GB916697A - New azo dyes containing amido groups substituted by unsaturated radicals - Google Patents

Abstract

1-Aminobenzene - 4 - sulphonic acid (3,4-dichlorobutene-(2)yl amide) is obtained by reacting 1 - acetyl-aminobenzene-4-sulphonic acid chloride with 1 - acetylamino - 3,4 - dichlorbutene-(2) and hydrolysing the product with aqueous hydrochloric acid. The hydrochloride of 1-amino-3,4-dichlorbutene-(2) is obtained by reacting 1,3,4-trichlorbutene-(2) with hexamethylenetetramine and treating a methanol solution of the product with hydrogen chloride. The hydrochlorides of other aminohalogenbutenes-(2) and -butines-(2) are stated to be prepared by analogous methods. The amine of the formula <FORM:0916697/IV (b)/1> is obtained as sulphate by reacting 1-aminobutine-2-(ol)-(4) with 1-acetylaminobenzene-4-sulphonic acid, treating the product with hydrogen chloride and finally sulphuric acid. Such compounds are employed as intermediates in the preparation of azo dyes (see Group IV(c)).ALSO:The invention comprises azo dyes of the formula [A-N=N-B-]-(X-NH-CH2-Y-CH2-Q)n in which A represents the radical of a diazotisable amine of the benzene, naphthalene, azobenzene, benzeneazonaphthalene or heterocyclic series, B represents the radical of a compound capable of coupling of the benzene, naphthalene, acetoacetic acid ester, acetoacetic acid anilide, benzeneazonaphthalene or heterocyclic series, X represents a -CO- or -SO2- radical, Y represents one of t he radicals -C=C-, -CH=CH-, -CH=CCl-, -CH=CBr- and -CCl= CCl-, Q represents a halogen atom, an -OSO3H radical or a radical of the formula <FORM:0916697/IV (b)/1> Z represents a halogen atom or the group HSO4 and n represents 1 or 2, and a process for the preparation thereof wherein one mol of an azo dye of the formula [A-N=N-B-]-(-X-D)n is reacted with n mols of an amine of the general formula H2N-CH2-Y-CH2-Q or a diazotised amine of the general formula (Q-CH2-Y-CH2-NH-X-)p-A-NH2 is coupled with a compound capable of coupling of the general formula H-B-(X-NH-CH2-Y-CH2-Q)n-p and the reaction product is optionally reacted with a pyridine, A. B, X, Y and Q and n having the meanings given above, D representing a halogen atom and p representing 0, 1 or 2. Heterocyclic compounds specified for use as starting materials include pyrazolones, quinolines and thiazoles. The amines from which the unsaturated amido groups may be derived include such compounds as 1-amino-4-chloro- and -4-bromo-butine-(2)-, 1-amino-4-chloro- and 4-bromo-butene-(2), 1-amino-3,4-dichlorobutene and 1-amino-2.3.4-trichlorobutene. The products of the invention may be used to dye natural cellulose, e.g. cotton, or regenerated cellulose, animal fibres, e.g. wool and silk, synthetic polyamides, e.g. nylon and synthetic polyesters, e.g. polyethylene terephthalate and hexahydroterephthalate. The examples illustrate the preparation of the dyes, including preparation on the fibre and their use in dyeing processes generally.