Patent GB-335893-A (GB)
Title: The manufacture of fast azodyestuffs
IPC: C09B35/02
Filed: 1929-04-30
Abstract: 335,893. Carpmael, A., (I. G. Farbenindustrie Akt.-Ges.). April 30, 1929. Samples furnished. Azo dyes are made by tetrazotizing a diamine of the general formula : NH2- R-R1-R-NH2 in which R = an aromatic and R, = a hydroaromatic residue all of which may be substituted or not and coupling with two molecular parts of the same or different coupling components and of which one may be a mouoazo compound or may be diazotized and coupled with a further component. Valuable dyestuffs are obtained by using as at least one component a naphthol sulphonic acid of the general formula in which A is hydrogen, OH, NH2, O-acyl (acyl representing e.g. benzenesulphonyl or other arylsulphonyl group), NH acyl (acyl representing e.g. acetyl, benzoyl, chloro- or dichlordbenzoyl or an arylsulphonyl group), B stands for hydrogen or when A = NH2, the group (-N=N-aryl), and n = 1 or 2. They dye wool and silk in varying shades and are fast to washing, milling and perspiration. In examples the following dyestuffs are described : (1) 4 : 4<1>-diamino-3 : 3<1>-dimethyldiphenyl-1 : 1<1>-cyolohexane # 2 : 8-dioxynaphthalene-6-sulphonic acid (2 mols.); the corresponding 3 : 3<1>-dimethoxy or 3:3<1>-diethoxy compounds of the diazo components and the monobenzenesulphonic ester of the coupling component are also specified; similar products are made by after-treating the first dyestuff with arylsulphochlorides; other components specified are : 4 : 4<1>-diaminodiphenyl-4<11>-methylcyclohexane, 4: 4<1>-diamino-3 : 3<1>-dimethoxydiphenylcyclohexane, 1-(4<1>-sulphophenyl)-3-methyl-5- pyrazolone, N-p-toluenesulpho H acid and N- benzoyl H acid, (2) 1-naphthol-3: 6-disulphonic acid # 4 : 4<1>-diaminodiphenylcyclohexane # 1-naphthol-4-sulphonic acid; other components are 2-naphthol-6: 8-disulphonic acid, N-phenyl 2 : 8 : 6-acid, 2-naphthol-7-sulphonic acid, phenol, 4-nitro-1: 3-diaminobenzene, and 1 :3-diaminobenzene-4-sulphonic acid, (3) salicyclic acid # 4 : 4<1> - diamino - 3 : 3<1> - dimethyldiphenylcyclohexane # II acid #p-nitraniline (yellowishgreen on wool when after-chromed); salicylic acid may be replaced by 1 : 8-aminonaphthol-4- sulphonic acid, 2 : 8-aminonaphthol-6-sulphonic acid, or 1-(4<1>-sulphophenyl)-3-methyl-5-pyrazolone, (4) 1-naphthol-4-sulphonic acid # 4 : 4<1>. diamino-3 : 3<1>-dimethyldiphenylcyclohexane # 2:8:6-acid # #-naphthol, (5) phenol # 4 : 4<1> - diamino - 3 : 3<1>-dimethoxydiphenylcyclohexane # H acid # 4-nitro-1: 3-diaminobenzene, (6) 4:4'-diamino-3:3'-dimethoxydiphenylcyclohexane # H acid (1 mol) # 4-nitro-1 : 3-diaminobenzene or phenol (2 mols.). Specification 313,421 is referred to. Monoarylsulphonic esters of 2 : 8-dioxynaphthalene-6-sulphonic acid are made (1) by treating 2 : 8-dioxynaphthalene-6-sulphonic acid with an arylsulphochloride. and subsequent saponification of the di-ester initially produced, or (2) by treating a 2-acylamino-8-naphthol-6-sulphonic acid with an arylsulphochloride, partially saponifying the 2-acylamino-8-arylsulphonaphthol-6-sulphonic acid thus formed and converting the 2-amino compound into the corresponding 2-hydroxy compound. The Provisional Specification specifies also azo dyestuffs containing components of the second general formula above in which A = O-acyl (acyl representing an acetyl, benzoyl, chloro- or dichlorobenzoyl group) and tetrakisazo dyestuffs.