Quaternary salts of resinous c-vinylpyridine polymers and photographic films rendered antistatic therewith

摘要

A resinous C-vinylpyridine polymer is reacted with a compound of formula: so that a quaternary salt of the polymer is obtained wherein at p least 70% by weight of the vinylpyridine units are linearly recurring units of the formula: the remainder of the vinyl pyridine units being linearly recurring units of the formula: wherein Y is a hydrogen atom or an alkyl group of 1 to 4 carbon atoms, X is a halogen atom, and A is an alkyl group of 1 to 4 carbon atoms, a phenyl group, an alkylphenyl group in which the alkyl group contains 1 to 4 carbon atoms, a hydroxyphenyl group, a dihydroxyphenyl group, a halogenophenyl group, an aminophenyl group, an acetamidophenyl group, an alkoxyl group in which the alkyl radical contains 1 to 24 carbon atoms, a vinyloxyl group, an amino group, an alkylamino group in which the alkyl radical contains 1 to 4 carbon atoms, an anilino group, a dialkylamino group in which both alkyl radicals contain 1 to 4 carbon atoms, or an N-phenyl-N-alkylamino group in which the alkyl radical contains 1-4 carbon atoms. Lists of compounds of formula are given. The polymer may be a copolymer of a C-vinyl-pyridine with styrene, methyl acrylate or methacrylate, acrylamide, N-methyl acrylamide or methacrylamide, or N, N-dimethyl acrylamide. In examples poly-4-vinylpyridine is reacted with chloroacetone to obtain poly-1-acetonyl-4-vinyl pyridinium chloride, with p-chloroacetylacetanilide to obtain poly-4-vinylpyridinium-p-chloroacetyl-acetanilide, with chloroacetopyrocatechol to obtain poly-4-vinylpyridinium chloroacetopyrocatechol, with ethyl chloroacetate to obtain poly-4-vinyl-pyridinium ethylchloroacetate, with n-butyl chloroacetate to obtain poly-4-vinylpyridinium n-butyl chloroacetate, with ethyl bromoacetate to obtain poly-4-vinylpyridinium ethyl bromoacetate, with n-octadecyl chloroacetate to obtain poly-1-octadecyl-4-vinyl-pyridinium chloroacetate, with chloroacetamide to obtain poly-4-vinylpyridinium chloroacetamide, with a -chloro-N, N-diethylacetamide to obtain poly-4-vinylpyridinium-a -chloro-N N-diethylacetamide, with a -chloro-N-ethyl acetanilide to obtain poly-4-vinylpyridinium-a -chloro-N-ethyl acetanilide, and with vinyl-chloroacetate to obtain poly-4-vinyl-pyridinium vinyl chloroacetate; and poly-2-methyl-5 vinylpyridine is reacted with ethyl bromoacetate to obtain poly-2-methyl-5-vinyl-pyridinium ethyl bromoacetate. The quaternized polymers may be used as antistatic coatings on photographic films.