GB337860A - The manufacture of mono-oxamic acids of 4.4-diamino-diarylcyclohexane compounds and of dyestuffs derived therefrom - Google Patents

Abstract

337,860. Carpmael, A., (I. G. Farbenindustrie Akt.-Ges.). Aug. 20, 1929. Mono-oxamic acids of 4-4<1>-diaminodiaryl-1-1<1>- cyclohexane are made by heating the parent body with oxalic acid preferably in the presence of a solvent. Products are specified from 4-4<1>-diaminodiphenyl-1-1<1>-cyclohexane, 4-4<1>-diamino-8- 3<1>-dimethyldiphenyl-1-1<1>-cyclohexane, 4 - 4<1> - di amino-3-3<1>-dimethoxy-1-1<1>-cyclohexane, 4-4<1>-diamino-3-3<1>-diethoxy-1-1<1>-cyclohexane, 4 - 4<1> - diamino-3-3<1>-dichloro-1-1<1>-cyclohexane, 4 - 4' - diamino-3-3<1>-dibromo-1-1<1>-cyclohexane and 4-4'-diamino-3-3<1>-dimethyldipheny-4<11> - methyl - cyclohexane. Specification 313,421 is referred to. Azo-dyes are made by diazotizing and coupling, a mono-oxamic acid of 4-41-diaminodiphenyl-1-1'- eyclohexane with a component which may or may not be capable of further diazotization and coupling. The resulting dye can subsequently have the oxamic acid radical saponified off to give a further dye which can again be diazotized and coupled with a coupling component. In examples the following dyes are described : (6) 4-amino-3-3<1>- dichloro-diphenyl-1-1<1>-cyclohexane oxamic acid (or the corresponding 3-3<1>-dibromo compound) # 1-benzoylamino-8-hydroxynaphthalene-4-6-disulphonic acid or 1-benzoylamino-8-hydroxynaphthalene-3-6-disulphonic acid or 1-toluenesulphamino - 8-hydroxynaphthalene-3-6-disulphonic acid or other acylamino naphthol sulphonic acids. (8) 4 - amino- 3 -3<1>-dimethyldiphenyl-1-1<1>-cyclohexane-4'-oxamic acid # 2.8-dihydroxynaphthalene-6-sulphonic acid (sodium salt) this dye can either be saponfied with caustic soda or esterified with p-toluenesulphonyl chloride to give further dyes. (9) 4-aminodiphenyl-1-1<1>-cyclohexane-4<1>- oxamic acid # 1(2<1>-chloro-5<1>-sulphophenyl)-3- methyl-5-pyrazolone and saponified # 1-amino- 2-(4<1>nitrophenylazo)-8-hydroxynaphthalene - 3.6 - disulphonic acid. (10) 4-amino-3.3<1>-dimethyldiphenyl-1-1<1>-cyclohexane-4<1>-oxamic acid # 1- aminonaphthalene-7-sulphonic acid # 1-phenylamirionaphthalene-8-sulphonic acid or 2-(4<1>-aminophenylamino)-5-hydroxynaphthalene - 7-sulphonic acid. The latter dye is again diazotized and developed on the fibre with #-naphthol. (11) 4- amino-3.3<1>-dimethyldiphenyl-1-1<1>-cyclohexane - 4'- oxamic acid # 1-amino-2-(4<1>-nitrophenylazo)-8- hydroxynaphthalene-3-6-disulphonic acid. (12) 4- amino-3-3<1>-dimethyldiphenyl-1-1<1>-cyclohexane - 4'- oxamic acid # salicylic acid (or other components having a chromable group), saponified and # 1-(2<1>-chloro-5<1>-sulphophenyl)-3-methyl-5 pyrazolone or 1 - amino-2-(4'-nitrophenylazo)-8- hydroxynaphthaLene-3-6-disulphonic acid or 2- amino-8-hydroxy-naphthalen-6 - sulphonic acid. Specification 335,893 is referred to.