Patent GB-556469-A (GB)
Abstract: 556,469. Derivatives of 2 : 4 - diamino - 1:3:5- triazine. GEIGY AKT.-GES., J. R., and GROVES, W. W. April 2, 1942, No. 4401. Addition to 540,651. [A Specification was laid open to inspection under Sect. 91 of the Acts, Oct. 4, 1942.] [Classes 2 (iii) and 15 (ii)] Derivatives of 2 : 4 - diamino - 1 : 3 : 5 - triazine are prepared by reacting an aryl - alkyl - biguanide or an aralkyl - alkyl - biguanide in which the aryl or aralkyl - group and the alkyl group are linked to the same nitrogen atom, with a carboxylic acid halide in the presence of a non-caustic alkali. The compounds so obtained may be alkylated and/or sulphonated. Acid chlorides mentioned include stearic acid chloride, the chloride of palm nut fatty acids, naphthenic acid chloride and fencholic acid chloride. The parent biguanides may be prepared by reacting dicyandiamide with an alkylarylamine. Compounds mentioned include monoethyl- or monomethyl - aniline or the commercial mixture of mono- and dimethyl aniline obtained by methylating aniline, also N - ethyl and N - methyl toluidines, N - alkyl - xylidine, N - alkyl anisidines, N-alkyl-phenetidines, and other alkylarylamines, substituted in the aromatic nucleus. Alternatively the parent biguanides may be produced in a manner analogous to that used for producing dialkyl - biguanides by way of the complex copper salts. In examples (1) a chlorobenzene solution of stearic acid chloride is reacted with dry methyl - phenyl biguanide at 70‹C. in the presence of anhydrous sodium carbonate. The temperature is raised to 110 during 20 hours following which the saline magma is filtered. The product so produced is immediately methylated by means of dimethyl sulphate and the methylated compound then sulphonated by treatment with sulphuric acid monohydrate followed by fuming sulphuric acid. The sulphonated product is a yellowish crystalline water soluble powder. (2) N - Ethyl - N - phenyl - biguanide prepared by treating monoethylaniline with dicyandiamide is treated with stearic acid chloride in chlorobenzene solution, and then methylated and sulphonated as in example (1) to give a very similar product. (3) Methyl - phenyl - biguanide is reacted with the chloride of palm nut fatty acids in the presence of anhydrous sodium carbonate, and the product alkylated with dimethyl sulphate. The product is freely water soluble with a very high capillary activity. The palm nut fatty acids may be replaced by coconut fatty acids and the dimethyl sulphate may be replaced by diethyl sulphate. (4) Ethyl - phenyl biguanide is reacted as in example (1) with palm nut fatty acid chloride, and the product methylated with dimethyl sulphate. (5) Methyl phenyl biguanide is reacted with naphthenic acid chloride and the product treated with dimethyl or diethyl sulphate as described in examples 1 and 2. (6) Methyl phenyl biguanide is reacted with fencholic acid chloride, and then treated with dimethyl sulphate. (7) Methyl phenyl biguanide is treated with technical stearic acid chloride and the product reacted with epichlorhydrin to give a chlorine free water soluble product. The products of the invention are stable towards lyes and salts which cause hardness in water, and have a high capillary activity, and are useful as textile assistants, and as stripping and levelling agents in vat dyeing.