Patent GB-625664-A (GB)
Title: Photographic colour developers comprising arylsulphon-hydrazides
IPC: G03C7/30
Filed: 1946-01-14
Abstract: b -Aromatic sulphonhydrazides are obtained by reducing the corresponding diazo-sulphones, which are themselves obtained by reacting diazonium compounds with sulphinic acids.  2 : 5 - Diethoxy - 4 - benzamidobenzenediazo-(p-acetamidophenyl)-sulphone is prepared by reacting diazotized 2 : 5-diethoxy-4-benzamidoaniline with p-acetamidobenzenesulphinic acid.  2 : 5 - Diethoxy - 4 - benzamidophenyl) - p-acetamidobenzenesulphonhydrazide is prepared by adding zinc dust to a solution of 2 : 5-diethoxy - 4 - benzamidobenzenediazo - (p-acetamidophenyl)-sulphone in acetone, acetic acid, and water.  b  - Phenyl - 3 - carboxybenzenesulphonhydrazide is prepared by reacting phenylhydrazine with 3-chlorosulphonylbenzoic acid.  b -Phenylethane-, b -phenyldodecane, b -(p-octadecylphenyl)-methane-, b -(4-diethylaminophenyl)-ethane-, b -(3-acetamidophenyl)-, methane-, b -phenylmethane-, b -(31-methoxyphenyl)-methane-, b  - (41 - diethylaminophenyl) - ethane -, b  - (41-aminophenyl) - butane - , b - (31 - acetamidophenyl) - methane -, b  - (31 - phenylsulphonamidophenyl) - methane -, b  - phenylbenzene -, b  - (41 - methylphenyl) - benzene -, b  - phenyl - 3-nitrobenzene -, b  - (41 - ethoxyphenyl) - benzene -, b  - (11 - naphthyl) - 4 - acetamidobenzene -, b -(21 : 51 - dimethoxy - 41 - benzamidophenyl)-benzene -, b  - (21 : 41 - dimethylphenyl) - benzene - b  - (41 - methoxyphenyl) - 4 - chlorobenzene -, b  - (phenyl) - 4 - methylbenzene -, b  - (phenyl) - 4-ethoxybenzene -, b  - (phenyl) - 4 - octadecyl-benzene -, b  - (41- phenylaminophenyl) - benzene -, b - (41 - dodecylphenyl) - benzene -, b  - (phenyl)-4 - sulphobenzene -, b  - (41 - octyloxyphenyl)-benzene -, b  - (4 - diphenyl) - methane -, b  - (4-diphenyl) - benzene -, b  - phenyl - 4 - hydroxy-benzene -, b  - phenyl - 4 - diphenyl -, and b -phenyl - naphthalene - sulphonhydrazides and b  : b  - (di - p - acetamidophenylsulphonyl) - 3 : 31-dimethoxy - 4 : 41 - dihydrazinodiphenyl and b  : b 1 - (di - p - acetamidophenylsulphonyl)-3 : 31 - dimethyl - 4 : 41 - dihydrazinodiphenyl are similarly prepared. p-Octadecylphenylhydrazine is prepared by reacting diazotized p-octadecylaniline with sodium sulphite.  p-Dodecylphenylhydrazine is similarly prepared.  Butanesulphinic acid is prepared by reacting butyl alcohol with thiorurea in presence of HC2, treating with chlorine, and then with sodium sulphite.  p-Octadecylbenzenesulphoric acid is prepared by adding diazotized p-octadecylaniline to an aqueous solution of SO2 containing copper paste. p-Sulphophenylsulphinic acid is similarly prepared. p-Octyloxyphenylhydrazine is prepared by heating p-acetylaminophenol with octyl bromide in presence of sodium acetate, saponifying with alcoholic KOH, diazotizing, and reducing with sodium sulphite. p-Acetamidobenzenesulphinic acid is prepared by reacting acetanilide with chlorsulphonic acid and reducing with sodium sulphite. n-3-Octadecylamidobenzyl-H-acid is prepared by refluxing together 3-nitrobenzyl chloride, H-acids, sodium carbonate, calcium carbonate, and water, hydrogenerating, and heating the N-(3-aminobenzyl)-H-acid with octadecyl chloride in pyridine and dimethylformamide.