Patent GB-536901-A (GB)
Title: Process for the production of halogen substituted aminoaryl sulphonic acid derivatives, and the resulting products
IPC: C07C309/45
Filed: 1939-12-22
Abstract: 536,901. Aminoarylsulphonic acid derivatives. GEIGY AKT.-GES., J. R. Dec. 22, 1939, Nos. 32735 and 32736. Convention dates, Dec. 24, 1938 and Dec. 31, 1938. [Classes 2 (iii) and 15 (ii)] [Also in Group VIII] Halogen-substituted acylated aminoaryl sulphonic acid derivatives are made by reacting a monoaminosulphonic acid of the general formulawhere X represents O, S, SO, SO  2 , CH 2 , CO or NH-CO-NH, and no water-solubilizing groups other than SO  3 H are present, with an aromatic, araliphatic or aliphatic monoacylating agent containing at least 7 carbon atoms or with an acylating agent of the group of polycarboxylic acids, and introducing at least one halogen atom into the product, either by using halogenated reaction components or by halogenating the product. Unsulphonated monoamines may be used as parent materials, the sulphonic acid groups being introduced by sulphonating the products. Parent materials include halogen and alkyl substituted derivatives of sulphonic acids of aminodiphenyl-, ethers, sulphides, sulphoxides, sulphones, methanes, ketones and ureas, a large number of such compounds being specified. Acylating agents include the following acids and their esters and halides;-capric, lauric, myristic, palmitic; stearic, fatty acid mixtures, e.g. fish oil and palm kernel fatty acids, phenylacetic, 2- or 4-halogenphenylacetic, cinnamic, hydrocinnamic, phenoxyacetic, halogen substituted phenoxy acetic, benzoic, 2:4 or 3:4-dichlorbenzoic acids and 3:4-dichlorbenzene sulphonic chloride. In examples : (1) 4- amino-4<SP>1</SP>-chloro-5<SP>1</SP>-methyl-1:1<SP>1</SP>-diphenylether- 2-sulphonic acid is acylated with palm kernel fatty acid chloride, a large number of other halogenated aminodiphenylether 'sulphonic acids which may be used is specified ; these are made by condensing various o- or p-chloronitrobenzene sulphonic acids with phenols and reducing; (2) sodium 2-amino-4:4<SP>1</SP>-dichloro-1:1<SP>1</SP>-diphenylether-2<SP>1</SP>-sulphonate is ocylated with 4-chlorophenylacetyl chloride ; (3) 4-amino - 4<SP>1</SP>:5<SP>1</SP>-dichlorodiphenyl-sulphide-2- sulphonic acid (made by condensing 3:4-dichlorothiophenol with p-chloronitro benzene sulphonic acid and subsequent reduction) is acylated with palm kernel fatty acid chloride ; numerous other halogenated aminodiphenylsulphide-2-sulphonic acids may be similarly treated; (4) 2-amino-4:4<SP>1</SP>-dichloro-1:1<SP>1</SP>-diphenyl - ether-2'-sulphonic acid is .acylated with succinic acid dichloride, or a dihalide of adipenic acid, terephthalic acid, or phthalic acid (5) 2-amino-4:4<SP>1</SP>-dichloro-1:1<SP>1</SP>diphenylether-2<SP>1</SP>- sulphonic acid is acylated with 3:4-dichlorobenzoyl chloride, and (6) 3-methyl-4-amino-1:11- diphenylether-2-sulphonic acid is acylated with palm kernel fatty acid chloride and the product is chlorinated. The products are suitable for moth-proofing wool, featbers, fur, hair, textile fabrics &c., and are also useful as disinfectants. bactericides, fungicides and insecticides, and as wetting and penetrating agents. The Specification as open to inspection under Sect. 91 comprises also the use as parent materials of compounds of the above general formula in which X represents any divalent atom or group, including aminodiphenylamines. It also comprises the subject-matter of Specification 537,173. This subject-matter does not appear in the Specification as accepted.