,630: XIV. 386,709. Phenyl, 2 and 4 sulfo XII. 969,428; 972,951. sulfo XIV. 386,700. 2-Tolyl XVIII. 664,450. 4-Tolyl XXIV. (m) 503,066. Hydroquinone: XV. 594,106; 594,107. XOX Wie (pts 207,005- Acetyl 2.5-diamino . View 7395215. : 4'.4”-Diamino, diphenyl diether VI. 839,360. Hydroxylamin: III. 1,216,134; 1,464,079. VI. 447,189 VII. 647,279 disulfo SOT Pare Ol st 777. Hydroxylation: XXII. 1,062,351; 1,297,7925 1,320,454; 1,321,271; 1,430,184. Tehthyol sulfo acid: XXIV. 318,662; 495.124; ©71,135; 709,321. Immedial Black V: XVS> Ga5.7172 Indanthrene: III. 753,659; 785,121; 844,914; 893,837. Blue III. 948,204; 970,378. 4.4’-Diamino 3.3’/-dibrom III. 785,123. Dianthraquinonyl III. 1,0523480. 3.3/-Dimethyl Tib922,567- Indene: XKIVS. Clee 263.8136 1,294,836; 1,360,665. 1.3-Diketo hydro VI. 1,075,305. 514 _ DIGEST OF PATENTS Indigo: VII. 251,501; 720,217; 765,687; 765,996; 856,776; 872,115; 872,280; 883,703; 888,230; 899,863; 920,156; 937,040; 937,:041; 997,766; 1,012,363; 1,043,682; 1,061,781; 1,070,541; 1,074,850; 1,473,887. Dehydro VII. 1,012,363; 1,042,679. XXIII. (In) 1,448,251. 4.4’-Diamino VII. 940,586. Dibrom VII. 916,031; 918,920; 1,043,468. 5.5’-Dibrom VII. 1,414,335. 6.6’-Diethoxy, thio VII. 963,813. 5.5’-Dimethyl VII. pararaae b-Naphthy VII. 932,334. hio VII. 867,715; 898,738; 947,030; 954,273; 955,659; 959,617. Trichlor VII. 915,338. white VII. 706,921; 812,598. Indirubin: VII. 876,158. Indogen: VII. 250,035. Indogenie acid: VII. 250,036; 259,260; 259,261. Indole: XII. 698,328. Dihydro methyl vps 913,513. VI. 719,048; 719,049; 791,525; 791,526; 1,114,750. 2-Methyl, sulfo VI. 978,439. 2-Methyl, 6-sulfo AYA Ns oe th ge Poh Indophenol: XV. 665,547; 696,751; 708,662; 736,403; 741,030; 778,478; 1,209,580; 1,302,671; 1,471,854. Benzyl methyl XV. 1,449,681. 2.6-Dichlor _ XV. 779,860. XV. 763,320. DEV. ag h2o;97 1. XXII. 1,128,370. thio. sulfo 679,199. 625,268; 646,841; 713,437; 715,074; 737836; 778,725; 876,158; 894,579; 898,452; 904,867; 960,098. 6-Amino thio VII. 1,081,898. Indoxyl : VII. II. 1,074,405. 4-Chlor 5-brom VII. 957,683. Diacetyl VII. 626,231; 657,359; 699,581. Dibrom, thio VII. 1,108,057. 4.5-Dichlor, carbo, ester VII. 955, 410. Dimethyl 4’-amino a-anilino, thio VII. 997,260. 7-Methyl VII. 1,028,911. 6-Nitro diacetyl VII. 1,266,092. VII. 819,348; 836,309; 848,356; 850,827; 867,714; 875,649; 954,273; 997,260. Indoxylie acid: VII. 690,332; 778,725. Isatin: III. 908,156. VII. 240,941; 240,942; 259,629; 310,604; 625,268; 841,003; 848,355; 867,714; 874,649; ph Ee 943,678; 394; 968,697; 1,028,911. XXIV. coy 1,181,485; 1 aoa 1,350,408. Acetyl VII. 923,959. a-anilid VII. 647,279; 647,280; 697,545; 848,356; 850,444; 954,273; _. 99954393 1,025,174; 1,144,577. chloride VII. 1,122,790. 5-Chlor, 4 "chlor a-anilid VIL. “1, x08,086575,1575455- Dibrom VII. 898,452; 958,464; 958,465; 961,397; 961,399; 998,596; 1,001,919. 5.7-Dibrom VII. 1,051,856. VII. 980,140. 5-7-Dichlor VII. 1,074,405; 1,266,092. XVIII. 1,434,983; 1,466, 687. 5.6-Dichlor, a-anili rie ' 1,147,778. VII. 961,398. s-Methyl 4-toluidin VII. 310,604. Isatinie acid: VII. 625,268. Isoprene: XXIV. (pl) 1,294,662. Isopropyl alcohol. (See Propyl alc., Iso) Isovaleryl bromide: XXIV. (m) 998,726. Juglon: ILI. =1;327,206. Ketol, Methyl: VI. 1,024,081. Ketone: VII. 726,688. XXII. 1,450,569. Ketoxin: VI. 447,189. Lactie acid, 2-Nitro phenyl chlor: VII. 233,459. Lacto Ketone: 2-Nitro phenyl VII. 540,427. 2-Nitro phenyl methyl VII. 772,560. Limonene: XXIV. (pl) 1,323,589. Maleie acid: XXII. 1,401,937. Malonie acid: ester XXIV. . (mm) 3,400.7 127 Anilin, diethyl ester VII. 620,563. Brom or chlor VII. 621,662. N-Dibutyl, ester XXIV. (m) 1,331,712. Diethyl XXIV. (m) 773,251. INTERMEDIATE INDEX 515 Menthol: XXIV. (m) 830,043. Mesidin: XIX. 493,241. Metanilie acid? VI. 380,403; 516,381; 807,289; 833,605; 901,675; 982,955; 997,061; 1,093,829; 1,319,852; 8,123;8297 Thio VII. 1,461,435. 7-trimethyl ammonium chloride VI. 610,367. trisulfo VI. 268,505; 268,506; 268,507. 1-Naphthol 3.6.8-trisulfo: VI. 584,081. XVIII. 891,889. Naphthol trisulfo monoamid: VI. 458,284. Naphthol Yellow S: VI. 844,814. Naphthone: a-Aceto XXIV. (m) 1,197,462. a-Oxy thio VII. 804,005. Naphthoquinone: TIT. 368,054. 1.2-Naphthoquinone: III. 653,492. 1.4-Naphthoquinone: III. 1,105,004; 1,396,483. 2-3-Dichlor III. 1,419,502. 7.8-Phen carbazole XIV. 1,261,858. 1.2-Naphthoquinone 4-sulfo: wV. GI254706; 1.4-Naphthoquinone 4’-sulfo phenyl: XV. 912,176. Naphthohydroquinone: VI. 420,372; 420,374. 1.2-Naphthoxazole, 4/-Amino 5-oxy, 7-sulfo: I. 1,082,596. Naphthyl 1-aldehyde: XXIV. (m) 1,197,462. 1.2-Naphthyl 4’-Amino phenyl 3.8 disulfo, triazole: VI. 820,052. 2-Naphthyl glycin: VI.. 498,803. Naphthyl, N-Methyl, peri-imid: III. 1,200,848. 2-Naphthyl = sym-5-Oxy thio urea: VI. 697,765. Naphthyl: phenylamin VI. 211,671. sulfate VI. 256,401. phenyl g-sulfo, phenyl apt shin INTERMEDIATE INDEX 1.2-Naphthyl 4/-Sulfo triazole: VI. 670,398. Naphthylamin: II. 134,076. VI. 204,799; Re. 9,144; 221,116; 221,119; 242,707; 251,164; 260,242; 261,175; 261,766; er hy 2851335; 289,613; 396,293; 844,845. XXII. 1,449,423. 1-Naphthylamin: ELE t. 018,43 35 -VI. 204,799; Re. 9,144; 256,376; 297,852; 332,528; 345,901; 365,666; 365,667; 380,402; 380,928; 402,980; 412,440; 423,569; 425,585; 438,438; 440,639; 449,629; 462,415; . 462,824; 464,566; 464,775; 466,202; 473,928; 476,336; 476,393; 479,515; 482,106; 491,410; 500,118; 502,912; 503,148; 512,167; 515,339; 515,381; 533403; 543,747; 543,748; 548,416; 560,796; §82,959; 590,088; 593,790; 601,033; 602,641; 603,093; 605,103; 608,999; 610,349; 613,638; 613,640; 613,644; 613,920; 618,963; 628,025; 629,748; 634,824; 644,234; 644,237; 644,238; 644,239; 644,240; 654,107; 654,168; 655,529; 671,896; 683,120; 877,643; 899,171; 903,284; phenyl 1,014,539; 1,033,310; 1,073,905; 1,113,468; 1,180,985; 1,183,831; 1,193,829; 1,265,031; 1,310,532; 1,319,852; 1,416,621; 1,452,083. XIV. 051,046; 951,047; 951,049. XV. 741,030; 796,443; 1,099,039; 1,251,369. XVIII. 297,413; 688,967. XXII. 1,442,818; 1,451,666. 2-Naphthylamin: III. 1,011,068; 1,016,638; 1,162,496. VI. 320,633; 333.2573 365,666; 365,667; 380,402; 381,045; 381,046; 395,474; 497,032; 558,612; 606,436; 1,024,794; 1,217,042; 1,362,936. X. 1,455,488. XIV. 350,230. 1-Naphthylamin, Acetyl 4-amino, 6 or 7- sulfo: VI. 1,422,866. 2-Naphthylamin, 4/-Amino 2’-sulfo phenyl: VI. 628,025. 1-Naphthylamin : Benzyl XVIII. 406,435. Benzyl, 8-sulfo VI. 722,860. 2-Naphthylamin, 1-Chlor, 5-sulfo: VI. 710,059. 1-Naphthylamin: 2-diazo oxid 4-sulfo VI. 1,028,006. 2.4-Dichlor, 7-sulfo VI. 765,581. Naphthylamin: disulfo VI. 345,901. 3.6-disulfo VI. 412,440. 1-Naphthylamin: disulfo VI. 502,912; 888,852. 2.4-disulfo VI. 770,177; 933:447- 3.6-disulfo : VI. 546,068; 546,069; 935,018. 4.7-disulfo 3.6-dioxy .; 519 VI. 376,392; 420,374; 449,629. 4.8-disulfo : Viv srr, 532: 2-Naphthylamin: disulfo VI. 454,648. 1.5-disulfo VI. 718,356. 3.6-disulfo VI. 454,840; 468,539; 594,123; 631,611; 740,768; 842,048; 959,078; 1,051,859; 1,052,031; 1,067,881. 4.8-disulfo VI. 931,424; 976,4013 1,180,985; 1,183,831. XIV. 951,046; 1-Naphthylamin: 4-Ethoxy phenyl XVIII. 658,504. Ethyl oe 1,113,766; 1,199,697. XVIII. 517,473. 2-Naphthylamin Ethyl -sulfo VI. Ethyl, 5 V 451,132. 1-Naphthylamin, Methyl pheny]: XVIII. 308,748; 684,457. 2-Naphthylamin, Methyl phenyl: XVIII. 603,016. 1-Naphthylamin, Methyl, sulfo: VI. 381,471. 2-Naphthylamin: 1-Methyl, sulfo VI. 696,811. Methyl, 7-sulfo . 1,009,740. Naphthylamin, Nitro: Vis e2LI 525s 1-Naphthylamin: 4-Nitro XXII. 675,434. 4-Nitro, 6- or 7-sulfo VI. 1,371,979. : Naphthylamin, Nitroso dimethyl: Nou A 2O.S TT. 1-Naphthylamin: 4-oxy phenyl XV. 1,105,515. 4’-Oxy phenyl 4.8-dinitro XV. 675,585. Naphthylamin, Phenyl: XV. 778,478. 1-Naphthylamin, Phenyl: XVIII. 297,414. 2-Naphthylamin, Phenyl: VI. 1,457,235. 1-Naphthylamin: Phenyl, 5- or 7-sulfo - 887,348. Phenyl, 8-sulfo 498,405; 611,664; 841,371; 951,047. 449,629; 499,216; 921,105. 1,188,421. 2-Naphthylamin, Phenyl, 6-sulfo: VI. 989,001. Naphthylamin sulfo: VI. 261,175; 262,620; 289,613; 447,303. i-Naphthylamin: sulfo 204,799; Re. 9,144; 286,376; 268,506; 358,865; 363,502; 375,848; 380,928; 381,471; 412,149; 421,640; 447,302. XIV. 386,709. a-sulfo IX. 333,036. 2-sulfo VI. 619,194; 1,016,307; 1,113,468. XV. 1,083,489. XVIII. 506,918. 520 DIGEST OF PATENTS XXII. 1,083,489. 4-sulfo (See Naphthionic acid) sa XVIII. 6-sulfo VI. 603,645; 603,646; 603,647; 603,648; 644,238; 676,494; 676,495; 920,151; 999,7973 1,000,269; 1,010,433; 1,024,080; Dertrate 1,032,412; 1,099,676; 1,180,985; 1,270,290; 1,319,852. XIV. 951,047. 6- or 7-sulfo VI. 498,404; 498,405; 536,870; 543,539; 583,439; 602,856; 602,857; 602,858; 603,090; 644,233; 644,235; 644,236; 648,623; 658,697; 679,221; 709,186; 716,342; 722,860; 1,014,884; 1,416,621; 1,422,866. 874,967; 1,054,348. 605,119. XIV. 951,047. 7-sulfo VI. 546,068; 546,069; 546,070; 920,151; 1,038,209; 1,038,210; 1,088,735; 1,125,050; 1,270,290. 8-sulfo VI. 498,404. 2-Naphthylamin: sulfo VI. 204,799; Re. 9,144; 256,378; 257,243; 332,830; 334,257; 342,432; 344,971; 357,274; 401,483; 404,331; 476,336; 690,294. XVIII. 263,420. VI. 650,757; 858,065; 911,186; 1,073,784; 1,383,711. VI. 498,303. XIV. 386,709. VI. 329,634; 1,101,739. VII. 1,108,056. 6-sulfo VI. 332,829; 420,372; 1,092,842; 1,394,823. 7-sulfo VI. 362,813; 363,502; 395,474. VI. 555,658; 908,580; 1,429,782. 1-Naphthylamin: Tetrahydro DOV ceed I Ss 230s 4'-Tolyl VI. 425,885. XVIII. 647,260. 2-Naphthylamin: 3-Tolyl XVIII. 688,966. 4-Tolyl VI. 354,746; 423,550. 1-Naphthylamin, 4’-Tolyl, 8-sulfo: VI. 408,404. Naphthyiamin trisulfo: VI. 458,284. 2-Naphthylamin, 1.5.7-trisulfo: VI. 737.967. Nicotinic acid chloride: XXIV. (m) 1,403,117. 2-Nitranilin: VI. 888,981; 1,188,545. 3-Nitranilin: VI. 341,991; 380,927; 528,965; 889,016; 950,404. XV. 805,637; 896,916; 897,873; 909,277; 1,405,446. XXIV. (pl) 1,441,598. 4-Nitranilin: VI. 211,525; 333,257; 334,257; 376,392; 380,928; 424,019; Oil: 454,648; 480,326; 483,368; 491,410; 514,599; 525,657; 537,532; 536,878; 536,879; 536,880; 557,440; 562,200; 563,384; 588,203; 606,438; 613,639; 613,645; 639,040; 639,041; 647,237; 700,565; 728,388; 728,455; 843,808; 1,006,051; 1,076,756; 1,082,719; 1,235,253; 1,241,153; 1,365,040; 1,415,704. IX. 763,756. XV. 706,969; 1,199,697; 1,251,369; 1,302,671. XXII. 729,876; 1,400,555. 2-Nitranilin: 4-Chlor. VI. 990,173; 1,059,599. IX. 955,080. VI. 914,146; 1,075,305. IX. 932,266. 4-Nitranilin, 2-Chlor: VI. 628,233; 703,105; 865,587; 943,536. 2-Nitranilin: 4.5-Dichlor VI. 921,546. 4-sulfo VI. 692,675, 1,086,155. 3-Nitranilin, 4-sulfo: VI. 993,549. 4-Nitranilin : 2-sulfo VI. 714,882; 724,743; 740,767; 800,914; 832,393; 921,105; 921,239; 944,328; 991,750; 1,008,907; 1,038,209; 1,038,210; 1,088,7353 1,123,430. 3-sulfo VI. 687,171. 2-sulfon, ethyl anilid VI. 1,429,781; 1,429,782. Nitranisol: VI. 357,273. Nitration: XXII. 800,913; 1,297,170; 1,309,320; 1,423,494. Nitrobenzene: III. 893,837. VI. 406,669; 406,670. VII. 841,456; 848,355; 867,715; 887,609; 899,863; 968,697. IX. S1,306;008. XVIII. 310,128; 471,638; 707,813. 2-Nitrobenzene, 1.4-Dichlor: XV. 658,055. Nitrobenzene, 3.4-Dichlor: VI. 787,767. 4-Nitrobenzene sulfo: XV. 718,342. Nitrovenzene 2.4.5-Trichlor: XV. 1,329,898. , Nitrosobenzene: (See Benzene, Nitroso.) Nitrophenetol: 4 VI. 342,432. i Nitrosamin, 4-Amino methyl phenyl: VI. 754,315- Novolak resin: XXIV. (pl) 1,354,154. XXIV. (pl 1,430,034. ¥ Hydrocarbon XXII. 1,477,058; 1,477,7293 1,478,027. Mineral, sulfo XXII. 1,301,662; 1,301,663; 1,303,779; 1,330,624. Pelargonium XXIV. (f) 548,719. Sulfo salt of resin F i INTERMEDIATE INDEX 521 AAI. 722,506; 722,507. Soluble XXII. 628,503; 861,397; 1,301,662; 1,301,663; 1,303,779; 1,330,624; 1,416,284. Turkey Red VI. g11,186. Olefin: XXIV. (pl) 1,430,538. Orchil, Methyl: VI. 412,148; 412,149. Orein (Orcinol): 394,425; 404,331; 410,058; 509,623. Methyl, sulfo VI. 410,057. Oxalie acid: XVIII. 603,300; 609,599. XXII. 1,445,162. XXIV. (m) 837,083; 942,674; 1,028,074. Oxalyl chloride: III. 1,126,475. VII. 1,461,435. Oxamin sulfo, 3-Amino tolyl: VI. 683,190. Oxanthrol: III. 818,992. Oxidation: XXII. 729,502; 757,136; 823,435; 1,308,796; 1,324,715; 1,332,028. Patent Blue, amino leuco: VI. 1,237,192; 1,237,193. Perimidin: VII. 1,222,790. pe Va 01,802,271 % 1,132,022. Methyl XV. 1,209,580. Perylene: XXII. 1,384,615; 1,454,204. Dioxy XXII. 1,454,204; 1,454,205. Petroleum: XXIV. (e) 1,309,577; (m) 318,662; 513,204. Phenacetin: XXIV. (m) 596,797. Phenanthraquinone, 4.5-Dinitro: Vn eT, 007,514. Phenanthrene: III. 1,288,431. XXII. 685,895. quinone JTIl. 644,333. quinone, Dibrom III. 1,095,780. 2-Phenanthrol: Wile 3025270. Phenazin: XV. 701,435. 2-Amino 7-oxy XV. 818,980. Naphsultam VI. 1,431,656. PTY ok, 4 56,502. 4-Phenetidin: MPV. 951,046. XXIV. (f) 489,728; (m) 543,579; 596,797; 602,109; 602,690. Phenetidin, N-Methyl: XXIV. (m) 1,426,348. 4-Phenetidin, 2-Nitro: VI. 569,395. Phenmorpholin: XIX. 949,906. Methyl XX 2O13,514. Phenol: III. 619,114; 831,002; 1,038,589. Vie oin TOs 2Tr, 5255. 211,075; 297,852; 386,192; 426,345; 454,840; 472,121; 501,160; 514,599; 515,897; 519,522; 519,523; 543,539; 585,104; 627,679; 628,233; 644,462; 655,013; 880,293; 1,009,952; 1,014,633; 1,067,881. IX. 1,380,186. [XeENO TS e232 XIV. 350,229; 350,230; 455,952. XV. 646,873; 653,277; 653,278; 679,199; 696,751; 698,555; 706,969; 708,662; 723,154; 740,465; 763,320; 776,264; 779,860; 1,083,110. XVIII. 603,300. XIX. 1,381,503. XXII. 679,199; 776,264; 779,860; 1,301,909; 1,308,757; 1,309,683; 1,312,127; 1,365,407; 1,409,588; she SE e PAas 593: Bes 1,439,128; 1,461,745; 1,466,991. XXIV. (e) 1,292,266; (m) 812,608; 4 942,674; 948,084; 966,820; 1,432,291; (pl) 1,088,677; 1,088,678; 1,310,087; 1,310,088; 1,345,694; 1,369,352; 1,374,526; 1,375:959; 1,398,146; 1,429,265; 1,429,267; 1,435,801; (t) 1,399,510. alphyl derivatives XXII. 252,782. Amino XXII. 618,809. 2-Amino VI. 826,279; 1,282,356. XV. 608,355} 650,326; 934,302. - 402,980. XIX. 675,215; 821,452. VI. 476,335; 548,460; 1,219,954. XIV. 636,065; 951,046. XV. 549,036; 594,107; 601,363; 601,364; 610,541; 628,607; 635,168; 636,066; 645,738; 648,957; 748,755; 650,292; 650,293; 650,326; 650,327; 657,768; 658,055; 660,058; 667,689; 675,585; 688,646; 695,835; 709,151; 731,669; 73557753 741,030; 796,443; 841,877; 843,156; 866,939; 909,155; 1,081,600; 1,083,489; 1,102,171; . 1,113,766; 1,175,230; 1,209,580; 1,265,836; 1,265,837; 1,314,929. XXII. 595,807; 641,100; 648,755; 650,327; 709,151; 1,083,489. 4-Amino, allyl ester XOX EV Gin) 1,394,037. Acetyl 3-amino XIX. 821,452. Acetyl 4-amino VI. 749,193. Acetyl 2.5-diamino 4-chlor VI. 759,284. Acetyl 2.4-diamino, 6-sulfo VI. 803,592; 983,132. Acetyl 3.6-diamino, 4 sulfo, methyl ether VI. 1,408,405. Acetyl ethyl 4-amino SOXTVe a) 5 7.05410- 4’-Amino benzoyl 2-amino 4-chlor VI. 1,114,750. 3-Amino carbo XXII. 427,564. 4-Amino 5-carbo VII. 881,158. 2-Amino 4-chlor VI. 644,238; 826,280; 843,756; 863,290; 958,774; 1,034,898; 1,221,849. XV OSL.07 7. 4-Amino 2-chlor XV. 732,090; 742,189. 522 XXII. 742,180. s-Amino 4-chlor acetyl 2-amino, methyl ether IT. 1,169,344. 2-Amino 4-chlor, 6-carbo I. 1,375,701. wees 2-Amino 4-chlor, ethenyl derivative I. 843,077. | 2-Amino 6-chlor 4-nitro VI. 961,354; 981,276; 1,408,206. 2-Amino 4-chlor, 6 sulfo VI. 672,714; 683,120; 685,647; 726,695; 865,252; 1,003,266; 1,078,925. 6-Amino 2-chlor, 4-sulfo VI. 644,239. 2-Amino dichlor » 302,790; 303,335. 4-Amino dichlor : XV. 1,081,598; 1,081,599. 2-Amino 4.6-dichlor 1,419,501. Amino dinitro XXII. 1,460,708. 4-Amino, ditoluene disulfo ester XXIV. (p) 1,316,804. 2-Amino seleno XXIV. (m) 1,087,157. 2-Amino, 4-sulfamid VI. 1,325,841. 2-Amino, 4-sulfanilid VI. 1,316,781. Amino, sulfo VI. 516,381; 726,963. Amino, sulfo’ III VI. 671,903. Amino, sulfo IV VI. 671,902; 671,904. 2-Amino, sulfo VI. 1,265,031. 2-Amino, 4-sulfo IT. 923,635. VI. 634,824; 722,715; 727,962; 727,965; 727,967; 729,601; 961,355; 964,919; 1,210,908; 1,216,760; 1,216,812; 1,419,500. XV. 644,959. XXIV. (m) 466,708. 2-Amino, q-sulfo, methyl ether VI. 1,453,660. 2-Amino, 6-sulfo VI. 865,252; 865,253. 3-Amino, 6-sulfo VI. 572,723; 946,052; 1,025,983. 4-Amino, 2-sulfo XV. 628,609; 648,754; 650,292. XXII. 648,754. 2-Amino thio XV. 1,452,805. Benzylidene 4-amino XXIV. (p) 922,040. Chlorinated, esters. XXII. 1,023,758. 2-Chlor XV. 776,264. XXII. 776,264. ’ 4-Chlor Vi; 036,327. Chlor amino derivatives (See Phenol, Amino chlor) 6-Chlor 2.4-dinitro XV. 935,009. Chlor nitro V. 701,051. 4-Chlor 2-nitro VI. 683,119. 4-Chlor 2-nitro, 6-sulfo VI. 684,065. 2.4-Diamino VI. 823,793. XV. 618,152. 2.4-Diamino, 6-sulfo VI. 693,670. DIGEST OF PATENTS 2.6-Diamino, 4-sulfo VI. 665,606; 677,231; 680,283; 692,676. 2.6-Dichlor XVIII. 978,800. fs eae thio I 1,044,674; 1,044,675. 3-4-Dichlor thio ie III. 1,044,673. Diethyl 3-amino XVIII. 701,427. XIX. 377,349; 377,350; 402,436; 573:299; 576,222; 576,223; 609,998; 625,641. Dimethyl 3-amino XIX. 425,504; 445,684; 449,520; 578,578; 1,006,738. Dimethyl 4-amino XXIV. (p) 1,434,429. Dinitro XV. 702,369; 904,224; 1,026,881; 1,187,614; 1,279,307. 2.4-Dinitro IX. 1,299,171; 1,349,802; 1,393,714; 1,413,914. XV. 618,152; 647,846; 655,659. Ethyl 3-amino 456,081; 633,883. Ethyl benzyl 3-amino xX 609,998; 624,877. Halogen XXIV. (m) 1,036,087. 2-Halogen XXII. 554,974. 4-Methyl acetyl 2-amino VI. 1,408,363. Methyl 4-amino XXIV. (p) 1,434,429. Methylene amino XXIV. (pl) 1,354,154. 2-Nitro XV. 960,652. XXIV. (m)_ 1,390,972. 4-Nitro 2-amino VI. 644,240; 841,371; 843,137; 879,552; 933,842; 1,159,375; T,213,0755. 2 216,813; 1,242,536; 1,259,499; 1,282,354; 1,202,385; 1,411,245. s-Nitro, 2-amino II. 1,416,646. VI. 827,468; 1,265,030; 1,394,823. 2-Nitro 4-amino, 6-sulfo VI. 644,235. 2-Nitro 6-amino, 4-sulfo VI. 628,814; 644,233; 644,234; 644,237; 671,902; 671,903; 787,046. 3-Nitro 2-amino, 5-sulfo VI. 647,236. 4-Nitro 2-amino, 6-sulfo VI. 644,236; 986,287. 6-Nitro 2-amino, 4-sulfo VI. 654,064; 654,065; 667,035; 677,227; 677,228; 677,229; 677,230; 695,238; 725,848; 727,064; 727,966; 741,552; 798, 808; 1,027,132. 6-Nitro 2-amino, 4-sulfonamid VI. 1,338,414. s-Nitro 4-chlor 2-amino VI. 843,077; 846,511; 933,841. 6-Nitro 4-chlor 2-amino VI. 843,149; 1,011,770. 2-Nitro, 4-sulfo IX. 300,874. XXIV. (m) 466,708. Nitroso XV. 919,572; 1,081,638; 1,083,489; 1,128,371; 1,471,854. XXII. 1,083,489. 4-Nitroso INTERMEDIATE INDEX XV. 653,278; 727,387; 802,049; 829,740; 931,598; 956,348; 966,002; 1,247,475; 1,329,898; 1,465,853. 3-sulfo 1,126,656. 4-sulfo 879,552. IX. 300,874; 1,396,001. XXII. 1,465,680. 4’-Toluidin 3’-sulfonyl 4-chlor, 6-sulfo Vile or 529,234: 3-4.5-Trichlor 2-amino, VI. 1,408,297; 1,431,655. 3-4.6-Trichlor 2-amino VI. 1,426,189; 1,426,190. Phenolphthalein: XXIV. (m) 618,167; 998,726. Diethyl 3-amino XIX. 642,893. Tetra iodo XXIV. (m) 618,168. Tetramethyl 3.3’-diamino XIX. 499,927. Phenosafraninone: XV. 778,713. Phenthiazole: 4-Amino phenyl, carbo 1,125,073. 4’-Amino phenyl, carbo sulfo Ty 4,128,074. Phenyl acetic acid: 259,629. eeetee - 259,629. chloride VII. 1,043,682. Phenyl: 2-Amino 4-chlor, ether T. 950,404. 2-Amino, ether VI. 932,813. 3-Amino 4-oxy, arsenic acid XXIV. (m) 1,120,700. 2-Amino, 2’-tolyl ether VI. 932,812. 3-Amino, trimethyl ammonium chloride VI. 602,641; Re. 11,714. chloroform: XVIII. 1,460,315. cyan acetamid XXIV. (m) 1,285,703. 4.4/-Di- (See 4.4’-Diphenyl and deriva- - tives) sym-Diethyl diamino ditolyl oxy, methane VIII. 472,001. Dimethyl diamino tolyl, methane I. 675,568. dimethyl ammonium chloride XV. 688,999. ethyl oxy acetamid XXIV. (m) 1,375,949. hydrazin fis > 5,001,325. VII. 1,108,056. XXIV. (m) 307,399. _ 4-Methoxy, cinchonic acid XXIV. (m) 1,076,160. Methyl amino, propanol HCl XXIV. (m) 1,356,877. mustard oil VI. 607,765. 2-Nitro, nitro methane VII. 1,015,495. 3-Nitro 4-oxy, arsenic acid XXIV. (m) 1,422,294. sulfonyl chloride VI. 1,067,881. 4’-Sulfo 2,4-diamino, ether VI. 880,292. thio glycocol 2-carbo VII. 868,295. 34 4’-Tolyl 4-amino, sulfid VI) 99 ,076;321- Tolyl 4-amino, sulfoxid 1,077,492. Trioxy, carbinol XVIII. 609,598. Phenyl glycin: DUD 1,23,39070.1,200, 103; VII. 704,804; 714,000; 714,042; 727,270; 731,285; 737,836; 761,440; 756,171; 776,884; 798,077; 818,341; 839,099; 860,900; 894,579; 960,671; 963,377; 984,442; 1,211,413; Re. 14,364. Acetyl VII. 801,708. Acetyl, arsenic acid XXIV. (m) 1,299,215. 3-Amino VI. 858,444; 8593930; 1,056,493. Amino, sulfo VI. 658,506. Arseno XXIV. (m) 1,290,214; 1,315,127. 4-Arseno, bis=(3’-oxy anilid), OUD Ven (nt) 2,305.1 27. 2-carbo VII. 618,096; 647,263; 868,755. 4-Brom 3-chlor, 2-carbo VII. 957,683. 4-Brom 6-chlor, 2-carbo VII. 948,241. 3.4-Dichlor, 2-carbo VII. 955,410. 5-Ethyl thio, 2-carbo Vito 1.001.457. Phenyl glycocol: VII. 524,256; 622,139; 680,395; 778,752. 2-carbo VII. 546,165; 625,268; 690,346; 730,148; 761,007; 778,725. 2-carbo, diethyl ester VII. 651,453. 2.3-dicarbo VII. 540,564. sulfo IIT VIO 671,003: VI. 671,902; 671,904. Thio, 2-carbo VII. 891,690. Phenylene diamin: VI. 384,342; 491,422. 2-Phenylene diamin: XV. 641,935. 3-Phenylene diamin: II. 800,785; 992,947. VI. 211,525; 341,991; 344,075; 365,409; 440,288; 462,414; 465,116; 502,912; 515,381; 516,203; 516,380; 525,245; 526,763; 536,431; 5574375 558,612; 560,448; 560,449; 561,694; 561,709; 572,723; 575,904; 578,580; 595,021; 603,009; 615,497; 619,503; 619,518; 628,814; 638,127; 647,236; 647,237; 679,221; 683,190; 717,550; 748,076; 832,393; 936,456; 946,050; 946,051; 971,112; 982,508; 987,417; 988,000; 997,061; 999,558; 1,012,619; 1,019,3215 1,023,120; 1,028,306; 1,052,647; 1,078,926; 1,082,581; 1,150,825; 1,209,154; 1,327,688. XV. 635,169; 695,835; 801,508; 904,809; 909,152; 909,153; 909,156. 3 or 4-Phenylene diamin: VI. 858,444. 523 524 4-Phenylene diamin: II. 298,998; 387,097; 863,761; 992,947; 1,105,554; 1,326,367. 211,671; 511,688; 512,167; 560,448; 561,694; 615,497; 620,574; 638,127; 640,010; 644,462; 679,221; 858,444; 936,450; 963,739; 999,558. 455,952; 636,065. 594,106; 594,107; 608,354; 641,587; 646,873; 708,662; 764,734; 782,905; 820,501; 904,809; 1,083,110; 1,440,833. (Ab) 1,277,056; VI. XIV. XV. 601,363; 641,588; 764,733; 813,643; 958,640; 1,083,489; 1,129,574; XXIII. 1,350,600. Acetyl VI. 526,763; 528,721; 561,700; 631,089; 648,623; 654,167; 654,168; 658,897; 662,122; 748,076; 859,930; 1,000,606; 1,363,886; 1,365,040; 1,372,439. Acetyl 2-chlor 7 731,460. as-Acetyl ethyl Cate iter ¢ 3-Phenylene diamin: acetyl, 4-sulfo 1,201,544. 3'-Amino benzoyl VI. 2,362,936. 4-Phenylene diamin: 3’-Amino benzoyl VI. 1,153,555. Benzoyl, 3-sulfo VI. 936,951. 3-Phenylene diamin: 4-Chlor VI. 657,064; 1,014,982; 1,014,984. 5-Chlor VI. 657,065. 4-Phenylene diamin, 2.6-Dichlor: XV. 779,860. XXII. 770,860. 3-Phenylene diamin: Di-formyl XV. 720,874: as-Dimethy]l, 1,455,486. 4-Phenylene diamin: Dimethyl XV. 679,199; 698,555; 763,320; 776,264. XXII. 679,199; 776,264. as-Dimethy 2 567,055 2 1%, 206,232: XV. 696,751; 728,623; 776,264; 778,478; 821,378. 3-Phenylene diamin: 2.4-Dinitro 6-chlor 4'-4”-dioxy diphenyl XV. 688,646. 4.6-Dinitro 2’4”-dioxy diphenyl 650,326. 4'.4”-Dioxy 3'.3”’-dicarbo diphenyl 4.6- dinitro XV. 648,753. 4’.4”-Dioxy diphenyl 4.6-dinitro V.. 648,755. > : 4’.4”-Dioxy 3’.3”-disulfo diphenyl 4.6- dinitro XV. 648,754. Phenylene diamin disulfo: VI. 778,610. 3-Phenylene diamin: disulfo VI. - 524,261; 524,202 631,010; 1. 8592930- 2.5-disulfo VI. 906,422. as-Ethyl dimethyl X. 1,455,487. Formyl DIGEST OF PATENTS VI. 971,111; 971,112; 1,052,647. Formyl, 4-sulfo VI. 999,944. VI. (972,112: 4-Phenylene diamin: 2.6-disulfo VI. 1,474,587. Methyl VI. 754,315. 3-Phenylene diamin: Nitro VI. 545,333; 568,549; 611,663; 631,610; 631,011; 995,160; 1,051,859. 4-Nitro VI. 964,919. 3/-Nitro benzoyl VI. er i8saias 4-Phenylene diamin: 4’-Nitro VI. 941,088. 3-Nitro acetyl VI. 792,032; 792,033% . gm Iste retara es, 4’-Nitro benzoyl 792,034; VI. 941,088 3/-Nitro benzoyl, 3-sulfo VI, 1,104,824. Nitro diacetyl XV. 738,027. Oxalyl VI. 999,797; 1,125,050. Oxalyl, sulfo VI. 1,078,926; 1,150,656. oxaminic acid VI. 1,009,745. 3-Phenylene diamin: sulfo VI. 656,120; 658,506; 658,507; 1,009,952. 4-sulfo VI. 946,050; 963,739; 1,026,984. 4-Phenylene diamin: sulfo XXII. 798,807. 3-sulfo ITT. 1,106,422: VI. 687,171; 936,051. 4'-tolyl sulfone VI. 1,359,969. 3-Phenylene diamin, Trimethyl ammon- ium: VI. 602,637; 602,638; 602,639; 602,640; 617,544; 626,913. Phloroglucin: XXIV. (m) 1,120,700. Phosgene: ITT. VI. 1,025,195; 1,038,003. 430,533; 430,534; 430,535; 662,122; 663,408 607,171; 935,016; 939,017; 935,018; 978,580; 986,287; 999,944; 1,001,183; 1,006,051; 1,006,920; 1,024,031; 1,032,797; 1,052,135; 1,076,756; 1,087,427; 1,087,428; XV. 1,081,508. XVIII. 290,856; 327,953; 333,861; 501,434. XXIV. (m) 501,235; 1,308,071. Phrenthrene, Oxy-thio, carbo: VII. 888,852. Phthalamin: VI. Vert T80: sulfo derivatives VIL 21280; Phthalein: XIX. 1,054,247. Phthalie acid: XIX. 413,048; 990,224. XXII. 708,171 Amino Se ines ns, ee et Tee INTERMEDIATE INDEX 525 VI. 297,852. 3-Amino VII. 540,564. Dichlor XIX. 413,049. Tetra chlor XIX. 413,050. anhydride III. 902,895; 1,055,287; 1,196,127; 1,355,100. WE. 2,421,245. XV. 688,885. XIX. 377,349; 377,350; 456,081; 516,585; 576,222; 576,223; 578,578; 609,997; 609,998; 633,883; 1,381,503. OX D Lets 255,517.7 1,301,309313330,1923 1,444,068; 1,465,689. XXIV. (pl) 1,424,137. anhydride 2-Chlor THI 4 55520. anhydride 4-Chlor TII. 929,442. anhydride, Tetra chlor XXII. 322,368. Phthalimid: Wie 1,322,052. XIX. 821,452. RALTV.. Gn) 621,319. Phthaloperinone: XV. 1,592,445; 1,126,630. Dinitro XV. 1,081,602. Phthaloyl chloride, Tere-: TIT. 1,459,536. Picramiec acid: 583,439; 624,256; 627,783; 646,711; 657,064; 657,065; 658,506; 658,507; 664,955; 671,904; 704,826; 740,767; 740,768; 807,289; 906,421; 924,232; 936,321; 987,362; 1,155,765; 1,199,233; 1,190,234; 1,217,042; 1,219,054; 1,281,243; 1,310,532; 1,408,363. XXII. 1,460,708. Picric acid: Mis 221 11s. XXII. 1,472,791. Picryl chloride: XALV: (m) 1,087,157. Pinene: XXIV. Piperazin: XXIV. (m) 709,321. Piperonal: XXIV. (m) 886,085; (p) 1,326,973. Polysaccharids: XV. 909,151; 909,152; 909,153. Primulin: VI. ,440,288; 524,261; 524,262; 656,120; 914,144; 1,107,164. (m) 1,411,859; (p) 1,323,589. sulfo XII. 656,857; 656,858; 656,859; 658,593. sulfo, Xylidin XIV. 951,048. Propiolie acid, 2-Nitro phenyl: VII. 227,470; 228,300; 233,458; 233,460; 235,193; 240,359; 250,035; 250,036; 251,499; 251,671; 259,260; 259,261. . N-Propyl alcohol: XXIV. (m) 950,936. Propyl alcohol: Diallyl amino XXIV. (m) 1,388,573. Iso- XXIV. (m) 1,412,937. t a-Methyl b-methyl y-dimethyl amino XXIV. (m) 1,474,567. Protocatechuic aldehyde: XXIV. (m) 1,399,144. Diacetyl XXIV. (m) 1,399,144. Purification: XXII. Purpurea: XXIV. Purpurin;: IIT. 509,425; 623,638; 749,913. (Sepn. of Crudes.) 722,336; 1,339,310; 1,409,588. (m) 1,391,705. sulfo III. 779,825. Pyranthrone: III. 955,105. Pyrazole anthrone: III. 1,329,435. Pyrazolone: VI. 844,845; 1,216,813. 3’-Amino phenyl, carbo VI. 936,367. Amino 1-phenyl, 3-carbo VI. 639,042. 3-Amino phenyl, carbo 1,094,448. 4'-Amino phenyl 2.4-dimethyl 3-oxymethyl XXIV. (m) 936,380. 3'/-Amino phenyl methyl VAL Inia 7 Sos: 4’-Amino phenyl methyl NV lieu t. t 23.2036 4’-Amino phenyl 2.3.4-trimethyl XXIV. (m) 990,310. Aryl methyl XII. 935,830. 4’-Brom phenyl 2.3-dimethyl 2 (in)! 1,053,240. 2'-Carbo phenyl methyl VI. 1,338,506. 2’-Chlor aryl methyl, sulfo XII. 1,098,600. 2’-Chlor phenyl methyl Vie 31,047,016; 41,100,471- 2’-Chlor phenyl methyl, 3-sulfo XII. 982,050. 2'-Chlor phenyl methyl, 4-sulfo XII. 1,098,600. 2’-Chlor phenyl methyl, 5-sulfo XII. 1,098,600. 2'-Chlor s’-sulfo phenyl, carbo VI. 1,084,363. 2’-Chlor 4’-sulfo phenyl methyl 1,172,061. 5’-sulfo phenyl methyl Vike 0272244 0el FAO hea te Dehydro thio sulfo tolyl methyl VI. 1,114,844. 21.5 /~ Dichlor phenyl methyl Wola she ,09T, 148. 2h! -Dichlor 4'-sulfo, phenyl methyl OVI. gor, 675. Dimethyl 4’-amino phenyl 2.3-dimethyl XXIV. (m) 680,278; 686,998; 686,999; 768,398. 4'.8/- Disuifo 2- aonthes methyl VI. 902,186: Nitro oxy phenyl methyl VI. 1,210,898. 4-Nitro phenyl, carbo XII. 627,690. 4'-Nitro phenyl methyl XII. 988,870. 4’-Nitro phenyl 2.3.4-trimethyl 4XXI I. 990,310. Phenyl VI. 739,069. XII. 808,919. Phenyl dimethyl (m) 674,686; 674,687. Phenyl 2.3-dimethyl 4-amino (m) 579,412; 1,056,881. Phenyl 2.3-dimethyl 4- -sulfamino (m) 1,347,083. Phenyl ethyl 526 DIGEST OF PATENTS XII. 464,861; 1,026,257. XXIV. (m) 464,861. Phenyl methyl (1- Phenyl 3-methyl 5-pyra- zolone) VI. 602,638; 791,524; 791,525; 980,521; 983,132; 984,900; 999,797; 1,001,286; 1,014,114; 1,021,304; 1,021,365; 1,024,080; 1,032,433; 1,183,831; 1,193,829. XII. 656,857; 731,670; 808,919; 1,026,257. XVIII. 1,023,977. Phenyl 3.4.4-trimethyl XXIV. (m) 1,017,699. Sulfo aryl methyl XII. 935,829; 935,830. s’-Sulfo 3’-carbo 2’-oxy phenyl methyl VI. 1,270,325; 1,286,411; 1,338,397. 4'-Sulfo phenyl, carbo VI. aie ek 839,605; 849,690; 849, XII. 656, 58: 656,859; 93553703 935,830; 1,010,919. 4’-Sulfo phenyl methyl VI. 959,109; 971,761; 971,762; 995,160; -1,021,366; 1,199,233; 1,199,234. XII. 656,859; 935,829; 935,830. Sulfo tolyl methy - KIT. 935,830. 4-Tolyl dimethyl XXIV. (m) 503,066. Pyridin: XV. 661,907. XIX. 913,514. XXII. 1,290,124; 1,414,441; 1,416,205; 1,416,206. XXIV. (f) 464,772. Amino benzy VI. 1,087,427. 4’-Amino benzyl VI. _ 1,073,754; 1,074,946. Amino benzyl, chioride VI. 626,933. Pyridinium chloride, 2’.4’-Dinitro phenyl: XIX. 913,513. Pyrimidin: 4-Imino 2.6-dioxy XXII. 811,826; 811,827. Alkyl 4-imino 2.6-dioxy XXII. 811,828; 811,829. 4.5-Dinitro INS Veer ear bere 2-Oxy XXII. 848,791. Pyrocatechol, Methyl amino aceto: XXIV. (m) 1,423,101. Pyrogallie acid: VI. 548,460. Pyrogallol: III. 443,402. Wik (220,lids XVIII 478,005. XIX. 1,055,864; 1,194,380. XXII. 1,434,593. XXIV. (p) 767,815. disulfo XIX. 1,106,185. XX.) 1,003;257 Pyroracemie acid: MI.) 257,812; )257,013. XXIV. (m) 1,197,462. Pyruvie acid: XXIV. (m) 1,138,936. Quinaldin: XXII. 309,035. hydro base XXII. 316,249. Methoxy and ethoxy XXII. 316,248. Tolu- XIII. 780,741; 805,143. Quinazolin, 2.4-Dioxy: VEO Ver. OLr2ons: Quinie acid: XXIV. (m) 690,804. Quinicin, Phenyl methyl oxy: XXII. 348,483. Quinizarin: III. 599,426; 599,427. Quinol: XXII. 1,322,580. Quinolin: XXII. 241,738. XXIV. (m) 273,498; 254,098; 282,488; 1,063,099. 5-Amino 8-ethoxy XXIV. (m) 512,590. Chlor iod XXII. 332,358. Dihydro iso-, derivatives XXIV. (m) 1,437,802. 2.4-Dimethyl 6-ethoxy, ethiodide XIII. 1,437,674. 1.5-Dioxy VI. 806,077. VI. 1,052,031; 1,073,754; 1,074,946. VI. 914,144; 924,232; 961,355. 8-Methoxy 2-phenyl, 4-carbo XXIV. (m) 1,045,377; 1,045,378. Methyl XXII. 268,543. 6-Methyl 2- -phenyl, 4-carbo XXIV. (m) 1,045,379; 1,045,759. Oxy XXII. 237,917; 237,918; 270,045; 906,918. XXIV. (m) 466,708. 2-Oxy XXIV. (m) 563,116; 906,918. 4-Oxy VI. 558,613. 8-Oxy VI. 1,419,500. Oxy hydro ethyl XXIV. (m) 273,498. 8-Oxy, 5-sulfo VI. 1,405,687. 2-Phenyl, 4-carbo MAILTO FT 07558 72, XXIV. (m) 1,076,160; 1,086,881; 1,091,870; 1,306,439; 1,336,9525 1,378,3433 1,434,306. sulfo XXIV. (m) 276,796; 1,408,462. Tolu-, methyl iodide XIII. 805,143. Quinone: III. 1,046,498; 1,052,520. XV. $23,138 Re. 11,050. XXIT. 71,328,631; 1,322,500: chlorimid XV. 1,440,681. dianili III. 1,009,981. 3.6-Dichlor 2.5-dianilino . ATES O28: 4’.5”-Diphenetidino dichlor II 1,065,063. Reduction: XXII. 256,330; 691,132; 700,671; 700,672; 714,428; 736,204; 736,205; 736,206; 738,404; 742,797; 1,345,589; 1,358,324. Resorcinol: 769,715. VI. 211,525; 260,359; 297,852; 361,404; 384,342; 399,581; 452,197; 509,623; 515,100; 516,381; 571,933; 572:7233 615,497; 626,913; 946,052; 969,450; 983,805; 1,023,120; 1,074,429; 1,082,924; 1,082,925; INTERMEDIATE INDEX 527 1,087,430; 1,090,379; 1,125,050; AALV (mM). 1,183,711: ¥5020,400; 13150,8253 1,1535555; Ethyl tolu- 1,169,329; 1,173,077; 1,180,985; XV. 829,740. 1,185,413; 1,232,056; 1,365,706; Salicyl aldehyde: 1,422,866. XVIII. 866 . 9359. & 615,232. MAI. 1,380,277: XV. es 630,952; 801,598; Salicyl thio acetic acid: 1,319,052. XVIII. 501,434. XIX. 596,333; 609,997; 1,055,885. XXII. 1,314,138; 1,406,745; 1,446,550; 1,446,551. XXIV. (m) 966,820. alphyl derivatives XXII. 252,782. Chlor 5 XIX. 990,224. Dinitroso ds 413,724. Nitro, disulfo XIX. 1,055,885. sulfo XIX. 1,002,825. 1.2.4-Resorcylie acid: VI. 528,965; 1,437,758. Nitro XIX. 1,055,885. Retene: VI. 1,395,238. Retenequinone: XIV. 386,709. Rhodamin: XIX. 489,923; 645,78. Diethyl XIX. 516,584; 613,926; 641,184. Diethyl benzyl XIX. 645,781. Diethyl homo XIX. 516,585. .2’ or 4’-Ditolyl XIX. 438,053. Tetra ethyl XIX. 516,588; 646,794. Tetra methyl XIX. 516,589. as-Rhodamin: XIX. 584,119. Dialkyl XIX. 675,215. Trimethyl, ethyl ether, IDX, 043,371. Rhodol: Dimethyl, ethyl ether, WA © O13, 113. Dimethyl, methyl ether, 625,536. Dimethyl, sulfo XIX. 1,055,864. sulfo XIX. 1,106,185. Rosanilin: XVIII. 32,965; 43,066; 204,798; 250,247; 262,680; 421,049. Resindulin: Phenyl, sulfo 524,221; §24,222. XV. 796,443. Rosolie acid: XVIII. 589,766; 591,309. Safranin: VI. 524,251; 524,254; 649,728. VI. 649,727. VI. 524,252; 524,253. Dimethyl pheno- VI. 1,032,433. Tolu- Salicylie acid: III. VII. 831,844; 836,309; 841,008; 848,354; 848,355; 850,827; 867,305; 867,715; 887,609. Acetyl 4-amino, VII. 867,306; 872,585; 968,697. Acetyl 5-amino VII. 881,157. 4-Chlor VII. 915,346. 476,491; 957,125; 999,785. VI. 221,118; 329,638; 329,639; 375,930; 380,067; 396,294; 398,990; 399,581; 401,024; 401,634; 406,670; 424,019; 430,533; 430,535; 431,207; 476,393; 479,515; 493,583; 503,148; 514,931; 515,897; 516,468; 535,036; 536,878; 555,359; 555,058; 567,413; 588,183; 602,858; 603,090; 603,646; 603,647; 603,648; 606,439; 608,024; 613,643; 613,644; 622,961; 628,721; 631,089; 638,127; 640,010; 666,867; 678,323; 679,974; 713,507; 718,028; 718,032; 724,894; 818,981; 902,186; 943,536; 949,633; 959,109; 971,762; 974,346; 991,750; 995,161; 1,009,745 1,024,308; 1,075,134; 1,099,676; 1,126,489; 1,157,169; 1,264,604; 1,282,356; 1,310,532; 1,474,587. XIV. 350,229. XV. 909,154. XVIII. 410,739; 476,414; 603,300; 609,599; 877,053. XIX. 1,403,888 XXII. 1,380,277 XXIV. (m) 503,066; 680,278; 830,043; 922,995; 1,338,297; (f) 1,427,400. benzyl ester XXIV. (m) 1,436,304. ethyl ester XXIV. (m) 563,993. Acetyl XXIV. (m) 811,884; 1,058,904; 1,063,099; 1,181,485; 1,321,307; 1,431,863 Acetyl, benzyl ester XIV. (m) 1,436,304. Amino VI. 438,438; 514,931; 546,070. XV. 648,753. XXII. 648,753. 2-Amino VI. 818,981. 4-Amino VI. 452,197; 464,775; 502,368; 502,369; 509,623. XIV. 636,065. XV. 628,608; 701,435. 4-Amino, methyl ester XXIV. (m) 619,549. 3’-Amino 4’-anisoyl 4’amino Wis 31,007,230. 6-Amino 4-chlor VI. 716,342. Amino sulfo VI. 655,529. 2-Amino sulfo VI. 1,282,356. 2-Amino 4-sulfo VI. 1,234,894. Anilino 528 DIGEST OF PATENTS XIX. 1,403,888. Sulfobenzid, 3.3'-Dinitro 4.4’-diamino: chloride IX. 1,166,808. XL Ve Gm) 915075,5S0. Sulfonation: Dinitro XV. 711,038. 6-Methyl 4-amino Wis et,1 4.7 70s 5-Nitro XXIV. (m) 563,993. 4-Nitro 6-Amino VI. 704,825; 704,826; 907,999. 5-Nitro 3-amino VI. 1,382,196. 4'-Nitro phenyl XXIV. (m) 492,868. Oxy, methyl ester XXIV. (m) 880,171. sulfo XXIV. (t)_ 1,344,950. shee and derivatives (See Thio salicylic acid. Sodamid: VII. 680,395; 704,804; 722,793. Stearie acid: VI, 002,021: Stearic acid anilid and derivatives: (See Anilid, Stearic acid.) Stilbene: 4”-Amino benzoyl 4’-amino benzoyl di- amino, disulfo VI. 1,059,670. VI. 360,792; 456,628; 456,897. 3.3’/-Diamino dibenzoyl diamino, disulfo VI. 1,082,924. Diamino dimethyl, sulfide VI. 418,657. 4.4'-Diamino, 2.2’-disulfo XIV. 350,229; 350,230; 360,553. Dinitro, disulfo VI. 903,284. Dinitro, 2.2’-disulfo XVIII. 668,580. 4.4'-Dinitro, 2.2'-disulfo ALVe 350,220; 350,230; Suceinie acid: XXIV. (m) 1,439,605. dibenzyl ester XXIV. (m) 1,439,605. anhydride Le aa 252504. XXII. 821,201. XXIV. (m) 768,562; 821,291. dialdehyde XXIV. (m) 1,419,092. Sulfanilie acid: Ill. 644,333; 707:373; 740;913; 754,768; 779,825; 787,824. VI. 210,054; 225,908; 253,598; 269,359; 277,182; 285,335; 309,882; 333,041; 399,581; 425,885; 466,202; 468,142; Biz FiOS eh TOs 22 hed.cOns 524,665; 543,747; 543,748; 590,088; 593,347; 593,790; 606,439; 618,963; 644,334; 719,048; 728,388; 741,936; 798,098; 903,284; 912,182; 932,812; 935,016; 978,580; 1,020,756; 1,078,503; 1,078,504; 1,106,781. IX. 666,627. XIV. 386,709; 951,047; 951,049. XV. 601,364; 601,365; 608,354; 608.3555 712,176: XXIV. (m) 602,646. 2-Sualfanilie acid: WE. (920,053 5 1,125,873. XXII. 88,979; 1,300,227; 1,300,228; 1,301,360; 1,301,785; 1,321,994; 1,332,203; 1,390,241; 1,396,320; 1,422,564. Suprarenin HCl: XXIV. (m) 1,472,298. Tannie acid: XXIV. (m) 533,718; 598,914; 607,172; 658,747; 659,204; 1,183,711. Tar bases: XXII. 1,339,310. Tartaric acid: XXIV. (m)e 2,423, to" XxX. Obs 2325 Dioxy XII. 324,630; 935,370; 969,428; 972,951; 1,010,919; 1,109,919. Tartronie acid, Amino phenyl: XVILIS “707. 6mae XXIV. (m) 676,850. Tetrazotie acid, Amino: XXII. 546,604. Theobromin, sodium: XXIV. (m)_ 1,414,333. Thiazin, 4.4’Dioxy: XV. 6012464: Thiocarbanilid: VII. 647,281. XXIV. (pl) 1,422,506; 1,477,805. Thionapthene derivatives: (See Naph- thene, Thio.) Thiophene: XXII. 1,085,708. XXIV. (m) 1,350,408. 1.2-Naphthoxy VII. 1,434,983. Naphthalene 1.2.5.6-bis=oxy- VII. 1,444,277. Thio salicylie acid: TII. 1,007,104; 1,026,621; 1,065,102. VII. 850,827; 867,679; 943,560; 943,561. XXII. 943,560. w-Dichlor vinyl VII. 910,839. Ethylene bis- VII. 949,592. VII. 804,004. Thio teluidin derivatives: Thio.) Thymol: XXII. Tolidin: VI. 329,632; 329,633; 363,502; 375,848; 375,930; 381,132; 394,425; 394,841; 395,634; 401,024; 412,149; 416,145; 417,207; Re. 11,1793; 417,296; 462,415; 462,824; 468,049; 468,539; 408,759; 506,284; 515,807; 516,381; 516,756; 516,759; 519,523; 521,005; 534,5733 544,700; 601,859; 602,855; 602,856; 602,857; 606,436; 613,646; 619,503; 620,369; 639,042; 670,398; 832,3933 959,109; 974,3463 1,281,938; 1,383,710. 2.2'-Folidin: VI. 366,678; 498,873; 501,118; 516,604; 516,758; 521,985; 541,859; 556,298; 585,104. 2.3’/-Tolidin: VI. 429,350. 3.3/-Tolidin: VI. 971,761; 971,762; 995,161; 1,071,832; 1,071,833. Tolidin, Diisopropyl: VI. 1,314,925; 1,314,926. (See Toluidin, 1,449,121. ae ee ee ere <«z ee ee ee ee eee we og it * INTERMEDIATE INDEX 1.2-Toloxazin: Ill. 729,073. Toluene: III. 929,442. Vive 3845356. VII. 259,629. XVIII. 603,016; 688,967. we rePea tee245049% (3,334;0333 1533953173 1,365,849; 1,419,124; 1,430,585; 1,458,491. XXIV. (£) 319,082; 551,131; 648,568; 692,598. Amino azo XXIV. (m) 1,076,840. Amino azo, sulfo XIV. 951,047. iV te 0,397.5) 201,707. 2-Chlor III. 902,895. XXII. 902,895. 4-Chlor 2-nitro VII. 677,239. 5-Chlor, 3-sulfo XII. 935,370. 3.3/-Diamino azoxy Wile i323'2,056. 2.4-Dinitro, 6-sulfo XV. 606,193. 2.4-disulfo MIS, 7,292;050. 2-Nitro Wit. 673,887. Mew 145 0,715. VI. 360,792. DEL Vin 3'51052 202) 350,230; XVIII. 541,572. 2-Toluene 4-Nitro, sulfamid: XXIV. (£) 692,863. Toluene: 4-Nitro 2-sulfo XIV. 350,229; 350,230; 360,553; 395,115; 396,527; 455,952 601,063; 636,065; 951,046; 951,047; 951,048; 951,049. XVIII. 688,580. 4-Nitro, sulfo VI. 644,462. XV. 1,053,676. sulfamid XXIV.- (f£) 319,082. sulfinic acid PUT 1,261,858. Pelee 407 57 Ves XXIV. (f£) 667,861. XXII. 602,682. VIDS} 772,500. Vo 608,220. XVIII. 673,632. XXII. 1,292,950. 4-sulfo chloride VI. 800,914. XVIII. 866,350. XXII. 1,442,818. AALVe (£). 319,082. (m) 603,195. sulfone anilid VI. 1,042,198. Trinitro 1,268,803. XXIV. (e) 1,297,524; 1,309,5593 1,450,675. 4-Tolaiec acid: SN aie t 3 1O0;7'5 0. Toluidin: III. 688,576. bei 333503055) 300,192) VII. 955,699. XIV. 613,911. XVIII. 501,434. 529 2-Toluidin: VI. 211,671; 406,669; 406,670; 524,251; 719,049; 792,600; 794,568; 813,155; 837,736; 989,953; 1,006,929; 1,022,612; 1,024,308; 1,338,397. VIL. 627,652: ¥,243,771. XII. 1,098,600. XV. 709,151; 742,189; 958,640. XVIII. 471,638; 473,453; 647,834. XIX, 605,781. XXII. 709,151; 742,189. 3-Toluidin: VI. 602,637; 602,638; 602,639; 610,345; 617,544; 626,933; 1,028,140; 1,029,639; 1,051,859; 1,052,031; 1,073,902; 1,087,428; I,149,575- XVIII. 688,967. 4-Toluidin: III. 509,426; 599,427; 603,659; 608,338; 640,986; 654,294; 654,295; 656,081; 666,594; 666,702; 673,691; 675,572; 675.5733 675,574; 675,575; 687,657; 687,658; 688,645; 690,292; 715,662; 722,719; 723,125; 734,325; 734,866; 738,614; 764,837; 778,036; 812,599; 932,290; 1,026,557 1,070,196; 1,078,505; 1,131,516; 1,207,702: VI. 211,671; 498,404; 675,632; 1,065,950. VII. 310,604. XII. 935,829; 1,098,600. XVIII. 423,341; 995,494; 1,218,232; 1,244,149. NXT. 722,710; 3,441,055. XXEVG (m) 1,138,936: 2-Toluidin, Acetyl 4-amino: XXII. 902,150. Acetyl, 4-sulfo I. 935,371. Acidyl, 5-sulfo XII. 935,370. Toluidin, Amino azoxy: Wile 25003762. 2-Toluidin, Azoxy: Vin (505,764. 3-Toluidin, Azoxy: Vii 036,367. 2-Toluidin formaldehyde Anhydro: XVIII. 471,638. 2-Toluidin, Benzyl: XVIII. 567,567. Benzyl azimino = -903,020- Benzyl, disulfo XVIII. 580,188. Benzyl, sulfo XVIII. 580,186. 4-Tolaidin: 3-Chlor VI. 765,069; 765,080. 5-Chlor 2 nitro VI. 1,038,884. 2-Toluidin: 3-Chlor, 5-sulfo XII. 935,370. 6-Chlor, 4-sulfo VI. 935,371; 1,027,148. 3-Toluidin: 4-Chlor, 6-sulfo VI.” 733,290. 6-Chlor, 4-sulfo VI. 083,486. 4-Toluidin, 3-Chlor, 6-sulfo: VI. 759,716. 2-Toluidin: . 3-Chlor 5-sulfo, hydrazin XII. 935,370. . ‘ 4-Chlor, xanthogenic acid 530 DIGEST OF PATENTS VII. 906,029. Tolunidin, Dehydro thio: VI. 428,629; 515,339; 524,005; 5324793 535,037; 543,539; 588,180; 1,159,386. XV. 802,455. Acetyl VI. 1,125,073. sulfo XII. 658,593. XIV. 951,048. 4-Toluidin, Dehydro thio, sulfo VI. 398,990; 404,097; 441,945. Toluidin 2.2’-disulfo: VI. 1,264,604. 3-Toluidin, 4-Ethoxy: IV. 1,452,083. 4-Toluidin, 3-Ethoxy: VI. 987,362. 2-Toluidin, Ethyl: XV. 732,090. XVIII. 472,091. 4-Toluidin, Ethyl: VII. 619,884. 3-Toluidin: Ethyl benzyl AV ELT st, 218,292: Ethyl sulfo benzyl XVIII. 1,101,770. Ethyl 4’-sulfo benzyl VI. 1,054,348. 4-Methoxy VI. 1,209,154. 4-Toluidin, 5-Methoxy 2-nitro: VI. 1,038,884. Toluidin, Methyl: b a2Oa ts: 2-Toluidin: Methyl XVIII. 519,071; 525,627. Methyl, sulfo XVIII. 580,187. Toluidin: Nitro Viveetis25. 3-Nitro VI. 380,927. 2-Teluidin, nitro.) 2-Toluidin, 5-Nitro (NH,=1): VI. 500,761; 954,960; 1,034,853; 1,052,145; 1,122,564; 1,215,359. IX. 763,756; 763,765. 4-Toluidin, 3-Nitro, (NH,=1): VI as 2647T 35 01,8 o3s370° IX. 763,765. YToluidin: Nitroso dimethyl X. 420,311. sulfo VI. 211,671; 333,042; 466,841. XII. 935,830. 4-Toluidin sulfo: 4-Nitro: (See VI. 428,629. 2-Tolnidin: 4-sulfo XII. 935,830; 1,098,600. XIV. 386,709. 5-sulfo XII. 935,830; 1,098,600. XM VIEL. '538;027- 4-Toluaidin 3-sulfo: VI. 743,071; 849,690. XII. 935,830; 935,870; 1,098,600. XIV. 350,229; 386,709. XXII. 1,441,655. 2-Toluidin s-sulfo 2/-anisidid: VI. 1,005,233. Toluidin sulfon anilid: VI. 978,439. 4-Tolnidin 2-sulfon anilid: VI. 965,882; 989,954. 2-Toluidin, 5- Tolyl 3-aldehyde: VII. 662,073; 662,074; 662,075. 4.6-Dichlor XVIII. 1,042,493. Nitro VII. 662,076. sulfo XVIII. 2-sulfo XXII. 709,159. 4-Toluyl, 3-Nitro, chloride: XXIV. (m) 1,317,251. Toluylene diamin: VI. §24,251; 1,314,922. 2.6-Toluylene diamin: VI. 1,000,606. 3-Toluylene diamin: 709,160. (1.3.4-NH,. NH,. II. 739,071. VI. 365,409; 375,930; 395,634; 516,604; 541,750; 582,958; 602,857; 608,024; 620,574; 639,041; 671,543; 688,478; 718,032; 971,III; 999,713. XV. 640,559; 688,885; 712,747; 714,542; 722,630; 723,448; 782,905; 813,643; 829,740; 895,637; 896,916; 934,302; 934,303; 1,165,531; 1,251,388; 1,251,389; 1,327,688. XXII. 829,740. 4-Tolaylene diamin: (1.4.3-NH,. NH,,. CH,.) VI. 221,120; o16:923- XIV. 636,065. XV. 641,589; 641,953; 641,954; 7731346; 866,939. Toluylene diamin: Acetyl XV. 785,675. 4-Toluylene diamin, as- Ethyl benzoyl: VI. 1,199,890. 3-Toluylene diamin, Formyl: I. 1,455,486; 1,455,487; 1,455,488. Toluylene diamin sulfo: XV. 746,926. 2.4-Toluylene diamin 6-sulfo: VI. 516,380. 2.6-Toluylene diamin 4-sulfo: VI. 465,116; 407,032; 558,612; 558,614; 568,549; 588,614; 639,040; 644,291; 644,292; 982,507; 982,508; 1,123,263. 3-Toluylene diamin sulfo: VI. 619,503; 748,076. 3-Toluylene diamin 5-sulfo: VI. 1,006,929; 1,024,031; 4,052,647% 1,183,378. 3-Tolaylene diamin 6-sulfo: VI. 603,090; 946,051. 3-Toluylene diamin 4-tolyl sulfonamid: VI. 704,825; 704,826. Toluylene di-urea: XV. 760,110. ; 2-Toluyliec acid, 4-Chlor 6-nitro: VII. 892,897. Tolyl: 3-aldehyde VII. 276,889; 276,890. 5-aldehyde VII. 276,890. Tolylamin, 2.4-Dinitrophenyl oxy: XV. 660,067. 2-Tolylamin, 3’-Oxy phenyl: XIX. 609,997. 4-Tolylamin, 3/-Oxy phenyl: XVIII. 501,434. Tolylamin, Phenyl oxy: XV. 660,097. 2-Tolyl glycin: VII. 746,065. q + i] i e . vd ia % INTERMEDIATE INDEX 531 2-Tolyl glycocol: VWilie 617,052; 619,883; 621,652. 4-Toly!I glycocol carbo, diethyl ester: Vinyl acetate: (See Acetic acid, vinyl ester.) Violanthrene, Iso: III. 1,003,268. VII. 644,326. Xanthine. 3.7-Dimethyl: 4-Tolyl sulfonamid, 1-Naphthol: XXIV. (m) 1,415,700. XV. 843,156. Xanthogenie acid: Trimethyl arsen, or ethyl deriv: VII. 867,305; 872,085; 877,743; XXIV. (m) 1,308,413. 881,157; 881,158; 881,159; Triphenyl carbinol: 892,897; 916,030. Dimethyl 3-amino tetramethyl 4-diamino 4-Chlor 2-toluidin (See 2-Toluidin 4- XVIII. 437,089. pia Chlor xanthogenic acid) 3-oxy tetramethyl diamino, disulfo Xanthone, 5-Amino anthraquinone 1.2-phen XVIII. 463,898; 490,408. thio: Triphenylimethane: III. 999,785. 3-Amino tetraethyl diamino Xylene: XVIII. 412,614; 453,477. XXIT. 1,311,848; 1,434,593. Diamino Amino azo Vi, 1,160,471; 1,172,061. VI. 246,221. 3-Nitro diamino Amino azo, sulfo Ea OO Ley. VI. 256,378. 3-Oxy UF teteasthy! diamino, disulfo w-Tetra or hexachlor XVIII. 1,478,015. XIV. 1,459,536. 3-Oxy tetramethyl diamino, disulfo 3-Xylene: XVIII. 615,472. VII. 276,880. 4-Toluidino dimethyl dioxy, dicarbo XVIII. 1,219,166. XVIII. 1,244,149. XXII. 1,477,058. Triphenyl stibine dibromide: 2.4-Xylenol, 6-Amino: 2.4-Xylidin 6-sulfo: Waleryl bromide, Iso: TI ot 447,658, XXIV. (m) 998,726. 3-Xylidin 6-sulfo: Vanillin: VI. 839,605; 933,562. XXIV. (f) 1,138,936; 1,329,272; Yohimbin: (m) 1,138,936. XXIV. (m) 1,305,462. XXIV. (m) 1,060,765. VI. 826,281. Uramil, 1.3.7- Trimethy1: sym-Xylenol 2-carbo: XXIV. (m) 667,388. XVIII. 1,034,173. Urea: Xylidin: III. 928,891; 1,004,107. VI. 210,233; 211,671; 277,182; VI. 935,016. 333,035; 418,657; 456,627; XXII. 1,173,550; 1,274,503; 1,292,019; 456,897; 677,516. 1,326,045; 1,344,673; 1,369,383; XIII. 677,517. 1,417,277; 1,419,157; 1,429,483; XIV. 613,911. 1,429,953. 2.4-Kylidin: XXIV. (m) 773,251; 1,331,712. VII. 881,624. Dimethyl diphenyl XXII. 1,441,655 ALIS "3,393,597. 2.6-KX ylidin: Di or tetra alkyl diaryl VI. 656,620; 1,084,363. XXII. T,307,5 70. 3-Xylidin: 5.5’-Dioxy 7.7’-disulfo 1.2’-dinapthol VI. 916,161; 1,073,903. XXII. 675, 630. : sym-3-Xylidin: 5.5’-Dioxy 7.7’-disulfo 1.2’-dinapthol thio XVIII. 676,555. AXII,, © 675,631. 4-Xylidin: 5.5’-Dioxy 7.7’-disulfo 2.2’-dinaphthyl thio VI. 591,616; 602,540; 877,644; XXII. 653,678. 931,424; 933,447; 933,448; 5.6’-Dioxy 7.8’-disulfo 2.2’-dinaphthyl thio 033,562; 943,470; 1,020,756; XXII. 675,628. 1,092,842; 1,180,985. Urethane: Xylidin: Ethyl Dehydro thio XXIV. (m) 1,424,236. XII. 658,593. 4-Oxy phenyl ethyl Ethyl . XXIV. Fie 537,841; 541,489. View2515163- ps-Urie acid Nitro XXIV. (m) 667,388. VI. 231,925: Urie acid, 1.3.7-Trimethyl: Rarer heats: Tepes Mem E 7g Sen) 867,358. 2.4-Xylidin, 6-Nitro: Uvitie acid: VII. 881,159. Oxy Xylidin Primulin sulfo: (See Primulin.) asa 488,290. Xylidin sulfo: 7 XIV. 386,709. VI. 493,413. ott. PATENTEE INDEX. The names in this index are arranged alphabetically, with state or country of origin of patentee, abridged name of assignee, and patent numbers by dye groups. (For key to column 3 see Assignee Index.) Prefixes such as von, de or du, considered as part of the name, determine its — Names employing the umlaut are arranged as though the vowel For instance, Konig is placed as though alphabetical order. were followed by the indicated letter e. spelled Koenig. Letters in parentheses before patent numbers, last column, indicate the sub- divisions of groups XXIII and XXIV, as follows: XXIII.—APppiicarions: (Ab) Anilin black. (Ox) Oxazin. (An) Anthraquinone. (Su) Sulfur. XXIV.—FINISHED PRODUCTS OTHER THAN DYES: (e) Explosives. (f) Flavors and perfumes. (AI) Azine, indulin. (Tr) Triphenylmethane. (m) Medicinals. (Az) Azo. (Xa) Xanthone. (p) Photo chemicals. (In) Indigo (pl) Plastics. (Nt) Nitro. (t) Tannins, synthetic. (Ni) Nitroso. COUNTRY DYE PATENTEE OR STATE ASSIGNEE GROUP PATENT NUMBERS Abel, (yulitis 1.0 veg sare sos oe ne Gere eee Badische..... XV | 544,050; 679,199; Re. 11,973. and Fritz Kalkow ......... GeF. ca cae Badische..... XV esoeey 650,293; 658,055; ’ 92,174. and Arthur Luttringhaus .. |Ger....... Badische. ..'.. XV_| 775,428; 777,323; 790,167. ACh RPItz sce ky a cease eis aie mete Ger. cores. Boehringer... | XVIIT| 707,813. See hoe 708,511. : 1,053; (m)676 2 Ach, Lorenz ........ccsesecess GEftone.s Boehringer... | XXII bey hie Ame Saree XXIV | (m}948,084. and ean Sutter ...... ae Pore: Boehringer... peak (m)922,995. Achtmeyer, TR URE: a5 pCOMMEr ESE ouee Ae OU sieice cl Pelee occ alee holece lake 1 1,429,265; 267. Acker, Edwin. See A. Zitscher. pl) 1142952655 #.aeaeaes F. Kunert and A. Winther. ; Ackermann, Fritz ............. Getieisess Berlin. sic4es VI | 1,173,077. (See H. Geldermann) and Ewald Steinback ...... Ger sccm Basie... hee. III | 1,437,783. Adams, Carleton C. See A. R. Grob. ’ Adams, Elliot’ 0.0) ..ss5 abe sence Galrtse css and (Hi: U, Haller asa eee Ohio }..6: U. S. Govt...| XIII | 1,374,871; 1,374,872. and Louis E. Wise ....... IN a] Aree U. S. Govt... }| XIII | 1,338,346; 1,338,340. Adams, Roger (see O. Kamm) . jIll........ and E. H. Volwiler ....... litt eee Abbott....... XXIV (m) 1,360,994; 1,440,652; 1,476,934. Ahiam;- Chas..t.ceevicenaeteae Pata. u Pont. «—S>_—S>]_—S>]_aE>—Ee—__—>_——>—_—_———>—>>l>]ll>— oo —————_— PATENTEE pe yatiet ASSIGNEE | nous PATENT NUMBERS Pate EL CINTICH, Vs eek ccs ees Gers. csi is PIGChSty aa oe ste VI 210,233; Re. 9,986; Re. . 9,987; 233,465; 246,272; 250,038; 251,162; 251,163; 251,164. XXII 554,974. meee A IDETE. esas cats eyes des» Geri ie... Than. «0s XXIV | (£) 692,596. Bauschlicher, August ........ Aus.-Hng..| Roessler....., XXII | 608,019. Bayer, Friedrich (see C. UOT tg 0 SES ee eae ee Gervine «és Bayer ins: +33 VI 362,813; 363,502; 395,474. XXIII | (Az) 418,153. AZ LCT MP NEAK Wile lee uaisGis.e ess © Getsac esc Badische..... XXII 885,566. XXIII | (In) 657,307. and Theodor Wohlfahrt . |Ger....... Badische..... XXII | 793,559. Beach, Carl, Alvin Mittasch ...|Ger....... : and Carl Neresheimer ....|Ger....... Badische..... XXIT | 1,274,503. Ce ON Yvan se coechavavas 0s Getiis cnc: Hochsties .s.0. VI 844,845. XXIII | 1,002,118; 1,024,668. and Hermann Bablich ...|Ger....... Hochst....... XXIII | 666,256. and Albert Beil .......... eS aa Mochst,«.5 << VI__ | 623,697. ” XXII | 995,431; (Su) 680,472. and Wilhelm Suida ..... Aus.-Hng..|Hochst....... III 1,196,422. Hecker; ‘Pranz %%sii.i.s.s... Aus.-Hng. |Badische..... XXII | 885,567. Becker, Theodor. See A. Eichengriin. Beckers, William .....0¢00+:. in ey ere and Issac Dreyfus ....... ty eee Beckers...... XXIII | (An) 1,228,089. Beckl, Walter. See M. Conrad. Bedtord, Charles S.-....5.055. Enrng.....2 |eceesceceeees VI 409,384. Bedford, Clayton W. .......... Ohior.. Goodyear.... | XXIV | (pl)1,418,772; 1,477,805. and Robert I. Sibley ... |Ohio..... Goodyear..... XXIV | (pl) 1,418,771. Behaghel, Wilhelm .......... Gerace as ‘ and Gustav K. Schumann .|Ger...... ,|Badische..... VIL |772:775; 818,341. XXIL | 778,772. BORTENE, FORBRG oa ieee sss (CS Ce XXII | 667,358. Beil, Albert. See M. Becke. ; TT Be at 2 eae a ene Eng...... | cere ecereeees VII | 868,755. Benda, Louis (see P. Ehrlich) .|Ger....... Cassella...... I 1,427,431. XXIV | (m)1,408,974. Bender, Andrew J. ......... N. J... eee lereeeeesseeee XXIII | 1,301,360. enGet, Fritz oi is icc cee ees ein. Leonhardt.... I 503,305. VI 341,991; 344,075; 593,347>5 606,436; 606,438; 606,439. VII | 662,754; 662,755; 690,346. XI | 494,838. XIV | 350,229; 350,230; 360,553; 395,115; 396,527. XIX | 445,084- 06,437. and Michael Kammerer ...|Ger....... Leonhardt... he 489,623. and Bertram Mayer ...... Gerires es Leonhardt. ...| ywyyy | 673,632. and Gustav Schultz ...... C3 See Leonhardt... VI 360,792. Benedetti, Carlo O. .......... De Vance ss ; and A. P. and W. Vanse- NY , MW a wae Res ae f4 Aus e)WS wim oile,ece. 8 © 0.6 . et se Set ec 1 Ie OT RU I ee XTI 1,405,201. Berchelman, Wilhelm ......... Ger... ss: Elberfeld..... oH 764,837. Bayer aon 69167 ae Ill 958,850; 1,014,204; 1,045,805. erences meRUOOlt 2.55 onex «ws 6 Geri ns eae: Elberfeld.....| xqIq | 752,323; 780,741. Weredpit, Alfred: (o. ceces s+ 0s Ger....00. Bayer.......- VI 912,356. Bergdolt, Wilhelm (see A. OE Gy CSS ae ae Ger....... Bayer....... -| VI |963,739; 974,346; 1,009,952; 1,014,633; 1,052,647. Synthetic..... VI 1,201,544. Ber peliMeEClehe hs akic sc aus see Ger isnnone Wiilfing..... XXIV | (m)852,9903. Bergius, Friedrich. See K. H. Meyer. Berlinerblan, Joseph .......... Russia....|von Heyden..| XXIV | (f) 489,728. Bernhard, Eugen. See E. Zacharias. E Berns, Wilhelm .............. Geta ve Badische..... XXIII | (In) 690,347. Bernthsen, August ............ Gef....... Badische..... XVI_ | 282,836; 286,527. XXII | 282,835; 286,526. Bernthsen, Heinrich A. (see G. be PRMICEE See a a Sig's shad kb ¢ Geis sass. Badische..... XIX |516,584; 516,585; 645,781; 646,794; 821,452. and George F. Jaubert ....|Fr........ Badische..... VIII | 617,628. Ger.......{|Badische..... XXII | 625,637. 536 DIGEST OF PATENTS COUNTRY DYE PATENTEE OR STATE ASSIGNEE GROUP PATENT NUMBERS and Paul Julias ..5..5.... Get vas ss Badische..... VI | 521,095; 521,096; 545,333; 5551359; 558,344; 631,610; 631,611; 644,240. Bertheim, Alfred. See P. Ehrlich. Berthold, sierich nti os Gera sat Berlin. o.3. vi 983,805. Berton, Jacques E. See N. C. Armand. Bertram, Wilhelm. See A. Schmidt. Bertschmann, Albert .......... SwitZ....< | Bases: tooo ee VI 724,078. XIII | 852,158. XV_ | 665,726. Bethmann, Fritz. See A. Schmidt. Bettey, Ralph. See J. Wolff. Beudet, Maurice. See J. Koetschet. Beyer ye Brune, «scr sie she shee enn Gerenr cers and F. Schaar-Rosenberg .|Eng...... Badische..... XV 654,087. Bibus, BertranG cee eee eee ee Aus.-Hng.. and Rudolf Scheuble ...... Aus.-Hng..]... Tee ee XXIV | (m)830,043. Bidaud, Florentin .0o....-...-- Pree Soc. Chim....| XXIV] (f) 1,418,904. Bielschowski, Oscar ......-... Ne eee ee XXIII} (Ab) 343,793. Bierer; oy OSephi ei. cect eee see Switzen 2 en|| Dirandenieere XI 534,809. XIX | 551,885. and Charles de la Harpe ..|Switz..... Durand...... XI | 531,148. Bigelow, Chas. A. See H. A. Wollenberg. Bindley, William T. See A. W. Weller. Bischler, Augustus ........... Switz..... |Basle.....3; VII | 727,270; 761,440; 776,884; 839,099; 894,579. XIX | 759,657. XXII 78) 6p 86 : XXIV 7,361. Bissell “Dos Wyse eee Ww Viewer Nati Lys Gs if (ste D. I. Cutrown) tional......] XVIII| 1,478,015. ackmore, Enry DS. .-.- eee, ING WX sin Siete dl ete seinen eee : Blanchon; ‘Andre’. $08 .525 3. Seb A Pik hes XXIV | (m)854,452; 889,171. and (AugustinJA egret 02.1 Bro uiacs 5 1o5 ot ee ee XXIII} (In) 522,042. Blangey, Louis (see P. Julius and A. Luttringhaus) ...... (Sete, coy Badische..... IX 1,166,808. and Carl Immerheiser ....|Ger....... Badische..... VI E,073,952- Blank, August (see K. Krekeler) cn¢a.5 tues see ses Cer ee Bayer........ VI_ | 1,023,120; 1,051,859; 1,052,031. ; and Wilhelm Bergdolt ..../Ger....... Bayer. ..¢.55. VI | 971,111; 971,112; 1,082,923; 1,087,429. and C. Heidenreich ;..... Gére hte re Bayer.......- VI 1,056,493. and “cm ansenian.ereteni tect Ger 5a. ee. Bayer..-s50i VI 1,082,581; 1,082,924; 1,082,925; 1,087,430; 1,090,379. Synthetic VI} 1,125,050; 1,150,656. and Karl Heusner ........ Gera Bayer; ¢« 2% VI_ | 969,450. A. Israel and M. Herzberg/Ger..... St Bavyetl.cs ae VI | 561,694; 561,709. and Matthias Latten ...... Gf. ideas Bayetiivcen et VI_ | 1,006,051; 1,087,427; 1,087,428. : and Wladimir Rodinow ....|Ger....... Bayer... 4.0: XIV | 951,046; 951,047; 951,048; 951,049. BianksRubin vc... eee Ger! ores: Cassella...... VII | 620,562; 620,563. Bloch; :Beniot 4.0 iaav ame Pee ee ee II | 79,942; Re. 3,103. Block J Davidse: a. eee ee Ieee Sunbeam..... XXIII} 1,361,811. Bloede, "Victor Gun uwet et eee Mdsees oy Bloede.,..... XXIII} (Ab)570,117; 588,387; 588,388; (Az)593,192. Blom, Axel Vo oo vcak os ea ek Switein atl anaes XXII } 1,351,888. Blumenthal, Ferdinand. See O. Liebknecht. Blumfeldt, Alexander ........ Switza... Basle... ocee XXIV | (pl) 1,435,801. Bockmithl, Max and Gustav Ebert, 52. Seb acaeee cee Geren Hochst... shh XXIV | (im) 1,056,881. and Adolf Schwartz ...... Gere eo Hochet;, 2-5 XXIV | (m) 1,426,348. and Kurt Windisch ....... Grete SOF gens 3 Hochst. .5 0s XIX (see K. Schirmacher) Bryk, Ernst (see A. Schmidt) ./Ger....... Hsochetec. ase VII Bucherer, Hans T. .....s+.-- Get euss + Kalle, js uses VI (see C. Schraube) XXII Buchner, Max. .sscccescesens Géfiun as nk Boehringer...| XXII XXIII Bilow, -Catl esas woneenach ee rere ted sn Badische..... VI Birger, Joshua. See “A Ashworth. Bulk Mises iy canes nie Stem a Ger....... Bayer, 5.5). TI (see J. Flachslaender and K. P. Gralert) ' and Alfred Thauss ...... Ger....... Synthetic..... XV Bull, Henry and Carl UL. Maller ype, vs os Cheb eet Ger....... Badische..... XVIII Bundaman, Emile T. ..,-.2.°: Calif...... Point Loma..| XV Burckhardt, Rudolf (see C. de , ja Harpe} sic eannw ee ceee Switz...» |Durand..o.4 Vv Burdick, Alfred. 8. y.- 005% 4s FN PR eet and Elmer B. Vitet ....:. Tian: Abbott....... XXIV Burghart, Lloyd Me j.sse Lar rerie a's Sunbeam..... XXIII Ceresole, Maurice ........000. Geri cue: Badische..... XIX Chapin, Edward S. .......... MIARE oe och care Cree ae eink XV ANCE TI GeSSED (ips cas Mass...... Amer. Dye VI Chatheld,. Clas. Bo ....5.0... We daciee latvia Pleteeatens (Ss XXIII ee euiiGt, PLGUTA cick svc eshcces BENG eae: « fhm eat a hiets s XXIII Chebotaref, Leo F. .......0.. N. OY. National..... XXII Cheever, Joseph C. F. ........ Wee ce ei al tase heme eas eal XXII Chevalier, Philibert .......... Lg CORR ees (Cr rrr XVIII Christiansen, Jens Anton ..... SREP ee aaa? | ig os dee Se XXII Rte LMU OW TAN 6 oc es nee 65% RR dit Peer eenies + os XXII Rei. an bert t1,. osc s bes ees Mass...... Metalite...... XXI Relar ke MELOne (las sce cose hos N.Y: Eastman..... XXIV and William W. Hartman|N. Y. ...]|Eastman..... XXII Classen, Alexander .......... Eig Rag ray Elche gs Lee ght XXIV nue, meer H., Alfred Ree tee ae CUle weld 6.5 UE o's 1s caacese cess XV ee Albert, Bernhard Schoner and Otto Siebert ...|Ger....... Berliners cr VI Breet OP EICUTICH (occ cis ca cece’ Chey Rar teeal Keiie oMIaa e XXIII Clemm, August. See C. Clemm. REMOTATD; COMMS -. 5 5 os Coa ou we see oe B.ceseene and August Clemm ...... NPOR ee cig | ew eGee es inns XVIII Clingestein, Heinrich ......... POR Payeriies. sa VI Clover, Alphonso M. ......... Pama. eal oe so hee es XXIV Parke-Davis.. | XXIV Cobellis, Fabricius ............ rere ite sl Suiire coos eaak XXII Srobenzi, | Alpert... vse acces eae oo ae Hochet. ic. hg - SO PIETCS VEFeil ois cs san cese Nek and Harold W. Walker ...|N. Y. .../Com. Res XXIII Coen Jr, W.. Wesley .......; POU ote 1a aleve ee ae | BOUe, SC AREONCEs De nd once eke Pace aa etoe ctw aie piccem! ov XX ME RODESE RM ss nce ace ke « Chia. cx: Collins (1%) XXII BTR pores Sp XXIII Colman, James. See R Wolffenstein Conant, George A. .......... INVASS Feretiets | secraetnatedang eee XX Cone, Lee CTE oes din aa MTC Waar: Dowie cs VII Conklin, Theodore F. ........ WD leeerees tir al erstere ta crate wictetsse xX Conover, Courtney .......... fot Ba te ae Selden....... XXII and Harry D. Gibbs ..... ROaTGE ate 54 U. S. Govt XXII DORUG MON ee oe oy a sn os Co ee Héchst....... XXIII and Walter Beckh ........ ReOR ek Pe oaidcae re ace ase XXII memererry ATOM yd. ocacsc une . Switz : Geigy te olannis XVIII poke diesty J: .......2.... N. Klipstein (14)| XXIII Roombs, Frank By. si........ Cetitere et ln reece ek Cooper, Herman C. See R. H. McKee. Copthorne, Howard N. ....... Ly Resear and A. Te -Tannehill ..... DnB pee yaic:\tercatetets cites ate ss ase ech mee sie Pare isa Koppers..... Datta, Rasik Lal ........+---- [belch ye RM RAL SR cincrapsie and P. S. Varma .......-. Trdiat Geen nbe eto miciaee Davidis, Ernst. See J. Bammann. Davies, Arthur H. ........--+-- En pee Scot. Dyes... Davis, Alex Bo. 2s <\se.ce sees Ind Lilly c.f eens Davis, Frederick .........--- Hingis set Baversnasnees Davis, Tenney L. .......----. Mass......|]-eceeeececees de Grousseau, Edouard ....... Peetu and Auguste Vicongne ....|Fr........]--+-- We routes de Haen, Cath JilEw anes. 1 oe Gertie ec ccc cc cceces de la Harpe, Charles (see J. Bierer, C. Oswald and C. A. MMAVET) a 56 Gk ks gear ie emt SwitZiceen Durand... and Rudolph Burckhardt ..|Switz..... Durand...... and Charles Vaucher ..... Switziy oc. Durand.....- andwiies woretanecmate ies Switzer Diurand.sae and Ernst Bodmer ...... Switz..... | Durand... . and B.Zehntner’.......°. Switz.; <2 Durand... %< and pike Oswald a tiers cee Switz Durands.. sc Ges Lalande belie. esto. sae Bos touch tok gee de Montmollin, Guillaume ..... Switz Baste. 5.4.05 and Gerald Bonhote ..... Switz Baslestacke and Heinrich J. Spieler ..|Switz Baslershacscr and Josef Spieler ....... Switz Baslesecanntis Dean, Harry. Sée J. Turner. Dedicherny Fens i258 sos Os Getis>|(Cer.....s- (see B. Heymann, A. Israel and R. Kothe) and DMMyrtil Rahn ......./ Vio Dn eae Pavers awe VI_ | 843,077. and Richard Kothe ....... ariet. Bayete cee: VI | 858,444; 859,930. and H. Hoerlein ....... [ed ee Bayers.c. eae vI outer 978,438; 978,439; 959,954. aid AS Duss... ees oy Bayerse; . Elbert, Gustav. See M. ie eaieh: Bockmuhl. Rilis, Carleton s,s sore vee ges NS poe wires Ellis-Foster XV _ | 1,187,614; 1,274,351} 1,279,307. XXII | 1,306,221. ~ Ha ee Sais 1,365,046. and Alfred A. Wells ...... re ed pars PANN aici Bisaesser, \Emilsys seiana a ses oe Getiaccces Dablocst ee Vv 392,723; 524,677. ap « hoal d wise tabernae VI_ | 320,634. oer A ees bee Me 611,111. ah eatee aatee 548,158. Dahle axa os XV 611,112. Me Muiaviakatere panes 607,408. Elvert, ‘Heinrich. 645 000 7 104" Ba Sole an ee ee See K. Schirmacher. Emilewicz, R. See M. Lange Emmerich, Wilhelm .......... GEP.5 ain os Hochst....... XV_ | 760,110. XI ,006,738. Emmerling, Adolf. See A. A | Cees Baeyer. ; Endemann, Hermann ........ AE GEA Pape h Ss ug ert XXII | 277,864. (see W. Pickhardt) aa Benga, Carl )0 i. da enenar bees Ger. Casactiay sek XXIII] (Az)711,953. Hugi, Gadient’ o.oo vcrcnb ves Switz..... |Basle........ VII | 831,844; 836,309; 841,003; 848,354; 848,355; 848,356; 856,687; 856,776; 867,714; 867,715; 872,115; 872,227; 872,280; 876,158; 883,703; 887,609; 888,230; 915,338; 923,959; 954,273; 1,043,682; 1,074,850. XI | 1,199,458. XXIII} (In) 893,468. Tee eR Eee ee ne ee — PATENTEE INDEX 543 —eeeeeeeeeaaayayyyEyeeeeeeeeeeauauauauaoeaoooooeooaoaoaoaoaoeeeey~eaeaeEeeEey————————————E———EeEeEeEeEeEeeEeEeE—e———————————SS PATENT NUMBERS PATENTER omstare | 8910NxR | croup and Jarosiay Frohlich ....)/Switz.....]Basle........ VII XXIII and Fritz Grieshaber ......]/Switz.....|Basle........ XI and A. Grob and F. Straub/Switz..... Basleas cia sas VI XXIII ANG ya WUT RICE alsice «0s 5 Switz..... Baslescas soe XI and Carl Jagerspacher ... |Switz BSasleg cot a 2 VI and Hans Kappeler ....... Switz..... Basles. ssc. VII and Herman Kraft ....... SwitZn oe Basle. s. 5 css VII Epstein, Wilhelm (see E. iOtE NUE GR aaa wiine coins’ Ger... ..0.. and Emil Rosenthal ..... CSOT, cens c] ove eens ooe es XV WOUN GEER a csc cs en exes Geta a teas Hochst....... XVIII UCD ate at Zo e.cid « sielescee ciel ss Gets sone: and Leopold Specht ...... Aus.-Hng..|..cceseseress XXIII Erber, Josef. See B. Homolka. and J. Wagner , Erdmann, Ernst ............ Ger....... Berlin....... II ; XXII and Hugo Erdmann ..... eS Sree Berlin......- XXIV Erlenbach, Arnold ........... Ger....... Berlin......- II XXII and Karl Marx ........, en eee Berlin....... II XXIII Erlenmeyer, Emil ........... etc cers Lee see eeeeeeee XVIII Ernst, Otto (see F. Schmidt) .|Ger....... Hochst....... VI and Gillis Gulbransson ...|Ger....... Hochst......- VI and Heinrich Eichwede eo ee Hochst......- VI and Carl Pretzell ...... SU Ger eas: Hochst....... VI and Karl Schirmacher .. |Ger....... Hochst....... VI and Franz Scholl ......, eT ae Hochst....... a8 Evans, William IL. See H. L Trumbull. Fabrmann, Alvin .....+6.:.+> eT ey ee Badische..... XXIII Fahlberg, Constantin ........ NWN, Y;. List (%) XXIV POT PAC ad CO lineéee cnecs «« « Switz... [cre rcrs eee ae XXIII ag vo WO pend ede a 1S Ep OR ee Ne er eal XXIIT eC Ga aaa ROE ahaa th Peri ee ea XXIII Peuriny enty Co. eee sn kets Uo NR OR TIE vai XXIV Penner, Henry J... 5 dsc cs ces Beg.s..<.. Bac lerratticn Versmann ..{Bng......}°c%e" 2" *s*"** XXII Fette, August. See J. Oppermann. Fiebiger, John H. ............ Notts. aca] sects ee xs XXIII UE ACES Cee ey ee (Oe VI Finch, EO SR ae a ee Dis eh os sete Hercules..... XXII Finklestein, Philip ............ N. Y..... Jecersssccees: XXIII WAOTIG GOED ok ee acct es es> DA. assets [te oes ws XXIII Fischer, Arnold. See R. E. Schmidt. Fischer, Charlies H. .......... Ney... see e ese reeees xx PROM OMe PE) vices ok cs Ge ws e 00.4 Cette. os Boehringer XXIV and Josef von Mering ....|Ger....... Merck......- XXIV Wischer, Eugeti ..:........... Ger....... Hochst....... XVIII XXII and Julius Oppermann ..../Ger....... Kalle... as VII Fischer, Friedrich ............ Ger....... Bayer.......- XVIII and Hugo Guntrum ...... (eeu Ses, Elberfeld XXIV Fischer, Max (see J. Schmidlin) state! ste Geigy....... XXII Pee OE UAC a we Cis vc nae Gere... Hochsti2.:. 2. XVIII XXII XXIV Fischer, Paul (see P. Thomaschewski) ............ ereh ose: Bayer........ III PSC ET te RICH ATG Wis ccs a s's ous aves Gertie pes Paver ina ccscs XXIII Fischer, Robert. See L. Schutze. Fischesser, Alfred .........6.- Geli gases and Joseph Pokorny ...... Getrenwa Fischesser XXIII Pian William (He s.c. eee os PSOE Fadi oat iva vie a sigs ses XXIII 898,452; 994,988; 997,766; 1,081,898. (In) 1,026,574. 1,188,259. 1,221,849. (Az) 1,213,608. 1,227,407. 1,237,183; 1,259,499. 940,586. 899,863; 1,242,536; 899,994. 681,689. 473,453. (An) 633,438. 923,635. 869,073. (£) 658,769. 992,947; 1,105,554. (Ab) 1,144,325. 1,105,501. (Ab) 1,144,181. 310,128. 610,349; 679,221; 714,882; 714,883; 830,312. 858,065. 978,865; 983,486; 1,012,619. 888,981. 667,935. 739,069. (An) 661,858. (f)319,082; (m)343,803. 1,043,582. 1,279,679. (Az) 582,853. (m)615,828; 615,829. 126,277; 130,909. 1,383,092. 1,383,710; 1,383,711. 1,311,158. (Ab) 542,046. (Tr) 171,787. 203,130. (m) 667,388. (m)773,251. 283,766 278,926. 540,427. 325,827; 325,828; 329,636; 329,637. (p) 729,054. 1,338,363; 1,340,603. 248,153; 248,154; 252,202; 252,203. 270,045. (m) 273,498; 938,565; 938,566. (Az) 1,057,137. 1,338,364; 276,796. (Az) 457,488. (In) 175,829. 544 DIGEST OF PATENTS DYE PATENT NUMBERS mide ASSIGNEE GROUP PATENTEE Bisher, CArthtir Wiese «ater o sieisa ie | Path de kee Ws Ce Pe Us Ane XXIIT} (Tr) 1,209,423. Fisher, Mary Me) iitalmie\ehalelareie le,evel'e Mo Me eee Wael SER ate hee atataie BiahibC ae XXIIT 721,290. Flachslaender, Joseph (see K. Po 2Gralert) oles fae erties ate Geri. Bayere neice XV 935,009; 1,113,766. K. P. Gralert and Max Buff ee are Baye? cara a XV 1,081,598; 1,081,599; 1,081,600; 1,081,6013 1,081,602; 1,093,259. Synthetic.... | XV 1,132,022. ek: and | Pal Ge elsiste treet cre's (Zersae eet Synthetic.... VI 1,215,359. Flemming, ) Paul o.oo Geena OR PEAR bone e Ge mr XXIV |} (m) 1,036,087. Flett, Lawrence H. See C. G. Derick and W. M. Ralph. Phek, oy 755) Bmil oc 20. ce sales Gene ca ol te seas saetetion XXIII} (In)671,994. Fodor, Otto. See E. Kopetschni. {RS Spel Forel; “Sylvestre. o. ae sicw:siero are eth ath Ga ole cates eee VI 386,192. Forger, William <.0 7.602 os 35> We Sk aha etl ae Cac eee XXITI1| 776,830. Fourneaux, Emile A. ........ Niet Yaeee Metzger II 739,071. V 726,667. VI_ | 728,388; 728,455. XR (Su) 714,687. Badische..... XXIII) (Az)913,633; 913,634. ERE. dea L decent ee XXIII} (Ab) 1,277,056; Re. 14,824; 1,350,600. Fowler,. Galbert a). ‘fea. ee sects 1D hdr e Hiner, AARP eer XXI | 954,949. Fox, Charles (i; (and Mary 1.3) Calit.. 5, <4. «semen eee XXI | 81,992. Frank, AIDEN clock oli lern eine Gerkg et yl Se ainee ose VI 320,638; 329,639. Bayetoecse ee VI 401,024. Franke, Charles ............. N. Y...<«. |Hoffmann,...| XX oes see Hrankey;Bimil cee as ce sce ks Getcs ar: Griinau...... XXIIT} (An)965,804. Prascht: “Fang -tAe s,s ets Ohio... .: Grasselli..... XXI | 518,980; 518,990; 518,991; 518,992; 519,036; 1,308,060; 1,323,263. Freimann, Hans 4.0... 02.... GOt eee Jager........ VI_ | 1,006,929. Fremery, Max, and Johannes Ushan fo on oe Ger, fe ccee toteamen steenee XXIIT| 650,715. Friedlaender, Albert .......... Exel aioe Horowitz..... XXTV | (m)966,820. Friedlaender, PR ta ete ee GETS cto sours Oehler....... VI 361,404. Kalle ae ccni VII | 819,348; 850,827. and Bernhard Priebs ...... ey AS Oehler....... VI 375,930. Friedmann, Hermann ......... ts pei K Bayer.....+.+ IIL | 1,022,781; 1,023,248; 1,034,895} 1 1034,896; 1,065,440. Hrie¢e, Jon @Wa cvoe ee pi Fa, Greiner ew hice Oa XXIII (In) 807, 453; 1,341,637. ; XXI | 1,266,577. 7 Fritzsche, Hermann .......... Switz: 0. | DaBlGn a wcccee VI 1,316,781; 1,325,841 (see E. Anderwert) 1,362,936. Frohlich, Jaroslav. See G. Engi. Frohneberg, Wilhelm. See R. Herz. Fuchs, Frederich 40.5.4 3... 2% AFOES «he's ..|Hochst....... | XXII | 641,100. and Hermann Gussmann ..|Ger....... Hochstafa....3 XV_ | 626,807. Fuller, James Wo Minn, 625. svete ee coeee] KX | 553,556. Funckeg\\ Fritz) 20 ae Switzeee Basleun.ss aca XVIII | 887,620. and Carl Jagenspacher ....|Switz.....|Basle........ VI 1,237,192} 1,237,193. Funk!) Casimir coc. ees NGS racae and Louis Freedman ...... ING INV cis ters Metz corre XXIV | (m)1,472,208. : Fussenegger, Ernst .......... GEt seo nre Badische..... VI _ | 806,077; 1,034,898; 5 (see V. Villiger and P. : 1,076,756. 7 Julius) F Fussganger, Victor’ ..asse.0s6 Géti Acne | ROCKEt eins IX | 932,266; 955,080. F II _| 796,715. XVIII 816,457. Gabler, Max. See G. Wichmann. Gams, Alphons . wee eeeceeeees Swit?.. .-a.1 Haslet apes oe XXIV | (m) 1,336,052. aud Otto “Kaiserv, 57... ... VI | 903,284. Grieshaber, Fritz. See G. Engi. i Griess;John tee one ans e Macias sere Badische..... vi 213,563; 213,564. Grimmer, Joseph ............. Switz and. Fritz: Straub: $24.3 <.% ¢ Switz. os.) ) Besle.ccs anes VI 1,402,350. Griswold, Robert G. .......... Mass....-- and Wilhiam: T. «Denovan '.j Mags.....slaseaseacas cs XX | 824,294. Grob, Armin (see G. Engi) ....|Switz Baslesca: sca VI 1,394,823. VII_| 891,690; 904,867; 915,346. anid ‘Carleton: C.c Agama ctN, Jiccs sails ws acer 6s axe XXIII} 1,422,564. and Jakob Wiirgler ...... Switz Baslez aces. III 1,317,160. XI | 1,268,455. Grob, Walter. See B. C. Stuer. | Groff, Charles R. ...........- Minn..... Laundry Blue | XX_ | 826,567. Grossmann, Eugen ............ Switz Geigyy. soe XXIII} (Az) 657,767. Grousseau, Edouard de. See|Fr........ de Grousseau Edouard. Grubman, Benj. See N. Goodman Grin, Gottfried is. seas eons Gers cole Bayersc yas XXIII} (ATI) 396,692. Griinbanm, Max? i. ieee oe Bw itZixivn.c Basle... jccvet XXIII} (Su)o901,705. Griinhagen, Heinrich ........ Geran’ Berlintecwses I 1,255,739; 1,255,740.) 1,473,550. Chem. Found I 1,455,486; 1,455,487; 1,455,488. Griinhut, Jacques .........0.- PNG ey cathe te Re nari XXIII} (Ab) 391,315. Griittefein, Wilhelm .......... Gers. cass Synthetic.... | XXIV | (m)1,305,462. U. S. Govt... | XXIV | (m) 1,338,297. Gtinther, Alfred. See A. Thauss. Gunther, Fritz C. (see P. J Whigs) Ounce ceca see ee Geriitss ss Badische..... VI_ | 798,008. XVIII | 1,430,899. XXIV | (m) 1,412,937. Ginther, Oscar (see I. Hesse andi K. Desamatri) 22....%.. Olver ce si Bayeracetes VI 839,382; 1,019,321; 1,009,740; 1,009,741; 1,074,429. Synthetic.... | wy | 1,150,675; 1,159,375. and Leopold Hesse ...... SEP. aga a4 | DOVER eee VI_ | 877,643; 877,644; 897,529; 898,217; 921,105; Re.13,121; 921,230; Re. 13,422; 935,010; 935,017; 935,018; 945,780; 989,000. and Arthur Zart .c.cus ess. ECS Ny Synthetic.... VI | 1,101,739. and | la eilesse bre eee ae Gerinries. Bavyerooe cece VI 978,580; 982,952; 982,953; . 982,954; 982,955; 989,001. Gtrke, Johannes H. O. ........ Werte Hichst!....-4 VI 249,926. : ‘ XXIII | (An) 261,600. Shia dtr eee: ee Rieia al anel GARE ede Ad cue setae XXIV | (m) 1,417,167. an FNSCHELUG EA. ete witz Hotmats cosas m) 1,308,413; 1,308,414. aera! Gillis (see O. A ae et TUSt) iS siete eae ee ea ee Getiox ness Hochstein. ,109. Guntrum, Hugo. See F we gee Fischer. Gussmann, Hermann (see F. Pachse32 io 2 3o eae pees Getic es: Hochst....... XV_ | 657,768; 657,769; 660,770; r 671,908. 1,000. | Gutzkow, Hermann (see J. xe Brosinery Wy case ae eae oes Lis Metin Hochst.<....« VI_ | 613,920. 4 and Benno Homolka, ..... CPOT SS esse Hochst...2 6.3 XVIII | 661,800. 663,225. Haagen, Albertaynsccesenies Geriati chs esos eee ere 693,703. Haager, Ernst. See C. Ris. Haas, Ferdinand. See H. Geldermann. Hadas; LouistaAok cris cuacseas Geren ue Badische..... XV | 718,342; 931,598. : Cassella...... XV | 919,572. SoccVArm secs XV_ | 1,329,898. XXII | 1,423,494. Hagemann; Karl cd.aneceene Cis Oppo Synthetic.... VI 1,114,750; 1,127,234} 1,270,290. and OStanwe tans ool Ger ientins Baverovann os VI 843,808. PATENTEE INDEX PATENTEE Saher ASSIGNEE Hagenbach, Hans ............. Switz..... |Geigy........ Hagenbach, John ............. OWikt..\c'. 5 Geigy /¢....+% Hagenbach, Rudolf. See W. Dollfus and G. Kranzlein. REAM TACO 5.55 «Chesney euros INESIY «cies crareto eter atel cc oreloretenatats Hahnenkamm, Wilhelm ...... Gerkoce. ce Hochst....... Hlatlers michara OF Ps 2c... 1Ger.... sss Badische..... Haller, Herbert L. See E. Q. Adams and R. R. Williams. Halvorsen, Birger F. ......... Norway anpowcr es HOorpyeee.. 6cn ca NOT WAY scab oes cece eeere Hamburger, Alexander ........ 1S eee pee Bayer... oe Hamlin, Marston L. ...... tow it, CO Sains Amer. Syn... Hankel, Martin ©... ..ccesces- Get a. Griesheim.... ee CLE a oras wie wh he <1 AUS... uso] aciesstaicnooes Hansmann, Otto. See W. Herzberg. Harger. Rolla No sce ses sess D.C U. S. Govt Biariey, James (ciacecccnccees INE ASS yet ie| arere sie sisteters sie Harrsch, Eberhard .......... IN CEN A ea lictes crete skate BTOLE ADE Is bine sca ees os Beng. 6 le beck ss oe e's ES DF | A nein Ora eae i 31 ae Stewart...... BEALE FOUTS Da, staciecsiumes vee es Wl ag5.0 Sena bese se keane es Hartman, William W. See H. T. Clarke. Hartmann, Christoph ......... Meg nn FIGGHSI 7. oy 3 ‘ (see J. Herbabny and E. Hepp) Hartmann, Max, and Max 5 SEIDELEN Gi asicietet ders toe scctvcwiee . | Switz Basle........ and Hans Kagi ........- Witz sa... Basle:....... and Ernst Wybert ........ Switz Baslevew oo ns Hassencamp, Ernst .2........ A) ean Dickerson Hassencamp, Hugo (see R. COU Gees ter chinks aie. fed sco a e.5 0 6 Gere Bayet.....:. Elberfeld.... HMaugwite.. Rudolf ......4. 605, Gereene. Bérlitizs so... Hauptmann, Peter ......... Ger....... Bayer. ste Synthetic and Albert Rohde ....... Berek 3 « Synthetic Hausdorfer, Arthur .......... Gere ton. Elberfeld.... and Carl Heidenreich ....|Ger....... Baget ess... and Friedrich Reingruber .|Ger....... Elberfeld.... Haussmann, Emil (see R. PAPI ee inate es % wks 4 Sap e s 5 wie Berlin....... Piawierek, Josef Po. .c nesses EG oats 's Sal a git ean se hs ae Haworth, Walter N; ......... BCotien< ss and Frederick W. Atack ..|Eng...... [...-.-eeeeees Heidelberger, Michael. See W. A. Jacobs. Heidenreich, Carl (see M. Kahn, M. Ulrich, A, Hausdorfer OE a a eT ng Ger......- Bayer........ Synthetic..... Bayerins srs and Eduard Martz ........ Co eee Bayeryoy i ae. Heim, Friedrich. See A. Stock. Heimann, Heinrich .......... C05 ene Berlin....... (see W. Werfberg and W. Herzberg) WAG LP au VitCk .as sees ss Ee Po hy Berlin sss Heitz, Charles. See A. Dachert. 547 DYE GROUP PATENT NUMBERS XIX | 1,194,380. YI | 790,363; 790,364. XII | 808,919. XXIII 404,193. XV_ | 1,083,489. XV_ | 690,271. XV 1,310,751. III | 1,059,607. DIVG 171, L1S, foo. 1,015,159. XXII | 1,309,683. XXIII} (Az) 1,200,726. XXII | 1,384,615. XXIV | (p)1,297,685. XXIII] 170,626. XX _ | 88,291; 90,359. XXI | 1,362,879. XXI_ | 1,399,014. XXIII] 429,131. TII | 704,798. XXIV } (m) 1,403,117. XXIV | (m) 1,437,802. XXIV | (m)1,350,408. VI 981,132; 381,471. XVIII | 331,964; 331,965; 498,471; 501,069. XVIII | 611,628. VI | 999,558; 1,209,154; 1,405,687; 1,419,500. 958,640. VI_ ! 1,073,754; 1,074,946. VI 1,199,890. VI 1,113,622. XVIII! 676,555. VI 980,251; 980,521; 1,021,364; 1,021,365; 1,021,366. XVIIT] 999,028; 1,026,089. XVIII | 647,260. XXIII} 661,985; (Su) 665,737; 953,008. XXII | 690,724. XXIII | 1,426,380. VI | 891,931; 944,328; 1,009,745; 1,025,267; 1,474,587. VI 1,183,378. XXII | 902,150. XI | 895,635. V 872,815. XV_ | 1,096,715; 1,098,259; 1,098,260; 1,105,515; 1,199,697; 1,251,368; 1,251,369. XV 1,099,039. 548 DIGEST OF PATENTS PATENTEE papi ASSIGNEE saat ahs PATENT NUMBERS ak ON ART: Snes ee CET lan cre Cordessts. cus XXII | 722,506; 722,507. ee eas XXIV | (m)671,135; 709,321. Helmert, Bruno. See I Rosenberg. Hencki, Mu Vintners toreanvacuntcra borers (Erne Badische..... III 443,402. Henke, Clyde O. See O. W. Brown. Henle») Brang ote cue Saleen s Gere nes Hochsta eeu III | 980,602. forrest Naa: See E. Michaelis. Henry; Charleston 1 ya. ee ceee ET Fe ee Gleaner ntteeatanectes XXIII | 835,754. Hensmann, Otto. See W. Herzberg. Hensmer, Karl. See A. Blank. and W. Neelmeier. Hentschel, Willibald .......... Geraee nes von Heyden..| VII | 712,190; 737,836. Hepp BE duardies iy ate eee se Getic ee QOehlencn Seats V 466,826; 466,852. XVI | 270,311. HOCHSE ae eects Til 711,310; 713,432. and Chrisoph Hartmann ..|Ger....... Hochst... ss2.). III 734,866; 748,375; 975,863. and Rudolf Uhlenhuth ....|Ger....... HGchstis ¢..55 III | 778,036. and Rudolf and _ “Fritz Reemiertie a 2s CEeRe aes Ero Genes ELOGHSE Sus «ote eg III | 1,052,480. and Ernst Wolpert ....... Gris. Hochst... .2: III | 754,768. Hepp, cnichard oct aes ee Gare. Oehlet i... s.: XVI 1 -270,31% Herbabny, Julius (see C. H. : Rudolph) Capea Sapa Giae EC. ea as Ochlet i.e. «2 VI_ | 639,042; 644,201; 644,202; 666,866; 666,867; 670,308; 666,866; 666,867; 670,308. XII | 627,600. and Christoph Hartmann ..|Ger.......]..scccessees VI 639,040; 639,041. Hermann, Willy. See M. Mugdan. blerimarne, (eo). . te ae eer iaaee Elberfeld.... | VI | 673,079. Herz, Richard (see A. Weinberg and I. Levinstein) Ef BAS Cassellas.s +. IIT | 1,103,004. VI 1,107,164. XV 709,151; 723,154; 742,189; 956,348; 966,092. Sek Meee ete VII | 1,243,170; 1,243,171. ands Hs Balhorne eee CAPT are Casscella esc XV 1,452,805. and Wilhelm Frohneberg ..|Ger....... Cassella...... XV_ | 1,100,877. end W.saul Gas eee Gee rivaies 5 Cassella...... XV_ | 960,919. Herzberg,s Martin <1 Geeseces GES; ot aes Davers.s) ses VI_ | 384,315; 384,316. (see A. Blank, F. Runkel and M. Ulrich) Elberteld: o.. VI 792,032; 792,033; 792,034; 79757313 7975732. Synthetic..... VI 1,126,466; 1,160,406. and Friedrich Runkel ....|Ger....... Bayer........ VI_ | 953,033; 953,034; 953,035. Herzherg, Withelar). ) 0.2... 5. GET. 5 ss sie Berlin..:.4% sas VI_ | 800,914; 842,548; 987,362. (see O. Scharfenburg) : XXII | 536,524. and Walter Brnuck........|/Ger......-. Berliny i: a6 III | 993,992; 1,008,906; s 1,008,908; 1,050,829. - ; XV_ | 996,485. and Otto Hansmann ...... Strasse Berlin....... VI_ | 583,439; 657,064; 657,065. and Heinrich Heimann ....|Ger....... Berlin....... V 567,473. and Gerhard Hoppe ...... Ger oes Berlinsi hou) III | 1,078,505; 1,131,516; 1,419,502; 1,431,656. and Werner Lange ...... (er. toe Berlin. .4 a: VI | 997,061; 1,078,503; 1,078,504. and Heinrich Oster ....... Gertrerines Berlin ees. VI 906,422. andes a Ronis meses Gerise secs Berline eee. vi 954,960; 955,068. and Franz Schwabe ...... Ger Se eee. Berlins. avieres VI 1,008,907. PATENTEE INDEX 549 PATENTEE pate ASSIGNEE panes PATENT NUMBERS and Oswald Scharfenberg .|Ger....... Benlinges. VI |986,287; 1,038,884; 1,408,296; 1,408,207; 1,419,501; 1,426,189; 1,426,190; 1,431,655. Ven |e tO2.0 71 te 200, 8 SOs XVIII |647,834; 835,682; 866,350. and Max Ronus ........ Geri sta Berlin Shane ote XV_ |864,644. muna Otte Siebert ~.....:... Ger... .. i Berlin.\... << VI 704,825; 704,826; 770,430; 03,592. and Oscar Spengler ...... Ceti se es Berlin....... VI |865,587; 906,421. Brews GuUatG. LHON s s.de. 6 « Genres os Berlin. .... 6. XXIL | 800,913. ANd Oscars WeDer «6.4.0.0 5 Caneraece Begin earecy ee VI |541,750. i XVI |522,897; 539,738. SECA PEIOIO ove cic a s« ey ae Com. Res.... | XXIV |(m) 1,321,307. Higburg, William. See I. H. Derby. Pligwing, James) ...06scescsces Bees: i soaree ek os <0 II {138,155. Pivipert, ssieviried . isc. csass- ope Vnitr Sy 5 XXIV | (pl) 1,427,386. Hingberg, OSC@r ¢isasescsccas Switz..... |Hochst....... XXIV |(m)560,416; 1,432,291. PUITGCH CRODESt 2545 cca ev ccc es« eres i: St. Denis.... V_ 1|536,626. Hochstetter, Robert .......... GO) GIOM ee a aces orete slates VI_{1,052,145. PIGe I OTT es oe dave os eee, Cee Elberfeld..... XXIV | (m) 607,172. Hoeckel, Siegfried. See P. Julius. PIGUET, BIUWAIG, os cS scenes Gees hones geeh ahiate XXIII | (Su) 647,493. Hoerlein, Heinrich ........... Copeie: Bayer sess. + 6s VI |965,882. Hoerlin, Julius (see O. Rein- BERT ME oe ahs « (Cer ee ae Weiler....... XV_ |796,514. Hoffa, Erwin (see H. Wagner).|Ger....... Hochst... i-/07- VI | 1,197,633. VII |1,025,138. XIII | 1,197,632. Hoffmann, Augustus W. ...... Meet. | evenvhate nce as XVIII | 43,066. Hotlmann, Carl .... os 5.<. Boole k sies.| va Oa Rete eee Read-Holliday and Robert Holliday ...... BUsigen es wom Us es eters aiaienecs er Holmes, Fletcher B. .......... 1 MOR Mie ee du Pont..... Hrojste; Aveore i aa)d ayes ee sia e ok Geraci ei. Bayets soos as Holt, Henry S. A. (see D. Vorlander and R. Knietsch).|Ger....... Badische..... and Karl Reinking ........ Gers,.c2s Badische..... and Gerhard Steimmig ....|Ger....... Badische..... Homolka, Benno (see H. Gutz- kow) Gers i gas Hochst. vem. and Josef Erber iss cscs c Gert eas Hochst.\<6..6 and Friedrich Hiibner ..... Gerd ss 5st Hoechst? ventas and Friedrich von Bolzano|Ger....... Hochst. ccc and Otto Liebknecht ...... ET ee iste Hochst. ...%.. and Nicolaus Schwan ..... Ger... ses... Hoéchst..i.5 <5 os and August Stock ........ Gerinantr Hochst....... and Robert Welde ........ GEC He cieter ate Hochst. cece Hoppe, Gerhard. See W. Herz- erg. Houghton, Alexis C. ......... N.Y. Semet-Solvay Houlehan, Arthur E. ........ Delus.cenk du. Pont..... Howald, Arthur M. See A. Low Hiibner, Friedrich. See B. Homolka. Hat, Withert 11. cee peek Pace hits Koppers...... Huffman, Charles .$o)... 2240. TH Aare ee Sunbeam..... Huguenin, Daniel EF. ......... Switz....- Durand:..... Huismann Johann: . ose seen Pra ee, F Synthetic..... Hund Walter) areas eae. Calitics Ua eee rete Hutziers;Rudolfi soceens ces. ers Sos Badische..... Ijinsky, Michael i...ess deus Gernot Poe eae Wedekind... Imbert, (Georges) va. csseedewere COT os taracltatehe cata ehereees ete DIGEST OF PATENTS PATENT NUMBERS 1,297,170. 250,247. (Tr) 51,404. (Az) 439,953. 355,934. 362,835: 386,247. (Az) 252,317; 271,636; 355,933; 355,935. (Az) 241,661; 254,550. (e) 1,309,577. 1,012,853}; 1,059,670. 643,502; 661,871; 713,437; 715,074; 1,042,679. 661,872. (In) 820,869. (In) 826,428. (pl) 1,294,662. 1,209,163. 458,281. 649,727; 649,728. 669,794; 675,217; 726,688; 894,004; 894,005; 894,006; 898,738. 844,804. 471,638. 575,237- (AI) 418,916; (In) 702,730. 763,756. 871,507. 839,590. 675,217. ; 712,798; 768,455. 704,804; 714,000. (p) 767,815. 622,854; 636,043; 636,094; 640,564; 648,261. 894,004; 894,005; 894,006; 943,678; 1,025,174. 893,499. 1,308,757. (m) 821,291. 1,308,356; 1,334,033; 1,337,317; 1,392,042; 1,477,058. 1,416,205; 1,416,206. 1,274,046; 1,274,049; 1,283,519; 1,413,026; (Az) 1,274,047; 1,274,048; 1,315,961. (In) 411,149. 1,159,386. 1,365,407. (In) 780,886; 1,188,543. 1,133,031; 778,670; 851,423. 826,509; 826,510; 847,078; 996,487; 1,087,293. 1,261,394. (An) 1,199,273; (In) 1,175,634. 894,149. 894,148. : j PATENTEE INDEX 551 COUNTRY Beamer merer, Garlic... ess Te Badische..... VI_ | 863,396; 914,144. (see P. Julius, L. Blangey XXIII | 833,602; 1,232,551; and R. Bohn) 1,232,552. Az 058; 872,181. Iserloth, Carl F. See G. A. Led apoio Si” 87 Waldinger. elervt ax 0ET. d.crcrs wikietele, «sha «6s (see O. Bally, “C. Miiller J and R. Scholl) Géticc. «+s LDadisene.s.<. III | 617,686; 619,574; 621,679; 650,756; 688,645; 690,292; 715,622; 738,614; 798,104; 814,137; 831,002; 837,840; 855,248; 860,480; 876,190; 893,508; 909,800; 922,282; 929,442; 1,001,408; 1,004,433; 1,026,588; 1,032,215; 1,032,216; 1,047,812; 1,047,813; 1,057,243; 1,062,975. III | 1,089,221; 1,090,621; 1,126,475; 1,169,404; I,201,968; 1,207,762. ys XXII | 619,181; 828,741; 893,507. Bie Prt) eet cals ce es | GET... es Badische.....} III | 863,397. and Hugo Wolff ....... Geto ete + Badische..... Iit 929,443; 961,612. Arthur Luttringhaus and Heinrich von Dies- on) Cs 2 A eee Eee aa ete Badische.....] III | 941,320. Israel, Adolf (see A. Blank, K. Krekeler and P. Ott) ...... and Oscar Dressel ........ Geri. coe Elberfeld.....} VI 731,460. and Richard Kothe ...... Cette ss << -|Elberfeld..... VI | 614,301; 648,623; 658,807; 662,122; 663,498; 675,620; 675,632; 677,516; 677,517; 748,076. XXII | 653,678; 656,646; 675,627; Ah eay 675,630; 675,631; 77,514; 677,515. and Karl Bathe A ee Ger... Bayer...... VI __| 515,3395 543,539. Iversen, -[..-0. attare ifnte a's ws NV IRS a wanes De tate Sale yatarw Som ec XXIII | 83,502. Jackson, James ....... re ES | Oe ae eae vee eceeeecees XX | 155,230. hae MOUS ge oe ee ees sls, 9 N. Y..... |Dissosway....| XXII | 1,446,564. acobi, Andreas (see R. E. oT at ht hel ee APES ee e's Pavericcss ss -| IIL | 1,038,580. Jacobs, Armand M. See Miil- ler-Jacobs. Jacobs, Walter A., W. H. Brown, M. Heidelberger and IPL GRERO sod ocic eo) chases cas N. Y..... |Rockefeller...| XXIV | (m)1,315,127. TACONSON SEM) cec.c1es «es = bP poe WE eae tae oe teee pp WLLL 1257,7373) 1 200,585. Jacobson, Paul and H. Tigges haw fin en's Cassella......| XXIV | (p)604,049. ORE Ie RUREAE Od) cies cie'es nese ee Crete ss Elberfeld..... XXIII} (Su) 717,749. Naéckel, Berard ..cc.s aves: Gere: Bayer. c cer. XV_ | 898,916. (see A. Herre) Synthetic..... XV 1,140,745. Jaesschin, Hugo. See O. Kalt- wasser. Fagerepacher, Carl 2... ccc ceces Sit Z . Ge | ASO eleieie's VI 916,161; 1,210,808; (see G. Engi, F. Funcke 1,216,813; 1,323,285; and B. Wuth) 1,375,701; 1,382,196; 1,437,758. Hadi Was LESICT “ens vices sss Switz Baslecrs ones ier VI 1,338,506. and Thilo Kroeber ........ Switz Basle. Ge ws VI | 750,284; 797,441; Re. 12,557. Jahrmarkt, Friedrich M. See P. Julius. Jamieson, David <.-.5<.-..0065 0) CER pe ieanes) re wre niges viens) | eels | Cin yaoss saa: Jansen, Johannes (see A. ime VAe Pe ho we ei eed oe. Getrag sss and Wilhelm Neelmeir ....|Ger....... Bayer........ VI_ | 924,231; 924,232; 933,841; 933,842; 936,321; 961,354; 961,355; 981,276. Janssen, Hermann ge ef.......|Bayer.....---| XXIV | (m) 492,868 arosson eon an uller- : Pack Bue +e 2 aes Wyate. u e Brown....... | XXIII} (Ab) 134,066. Jeanmaire, Paul and Rene Bohn/Ger....... Badische..... XXIII! (An)772,237. Jedlicka, Karl (see J. Schmid) |Switz..... Bacletia.cy as I 666,095; 666,006; 730,771. VI | 585,104; 759,613. and Arnold Schedler ...... Switzucise Daslen naa eu VI 763,761; 889,016. 552 DIGEST OF PATENTS —————aaaaaaoooooooomm=QeeeaeeSaaSaS==_—__u_ec_x_—c_—c——S——aSeaSsaSsSsS=__3__je__‘uu¥>7—_=>7>x3>xzu>—sSsSsoSoaSs“scssoso(u0W—SOOOOqOoOSoSoS COUNTRY DYE PATENTEE OR STATE ASSIGNEE GROUP PATENT NUMBERS Tohansen, Ernest) Moe... 2s, Eidsraierele ele Atlan tics ss tawt. XXII | 1,477,820. Johlin, Jacob Me Ve heains ch ose N 2a Yo Semet-Solvay. | XXIV | (f)1,372,434. Tob a aanSa ts. se ies oc ols iar RIS PRE SC ip Bee WM XXIV | (pl) 1,355,834. Jones, Whitney Bo .% sca en vat cae Butterworth VI 1,310,532. XXIT | 1,394,556. Jordan, (Heinrich? ss. ne4 see Gerrans. Bayer........ VI 999,797- (see W. Neelmeier) Grasselli..... VI 1,422,866. and Wilhelm Neelmeier ...|Ger....... BYEL Seki es VI_ | 916,323; 920,151; 993,073; 1,000,269; 1,010,433} 1,024,080; 1,024,081; 1,032,412; 1,097,231; 1,098,388; 1,114,771; 1,127;2613,) 16547,609. Jorg, Paul. See R. Maag. Joyce, A. Willard) .i.cn dares N. J....- Chem. Found.| VI | 1,472,333; 1,472,334. Julius; pePaulsa(see.. tH. ZA; y Bemnthsoen yey. ies Crkeuitvoeee Ger......- Badische..... Vv 609,352. VI | 447,189; 524,251; 524,252; 524,253; 524,254; 525,656; 525,657; 628,814; 644,233; 644,234; 644,235; 644,236; 644,237; 644,238; 644,239; 650,7573 654,064; 654,065; 656,120; 677,227; 677,228; 677,229; 677,230; 677,231; 688,647; 690,294; 710,059; Seppe 718,356; 752,562; 33,605. XII | 670,172. XV 648.7535 6481754; 648,755; ,646. XVIIT| 886,815. ; XXII 785,003. and Louis Blangey ....-. Ger ee ccvees Badische cceee VI 932,289. and Georges E. Darier ....] Switz Badische..... XIX | 637,340. and Ernst Fusenegger ....|Gef....... Badische..... vi 754,315; 786,767; 787,767; 787,768; 789,096; 792,421; 879,053; 914,146; 921,546; 935,371; 1,188,545. TX | 955,080. XII | 935,370; 1,010,910. and Siegfried Haeckel ....|Ger...... Badische..... VI | 750,716; 765,581. and Carl Immerheiser ... |Ger....... Badische..... VI 1,073,902; 1,073,903; 1,073,904; 1,073,905. and Richara) Waiblet es. COURT A®, Badische osSee XXIII | (Az)634,824. and Fritz Gunther ....... eS ae ese Badische..... VI 692,676; 695,811. XXII | 713,447. and Friedrich M. Jahrmarkt}Ger....... Badische..... VI 695,812. and Eduard) Munch)... > ier ots. be Badische..... XVaulo20,60 5 and Franz Osthelder ...... ee sates Badische..... VI 765,080. and Walter Reess ....... Ger......- Badische..... I 644,324. Hans Reindel and F. C. . Gintherors -oomie tee Ger....... Beduehosen VI | 770,177. and Pek euboldgem aan Ger....... Badische..... XV_ | 650,326; 650,327; 735,775 and Akim Tkatsch ......- Ger...... Badische. 1. cee 619,577. VI_ | 692,675. ve Si sok and P. Nawia- : PrP at Nea pif oe S een : weoee | WIL | 955,410; 957,683; oad ron \Winters we eck Gercoryeaes aa pane: eat VI 765,079. Junius, Gustav E4i oi gee Gefitnaise Sanderson....|. &V oor Justmbredrichwy. yc acters Ger.2. ass THochste eee XXIII | (Az) 647,268. Just, Richard and Fritz Eck- hard cc eiccsees Ga em oe ee Gericcis xis Badische..... XXIII (An) 1,150,863. and Huge Wolff...26. 2s. Ger. as awe Badische..... III | 1,003,268 Racer, Filip. 3904 0. cheese a Gefoaes ens Badische..... TIT | 863,401; 925,017; 931,618; (see M. Isler and H. 932,290; 1,095,731; Wolff) 1,459,536. XXIIL| (An)970,340. Kage, Hans See M. Hart mann. Kahl sbeopold asc. Getraseee « Rutgers...... VI (m) 1,028,074. Kahn, Myrtil (see R. Lauch and Ov Deesseys ine eee ee Get on cee Elberfeld..... VI_ | 425,885; 602,540; 603,008; 722,715; 722,716; 725,847; 725,848; 726,695; 727,962; 727,963; 727,964; 727,965; 727,966; 727,967; 729,601. PATENTEE INDEX 553 COUNTRY DYE PATENTEE Su eCATR ASSIGNEE | croup Bayerivaceiciw ste VI and Karl Heidenreich Geri sess. Elberfeld..... VI and ekRichard Kothe .....- Get. Sooke: Bayertcsewsoe VI and Anton Ossenbeck =| KOC aE ericr Baviertecsuren Synthetic..... XXII Baverwoncties« XXIII and Friedrich Runkel Getecs pws Bayer’. cee VI Elberfeld..... VI Kaiser, Otto. See A. Gans. : Kalbe at witiecce tetellee siecs cis + etan caren Badische..... VII Kalischer, Georg (see F. Klinge- mann and M. Hoffmann) ... |Ger....... Cassélla cn... % ae Se te eas VI XV XXII MIG Ph ISSET wi. dws o's se» trefins acne Cassellacutsjess XV and Nee A oo a aa Gens ss 6 Cassella ui. XV Kalkow, Fritz. See J. Abel. Kallab, Ferdinand V. ......... Serv aes Oehler....... XXIII Kaltwasser, Oskar (see B. : XV Or ae Ger....... Berlin....... XV and Max Gaumer ........ Geri ee cc os Berlin PAIR VI and Hugo Jaesschin ...... Getic sisie ae Berita ses and Hans Oechrn .2.....;.. (ETE SoS aise Berlintss.as II mamma Oliverta.s ee. ce ae fe. ws XXIV and Ernest H. Volweiler .. |Ill.......- Abbott....... XX and Roger Adams ...... Ill........ Abbott.---. *. IV Se Michael. See F. ender. Kate, Tehn L223 - VI |602,637; 602,638; 602,639; 602,640; 602,641; 626,913. 2 XIII 805,143. and Franz Scholl ........ Génictascs Hochst... 0s. XXII | 618,688. Konig, Karl .....--+seeeeeeeee GETS oad bie Hochet. |i... VI |878,964. Konig, Walter o.0205..c0ccceee (Sais caews Bayer cess ys VI_ |874,067; 874,968; 809,177. XIX 913,5135 91315143 947,918; APs : 906. Konig, Wilhelm ...........06. Gef.....0% Merernc tT ccs: vI me Spry RE a LT Se a, Ceamin nS hus a eves SAS? vi 042,916. Keonitzer, ‘Prank tevce Fs chess on oh Gari tis 5 al ae there eeree XXIII | (Ab)830,082. Koerner, Georg: 25. os ¢ eee ccm Ger, tases Badische..... VI |420,350; 638,127. Koetschet, Joseph ............ Besidusbins Soc. Chim VII = |662,073; 662,074; 662,075; 662,076. ‘ XVIII Aa baie XXII 07,050; 709,159. XXIV | (£)648,568; 692,863. and Andre Barbier ..... Beye Wee Soc. Chim....]| VII [1,015,495. and Maurice Beudet ...... Bet wpe Soc. Chim.... | XXII |1,298,356; 1,306,963. Roetsie! “Arthurs: .ssccosee aus N. Y..... |Rohm, Haas..| XXIV |(t)1,344,950; 1,344,051; 1,344,952. Kohlhass, Jakob. See H. Wag- ner. Kohres, Georg. See R. Gartner. Kolbe, Carl. See R. Schmitt. Kolmer, John A. See J. F. Schamberg. Kopetschni, Eduard .......... Get. das es Ladislaus Karczag and Otto Fodor ..... Gert Karczag.. oc. XXI Koreff, Richard ........+-..-- Aus.-Hng.. z ea apd: Kinzlberger... 850. Korndorfer, Georg ......-e000+ Ger ovaa. archi AXIL | 544,860) (see F. Stolz) and Baptist Reuter ....... Geran Hochst.cc.... Kothe, Richard (see P. Ott, A. ney SOT oa a Israel, O. Dressel, B. Hey- mann and M. Kahn) : and Oscar Dressel ....... CT...- eee Synthetic..... Vv and Heinrich Hoerlein ..|Ger....... Bayets sosex os ue pre and Anton Ossenbeck ..... Ger. ides Elberfeld..... VI 8. vie Friedrich Reingruber ..... Geri. Soe. 43175 and Hugo Hassenkamp /|Ger....... Raver ciuks was Moritz Ulrich A AVAL ete ie and Oscar Dressel ..... Gerson. Bayer VI +) sich Heptsitcn |S TRIS PASTAS Ts ee) SRL PW aS a eR A MIO AG Gc 511,532. Kranzlein, Georg .........+++- Ger.oits xs Héchsts awn. x (see A. Schmidt) mbes and Martin Corell ........ Gerais oe an HSchst: ve XXIV |(m)1,422,860. Rudolf Hagenbach and Franz Gilroy ...... Gere s'ke as Hochst e's ns:2 XI 1,138,670. j : ; % f PATENTEE INDEX 555 PATENTEE eared ASSIGNEE erat MELOrinan tl lsscalcic's sba'e's > Switz Baslevetaer vats (see G. Engi) Krais, Paul. See K. Krekeler. Kramer, Erwin and Ludwig Zeh|Ger....... Bayerwentusie ca Rrdaee, (Norman VWiaiisec. ss... PML Vet shasin cee mens Pisa aes @ oa Petes tri thie) sg cis si/eie ciele\e.e 6.0 Switzecd se Basles tees. cis INA Yel hion Cassellas cues Krecke, Friedrich (see I. Rosen-|Ger....... Krallee trons are berg) and Ignaz Rosenberg ..... EP e ne os 5 Woatle rs Pecke a's and August Blank ........ oe Seas Elberfeld..... and Adolph Israel ........ ae aes Biberfeld...... and Eduard Martz ....... erie cs. « Elberfeld..... BNMOPOUL RTUlSece sess... oS eee Bayer eva. <.93 Adolf Israel and August Blank ... ([Ger....... Elberfeld..... Ey Diartz and A: Israel .,|Ger....... Elberfeld..... IREpeber se LuilO: Geis cides. ce a0 © Switz SH Basle dees clea Gs K. Jagerspacher and P. tt Krohn, Carl. See M. Hoff. mann. Kronholz, Erich. See A. Schmidt. Krenlein, Gustav. See Ve. 22) | National=-.6. VI 1,365,040; 1,372,439. and Theresa M. Siisemihl .]N. Y..... |National..... VI 1,363,886. Lederer, Leonhard .......... Oee to ahs wit ttoneee XXTIT | 654,988. XXIV | (m) 543,579. Boehringer... | XXIV | (™)503,748. Legg, David A. (see C. Weiz. MANNF eels ctor arch Moe ee Bngsieae Adam.......-| XXIT | 1:447,557- Lehmann, Fritz. ...2550 aes Gertete: Bayers eter cet Xv_ | 866,939. Legh ul ewiste ek usher ae Wage t’. 3). bs venta oe eee XXIIT| 186,485. Leloit, J wlesil wie cece ace Bogiscs cs Posseltic... XXTIT| (Ab) 248,934. Lendle,\ August ).4 soso eae N. Y..... |Pickhardt.... | XXIII] 1,375,919; 1,378,418. Leonhardt, ’ . and Ernest E. Naef ...... Bg 6% ara XV a ie ag and Hermann Pfeiffer ..../Eng...... Levingthine. © VI 625,174. ROW PROP EE ec iais osteo ee ss ERE. os National...-- | XXII | 1,420,198; 1,429,514. ieee Sees ae GIpbay.. ... Es nce es U. S. Govt... | XXIT | 1,288,431; 1,293,610. z PAM cd sha aioee » ee etlentyes |. |Eat °° |Gas Coke.r..| %V | xa6s.ss Leykauf, Anton .............. Wpvariacs. | see eyes is XX_ | 87,270. Lichtenhahn, ii Gratien mere Wonzava. aca XXIT 1,311 824. mee era, Latwittiss...3-. Ana eling.ci toe ete aes xin: ete (Su) 960,975. Ser eee ce viel de cs ss ses |NOrway...|ecscseeceescd Liebermann, Charles. See C Sadho ae Li Sheds oe H. Caro. VII teminecht, “Oto? oes cesses. Ger.......!Roessler...... I 63,377. (See B. Homolka) ; Recutet ans ay (cay 847.083. ; 903,588. » and) Ferdinand Blumenthal .|Ger.,.....|....06000.00- XXIIT] 1,059,740; 1,059,741. Liebmann, Adolf ....... Ma pedal Ieee aes. VORA) Poa BORE hm ata ae 404,097. XXIT | 374,250. Bas es gy BG ee ace XXIT | 252,782. ee ee eee at ee 7: s- | Cer... .. , | ene ce oe en «eles XXIV | (m)741,585. t A Geter seat 7415595 PARC Rte, ISRO. oc. on edie seine 7 One ey ta) PEAS eo Rae III | 500,917. Lightipot gi Ohi: sce sevcss-s. Eng...... lessocs settee XXIIT} (1n)83,182; Re. 3,647. g : 31947 Miiller-Pack. II 38,589; Re. 4,746; Re. 4,747. Brown....... II 111,654; Re. 7,420; or 7,430; Re. 7,431; C. 75432. Ed GW Oa oa Assen coo. [e sere ceeceues XXIL | 1,427,215. XXIIT} 834,739. Jiceven Geriatr .245..6.. Gere. i0% oe ) eae A 208,5055 268,506; 268,507. impach, Leonhard ........... Ger....... ochst....... pa AE MAR OESGMER WT eas Pos 6.5 iid wlvin e's’ Gere. . 5... Hochst....... XV__ | 674,137. pe Be a a iN. ¥ Ul trOn yn ass i oe via a oy tert. |Chem. Found.| XXII 1,378,882; 1,414,029; BeMMie tot Aa acaes fe bs 1,414,030; 1,414,031. List, Georg (see A. L. Laska..|Ger....... Griesheim... XV 889,936; 960,652. and J. Flachslaender) pe ge BPE ee Ss a iS ee ree ae oa and Victor P. Gershon ....|N. Y..... Grosvenor....| XXII | 1.458715. oyd, Nathaniel and John G. Daa ei eter ae ec uk ts ¢ 4 oe Baa Ne Feige ciascie- | ele 2 tlenaie alee XXII (Tr) 34,840. Poach Walther oh... oekeislce sss erties: Boehringer.. oe Tei ees Lohmann, Clemens ........... (ree. Pune Cais ee ee 3545714. Lohse, Otto. See A. Luttring- haus. Lommel, Wilhelm ............ Gere Bayer........ XI | 856,536; 856,537; 884,745; 893,855; 902,154; 936,247; 936,248; 961,361; 961,362; 962,712; 985,424. Loomis, Chauncey C. ......... N. ¥ Semet-Solvay. on aoe xXXI 1,427,400. Doretau; Ferman ............- Switz..... Durand scs..0% XI | 844,155; 844,156. (see C. de la Harpe and C. Oswald) Ne ROD OS ia eos caine ss => Tenn..... foscreeeseeees XX _ | 88,793. Lawler VOstar Geass ssc s = Os SAE Chem. Found.| XXIV | (t)1,421,701. LOWE HATES ec cai ane eces Eng...... [rrrseere »...| XVI cane 316,471; 318,484; 333,049. Lowy, Alexander ............ Parner sce and Arthur H. Howald ...|Pa........[eecerrerteeee XXII | 1,449,423. Lubs, Herbert A. See J. A. Am- bler. DGder. Birhard «oscars. +s Geren sas ha hte att aes OCHStae ene oi m) 1,230,185. Liittringhaus, Arthur (see J. Abel and M. Isler) ...... ET es eae Badische..... III | 1,002,066; 1,010,930; 1,011,068; 1,196,127. XV ; ie, 779800, XXII n)968,376. and Louis Blangey ....... Getic hose Badische..... XXTV | (t)1,412,949. and Wilhelm Braren ..... Geriatr Badischew..a' Iit 1,035,023; 1,067,046. 558 DIGEST OF PATENTS PATENTEE pease pe! ASSIGNEE ans. PATENT NUMBERS . iesbach Dey eae areas ie era Gere... Badische..... III 1,018,836; 1,018,837; 1,044,673. Vi 1,083,110. and Ludwig Ejifflaender ...|Ger....... Badische..... XXII | 1,394,851. hs Roca acct Sapper ..... (Boh daceeateanes Badische..... III 1,090,636. and Ernst Schwarz ....... Get oaks Badische....°. III | 1,044,674; 1,044,675. DAtratip aD rmestOseniene eos PXSA5 i oF TTS Gell wats teeta aeevers XXIII} (In) 700,521. Luther, August. See C Millers ieee cdeie ne oie aie creme Maag Rudolf on svccpia cielo Ceres 2. Tschat. out sae III 1,015,329; 1,018,433; XI Cay a and Pant fore cccnesen eee ee sae esis Héchst....... 1,065,063. McCallum, Nat 2 APOE RY ee tord Th a tay ee ae Leeds: 2.,.55 XXIII | (Nt) 283,265. McCann, Robert B. See D. aot Cuttrown. McCormack, Harry ........... RUS edn Shee ee Pe XXII | 1,406,745. McCreadie, John. See M. E. Putnam. McDonald, “Edith OQ... 55.0 4 NevYoo sei (iis ce ea een XXI | 1,222,433. MeDonald, David Bu «.2.... 2. lg a pc oss ht edie Werte ae ene IX 1,396,001. and Jackson Calvert ...... Eng....-- McDonald....| xx vy | (e)1,320,076 1,320,077. MeEirdy, Sarl: Po opens ee D. C..... |Chem. Dev... | xx1r | 1,205,339; 1,308,796; 1,315,220. Machenhauer, Fritz ..,...... She ECHUS Naet tr ceibnlie eles aie se nsrstnteuate XVIII | 308,912. McKee, PRION Be en cee oe INE oh) ase atoberen| erie havabenatetereenare XXII | 15312,127; 1,449,121. and Herman C. Cooper .. |N, Tears MeR Geis 5 osix XXII | 1,458,491. Maeder, Horst. See O. Wolfes. Maennchen, Fritz. See K. Thiess. Mahier William + 24.0 4. 2 ciak te NG Ee eho haca oe tee XXII | 1,405,732. ne Gerald H. See M. Phil- ips. Majert, Wilhelm \....t., ..4<3.; Geri iss dich ited aeeans VI_ | 440,953. = Ewer-Pick XVI | 323,514. XXIV | (m)543,214; 603,195. Mannsgep-Orte ce eee cre) Cer. 3) 35 Bayer cides XXII | 526,786. Mandt, Max and Robert Hold MANM veces see cecsaseceses Geri lie pine eetae wees XXII | 650,332. Mankiewicz, Otto, Julius Alt- schul and Wilhelm Urban ../Ger....... Berlin ii. cies XXIV | (m) 860,636. Mann, Friedrich = 30 o..0 2... cea. Noy Schoellkopf XVIII | 262,680. Mann, Heltirich vNe vex ek cca rey cen en UE PAN es Re ie 2 XXIII | (Ab)779,228. Mansfield, ‘Hans Ou8) Giuaneees Getohiad.. Badische..... XI | 1,028,045. Manss, Walter Ad 24 Goren cee Dae: du -Pont.sec “RV Ob tar 854: Marchand, Robert <<...2... Nethh.t foeteu cae eee XXIV | (m)1,408,462; 1,411,859. Marchlewski, Leon (See W. H. Ciansp yh oho key c eee os (Pesca. se Edgar S. Wilson and ‘Ebenezer ‘Stewart ..|#ng,..... [2 +405 s04950 0s XXII | 633,245. Marckwald)):Leor: Ssh. os Ger....ccclossccccercees XXIII | 721,961. Marshall) Johns arn bake Paveey fered du Pont..... XXII | 1,300,580. XXIV | (e) 1,326,047. Marshall, Melville J. ......... and George S. Shaw ...... @ar wees: Shawinigan XXII | 1,450,982. Martinon, Barthelemy. See C. Savigny. Martius, Carl A.tgsey seine ace | Pe an apes a anes BUTS Bee: VI 268,113; Re. 10,3535 344,971; 358,865; 456,897. Bronnert ica: VI 1 334,257. Berlinnaecawr vI 456,627; 456,628. stun taro tetaterstolonets XVI | 246,327. Martz, Edward. See K. Krek- eler and C. Heidenreich Marvin, Joseph B. Jr. ........ INA Ying SSeS Oe aor terete XXII | 1,442,401. Marx, Karl. (See A. Erlenbach)|Ger....... Berhws os0 55 II 1,105,447. XXIIT] (Ab) 1,183,748. Mathe, Eetnest i, foo) 6 hee Gertiaeies's Hochstuaeassase XV 763,193. Matheson, Howard W. and George E. Grattan ..../Can....... Shawinigan XXII | 1,425,500. Mathieu,» Jeam Avmoy tone ace BA win a) eA een Mes XXI_ | 356,368. Maupai, Kugene I5°. ons. cee Teac Sure here ade stems XXIII! 1,352,014. PATENTEE INDEX 559 COUNTRY OR STATE PATENTEE ASSIGNEE | Group PATENT NUMBERS Mayer, Bertram. (See B. Wuth, A. Schaarschmidt and F. PAW IE Ze ac are Hh ESASLG gg wc a oe x III | 1,097,343. PR eahety) Me nteicare cue iact 6 ewes XXII | 729,502; 757,136. Hans Hertlein and Ehrich Oppermann .|Ger....... Héchst....... XXII | 742,707. REDCAR UATISIR vg StS sf ax'ce aes Tadein oe (ates cc a.cs XXIII | 1,066,641. Moffatt, Miles R. and H. S. STEER AIR ae 1A) Ben oeeen Roese pun cicmice XV /|886,532. Mogenburg, Julius .......... Geras cece Ravyeriess. ses XXII | 953,049. Mohler, Johannes (see _ J. DUE cia fos enka sn eats s 3 SCilds sie cia] eaShe regen « oe XI | 420,164. and Carl A. Mayer ...... Switzs.s.. Durand XI | 444,538; 451,502. Molineux, Edward Ll. ........ IN Ve ae INE es, rene retare peers XX: | 76,935. 560 DIGEST OF PATENTS PATENTEE pei ASSIGNEE att he PATENT NUMBERS Molt iGustavaivur ciatele saiclecers cists Mass dik rit cpoca citer nies XXIII} (1n)179,939; 220,638. Moness, Jacob M. .........+-. N. etic lishosshenerer natin ooh VIL | 1,308,763. Monnet, (Prosper “Pierre 7 0. i.3 | Fro 2... 0 Soc. Chim II 298,998; 387,097. XIX | 499,927. XXII | 606,470; 613,460. ais ewes «we XXIV | (£)548,719; 551,131. Monroe, Kenneth P. ........ Seas RNY Ge one wciena gE merece XXII | 1,357,467. Montgomery, Samuel A. See E. H. Payne. Montmollin, Guillaume de. See de Montmollin. Moore, Wy ont (Soo. orks eee Pee a ile lots aa oe cece eee XXII | 1,358,324. Moran, Robert Co .ccs coe FY at Gaia ie dt Pont, ..% +s XXIV | (e) 1,401,631. Morgan,, Gilbert (1. (o.ee. .. Bag iocw st decree rere XXII | 1,273,901. Imp. Trust... | XXII 1,442,818. Mids Jalevoae Sy sedbinwsocnad Massey ee xis Chem. Prod.. | XXIII} 854,374. Moss, George wANieea aes N. Ha NARA ieee aeatet he sac a ae 64,897. Mott, Owen. See A. E. Holley. Muchall, ‘Theodor? aeccscs ees Clueletcels Kalle ae ur ee XV_ | 796,443. Miller, Armand. See M. E. Waldstein. Muller f:Carloc. hic cae bine as ve Leee’, cies eas Kalle. = sas VI 1,113,468. Badische. i: XVIII} 501,434. and Max H. Isler ........ Geriyen ate Badische.o. so NOE 1,062,988. and Wilhelm Stober .... |Ger....... Bagisthew-ae: Vi 1,168,531. Miiller, Carl Ludwig irene tal pe Caer Ger ensnecee Badische dinene I 546,177; 746,981. (See A. Kern and H. Bull) VI 430,533; 430,534; 430,535; 524,261; 524,262. ‘ XVIIT | 353,264; 353,265; 353,266. anG A rtist, Schinid .. 10s ee Ger......- Badische..... I 716,264. Moller, Carl: Os@ar ud. sees SwitZs..0~ aslev cnet. VI 524,060; 524,070. Durand jo... VI 628,721; 631,089; 640,010. Frochstiraeryor VI 941,088 Bindschedler..| XIX | 576,222; 576,223; 578,578; 84,119; 596,333. Badische..... XIX Paar 82 and August Luther ....... GPs see Hochst... 22.0 VI 1,041,146; 1,069,950. and Alexander Otto ...... Ger......- El6chsts. ase VI 888,837. Maller. Bamihis ort ea cock ok ok Switz Hoffmann XXIV | (m) 1,352,082. Muller “Hermans sa cekisicis eiels Lives ions wis eer'|epetntovele tevorene tate XXITIT | (In) 808,308. Miiller, Jean J. See IL. Jaros- son, Mueller:stigcar! © 2coee ee ose Noes Schoellkopf VI_ | 688,478. Miller, Rudolf (see A. SCHMIGC) 27 Ca. oe roeer Ree OS Brant cane, Hochstiensese XXII | 804,157. and Otto Schwab ......... Ger...... «| Hochst.) ..%s XXIII | (In)723,007. and Waldemar Wollenberg.|Ger......- Hochst). 2056 XXII | 841,990. Miiller-Jacobs, Armand ....... No Y..4 > Miller-Jacobs.| XXIII | 342,207. Russia Burtnettee aes XXIII | (An)243,378; 245,633. Miller-Pack, Jean J. See LI, Jarosson. Monch) “hduard yes spel ree, Gér.c sss. Badische, .> J... (ORs). ose Synthetic..... VI | 1,169,344. Nelson, Hinathan-K.°.......... Didoes sss < U. S. Govt... | xxtv | (£) 1,329,272. INcISON a alnneA ees tis as os b NEN ates a td National..... XXIL | 1,469,586. ORGHCIR MEOTCOL Vege. ciceee sss Switz... |Badische..,.. III | 443,402. Neresheimer, Heinrich ....:... Gerinnass .|Badische..... Ill 1,052,507; 1,207,981; 1,207,982. Neresheimer, Karl, Karl Bosch and Alwin Mittasch ...... Gerke oe 2. Badisches. 5... XXII | 1,274,503; 1,292,019. Preumant, 9 Max soto Cette sits Westfalisch...| " Tx 666,627. Neville, Sylvester M. ........ CE hk f Lee Lohr Bake XX | 396,417. Newsome, Thomas ............ Bas. 5 os Amer. By-...-| xxqz | 683,786. Nicodemus, Otto. See A. Stock. Niessen, D. See G. Kalischer. } ¢ INTEtZKT OR UGO ir atcshoae cess sas Switz acs tae Hochstam mie VI 424,019; 555,658. Niewwiand, Julius A. ......... Pie ere ot Pure alee et eal o-0”« Il 1,326,367. Nightingale, Donald A. See W. Bader. Nissen, Detlev and Erich Saul .|Ger....... Cassella...... Tt | 1:055,287. Nomura, Hirochii.c..25...... JAPAN ree [eve descr cnaus XXL | 130,710. Novotny, Emil E. and D. S. J STG ENN 0 1p ee ae ee a ae N. J see eee Stokes shies) ele a ¢ XXIV (pl) 1,398,146. Woroy, Charlies F.X.......... Rar eere ano oye || Cremetn sien reenact XXI_ | 493-286. Nydegger, Otto and H. Schel- A. ee ae WIZ. 2222 |e ceenesenecee XXIL | 19417:277. Oakes, Francis J. ............ BREN de oh ce pie ese vn 5 5 XXI | 759,008; 872,250. Chere Paul Ts... ccs... Ger....... Badische..... VIL | 739,148; 731,385; 761,007. (See R. Knietsch) XXIII (In)765, 590; 835,462; Victor Villiger ; 999,055. and Paul Nawiasky ...... Geter rss Badische..... VII 948,241. CEI SDM tC. er SWE css, 1) POSE in oo ve XXII | 14455544. CoB Uiit, IRATE ON. Sakis des cesses LS aa age oe ea VXTV (m) 1,299,214; 1,299,215. Oehrn, Hans. See O. Kaltwas- ser. Oelschlagel, Carl (see M. Moel- Ee he Be ae ec) Se ae AZOT, oo eg Betlin’-.32'.3 VI 628,025. Oppermann, Erich (see M. DGOME Ds rad ord se Psa op veces CREE nies Via] F918 4 824 © ce ws XXII | 823,435. Oppermann, Julius (see K. El- Belang — Fischer) ........ Gergee. s. and August Fette ......... 2 eee Peall@ eae oe Scottish Dyes III 1,451,270. Portheim, Emil. See von-~Port- heim. Potter) |) Ralph iS. yes eee Fal Paaet Fea arta Bene aps odie had | VII | 1,322,052. (see C. R. Downs, IL. Weis- berg and J. M. Weiss) Pratt, ,Lester "Ay sandy Fi Nt Briain sa habs Cee oem ts Mass....../Merrimac.... | XXII | 1,311,090. : | PATENTEE INDEX 563 PATENTEE Se nee ASSIGNEE foes PATENT NUMBERS Preiswerk, Ernst ......0060... Switz..... |Hoffmann....| XXIV | (m)1,415,700. Pretzell, Carl. See K. Schirma- ener, OO.” Kenst’ cand A. Schmidt. : Preuss, Ludwig. See P. Seidel. Priebs, Bernhard (see P. Fried- lander, and C. Rudolph) ..../Ger....... ; and Oskar Kaltwasser ....|Ger....... Berlinw...... XV_ | 628,607; 628,608; 628,609; 642,256; 655,059. repens he H. C. See A. L. Laska. 7 Perancee ONION vice vce ecces ir semersee Soc. Chim.... | XXIII | 1,366,023. Pere ECO ues it cele sc iene «0 0's Catia eer Bronner..... VI 332,829; 332,830. Pumimerer, Rudolf ...........- GEN ayccvaies 6 Badische..... VII | 876,839. igiibac! G2 £0.) oe ee ea IN Wineries Robeson....: | XXI | 1,185,605; 1,283,296. Putnam, Mark E. and John Mc-| eNRET, cicul Sek owas nes Mich...... DOW cilce os ess XXIV | (m)1.459,900. Rademacher, Ferdinand ....... Bus sliny cece eas sone XXII | 935,815. Raeder, Heinrich ............. Gef...ese DAyeren suka a’ TII_ |-950,343; 950,344. (see P. Thomaschewski) Rahtien, Arnold aanccscvsresoes GOL, vniss Devens gees as ys VII | 720,217; 984,442. and Carl Stephan ......... Ger......- Rahtjen-..... VIL | 850,444; 937,194. Raiziss, George W. See J. F. ; Schamberg. ; Ralph, Walter M. (see C. G.|N. Y....- National..... VI 1,371,979; Re. 15,182. oe a ae ae N. Y....- National..... VI | 1,415,704. and Lawrence H. Flett ...|Mich......]............. IT 787,221. Ramage, Alexander S. ........ Eng....-- Bostaph...... XXIT 1,365,849; 1,430,585. Gere acne see eee ee seen XXII 1,010,377. Raschig, Friedrich ............ Ger......- Raschig...... XXIE | 1,023,758. and Max Kébner ........ CTE ire id LOS Re i ena XXII | 655,117; 656,263. OS Uy 2 a ae Rath, Ernst J. See A. L. Laska i and A. Zitscher. ; Rauch, Gabriel. See C. Vernet.|Switz...-- |Basle........ vI sahbah d salar ata iS eae CARRIER REE 1,335,397; 1,447,405. Bebey, beni Switz. asleee as ys XXIV | (p)1,316,804. iA as rake Josef Siegwart tai edman, Lawrence V., rchie Weith and Frank P. Brock Hy eg. ee Redmanol.... XXIV (pl) 1,310,087; 1,310,088; Ree anys) c rs 1,345,694; 1,374,526. ee, Alfred. See W. H. Claus. = ae mine Jah or Ae ae earn MasS...++.]-..-seceeeeee XXIII | 50,495; 54,957. ;. Iter. P. ius. Z Rehiander, Paul af a Oe ie Ger....... Chem. Fab... | XXIV | (p)922,040. Reid, John T. and Henry Thorp|Eng..-.-- |.+.-+-+2--0-- XXIIT| (An)612,274; 631,906. Reid, Peter and John Eastwood.|N- J.----- Celluloid..... XXIII | 256,506. Reindel, Hans (see P. Julius) .|Get------- Badische..... VI | 1,126,656. Reingruber, Friedrich. See R. ‘< ae He Nastvogel and A. ansdorfer. 3 Reinhardt, Heinrich .......... Ger....... Kalle........ XXIV | (m) 1,076,840. Reinhardt, Otto and J. Hoerlein Ger....... Weiler....... XV 1,026,881. Reinhold, Christoph .......... Geri es telinte ee eb leseees XXII | 868,008. Reinicke, Gustav ............. Gere reavas Berliticnm oer. XXII | 1,016,092. Reinking, Karl (see H. S. A. no a |Ger....... 4 and Armand J. Stiegelmann Ger.....+- Badische..... XXIII} (In)1,106,970. Reisenegger, Hermann ........ Ger.....+- Hochst....... Ii 450,037. pens Sa gd ey Sete Gerincs selon. bee nceeee XXIV | (m)801,158. Pete OU BEOOUE Wit ruc ys a d+ © Ger.....-- Badische..... XI 431,541. Bg OOF Felon adihe...cc1 AV | Gostes ter, Bapti : Z ee Ier......- Héchst....... XXIV | (m)674,686; 674,687; 680,278. Rey, Hermann. See J. Schmid. Reyher, Rudolf wpe SiR Ger......- Bayer......+- Vv 543,894; 557,022; 559,062; 559,003. Griesheim.... VI 1,084,363. Rhodehamel, Harley W. ...... Ind....... Lilly.......- XXIV | (m) 1,306,439. Rhodes, Frederick H. See Stu- Diicaeh iiss Set A. Schooid odius, Otto. See A. Schmidt. Net Mere) GS osc tose oe nels ws CRO fis wae pig seg alnacein o3 XXII (In) 803,855. ICREICh 6 akg twice Wie Se o's s we el rai vo aihl aceie Rtietaw inate XXII } 1,322,054. 504 DIGEST OF PATENTS PATENTEE Seppe.” ASSIGNEE ae PATENT NUMBERS eg ae ee ea ey i Re Seva ee Switz. )..u | GARY Sy oss.ca ss VI 991,750; 993,549; 1,067,881. Richard, Bernhar XX eee : : Richardson, William B. ....... by Pan be eae Re ae CANE ne 1,412,707. Richter, Gedéon ike hace AUIS ELT gon | eieiatere toy ereiera yore XXIV | (m)1,058,904. Ries. George SBrvak ss cn teess vas TNR Cae onde Cae ees XXIII | 1,318,100. Riethof, Pratz... sc sseewe aes Aus.-Hng..|Blumberg.... | XXII | 1,006,793. Ris; Christopher ....0%..4 6.6 -w's SWECZ, caae Geigy. ..s..0 vI 548,460; 567,413; 571,933} 575,904}; 599,532; 619,5033 644,462. XIV | 455,952; 601,063; 601,066; 613,911; 636,065. XV_ | 636,066; 645,738; mart 696,751; 698,555; 821,378. XVIT | 440,281. ; ; i‘ and Ernst Haager ........ Geri aan. Jager........ vi 888,036. and Albert Mylius ........ Switz..... Geigy........ I 740,468. ” : XV 722,630. and Charles Simon ...... A lets Sere Geigy sass VI_ | 556,164; 615,497; 655,013. Rispler, Alfred L. ......0..005 Mo. -.sio0s Monsanto.... | XIX | 1,381,503. Ritsertwtdnardvera: eceret males CSTE 5.6 cis bos tee e eens XXIV | (m)748,101. ; and Wilhelm Epstein ..... Ger....... Héchst....... XXIV | (m)761,998. Rittman, Walter Fo... 0.3.2.< 0. Pa........ Syn. Hydro.. | XXII 1,419,124. Robertson, George. See F. W. momen bs Ney XV 6,742 obeson, Jaco pe loa tah tes en A pdioric ode fre tte e eee eee 1,310,742. Spires Lote Veeears otk. N. Y..... |Ellis-Foster.. | XXIV | (pl) 1,416,062. Robinson, Thomas S. ......... NN Gas J een eels Sate XX | 181,282. Rodebush, Worth H. ......... Md... ic wus U. S. Ind. Alc. | XXII | 1,430,324. Rodionow, W. See A. Blank. Roehling. Hermann. See E. H. Zollinger. Roemer, Fritz. See E. Hepp. Rogers, Donald G. and H. T. HIOWEUIEC dd. ca se vee oh ae ns PING) Seca: National..... Lee 1,478,061. Rogers, “Homericns coos cee 2a LDL. ewe es du Pontes .o: XXII 1,314,538; 1,413,494. Rohde, Albert. See P. Haupt- mann. Robner, Josep yey? yc ows Switz..... Basie: sess VI 365,400. Romer; Adolph 45.05.00 esa cs Gerace: Badieches.. y, VI __ | 350,576. Kirttrotiseece. XXIV | (t)1,375,9753 1,375,976. Ronig, Eugen. See C. Schraube Rongger. Nikladamcs peer ts Switz... | Sandor..4e5h XV 747,643. Ronus, M. See W. Herzberg. Roos, s Israel) ese. ae Cerise fat Wis sn one eee XXIV | (m)602,109. Rosé. Heinrich the ea Garg ee Hichst? oe a. XXII | (An) 263,964; 263,065. Rosenberg, Ignaz (see F./Ger....... alleys ona. VI 588,180; 588,181; 588,182; Krecke and K. Elbel) 588,183; 613,642; 613,645. and Bruno Helmert ....... Gera we? KalleSren eee VI 613,643; 613,644. Rosenhek, Joseph ............. Ger....... Cassella...... XVII | 412,978; 412,979. Rosenstiehl, Daniel A. (see Z. Roussin and A. F. Poirrier) . re kere COTTON SEO OG VI 483,368. Rosenthal, Emil. See W. Ep- stein. Rossner, Heinrich. See A. Schmidt. Roussin, Francois Z. .......... Heh cote soe es Poirrier. 7: . 4: VI 210,0545 225,908. Roussin, Zacharie (see A. F. Poirrier) sosn4 eee ee Bein eee and Daniel A. Rosenstiehl .|Fr........ She Denise a VI 297,8523 309,882. Rowland, George ............. Tenn..... Rowland..... XXIII | 752,804. Royle, Thomas. See R. Simpson. Ruckers Karl asec cone Sees er poet a Chem. Found. | XXIV | (pl)1,455,5009. Rudolph, Christian H. ..... Peed US paw ee Oehler....... I 382,832; 305,080. VI_ | 396,203; 462,414; 462,415; 465,116; 468,049; 497,032; 516,380; 516,381; 558,612; 558,613; 558,614; 572,723; 579,773; 601,859. HIGCHStce nents VIL | 262,605; 276,888; 276,880; 276,890. XTII 256,599. XXII | 268,543. and Julius Herbabny ...... Geri vies Oehler.ne es VI 504,123. and Bernhard Priebs ...... Geri wins ce Oebler....... VI 395,634; 396,294. ands Emil Viogestereae tines Getic se sas Ocehler. 00. VI 568,540. Rudolph, Georg’)... dc abi fe ee Getic: Bayer ites a flaee XXIII | (Az)976,219; (Su)873,613. PATENTEE INDEX PATENTEE ie ASSIGNEE RMRMRE GEIS. yiaavein's Sis sie: e's 0 ete cise Le tees woe F. Bayer, F. Westcott Almere Acme Sle reiee gar as.c 16 be Getic cr lee ierer ss sacs ame Walter: gacccscesc sess. ve ts | eae Int. Coal.... and Harry A. Curtis ...... 1 Oh See Bregest ys... UMM! PTICGFICH iss vicccess eer i. Elberfeld..... (see M. Kahn and M BAVet wee. srs Herzberg) Elberfeld..... and Martin Herzberg ..... Geri ss sa. Bayer........ Runne, Ernst. See A. Schmidt. Rupright, Howard J. See C. J. trosacker. AMEE, EMME ONG Gntis ih sb ass. NV vice Sees eee eeeees Salathe, Fritz and John R. eee es mek ssc 8 Sls blac «a Switz..... |Keller....... Sandmeyer, Traugott ......... Switz Bayer-Berlin | CIR Ne as esos Sapper, August. See A. Lut eapaare 2 fala Sera ras « « ete sins Badische..... Peasy ASSO pss oe se -- Switz .|Durand...... ge cer... Cassella...... Savigny,) Claude ..:.....-...-. Ld pepe Martinon... AW VOU OL LOULY. sire. ceca ss sess MasS......J esse eeeeeeees Schaar - Rosenberg, Friedrich See B. Beyer. : ‘Bact Schaarschmidt, Alfred ........ Switz..... aS tee see nie As Ate PAVED. od ales aes Switz..... Basle........ BONBG yy LAAWIS? ooele scene cs esas Ger... .peeee eee ees Schaffer, Henri N. F. ........ Pe a's | oe wie Sincaigin, we,0 ee P swite..... |Hofiman...\. Schamberg, Jay F., George nate Raiziss, and John A. a pee Dennanteey Scharfenberg, Oswald. See W Herzberg. Face... en Pari boy Soe a a B. Bibus. Tenn chiffers, Josep isiitiese rere| A Ss try seit Se dee eat Schirmacher, Karlii.........<- Ger....... Hochst....... (see O. Ernst and F. Schmidt) and Arnold Brunner ...... Ger....... Hochst....... and Bernhard Deicke ..... Ger....... Hochst....... and Heinrich Elvert ...... Ger....... Hochst....... and Hermann Landers Lee 2 Ger 70 oxe a6 Hochst ew cence and Richard Leopold eee Ger old stele ee Hochst eh a deate k and Arthur Voss ......... Gere ccs Héchst....... F. Schmidt, C. Pretzel) and W. Schumacher ..|Ger....... Eochst. ssc. SCHIACLOET EMOTO Wet cease rece ie) Bate oe lees eee SenleCel TT ATIDUF . onsen ccs ene COl cease Badisché...+. DYE _—<— vI XXIV GROUP 565 PATENT NUMBERS 256,375; 256,376; 256,377; 256,378; 256,380; 257,242; 257,243; 260,242; 261,175. 256,379. 256,381. 154,153. 1,409,588. 1,439,128. 689,025. 561,615; 567,615; 719,048; 719,049; 1,028,493. 476,413; 476,414; 501,104; 541,572. 677,279. 932,812; 932,813; 950,404; 950,405; 958,830. (Az) 972,130. 1,016,295. 227,588. 406,669; 406,670. 647,279; 647,280; 647,281; 607,545. 410,739; 538,027; 538,215; 564,801. 573,299. (Az) 793,743. 644,331. 413,562. 904,809. (Nt) 412,680. 210,808; 236,634. 898,845; 966,478. 915,385. 354,746. (An) 481,591; 527,457. (Ab) 592,022; Re. 11,647. (m)602,646; 602,690. (m) 1,390,972. 837,736; 936,367. 943,470; 1,342,134. 1,270,123. 624,256; 627,783; 647,236; 665,606; 672,714; 680,283; 693,670; 724,743; 733,280; 778,610; 837,128; 1,045,196, 823,294. 1,422,880. 881,159; 888,852. 867,305; 881,158. 1,076,321; 1,077,492. 892,807. 1,001,458. 867,306; 881,157; 1,001,457. 1,123,390. 827,468. (pl) 1,294,836. (An) 893,384. DIGEST OF PATENTS COUNTRY DYE PATENTEE OR STATE ASSIGNEE GROUP PATENT NUMBERS Schleicher, Erhart ...... Ai Ger..... +.| Badisehe..... I 516,577. (see C. Schraube) VI_ | 671,806. and Atigye Derren t autererms cee Cer Ur ire ees Badische..... VI |741,9036. Schlenk, Wilhelm .....:¢00s0. Gertie aks Weller. i; 6.8 XXII | 895,689. Schievussner, Carli) sete nes eps be peat ath Hochst recs 3. XV_ |649,218; 651,122. Schmatolla, Otto. See R. Reiss. SchmidmAlbert uw. wees exe SwitZieaa Nwanee eee cael XXIII | (Ab) 1,417,206. Schmid, Ernst. See C. L. "Mill. ler. Schmid, Henri ...... ei erareiate Udi rel ve ea ee Hochst. sens XXIII | (Az)598,118. Badische..... II__|863,761. XXIII | (Ab) 963,656. Schmid, Jakob oo... ¢ de eens ... | Switz Basle........ VI | 402,980; 449,629; 452,197; 493,563; 493,564; 525,626; 5575435; 5575436; 557,437; 5575438; 557:439; 557440; 558,438; 620,368; 620,369. XI | 404,309. XXIL | 425,525; 455,442. and Jacques Bachelut ..... Switz/... Basle. ccs. sss XVIII |519,971; 525,627. and Karl Jedlicka ........|Switz » Ppaslesscas . , sl Mibchet ary VI | 728,021. VII |807,782; 868,295; 872,085; 872,086; 916,031. XV_ |778,713; 818,980; 829,740. XIX | 656,426. XXIII |(An)1,175,997; (In)906,307; : 1,005,481; 1,027,441; 1,058,019; 1,058,020; 1,058,021; 1,239,526. and Wilhelm Bertram ..... (POT. 5a 9 9 Hochst VII |867,670. and Fritz Bethmann ...... (eras Héchst....... XV |728,623; 776,264. and Ernst Bryk 32.00 \sk TFET. Paves ole Hochst....... VIL |877,743; 881,624; 916,020; 916,030; 947,030; 959,617; 963,813. and Georg Kranzlein ..... Getic. seas Hochstac. see III |958,325; 1,038,003; 1,046,498; 1,052,520. VI 1,028,139. and Erich Kronholz ..... (Seo ctws Hochstsidcass VIL |812,598. and Gustav Kronlein ..... Get. c. pass Héchsty sis in. XV __ | 1,128,371. XXII | 1,128,370. and Ernst Runne ...... Getigcdaw Hichet..2..s24. XXII | 1,128,360. and Rudolf Miller ....... iS eee Hochst.3.-cc VIL |765,996. and Carl Pretzel ic 7 oo Gere. yet Hochst, (0.0 VII |872,585. and Otto Rhodius ....... Get... s Hochst. gecey XV 773.840: Heinrich Roéssner and Hans Raihorn jt cee ees Getiersen HGchat.. osc.s VIL |918,920; 1 043,468. and Otto mSch wane ages Ger...... Ry EL OCEIST erpareteae XXIII | (Su) 901,746. and Otto Steindorff ....... Getidessus Hochstewucues XXIII | (In) 1,054,039; 1,057,886; Su) 1,095,237; 1,141,148; 1,057,887; 1,085,361; { 1,094,683; 1,006,060. atid Kart Chieda yes. ee Gero ieee Hochst Jann «ee VII |955,699; 1,028,911; 1,061,781; 1,070,541. and Ernst’ Bryk “45.24. COP ad wee Héehstvcccts XV_ {1,128,368. and Pesta: Ag rt eee ee 48 PR hE HGchst®.7cee VII |932,334. an rns Tye Neches ans EL, erent Hochst. i oa 68,697. Schmidt, Carl. See C. Schraube Mes ae Schmidt, betaine (see G. teinike and chirmacher)|Ger....... Hochsts ups. e VI |647,237; 737,967. and Otte “Rrast.4 s.r, one Ger... Héchst....... VI |582,958; He Heer and Karl Schirmacher ....|Ger....... Hachsts ve. sae VI |826,279; 826,280; 826,281; : ‘ 826,282. Schmidt, Ludwig ............. Geel ae Se accae ey eine XXIV | (P)1,326,973. Schmidt, Maxmilian P. ....... OFS hey ee Rallessoydiae III | 1,209,212; 1,261,858. and Heinrich Roese ....... Gefovas ie Kalle. 2.5... 1 VIL \apaeares PATENTEE INDEX 567 COUNTRY OR STATE DYE PATENTEE GROUP ASSIGNEE PATENT NUMBERS eee UNG nas Pals kha es os Gera. ae Badische..... VI__|936,951; 1,075,305. Chem. Found.| XXIV | (t) 1,336,759. mcumidt, Robert En ci vessseses Se Op a see Bayere sides III | 446,892; 446,893; 476,418; 476,419; 476,420; 476,491; 502,765; 503,295; 506,265; 59553493 595,350. Elberfeld.... | III |590,425; 500,426; 599,427; 607,659; 605,568; 623,219; 623,220; 656,668; 656,669; 658,513; 658,514; 675,572; 785,121; 785,122; 785,123; 812,684; Re. 12,548; 826,750. XXIL 742,910; 74316645 757.0873 757,050. XXIII | (An) 649,486. and Arnold Fischer ....... GOT ey sas » pelberfeld.... . III | 790,079. and Andreas Jacobi ...... GE ee da .|Hlberfeld.... IIT |666,702; 675,573. and Adolf Sertorius ...... GOP oes s Elberfeld.... TIL |687,657; 687,658. SU tg 9 Ger....... Elberfeld.... IIL |812,590. and Paul Tust .......... era. cnn s 6 Bayer siecs se: TIL | 496,139. Elberfeld..... III |605,921; 656,670; 656,730; 675,574; 675,575; 836,220. XXIT |755,801; 765,201; 765,637. Schmidt, Witt) ee Gerlach un puilcasséllacuasec XV 892,455. Schmitt, Rudolf ............. Bee ees von Heyden.. | XXII | 410,295. and Carl Kolbe .......... GetrAnccr. von Heyden..| XXII 350,468. Schmitz, Alexander .......... ieetre res ss Cece cceeceeces XXII 861,397. XXIII 964,565. Schmiickert, Friedrich E. .....|Get----++- Pravin te is ee (In) 386,933. Sebneider, Hans ............. Ger....... ges asesceees a (m) 942,674. pchultenpaut, Jnarl ..........; Ger....... riesheim.... 887,348; 959,078; 976,401. XXIII (In) 1,011,500. Schobel, Heinrich. See E. An- derwert. prota aes (see A. Ger Sete ee ee Ger... ..... UE he OE ee Gees oo. Berlin....... VI | 1,408,405. Scholl, sy ree aay dea Otic esas Hochst. ; 2:3 vI Diy Stes eas. 741,552} BRE AYIZ ecnele otic aerate & ie 18,981; 958,774; is Q. Ernst and EK. Ko- 1,028,140; 1,029,639; g 1,032,433. XII |656,857; 656,858; 656,859; ay 658,593- and Arnold Hess ......... Ger...... .|Hochst....... i ee and Willy fone We A es rer) ae Hochst... ne eee Somer wnolend HH, -..4-3.4.....: Ger....... Badische..... XIT B28,7763 a ee Badische..... | Hl |787,859. ae Re ye eS ae) Ger....... Badische..... ee ee and Max A. Kunz .......|Ger------- Badische..... er nadie Schrader, Hermann .......... ne SLA AICS Wa diech ot: III As selraube, Conrad -:........... CEae > 5245220: XIX 1|533,820. XXIII | (AI) 352,361. : I | 700,565. dH T. ERROR ie Sic 's = Badische..... bd 2905+ ae hcocn Ea said APA Ger has Badische..... tA TP aL Pas and Erhart Schleicher ....|Get-.--+-- Badische..... af seen 860,575. and Hans T. Bucherer .. pee Berne Aes See yes? XXIII ig Cee 0733 531,074} ; Cf dad: adische..... 9735 1974; and -Carl Schmidt ........ Ew 31,075; $31,976; 531977. and Walter V. Tetzner ...|Ger...---- Badische..... 7135507; 718,025; 715,389. Schréter, Ernst W. a pia ote c ae Liew bee bie oe XXIV | (m)3 18,662. f Cordes....... XXIV ind SEa2 04: premiere meee er fiers... binles sees et in dee VI 73,795; 1,241,153. TE RAS Ch | ee Gers... « a he iy Wil ulote.sOs0 eisoa cent 1,193,820. Schiilemann, Werner ......... Gere sts. Bayer nin sisic-sic XXIV |(m)1,474,567. “eer ance Gustav K. See W. ehaghel. tian: MERON Sere ee oy Geri vec. Badische..... XV_ |[687,072. Schtitz, Ludwig. See W. Schiile- mann. Schtitze, Leopold and Robert Fischer ....... Gertie ed eae aS XXIII | (Az) 1,096,198. 568 DIGEST OF PATENTS — —o— SS e>SESE—SS>=Eo_ _S——_—=]"]='~a"=_a=a]™"a>a]"{—{a—_={=ajay_ey_—===—=—=E=—=—E—Eae—EeE=>=E=E=Eae=Eae=E=Eae=E=E=Eeyey_—ae=_—aeE>—eE=E>=EeEeEeE=E>=>>>l—> > >l>l>=>—>E>E—=—SS=SS=SSSSSS———— COUNTRY DYE PATENTEE OR STATE ASSIGNEE GROUP PATENT NUMBERS Schuler: Tosefwce nous avers Switz..... | Basle... 0. | XXEV | (m) 1,384,637. Schulthess + (Oscars occas heir Ger yaa : and Leo Kerkovius ....... Gerics saan Bérligvas es. XXII |851,444. Schultz, Gustav (see F. Bender)|Ger....... Berlin. oss: sii V STT.0535 Schumacher, Willy (see K. ; VI |418,657; 462,824. Schumacher nO son v0 eee owen Geta. es Hochst....... VI |846,511. Sohne. Fe. cts ive wale’ ary atice ce Gefen Sinise Badische..... VI |246,221. Schwab, Otto. See A. Schmidt and R. Miller. mtr Des Franz. See W. Herz- erg. , Schwabe, Rudolf ............. Ger cracae< Moenst. <.. 7: XXIV |(m)1,076,160; 1,181,485. Schwan, Nicolaus (see B. Ho- MOT AN WS Chath ie Meme are ae oe EPs viet , and Wilhelm Zedel ....... Geray.css Hochst....... XV_ |658,286. Schwarz, Ernst. See A. Lwut- tringhaus. Schwarz,’ Maxinivei.. vee seeas Aus.-Hng..|---+eeeeeeeeee XXIII | 1,019,092. Schwarz, Paul. See C. F. M. Schaerges. Schwarzwald, Gustav. ......... N. Yin... [eee ere ee eens XXI_ | 240,467. Schweitzer, Hugo ..........-- oS panes Bayer........ VI |1,429,781; 1,429,782. (see A. Zart and K. Desa- : mari) Dickerson (1%4)| XXIII (Ab) 539,550. and ‘Artbict, (Zant laine es wis TOT sh e'8 Bayer.......- VI_ |1,009,796; 1,009,797; 1,024,031; 1,038,209; Re. 13,550; 1,038,210; Segaller, David, and D. H. P kecsante egaller, David, an . H. Pea- im ivi LEP PIIAE fo seine ae Mon ee Bidens British Dyes. | XXII |1,465,680. Seiberth, Max. See M. Hart- mann. Seidel Dr) Charles ii.2 . ss eee IN OY civatendt ot ecerecescs XXI | 76,107. Seidely Heinrich)... ccs ve seed Aus.-Hng..|Kalle.......- XV_ |687,581. Seidel; WPattl Rei e o sin tee ee Geren ssn Badische..... VII | 698,328; 699,581; 798,077. (see R. Knietsch and D. Vorlander) XXII | 690,325. XXIII | (In)692,720; 744,417. and Ludwig Preuss ....... CT ry Kall a XXII |661,821. and Robert Wimmer ...... Ger... .. ef e cere eee ceees XXIII | (In) 794,049. Sethertarb rluno sine eereeciceleces Geri. sa von Heyden..| VI 493,413. XXII | 407,906; 488,290; 578,839. mM Ais oat As XXIV (m) 501,235; 604,503; urt ili an ax : 749,634. Giasiner tc Srey Ger howe von Heyden..| VII |714,042. and Otto: Meved.icece ces Or Gisae se von Heyden..| XXII |887,050. Scilet Pant Hi oe eee ern ws Badische..... XXIII | (In)794,050. Sellon, John S. and Robert Pinkneyiciceea cote eer tee Bagi se Paar ers ass XXI_ | 167,360. Selwig, Johannes ............. Ger caress Selwig, Lange | XXIII | 541/573. Senderens,.J canbe ae ae ee ae Fr. iss. Poulenc...... XXII | 1,265,956. Senger: Robert. 4 ocice ee eioen N. Yewese [outa nenneccws XXIII (AI) 475,616. Sertorius, Adolf. See R. E. 5 See a CY DErth, Lvermanny ss mies crs CT... e006 - and Moritz von Gallois ...|Ger.....-- Hochst....... XXII | (Az) 595,894. Shaw, George S. See M. J. Marshall. Shorey, Edmund C. .......... D.C... ae [ohne eee XXII | 1,450,990. Sibley Robert L. See C. W. Bedford. Siebert, Hans. See A. Wein- berg. Siebert, Otto. See A. Clausius, . Gley, W. Herzberg and B. Schoner. Sicgle, Gustey Ausra N. Y..... |-°- sitet eens XXI_ | 66,897. Siesniund: A UeIgt Science ae Ger...... Radische..... XXIII | 650,556. iegwart, Josef. See E. Reber. ; Siepermann, Otto ............ ING Teetce) ts Consolidated. VI 1,073,784. Sigwart, August. See W. Neel- meier. Silberberg, Rudolf ........... NP ince Hoops (%4).. | XXIII |320,820; 320,82. Silbermann, Theophile. See A. Ostrogovich. Silberrad, Oswald ............ BAgeo. asne| ces Sota ee XV_ |1,268,803. Siller, August. See C. Rumpff. Simon, Charles (see C. Ris) ..!Switz..... Geigy sci sees VI 1628,233. ee PATENTEE INDEX COUNTRY DYE PATENTEE pe eras ASSIGNEE | croup Suuon, Sigismund E. ......... Dob Ad Bint casey | Ctra sey are III Simpson, Richard, Arthur Brookes and eonomas Rovles. | HN. .s.0 (ecce cece e vans XXIII Sener RLIGCTICN, (5 ccc kek os Serie ct ss Griesheim.... III i igs Ub aa ae Bk a Gerdes ies Griesheim... III eel) ana Altred Holl oa........ Geri eos nsk Griesheim.... III and Ernst Milarch ....... (Gerencncdee Griesheim.... | XXII Skirrow, Frederick W. ........ Cait mes Shawinigan... | XXII afd lames oDick™ .c.5 sess Cant scsi Shawinigan.. | XXII Skraup, Zoento H)............ Aus.-Hng..|Badische..... XXII XXIV IUD OR ISS Bole cca ne cs os INGEN. 3. us National..... XXII Snelling, Walter O. .......... IS gots res sere alll Meets « sie es XXIV GCE IG Mees cc ine on seek eas aery..«vs oe Frochst 234 3s. I V VI XXII Somerville, William .......... PUGET « inci) laa de oly wales « XXI Sommer, Rudolf ..i..c0s...-. Aus.-Hng..|Fritzsche..... XXIV Soutar, Charles Wm. See F. W. Atack. Specht, Leopold. See F. Erban.|. Speitel, Rene. See C. Vaucher. Sehce PAViOn <.s.- XXIII GIG Ot, GAREOIG Socrd dss cee ss Switz Sandotay «45 XI XVIII XIX XXII 569 PATENT NUMBERS 686,356. (An) 182,234. 999,680. 1,044,933; 1,070,196; I,150,152. 999,062; 1,119,546. 1,329,435. 1,103,383. 1,429,650. 1,449,918. 237,917; 237,918; 241,738. m) 295,825. 1,419,695. (pl) 1,430,034. 712,421; 739,117; 766,540; 794,052. 1,015,354. 646,711; 739,118. 805,890. 1,193,838. (£)804,682. 326,601. 251,384. 1,414,441. (pl) 1,263,813. 302,790; 303,335; 306,969. (Az)302,791; 306,546. (m) 495,124. 1,155,765. (m) 886,085. 1,318,022. 1,411,529. 1,461,435. 611,870. 221,114) 22,050 cate nro. 22150175 221,11 oseeet, f10); 221,120; 242,707; 256,401; 302,170; 313,118; 1,235,253. 252,273; 252,274; 253,443; 253.444; 253,445; 254,064; 254,065; 255,349; 255,350; 266,912. 256,400. 1,421,604; 1,421,605; 1,432 308. 1,437,783. (An) 1,145,934. 647,338; 901,657; 992,613. 603,016. 1,054,247. 731,139. 579 DIGEST OF PATENTS COUNTRY DYE Steinike, George and Frederick Schmidt™..,..[Getisccics feseweececsbaa VI | 576,511. Hochstteeucc VI_ | 603,093. Steinkopf, Wilhelm ........... ee rE ag Choe eR XXII | 1,085,708. Steinmetz, Charles P. ......... Nii VOR) ao ees wares XXIII | 894,547. Stephan, Alfred :...4...-06-06: Gere os ior pathlstet ae Per XXIV | (m)812,608. Stephan, Carl (see A. Rahtjen)|Ger....... |-...-seeeeee VII |1,427,863. Stephens, Henry...) sess #0 POR iis hs ois a wise is = er XX |4aar; Re. 3. Stevens, Maria As” lies ce ace cies Mint. <4: obsecaeweae che XX |562,045. Stewart, Ebenezer. See E. S. Wilson. Stiegelmann, Armand J. (see K. : Reinkidg)< eo cota n pa aate Te, Badische..... XXIII | (In) 657,320; 680,894; 699,033; 720,501. Stine, Charles M. ........--%: Denese du Pont....: XXIV | (e) 1,370,067; 1,450,675. and John L. Gilson ....... DE teis'sen du, Ponti es. IX |1,393,714. Stober, Wilhelm. See C. Miller. Stock, August. (see B. Homol- t Mea div hidicta tans ontbue pane wuss iene Ger Srey, Hochst 2rsc5, VII_ |[662,703; 1,050,179. e XXIII | (Tr) 1,043,271. and Friedrich Heim ...... LO ott ep ay Héchstsy ss oee XVIII |995,494; 1,042,498; ‘ 1,065,405; Re. 13,969. and Otto Nicodemus ...... Gero. 25 Hochst sls 60s sie XVIII | 1,217,238. Stolz, Friedrich ........seees: REE Sia sy we Hochst....... XXIV | (m)579,4227 1,017,699; 5 1,053,240. and Georg Korndérfer ....|Ger....... Hochst....... XXIV | (m)o990,310. and Karl Streitwolf ....... Asef ees Hochst....... XXIV | (m)936,380. Storey. Brite veeerch dca caees « Aus.-Hng.. | Hochst....... VI_ |569,302. Strasburger, Josef ...........- Russia.. Berlin....... VI__} 399,581. Straub. Prite) .eewics woe vily ok Switz Basle,....4. XXIII | (Az) 1,440,566. (see G. Engi and J. Grim- mer Strauss, Prank “A. iicacsiee ne at rere OnE ere it: XXII | 1,367,898. Streitwolf, Karl. See F. Stolz.}_. Strosacker, Charles J.) ss... «804 Mich.3 0... Dow......... VIT_ | 1,442,743. Mich D VIL apes s 8 and Howard J. Rupright . [ls nt OW. sseeeees 1,431,606; 1,473,887. Strupler, Albert : ie.e Uk che Ag ates os see eee Hochst.....5. XXIII | (Tr) 1,085,178. fuer. Pera art Colles. seats o outs CT... eee : and Walter Grob ......... Ger) ss a8 Chem. Found.| XXII | 1,421,743. Stiircke, Adrianna ............ Nw Mae anh Eee eyes elena XX | 1,219,186. Sttisser iCHardine .souia sustelere ane Geto Sa 95,6 Bayer........ VI 1,457,235. Suida, Wilhelm. See M. Becke. Sulzberger, Nathan ........... Ger...... o [cece rece eeeee VI |879,424. N. Yoeees [eceeeesscceas VI |902,021. Summers, Bertrand S. ........ Mich... of ecct esac ek aa XV_ | 1,053,676. Sunder, Charles. See M. Bader. Susemihl, Theresa M. See T. iy veereods S Ach k utter, eodor. See I. Ach. Suzuki, Umetaro ... he a eet se Japan elie bi[ ee aa el se: wreelacy re XXIV (m) 1,330,288. Suzuid;) Zenshita <).20e ewes eas Calif... 2. [oeeee eee eeeee XV_|1,244,795; 1,244,796. Sztatikayy Abs ).cielonwtssane: Hung..... Chem. Found. | XXIII | (Tr) 1,357,482. Taggesell, Richard ............ Ne Yiastetes Schoellkopf.. VI _ |618,963; 683,190; 1,327,688. 8s XXII |659,496; 659,497. - Tagiani, Ernesto. See R. Lepe- tit. Talbot, George W. .........0-- R Loe vabeccae ene eee XXI_ |99,496. Tambach, Rudolf AN ay Sed oy NR Ger acti isce'e Chem. Found. XXIV (m) 1,391,705. Tanburg, Arthur P. .......... Dele du’ Pont; 255 XXI_ | 1,422,494. Tannehill, Arthur LL. (see H. N. \Copthorne)) 2... eek Ahem se TST CL, ‘Srate tetera lub sven stave suet eae tees XXIV | (pl) 1,389,791. Tauber Irngts i evivwunwas oes Ger 2530 Eochstemn sya XXIV |(m)596,797. ‘Teichner, Gustav: es aceecieiewiaen a PAIGE ielevelcravsn ie eis iets ae ote sialete XXII | 1,436,214. Terrisse, Henri and Georges 2 Darter raven cas Ge oes Witt... Badische..... I | 637,183. Tetzner, Walter V. See C Schraube. Thatcher, ‘Charles? J. 40..le< 0s. NVica boas tae ean XXII | 1,405,954. Thauss, Alfred. (see O. Dressel and Mi Bulk} ooh oes ee Pe Elberfeld.... | VI |794,568. Bayess vase XV_ } 1,081,638. and Alfred Giinther ...... Geri see Rayétian.e sas XXIII | 1,450,463. Theta si riedricho laos) r nese nat Geico ven Lee cinelere aiete XXIII } 983,951. Thisle, AIbrechtoas sb ehewee Oi Ne cay Chem. Fab XXIV |(m)1,045,759; 1,091,870. _ and Georg Wichmann ..... Gers vere: Chem. Fab XXII | 1,075,171. Thiele, Johannes Sh aoa Ned tase crate Germans Badische..... XXII | 546,604. Dhies,: Peismrich ie cute eae Geren soe Cleff (%4)....| XXIII} (Ab) 452,324. PATENTEE INDEX 571 eR a PATEN TEE alain A DYE OR STATE ASSIGNEE GROUP PATENT NUMBERS Thiess, Karl. (see A. Schmidt/Ger....... Maennchen, A. Steindorf 1,151,628, (In) 1,426,522. Xx XXIII ead °F.) Gilroy: . 2.5. ... a Ger wee. ce Evochstseriee. III 853,041; 8 : : Thomaschewski, Paul ......... Gersee. sare Bayerosecace: fer AE ae pea (see CG. Thun) and C. 993,736; 1,004,107; Unger) I,010,463; 1,028,637; a Ry at 1,044,603; 1,0 92 ; I, ’ . Elberfeld III toys rs - EE AV OUats ws ale we 961,387; 961,388. in : SG ee eS ICE Synthetic xt Cans siege 2r7- H. Raeder, W. Mieg F AE. = BISCUET fries 5 4 sins SrOE a 5 ates Dayerva > as Ill 970,278; 971,224; 971,225; €. 13,257; 986,521. Mtns, SOCAN .6..0.2..5:. CEL rd Os Leah cise eens o's m) 503,066. Thon, Eduard. See W. Herz- XXIV | (m)503,066 berg. Thorp, Henry. See J. T. Reid. Thin, wnat (see RR. E. Ps UE aa Gen a ses Elberfeld. . III | 608,238; 623,638; 746,405; 844,835. ; hee Tust and Paul Thoma- - eae poet Se Oe CBirateie ais yathetic. «2. | XNTT An) 1,090,352; Tigges, Hermann. See P. Jacob- T} (An)1,090,3523 1,090,353. son. ies hice ( Cc Me Fiz : 5 Ee bac Roe RS chre BE XXII | 722,336. katsch, im (see?P. Julius) .|Ger....... adische..... VI 671,902; 671,903; Tobias, G. See F. Kruger. ol 771903; 671,904. GCUET ELAS cakes ss esss0- os Ree Bayer. is to's XXIII | (Su)873,636. Ne Y.o.00 | Bayer... 0s XXIII | 900,130. Grasselli..... XXII | (Az) 1,417,860. Poel goyaney “Aly .4.......+- hs eee (aes XXIII | 1,289,968; 1,367,930. Townsend, Clinton P. ......... De Cr Hooker =< 5... XXII | 1,468,220. Toye, William. HOR. ae. cise. ee ae Fabric Orn... | XXTIT | 250,302. Mig Led Oo ED ie, en Lh ee ee oe Chim... | XXIT | 666,570. TICS. wees ae XXT Oo : oO. Tropp, Willy (see F. Scholl) ..|Ger....... Héchst...... ee ee Tramball, Harlan 1,. ......... Thien a> and William L. Evans ORO ea. U. S. Govt XVIII | 1:4025195.- Turner, Joseph. .... ces esese Metco: Fee teas ees ee VI | 655:529. IX | 743.778. XXTIT | (11) 888,942. and Harry Dean ......... ENG he ates etree wisiae sone | LUEL. | 987:4375- 1,014,062" 1,014,983; 1,014,984; 1,028,306; 1,099,676. Tust, Paul (see R. E. Schmidt,/Ger....... Synthetic.... | xxyry | (An) 1,126,591. P. Thomaschewski and C. Thun) Tuttle, Herbert C. See P. T. Austen. WAP PAUSED AG ci Golesi es s's DRO G vil averc dee ae ajc. XXIT | 628,503. Mytee hy Obial Sci 6 iicsev esses Dee, Pree te es eee XXT_ | 458,244. Uertberg, Wilhelm ........... BOE are <0i8 Budeeieimricn Heimann ....)GEr..... 00 |. cccecesecses V 617,703. Whlenhuth, Rudolf .:......... Ger asec. Hiochst....... III 943,717. (see E. Hepp) XXII | 15194,943. Unigann, Paul ...........2.: Getiys - sis von Heyden III | 653,492. LON Ue Tebsiy- Lek g(s 2 SOA a ee Getinc ccs Berlina ones I 643,569. Til 961,047; 961,048; 1,001,325. XXII | 993,915. RIS ATIBUL censuses’. Ger..... wa |oeseoseeecces XXII | 1,466,683; 1,467,258. Mire agard. . igs. i seen'ss ss Geren. sss Hochst....... XI | 364,320; 366,356; 366,357; 649,227; 649,228. XVI | 362,592; 366,639; 366,640; 384,480. and Moritz von Gallois .../Ger....... Hoechst. 22.4% VI 569,395. Ulrich, Moritz (see R. Kothe) .|/Ger....... Baveraace «sa VI 415,258; 417,294; 417,205; 417,296; 423,970; 466,202; 466,841; 468,142; 476,335; Re. 11,308; 476,336. Elberfeld VI | 611,663; 661,664; 619,518. BRVES ce oe pee XV_ | 560,334. XXII ! 415,259; 444,679. 37 572 DIGEST OF PATENTS NTRY DYE PATENTEE pease: ASSIGNEE GROUP \ and Johannes Bammann ..|Ger....... | Bayer. .s> os. VI XXII and Karl Heidenreich (GN, NL Elberfeld.... VI and Richard. Lauchen.. ieee Cerne: Daly Eiaksteas ts cc's VI Johann Bammann and Martin Herzberg .|/Ger....... Bay eficcvaraaes VI Ulricha- es Mrast easter eee ae Ger As Dalila ai VI Badische..... VI Dabl ayes are XXIII Unyer, (Oskari ey rc taicm aes (rer, Saisie Elberfeld.... III and Paul Thomaschewski ..|Ger....... Bayer.y.sera8 III Unruh, Max C. von. See von Unruh. Urban, Johannes. See M. Fremery. Urban, Wilhelm. See J. Alt. schul and O. Mankiewicz. Utzinger, Max. See E. Stein- bach. Valentiner, Friedrich W. S. ...|Ger..... ce [eter cere eeens XXIV Vanselow, Albert P. and Walde- mar. See C. O. Benedetti. Van Skelline, Isabelle J. ...... DNctek Sc oh oi A spevicrae Wiel e ares veee XXIII Van Winkle, JohntAsie. sees ses Mo... . 22. [ere e ee eeeces XXIII Varma, Phuldeo S. See R. L. Datta. Vaucher;* Charles |. kc Sab eee Switz Durander. sen XI (see C. de la Harpe) and Rene Speitel ......... Switz Durand... ..: I Vaughan, Henry W.isoecs. 442 ROL Lee} ats ee eee XXIII Weres, (Rataer Cre weic eric, Was MATTE eee and Marcelino H. Vegas. ;.|Argen.....]:-«2e+¢s08s% XXI Venter Otto soo. wie eae ee Greats Soro Gwrrermerarneea XXII NEE svn Biete ata sasha teae: he ee Eten ers Soc. Ang.-Fr.. | XXIV erner, amille and Gabriel Rach 25 Poe oe ee shee ee ees witz Grasselli..... XXII Versmann, Frederick. See H. . Fenner. Vettercke, Frederick G. ....... NEWS eee eens XX Vicongne, Auguste. See EF. de Grousseau. Widal Menrl RG h conse eee Fey Saanich edule ee cane XV XVIII pe? XX and Alcide F. Poirrier ...|Fr........ Soc. Chim XV Vieth, ‘(Hermann “2.82 oee eee Germs. Knoll aes XXIV Vignon; “Leo snout eee Ered Site |'cdals whats he ee VI IX XVIII Ville t Jaties? ee oo aca eae oe [ah hops ERASE lec A ok nk A XVIII Villiger, Viktor (see P. E. Ober- reit and. Po) Julies) ies asus Geren teva. and Heinrich von Kran- néechfeldt sos ec pe wean es (FOTIE aise lo hace enero III and Ernst Fussenegger ...|/Ger....... Badische..... VI Virck, Paul. See H. Heimann. Vises Gerhard Nit ences ete (Geta henne Dahl wee se XXIV Viiet, Elmer B. See A. S. Bur- dick. IViOEELET EEGTEIS Ei Neustete slerteree rete GreE ES Scshans | Stoke one a trerohe XXIII PATENT NUMBERS 482,106; 496,392; 498,759; 498,873; 498,874; 499,198; 506,284; 509,635; 512,493; 524,005; 533,508; 544,699; 544,700; 556,298; 578,432; 593,790; 608,999. 540,412. 678,323; 687,171. 476,337; 501,118. 515,381. 911,186; 1,014,539; 1,022,612; 1,028,239. 1,077,655. (Az) 890,254; 910,130; 936,260; 937,741. 654,294; 654,295. 994,803; 995,306. (m) 811,884. 192,201. 334,140. 929,350. 1,418,852. 272,499. 1,330,992. 764,966. (£) 646,772. 1,437,571. 9,890. 523,138; Re. 11,659; 594,105; 594,106; 594,107; 601,363; 601,364; 601,365; 608,354; 608,355; 618,152; 622,299; 629,221; 630,952; 1,265,836; 1,265,837. 603,300; 609,598; 609,599; 621,393; 664,450. 595,897; 618,809. (Su) 549,036; 549,082. 532,503. (m)678,070; 998,726. 310,155. 324,615. 319,646. 589,766; 591,309; 701,427. 1,396,483. 990,173. (m) 512,590. tae (Su) 708,429; 724,631; 1,200,055. PATENTEE INDEX 573 COUNTRY DYE PATENTEE OR STATE ASSIGNEE GROUP PATENT NUMBERS Voger, Emil. See C. Rudolph. Voigtlander-Tetzner, Walter. See W. V. Tetzner. Volger, Franz. See P. Ott. Winjimctiboy (eetih Ae aay erie ies Clee hee Bayetinn ted cccts vI 902,186; 1,020,670. DAVEE Sess e ses XII | 935,829; 935,830; 969,428; 972,951. Synthetic..... XII 1,098,600. Vollberg, Hermann. See A Klages. Vollbrecht, Heinrich .......... N. ¥..... Schoellkopf...| IX | 333,036. and Carl Mensching ...... Se Baa etapa Schoellkopf...}| VI 333,035; 333,037; 333,038; 333,039; 333,041; 333,042; Si lssrocee. 333;034; 333,035; 333,040. Volwiler, Ernst H. See R. se he Adams and O. Kamm. Vongerichten, Eduard ........ Ger....... Hochsts; ts ss. XRT Wa 72685. von Bolzano, Friedrich ....... Ger....... Hichst..... /. VIL | 712,246. (see B. Homolka) von Bramer, Harold ......... NON cs te, Eastman..... XXIV | (p)1,421,869. von der Linde, Carl ......... Dae, ae ek pane XXII | 596,043. von Diesbach, Heinrich. See A. Luttringhaus and M. Isler. von Gallois, Moritz .......... CP esis so o's Hochst....... VII | 706,921. (see E. Ullrich, A. Philips, H. Seyberth) XXIII | (Az)575,228; (In)808,443. von Krannichfeldt, Heinrich. See V. Villiger. von Mering, Joseph F. ........ Se Sad eee Us ee aawe XXIV | Gm) 537,841; 541,489. (see E. Fischer) von Miuiller, Wilhelm. See O. Doebner. won mereer, Hugo ...<6e.00e- Aus.-Hng../Basle........ XXII | 348,483. von Portheim, Emil .......... PTO] 2 CY A rae epee VI_ | 498,303; 586,865. Czech... .. Kinzlberger... XXII | 1,404,055; 1,404,056. von Sztankay, Aba .......... Hung -{Chem. Found.| XIX | 1,357,482. won Werun, Max ............ Ger....... Hansmann... | XXII | 891,753. Voress, Clyde I. and Vernon Oe ge N. Y..... Gas. Rec XXII | 1,453,215. Vorlander, Daniel (see H. S. Holt and H. A Mle eal |Ger....... and Bruno Drescher ...... _|Ger....... Badische..... VII | 690,332. and Paul Seidel .......... Ger....... Badische..... VII | 778,725. Vorster, Walter. See J. Bani. mann. Voss, Arthur. See K. Schirma. cher. Voss, Robert. See A. Schmidt. Wacker, Leonhard ............ Geren fs'23 Badische..... VII | 549564. Wagner, Hermann and Jacob Lon oT ee gee Ger....... RlGchst%. . sac VI 1,082,719. and Josef Erber .....,.... Ger....... Hechst et. VI_ | 1:016,307; 1,041,919; 1,160,471. and Erwin Hoffa ......... Gera ts Hochst. tvs, <5 VI | 1,149,231. Wahl, Andre and Robert Lantz|Fr........ St. Denis XXII | 1:460,774. Walder, LOS eS ae Switz Sandoz...... XI | 1:299,070. Waldinger, Gustav A. ......... oe ee and Carl F. Iserloth ...... Cy) eee Bayer: 200. (Su)873,277; 882 : Waldstein, Martin E. ......... i> Eee wey sia aneanee and Armand Miiller ...... Wem rates « caus Seo oe XXIII | (Ab) 330,275. Walker, Harold W. See V. Coblentz. WHOL, BeGWatd [ovecs se wsewavees nee Kalinusiccs. +s XXIII} (Ox) 1,303,426. XXIV | (P) 1,337,673. Wallach Otto s5.cs esses ie ses (FOE vas = st ties ote eine VI vege ne Wetec, Roget Ne csc ccesscs oss haeux be reat oe XXII | 1,291,300. erage rob Ree hoes Ronee XXII | 1,470,039. BiterePOMANMES sles cs cece cs Witei cites CIC et ees vi 398,990; 1,297; 440,288. MO ETEUDS FIOPDET cc iccc ec aeess New vers YOUNBo or ses XXI mAh ye ables Warren, William H. ay R. W. Cornelison. MEN RIG diese iv s< 04s 09 6 Opa Ps el Peni tenor oe XXII | 848,791. Weber, Oscar. See W. Herz- berg. 38 574 DIGEST OF PATENTS COUNTRY DYE PATENTEE OR STATE ASSIGNEE GROUP PATENT NUMBERS Weber, Theodore .......0-00° Lilcdwe ness ee Geno see VII | 86,047. Wechsler, Marcus ..........-: Engs aoe oe Gillman...... XXI_ | 1,031,602. Weeber, Rudolf .......-...++- AUS SH nto e oo eeeaie XXIII | 1,186,052. Weil, Hugo . (see J. Schmid) .|Switz.....|Basle........ XVIII | 623,346. Weil, Leopold (see B. Mayer) .|Ger.......|.....ssceeeee XXII | 1,419,186. Weiler: lax, wcuisclssmtcsis sieve Gere ads Bayere..eaies XVIII | 891,888; 891,889; 947,876; 950,359; 976,417; 978,799; 978,800; 978,801; 978,802; 998,139; 1,004,609; 1,004,610; 1,093/0778 1,034,173; 1,044,836. Nav. see Synthetic..... XVIII | 1,101,770; 1,218,232; 1,244,149. Weinberg, Arthur (see M. Hoff- MANN) se eeeeeeveceececeees Geta ones Cassellas. 6.254 I 709,187. V_ | 395,300. VI : 380,067; 412,440; 421,640; 426,345; 515,100; 517,533; 525,245; 526,763; 532,125; 535,036; 535,037; 560,448; 560,449; 588,203; 703,105; 718,181. XV, | 896:5595 660,067; 701,435. 434,493; 469,329. XVIII | 464,538; 472,001. XXII 537,511; 651,061. and Richard Herz .2.....). Gere te Cassella...... XV 693,632; 693,633; and Felix Klingemann ....|Ger....... Cassellasin. ce VI 709,186. and Otto Lange <5... ..<>- Geri tuaess Cassellav-ne.- XV 712,747; 714,542. and Hans Siebert ......... Ger....... Casselia.. oor vI 375,848. XXII 362,560. Weisberg, Louis and Ralph S. ‘ IPOGteR Mieceters arcs civiciociete evade te eus IN setae Barrett. Gs XXIV (pl) 1,424,137. Weisbrenner, H. See D. Vor- lander. Weiss: Andre d5> .cosvack ve 2e8 oe Pegs oc Soc. Chim.... | XXIV | (£)1,345,649. Weiss, Franz, Cy). vam. eee Aus.-Hng..|Klimosch..... XXI | 443,026. Weiss, George H. and C. Dins- | MOHE See ie bom Vee aes Mass.....- Carter 0 oe XX_ | 384,804. Weiss Solin civics. ic teste ona stevetors NIGYc. Soct -Dparretts esse XXII | 1,301,796. ! and (harlea R. Downs. J. 1N.. Jisses« Barrett. 5.22% XXII | 1,318,631; 1,321,959; 1,322,983; 1,355,008; George C. Bailey, 1,374,695; 1,380,277. ) and Raiph oF. “Potter (soci Ni Ji... 0: Barrett... ¢s. XXII | 1,355,100. Weiss; Morris’. 92-027 ee Nueieowne Dovan-..ce XXIV | (pl) 1,422,506. Weissbrenner Heinrich. See D. Vorlander. Weith, Archie J. See IL. V. Redman. Weizmann, Charles, and David os yell far fds A Aone ei Pe BER waark cbpaliathrahetic’ XXII | 1,395,620. Welde, Robert. See B. Homol- ka, G. Merling, and A. Stein- dorff. Weller, Arthur W. and W. T. Ro) Bindleyi.. en ee Eng... 25 [eee ee eeeeeeee XXIV | (pl) 1,368,867. Wells, Alfred A. See C. Ellis. Wore buster. Fi SD beeen ei he a Poocein be Spares 5 aa ih meh (m) 563,993. eliz, | HHeitirich “(your eet ds Sen adische...5'. -754,264; 763,233; 825. Weskote Friedrich) See nicl ONO Ne ee Rumpff. Wessbacher, G. See L. H. De- hoff. Wie 7 une A eres oi a Coos bis! eainie ae goatee mane x 1,327,260. ite) “John> Mchoews. pte SS ¢ m)1,297,952; 1,313,657. Whitehead, William T. 7) 90>. Canada... |Dupee (1%4).. | XXIII 100,687. (Ab).499,6885 Whitty, George S.. /..5...--4-- NOV ae Devaeval sn) XXII | og3 764.0 0, Wichmann, George, and Max Gabler ou sans cone een eee Geri re ss st Chem. Fab... | XXIV (m) 690,804. (see A. Thiele) Wienall Harry. See J. Baddi- ey. Wildman ErnestvAce. eet Tndseecnee Parke, Davis. | XXIV | (m)1,317,250; 1,317,251. ee Otto. See B. R. Sei- (oar tias aA Crt Wilke, Rar)... sence annie es Gersente Hochst a. ane XXII | 1,417,875. Williams, wArthune Gennes Niecy nee Barretton doa. XXII | 1,423,980. PATENTEE INDEX 575 ————————————————_—_—_—_———=—==_—__============_——=_=_=_—=_=_=_=_=_=[_=[=[=[as_[a[{z™a”z=a_a_aa_a_a_a_—_——l__l__l_____—______—_—_>= COUNTR PATENTEE se a ASSIGNEE eke PATENT NUMBERS hs Woes a ea Re iercsisuere sets, weiss LIP attenerst Pigeons emeLaller. a... @OhiOneces ELUti terete ores tele XXII | 1,450,569. Williams, Rupert Ramer balsas 501 NY erageh ome ekelats eco ay VI |384,342; 304,425; 404,331. Alban yiners see VI |410,057; Re, 11,016; 410,058; 412,148; 412,149; 416,1453 te 11,178; 17,207; Re. 11,179. Witetter Richard .......... Gere ice ity bd and Petes Ditisherg <4.) Gere... «+s Bayer.......- XXIV | (m)1,427,506. Wilson, Edgar S. and E. Stew- DED ct sie el ctvigiece caieieis.c ss & © ENG ccle sce] we lowire swe 6 6 <0 XXII |640,061. (See L. P. Marchlewski) Wimmer, Robert (see P. Seidel)|Ger....... Badische..... XXIII | (1n)820,900; 833,654; 843,566; 910,889. Windisch, Kurt. See M. Bock- miuhl. WVitiicely SRLEPDETE es ccc c scene Dele. ees du Pont...... XXII | 1,307,570. Winslow, Homer ............- Rai Cassella...... XXIII | 941,399. Winter, Carl (see P. Julius) ../Ger....... Badische..... VI | 765,079. Winter, Poetigts i... ence esses Ger. ceces Hochst......- VI |697,765. Winter, Friedrich M. ......... Gf. ccs do eee ees esaeres XXIII | 905,264. Winther, Adolf, August L. Las- 5 : ka and Arthur Zitscher ..... Ger....... Griesheim....| VI | 1,034,853. Felix Kunert and Edwin } ; EE Re Sa ae (er Griesheim....| VI | 1,099,108. WA PR ESTUIRE cuca ioe ces ce ses 0% ee er Cree co eee XXII | 685,895; 714,428. Chem. Found.| XXII | 1,339,310. Wise, Louis E. See E. Q. dams. MV ISPAENIOTTIS, crises cose sss N. Y..... Jere cere seeee XXI |221,381. Witt, Otto N. (see H. Koech- y SN ees, iets os ss Ger....55. Badische. ...| Yr |381,045; 381,046; 420,372; 420,374. G@assellaunie. V 248,246; 249,136; XXII | 420,373. XXIII | (Az) 1,093,567. WoiterttGeG icc. i.e. cay, Elberfeld....- VI |761,1235 791,524; 791,525; 791,526; 842,048. eS Ger... .ceefeerr steer: XXII | 710,648. Wohlfahrt, Theodor. See M. Bazlen. Wolfes, Otto and Horst Maeder|Ger.......J-e-setseeere XXIV | (m) 1,419,092. oe ie Sere ect a Swit7ise ee |cumoe ous se VI |389,127. olff, Hugo (see O. Bally, : f BH. later a R. Just) Pee \Ganls. oe: Badische..... III |893,412; £95193: 1,063,000; 1,133,081. XV |1,054,888; 1,061,714. and Filip Kacer ......... Gee cits Badische..... III | 1,266,896. foie 92 CC. N. Y..... {Albany An... II 189,538. and Ralph Bertley ........ Rage ae TIT | 188,217. VI_ |277,182; 285,335. Wolffenstein, Richard ......... eT ae eae: tee e eee XXIV |(m) 1,063,099. and James Colman ....... erie: Berlin....... XXIII | (Ab) 1,019,576. Wollenberg, Harry L. ........ Wo aes and C. A. Bigelow ....... NiNi oc. . PCa ers sae. XXIV | (e) 1,297,524. Wollenberg, Waldemar. See R. Miller. Woltmat GC0WIk. occ acc ccase Ger neues Elberfeld..... DLE 72,S57. Payer a) vers: III |935,878. Wolpert, Ernest. See E. Hepp. Wolvekamp, Mari E. ......... Tee ae Abbotts eater XXIV |(m)1,361,128; 1,412,440. Woodbury, Clifford A. ........ iif eee ee da Pont... ++ XXIV | (e) 1,309,559. Woodruff, Theodore T. ....... Eee A ene Morris (%)..| XXIII | (In) 126,663; 126,664. Vee Se ET i oa | C: ee Héchst..... . | XXIII | (Su)907,937. Wray, Edward (see K. Elbel) . Ene Sarviers« Clauss. .casss XV_|1,247,475. re nee Kalle; 2.02.2.) VIL. 11,108,056;5" 1,108:087; ; 1,157,485. and Fritz) Peso ......+.-0> Ger. iiss: Wales ee VII | 1,144,577. UE, St | a res OTe e dns Hachette 55: VI |{1,056,080. (URN TEMNED Tiaig Dele iaiyse views os 0 ae GELo ciwisse's Hochst......- vI 1,154,826. Wiirgler, Jakob (see A. Grob _and G. Engi) ............ SwitzZic-. + | Raslew. 2s ee XI | 1,227,407. DM URERNCT MIT fc ccc cesses (Gere. Gieglest. oak ve XXIII | (Az)918,244. Wuth, Berthold and C. Jager- SE OE RE aoe pn a cs 0.4 vse « SWitzi.cns 4 Basledwo.. VIP® | 1,216, 8t2ecer. 2s saa3e 1,234,994; 1,216,760. Eugen Anderwert and B. : 4 4 CEES ine < és aces ne ssa'ss Witte. ss BasleGios cae VI 11,216, 760. 576 DIGEST OF PATENTS —————CC“LlllIl]lIl]_——sSss——ss—_—_—_—__S__=_S__=[=[=[[=[{j{aqa{=_={a~=—a=]E|[{=—=e={—=azEzqaEx{E—Eq{]{_—@_@_=[ee{{™{=x7xx=x=x=*=*=€#€—_c_=€—*{X{”__][=[=][[[S—[{_===a=_==@ COUNTRY PATENTEE OR STATE ASSIGNEE Wypbert, Ernst. See A. Gans and M. Hartmann. Wyler, Max (see H. Levinstein)|Eng...... Levinstein... ; British Dyes. Yarnall, Elizabeth S. ......... Morn tos ee cee eee Zacharias, Emil and Eugen Bernhard sop weve leeiieaiies cvwte Gef. . N. Y..... |Rumpff (14) Zitscher, Arthur (see A. Win- ther and A. lL. Laska) .....; Ger..... Fie) (eure yp wear Joe and Ernst J. Rath Geriteades Griesheim.... Felix Kunert and Edwin Acker ...... Getiandes Griesheim.... Zollinger, Ernst H. and Herman Roebling y 3 tres sacs s arse eres GEL dis sed (Glo ahe eaeeaton ts Lollner, ieMene” saca hy sae aa eo Get,; save Chem. Fab... Zublin, Heinrich and Adolf ZING a ower os ates eote sy Vier aeys Ltalviaee Schlaepfer. . vil XXII vI PATENT NUMBERS 1,358,490. 1,467,598. 846,887. 675,434. 999,944; 1,001,183; 1,012,960; 1,015,375 1,022,287; 1,022,288; 1,032,797: 1,114,844. (Ni) 1,031,823. 1,075,134. 207,093; 207,836. 90,417. 1,436,136. 324,630. (m) 563,116. (m) 466,708. 1,454,204; 1,454,205. (Tr) 76,031. 1, LOT, TEts 1,028,521; 1,066,777. 1,122,564. 11350, 472. (m) 1,086,881. (Az)601,420. a SCHULZ INDEX. This index is arranged in the same order as the 1914 edition of Schulz’ “Farb- stofftabellen,’ and the census of dyestuffs, 1913, “Artificial Dyestuffs Used in the United States,” by Dr. Thomas H. Norton. The names are those first mentioned by Schulz. For a complete alphabetical name index of dyes, reference is made to either of the above works.* Patents corresponding to some Schulz numbers have not been filed in the U. S. Patent Office, and some patent numbers in Schulz were found to be incorrect. Numbers in ttalics are patents of homologous or closely related dyes and are indicated in the abstracts by words “Near” or “Homolog of” preceding the Schulz number. Further references at the bottom of each abstract will also aid in the location of dyes closely allied to those reported by Schulz. Mineral and vegetable dyes have been omitted in this index, as there were no corresponding patent numbers. N ba = Fs NAME | Patent No. 36 NAME Patent No. By4 Bis n Group I.—NITROSO. (Abstract, Group X.) tieolid Green O........ | | FUR eicdadd ee gias'e x | BOGAN oh ape ede ss 4|Naphthol Green B ...] 316,036; 362,835. Group II.—-NITROSO. (Abstract, Group IX.) Oa aS ee 300,874; 666,627; 6|Martius Yellow ...... 1,200,171; 1,349,802; 7|Naphthol Yellow S ...| 225,108; 289,543; 1,380,186; 1,396,001; ; ; | 324,615. 1,413,914. 8|Pigment Chlorin GG .} 763,756; 955,080; Group III—STILBENE. (Abstract, Group XIV.) ojSun Yellow ......... 360,553. 14|Diphenyl Chrysoin G .| 951,046. 10o|Mikado Yellow ...... 15|Chicago Orange G ..| 601,063. 11|Mikado Orange ...... 395,115; 396,527. 76/Curcuphenine "2. .....- 951,046; 951,048. 12|Diphenyl Citronin G .| 613,911. 17|Chlorophenine Orange. 13|Polychromin B ...... 455,952; 636,065. 18|Diphenyl Fast Yellow. Group IV.—PYRAZOLONE. (Abstract, Group XII.) 19|Flavazin L .........-. 24|Pigment Fast Yellow R| 935,370. BOVPIAVEEIN GS ci ve sw sens 25|Dianil Yellow 3 G ..]| 658,593; 662,056. 21|Pigment Chrome 935,829. 26|Dianil Yellow R ....| 656,857; 679,172. PINS ciple os we ss 27|Dianil Yellow 2 R ...| 656,858; 656,859. 22|Xylene Yellow 3 G ...| 901,675; 982,050; || 28|Pigment Fast Yellow G| 731,670. 984,900. 29|Eriochrome Red B ...| 808,919; 1,026,257. 23 TAGtlazin 2 ce cdesas 324,630; 627,690; || 30|/Radial Yellow G .... 935,830; 969,428; 972,951; 1,010,919; T,096,600 ; 1,447,485. Group V.—AZO. (Abstract, Group VI.) Amidoazobenzol ...... 27, \Ovang Gn lug nests 37 \ Butter Yellow ......- 48|Alizarin Yellow GG...| 424,019. 33(Chrysoidin ........++- 49|Prague Alizarin 34|Chrysoidin R ........ 221,120+ Yellow G ......005. 528,965. 35|Sudan G .....+eeee- 50|Azo Cardinal G ...... 36|Sudan I .......--+-- 51|Nitrophenine ......... 37|Ponceau 4 GB ......- 52|Archil Substitute ....| 211,525. 38|Orange G .....------ 251,162. 53|Archil Substitute 3 VN} 380,928. 39|Ponceau G, 2G ..... 251,162. 54|Apollo Red B, G ..... 376,392. 40|\Chromotrop 2 R ....| 458,283. 55|Brilliant Archil C .... 41|Fast Acid Fuchsin B. 56|Paranitranilin Red ...] 211,525; 598,118; 42|Amido Naphthol Red G 601,420; 724,743; 43|Tolan Red B, G ..... 563,383. 728,388; 728,455. 44|Azo Archil R ........ 57|Chromotrope 2 EAA) Paeebekeer 45|Brilliant Lake Red R . §8|Alizarin Yellow R ....] 431,297. 46|Metanitranilin Orange.! 557,228. 590|Wool Violet S .....- 525,656. * A more complete list of names of dyes may also be found in the Colour Index, published by the Society of Dyers and Colorists. This work is so thoroughly cross-referenced to the 1914 edition of Schulz that no difficulty can be experienced in using both publications in conjunction with the digest of patents. NAME Grove V.—(Continued).—AZO. ~60|Azo Phosphin GO ....| 626,913... ~~*{| 128|Janus Gray B, BB ..| 613,920. — 61|Victoria Violet 4 BS. 62|Azogallein . 3... tse. 63|Azo Acid Blue B .... 64|Azo Acid Red B ..... 65|Azo Coralliny Loic... s 66|Amido Naphthol 1 Red? Gas oct s as slChneuetrade OB rere 68|Spirit Yellow R ...... 69|Chrysoidin Rss... +s 70|Brilliant Orange O . 71(Azo Fuchsin Bo...) .; 72|Pigment Orange R ... 73|Pigment Fast Red HL 74|Tannin Orange R .... 75|New Phosphin G .... TOV Oud a ce Late sicele as heiibe 77\|Azo Coccin 2 R ...... 78|Cochineal Scarlet 4 R. 79|Brilliant Orange R ... cg ithe Scartet Roo Fst; sri pautin Scarlet Attn: $2) Ponceau e2u kk veces cre 83|Ponceau 3 R, 4k. 84| Azo Chromin ..... arene 85|Omega Chrome (oi DISCICURN tac oc a tae. BOUACErIN, Oto. «+c sh. els 87|Peri Wool Blue Bo Ae 88|Acid Anthracene {SOTO WH Gk Aes ae Serene 89|Metachrome Brown B. 90/Chrome Brown ...... 91|Anthracyl Chrome CsreenmeAtrocs oe cet “ deaux R OF sudan Ramee Scene ee 94|Azo Eosin G . 95|Azo Cochineal ....... 06 Chrome Fast Yellow GG ....08. 07|Chloranisidin Scarlet . 98|Naphthol Rose ....... 99|Tuscalin Orange G . Z00|osamin (Be... = eee go1!}Coccinin (By On... oe 102| Diamond Flavin G. 103|Holland Yellow 104|Benzoyl Rose ....... tosjsudan Brown ....... 106|Carminnaphth Garnet. 107|Sulfamin Brown A . 108|Double Ponceau R .. 109] Palatin Red. A... 2. 110/Buffalo Rubine ...... 113 | Fast. Réed (BR oh is, ri2\ Fast Red -B Se 2.0. 113|Crystal Ponceau ..... 114|Chromotrope 10 B . 115|Azo Turkish Red .... 116|Sulfamin Brown B .. 17 erika eG Noah cee 118|Geranin 2.B, Gils... 119|Diamin Rose’ Re eee, 120|Salmon: Réd.... 20.00% rc Brika Bary er aeeo 2g rika Goes) eee eae S25 Rinna Red ee cate ek 124|Diazin Green S ..... 125 Diazin Blackwwevaloene 126|Indoin Blue R ...... 127|Methyl Indone B, R. DIGEST OF PATENTS Patent No. 626,913. 792,032. 567,615. 7975732. 941,088, 718,181. 217,071: 466,841; 500,761. 515,100. 515,100. 201,671; 268,113; 268,113. 268,113. 268,113; 456,627. 268,113. 210,233; 251,163; 548,460. 841,371. 302,790; 306,546; 827,468. 657,064; 658,507. 987,362. 664,055. 704,825; 213,564. 213,563. 695,812. 982,952. 945,780. 204,799. 204,799. 204,709. 251,164. 332,528. 911,185. 535,037. 418,657. 524,251; 468,142. 268,113. 456,897. 333,035; 268,113. 268,113. 303,335; 306,969. 657,065; 704,826. 524,252. NAME (Abstract, Group VI.) 128| Janus, Gray 1B, 3B Be 129|Chromazone Red ca oo 130|Chromazone Blue R . 131|Permanent Orange Be al ee Red By vaverereisvets 133|Eriochrome Phos- Din ptvieeesy. ele aie ae 134 Metanil Yellow ...... 135|Brown Metanil Yellow 136|Acid Yellow MGS .. 137| Fast, Yellow Geis. => cise 138|Helianthin 139 |Orange) LV it. se sree tTa0\Azohavin RS) a eee 141|Azo Yellow 3G ..... 142|Brilliant Yellow S . | | ae eeoeeeseeres 144|Orange I. o.cse see 1745 |Orange lI. ances 146|Azo Fuchsin G ...... 147|Azo Fuchsin 148|Fast Orange O ...... 149|Fast Yellow Y ....... 150|Fast Yellow N ...... 151|Orange T oe 152|Lithol Rubin B ..... lens Red: Cis caries | 154]Acid Alizarin Brown B 155|Acid Alizarin Garnet R 156|Acid Alazarin Violet N 157|Diamond Black PV .. 158|Chrome Brown RR .. Ebi a> Alizarin Black R 160|Naphthylamin Brown. 161| Fast Red Anjan ee 162|Brilliant Fast Red G . 163|Azo Rubin .....00seae 164|\ Fast (Red (V Ries tere Azo Red) Avaee cesenet 1661 Fast] Red) Ey yayee eee 167|Crocein Scarlet 3 BX. 168| Amaranth 169|Cochineal Red A ..... 170|Ponceau 6 R ........ 171|Chromotrope 8 B .... 172|Fast Brown 3 B ..... 173) Lithol (Red Roose 174|Double Brilliant |. Searlet. /..5:0.nenenenee 175|Ponceau for silk, G .. 176|Double Scarlet Si eee 177|Chrome Yellow D ... 178|Crumpsall Yellow .... 179|Lake Bordeaux B . 180|Eriochrome Blue Black? Bii.s%. anes 181|Palatin Chrome Black:'6:=Bo ex vives 182|Fast Sulfon Violet ... 183|Eriochrome Black T . 184|Eriochrome Black A . 185|Anthracene Chrome |. Black (chop eeareeene Lanacyl. Violet Biize.. 187|Lanacyl Blue BB .... 188/Tolyl Blue SR ...... 189|Sulfon Acid Blue B . 190|Alkali Brown ........ Pyramin Yellow R .. Cotton Orange G 165 186 IQI r27 srethy! tndone DB. KR...) ite 192|Cotton Orange Go epee o ee Patent No. 613,920. 688,647. 714,882; 932,289. 991,750. 210,054. 253,598. 210,054. 210,054. 210,054. 210,054. 210,054. 466,841; 833,605. 714,883; 253,598. 741,020; 733,280; 759,716; 983,486. 628,814; 692,675; 727,967; 548,460. 654,064; 667,935; 741,552; 204,799. 204,799. 204,799. 204,799. 256,376. 314,938. 268,506. 332,829. 650,757; 332,820. 690,294. 332,829. 555,058. 858,065. 806,415; 779,177; 790,364; 640,989. 790,363. 656,120. 524,262. 921,239; 468,142; 888,981. 743,071. 752,562; 765,080; 647,230. 727,962; 729,001. 654,065; 672,714; 933,842. 718,356. 835,539. 778,476; 807,422. NAME Schulz No Group V.—(Continued).—AZO. 193|Clayton Cloth Red ...| 404,097; 194|Rosophenin 1o B .... 195|Rosophenin SG ...... 398,990. 106, \itan Rose 3 B ...... 197|Thiazin Red G ...... 398,990. 198|Clayton Yellow ...... 428,629; 446,009. 199|Oriole Yellow ....... 398,990. zoo;wake Red D......... 878,964. 201|Pigment Scarlet G .. 837,128. 202|Acid Alizarin Red B .| 757,109. 203| Yellow, soap fast ....} 297,852. 204|Diamond Yellow G .. 205|Diphenyl Chrysoin R R| 644,462. 206|Diphenyl Catechin G .| 644,462. 207|Diphenyl Fast Brown Ev ECan a 644,462. 208|Leather Brown ...... 200\lérracotta F ........ 440,288. 2z10|Cotton Orange R ....] 524,261. 211|Resorcin Brown ..... 260,359. 212|Fast Brown G, GR ..| 741,936. 233iFast Brown .:....... 214|Fast Brown O, NT 2rsipiie Black Noo... .. 563,384; 216|Domingo Blue Black B| 606,438. 217|Naphthol Blue Black S| 480,326; BG NIWWTOphOr 2), 6s ae as 219|Chrome Patent COTREHOIN a Su hectic 220|Palatin Black A ..... 590,088; 683,120. 221|Anthracene Acid AS TOMER Wrsiieie.6 wie tower lol's 222|Janus Yellow G, R ..| 623,697. Poe iol hee)? 224jCioth Red G’........ Zaeierocemm AZ: ........ O20 Crocein “Bis. vac... 333,0375 227|Brilliant Crocein M ..| 233,465; 228|Ponceau 5 R ........ 268,507. 229|Azo Acid Violet ..... 230|Cloth Red 3G ...... agree Red 3B ....... Sepp MtIeE Vi hi Ss. es as 233/Cloth Red B ........ aga; clote ned G........ 863,396. BES TOCOIINS Bo oc euis ese 333,035. asoi\Cloth Red B ........ 578,432. gaol mordeaux BX ..../.... 238|Union Fast Claret ...] 246,221. 2aolice Black ..........; 586,865. 240|\Janus Red B ........ 623,697. 241|Neutral Gray G ...... 242|Sulfon Black G, R ...| 498,404. 243|Coomassie Wool ..... PEIRCE ERE 6 6 coal « v0 654,167; 244|Coomassie Wool OU 654,167; 245|Nyanza Black B ..... 491,410; 52,107. 246|Cloth Scarlet G ..... 247|Double Scarlet ...... 224,927; 246) Past Scarlet B ...... 224,927. 249|Crocein Scarlet ...... 256,378; 250|Milling Orange ..... Pa 251|Crocein Scarlet O ... es 2sz2iCloth Searlet R ..... : B2ss/Orsetllin BB ........ 254|Bordeaux G ......... 255|Crocein Scarlet 8 B ..| 256,375. 266) Sulfon Black ........ 257|Sulfon Cyanin G .... 258|Naphthalene Acid By a ge lee sae aTa)'oh Sroeonceat 16 RB ..\...< Rie LO, 260|Eriochrome Verdon A 261|Buffalo Black 10 B ..} 618,963. Patent No. SCHULZ INDEX NAME No. (Abstract, Group VI.) Victoria Black Bee. a. 441,945. || 262 203) etm lackn Ramrauitesene« 425,885 264|Fast Sulfon Black F . 265|Sulfon Cyanin Black B 266|Naphthylamin Black D} 412,440. 440,281; || 267|Anthracite Black B ..] 502,912. 268|Naphthyl Blue Black N 269|Naphthol Black 6 B ..{| 345,901. 270|Brilliant Crocein .... 271|Diamine Blue 6G... 272|Naphthol Black B 345,901. 273|Diaminogen Blue BB . 274|Diaminogen B ....... 533,463; 29,74 275|Diamond Black F ...] 438,438. 276|Diamond Green B . 438,438; 277|Anthracene Acid Black 278|Biebrich Patent Black] 476,070; 546,069; 279|Benzo Fast Scarlet .. ia oie 97,705; 280|Azidin Fast Scarlet} GGS-7 45... 281 cater! cl en Garlel de Does saan $23,058. 282 wet Fast oe: cafletyp ison. ses 557,440. 283|Bismarck Brown ..... BOA WIESU Viti ee Liauemeteretett mes 285|Toluylene Brown G ..| 516,380. 593,790; 286|Toluylene Yellow ....] 568,540. “*"" || 287|Toluylene Orange RR] 497,032. 288|Acid Alizarin Black ..| 665,696; 692,676; 289|Acid Alizarin Black ..| 677,227; 290| Violet Black ........ 291|Azo Alizarin Bordeaux] 631,089. 292 Sane as Ailes I .| 628,721; _ || 293| Milling Red G ....... er heey 294|Anthracene Yellow C. 295|Diphenyl Fast Black .| 525,245; 296|Cotton Yellow G..... 430,535. 297|Benzo Fast Rose 2 BL| 678,323; 298|Milling Red R ....... 299|Cinnabar Scarlet BF . 300/Cotton Ponceau ..... 301|Hessian Purple N ....] 350,230. 302|Brilliant Hessian Purples. eee ee 350,230. 303|Brilliant Yellow ..... 350,229 304|Chrysophenin G ..... 395,115 305|Hessian Yellow ...... 350,229 306|Pyramin Orange 3 G .| 631,610 307|/Congo Red .......... 365,667 308|Diazo Black B ....... 309|Glycin Red .......... 654,168. || 310|Glycin Corinth ...... 498,303. sii~Orange TAs ockaees 654,168. || 312|Congo Corinth G ....| 344,971; 511,688; || 313|Congo Rubin ........ 314|Pyramin Orange RR .| 631,611. 315|Congo Orange G 454,840; 224,928. || 316|Brilliant Congo G ... 317 Eiiemidel own BG.| 361,404. 318| Benzidin “Puce |... 35 bees ecers ene 219| Diamitz Scarlet Bo...’. | 2 426,945% 9° 9 9 9 tb go] Bordeaux CGV 0,.,2,)6¢ © 2 > 2 oe oo 32 Sboliotrope 2°32..." 322|Trisulfon Violet ..... 584,981. 323|Dianil Blue R ....,,. 4 324(Chicago Blug 4 R .2 9). ; » 325 /Columbia Biyre Ro es ‘ 426 0Oxamin >Yiolet 22.2.2..7 527,090; 327|Diamin Violet N .... 328|Diamin Black RO ... 329|Diamin Brown V .... 320|Zambesi Brown G, GG 579 Patent No. 560,796; 464,775. 546,068; 546,070. 663,498; 1,015,375. 677,231; 693,670. 680,283. 640,010. 575,904. 687,171. 358,865. 563,384. 724,893; eer a ee ee en ne ee ee an 580 DIGEST OF PATENTS N 3 NAME Patent No. 36 NAME Patent No. 52 Sz, n Group V.—(Continued).—AZO. (Abstract, Group VI.) 331|Alkali Dark Brown GV| 611,111. 400|Milling Scarlet 4 R. 332|Dianil Garnet B ..... 842,048. 401|Diamin Blue 3 R ot 380,067; 588,203. 333|Diamin Black, BH ...] 501,500. 402|Diamin Blue Black E. 588,203. 334|Diphenyl Blue Black . 556,164; 567,413. || 403|Diamin Black BO . 442,369; 588,203. 335|Naphthamin Black RE 563,386. 404|Diamin Yellow N ....]| 308,067. 336|Benzo Cyanin R ....| 499,198; 533,508. a Benzopurpurin 10 B .| 357,274; 481,934. 337|Diamin Blue BB ..... 464,135; 544,699; 6\Diazurin ib eo. eae 544,700. pi Azo Violets)... Gann’ 447,302. 338|Naphthamin Blue 2 B.| 563,385; 563,386; || 408|Dianisidin Blue ......] 525,492; 569,392; 606,181. ; 575,228. 339| Brilliant Orange G .. 409|Trisulfon Blue B ...| 584,981. 340|Benzo Orange R ... 447,303. 410|Benzoazurin G ...... 481,934. 341|/Crumsall Direct Red.. 447,303. 411|Benzoazurin 3 G..... 357,273; 388,185; 342|Chrysamin’ G: 0). 3..34 320,638; 329,630. 481,934. 343|Diamin Fast Red F .. 412|Congo Biue'2 B yess 467,162. 344|Diamin Brown M ....]| 535,036. 413|Direct Violet BB ....| 524,060. 345|Oxamin Maroon .....} 558,344. 414|Indazurin B_........ 524,069. 346|Oxamin Red ........ 555,359; 666,867; || 415|Dianil Blue G ....... 679,974; 724,894. || 416|Brilliant Azurin 5 G . 347|Diphenyl Brown RN .| 567,413. 417|Chlorazol Blue B ... 348|Diphenyl Brown BN .| 567,413. 418|Diamin Brilliant Blue 349|Diamin Brown B .... Ge. wa eee 512,493; 532,1255 seal Alkalt Yellow R ..... Wal 535,037. 351|Cresotin Yellow G ...| 394,841; 396,294. |] 419|Chicago Blue RW ... 352| Direct WVaolet Ri. 527,070. 420| Azidin Wool Blue B . 888,036. 253|Direct Indigo Blue BN| 525,626; 536,878; || 421|Oxamin Blue B ...... 558,344. 557,438. 422|Chicago Blue 4 B ... 354|Direct Gray R ...... 493,504; 525,626. || 423|Chicago Blue B ..... 355|Anthracene Red ..... 493,583. 424|Chicago Blue 6 B ....| 511,532. 356|Dianol Red 2 B..... 594,123; 625,174. || 425|Benzocyanin 3 B .... 533,508; 578,432; sesiDianct Li Wh . 442|Direct Black V_...... 601,033. 38e(Dianil’ Blue Boon. 443|Direct Indone Blue R| 601,033. Leb ne: Black Blue B, R| 468,040. ah Cope boa ee: 382!Azo Mauve B ....... poe neal 462,824; 445 Crumpsall Direct 9 282!Naphthazurin B ..... 608, ; Brown O ....... «+ 622,065¢ 384!Chicago Blue 2 R'....| 888,036. ppratbemarrrnde i 479,515. 285|Oxamin Blue 4 R ...|{ 521,095. 448|Diarnt Bee Gin 476,393; 503,148. 384!Diamin Blue BX ..... 498,873. 449/Trisuifon Browa B cite aad 387|Columbia Rlue G . ceo Bene BI k Blu Rr. 608,024. 338] IeHicee Blue TR wc... |, $26,284; $09,929. pie chao Sant Blue Bt 39" Ebol: | lue B oa re bac) +} Shores O06:4273 § 452|Renzo Indigo Blue ..| so1,118; 602,856. Pe Shanice st ae ‘|-453f Colustbid ‘Black R .++| £76,604, 3901 Benzbéyaain: Bi woe < 333,503 5 ‘5783423. 4) 454|Trisutfon: Brown G ..| 608,024. 391/Diamin Blue 3 B ... 521,985. 455|Columbia Black B ... 392| Toluylene Orange | Cie -| (375,930; 395, 634. 45.6|Congo Fast Blue B .. Sas tDiohedy Brown 3 GN 5875413. ce 2 |. 45%|Trisulfon Brown GG .| 608,024. 394|Chrysamiay Re x. 8 iy 329.6487, “Aor, 0242 452] Carbon Black | Gene 395!Cresotin Yellow R' ‘ 364,8115 «<<< « » |h4g¢|Benzo Black Blue G . 396|Indazurin RM ....... 524,070. 460|Benzo Black Blue 5 G 397|Direct Blue R ....¢.. 493,504. 461|Coomassie Union Black} 619,104. 398|Direct Gray B ...... 462|Erie Direct Black GX.| 515,381; 688,478; 3golIndazurin TS .......) 524,070. Ne SCHULZ INDEX 581 N N Z Pe) NAME Patent No. iS 3 NAME Patent No. 4 OG mn 2 Group V.—(Continued).—AZO. (Abstract, Group VI.) 463|Erie Direct Black RX.| 688,478. 478|Columbia Green ..... 464|Erie Direct Green ET.| 688,478. 479|Dianil Black R ......] 582,958; 582,959. 465 cy ne Black 480|Congo Brown R ..... 572,723. Gre Dre sal e's ‘aviovuite 481| Azo Corinth Giceocss sc» 516,381. 466 Eboli ae CW, "etc.. 606,436; 606,437; || 482|Alizarin Yellow FS .. 606,438; 606,439. || 483|Rouge de St. Denis ...}] 483,368. 467|Diphenyl Green ......| 628,233. 484|Milling Scarlet B ....] 483,368. 468|Diphenyl Green 3 G..| 628,233. 485|Benzo Brown G ......] 384,315. 469|Chloramin Black N .. 486|Direct Brown J .....| 491,422. 470|Chloramin Greeen B..| 627,679; 652,456. || 487|Benzo Brown B ...... 471|Chloramin Blue 3 G..| 652,456. 488|Toluylene Brown R ..| 465,116; 683,190. 472|Chloramin Blue HW.. 489|Hessian Brown BBN.. 473|Diamin Black HW ... 490|Cotton Brown A, N.. 474|Diamin Green B .....| 628,233. 491|Dianil Black PR ....| 576,203; 578,580; 475|Diamin Green G ..... 514,599. | 644,292; 832,393. 476|Benzamin Brown 3 GO 492|Anthracene Acid 477|Congo Brown G .....! 399,581. BEownu. Die comes «cot Group VI.—AURAMIN. (Abstract, Group IV.) AGP OMTAMIN 5 ccxcmwsovsse| 301,802; 720,920. so4| Sura Gre wegsecenel -Q0S,A30) Group VII.—TRIPHENYLMETHANE. (Abstract, Group XVIII.) 495|Malachite Green ......| 222,257. 535| Methyl Alkali Blue ... 496|Setoglaucin O . 536|Alkalt Blue R, B..... 497|New Solid Green fs 3B 537|Methy! Blue for Silk .| 333,86r. 498|Turkish Blue B, BB . 541,572. 538|Methyl Blue for Cotton] 538,215. 499|Brilliant Green ....... 539|Water Blue ......... 538,215. -500|Setocyanin O ....... ; 540|Pacific Blue ......... sorjGlacier Blue ......... 525,627. 541|Brilliant Dianil Blue .. 502|Guinea Green B ..... 542|Agalma Green B ....| 886,815. 503|Night Green A ...... s43iPatent Blue V ......1| 432,613; 412,614; so4|Light Green S F, | 412,615; 519,971; Gls SS eae 266,912. | 647,834. 5s0s5|Light Green S F, Baa CYaTIM TD) scala Sate ao ee 463,898. oS ee g45\Patent, Blue A .. 412,613 506|Erioglaucin A ....... 564,801. 412,615; 422,018; 507|Xylene Blue VS ..... 538,027; 709,160; 567,567. | 731,139. 646/Cyanol FR acco. 8 .-| 472,091; 567,567. 508|Xylene Blue AS ..... 583,267; 615,485; || 547|Ketone Blue 4 BN .. | 673,632; 731,139. || 548| Acid Violet 6 BN ...] 501,434. so9|Chrome Green ..... ..| 502,104. 549|Chrome Violet ....... 476,414; 478,005; sroj|Azo Green .......... . | 501,104. s11|Para-fuchsin ......... 550|Chrome Bordeaux .... Sia/Puchsin ............. 50,335; 53,241; || 551|Eriochrome Azurol B.| 877,053; 887,620; 2AS,1543 6252,202% | 950,359; 978,800; 283,766; 310,128. || | | 999,028 ; 1,042,493; 513|New Fuchsin O ......| 47156383 473,453. | 1,244,149. SravRemevaolet S Ro oiee ss 43,066. 552|Chromate Blue G ....| 877,054; 980,251; 315|Methyl Violet .......| 325,828. Riel 999,028; 1,042,493. 516|Crystal Violet .......| 299,856; 290,801; || 553|Eriochrome Cyanin R.| 877,052; 947,876; 290,892; 329,636. 999,028 ; 1,042,493. 517|Methyl Violet 5 B....| 297.415; 297,416. ||554|Chrome Azurol S ....] 877,054; 999,028; 518|Ethyl Violet .........| 299856; 290,891; | 1,042,493. 290,893; 325,827; ||555|Aurin ...... Bangee cs 978,799. 329,637. 556'Red Corallin .........| 307,40%; 316,471; s519|Methyl Green ........ | 318,484; 333,649; 520|Light Blue, spirit sol..| 252,203; 327,953. | 589,766; 591,309; g21|Spirit Blue .......... 32,965; 248,153. | 609,598; 995,494. 522|Victoria Blue 4 R....| 308,748. 557|Chrome Violet .......| 410,739; 603,300; 523|Fast Green, bluish ...| 4233413 498,471. ber cies 609,599. Sea, Pucesin 5, SN ....... 250,201; 250,247; || 558| Victoria Blue R .....| 517,473. 262,680; 421,049. || 559| Victoria Blue B ......| 297,413; 207,414; S25 Ready Violets RS ..... 204,797; 204,798. 496,435; 658,504; 526|Acid Violet 4 RS ....| 294,797; 204,798. 684,457. 527|Acid Violet 4 BN ....| 331,964; 331,965; || 560|Night Blue ...... eoee| 647,260; 658,504. é 580,186. 561|Acid Violet 5 BNS ..]} 603,016. 528|Fast Acid Violet 10 B.| 501,069; 580,186; || 562|Fast Acid Blue B ....| 506,918. 611,628. 563|New Patent Blue B ..| 605,119. s29!Acid Violet 6 B...... 564|Naphthalene Green V..| 628,243; 630,224; 530|Acid Violet 6 B ......| 707,813. | 639,976; 639,977. 531|Eriocyanin A ........| 464,538. s6s(Acid Blue B ........ 603,016. 532|Alkali Violet 6 B . 340,022. 566| Wool Green S .......| 897,888; 891,889. 533|Acid Violet 7 BN ....|] 353,264; 353,265. || 567) Wate Blite. «vcecsee| 476,483; sza4\Acid Violet 7 B...... 353,266 DIGEST OF PATENTS N N = 6 NAME Patent No. E S NAME Patent No. Zr \[o Z iA WY } Group VIII—XANTHONE. (Abstract, Group XIX.) SOS) PivirOninwe Gueeee cee ae 445,684. sSellratiin Meee eles ene KROQ Acridin Red Bunce. s 586(Chrysolint -'sol Saiceeeeeen covet 290,585; 800,588; 612|Quinolin Yellow, sp. . | 1,197,632. SO) Scctureteioneia te eraikecaterats 290,585. | Group XI.—THIOBENZENYL. (Abstract, Group XVII.) 614|ChrominvGitysoes ae 617|Chloramin Yellow 615\lhioflaviniio eer s,« 412,979. C,. GG nb. Sees | 656|\Primulingtea seme csi nce: 406,952; 415,359. 618|'Thioflavin TT cise cab emi aes ovion Group XII.—INDOPHENOL,. 619|Indophenol 261;5183) 263;341. eeeeeeeeosn Grove XIII.—OXAZIN AND THIAZIN. 620|Capri Blue GON ..... 494,838. 621 |(Cresyl= Blue tm. 4.5 oie : 622|Delphin Blue B ...... 897,619; 936,247. 623|Pyrogallol Cyanin sulfo| 898,039. 624|Modern Violet N ... 863,907. £20|Galloey. Heliotrope ...}| 707,832; 898,040. 626|Gallocyanin DH ..... 25457215 257 .4OO8 366,357. 627 aiadess Cyanine sera: 844,156 628|Gallocyanin MS ...... 444,538; 534,809. 629|Gallo Green DH ..... 807,182 630|Gyanazurin i csras ns 929,350 631|Chromocyanin V .... 613,578; 638,576; 1,188,259 632|Ultra Violet LGP ....| 901,657. 633 )Indalizarina Ry jp os see 613,578; 662,224. 634|Indalizarin Green .... 635|Blue tooo TC 3..é92. 629,666; 962,712. 636|Prune pure ...... nes = 890,57 4- 637|Gallamin Blue .......] 410,733; 842,303; | 893,855; 902,154. 638|Amido Gallamin Blue.| 898,842. 639|Gallanil Violet R..... 420,164; 440,359; 451,502; 1,268,455. 640|Modern Azurin DH ..| 898,008; 1,268,455. 641|Corein) RRViy..a. 5.28 518,458; 534,809; 842,303; 895,635. 642|Phenocyanin VS ..... 547,173; 707,833. 643|Phenocyanin TV ..... 585,934. 644|Ultracyanin R, B .. 616,622; 992,613. 6asiGallaziny cameecee ee 531,148. (Abstract, Group VIII.) (Abstract, Group XI and XVI.) 646|Corein AR ...... cps [Mea Bee 647|Nitroso Blue MR .... 648|Iris Blue lia... eave vee 649|New Blue R ......... 252,273; 413,562; 454,535. 6so| New, Blue” Bree ae 651|New Methylene ls Blue’ GG" says aes 442,680 652|New Fast Blue F, H .| 499,243. 653|Nile Blue A ........ 404,309; 431,541. 654|Nile Blue 2 B.c..en. 655| Muscarin= sees ace 413,562. 656|Alizarin Green G ....] 548,158. 657|Alizarin Green B .... 6s8| Fast. Black Ayes 659|Methylene Blue B ....] 204,796; 246,327; | 270,311; 323,514; | 362,592; 366,639; | 366,640; 384,480. 660|Methylene Green O .. 661|Thionin Blue GO ....| 362,592; 366,639; 366,640. 368,716. 662| Thiocarmin Ries. 434,493. 663|New Methylene Blue N]| 469,329. 664|Leuco Gallothionin DH} 842,303. 665| Urania’ Blue’ 3.22 .. ove} 607,408. 666|Indochromogen § ....] 524,322. 667|Brilliant Alizarin Blue] 522,897; 524,322; 538,183; 560,795; 606,212. NAME Patent No. Group XIV.—AZIN. 668|Flavindulin O, II ... 543,784. 669) Neutral “Violet ....-.. 248,246; 249,136. G70) NeutraledRed as a0 oc os « 249,13 671|Indulin Scarlet ...... 533,829 O72\Azocarmin» Ge....<..-| 428,530; 430,975; 431,404; 466,852; 524,222. 673)Azocarmin B-........| 466,826; 567,473. 674|Rosindulin 2 G ...... 443,408. 675|Rosindulin G....... ‘ 443,408. 676|Neutral Blue ........ 677|\Basle Blue R ........ 360,764. 678|Fast Neutral Violet B.| 248,246. 67 Oatranin A i. oes 02 palee}i O25 120. py a panes Violet”... 681|Methylene Gray O ...| 420,311; 636,626. GselNigtamin ys ca. 2st eas 683|Safranin MN ........ 684|Rhodulin Violet ......| 543,894; 557,022; 559,062; 559,063; 592,608. Group XV.—SULFUR. 706|Cachou de Laval .....{ 897,873; 909,151; 909,1555 1,244,795; 1,244,796. 707|Sulfin Brown ........ 708|Sulfanilin Brown 4 B.| 687,581; 909,151. 709|Italian Green ........ 710|\Immedial Yellow D ..| 561,277; 712,747. 711|Immedial Orange N...| 641,954; 714,542; 895,037; 896,916. 712|Kryogen Yellow G ...| 773,346. 713|Thiophor Bronze 5 G. 714|Thiophor Yellow BLONZee neck ccs cues 715|Thiocatechin .........| 561,276; 687,072; 738,027. 716|Kryogen Yellow R ...| 773,346. 717|Vidal Black I ...... «-| 532,484; 532,503; 594,105; 653,278. 718|St. Denis Black B ....| 646,873; 740,465. 719| it hional “Black ....... 720|Sulfur Black T ...... 618,152; 655,659. P2Tloulturs Diack. 5.6.4 722|Auronal Black N ....| 606,193; 1,026,881. 723|Autogen Black EEB ..| 904,224. 724|Immedial Black FF ..| 610,541; 628,607; 628,609; 635,169; 639,806; 642,256; 650,293; 651,077; 667,689; 692,174; 695,835. 725|Immedial Dark Brown A e@eoeoeveeveee 596,559; 647,846; 660,058; 660,067. 726|Pyrogen Direct Blue .| 665,726; 775,570. 727|Auronal Black B .....| 764,733; 764,734; 764,735- 728|\|Immedial Pure Blue ..| 653,670; 693,632; | 693,633; 693,634; Grove XVI.—ANTHRAQUINONE. SCHULZ INDEX 583 iN SS NAME Patent No. et OG (Abstract, Group V.) 685|Tannin Heliotrope ... 686|Amethyst Violet ..... 687|Rosolane O ..... ties 688|Rosolane ..... ae beels HaoiPhvokvA~re Nik Ae eemae 395,300; 578,093. 690|Diphene Blue R ..... 511,653. 691|Metaphenylene Blue B] 395,300. 692|Naphthazin Blue ..... 693|Milling Blue ......... 694|Rose Magdala ....... 695|Paraphenylene Violet . 696|Indamin Blue ........| 418,916. 697|Indulin, spirit sol ....| 900,302. 698|Nigrosin, spirit sol ... 699|Indulin NN ...... as FOO NISTOSIN ee Wes ols hicks 0 0 701|Paraphenylene Blue R. 392,723; 524,677. 7o2|Para. Blue 5.555500 458,281. Wea RUD LCANTITI Me ae iereelea oat weal Atigamin ia. WA. wace sce TOSWLNC AMIN nGi Re eves wate 6 (Abstract, Group XV.) 710,766; 727,387. 729|Kryogen Pure Blue R| 679,199; eh als 778,713. 730|Pyrogen Black G_....| 665,547. 731|Thiophor Indigo CJ ..| 736,403; 778,478; 821,378. 732|Autogen Black .......| 646,873. 733|Immedial Indone «| 709,151. 734|Pyrogen Yellow M ... 735|Pyrogen Indigo .....| 708,662; 723,154. 736|Thion Blue B ........| 695,533; 695,534. 737|Cotton Brown .......] 640,559. 738|Cotton Black ..... Be 644,959. 739|Immedial Bordeaux G 701,435; 866,939. 740|Fast Black B ........| 545,336; 545,337; 611,112; 661,438. VAT Past. Blacks DS geses uae 546,576. ne 742|Printing Blue for. Wool 609,327. 743|Kryogen Brown A ... 609,327; 632,170; +137. Pi Gcitol Blac rier ae. |e atk 745|Melanogen Blue ..... 640,218; 658,286; 667,486, 746|Thional Green B ..... ore ake 747|Thional Brown G ....| 712,176. 748|Hydron Blue R ...... 919,572; 931,598; 6, , , a ed 749|Anthraquinone Black . mas ht Leenks 750|Kryogen Brown A ... : ; 4 751|Kryogen Brown RB . 752|Kryogen Direct Blue: GOoek . se'oas 753|Kryogen Direct Blue B 754|Kryogen Direct Blue aB ee ytecrec cs 755|Kryogen Black BNX.. 756|Kryogen Black TGO . 757|Sulfogen Brown G ... (Abstract, Group III.) 906,367. 766|Indanthrene Violet R.. 758|Sirius Yellow G ..... 968,376 759|Anthraflavon G ......| 837,840 760|Indanthrene Gold Orange: a.c sees F 856,811 761|Indanthrene Gold CATED eas ot hose sas = + 055,105. 762|Indanthrene Scarlet G.| 623,069; 955,105. 763|Indanthrene Dark gh Gavoul 8) OMS ae one 818,992. 764|Indanthrene Violet RD 8373795. 765|Indanthrene Green B .! 796,393. 767|Indanthrene Violet 2 R|/1,003,z€8. 768|Indanthrene Violet B .|1,003,268. 769|Alizarin Yellow C ...} 443,402; 770|Alizarin Yellow A ...| 415,088; 771|Resoflavin W ........ 618,000; 772|\Galloflavin W ........ 348,613. 773|Anthracene Yellow ... 774|Alizarin Black WR ...| 368,054; 631,614. 775|Alizarin Dark Green W) 619,114; 452,210. 623,069. 623,069. 379,150; 610,115; NAME Group XVI.—(Continued).—-ANTHRAQUINONE. rinting Black, for wool 777|Chromogen I .. ye8| Alizarin VI .scersaiee 776 eceveee 779|Alizarin Orange A ... 780|Alizarin Red S .. 781|Erweco Alizarin Red. 782|Anthracene Brown W. 783|Purpurin 784|Alizarin SX .... 78s5|Alizarin GI 786|Alizarin Red 3 WS... 787|Alizarin Bordeaux B.. 788|Alizarin Cyanin R ... 789|Anthracene Blue WR. eoee 790|Acid Alizarin Blue BB 791|Indanthrene Olive G .. 792|Cibanone Orange R .. 793|Cibanone Blue 3 G ... 794|Cibanone Black B .... 795|Cibanone Yellow R .. 796|Acid Alizarin Green G 797\Alizarin Garnet R ... 798|Alizarin Maroon W .. Hed beat Cyanin G .... 800|/Anthracene Blue WG. Sor bantutees Blue WGG 802|Anthracene Blue WG, 1S OW) capects = Pe coe 803|Alizarin Blue X 804|Alizarin Blue S ...... 8o05|Alizarin Green S .. 806|Alizarin Black P ..... 807|Alizarin Black S ..... 808|Alizarin Green X .... 809|Alizarin Indigo Blue S 810|Helindone Yellow GINS Beteletenn 9 aca ah Ne 8r1|Algol Yellow 3 G.... 812|Indanthrene Orange RT 813|Indanthrene Copper R 814|Algol Yellow WG .... 815|Algol Scarlet G ...... 816|Algol Red 5 G ... _ 817|Algol Yellow R ...... e oe 818| Algol Rose R ....eeee 819|Algol Red R ...-eeee 820| Algol Brilliant Violet R 821|Algol Brilliant Violet BB | esoceoveeeees DIGEST OF PATENTS 609,327. Patent No. 95,465; Re. 4,321; 97,597; Re. 4,558; 127,426; 154,153; 1,036,880; t.260,152:; 186,032. 95,465. 826,500. 686,356. 186,032; 446,893. 446,892. 502,603; 506,265; 922,282. 902,895. 476,410; 502,603; 654,506. 617,686. 654,505. 186,032; 258,530 274,081; 399479. 399,479; 399,481; 401,635. 399,482. 938,566. 925,917. 925,917. 938,616; 972,066; 935,781. 957,039; 957,041; 153,536; 885,577; 1,036,881; 188,061. 503,295; 519,229. 476,420. 617,686; 569,405. 258,531; 527,457- 399,480; 401,633; 938,617; 957,040; 957,042. Grove XVII.—INDIGO. 874|Indigo ... eoeovoaoeeoeoee 227,470; 233,458; 233,460; 240,359 240,042; 250,036; 251,500; 257,812; 257,814 228,300; 233,459; 235,193; 240,041; 250,035; 251,499; 251,671; 257,8133 259,260; NAME 822|Algol Brilliant Oranges ERY oyu vee 823|Algol Violet B ....... 824|Algol Orange R ...... S2slAlgol Red By .2...cen 826|Indanthrene Red G ... 827|Indanthrene Bor- deaux Bocas Se pry 828|Indanthrene Bordeaux. 829| Algol Bordeaux 3 B.. 830|Indanthrene Red R .. 831|Indanthrene Red BN.. 832|Indanthrene Violet RN 833|Algol Olive R ... 837|Indanthrene Blue R .. 838|Indanthrene Blue RS. 839|Algol Blue K 840|Indanthrene Blue 3 G. 841|Indanthrene Blue 2 GS 842|Indanthrene Blue GCD 843\|Indanthrene Blue GC. 844| Algol Blue 3 G ...... 845|Indanthrene Maroon R 846|Indanthrene Dark Blue 847|Algol Green B ....... 848|Indanthrene Gray B .. 849|Indanthrene Yellow G. 8so|Indanthrene Blue WB 8s1|Alizarin Direct Blue B 852|Alizarin Irisol D 853|Anthraquinone Violet.. 854|Alizarin Viridin DG... 855|Alizarin Pure Blue B. 856|Alizarin Astrol B .... 857|Erweco Alizarin Blue Rir cesar ws eiheren 858|Alizarin Saphirol B .. 8s09|Cyananthrol (R’ cys. ee. 860|Cyananthrol G ....... 861|Anthraquinone Blue SR 862|Alizarin Blue Black B. 863|Anthraquinone Blue Green 864] Anthraquinone | Green 865|Alizarin Cyanin Green 866|Leucol Dark Green B. 867|Indanthrene Brown B. 868|Cibanone Brown B ... 869|Algol Brown B ...... 870|Algol Corinth R ..... 871|Indanthrene Violet RN 872|Leucol Brown B ..... 873|Helindone Brown AN. (Abstract, Group VII.) | eorereeeeee eoeeeeeees Patent No. (Abstract, Group III.) 957,040; 957,042. 957039; 957,041; 814,137. 875,390. 863,397. 961,612. 863,397. 950,344. 863,397. 1,011,068. 961,048. 957,041; 957,040; 957,042. 971,225;Re.13,257. 960,182. 958,325. 682,523; 724,789; 682,523. 775,368. 970,878. 948,204. 753,659. 739,579- 801,418. 791,869. 809,892. 7753367. 767,259. 739,145. 724,789. 734,866; 599,426; 659,565; 599,426; 603,659; 599,426; 599,426; 996,487. 595,349- 715,662. 715,662. 632,621. 599,425; 599,426; 654,295; 874,744. 876,190. 915,385. 874,743. 943,717- 259,261; 262,605; 540,427; 617,651; 618,006; 619,884; 620,563; 622,139; 643,502; -|1,025,195; 1,038,003. 692,762; 855,248. 748,375. 599,427. 650,566. 599,427; 734,325. 599,427. 599,427. 749,973. 599,427; 754,768. 259,629; 276,888; 546,165; SCHULZ INDEX 585 N ie OG Wn N = é NAME Patent No. NAME Patent No. a4 n Grove XVII.—(Continued).—INDIGO. (Abstract, Group VII.) 646,841; 647,263; 662,073. 647,279; 647,280; || 889/Indigo Yellow 3 G ...| 994,088; 1,026,574. 647,281; 651,453; |] 890/Ciba Yellow G .......] 907,766; 1,074,850. 657,539; 661,871; || 891|Ciba Green G ....... 872,227; 960,098. 662,076; 662,703; || 892|Helidone Green G ....| 932,334. 662,754; 662,755; |} 893|Alizarin Indigo G ....| 961,396; 980,140; 669,794; 671,3445 999,439. 673,887; 675,217; || 894|Alizarin Indigo B ....| 998,506. 680,395; 690,332; || 895|Alizarin Indigo 3 R ..| 958,464; 958,465; | 697,545; 698,328; 961,397; 961,398; | 699,581; 704,804; 961,399; 999,439. | 712,190; 712,793; || 896|Helindone Blue 3 GN. |1,025,174. 714,000; 714,042; || 897|Ciba Heliotrope B ...] 876,158; 808,452; | 727,270; 731,3853 | 1,074,505; 1,266,092. 737,836; 746,965; || 898|Helindone Violet D ..|1,028,911. 760,171; 7Ol,440; 4) Sog|Ciba Gray G .2...... 954,273. 768,455; 772,560; || goo|Ciba Violet 3 B ...... 836,300; 848,356. 772,775; 776,884; || 901(Ciba Violet B ........ 836,300; 848,355; 778,725; 778,7523 848,356. 818,341; 839,099; || 902|Helindone Brown 2 R.! 968,697. 841,456; 850,444; || 903|Helindone Brown 5 R.| 955,609; 968,697. | 860,900; 868,294; || 904|Helindone Brown G ..| 955,699; 968,607. | 868,755; 891,708; || 905|Thio Indigo Scarlet R.| 841,003; 874,649; 937,194; 960,671; | 923,959; 943,678. 063,677; 984,442; || 906|Thio Indigo Scarlet G.| 848,355; 867,714; 1,012,363; 1,015,495; 874,649; 887,600; 1,211,413; 1,442,743. } 899,994. 87s|Indigo Salt T .......| 257,815; 540,427. ||907|Ciba Scarlet G ......| 891,690; 904,867; 876|Indigo White, 20 per bee 965,170. 1) eee Desgueess| $94,579; 906,307. || 908|Ciba Red R .......- «| OF5,3946. 877|Indigo Carmine ......| 251,501; 524,256; ||909|Ciba Red B ......... 848,354; 899,152. 540,564; 726,688. || 910|Helindone Rose BN ..| 892,897; 947,030. 878\Indigotin P ..........| 524,256. 911|Ciba Orange G ......|1,081,808. 879!Brom Indigo .........| 715,074; 729,217; || 912|Thio Indigo Red B....| 819,348; 831,844; 730,148; 807,782. 850,827; 868,205; 880!Helindone Blue BB ..| 706,921; 856,687; 877,743; 894,004; 883,703; 888,230. 894,005; 894,006; 881|Dianthrene Blue 2 B..| 706,927; 856,776; 910,839; 943,560} 937,040; 937,041. : 949,592. 1,043,468. 913|Helindone Orange R..| 867,305; 881,157; 8R2\Indigo 5 B ..........|1,043,468; 1,070,541. ; 881,158; 943,561. 883lIndigo 6 B ....... ..-|1,043,468,; 1,061.781. || 914|Helindone Orange D..| 872,585; 963,813. 884|Brilliant Indigo 2 B...| 872,115; 948,241; ||915|Helindone Fast Scarlet} 963,813. 1,043,468. 916|Helindone Scarlet S ..| 867,306. 88s5|Brilliant Indigo B ....| 761,007; 812,598; ||917|Helindone Red B ....| 916,020; 916,030. 1,042,679; 1,043,468; || 918|Helindone Red 3 B ..| 916,029; 916,030. 1,050,179. 919(/Ciba Bordeaux B ....| 867,715. 886|Brilliant Indigo G ....| 955,410; 1,043,468. || 9720|Helindone Violet BB.. |1.025.128. 887|Brilliant Indigo 4 G ..| 872,115; 957,683; || 921|Helindone Gray 2 B..| 872,085; 872,086. 1,043,468. | 959,617. SSRIINGIZO! bsicnis ss aes aides 2700002) 020.442 ° | Group XVIII.—ANILIN BLACK. (Abstract, Group IT.) 922|Anilin Black ........{ 35,589; 79,942; f)922|Anilin Black (contd.).{ 529,498; 520,499; 96,242; 111,654; 789,221; 992,047; 138,155; 180,538; | 1,326,367. 193,158; 387,097; |} 923 fabs Dipeenessncens sd 200,000) 1,105,554; | | “4 SCIENTIFIC BOOKS PUBLISHED BY The Chemical Publishing Company, Easton, Penna. ARNDT-KATZ—A Popular Treatise on the Colloids in the Indus. trial Arts. Translated from the Second Enlarged Edition. 12mo. Pages VI + 73. ARNOLD—The Motor and the Dynamo. 8vo. Pages VI + 178. 166 Figures. BARDORF AND BALL—The Elements of Sugar Refining. Pages X + 240. Illustrations. BENEDICT—Elementary Organic Analysis. Small 8vo. Pages VI + 82. 15 Illustrations. BERGEY—Handbook of Practical Hygiene. Small 8vo. Pages 164. BILTZ—Practical Methods for Determining Molecular Weights. (Translated by Jones.) Small 8vo. Pages VIII + 245. 44 Illustrations. 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