GB618175A - The production of polyvinyl amine compounds - Google Patents

Abstract

A salt of a basic polyvinylamine compound is prepared by reacting a polyvinyl cyclic imide with hydrazine hydrate, treating the resinous product with an acid and separating the formed salt from impurities by dissolving in water and precipitating in a water-miscible liquid which is a non-solvent for the salt. Alternatively, the resinous product may be treated with an acylating agent and the formed acylamide hydrolysed to a salt of polyvinylamine. The polyvinyl cyclic imides preferably contain 5 or 6 atoms in the ring and have the general formula <FORM:0618175/IV(a)/1> where R represents a divalent organic radical, e.g. an ethylene group, a 1,2-propylene or a 1,2-phenylene group, or these groups substituted by one or more alkyl, alkoxy, phenyl, carbethoxy or halogen groups. Polyvinyl phthalimide, succinimide and glutarimide are specified. On refluxing with hydrazine hydrate, a polymeric substituted cyclic hydrazide of, for example, phthalic acid, is formed which, when treated with, for example, halogen acids, acetic, alpha-chlorpropionic or brombenzoic acids, form the corresponding salt of polyvinylamine. Suitable non-solvents for the salts are methanol, ethanol and acetone. In the acylamide process, the isolated and dried polymeric substituted cyclic hydrazide is treated with acyl anhydrides such as acetic, propionic, butyric, phenoxyacetic or benzoic anhydrides, and the acylamide hydrolysed with, for example, hydrochloric acid, to the amine salt. The free base polyvinylamine may be obtained in the usual ways but preferably in the absence of carbon dioxide. In addition, examples describe the polymerization of N-vinyl phthalimide by refluxing a solution of it in ethylene dichloride and methanol containing benzoyl peroxide and precipitating in ethanol. 5: Polyvinylbenzamide is prepared by mixing polyvinylamine hydrobromide with benzoyl chloride and caustic soda, the product being soluble in methanol, ethanol and in acetone-water and dioxane-water mixtures. 6B: Polyvinyl phthalimide is refluxed with hydrazine hydrate and water-producing polyvinylamine and the hydrazine salt of phthalhydrazide. The latter is removed by precipitation in methanol and by forming the barium salt. Carbon dioxide is passed in to remove the barium and forms a polyvinylamine salt of carbonic acid which with concentrated hydrobromic acid gives polyvinylamine hydrobromide. Polyvinylamine may be used in photographic emulsions, alone or together with polyvinyl alcohol or cellulose compounds. The polyvinyl acylamides may be used as fibres and in film base.ALSO:Vinyl cyclic imides, the polymers of which may be reacted with hydrazine hydrate in the formation of basic salts of polyvinylamine compounds (see Group IV (a)), are prepared by pyrolysis of the N-(beta-acyloxyethyl) derivatives of cyclic imides: e.g. vinyl phthalimide from N-(beta-acetoxyethyl) phthalimide.