Patent GB-964871-A (GB)
Title: Improvements in or relating to electrophotography
Inventor: CASSIERS PAUL MARIA
IPC: C08F8/00
Filed: 1959-02-26
Abstract: p-Acrylylamino-stilbene is made by treating p-aminostilbene with acrylyl chloride in diethylamine.  2- (p-acrylyloxyphenyl) -4- (p-dimethylaminophenyl)-5-phenyl -imidazole,2-(p-methacrylyloxyphenyl) -4- (p-dimethylaminophenyl) -5- phenylimidazole and 1-(b -methacrylyloxyethyl) -2:4:5-triphenyl-imidazole are obtained by reacting the corresponding hydroxy compounds with acrylic or methacrylic anhydride or chloride in benzene.ALSO:A polymeric photoconductive composition contains a photoconductive polymeric material as below, with or without a sensitiser (see below), a plasticizer (phthalates and phosphates specified), a pigment and/or an agent controlling viscosity, free flow ageing thermal stability, oxidation or gloss. The photoconductive polymeric material may in general be a vinyl polymer or copolymer, a polyester or a cellulose derivative. Many suitable vinyl polymers are mentioned, these being polyvinyl acetals; polymers containing an unsaturated side chain such as polyvinyl cinnamate, polyvinyl-ureido-stilbenes, polyacrylyloxy-stilbenes and polyacrylylamido-stilbenes; polymers containing a heterocyclic ring in a side chain attached directly or via an amide, urea, azomethine or ester group, such as a pyridine, quinoline, pyrrole, furan, imidazole, thiazole, pyrazoline, coumarone, benzoxazole, benzthiazole, carbazole or phenthiazine ring; and polymers containing in the side chain a diarylmethane group or a polycyclic aromatic nucleus such as fluorene or anthraquinone.  Copolymers may include one of the above or may be di- or terpolymers of simpler units. It is stated that the above polymers may be made by normal methods in solution or emulsion, initiated by free radicals, ion-formation or radiation. Among the many polymers listed the preparation of the following is given in detail: copolymers of ethyl acrylate and p-(N-acrylylamino)-stilbene; polymers of 2-(p-acrylyloxyphenyl) -4- (p-dimethylaminophenyl) -5- phenyl-imidazole, 2-(p-methacrylyloxyphenyl) -4- (p-dimethylaminophenyl) -5- phenyl-imidazole and 1-(b -methacrylyloxyethyl)-2:4:5-triphenyl-imidazole; copolymer of styrene and 2-(o-vinylureido-phenyl)-4:5-diphenyl imidazole, from 2-(o-aminophenyl)-4:5-diphenyl-imidazole and the copolymer of styrene and vinyl isocyanate; reaction product of polyacrolein and 1-amino-anthraquinone. The polyesters may be those described in Specifications 883,312, 891,781, 901,605 and 916,660.  The cellulose derivative may be the acetate -N- phenyl-carbamate or the acetate-cinnamate. Specified sensitisers are iodoform, 1-chloro-anthraquinone, various diazonium salts and diazo-sulphones, fluoresceins, triphenylmethane dyes, xanthene dyes, methine dyes, azomethines, ketones as in Specifications 681,132 and 686,733, coumarins, imidazoles and benzthiazoles and the compounds mentioned for this purpose in Specification 964,873. The various ingredients of the composition are dissolved or dispersed in an organic solvent such as benzene, xylene, ethanol, acetone, methylene chloride, tetrachlorethane, dioxan, dimethylformamide or glycol monomethyl ether, spread on a support and dried. Instead of using the polymers as such, suitable monomers or mixtures of monomers and polymers can be applied to the support and polymerized, condensed or cross-linked in situ. Specified polymers in the examples are polyvinyl formal, acetate and cinnamate, polyester of diphenyl-4:41-di-sulphonic acid and 2:2-bis-(p-hydroxyphenyl)-propane, poly -2- (acrylyloxynaphthyl) -4- phenyl -5- (p-dimethylaminophenyl - imidazole, poly-1: 3-diphenyl -5- (p-acrylyloxyphenyl)-pyrazoline, copolymer of vinylidene chloride and acrylonitrile, and polymer of 4:41-dihydroxy-2:21-diphenylpropane and trans-cinnamic acid-p-oxyacetic acid.  Monomeric photoconductors may also be present in the compositions, e.g. the compounds mentioned in Specifications 964,873 and 964,874, but at least 90% of the photoconductive material must be polymeric.  Polyvinylcarbazole is disclaimed as it is covered by Specification 856,770.  Specification 964,871 refers also to the use of polyvinyl acetate, polymethacrylic ester of methyldiethylethanolammonium hydroxide, polymethyl methacrylate, copolymer of acrylonitrile with styrene copolymer of nitrostyrene and diethyl maleate, copolymer of styrene and butadiene, polyester of 2:2-di-(p-hydroxy-phenyl)-propane with fumaric acid, polyester of isophthalic acid with di-(p-hydroxyphenyl)-methyl-isobutyl-methane, and amylose acetate.