Patent GB-274130-A (GB)
Title: Manufacture of new dyestuffs
IPC: C09B43/14
Filed: 1927-07-11
Abstract: 274,130. Soc. of Chemical Industry in Basle. July 10, 1926, [Convention date]. Samples furnished. Azo dyes and metal compounds thereof.-Azo dyes of the general formula R1-N=N-R2- NH-X-NHR3, in which R1 is an alphanaphthol residue originating from a diazotized 1 : 8-aminonaphthol, R2 the residue of a primary amine of the benzene series which can be coupled in the 4-position to the amino group, R3, any aromatic complex containing at least one azo group, and X is -CO- or -CS-, are obtained bv the action of phosgene or a substitute therefor, or thiophosgene or carbon bisulphide on two molecular proportions of aromatic amino compounds, of which at least one must consist of an aminoazo dye obtained by coupling a diazotized 1 : 8- aminonaphthol or an O-acidyl derivative thereof with a primary amine of the benzene series, while the other may consist of any amino-mono- or amino-poly-azo dye, or of a component of such, a dye which can be transformed into the dyestuff after being united with the first-mentioned aminoazo dye by means of phosgene or the like. The products dye vegetable fibres direct in various shades of orange, red and blue, which are fast to light and can readily be discharged. The fastness of the dyeings can in some cases be increased by after-treatment with metal salts, or the dyes may be converted into metal compounds. In examples (1) the monoazo dye made by coupling the p-toluene sulphonic ester of H-acid with cresidine is treated with phosgene, and the product obtained by salting out is treated with caustic soda solution to remove the acidyl group: it dyes cotton in blue-red tints; the same product may be made by starting with the dyestuff from diazotized H-acid and cresidine, and other products dyeing in red tints are obtained by substituting other 1 : 8-aminonaphthols, e.g. K-acid or 1 : 8 : 4-acid for H-acid, or by replacing cresidine by aniline, m-toluidine or xylidine, (2) an equimolecular mixture of the monoazo dyes from diazotized H-acid or its p-toluene sulphonic ester and cresidine, and from monoacetyl-p-phenylenediamine sulphonic acid and 2 : 8 : 6-acid (acid coupling, the product being saponified) is treated with phosgene; the product dyes cotton red if the p-toluene sulphonic ester group is present, or blue-red if this group is absent, other red dyes are obtained by replacing the second-mentioned dye with the dye from diazobenzene or diazoazobenzene and 2 : 5 : 7-acid (alkaline coupling), (3) an equimolecular mixture of the monoazo dye from the p-toluene sulphonic ester of H-acid and cresidine and of the reduced monoazo dye from p-nitraniline and salicylic acid is treated with phosgene; the product dyes cotton in orange shades when the acidyl group is present, or in orange-red shades if the acidyl group is split off, and the fastness to light of the dyeings is increased if the dyes are converted into copper compounds: further orange dyes may be obtained by substituting for the reduced dye from p-nitraniline and salicylic acid amino-azobenzene or the product of coupling a diazotized aminosulphonic acid of the benzene or naphthalene series, e.g. sulphanilic acid, a chloranilinesulphonic acid, a toluidinesulphonid acid, an aminophenolethersulphonic acid, 1 : 4-naphthyl. aminesulphonic acid, 1-naphthylamine-2 : 4, 3 : 8 or 4: 8-disulphonic acids, 2-naphthylamine-4: 8- disulphonic acid, or alpha- or #-naphthylamine, with an amine, e.g. cresidine, xylidine, o- or mtoluidine or aniline. The Specification as open to inspection under Sect. 91 (3) (a) comprises also the production of the corresponding dyestuffs in which R2 is the residue of a primary. amine of the naphthalene series. This subject-matter does not appear in the Specification as accepted. Specification 21202/10 is referred to.