Improvements in or relating to colour couplers and to their production and use in colour photography

摘要

The invention comprises compounds of the general formula: wherein A is a trivalent radical derived from 1,2-phenylene, 2,3-naphthylene or di- or trimethylene, B is a colour coupler residue, Y is -CO-, -CONH-, -COCH2- or -COCH2S- and R is a hydrocarbon group which may be substituted. The residue B is such that BNH2 will react with the oxidation products of N,N-diethyl-p-phenylenediamine, formed during the development of a silver salt image with that compound, to yield a quinoneimine or azamethine dyestuff. Such compounds are prepared by reacting with BNH2 a compound of formula Z-A(CO)2N-R wherein Z is -COX, -CH2COX, -NCO, -NHCOOC6H5 or -SCH2COX and X is halogen. In examples, R is a 4, 6, 8, 10, 12, 14, 16 or 18C alkyl group, or 4-dodecylphenyl, benzyl or cyclohexyl and B is 5-keto-1-phenylpyrazol-3-yl, 4 - (4 - methoxybenzoylacetamido) - 3 - methoxyphenyl, b -(1-hydroxy-2-naphthamido) ethyl, 4-cyanoacetylphenyl or 4-(3, 5-dimethoxycarbonylphenyl) carbamylacetylphenyl. Starting materials. (1) Trimellitic anhydride reacted with octadecylamine to give 4-carboxy-N-octadecylphthalimide which gave the 4-chlorocarbonyl compound with thionyl chloride. Other N-alkyl-4-chlorocarbonyl-phthalimides were similarly obtained. (2) Octadecylamine reacted with 4-nitrophthalic anhydride to give 4-nitro-N-octadecylphthalimide which was reduced with Raney Ni to the 4-amino compound; reaction of the latter with phosgene gave 4-isocyanato-N-octadecylphthalimide. (3) Tricarballylic anhydride (from the acid and acetyl chloride) reacted with 4-dodecylaniline giving N(4-dodecylphenyl) succinimidoacetic acid from which the acid chloride was obtained using thionyl chloride; N-octadecylsuccinimidoacetic acid was similarly obtained. (4) Carboxymethylmercaptosuccinic acid reacted with 4-dodecylaniline giving N(4-dodecylphenyl) succinimidomercaptoacetic acid which afforded the acid chloride with thionyl chloride. The compounds are used as colour couplers (see Division G2) either directly or in dilute alkali, in which case the imide ring is opened. Specific alkaline hydrolysis products isolated-(Examples 26 and 27) are 41-methoxybenzoylacet-2-methoxy-5 (3- or 4-cyclohexylaminocarbonyl-4-or 3-carboxybenzoylamino) anilide and its analogue in which benzyl replaces cyclohexyl.