GB700229A - Process for the preparation of polyazodyestuffs - Google Patents

Abstract

Metallized dyes are obtained by coppering under demethylating conditions polyazo dyes of the formula <FORM:0700229/IV (c)/1> where one A is the residue <FORM:0700229/IV (c)/2> and the other is an o-carboxyaryl or o-methoxyaryl radical which may be further substituted (including by arylazo radicals); R is the residue of an o-coupling mono- or di-hydroxynaphthalene mono-, di -or tri-sulphonic acid or of an amino-, alkylamino-, alkylamino, arylamino- or acylaminonaphthol-mono- or di-sulphonic acid; the dyes may be partially coppered before the introduction of the second A-N=N- radical into the naphthalene nucleus. The starting materials are made by coupling diazotized A-NH2 twice in either order with 1 : 6-dihydroxynaphthalene-3-sulphonic acid or with J acid and replacing the amino group by hydroxyl. Coppering may be effected with a copper tetrammine complex in alkaline solution, or with in the melt with copper salts and alkali salts of aliphatic monocarboxylic acids. The products dye cotton and regenerated cellulose in blue to grey tints. Examples show the coppering of dyestuffs prepared as follows: (1) 1-naphthol-3 : 8-disulphonic acid \sMdianisidine--> 1 : 6-dihydroxynaphthalene 3-sulphonic acid \sM 4-sulpho-anthranilic acid; (2) 1-naphthol-3 : 8-disulphonic acid \sM dianisidine --> copper complex of dyestuff 1 : 6-dihydroxynaphthalene 3-sulphonic acid\sM (a) anthranilic acid or (b) 5-nitro-anthranilic acid; (3) 1-naphthol-3- : 6-disulphonic acid \sM dianisidine --> copper complex of dyestuff 1 : 6-dihydroxynaphthalene - 3 - sulphonic acid \sM4-sulphoanthranilic acid; (4) 1-naphthol-3 : 6 : 8 - trisulphonic acid \sM dianisidine --> copper complex of the dyestuff 1 : 6-dihydroxynaphthalene-3-sulphonic acid\sM(a) anthranilic acid, or (b) 5-nitro-anthranilic acid; (5) 5-nitro-2-aminoanisole-4-sulphonic acid-->1 : 6-dihidroxynaphthalene-3-sulphonic acid\sMdianisidine-->chromotropic acid; (6) 5-aminosalicylic acid-->cresidine-->1 : 6-dihydnaphthalene-3-sulphonic acid \sM dianisidine --> 1-naphthol-3 : 6 : 8-trisulphonic acid. The dianisidine couples in the 5-position of the 1 : 6-dihydroxynaphthalene-3-sulphonic acid in (4) (a) and in the 2-position in the other cases. The second coupling to this acid takes place in the presence of pyridine and ammonia. A list is given of further dyestuffs prepared showing 5-sulpho-anthranilic acid, 5-chloro-anthranilic acid and 5-nitro-4-sulpho-anthranilic acid as alternative components A and methylamino-, ethylamino-, propylamino, anilino-, acetylamino-, benzoylamino- and phenoxyacetylamino-anilinonaphtholsulphonic acids as R. Other suitable components are listed.