GB662573A - Process for the manufacture of new azo-dyestuff derivatives and the application thereof in dyeing and printing - Google Patents

Abstract

The Specification describes but does not claim the preparation of halides of halo-sulphoacetic acids as in Specification 662,572, and in addition mentions thionyl chloride as a suitable reagent, no organic base then being used.ALSO:Azo dyestuffs containing the atomic grouping <FORM:0662573/IV (c)/1> (where R1 is a cyclic residue attached as shown) and free from solubilizing groups, are reacted with at least 2 molecular proportions of a halide of an acid <FORM:0662573/IV (c)/2> , where X is chlorine or bromine. Such halides are obtained as in Specification 662,572 (see Group IV (b)), and may be prepared in situ by mixing the acid with the dyestuff before conversion into the halide. The dyestuffs are preferably derived from arylides of 2 : 3-oxynaphthoic acid or of 2-oxydibenzofuran-3-carboxylic acid coupled with diazo components suitable for the manufacture of ice colours. Acylation occurs at both the hydroxy group and the amide N-atom, the carboxylic group of the acylating agent taking part in the reaction. The products are hydrolysed back to the parent dyestuffs with weak dilute alkali, e.g. with aqueous or gaseous ammonia. Thus, wool or other animal fibre may be dyed with the acylated products from an acid or neutral bath and hydrolysis effected on the fibre. Alternatively, the acylated products may be made up into acid or neutral printing pastes, applied to cotton and developed with alkali. In the examples: (1)-(17), dyestuffs from the following components are acylated with chloro-sulpho-acetyl chloride: 3-chloroaniline, 2 : 5-dichloroaniline, 2-methyl-4 - chloroaniline, 2 - methoxy - 4 - chloroaniline, 2 : 5 - diethoxy - 4 - benzoylaminoaniline and a -naphthylamine: 2 : 3-oxynaphthoic anilide and 21-methoxyanilide; (18) the dyestuff from 2-methyl-4-chloroaniline and 2-oxy-dibenzofuran - 3 - carboxylic - 21 : 51 - dimethoxyanilide is acylated with chloro-sulpho-acetyl chloride; (19) the dyestuff from 3-chloroaniline and 2 : 3-oxynaphthoic 21-methoxyanilide is acylated with bromo-sulpho-acetyl chloride; (20) wool is dyed with an acylated dyestuff and the dyeing developed with ammonia; (21)-(24) cotton is printed with an acid paste of the acylated dyestuffs and the usual thickeners and the colour developed with ammonia. Other specified diazo components are: 2-trifluoromethyl - 4 - chloroaniline, 5 - trifluoromethyl - 2 - chloraniline, 2 - ethylsulphonyl - 5 - trifluoromethyl-aniline, 3 : 5-bis-trifluoromethylaniline, 2-nitraniline, 4-chloro-2-nitraniline, 4-methyl - 2 - nitraniline, 4 - methoxy - 2 - nitraniline, 6 - methoxy - 3 - nitraniline, 2 - methoxy - 5 - methyl - 4 - benzoylamino - aniline and 4 - amino - 3 : 21 - dimethyl - azobenzene. The Aryl group in the above formula may be phenyl, o-tolyl, 2-methoxyphenyl, 4-chloro-2-methylphenyl, 2 : 5 - dimethoxy - 4 - chlorophenyl, 2 : 4-dimethoxy-5-chlorophenyl or 2-methyl-4-methoxyphenyl, or may be a naphthalene residue. Specifications 480,358 and 512,664 are also referred to.