GB837471A - New basic heterocyclic diazacyanine dyestuffs and their production - Google Patents

Abstract

Dyes the cation of which has the formula <FORM:0837471/IV(c)/1> where Q is an alkyl, aralkyl or cycloalkyl radicle, R is an o- or p-phenylene or -naphthalene group and Y and Z are H or, possibly substituted, alkyl, aralkyl, cycloalkyl or aryl radicles or, jointly, are members of a heterocyclic ring which may be substituted are made by heating o- or p-aminoazo dyes free from SO3H groups of formula <FORM:0837471/IV(c)/2> in an inert solvent at up to about 200 DEG C. and quaternating the product. The free dyes are made by coupling appropriate diazotized heterocyclic amines with the necessary R component or by condensing the p-nitroso derivatives of the aromatic amines in an acid medium with the heterocyclic amine. Specified quaternating agents are e.g. methyl iodide, ethyl bromide, benzyl chloride and dialkyl sulphates and sulphonates. Alkylation may be effected in the melt, in an organic solvent or aqueous suspension at up to about 200 DEG C. The carboxy group may be split off during quaternation. The dyestuffs dye tanned cotton, polyamides, polyurethanes and acrylonitrile polymers. Red and bluish shades are obtained. Their use in dyeing cellulose acetate is described in Specification 837,472. In examples 3-amino-1,2,4-triazole-5-carboxylic acid is diazotized and coupled with dimethyl aniline, the product heated to remove the COOH group and the dyestuff thus obtained treated with dimethyl sulphate to yield a salt which is isolated (1) as a zinc chloride complex and (2) by precipitation with sodium perchlorate. Other specified coupling components are dimethyl-m-toluidine, diethyl-m-chloraniline, bis - (b - hydroxyethyl) - aniline, dibutylaniline, N - b - hydroxyethyl - N - butyl - m-toluidine, phenyl morpholine and 1-butyl-3-hydroxy - 7 - methyl - 1,2,3,4 - tetrahydroquinoline.