GB365531A - Manufacture of azo-dyestuffs insoluble in water and intermediate products therefor - Google Patents

Abstract

Azo dyes are made in substance, on the fibre or on a substratum by coupling a diazo compound with an aroylene-bis-acetic acid monoarylide of the formula: R<1>-NHCOCH2-CO-R-CO-CH2-CONHR<1> in which R and R<1> = aryl residues substituted or not, both components being free from groups which would make the dyestuff soluble in water. They yield yellow to red shades fast to light. In examples the following components are specified: arylides--the anilide, 4-chloro-2-methyl-1-anilide, o- and p-toluidide, o-chloranilide, p-anisidide, a - and b -naphthylamide, and 2 : 5-dichloranilide of terephthaloyl-bis-acetic acid, the anilide and o-chloranilide of isophthaloyl-bis-acetic acid, the anilide and o-chloranilide of dibenzoyl-4 : 4<1>-bis-acetic acid, the anilide and o-chloranilide of naphthoylene-1 : 5-bis-acetic acid; diazo components--1-amino - 2 - methyl-4 - nitrobenzene, 1 - amino - 2-methyl-5-chlorobenzene, 1-amino-4-methoxy-2-nitrobenzene, 1-amino - 2 - methoxy-4-nitrobenzene, 1 - amino - 4 - methyl - 2 - nitrobenzene, a -aminoanthraquinone, 2 : 5 - dichloraniline, 1 - amino - 4 - chloro-2-nitrobenzene. Specification 355,709 is referred to. Aroylene-bis-acetic acid monoarylides are made by condensing with an aromatic amine an aroylene-bis-acetic acid ester. Aroylene-bis-acetic acid-esters are made by condensing an aromatic dicarboxylic acid chloride with an acetoacetic ester and subsequent acid cleavage.