Patent GB-357959-A (GB)
Title: Manufacture of new azo-dyestuffs
IPC: C09B29/18
Filed: 1930-06-21
Abstract: Azo dyes; azo dyes, forming on the material.-Azo dyes are made in substance or on a substratum by combining any diazo compound not containing sulphonic, carboxylic or hydroxy groups with a 3-hydroxydiphenylamine-4-carboxylic acid arylide of the formula <FORM:0357959/IV/1> where n = 1 or 2, R = a phenyl residue which may contain one or more alkyl, alkoxy, or aryloxy groups or halogen atoms and R1 = an aryl residue which may contain one or more alkyl, alkoxy, aryloxy or nitro groups or halogen atoms, or a hydroxylated residue of the benzene or naphthalene series, in which at least one o- or p-position relative to the hydroxy group is free (cf. Specification 336,428, [Class 2 (iii), Dyes &c.],). They yield brown shades when formed on the fibre and are useful for the batik industry.  In examples (1) the following dyestuffs are developed on cotton in the usual way: 3 : 5-dichloraniline --> 3-hydroxydiphenylamine-4-carboxylic acid anilide, 2 : 5-dichloraniline --> 3-hydroxy-41-chlorodiphenylamine-4-carboxylic acid-o-anisidide, 3-chloraniline --> 3-hydroxydiphenylamine-4-carboxylic acid-b -naphthylamide, 4- or 5-nitro-2-toluidine --> 3-hydroxydiphenylamine-4-carboxylic acid dianisidide, 5-chloro-2-toluidine --> 41 - chloro - 3 - hydroxydiphenylamine - 4 - carboxylic acid-3-hydroxyphenylamide, (2) a padding bath is made from 3-hydroxy-41-chlorodiphenylamine-4-carboxylic acid-p-nitranilide, Turkey red oil, caustic soda and salt, (3) de-gummed spun silk is padded with 3-hydroxy-41-chlorodiphenylamine-4-carboxylic acid-o-anisidide or p-nitranilide or 2 : 5-dichloranilide and developed with diazotized 2 : 5-dichloraniline or 4-aminoazobenzene, (4) viscose silk is padded with the p-nitranilide or o-anisidide of 3-hydroxy-41-chlorodiphenylamine-4-carboxylic acid and developed with diazotized 4-aminoazobenzene, (5) acetate silk is impregnated with 4-aminoazobenzene, diazotized on the fibre and developed with the o-anisidide or 2 : 5-dichloranilide of 3-hydroxy-41-chlorodiphenylamine-4-carboxylic acid, (6) wool is padded with the 2 : 5-dichloranilide of 3- hydroxy - 41 - chlorodiphenylamine - 4 - carboxylic acid and developed with diazotized 2 : 5-dichloraniline.  In a table the following additional components are specified : 4-chloro-2-aminodiphenylether, 1 - benzoylamino - 4 - amino-2 : 5 - diethoxybenzene, 4-amino-41-methoxydiphenylamine, o- or m-dichlorbenzidine, 2 : 4 : 5- and 3 : 4 : 5-trichloraniline, 41-nitro-2 : 5-dimethoxy-4-aminoazobenzene, 2 : 5-dichlor-4-toluidine, 2-chlor-4-nitraniline, 4- or 5-nitro-2-anisidine, 1-aminoanthraquinone, 4-amino-3 : 21-dimethylazobenzene, o-nitraniline, 3-nitro-4-toluidine, dianisidine, 3-nitro-4-anisidine, 4-chlor-2-toluidine, 4-chlor-2-nitraniline; 3-hydroxy-41-chlorodiphenylamine-4-carboxylic acid-o-toluidide, p-anisidide, p-phenetidide, p-phenoxyanilide, p-chloranilide, (4-chloro-2-methoxyphenyl)-amide, 4-acenaphthylamide, and 2-anthraquinonylamide, bis-(3-hydroxy-41-chlorodiphenylamine-4-carboxylic acid-)-(4-methylphenyl)-1 : 3-diamide, bis-(3-hydroxy-41-chlorodiphenylamine-4-carboxylic acid)-(-2 : 5-dichlorophenyl)-1 : 4-diamide, 3-hydroxy-21-chlorodiphenylamine-4-carboxylic acid-o-anisidide, 3-hydroxy-41-methyl - diphenylamine - 4 - carboxylic acid-o-anisidide, 3-hydroxy-21- or 31-methyl-diphenylamine-4-carboxylic acid-b -naphthalide, 3-hydroxy-21- or 41-methoxydiphenylamine-4-carboxylic acid anilide, 3-hydroxy-41-phenoxydiphenylamine-4-carboxylic acid-p-nitranilide, 3-hydroxy-21 : 41 - dichlorodiphenylamine - 4 - carboxylic acid anilide, 3 - hydroxy - 21 - methyl-51-chlorodiphenylamine-4-carboxylic acid-p-nitranilide, 3-hydroxy-31-methyl-41-chlorodiphenylamine-4 -carboxylic acid-(5-chloro-2-methoxyphenyl)-amide, 3-hydroxy-31-methyl-41-methoxydiphenylamine-4 -carboxylic acid p-nitranilide, 31-hydroxy-411-methyldiphenylamine-41-carboxylic acid-3- or 4-hydroxyphenylamide, 31-hydroxy - 211 - methyldiphenylamine - 41 - carboxylic acid-4-hydroxyphenylamide, 31-hyroxy-411- or 211 methoxydiphenylamine - 41 - carboxylic acid - 3 - hydroxyphenylamide, 31 - hydroxy - 211 - methoxy-diphenylamine - 41 - carboxylic 4 - acid - hydroxyphenylamide, 31-hydroxy-411-chlorodiphenylamine-41-carboxylic acid-3- or 4-hydroxyphenylamide, 31-hydroxy - 411 - chlorodiphenylamine - 41 - carboxylic acid-4-hydroxy-2-methylphenylamide, 3-hydroxy-6-methylphenylamide and 2-hydroxy-5-methylphenylamide, 31-hydroxy-211-chlorodiphenylamine-41-carboxylic acid-3- or 4-hydroxyphenylamide, 31-hydroxy - 211 - chlorodiphenylamine - 41 - carboxylic acid-3-hydroxy-2-naphthylamide.