Manufacture of azo-dyestuffs and intermediate products

Abstract

Abstract 299,331. Soc. of Chemical Industry in Basle. Oct. 22, 1927, [Convention date]. Azo dyes; cyanuric compounds.-Azo dyestuffs and intermediate products containing at least one cyanuric ring and at least one thiazole ring are obtained by (1) condensing a cyanuric halide with suitable compounds at least one of which contains a thiazole ring and, if necessary, converting the product into an azo. dyestuff by diazotization and coupling or by coupling with a diazo compound, or (2) coupling a diazo component with a coupling component, such components being so selected that one contains at least one cyanuric ring and the other at least one thiazole ring. The dyestuffs so obtained may be subjected, in substance or on the fibre, to further treatment such as redaction, condensation, acidylation (including treatment with phosgene), alkylation, aralkylation arylation, further coupling with a diazo compound, diazotization and further coupling with a component, or treatment with a compound yielding metal. The following examples are specified. (1) 1 Mol. of cyanuric chloride is condensed with 1 mol. of H-acid and 1 mol. of dehydrothiotoluidinesulphonic acid and, if desired, also with 1 mol. of aniline; the products are adsorbed by cotton from a feebly alkaline Glauber's salt bath and can be developed on the fibre with diazo solutions. (2) 1. Mol. of cyanuric chloride is condensed with 1 mol. of 1 : 4- phenylenediamine-3-sulphonic acid and 1 mol. of dehydrothiotoluidinesulphonic acid and, if desired, also with 1 mol. of aniline; the products are adsorbed by cotton from a feebly alkaline Glauber's salt bath and can be diazotized and developed on the fibre with coupling components; an isomeric tertiary condensation product is obtained by condensing 1 mol. of cyanuric chloride with 1 mol. of monoacetyl - 1 : 4- phenylenediamine or of p-nitraniline, 1 mol. of dehydrothiotoluidinesulphonic acid, and 1 mol. of an anilinesulphonic acid, and saponifying or reducing the product. (3) 1 Mol. of cyanuric chloride is condensed with 1 mol. of the monoazo dyestuff p-toluenesulphonic ester of H-acid # cresidine and 1 mol. of dehydrothiotoluidinesulphonic acid; the saponified product dyes cotton strong yellowish-red tints fast to light. (4) The dyestuff aniline # (alkaline) the condensation product from 1 mol. of cyanuric chloride, 1 mol. of H-acid, and 1 mol. of dehydrothiotoluidinesulphonic acid dyes cotton pure rose tints; the dyeing can also be produced by impregnating the fibre with the condensation product and developing with the diazotized aniline. (5) The dyestuff 2-aminobenzoic acid # (alkaline) the condensation product from 1 mol. of cyanuric chloride, 1 mol. of H-acid, and 1 mol. of dehydrothiotoluidinesulphonic acid dyes cotton clear rose tints which become light reddish violet, fast to light, on after-coppering; the same dyeing is obtainable by using the copper compound of the dyestuff: the dyestuff 2-aminobenzoic acid # (alkaline) the condensation product from 1 mol. of cyanuric chloride, 1 mol. of 2 : 5 : 7-acid, 1 mol. of dehydrothiotoluidinesulphonic acid, and 1 mol. of aniline dyes cotton clear orange tint which become reddish-brown, fast to light, on after-coppering. (6) The dyestuff 2-aminophenol-4-sulphamide # (alkaline) the condensation product from 1 mol. of cyanuric chloride, 1 mol. of H-acid, and 1 mol. of dehydrothiotoluidinesulphonic acid dyes cotton red-violet tints which become fast to light on aftercoppering; the same dyeing is obtainable by using the copper compound of the dyestuff which may also be prepared by condensing 1 mol. of the copper compound of the dyestuff 2-aminophenol- 4-sulphamide # alkaline H-acid with 1 mol. of cyanuric chloride and 1 mol. of dehydrothiotoluidinesulphonic acid; the corresponding chromium compound dyes cotton violet. (7) The dyestuff, the condensation product from 1 mol. of cyanuric chloride, 1 mol. of 1 :4-phenylenediamine-3-sulphonic acid and 1 mol. of dehydrothiotoluidinesulphonic acid # acetoacetanilide, dyes cotton clear greenish yellow. (8) The dyestuffs, dehydrothiotoluidine mono- or di-sulphonic acid # the condensation product from 1 mol. of cyanuric chloride, 1 mol. of 2 : 5 :7-acid, and 1 mol of monoacetyl-1 : 4-phenylenediamine dve cotton scarlet tints fast to light, and on saponification may be diazotized on the fibre and developed with #-naphthol. A table is also given showing the colours of the dyeings on cotton with the following dyestuffs :-aniline, o- or p-toluidine, m- or p-xylidine, 2 : 5-dichloraniline, 4- aminoacetanilide, 3- (or 4-) aminobenzoic acid, 2-aminobenzoic acid methyl ester, 3-aminobenzenesulphamide, 2-anisidine, 4-chloro-2-aminodiphenyl ether, 2-amino-4-acetylamino-4<1>-methyldiphenylsulphone, 4<1> - methyl - 4 - aminodiphenylamine-2-sulphonic acid, 4-chlor-2-aminophenol, monoformyl- 1 :3 - phenylenediamine, 1. (or 2-) naphthylamine, dehydrothiotoluidine or its sulphonic acid, aminoazobenzene, 2 : 5-disulphobenzene - azo - cresidine, 2-sulpho-5-acetylaminobenzene-azo-cresidine, 4 - nitro-2-sulphobenzeneazo - cresidine, 8-oxy-3 : 6-disulphonaphthaleneazo - cresidine, 8-oxy-3 : 6-disulphonaphthaleneazo-a-naphthylamine, or 4-oxaminobenzene-azocresidine # the condensation product from 1 mol. of cyanuric chloride, 1 mol. of H-acid, and 1 mol. of dehydrothiotoluidinesulphonic acid; benzidine #2mols. of the condensation product from cyanuric chloride, H-acid, and dehydrothiotoluidinesulphonic acid; aniline, 2- anisidine, 4-nitrobenzenesulphonic acid-azo-cresidine, or 8 - oxy - 3 : 6-disulphonaphthalene-azocresidine # the condensation product from 1 mol. of cyanuric chloride, 1 mol. of H-acid, and 1 mol. of dehydrothiotoluidine; aniline, or 4- toluidine # the condensation product from 1 mol. of cyanuric chloride, 1 mol. of H-acid, and 1 mol. of dehydrothioxylidinesulphonic acid; 2- anisidine, dehydrothioxylidine, 4-nitro-2-sulphobenzene-azo-cresidine, aminoazobenzene, 8-oxy- 3 6-disulphonaphthalene-azo-cresidine, or 8-oxy- 3 : 6-disulphonaphthalene-azo - a - naphthylamine # the condensation product from 1 mol. of cyanuric chloride, 1 mol. of H-acid, 1 mol. of dehydrothiotoluidinesulphonic acid, and 1 mol. of aniline; 8 - oxy - 3 : 6-disulphonaphthalene-azo-anaphthylamine # the condensation product from 1 mol. of cyanuric chloride, 1 mol. of H- acid, 1 mol. of dehydrothiotoluidinesulphonic acid, and 1 mol. of ammonia; aniline, 2-anisidine, 4-nitro-2-sulphobenzene-azo-cresidine, or 8-oxy-3: 6 - disulphonaphthalene - azo - cresidine # the condensation product from 1 mol. of cyanuric chloride, 1 mol. of H-acid, and 1 mol. of primulinesulphonic acid, and 1 mol. of aniline; aniline. 2-anisidine, 4-nitro-2-sulphobenzene-azo-cresidine 8-oxy-3: 6-disulphonaphthalene-azo-oresidine. or 2: 5 - disulphobenzene - azo-a-naphthalenje-7-sulphonic acid-azo-a-naphthylamine -> the condensation product from 1 mol. of cyanuric chloride, 1 mol. of H-acid, and 2 mols. of dehydrothiotoluidinesulphonic acid; 4<1>methyl-4- aminodiphenylamine-2-sulphonic acid, 8-oxy-3 : 6- disulphonaphthalene-azo-cresidine, or 4-oxaminobenzene,-azo-cresidine # the condensation product from 1 mol. of cyanuric chloride, 1 mol. of H-acid, 1 mol. of dehydrothiotoluidine sulphonic acid, and 1 mol. of 4-chloro-1 : 3-diaminobenzene ; 3-aminobenzoic acid, 4-oxaminobenzeneazo-cresidine, 2-sulpho-5-acetylaminobenzene-azocresidine, 8 - oxy - 3 : 6-disulphonaphthalene-azocresidine, or 2-aminophenol-4-sulphamide # the condensation product from 1 mol. of cyanuric chloride, 1 mol. of H-acid, 1 mol. of dehydrothiotoluidinesulphonic acid, and 1 mol. of 4'-amino- 4-oxyazobenzene-3-carboxylic acid; aniline, 4- toluidine, 2-aminobenzoic acid, 2-aminophenol-4- sulphamide, 4-chloro-2-aminophenol, dehydrothiotoluidinesulphonic acid, aminoazobenzenesulphonic acid, or the condensation product from 1 mol. of cyanuric chloride, 1 mol. of 1: 4- phenylenediaminesulphonic acid, and 1 mol. of 5- amino-2-oxybenzoic acid, # the condensation product from 1 mol. of cyanuric chloride, 1 mol. of 2:5: 7-acid, and 1 mol. of dehydrothiotoluidinesulphonic acid; benzidine # 2 mols. of the condensation product from cyanuric chloride, 2 : 5 : 7-acid, and dehydrothiotoluidinesulphonic acid; 2-aminobenzoic acid, 2-aminophenol-4-sulphamide, dehydrothiotoluidine mono- or di-sulphonic acid, or 8-oxy-3 : 6-disulphonaphthaleneazo cresidine # the condensation product from 1 mol. of cyanuric chloride. 1 mol. of 2 : 5: 7- acid, 1 mol. of dehydrothiotoluidinesutphonic acid, and 1 mol. of aniline; aniline, 2-aminobenzoic acid, or 2-aminophenol-4-sulphamide # the condensation product from 1 mol. of cyanuric chloride, 1 mol. of 2 :8 : 6-acid, and 1 mol. of dehydrothiotoluidinesulphonic acid; dehydrothiotoluidinedisulphonic acid # the condensation product from 1 mol. of cyanuric chloride, 1 mol. of 2:5: 7-acid, and 1 mol. of 4-cMoro-1. : 3-phenylenediamine or 4-sulpho-1 : 3- phenylenediamine with or without 1 mol of 4- aminoacetanilide; 2 mols. of aniline, 2-anisidine, 2-aminobenzoic acid, or aminoazobenzene, # the condensation product from 1 mol. of cyanuric chloride, 2 mols. of H-acid, and 1 mol. of dehydrothiotoluidine or its sulphonic acid; 2 mols. of aniline, 4-toluidine, or 2-amino-1 : 4-dimethylbenzene # the condensation product from 1 mol. of cyanuric chloride, 1 mol. of H-acid, 1 mol. of 2 : 5 : 7-acid, and 1 mol. of dehydrothiotoluidinesulphonic acid; 2 mols. of aniline or 4. toluidine # the condensation product from 1 mol. of cyanuric chloride, 1 mol. of H-acid. 1 mol. of 2 : 8 6-acid, and 1 mol. of dehydrothiotoluidinesulphonic acid; the condensation product from 1 mol. of cyanuric chloride, 1 mol. of dehydrothiotoluidinesulphonic acid, and 1 or 2 mols. of 4<1>-amino-4-oxyazobenzene-3-carboxylic acid; the condensation product from 1 mol. of cyanuric chloride, 1 mol. of 1: 4-phenylenediamine-2-sulphonic acid, and 1 mol. of

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