Patent GB-1181287-A (GB)
Title: Developer for Electrophotography
IPC: G03G9/09
Filed: 1967-06-06
Abstract: 1,181,287. Coloured addition polymers. CANON CAMERA CO. Inc., DAINICHISEIKA KOGYO K.K., and E. INOUE. 6 June, 1967 [6 June, 1966], No. 26167/67. Heading C3P. [Also in Division G2] Coloured polymers comprising a polymer chain having a coloured molecule chemically bonded thereto are made by copolymerizing an ethylenically unsaturated monomer or monomers either (i) together with a diazonium salt of a dye or dye intermediate or (ii) with a dye or dye intermediate containing ethylenically unsaturated groups. When a dye intermediate is used, the polymer is then treated to form the dye. The monomers preferably contain radicals which can carry a positive or negative electric charge, e.g. carboxyl, phenolic hydroxyl, sulphate ester, amino and quaternary ammonium radicals. A list of monomers and dyes is given. In examples the following dye or dye interrnediate diazonium salts and monomers are polymerized:-(1), diazotized triamino copper phthalocyanine with ethyl methacrylate, butyl acrylate, 2-dimethylaminoethyl methacrylate in the presence of polyethyleneglycol nonyl phenyl ether; (2) the zinc chloride salt of diazotized diamino copper phthalocyanine with butyl methacrylate and 2-diethylaminoethyl methacrylate in the presence of polyethylene glycol nonyl phenyl ether; (7) diazotized triamino copper phthalocyanine and acrylamide, methyl acrylate and acrylic acid;. (8) copper phthalocyanine tetra-(diazonium chloride) and methyl methacrylate, acrylamide and 2-dimethylaminoethyl methacrylate; (9) tetrachloro copper phthalocyanine tetra(diazonium chloride) and acrylamide and itaconic acid; diazotized 2: 4: 6- tris - [4 - (p - aminobenzoylamino) - 1 - anthraquinonylamino] - s - triazine stabilized with triethanolamine dodecylbenzene sulphonate and (3) polyvinyl alcohol and ethyl acrylate in the presence of dodecyl mercaptan, (5) ethyl methacrylate, octyl acrylate, 2-dimethylaminoethyl methacrylate, polyvinyl alcohol and dodecyl mercaptan, and (6) ethyl methacrylate, dibutyl itaconate, dimethylaminoethyl methacrylate, dodecyl mercaptan and FeSO 4 ; (4) diazotized diamino - perylene - tetracarboxylic acid bis - (3: 5-dimethylphenylimide) and butyl methacrylate, ethyl acrylate, acrylonitrile, glycidyl methacrylate, acrylic acid and polyethylene glycol nonyl phenyl ether; (10), diazotized 3- hydroxy-2-naphthoic acid 3<SP>1</SP>-amino-anilide and acrylamide, 2 - dimethylaminoethyl methacrylate, 2 - vinyl - 5 - methylpyridine and TiCl 3 , the polymer then being reacted with diazotized 3 - amino - 4 - methoxybenzanilide to form the dye; (11) 3-hydroxy-2-naphthoic acid (3<SP>1</SP>- methacrylamido) anilide with acrylamide, 2-dimethylaminoethyl methacrylate, methyl acrylate and potassium persulphate, the polymer then being reacted with diazotized o-anisidino-5- sulphodiethylamide to form the dye; and (12) 1 - phenyl - 3 - methyl - 4 - (4<SP>1</SP>- methacrylamido - dichlorophenylazo) - pyrazol - 5 - one with acrylamide, 2-dimethylaminoethyl methacrylate, azobisisobutyronitrile and ethylene glycol monoethyl ether. In further examples, fluorescent polymers are made by polymerizing (2) diazotized diamino- 1,2-bis-(5-methylbenzoxazole) ethene with butyl methacrylate, 2 - diethylaminoethyl methacrylate, polyethylene glycol nonyl phenyl ether and TiCl 3 ; and (13) 2-(methacrylamido-anilido)- 4 - (2: 5 - dichlorobenzoylamino) - 1: 9 - pyrimidoanthrone with dodecyl methacrylate, propylene glycol monomethacrylate, styrene, crotonic acid, azobisisobutyronitrile and ethylene glycol monoethyl ether.