Patent GB-542904-A (GB)
Title: Improvements in or relating to colour-formers for use in colour photography
IPC: G03C7/36
Filed: 1940-02-12
Abstract: 542,904. Dye intermediates. DU PONT FILM MANUFACTURING CORPORATION. Feb. 12, 1940, No. 2705. Convention date, Feb. 13, 1939. [Class 2 (iii)] [Also in Group XX] Colour couplers of the general formula wherein R and R<SP>1</SP> each represent hydrogen, halogen, a substituted or unsubstituted hydrocarbon radical, or a heterocyclic radical, R 1  and R 2  each represent a substituted or unsubstituted hydrocarbon radical or a heterocyclic radical, and Y represents an amino group substituted by a substituted or unsubstituted aryl radical, by an aralkyl radical, or by a heterocyclic radical, or represents a group OR  3 , wherein R 3  has. the same significance as R 1  and R  2  are prepared by re-acting acylacetic compounds with an aldehyde or ketone such as formaldehyde, acetaldehyde, propionaldehyde, acrolein, glyoxal, benzaldehyde, salicylaldehyde, p-hydroxybenzaldehyde, furfural, acetone, or acetophenone, or with compounds containing reactive halogen atoms, such as chloroform. Acidic or basic condensing agents, such as hydrochloric acid, sulphuric acid, p-toluenesulphonic acid, sodium hydroxide, ammonium hydroxide, or potassium hydroxide, or readily hydrolysed salts, such as sodium acetate or ammonium chloride, may be used. The radicals Y and also the radicals R 1  and R 2  may be identical and the radicals R and R<SP>1</SP> may both be hydrogen atoms. R and R<SP>1</SP> may be methyl, .ethyl, phenyl, naphthyl, chlor-phenyl, hydroxyphenyl, carboxyphenyl, or sulphoxyphenyl R 1  and R 2  may be methyl, ethyl, propyl, isopropyl, cyclohexyl, abietyl, tetra-hydroabietyl, menthanyl, phenyl, naphthyl, benzyl, furyl, or thienyl, which groups may be substituted by other groups such as nitro. or amino. Y may be p-aminophenylmorpholine, p-anisidine, p-phenetidine, p-chloraniline, α-naphthylamine, #-naphthylamine, p-aminophenylpiperidine, p-aminodimethylaniline. benzoyl-p-phenylenediamine, N-ethyl : N- benzyl-p-phenylenediamine, N-ethyl N- phenyl - p - phenylenediamine, 2 : 5 - dimethylaniline, 4 - chloro - 2 : 5 - dimethylaniline, 2 : 3 : 5 : 6 - tetramethylaniline, 2 - chloro - 5 - methylaniline, m - toluidine, 3 - bromo - 4 - methylaniline, 3 - nitro - 4 - methylaniline, 2 : 5 - diethoxy - 4 - chloraniline, 2 : 5 - dimethoxy - 4 - chloraniline, 2 : 5 - diethoxy - 4 - propylaminoaniline, 3 - benzoylamino - 4 - methoxyaniline, 4 - benzoylaniino - 3 - methoxyaniline, 5 - bromo - 2 - methoxyaniline, o - phenoxyaniline, 2 : 5 - diethoxy - 4 - nitraniline, m-nitraniline, p-phenoxyaniline, p-nitraniline, o-chloraniline, p-aminophenylbenzyl ether, 4- chloro - 2 - methoxy - 5 - isopropylaniline, p-fluoraniline, 2-nitro-4 : 6-dimethylaniline, paminobenzoyl-2-amino benzthiazole, 2-amino-6- methylbenzthiazole, 2-methoxy-4-nitraniline, p-amino-p<SP>1</SP>-hydroxyazobenzene and benzylamine. Examples specified are methylene-bisp-nitrobenzoylacetic ethyl ester, methylenebis-furoylacetic ester, methylene-bis-acetoacetanilide, methylene - bis - benzoylacetanilide, methylene - bis - furoylacetanilide, methylene - bis - benzoylacet - 2 - amino - 6 - methylbenzthiazole, methylene-bis-benzoylacetic ester, and ethylidene-bis-acetoacetic ester.