Patent GB-779818-A (GB)
Title: New monoazo-dyestuffs and process for making them
IPC: C09B62/53
Filed: 1954-01-21
Abstract: 1 - Phenyl - 3 - methyl - 5 - pyrazolone - 31-(N - benzenesulphonyl) - sulphonamide is prepared by diazotizing 3 - aminobenzene - 1 - (N-benzenesulphonyl) sulphonamide, reducing the diazo compound with sodium bisulphite and condensing with ethyl acetoacetate.  1-Phenyl-3 - methyl - 5 - pyrazolone - 41 - (N - ethane-sulphonyl) - sulphonamide and 1 - phenyl - 3-phenyl - 3 - methyl - 5 - pyrazolone - 21 - chloro-51 - (N - benzenesulphonyl) - sulphonamide are prepared similarly. 2-Amino-8-naphthol-6-(N-benzenesulphonyl)-sulphonamide is prepared by reacting 1 : 7 - dihydroxynaphthalene - 3 - (N-benzenesulphonyl) - sulphonamide with ammonia under pressure.ALSO:The invention comprises monoazo dyestuffs from benzenic diazo components, which dyestuffs contain a monoacylated sulphonamide group and a group of formula: <FORM:0779818/IV(b)/1> where R is an aliphatic residue, n is 1 or 2, and X is a halogen atom in the b - or g -position of R, the monoacylated sulphonamide group and the group of the stated formula being present, one in the residue of the diazo component and the other in the residue of the coupling component. The preferred dyestuffs contain the group of the stated formula in the diazo component and the monoacylated sulphonamide group in the coupling component. Specified acyl residues which may be present in the monoacylated sulphonamide group are acetyl, n-butyryl, benzoyl, para-tert.-butyl or - chloro - benzoyl, and methane- or ethane - or n - butane - or benzene - or p - toluene - or o - or p - chlorobenzene - or dichlorobenzene - sulphonyl.  The dyestuffs may be further substituted by, for example, halogen atoms and nitro, acylamino, alkyl or alkoxy groups.  The dyestuffs are prepared by coupling the appropriate components in known manner in a not strongly alkaline medium.  Specified diazo components are 1 - aminobenzene - 3 - or - 4 - (N - acetyl) - sulphonamide, 4 - methyl - or - methoxy - 1 - aminobenzene - 3 - (N - benzoyl) - sulphonamide, 1 - aminobenzene - 2 - (N - methanesulphonyl) - sulphonamide, 1 - aminobenzene - 2 - or - 3 - or 4 - (N - p - toluenesulphonyl) - sulphonamide, 2 - chloro - or - methyl - 1 - aminobenzene - 5 - (N - benzenesulphonyl) - sulphonamide, 4 - methyl - 1 - aminobenzene - 2 - (N - benzenesulphonyl) - sulphonamide, 1 - amino - 2 : 6 - dichlorobenzene - 4 - (N - benzenesulphonyl) - sulphonamide, 1 - aminobenzene - 4 - (b  - chloroethyl) - or - (g  - chloro - b  - hydroxypropyl) - or - (g  - chloropropyl) - sulphonamide, 1 - aminobenzene - 3 : 5 - di - (b  - chloroethyl) - sulphonamide, 4 - methyl - 1 - aminobenzene - 3 - (b  - chloro - or - bromo - ethyl) - sulphonamide, 2 : 5 - or 2 : 6 - dichloro - 1 - aminobenzene - 4 - (b  - chloroethyl) - sulphonamide, 2 - methoxy - 1 - aminobenzene - 5 - b  - chloroethylsulphone and 1 - aminobenzene - 2 - or - 3 - or - 4 - b  - chloroethylsulphone. Specified coupling components are 1 - naphthol - 4 - or - 5 - (N - acetyl or - benzenesulphonyl) - sulphonamide, 2 - naphthol - 3 - or - 4 - or - 5 - or - 6 - or - 7 - or - 8 - (N - benzoyl) - sulphonamide, 8 - hydroxyquinoline - 5 - (N - p - toluenesulphonyl) - sulphonamide, 2 - aminonaphthalene - 6 - (N - benzenesulphonyl) - sulphonamide, 2 - amino - 8 - naphthol - 6 - (N - p - toluenesulphonyl or - benzenesulphonyl or - 21 : 51 - dichlorobenzoyl) - sulphonamide, 1 - (a  - naphthyl) - 3 - methyl - 5 - pyrazolone - 41 - (N - acetyl) - sulphonamide, 1 - phenyl - 3 - methyl - 5 - pyrazolone - 21 - or - 31 - or - 41 - (N - p - toluenesulphonyl or - 211 : 511 - dichlorobenzenesulphonyl or - benzenesulphonyl or - p - chlorobenzenesulphonyl) - sulphonamide, 1 - phenyl - 3 - methyl - 5 - pyrazolone - 21 - chloro - 51 - (N - benzenesulphonyl) - sulphonamide, 1 - phenyl - 3 - methyl - 5 - pyrazolone - 21 : 61 - dichloro - 41 - sulphonic acid - (N - benzenesulphonyl) - sulphonamide, 1 - acetoacetylaminobenzene - 2 - or - 3 - or - 4 - (N - benzoyl or - benzenesulphonyl) - sulphonamide, 2 - aminonaphthalene - 6 - (b  - chloroethyl) - sulphonamide, 1 - naphthol - 4 - or - 5 - (b  - chloroethyl) - sulphonamide, 2 - naphthol - 6 - (b  - chloroethyl) - sulphonamide or - sulphone, 1 - phenyl - 3 - methyl - 5 - pyrazolone - 21 - or - 31 - or - 41 - (b  - chloroethyl) - sulphonamide, 1 - phenyl - 3 - methyl - 5 - pyrazolone - 31 - (g  - chloropropyl) - sulphonamide and 1 - phenyl - 3 - methyl - 5 - pyrazolone - 31 - b  - chloroethyl - sulphone.  The dyestuffs may be used for dyeing or printing leather, silk, wool, superpolyurethanes and superpolyamides.  They dye wool in yellow and red tints.  In examples monoazo dyestuffs as defined above are prepared using certain of the components specified and the following additional components, diazo components:-2 - methoxy - 1 - amino - benzene - 5 - (b  - chloroethyl) - sulphonamide, 4 - methyl - 1 - aminobenzene - 3 - (a  - ethyl - b  - chloro - ethyl) - sulphonamide, 4 - methyl - 1 - aminobenzene - 3 - (41 - b  - chloroethyl - sulphonamido-phenyl) - sulphonamide and 2 - methoxy - 1 - aminobenzene - 4 - (g  - bromopropyl) - sulphonamide; coupling components:-1 - phenyl - 3 - methyl - 5 - pyrazolone - 31 - or - 41 - (N - ethanesulphonyl) - sulphonamide, 1 - phenyl - 3 - methyl - 5 - pyrazolone - 41 - chloro - 31 - (N - benzenesulphonyl) - sulphonamide, 1 - phenyl - 3 - methyl - 5 - pyrazolone - 31 - (N - 311 : 411 - dichlorobenzenesulphonyl or - acetyl - sulphonamide and 1 : 7 - dihydroxynaphthalene - 3 - (N - benzenesulphonyl) - sulphonamide.