Patent GB-541659-A (GB)
Title: Improvements in the manufacture of colouring matters
IPC: C09B69/00
Filed: 1940-06-03
Abstract: 541,659. Dyes. DREYFUS, H. June 3, 1940, No. 9665. [Classes 2 (iii) and 15 (ii)] Water-soluble dyes are obtained by subjecting a dye containing an unsaturated carbon to carbon linkage to the action of a salt of sulphurous acid, or to the successive action of sulphur trioxide or chlorosulphonic acid and of water, whereby the linkage becomes saturated with attachment of a sulphur-containing acid group to one of the said carbon atoms. Alternatively, a dyestuff component containing such an unsaturated linkage may be subjected to such action and the product converted into a dyestuff. The dyestuff products containing a single sulphur-containing acid group are suitable for colouring cellulose ester or ether materials. Specified types of dyes suitable for the treatment are (a) azo dyes of the type, aniline, a toluidine, an anisidine, a phenetidine, cresidine or a nitro or halogen derivative thereof or aminoazobenzene or its 4-nitro- or 4-nitro-2<SP>1</SP>-methyl-5<SP>1</SP>-methoxy-derivative # the N-allyl-N-methyl- or ethylderivatives of aniline, m-toluidine, cresidine, a 2:5-dialkoxyaniline, p-xylidine or 1-naphthylamine, (b) azo dyes of the type, primary amine of the benzene series carrying as nuclear substituent an O- allyl, S-allyl, O-vinyl, S-vinyl, O-cyclohexenyl or S-cyclohexenyl group# a coupling component, (c) azo dyes of the type, an aminostilbene or aminostyrene# a coupling component, (d) 1-allylaminoanthraquinone, 1- methylamino- or phenylamino-4-allylaminoanthraquinone, (e) nitro dyes such as 2-nitro- or 2:4-dinitro-4<SP>1</SP>-(methyl- or ethyl-allylamino) diphenylamine, 3-nitro-4-allylaminodiphenyl, 1- benzoylamino-3-allylamino-4-nitrobenzene, 2- nitro- or 2:4-dinitro-4<SP>1</SP>-hydroxy-diphenylamine allyl ether, or 4-nitrobenzoylamino-N-methyl- N-allyl-aniline. Examples relate to (1) treatment of the dyestuff, 4-nitro-aniline# N-methyl- N-allyl-aniline, with aqueous sodium bisulphite ; the product dyes cellulose acetate orange from a aqueous solution ; (2) treatment of N-methyl-N-allyl-aniline with aqueous sodium bisulphite and coupling of the product with diazotized 4-nitroaniline to obtain a similar product; (3) treatment of 4-aminophenol allyl ether with aqueous sodium bisulphite, diazotization of the product and coupling with 4-hydroxydiphenyl ; the product dyes cellulose acetate yellow from an aqueous bath ; (4) treatment of N-methyl-N-allylaniline with sulphur trioxide in carbon tetrachloride at -10‹ C., pouring on to ice, heating to 50‹ C., making alkaline.with aqueous caustic soda, removing the carbon tetrachloride by steam distillation and coupling the product with diazotized 4-nitroaniline ; the product dyes cellulose acetate orange from an aqueous bath. Nitro dyes. 2-nitro- or 2:4-dinitro-4'-hydroxy-diphenylamine allyl ether is obtained by re-action of 2-nitro- or 2:4-dinitro-chlorobenzene with 4-aminophenol allyl ether. 2-nitro- or 2:4-dinitro-4<SP>1</SP>-N-methyl-N-allyldiphenylamine is obtained by re-action of 2- nitro- or 2:4-dinitro-chlorobenzene with 4- amino-N-methyl-N-allyl-aniline. 4-nitrobenzoylamino-N-methyl-N-allyl-aniline is obtained by re-action of 4-nitrobenzoyl chloride with 4-amino-N-methyl-N-allyl-aniline. Amino - anthraquinone dyes. 1 - allylaminoanthraquinone and its 4-phenylamino derivative are obtained by re-action of allyl chloride on 1-aminoanthraquinone and its 4-phenylamino derivative respectively. 4-amino-N-methyl-N-allyl-aniline is obtained by reducing with stannous chloride and hydrochloric acid the azo dyestuff, sulphanilic acid# N-methyl-N-allyl-aniline.