Complex copper compounds of monoazodyestuffs containing quaternary ammonium groups and process for their manufacture

摘要

The invention comprises copper complexes of #s,#s1-dioxymonoazo-dyes which are free from sulphonic acid groups and which contain at least one quaternary amino group bound directly, or by a residue -Z-alk-, in which Z is a carboxylic acid amide group. The dyes are made from appropriate quaternary ammonium azodyes by conventional coppering processes, or by quaternising appropriate copper complexes or treating them with a quaternary ammonium acid halide of an aminocarboxylic acid. A preferred group of dyes are of formula where A and B are respectively diazo and coupling component residues, R1, R2 and R3 are alkyl, particularly lower alkyl, or a cycloalkyl or aralkyl residue, which residues may be substituted or two of the R residues may be united to provide a heterocyclic ring, X is an anion and the O residues are in ortho-position to the azo bridge. The quaternary ammonium group is advantageously in the diazo-component. Indicative of specified diazo components are 2-aminophenol, 4-nitro-2-aminophenol, 1-amino-2-naphthol Representative of specified coupling components are 1 - acetoacetyl - amino - 2 - chlorobenzene, 1 - ethyl - 3 - methyl - 5 - pyrazolone, 2,4 - dioxyquinoline, 6 - methoxy - 2 - naphthol, 1 - acetylamino - 7 - naphthol and 2 - oxynaphthyl - 7 - trimethylammonium chloride. Copper acetate is a preferred metalling agent, particularly in the presence of a dialkyl-formamide. The dyes are used to colour animal fibres such as silk, hair or leather or vegetable fibres such as cotton, cellulose acetate and polyacrylonitrile. Examples are provided of the preparation of the dyes and their use in colouring processes, yellow, red and blue shades being obtained.