GB465138A - The manufacture of water-insoluble azodyestuffs and printing preparations - Google Patents

Abstract

Water-insoluble azo dyes are made by coupling on the fibre metal complex compounds of the azo dyes from resorcinol, m-aminophenol, m-phenylenediamine or the homologues or substitution products thereof capable of coupling twice and o-hydroxy- or o-carboxy-diazo compounds, the azo dyes containing no further solubilizing groups, with diazo compounds suitable for the manufacture of ice-colours. Brown shades are obtained. The coupling component may be applied to the fibre together with an arylnitrosamine or an aryldiazoamino- or iminocompound, if desired, in the form of a printing composition, and the dyestuff developed according to standard methods. The metal containing o-oxyazo dyes used as coupling components can also be obtained from o-halogen or o-alkoxyamines. In the examples: (1) cotton tissue is printed with a paste containing the diazoimino compound from 4-chloro-2-anisidine and sarcosine, the copper complex compound of the azo dye 4-chloro-2-aminophenol --> resorcinol, caustic soda, glycolmonoethylether, neutral starch tragacanth thickener, dried, steamed in presence of acetic and formic acid, rinsed, boiled, rinsed and dried (full dark brown), (2) similar to (1) using the diazoimino compound from 4-benzoylamino-2 : 5 - dimethoxyaniline and n-butylaminoacetic acid or that from 4-benzoylamino-2-chloro-5-methoxyaniline and 4-sulpho-2-methylaminobenzoic acid, (3) cotton yarn is treated in a bath containing the sodium salt of the copper compound of the azo dye 4-chloro-2-aminophenol --> resorcinol, caustic soda and turkey red oil and developed with diazotized aminoazotoluene, (4) similar to (1) using the nitrosamine from 4-chloro-2-anisidine instead of the diazoimino compound with neutral chromate in addition, (5) similar to (4) using the diazoimino compound from 4-chloro-2-anisidine and piperidine-3-sodium sulphonate or that from 1-amino-4-benzoylamino-2 : 5-diethoxybenzene and methylglucamine or the compound from diazotized 1-amino-2 : 5-dimethoxy-4<1>-nitroazobenzene and sodium cyanamide, (6) similar to (1) using the copper complex compound of the azo dye 4-chloro-2-aminophenol --> 1-methyl-2 : 6-dihydroxybenzene and the diazoimino compound from 1-amino-4-benzoylamino-2-methoxy-5-methylbenzene and sarcosine (brown, yellower than the print with the dyestuff from resorcinol), (7) similar to (1) using the copper compound of the azo dye anthranilic acid --> resorcinol and the diazoimino compound from 1-amino-2 : 5-diethoxy-4-benzoylaminobenzene and sarcosine, (8)-(10) similar to (1) using the diazoimino compound from 4-chloro-2-anisidine and sarcosine and the copper compound of the azo dye 4-chloro-2-aminophenol --> (acid or alkaline) m-aminophenol or the copper compound of the azo dye 4-chloro-2-aminophenol --> m-phenylenediamine or 4<1>-methyl-3- hydroxydiphenylamine. A table of further combinations is given including the use of chromium, nickel, manganese and cobalt compounds as coupling components.