Patent GB-536047-A (GB)
Title: Process for the production of colourless halogen substituted urea sulphonic acids, and the resulting products
IPC: C07D327/08
Filed: 1939-06-15
Abstract: 536,047. Halogenated urea sulphonic acids. GEIGY AKT.-GES., J. R. June, 15, 1939, Nos. 50/41 and 51/41. Convention dates, June 16, 1938 and Dec. 31, 1938. Divided out of 536,011. Samples furnished. [Class 2 (iii)] [Also in Group VIII] Colourless halogen-substituted urea sulphonic acids of the benzene series are made by treating with a carbonic acid halide or an isocyanate a colourless monoamine or monoamino sulphonic acid of the benzene series, which in the case of polynuclear compounds contains directly linked benzene nuclei, or benzene nuclei linked by O, S, SO, SO 2  NH. CH 2 , CONH or NH-CO-NH, the components being so selected that the products contain at least one halogen atom and one sulphonic group ; alternatively these may be introduced by subsequent halogenation or sulphonation. Heterocyclic compounds of the general formula where X is a direct linkage or O, and Y is O or S, may also be used as parent materials. The carbamic acid chlorides and isocyanates employed may be made by known processes from primary or secondary aliphatic, araliphatic or aromatic amines, e.g. aniline, p-toluidine, chloranilines, 3-chlor-4-methyl-6-methoxy-aniline, 4-nitraniline, ethylaniline, 4-laurylaniline, laurylphenylamine, diphenylamine, 4:4'-dichlor- 2 - aminodiphenylether, 4<SP>1</SP> - chlor - 4 - aminodiphenylsulphone, laurylamine, α-dodecylbenzylamine &c. A large number of amines and aminosulphonic acids of the benzene series is specified, including diphenyls, diphenylethers, diphenylmethane, diphenylsulphides, diphenylsulphones, diphenylamines, benzanilides, diphenylureas, and simple benzene compounds such as aniline, anisidine or nitraniline. The products are useful for moth-proofing wool and other substances, and as disinfectants, bactericides &c. In examples, (1) 4-amino-4<SP>1</SP>-chlor- 1:1<SP>1</SP>-diphenylether is condensed with 3:4- dichlorphenylisocyanate ; (2) 2-amino-4:4<SP>1</SP>- dichlor -1 : 1<SP>1</SP> - diphenylmethane -2<SP>1</SP>- sulphonic acid (Specification 536,011) is condensed With 3:4-dichlorphenylisocyanate; other isocyanates, such as the2-,3-and 4-chlor-, 4-nitro-, 2:4- and 2:5- dichlor-, and 2:4:5- and 3:4:5- trichlorphenylisocyanate may be used ; (3) 2- amino-4:4<SP>1</SP>-dichlor-1:1<SP>1</SP>-diphenylether-2<SP>1</SP>-sul - phonic acid is condensed with 3:4-dichlorphenylcarbamic chloride ; a long list of other aminochlordiphenylether sulphonic acids which may be used is given; (4) 1-amino-3:4-dichlorbenzene-6-sulphonic acid is condensed with 3 : 4 - dichlorphenylcarbamic chloride ; (5) metanilic acid is condensed with 3-chlor-6- (41 - chlorplenoxy) - phenylcarbamic chloride (made from 2-amino-4:4<SP>1</SP>-dichlor-1:1<SP>1</SP>-diphenylether and phosgene) ; (6) m-aminobenzoyl-3:4- dichloraniline-6-sulphonic acid (made by condensing 3-nitrobenzoyl chloride with 1- amino - 3 : 4 - dichlorbenzene - 6 - sulphonic acid and reducing) is condensed with 3:4- dichlorphenylcarbamic chloride ; (7) 4-amino- 4<SP>1</SP>-amyl-1:1<SP>1</SP>-diphenylether-2-sulphonic acid is condensed with 3:4-dichlorphenyl isocyanate; a long list of other aminodiphenylether sulphonic acids which may be used is given, and (8) 2-amino-4:4<SP>1</SP>-dichlor-1<SP>1</SP>1<SP>1</SP>-diphenylether- 2<SP>1</SP>-sulphonic acid is condensed with 2:5-dichlorphenylcarbamic chloride or diphenylcarbamic chloride or N-laurylphenylearbamic chloride. Samples have been furnished under Sect. 2 (5) of the products from (1) 4-chlor-3<SP>1</SP>- aminodiphenyleneoxide sulphonic acid and 3:4-dichlorphenylcarbamic chloride; (2) 1- amino-3:4-dichlorbenzene-6-sulphonic acid and 4-chlor-3<SP>1</SP>-diphenyleneoxide-isocyanic ester ; (3) 3-aminophenothioxine sulphonic acid and 3 : 4 : 5 - trichlorphenyl isocyanate ; (4) phenothioxine isocyanate and 1-amino-3:4- dichlorbenzene - 6 - sulphonic acid ; and (5) 31- methyl - 4<SP>1</SP> - aminodiphenylether - 2 - sulphonic acid and.3 : 4 - dichlorphenyl isocyanate, the product being chlorinated.