Patent GB-469763-A (GB)
Title: The manufacture of acid wool dyestuffs
IPC: C09B51/00
Filed: 1935-12-24
Abstract: Acid wool dyestuffs are made by condensing compounds having the formul  <FORM:0469763/IV/1> wherein Y is halogen or alkoxy, X is an alkyl, aryl or cycloalkylsulphone group or an alkyl, aryl or cycloalkyl ketone group and Z is SO2, CO, SO2--aryl--SO2 or OC--aryl--CO, with amino compounds having the formula R1NHR2NH2 wherein R1 is aryl or cycloalkyl R2 is aryl and R1 and/or R2 contains a sulphonic acid group or with an aminocarbazolsulphonic acid.  In examples: (1) 4-aminodiphenylamine-2-sulphonic acid is condensed with 1 - chlor - 2 - nitrobenzene - 4 - ethylsulphone, 1-chlor-2-nitrobenzene-4-propylsulphone, 1-chlor-2-nitrobenzene-4-butylsulphone, 1 : 6-dichlor-2 - nitrobenzene - 4 - methylsulphone, 4 : 4<1>-dichlor-3 : 3<1>-dinitrodiphenylsulphone, naphthalene - 1 : 5 - di(3<1> - nitro - 4<1> - chlorphenyl)-sulphone, 4-chlor-3-nitroacetophenone, 4 : 4<1>-dichlor - 3 : 3<1> - dinitrobenzophenone, 4 : 4<1>-dichlor - 3 : 3<1> : 5 : 5<1> - tetranitrobenzophenone and with 1 : 4-di(4<1>-chlor-3<1> : 5<1>-dinitrobenzoyl)-benzene; the use of 4<1>-methoxy or ethoxy-4-aminodiphenylamine-2-sulphonic acid, 4-amino-4<1> - acetylaminodiphenylamine - 2 - sulphonic acid, 1 - amino - 4 - cyclohexylaminobenzene-3-sulphonic acid, 1-amino-4-naphthylaminobenzene - 3 - sulphonic acid, 3<1> : 4<1>-dimethoxy - 4 - aminodiphenylamine-2-sulphonic acid instead of the first mentioned component gives similar dyestuffs; (2) 3-aminocarbazol-6-sulphonic acid is condensed with 1-chlor-2-nitrobenzene-4-methyl (ethyl, propyl or butyl) sulphone and 3 - amino - N - ethylcarbazole - 6 - sulphonic acid with 1-chlor-2-nitrobenzene-4-ethyl or butyl sulphone; (3) 4<1>-methoxy-4-aminodiphenylamine-2-sulphonic acid is condensed with 4 : 4<1>-dichlor - 3 : 3<1> - dinitrodiphenylsulphone, 3 : 3<1>-dinitro - 4 : 4<1> : 5<1> - trichlordiphenylsulphone and 3 : 3<1>-dinitro-5-methyl-4 : 4<1> : 5<1>-trichlor diphenylsulphone; the use of 4<1>-ethoxy-4-aminodiphenylamine - 2 - sulphonic acid and 3<1> : 4<1>-dimethoxy-4-aminodiphenylamine-2-sulphonic acid in these reactions is mentioned; (4) 4<1> - ethoxy - 4 - aminodiphenylamine - 2 - sulphonic acid is condensed with 1 : 4-di(4<1>-chlor-3<1>-nitrobenzoyl)benzene.  By replacing the chlorine atom by the methoxy group in, for example, 1-chlor-2-nitrobenzene-4-ethylsulphone the same dyestuffs are produced.  Specification 467,549 is referred to.  Samples have been furnished under Sect. 2 (5) of dyestuffs obtained by condensing 2<1>-methoxy-4-aminodiphenylamine-2-sulphonic acid with 1 - chlor - 2 - nitrobenzene - 4 - cyclohexylsulphone and 4-aminodiphenylamine-2-sulphonic acid with 1-chlor-2-nitrobenzene-4-phenyl sulphone.  Thirteen further samples have been filed of dyestuffs prepared according to the detailed examples.  4-Chlor-3-nitroacetophenone is prepared by nitrating the parent chloracetophenone.  1 : 4-Di-(4<1>-chlor-3<1>-nitro (or 3<1> : 5<1>-dinitro) benzoyl) benzene is prepared by condensing terephthaloylchloride with chlorbenzene and nitration. 1-Chlor-2-nitrobenzene-4-cyclohexylsulphone is prepared by treating p-chlorphenyl mercaptan with cyclohexylchloride, oxidizing the product and then effecting nitration.