GB435349A - Manufacture of indigoid vat-dyestuffs - Google Patents

Abstract

Indigoid dyestuffs are produced by oxidation or by condensation with the usual components of oxythionaphthene having the formula <FORM:0435349/IV/1> in which X is halogen and Y is methyl. The oxythionaphthene may be replaced by the corresponding 2 : 3-quinone or 2-derivatives thereof, and the dyestuffs may be halogenated. In examples: (1) 4 : 6-dimethyl-5 : 7-dichlor-3-oxythionaphthene is oxidized by means of sulphur in alcoholic soda solution; (2) 4 : 6-dimethyl - 5 : 7 - dichlor - 3 - oxythionaphthene is condensed with the following components: the 2 - p - dimethylaminoanil of 3 - oxythionaphthene, 5 : 7 - dibromisatinchloride, 5 : 7 - dichlorisatinchloride and 4 - methyl - 5 - chlor - 7 - methoxyisatinchloride. The properties of the following dyestuffs are tabulated (a) dyestuffs obtained by condensing 4 : 6 - dimethyl - 5 : 7 - dichlor - 3 - oxythionaphthene with acenaphthenequinone and the 2-p-dimethylaminoanils of 5 - chlor - 7 - methyl - 3 - oxythionaphthene, 5 - methyl - 6 - chlor - 3 - oxythionaphthene, 4 - methyl - 6 - chlor - 3 - oxythionaphthene, 6 - chlor - 3 - oxythionaphthene, 6 - ethoxy - 3 - oxythionaphthene, 5 : 7 - dibrom - 3 - oxythionaphthene, 4 : 6 - dimethyl - 7 - chlor - 3 - oxythionaphthene, 1 : 2 -, 2 : 1 - and 2 : 3 - naphththioindoxyl and of 1-chlor-2 : 3-naphththioindoxyl; (b) dyestuffs obtained by condensing 4 : 6-dimethyl-5 : 7-dibrom-3-oxythionaphthene with the p-dimethylamionanils of 6-ethoxy-3-oxythionaphthene, 4-methyl-6-chlor - 3 - oxythionaphthene, 5 - methyl - 6 - chlor - 3 - oxythionaphthene, 5 - chlor - 7 - methyl - 3 - oxythionaphthene and of 6 - chlor - 3 - oxythionaphthene; (c) dyestuffs obtained by condensing 4 : 6-dimethyl-5-chlor-7-brom-3-oxythionaphthene with the p-dimethylaminoanils of 4-methyl-6-chlor-3-oxythionaphthene, 5 - chlor - 7 - methyl - 3 - oxythionaphthene, 6-ethoxy-3-oxythionaphthene and 5-methyl-6-chlor-3-oxythionaphthene; (d) dyestuffs obtained by condensing 4 : 6-dimethyl-5-brom-7-chlor-3-oxythionaphthene with the p-dimethylaminoanils of 4-methyl-6-chlor-3-oxythionaphthene and of 5-chlor-7-methyl-3-oxythionaphthene and (e) dyestuffs obtained by condensing 4 : 6 - dimethyl - 5 - brom - 7 - chlor - 3 - oxythionaphthene with the p-dimethylamionanils of 5 - methyl - 6 - chlor - 3 - oxythionaphthenes and of 6 - ethoxy - 3 - oxythionaphthenes. As coupling components are also mentioned naphthols, oxyanthracenes and naphthisatins. Samples have been furnished under Sect. 2(5) of dyestuffs obtained by condensing the 2-p-dimethylaminoanil of 4 : 7-dimethyl-5-chlor-3-oxythionaphthene with 4 : 6-dimethyl-5 : 7 - dibrom - 3 - oxythionaphthene, 4 : 6 - dimethyl - 5 - chlor - 7 - brom - 3 - oxythionaphthene and with 4 : 6-dimethyl - 5 - brom - 7 - chlor-3-oxythionaphthene. 4 : 6 - Dimethyl - 5 : 7 - dichlor - 3 - oxythionaphthene may be prepared as follows: 1-amino-2 : 4 - dimethyl - 6 - benzenesulphonic acid is converted into 1 - chlor - 2 : 4 - dimethyl - 6 - benzenesulphonic acid by diazotizing and treating with cuprous chloride, the sulphonic acid is reacted with phosphorus pentachloride. The resulting 1 - chlor - 2 : 4 - dimethyl - 6 - benzenesulphochloride is reduced, condensed with chloracetic acid and ring closure of the thioglycollic acid thus produced effected after further chlorination by means of sulphuryl chloride. The Specification as open to inspection under Sect. 91 comprises also the production of dyestuffs by condensation of 4 : 6-dimethyl-5 : 7-dibrom-3-oxythionaphthene with 2-p-dimethylaminoanil of 4 : 7 - dimethyl - 5 - chlor - 3 - oxythionaphthene, 4 : 6 - dimethyl - 5 - chlor - 7 - brom - 3 - oxythionaphthene with 2 - p - dimethylaminoanil of 4 : 7 - dimethyl - 5 - chlor - 3 - oxythionaphthene and 4 : 6 - dimethyl - 5 - brom - 7 - chlor - 3 - oxythionaphthene with 2 - p - dimethylaminoanil of 4 : 7 - dimethyl - 5 - chlor - 3 oxythionaphthene. This subject-matter does not appear in the Specification as accepted.