Patent GB-768832-A (GB)
Title: Manufacture of water-insoluble colouring matters
IPC: C09B41/00
Filed: 1951-12-21
Abstract: High molecular weight alkylsulphonamido aliphatic carboxylic acids and salts thereof are prepared by sulphochlorinating high molecular weight aliphatic hydrocarbons, reacting the product with ammonia or a primary amine, condensing the resulting sulphonamide with a halogen carboxylic acid, and, if desired, neutralizing the product with an inorganic or organic base.  In an example, a Fischer-Tropsch hydrocarbon mixture is treated with sulphur dioxide and chlorine until about half the hydrocarbon content has been sulphochlorinated, the product is treated with ammonia, the sulphonamide mixture condensed with chloracetic acid and the product is neutralized with sodium hydroxide or carbonate.  The final product contains unchanged hydrocarbons and some alkylsulphonamide and sodium alkyl sulphonate. The potassium, ammonium, triethanolamine and cyclohexyamine salts are also referred to.ALSO:In the manufacture of water-insoluble azo dyestuff pigments, products having a soft grain and containing an oil are obtained by adding to an aqueous liquid in which the dye is formed, at any stage during the coupling operation, an aqueous emulsion of an oil or a mixture of an oil and an emulsifying agent, the emulsifying agent in either case being a high molecular weight alkyl-sulphonamido aliphatic carboxylic acid or a salt thereof with an inorganic or organic base, and the oil being present in an amount such that the oil content of the finished dyestuff does not substantially exceed 5 per cent of the weight of the dry dyestuff. The emulsifying agent may be a condensation product of a higher alkylsulphonamide with a halogencarboxylic acid, preferably containing some unaltered hydrocarbon and usually also containing sulphonamides and alkyl sulphonic acids, e.g. the sodium alkylsulphonamidoacetate product obtained by reacting a partially sulphochlorinated Fischer-Tropsch hydrocarbon fraction with ammonia, condensing the product with chloracetic acid and neutralizing with sodium hydroxide or carbonate.  The mixture of oil and emulsifying agent may, if necessary, be clarified by adding a solution promoter (e.g. water, a higher or lower fatty acid such as oleic or acetic acid, or an alcohol such as butanol), and may be added directly or after dilution with water.  In examples: (1) a tetrazo solution from 3:31-dichloro-4:41-diaminodiphenyl is run into a coupling solution of 1-phenyl-3-carbethoxy-5-pyrazolone containing chalk and a mixture of spindle oil and the sodium alkylsulphonamidoacetate product described above, after which the mixture is acidified and boiled with a further quantity of the mixture of emulsifying agent and oil; alternatively a larger quantity of the mixture of emulsifying agent and oil, or a corresponding amount of an aqueous emulsion, may be added during the coupling only; the mixture of emulsifying agent and oil may be replaced by the sodium alkylsulphonamidoacetate product alone (which contains unchanged hydrocarbons); further examples describe the preparation under mainly similar conditions of the following dyestuffs: (2) 1-amino-2-methoxybenzene-5-sulphonic acid diethylamide --> 2:3 - hydroxynaphthoic acid 21:41-dimethoxy-51-chloranilide; (3) 1-amino-2-methoxy-5-benzanilide --> 2:3-hydroxynaphthoic acid m-nitranilide; (4) 1-amino-2-methyl-5-nitrobenzene --> 2:3-hydroxynaphthoic acid p-chloranilide; (5) 2:5-dichloraniline --> 2:3 - hydroxynaphthoic acid o-anisidide.  In example (3), the corresponding potassium, ammonium, triethanolamine or cyclohexylamine salts may replace the sodium alkylsulphonamidoacetate product described above.  Other oils specified are fatty oils such as peanut, linseed and maize grain oils.ALSO:Rubber may be coloured with soft-grained water-insoluble azo pigments containing up to 5 per cent of oil, prepared by coupling the components thereof in the presence of an aqueous emulsion of an oil, the emulsifying agent being a high molecular weight alkyl-sulphonamido aliphatic carboxylic acid or a salt thereof. According to examples, the red dioazo dyestuff 3 : 31 - dichloro - 4 : 41 - diaminodiphenyl \sQ 1 - phenyl - 3 - carbethoxy - 5 - pyrazolone (2 mols) or the claret coloured monoazo dyestuff 1 - amino - 2 - methoxy - 5 - benzoic acid anilide --> 2 : 3 - hydroxynaphthoic acid m - nitranilide may be incorporated in rubber with the usual additions prior to vulcanization.