GB860634A - New water-soluble monoazo heterocyclic basic dyestuffs and their preparation - Google Patents

Abstract

The invention comprises dyes of formula: <FORM:0860634/IV(c)/1> where R is alkyl or aralkyl, X and Y are nonionogenic substituents, including constituents of an #s-condensed benzene ring which may be substituted, A is a divalent residue of an amine or enamine of which the N atom is connected with the cyclic amidine grouping by means of an alkyl and/or aryl radical, Z- is an anion of an inorganic or organic mono- or poly-basic acid and n is an integer of 3 to 7. They are made in conventional fashion by alkylating or aralkylating the dye obtained by coupling appropriate diazotized 2-amino-thiazoles or -benzthiazaole and amines or enamines. They may also be made by coupling appropriate amines or enamines with 3-alkylated- or -aralkylated-thiazolone-, or -benzthiazolone, 2-hydrazones in the presence of an oxidizing agent, (see Specification 782,310). Typical of the diazotizable amines used are : 2-aminothiazole, 2-amino-4, 5-dimethyl-, 4-phenyl, 5-nitro- and 5-cyanothiazoles and 2-amino-6-methoxybenzthiazole. Representative of hydrazones specified are :-3-methyl-4-phenyl-thiazolone-2-hydrazone, 3-methyl-6-methoxybenzthiazolone - 2 - hydrazone and 3-methyl-6-acetylaminobenzthiazolone - 2 - hydrazone. Typical of coupling components specified are:-N-phenyl-N-methyl-N-phenyl - and N-(2-hydroxethyl)-N-(2 - methoxy - 5 - methylphenyl)-ethylene diamine, N-butyl -N-phenyl-1, 3-diaminopropanol-(2), N-(beta-aminoethyl)-4-ethoxy-diphenylamine and 1-(gamma-aminopropyl)-3-hydroxy-1, 2, 3, 4-tetrahydroquinoline. The dyes colour fibres of cotton mordanted with tannic acid, cellulose acetate, polyamides, polyurethanes, polyesters and polymers and copolymers of acrylonitrile and dicyanoethylene. Examples are provided of the preparation of the dyes and their use in colouring fibres of polymers and copolymers of acrylonitrile in blue or red shades.