Patent GB-517630-A (GB)
Title: Manufacture of new coloured organic compounds
IPC: C07D403/14
Filed: 1938-08-02
Abstract: 517,630. Dyes.. DAVIES, J. S. H., and IMPERIAL CHEMICAL INDUSTRIES, Ltd. Aug. 2, 1938, No. 22849. [Class 2 (iii)] New coloured compounds are obtained by treating the products of Specification 516,342, or their mono or dialkyl thio ethers with organic compounds which are wholly or partly cyclic and which include the atomic grouping -CN2.CO-. Pyrazolones, thioindoxyls and those naphthols and phenols which are capable of reacting as ketones are preferred compounds having the atomic grouping -CH2.CO-. Either one or both mercapto or alkylmercapto substituents are replaced by radicals of the compounds containing this grouping. The condensation is conveniently effected by heating the reactants together, preferably in a liquid such as dimethylaniline or monochloronaphthalene. Those products which are obtained from starting materials containing the -CN2.CO- grouping and also containing aryl radicals or other nuclei, which can be sulphonated, can be converted to water-soluble derivatives by sulphonation with concentrated sulphuric acid or oleum, if necessary at a raised temperature. The insoluble products can be used as pigment dyes and usually also as vat dyes. The soluble products can be used as bases for lakes and as dyestuffs for wool and cotton. In the examples, (1) alpha - naphthol, 1:1<1> - di(methylmercapto) - 3:3<1> - bis - isoindolenylidene (made by treating the product of example (1) of Specification 516,342, with dimethylsulphate and alkali) and dimethylaniline are heated together to give a product which when dissolved in aqueous alkaline hydrosulphite solution dyes cotton a greenish-blue shade. The same product is obtained from 1:1<1> - di-(ethylmercapto)-bis-isoindolenylidene; (2) a-naphthol is heated with the product of example (1) of Specification 516,342, to give the same product as in example (1); (3) the product of example (1) is sulphonated to give a product which dyes wool greenishblue shades ; (4) tetrachloro- or diamino-1:1<1>- dimercapto - 3:3<1> - bis - isoindolenylidene, Specification 516,342, alpha-naphthol and monochloronaphthalene are heated together to give products similar to that of example (2); (5) 1:1<1> - di - (methylmercapto) - 3:3<1> - bis - isoindolenylidene is condensed with the following compounds, the products being subsequently sulphonated : the colours which these sulphonated products give on wool are indicated in brackets: (a) 4 chloro-1-naphthol (bluishgreen), (b) 5 - methoxy - 1 - naphthol (green), (c) 5 - methylamino - 1 - naphthol, (d) 5 - # - hydroxy - ethylamino - 1 - naphthol (grey), (e) 1:5 - dihydroxynaphthalene (bluish - green), (f) 1:8 - dihydroxynaphthalene (green), (g) resorcinol (bluish-grey), (h) hydroxynaphthocarbazole (reddish-grey), (j) 2:4-diketo-1:2:3:4- tetrahydroquinoline; (k) 1:3-diketo-1:2:3:4:- tetrahydro-isoquinoline and (1) 1:4-diketo- 1:2:3:4:-tetrahydro - isoquinoline ; the unsulphonated products dye cotton shades from bluish-grey to reddish-grey from alkaline hydrosulphite vats ; (6) 2-hydroxy-3-naphthoic anilide, 1:1<1>-di-(methylmercapto)-3:3<1>-bis-isoindolenylidene and monochlornaphthalene are heated together, the product dyes cotton green shades from an alkaline hydrosulphite vat; (7) 6 - ethoxythioindoxyl, 1:1<1> - di - (methylmercapto) - 3:3<1> - bis - isoindolenylidene and dimethylaniline are heated together ; (8) the product of example (7) is sulphonated ; (9) the product of example (7) is also made by heating the product of example (1) of Specification 516,342, 6-ethoxythioindoxyl and monochloronaphthalene together; (10) 2:1-naphthathioindoxyl, 1:1<1> - di - (methylmercapto) - 3:3<1> - bis - isoindolenylidene and dimethylaniline are heated together to give a product which dyes cotton in green shades from an alkaline hydrosulpnite vat; (11) the product of example (10) is sulphonated to give a compound which dyes wool green shades ; (12) 1:11 - di- (methylmer - capto) - 3:3<1> - bis - isoindolenylidene is heated with the following thioindoxyls (the colours which the sulphonated products give on wool are indicated in brackets): (a) thioindoxyl (bluish-green), (b) 5 - chloro - 7 - methylthioindoxyl (yellowish - green), (c) 6 - chloro - 4 - methylthioindoxyl (greenish-blue), 1:2 - naphthathioindoxyl (greenish - blue) and 2:3 - naphthathioindoxyl (yellowish - green); (13) 1:1<1> - di - (methylmercapto) - 3:3<1> - bis - isoindolenylidene and dimethylaniline are heated together ; (14) 1-phenyl-3-methyl-5-pyrazolone, 1:11 - di - (methylmercapto) - 3:3<1> - bi's - iso - indolenylidene and dimethylaniline are heated together to give a product which dyes cotton violet shades from an alkaline hydrosulphite vat, (15) the product of example (14) is sulphonated; (16) 1 - (4' - nitro) - phenyl - 3 - methyl - 5 - pyrazolone, 1:1<1> - di - (methylmercapto) - 3:31 - bis - isoindolenylidene and dimethylaniline are heated together; (17) rhodanine, 1:1<1> - di - (methylmercapto) - 3:3<1> - bis - isoindolenylidene and dimethylaniline are heated together.