Patent GB-757368-A (GB)
Title: Photographic silver halide emulsions containing colour couplers and the method of producing coloured photographic images therein
IPC: G03C7/32
Filed: 1954-03-24
Abstract: 1 - Hydroxy - 4 - chloro - N - (b  - {4 - [2 - (2:4 - di - tert - amylphenoxy) - 5 - (3:5 - di - b  - hy - droxyethylsulphamylbenzamido) - benzamido] - phenyl} - ethyl) - - naphthamide is prepared by reacting 1 - hydroxy - 4 - chloro - N - (b - {4-[2-(2:4 - di - tert. - amylphenoxy) - 5 - (3:5 - di - chlorosulphonylbenzamido) - benzamido] - phenyl} - ethyl) - 2 - naphthamide with a large excess of ethanolamine in dioxane. 1-Hydroxy-4 - chloro - N - (b  - {4 - [2 - (2:4 - di - tert.-amylphenoxy) - 5 - {3:5 - [di - (di - b  - hydroxyethyl - sulphamyl)]} - benzamido] - phenyl} - ethyl) - 2 - naphthamide, 1 - hydroxy - 4 - chloro - N - (b -{4-[2 - (2:4 - di - tert. - amylphenoxy) - 5 - (3:5-bis-{N - [tri - (hydroxymethyl) - methyl] - sulphamyl}-benzamido) - benzamido] - phenyl} - ethyl) - 2 - napthamide, 1 - hydroxy - 4 - chloro - N - (b -{4-[2 - (2:4 - di - tert. - amylphenoxy) - 5 - (3:5-bis-{N - [a :a  - di - (hydroxymethyl) - ethyl] - sulphamyl) - benzamido) - benzamido] - phenyl}-ethyl) - 2 - naphthamide, 1 - hydroxy - 4 - chloro - N - [b - { 3 - [bis - (b  - hydroxyethyl)-sulphamyl]-benzamido} - ethyl] - 2 - naphthamide, 1 - hydroxy - N - (b  - {4 - [2 - (2:4 - di - tert. - amylphenoxy) - 5 - (m - [tris - {N - [hydroxymethyl] - methyl] - sulphamyl} - benzamido) - benzamido] - phenyl} - ethyl) - 2 - naphthamide, 1 - hydroxy - 4-chloro - N - [b  - (4 - {2 - [2:4 - di - tert. - amyl - phenoxy] - 5 - [3 - (b  - hydroxyethylsulphamyl) - benzamido] - benzamido} - phenyl) - ethyl] - 2 - naphthamide, 1 - hydroxy - 4 - chloro - N - {b -(4-[5 - {3 - [bis - (b  - hydroxyethyl) - sulphamyl] - benzamido} - 2 - (2:4 - di - tert. - amylphenoxy) - benzamido] - phenyl) - ethyl} - 2 - naphthamide, 1 - hydroxy - 4 - chloro - N - [b  - {2 - (2:4 - di - tert. - amylphenoxy) - 5 - [3 - (b  - hydroxyethylsul - phamyl) - benzamido] - benzamido} - ethyl] - 2 - naphthamide, 1 - hydroxy - 4 - chloro - N - {b -[5-{3 - [bis - (b  - hydroxyethyl) - sulphamyl] - benz - amido} - 2 - (2:4 - di - tert. - amylphenoxy)-benz-amido] - ethyl} - 2 - naphthamide, 2:4 - dichloro-6 - {2 - [2:4 - di - tert. - amylphenoxy) - 5 - [3-(b -hydroxyethylsulphamyl) - benzamido] - benzamido } - 3 - methylphenol, 2:4 - dichloro - 6 - {2-[2:4-di - tert. - amylphenoxy] - 5 - [3 - (di - b -hydroxyethylsulphamyl) - benzamido] - benzamido} - 3 - methylphenol, 6 - [2 - (2:4 - di - tert. - amyl - phenoxy) - 5 - {3 - [tris - (hydroxymethyl)-methylsulphamyl] - benzamido} - benzamido] - 2:4 - di - chloro - 3 - methylphenol, 1 - phenyl - 3 - {3-[2-(2:4 - di - tert. - amylphenoxy) - 5 - (3:5 - di - b  - hydroxyethylsulphamylbenzamido) - benzamido] - benzamido} - 5 - pyrazolone, 1 - phenyl - 3 - }3 - [5 - {3:5 - bis - [tris - (hydroxymethyl) - methyl]-sulphamylbenzamido} - 2 - (2:4 - di - tert. - amyl - phenoxy) - benzamido] - benzamido} - 5 - pyrazolone, 1 - phenyl - 3 - {3 - [2 - (2:4 - di - tert.-amylphenoxy) - 5 - (3 - [tris - (hydroxymethyl) - methyl - sulphamyl] - benzamido) - benzamido] - benz - amido} - 5 - pyrazolone, 1 - phenyl - 3 - {3 - [5 - {3 - [bis - (b  - hydroxyethyl) - sulphamyl] - benz - amido} - 2 - (2:4 - di - tert. - amylphenoxy - benzamido] - benzamido} - 5 - pyrazolone, 1-phenyl - 3 - [3 - {2 - [2:4 - di - tert. - amylphen - oxy] - 5 - [3 - (b  - hydroxyethylsulphamyl) - benz - amido] - benzamido} - benzamido] - 5 - pyrazolone, (2 - methoxybenzoyl) - 4 - [5 - {3 - [bis - (b  - hy - droxyethyl) - sulphamyl] - benzamido} - 2 - (2:4 - di - tert. - amylphenoxy) - benzamido] - acetanilide, and (2 - methoxybenzoyl) - 4 - {2 - [2:4 - di-tert.-amylphenoxy] - 5 - [3 - (b  - hydroxyethylsul - phamyl) - benzamido] - benzamido} - acetanilide are similarly prepared.  1 - Phenyl - 3 - [3 - (b  - hydroxyethylsulphamyl)-benzamido] -5-pyrazolone is prepared by reacting 1 - phenyl - 3 - (3 - chlorosulphonylbenzamido)-5 - (3 - chlorosulphonylbenzoxy) - pyrazole in dioxane with ethanolamine and pyridine, and heating an ethanol solution of the product with aqueous sodium hydrosulphite.  1-Phenyl-3-{3-[bis - (b  - hydroxyethyl) - sulphamyl] - benzamido}-5-pyrazolone is similarly prepared.  1 - Hydroxy - 4 - chloro - N - (b  - {4 - [2 - (2:4-di - tert. - amylphenoxy) - 5 - (3:5 - dichlorosul - phonylbenzamido) - benzamido] - phenyl}-ethyl)-2-naphthamide is prepared by reacting together 1 - hydroxy - 4 - chloro - N - (b  - (4 - (2 - (2:4-ditert. - amylphenoxy) - 5 - aminobenzamido-phenyl) - ethyl) - 2 - naphthamide and 3:5 - di - chlorosulphonylbenzoyl chloride in dioxane in presence of quinoline.  1 - Hydroxy - N - (b -{4-[2-(2:4 - di - teert. - amylphenoxy) - 5 - (3 - chloro - sulphonylbenzamido) - benzamido] - phenyl}-ethyl) - 2 - naphthamide, 1 - hydroxy - 4 - chloro-N - {b  - [2 - (2:4 - di - tert. - amylphenoxy) - 5 - (3 - chlorosulphonylbenzamido) - benzamido] - ethyl} - 2 - naphthamide, 6 - [5 - (3 - chlorosulph - onylbenzamido) - 2 - (2:4 - di - tert. - amylphen - oxy) - benzamido] - 2:4 - dichlor - 3 - methyl - phenol, 1 - phenyl - 3 - {3 - [2 - (2:4 - di - tert. - amylphenoxy) - 5 - (3:5 - dichlorosulphonylbenz - amido) - benzamido] - benzamido} - 5 - pyrazolone, the corresponding 3-chlorosulphonyl compound, and (2 - methoxybenzoyl) - 4 - [5 - (3 - chlorosul - phonylbenzamido) - 2 - (2:4 - di - tert. - amyl - phenoxy)-benzamido]-acetanilide are similarly prepared.  1 - Hydroxy - 4 - chloro - N - (b  - {4 - [2 - (2:4-di - tert. - amylphenoxy) - 5 - aminobenzamido]-phenyl} - ethyl) - 2 - naphthamide is prepared by reducing with hydrogen the corresponding 5-nitrobenzamido compound, itself prepared by reacting 1 - hydroxy - 4 - chloro - [b  - (4 - amino - phenyl) - ethyl] - 2 - naphthamide with 2-(2:4-di - tert. - amylphenoxy) - 5 - nitrobenzoyl chloride.  1 - Hydroxy - 4 - chloro - N - {b  - [2 - (2:4 - di - tert. - amylphenoxy) - 5 - aminobenz - amido] - ethyl} - 2 - naphthamide and 1-phenyl-3 - {3 - [2 - (2:4 - di - tert. - amylphenoxy) - 5 - amino] - benzamido} - benzamido - 5 - pyrazolone and the corresponding nitro compounds are similarly prepared.  1 - Hydroxy - 4 - chloro - N - [b  - (4 - amino - phenyl) - ethyl] - 2 - naphthamide is prepared by reducing with hydrogen 1-hydroxy-4-chloro-N-(b  - (4 - nitrophenyl - ethyl) - 2 - naphthamide, itself prepared by heating together 4-nitro-b -phenethylamine and phenyl 1 - hydroxy - 4 - chloro-2-naphthoate. 1-Hydroxy - 4 - chloro - N - [b  - (3 - chlorosul - phonylbenzamido)-ethyl]-2-naphthamide is prepared by refluxing with m-chlorosulphonylbenzoyl chloride and dioxane 1-hydroxy-4-chloro - 2 - b  - aminoethylnaphthamide, itself prepared by reacting phenyl 1-hydroxy-4-chloro-2-naphthoate with ethylenediamine in benzene.  2:4 - Dichloro - 3 - methyl - 6 - [3 - amino - 6 - (2:4-di-tert.-amylphenoxy) - benzamido] - phenol is prepared by reducing with iron and acetic acid the corresponding 3-nitro compound, itself prepared by reacting 2-amino-4:6-dichloro-5-methylphenol hydrochloride with 2-(2:4-di-tert.-amylphenoxy)-5-nitrobenzoyl chloride.  4-(2 - Methoxybenzoylacetamido) - 2 - (2:4 - di-tert.-amylphenoxy)-5-aminobenzanilide and the corresponding 5-nitro compound are similarly prepared.  1 - Phenyl - 3 - (3 - chlorosulphonylbenzamido)-5 - (3 - chlorosulphonylbenzoxypyrazole is prepared by heating together 1-phenyl-3-amino-5-pyrazolone and m - chlorosulphonylbenzoyl chloride in ethyl oxalate.  Specifications 531,246, 664,580, [both in Group IV], and 711,488, [Group IV (a)], are referred to.