Patent GB-880206-A (GB)
Title: Substituted acrylamide colour couplers
IPC: G03F7/027
Filed: 1959-10-12
Abstract: Acrylamide derivatives of the formula:-  <FORM:0880206/IV (a)/1> wherein Q is an organic radical containing an active methylene group or a hydroxy-substituted aromatic ring in which the carbon atom in the para position to the hydroxyl group is unsubstituted, and R represents hydrogen, chlorine, C1-4 alkyl, aryl or aralkyl, alone or admixed with one or more other monomers are polymerized in emulsion or organic solvent medium in the presence of initiators such as benzoyl peroxide, a , a 1-azo-bis-(isobutyronitrile), diacetyl, benzoin, pivaloin, benzoin methyl and ethyl ethers, anthraquinone, naphthoquinone, aluminium chloride and boron trifluoride. Specified comonomers are acrylic acid, acrylamide, acrylonitrile, b -aminoethyl acrylate and methacrylate, vinyl esters, styrene and ring substituted styrenes, vinylidene chloride, vinyl alkyl ethers, vinyl pyrrolidone, vinyl pyridine and vinyl sulphonic acid.  Organic or inorganic fillers such as polymethacrylic acid, polyvinyl alcohol, cellulose acetate, glass powder, sand or diatomaceous earth may also be incorporated in the polymerized composition.  The polymers may be incorporated as colour couplers into photographic silver halide emulsions and developed, after exposure, with amine developing agents to give coloured dye images.  The polymers may also be employed in photopolymerizable compositions to make relief images or shaped articles, for colouring plastic materials and in dyeing or colouring textile materials.  Specifications 562,675, 741,294, 741,441 and 875,248 are referred to.ALSO:The invention comprises compounds of the formula <FORM:0880206/IV (b)/1> wherein Q is an organic radical preferably attached to the nitrogen atom through a cyclic carbon atom of a 5- or 6- membered carbocyclic or heterocyclic nucleus and which contains an active methylene group (viz a -CH2- group which is activated by being connected on both sides directly or through a conjugated system to a carbon or nitrogen atom which is connected to <FORM:0880206/IV (b)/2> <FORM:0880206/IV (b)/3> a further atom by a double or triple bond, as in a nitro, keto, cyano or imino group or a hydroxylsubstituted aromatic ring in which the carbon atom in the para position to the hydroxyl group is unsubstituted, and R represents hydrogen, chlorine, C1-4 alkyl, aryl or aralkyl.  The above compounds are prepared by reacting an acrylyl halide or a -substituted acrylyl halide of the formula CH2=C(R)-CO. halogen with an amine of the formula Q-NH2.  The monomers obtained as final products may be further subjected to addition polymerisation, and both the monomers and polymers may be used as colour couplers.  The examples describe the preparation of 1-(meta-methacrylamidophenyl)-5-pyrazolone-3-carboxylic acid, meta-methacrylamido-a -benzoylacetanilide, 2 - chloro - 4 - methacrylamido - a  - benzoylacetanilide, 4 - acrylamido - 2 - chloro - a  - benzoylacetanilide, 5 - methacrylamide-1-naphthol <FORM:0880206/IV (b)/4> meta-Nitro-a -benzoylacetanilide and 2-chloro-4-nitrobenzoyl acetanilide are prepared by reacting ethyl benzoylacetate with meta-nitroaniline and 2-chloro-4-nitroaniline respectively.  The compounds may be reduced to the corresponding amino compounds. Specifications 562,675, 741,294, 741,441 and 875,248 are referred to.