Patent GB-554463-A (GB)
Title: Manufacture of dyestuffs
IPC: C09B43/16
Filed: 1941-07-08
Abstract: 554,463. Dyes. SOC. OF CHEMICAL INDUSTRY IN BASLE. July 8, 1941, Nos. 8607 and 8608. Convention dates, July 9, 1940 and June 5, 1941. [Classes 2 (iii) and 15 (ii)] Azo dyes giving green dyeings, of which the fastness to wet treatments is improved by treatment in the dyebath or on the fibre with a copper compound, are obtained by linking a blue anthraquinone dyestuff containing an amino group with a yellow aminoazo dyestuff containing at least one salicylic acid grouping by means of phosgene, thiophosgene, a dihalide of a dicarboxylic acid, e.g. terephthaloyl dichloride or a halogenated 6 - membered heterocycle ring compound containing at least twice the grouping -C(halogen) =N-, wherein the ring consists of 3 or 4 carbon atoms and 3 or 2 nitrogen atoms with not more than 2 nitrogen atoms linked directly, the amino group of the blue component or of the yellow component or of both being in the form of a m- or p-aminobenzoyl group, such m- or p-amino group reacting with the compound containing replaceable halogen. Specified halogenated 6- membered heterocyclic ring compounds are cyanuryl chloride or bromide, 2:4:6-trihalo-5- methyl-1:3 diazines-4-methyl-2:6-dichloropyrimidine, 2:6 - dihalo - 4 - phenyl - 1:3:5 - triazines, 2:4 - dichloroquinazoline and 1:4 - dichlorophthalazine. The products are of the general formula A-z-x-z-R 1 -N =N-R 2 , wherein A represents the residue of a blue amino- or aminoarylamino-anthraquinone, one z represents and the other z represents (one y represents -NH-connected to x, the other y represents H), x represents the linking residue derived from the phosgene &c., and - R 1 -N = N-R 2  represents the residue of yellow azo dyestuff, R 1  representing a residue of the benzene series linked to the -NH- of the symbol z and to the azo group in positions not orthoto one another and R 2  representing a residue of the benzene series carrying an ohydroxycarboxylic acid grouping. The aminoarylamine residue of the aminoarylaminoanthraquinone may be that of 1:3- or 1:4-diaminobenzene, 1:3:4- or 1:4:3-diaminobenzenesulphonic acid, benzidine or its 2- or 3-sulphonic acid, tolidine, dianisidine, 4:4<SP>1</SP>-diaminostilbene, 4:4<SP>1</SP>-diaminodiphenylmethane, 4:4'-diaminodiphenylurea and its 3-sulphonic acid, 4:4<SP>1</SP>- or 3:3<SP>1</SP>-diaminobenzoylaniline or 1-amino-4-(3<SP>1</SP>- aminobenzoyl)aminobenzene. The residue -R 1 - N=N-R 2  may be derived, for example, from 4 - amino - 41 - hydroxy azobenzene - 3<SP>1</SP> - carboxylic acid or its 3- or 5<SP>1</SP>-sulpho, 2- or 3- methyl, 2:5<SP>1</SP>-dimethyl, 2-methyl-5<SP>1</SP>-sulpho or 3 - methoxy - 6 - methyl - 5' - sulpho derivatives or from 3 - amino - 4<SP>1</SP> - hydroxy - azobenzene-3<SP>1</SP>-carboxylic acid or from the product of saponification of 4- or 3-acetylaminoaniline # 1 - (4<SP>1</SP> - hydroxy - 3<SP>1</SP> - carboxy) phenyl - 3 - methyl - 5 - pyrazolone. The blue aminoanthraquinone dyestuff may be the 1:4:5:8 - tetramino ; 1:4:5 - triamino - 8 - hydroxy or 1:5 - diamino -4:8 - dihydroxy derivatives or a 1 - amino - or alkylamino - 4 - amino - arylamino - 2 - sulphonic acid. .Various examples of the production of the dyestuffs are given. An example is also given of the process of dyeing cotton with an aftertreatment in the dyebath with copper sulphate and tartaric acid. In dyeing mixed fabrics of wool and viscose staple fibre, an after-treatment with sodium or potassium chromate in addition to the coppering treatment is advantageous. Specification 466,886 is referred to. 1 - Amino - 4 - (4<SP>1</SP> - aminodiphenyl) - amino - anthraquinonesulphonic acid for use as an aminoarylaminoanthraquinone as above, is obtained by sulphonation of 1-amino-4-(4<SP>1</SP>- aminodiphenyl)-amino-anthraquinone. The Specification as open to inspection under Sect. 91 comprises also the use as the yellow aminoazo dyestuff of a product obtained by coupling diazotized p-aminosalicylic acid with 1 - (4<SP>11</SP> - aminostilbenyl) - 3 - methyl - 5 - pyrazolone - 2<SP>1</SP> : 2<SP>11</SP> - disulphonic acid or 1 - (4<SP>1</SP> - aminodiphenyl) - 3 - methyl - 5 - pyrazolone or their derivatives obtainable by N-m- or p-nitrobenzoylation and reduction of the.nitro group. This subject-matter does not appear in the Specification as accepted.