Patent GB-537173-A (GB)
Title: Process for the production of halogen substituted aminoaryl sulphonic acid derivatives, and the resulting products
IPC: C07C309/46
Filed: 1939-12-22
Abstract: 537,173. Aminoarylsulphonic acid derivatives. GEIGY AKT.-GES., J. R. Dec. 22, 1939, Nos. 3868/41 and 3869/41. Convention dates, Dec. 24,1938, and Dec. 31,1938. Divided out of 536,901. [Classes 2 (iii) and 51 (ii)] [Also in Group VIII] Halogen-substituted aminoarylsulphonic acid derivatives are made by reacting a monoamino sulphonic acid of the general formula where X represents a divalent atom, e.g. O or S, or a divalent group, e.g. SO, SO  2 , CH 2 , CO, NH or NH-CO-NH, with an aralkylating agent, or with an. alkylating agent containing at least 7 carbon atoms, which may be substituted or contain a heteroatom or heteroatom group in the alkyl part, and introducing at least one halogen atom into the final compound, either by using a halogenated reaction component, or by halogenating the product. Unsulphonated parent materials may also be used, the sulphonic group being introduced by subsequent sulphonation. The products may be acylated, e.g. with acetic anhydride, if desired. The parent materials include aminodiphenyl-ethers, sulphides, sulphoxides, sulphones, methanes, ketones, amines and ureas, a large number of halogenated and sulphonated compounds of these groups being specified. The alkylating agents include those of the higher alcohols obtained by the reduction of fats, oil or resins, and also such compounds as chloromethyldodecylether, chloromethyldodecylthioether, and α-halogen carboxylic acids and theirsalts,estersand amides Aralkylating agents include benzyl and chloro- and bromo-benzyl halides, and di-, tri and tetrachlorobenzyl halides. In examples (1) 2- amino-4 : 4--dichloro-1<SP>1</SP>-diphenylmethane-2<SP>1</SP>- sulphonic acid (madebynitratingp-chlorobenzyl chloride; condensing with chlorobenzene with acid of aluminium chloride, and reducing) is treated with p-chlorobenzyl chloride, (2) 4- amino-4<SP>1</SP>-amyl-1 : 1<SP>1</SP>-diphenylether-2-sulphonic acid (made by condensing amylphenol with pcblornitrobenzene sulphonic acid and reducing) is treated with tetrachlorobenzyl chloride ; numerous other alkylated diphenylethersulphonic acids are specified, (3) 2-amino-4 : 4<SP>1</SP>-dichloro-. 1 : 1<SP>1</SP>-diphenylether-2<SP>1</SP>-sulphonic acid is condensed with chloracetic-3 : 4-dichloranilide, (4) 4-amino-4<SP>1</SP>-chloro-5<SP>1</SP>-methyl-1 : 1<SP>1</SP>-diphenylether-2-sulphonic acid is condensed with chloromethyldodecyl-ether or -thioether, (5) 4-amino- 5 5<SP>1</SP>-dichloro-1 : 1'-diphenylether is condensed with dodecylbromide and the product is sulphonated with sulphuric acid monohydrate, and (6) 2-amino-2<SP>1</SP>-: 4<SP>1</SP>: 5<SP>1</SP>-trichloro-1 : 1<SP>1</SP>-diphenylether-4-sulphonic acid is condensed with pchlorobenzyl chloride and the product acylated with acetic anhydride a large number of other aminodiphenylether sulphonic acids is specified. Other parent materials mentioned are 4-amino- 4<SP>1</SP> : 5<SP>1</SP>-dichloro-1 : 1<SP>1</SP> -diphenylamine-2-sulphonic acid, 4-amino-4<SP>1</SP>-chloro-1: 1<SP>1</SP>-diphenylsulphone-or-sulphoxide-2-sulphonic acid, 2- amino- 4: 4<SP>1</SP>-dichloro-1: 1<SP>1</SP>-diphenylurea-2<SP>1</SP>- sulphonic acid, and 4-chloro-41-aminodiphenylketone-3-sulphonic acid. The products are suitable for moth-proofing wool, feathers, fur, hair, textile fabrics, &c. and are also useful as disinfectants, bactericides, fungicides and insecticides, and as wetting and penetrating agents.