GB611320A - Improvements in and relating to azo dyestuffs - Google Patents

Abstract

Arylenediamines in which both amino groups are substituted by a sulphonic group and one of them also by an organic radical are obtained by treating arylene diamines, in which one of the amino groups is primary and the other secondary, with sulphonating agents (e.g. sulphuric anhydride, sulphuric chlorhydrin, chlorosulphonic ester, oleum or pyridinium sulphonate) mixed or combined with a tertiary amine (e.g. pyridine or dimethylaniline), if desired in the presence of a solvent or diluent. In the examples, N1 - methyl - 1 : 4 - diaminobenzene-N1 : N4-disulphonic acid, 1 : N2-dimethyl-2 : 4-diaminobenzene-N2 : N4-disulphonic acid, and N1-phenyl-1 : 4-diaminobenzene-N1 : N4-disulphonic acid and its 41-methyl and 41-methoxy derivatives are prepared by treating the appropriate diamines (in some cases in the form of the hydrochloride) in the presence of pyridine with sulphuric chlorhydrin or its reaction product with pyridine. Specifications 5689/03, [Class 2], 186,057, 202,630, [both in Class 2 (iii)], and 231,889, [Class 2 (ii)], are referred to. The Specification as open to inspection under Sect. 91 comprises also a reference to the sulphoration of 1 - chloro - N3 - methyl - 3 : 4-diaminobenzene, which is obtainable by the action of methylamine on 1-chloro-3 : 4-dinitrobenzene, followed by reduction. This subject-matter does not appear in the Specification as accepted.ALSO:Azo dyestuffs are manufactured by treating with a diazotizing agent an arylenediamine of which both amino groups are substituted by a sulphonic group and one of them also by an organic radical (whereby this latter amino group is unaffected whilst the other is converted into a diazo group), and coupling the resulting diazo compound (which is probably in the form of an internal salt) with any coupling component soluble or insoluble in water. The products dye wool, silk, lanital and animalized cellulosic fibres. Examples describe the production of dyestuffs from the following components: diazo components: N1-methyl-1 : 4-diaminobenzene-N1 : N4-disulphonic acid, 1 : N2-dimethyl-2 : 4-diaminobenzene-N2 : N4-disulphonic acid, and N1-phenyl-1 : 4-diaminobenzene-N1 : N4-disulphonic acid and its 41-methyl and 41-methoxy derivatives; coupling components: 2 : 3 - hydroxynaphthoic acid anilide, o-toluidide, o-and p-anisidide, o-phenetidide, 2-methyl-4-methoxyanilide, m-nitranilide, 2 : 5-dimethoxyanilide and b -naphthylamide, 2-hydroxycarbazole - 3 - carboxylic acid p - chloranilide, 2-hydroxynaphthocarbazole-3-carboxylic acid p-anisidide (derived from 1 : 2-benzocarbazole), 2 - hydroxyanthracene - 3 - carboxylic acid o - toluidide, 3-hydroxydiphenylene oxide-2-carboxylic acid 2 : 5-dimethoxyanilide, terephthaloyldiacetic acid 2 : 4-dimethoxy-5-chloranilide, di - (acetoacetyl) - o - tolidine, b - naphthol, 1 - phenyl - 3 - methyl - 5 - pyrazolone, 1 : 8 - di - hydroxynaphthalene-3 : 6-disulphonic acid, and a -naphthylamine. Specifications 5689/03, [Class 2], 186,057, 202,630, [both in Class 2 (iii)], and 231,889, [Class 2 (ii)], are referred to.