GB496678A - Improvements in dyeing and printing cellulose esters and ethers - Google Patents

Abstract

Azo dyes, forming on the material; cellulose esters or ethers, dyeing; printing.-Cellulose ester or ether materials are dyed or printed by producing thereon azo dyes from aryl-azo-amidines (obtained by combining diazotized unsulphonated arylamines with amidines of aliphatic, aromatic or heterocyclic carboxylic acids) and coupling components. The development of the dyeing may be effected by the action of acids, e.g. acetic or formic acid, or of agents splitting off acid, e.g. ammonium sulphate or thiocyanate or diethyl tartrate. Specified coupling components are phenols, naphthols, amines of the benzene and naphthalene series, aminonaphthols, hydroxy- and amino-substituted pyridines or quinolines, o-hydroxycarboxylic acids and their derivatives, e.g. 2 : 3-hydroxynaphthoic acid and its esters, amides and arylides, esters and arylides of acylacetic acids, pyrazolones and N-alkylquinolones. In examples, (1) acetate artificial silk is treated for 1 hour with an aqueous solution at 50-60 DEG C., containing an alcoholic solution of phenyl-azo-butyramidine, the o-toluidide of 2 : 3-hydroxynaphthoic acid and soap, rinsed and treated for 1/2 hour with dilute acetic acid at 60-70 DEG C. to obtain a fast red dyeing; (2) acetate artificial silk is treated for 1 hour with an aqueous soap solution at 50-60 DEG C. containing 4-chlorophenyl-azo-butyramidine, rinsed and treated for 1/2 hour with an aqueous solution at 50-60 DEG C. of 2 : 8-dihydroxy-1 : 2 : 3 : 4-tetrahydro-4-azaphenanthrene (cf. Specification 446,745) to obtain a violet dyeing; alternatively the goods may be treated first with a solution of the coupling component and then with a suspension of the azo-amidine; (3) acetate artificial silk is treated for 1 hour in a weakly alkaline aqueous solution at 60-70 DEG C. containing phenyl-azo-benzamidine, the condensation product from b -naphthalenesulphonic acid and formaldehyde, turkey red oil and the 21-naphthylamide of 2 : 3-hydroxynaphthoic acid, rinsed, treated for 1/2 hour with dilute acetic acid as in (1), rinsed and soaped to obtain a clear fast red dyeing; (4) acetate artificial silk is printed with an aqueous paste containing p-tolyl-azo-benzamidine and the 41-chloro-21 : 51-dimethoxyanilide of acetoacetic acid dissolved in methylcyclohexanone, and gum arabic, and the material is then subjected to the action of steam at 100 DEG C. containing acetic acid or treated with hot dilute acid to obtain a yellow print. Phenyl - azo - butyramidine is obtained by reaction of phenyldiazonium chloride with butyramidine, which is obtained by the action of aqueous ammonia on the butyrimido methyl ether hydrochloride produced by reaction of butyronitrile with methanol and hydrogen chloride. 4-Chlorophenyl-azo-butyramidine is obtained similarly from 4-chlorophenyldiazonium chloride and butyronitrile. Phenyl-azo-benzamidine and p-tolyl-azo-benzamidine are obtained similarly from phenyl- and and p-tolyl-diazonium chlorides respectively and benzonitrile.