GB812211A - Nitro-phenylene diamines and their use in dyeing animal fibres - Google Patents

Abstract

The invention comprises mononitrated o-phenylene diamines having the nitro group in para position to one of the amino groups and mononitrated p-phenylene diamines, wherein the amino group furthest from the nitro group is a group of the formula: <FORM:0812211/IV (b)/1> where n and p are each zero or 1 and n is at least equal to p. In examples: (1) N-(b -aminoethyl)-p-nitraniline is reduced to the corresponding phenylene diamine, acetylated to the triacetate, the latter nitrated to give 1 - amino - 2 - nitro - 4 - b - aminoethylamino-benzenetriacetate and the latter hydrolysed to give the free base; (2) ethylenediamine is condensed with 1 : 3-dinitro-4-chlorobenzene to give N - (b - aminoethyl) - 2 : 4 - dinitroaniline which is reduced with sodium hydrosulphide to give 1 - nitro - 3 - amino - 4 - b - aminoethyl-aminobenzene; (3) nitro-p-phenylene diamine is condensed with chloracetamide to yield 1-amino - 2 - nitro - 4 - carbamoyl - methylamino-benzene; which is (4) hydrolysed to yield 1-amino - 2 - nitro - 4 - carboxymethylamino benzene. The compounds are used in hair-dyeing compositions (see Group IV (c)]ALSO:A composition for dyeing animal fibres such as human hair comprises an alkaline solution of a mononitrated ortho-phenylene diamine in which the nitro group is in para-position to one of the amino groups or a mononitrated p-phenylene diamine, wherein the amino group furthest from the nitro group has the formula <FORM:0812211/IV (c)/1> where n and p are each zero or 1 and n is at least equal to p. In Examples: (1) an aqueous solution of 1-amino-2-nitro-4-b -aminoethyl-amino-benzene sulphate made alkaline with ammonia dyes live hair violet; (2) an alkaline solution of 1 - nitro - 3 - amino - 4 - b - amino - ethylamino-benzene dyes live hair golden; (3) and (4) alkaline solutions of 1-amino-2-nitro-4-N - acetamido - amino - benzene and 1-amino-2 - nitro - benzene - 4 - aminoacetic acid dye live hair red.