GB806634A - Process for the manufacture of salts of sulphuric acid esters of leuco vat dyestuffs of the anthra-quinone series - Google Patents

Abstract

Water-soluble salts of sulphuric acid esters of leuco vat dyes of the anthraquinone series which are difficult to esterify as defined in Specification 719,621, are esterified by treating the vat dye in a mixture of diethylcyclohexylamine and/or at least one diethyl-(monomethyl-cyclohexyl) amine and at least one inert liquid diluent having a dissolving or dispersing action on chlorsulphonic acid addition products of the said amines, the said mixture containing 30-90 per cent of the amine or amines, and in the presence of at least one finely divided metal, with chlorsulphonic acid in the form of its addition products with the said amine or amines, and converting the resulting sulphuric ester compound into a water-soluble ester salt. At least 1.4 mols. amine are used per 2 mols. chlorsulphonic acid, except that if less than 4 mols. acid are used, at least 2 mols. amine is necessary. At least 1.5 atomic proportions of metal are necessary for each anthraquinone nucleus in the vat dye. The metal may be activated according to Specification 766,638. Oxygen may be excluded. In examples, chlorsulphonic acid is added to a mixture of diethylcyclohexylamine and 1.2 - dichlorethane in presence of brass, iron, copper, cobalt or zinc and the following are added: (1) 1.5- or 1.4-dibenzoylaminoanthraquinone; (2) the anthrimide from 1.3 - dichloro - 2 - methyl - anthraquinone and 1.4 - monobenzoyl - diamino - anthraquinone, (3) 1 - benzoylamino - 4 - (41 - dimethylsulphonamido) - benzoylaminoanthraquinone, (4) 1 - benzoylamino - 4 - methoxy - anthraquinone, (5) carbazolized di - (51 - benzoylamino - 11 - anthraquinonyl1 - 2,8 - diaminochrysene, (6) 1 - benzoylamino - 5 - chloranthraquinone, (7) 2.5.6.7.8 - pentachloro - 3,4-phthalyl - acridone, (8) 2.5.7 - trichloro- 3,4-phthalyl - acridone, (9) 2 - p - chlorbenzoylamino - 3.4 - phthalylacridone. Other inert diluents specified in examples are n-butyl chloride, sec.-butyl chloride, tert.-butyl chloride, chloroform, acetone, dioxane, trichlorethane, n-propyl bromide, sec.-butyl bromide, toluene, monochlorbenzene, o-dichlorbenzene, xylene, or nitrobenzene, and the use of methyl homologues of diethyl-cyclohexylamine. Other inert diluents specified are tetrachlorethane, n-propyl chloride, sec.-butyl bromide, tert.-amyl chloride, acetonitrile, benzene, benzene. Specification 745,365 and 745,368 also are referred to.