Patent GB-531312-A (GB)
Title: Improvements in and relating to colour forming developers and processes of colour development
IPC: G03C7/36
Filed: 1939-03-31
Abstract: 531,312. Photographic colour development. KODAK, Ltd. (Eastman Kodak Co). March 31, 1939, Nos. 13535/40, 13536/40 and 13537/40. Divided out of 531,246. [Class 98 (ii)] [Also in Group IV] A process of colour development comprises developing a reducible silver salt image with an aromatic amino developing agent in the presence of a colour coupler having the general formula Z-SO 2 -NXY, where X is a monovalent organic substituent containing a coupling function, Y is hydrogen or a monovalent organic substituent such as alkyl, and Z is a monovalent organic substituent not containing a coupling function and not constituting, when split off, a dye or leuco dye or a compound which gives a dye on oxidation. The colour coupler may be a sulphonyl derivative of a secondary amine, and Y and Z may be organic radicals not containing solubilizing groups. X may consist of a phenolic or naphtholic nucleus, for example an α- naphthol radical attached through the 3-, 4-, 5- or 6- position, the α-naphthol nucleus being unsubstituted or substituted for example by halogen, which may be in the same ring as the hydroxy group. Alternatively X may be an acylacetarylamide radical attached through the p-position in the aminoaryl nucleus or a cyanacetaryl or cyanacetaminoaryl radical or a pyrazolone or a barbituric acid radical. Z may comprise an aryl nucleus, which may contain an aliphatic nucleus of low or high molecular weight. The colour coupler may be resistant to diffusion, such as 4-(p-laurylbenzenesulphonamino)-w-benzoylacetanilide. Numerous examples of colour couplers are specified. Specifications 427,472, 427,516, 427,518, 427,520, 440,032, 440,089, 447,092, 458,664, 499,185, 500,611, 500,718, 500,826, 503,752, 503,814, 503,817, 503,818, 503,819, 503,820, 503,821, 503,939, 503,940, 524,154, 524,554, 524,555, 527,493 are referred to. 5-Alkyl-(or aryl)-sulphonamido-1-naphthols are prepared by the reaction of 5-amino-1- naphthol with an alkyl or aryl sulphonic acid chloride in acetic acid solution in the presence of sodium acetate. Compounds specified are 5-benzenesulphonamido-1-naphthol, 5-(m-nitrobenzenesulphonamido) - 1 - naphthol, 5- (1:2:3:4- tetrahydronaphthalene - 6 - sulphonamido)-1-naphthol, 5-(p-phenoxyphenylsulphon)-amido-1-naphthol, 5-(4<SP>1</SP>:7<SP>1</SP>-diamylnaphthalene - 1<SP>1</SP> - sulphon) - amido - 1 - naphthol, 5 - (quinoline - 8<SP>1</SP> - sulphonamido) - 1 - naphthol, and 5 - (p<SP>1</SP> - amylphenoxy - p<SP>1</SP> - phenylsulphon)- amido - 1 - naphthol. N-(# - hydroxyethyl) - 5- p - toluenesulphonamido - 1 - naphthol is prepared similarly from 5-#-hydroxyethylamino- 1-naphthol, which is obtained by the reaction of ethylene chlorhydrin on 5-amino-1-naphthol. 5 - Aralkylsulphonamido - 1 - naphthols are prepared by the condensation of 5-amino-1- naphthol with an aldehyde to give an anil and reducing the anil with magnesium in methanol or with hydrogen catalytically using a Raney nickel catalyst. Compounds specified are 5 - (N - benzyl - N - p - sec. - amylbenzenesulphon - amido - 1 - naphthol, 5 - (N - benzyl- N - p - tert. - amylbenzenesulphon) - amido - 1- naphthol, 5 - (N - benzyl - N - naphthalene - α - sulphon) - amido - 1 - naphthol, 5 - (N - benzyl- N - naphthalene - # - sulphon) - amido - 1 - naphthol, and 5-[N-( α-phenyl-n-propyl):N-naphthalene-#-sulphon-amido]-1-naphthol. 5-Alkyl, aryl, or aralkyl-sulphonamido-1- naphthols in acetic acid or ethyl ether solution may be chlorinated by sulphuryl chloride or brominated by bromine. Compounds specified are 2:4 - dichloro - 5 - benzenesulphonamido -1- naphthol, 2:4 - dichloro - 5 - (p - toluenesulphonamido) - 1 - naphthol, 2:4 - dichloro - 5- (N - benzyl:N - naphthalene - α - sulphon) - amido - 1 - naphthol, 2:4 - dichloro - 5 - (N- benzyl:N - naphthalene - # - sulphon) - amido - 1- naphthol, 2:4 - dibromo - 5 - (N - benzyl:N- naphthalene - # - sulphon) - amido - 1- naphthol, and the monochloro derivatives of 5-(N- benzyl:N - naphthalene - # - sulphon) - amido - 1- naphthol and 5-[N-(γ-phenyl-n-propyl):N- (naphthalene - # - sulphon) - amido] - 1 - naphthol. p-Benzene sulphon amido-cyan- (and acyl)- acetanilides are prepared by the reaction of a monoacetyl-p-phenylenediamine with an alkyl- or aryl-sulphonic acid chloride, hydrolysis of the acetyl group, and reaction with an acylacetic or cyanacetic ester. Compounds referred to are p - (p<SP>1</SP> - toluenesulphon) - amidocyanoacetanilide, 4 - benzenesulphonamido - w - benzoylacetanilide, 4 - (p - toluenesulphonamide) - wbenzoylacetanilide, - 4 - (p -laurylbenzenesulphonamido) - w - benzoylacetanilide, and p - benzoylacetamido - N - (p - - toluenesulphonyl) N-methylanilide. A (p-toluenesulphonamido) - 2-naphthoylacetonitrile is prepared by the mono-nitration of #-acetylnaphthalene, reduction by hydrogen and Raney nickel catalyst, condensation with toluene-p-sulphonic acid chloride, reaction with bromine to give the wbromacetyl derivative, and reaction with sodium cyanide. Specification 465,823 also is referred to.