GB870580A - New azo dyestuffs containing thiocyanoalkyl groups - Google Patents

Abstract

The invention comprises azo dyes of formula: <FORM:0870580/IV(c)/1> wherein R is the residue of a diazo compound of the benzene, naphthalene, thiazole or thiodiazole series, which is free of sulphonic or carboxylic acid groups and cyano groups, X and R1 are hydrogen or an alkyl or thiocyanoalkyl group and R2 is a thiocyanoalkyl group which may contain substituents, other than sulphonic acid and carboxylic acid groups, in the alkyl radical, all the alkyl groups having 1-5 carbon atoms. They are prepared by coupling a suitable diazonium compound with an N-thiocyanoalkyl-aniline. Specified diazo components, other than those in examples, are 4-thiocyano-aniline, 2 : 6-dibromo-4-thiocyano-aniline, 2-methyl- or -methoxy- or -nitro- 4-thiocyanoaniline, 4-amino-41-thiocyano-1 : 11-azobenzene, 2-amino-benzthiazole, 2-amino-6-thiocyano-benzthiazole, 1-aminonaphthalene and 2 : 4-dibromoaniline. The dyes give yellow, orange, red and violet shades on acetate rayon, aromatic polyester and synthetic polyamide fibres. In examples diazonium compounds prepared from 4-chloro- or -formyl- or -carbomethoxyaniline, 2 : 4-dichloroaniline, 2 : 6-dichloro-4-nitroaniline, 2-chloro-4-nitro- or -thiocyanoaniline, 2-methoxy-4-nitro- or -5-ethylsulphonyl-aniline, 2-trifluoromethyl-5-chloroaniline, 2-methyl- 5-dimethylsulphonamidoaniline, 2-bromo-4 : 6-dinitroaniline, 1-amino-2 : 4-dithiocyanonaphthalene, 2-amino-5-nitro-1 : 3-thiazole, 2-amino-4-methyl-5-nitro-1 : 3-thiazole, 5-amino-3-phenyl-1 : 2 : 4-thiodiazole, 4-amino-1 : 11-azobenzene or 4-amino-2 : 5-dimethoxy-41-nitro-1 : 11-azobenzene are coupled with N-b -thiocyanoethyl-N-methyl- or -butyl-aniline, N-methyl- or -ethyl-N-b -thiocyanoethyl- 3-methylaniline, N-(b -hydroxy-g -thiocyanopropyl)- 3-thiocyanomethyl-aniline, N : N- di(b -thiocyanoethyl)-aniline or N : N- di (b -thiocyanoethyl)- 3-methyl-aniline.