GB676376A - New polymerisable compounds and polymers thereof - Google Patents

Abstract

Polymers and copolymers are prepared by polymerizing p-vinyl benzamide alone or in admixture with other monomers, e.g. styrene. The preparation of the p-vinyl benzamide is described (see Group IV (b)). Cross-linking of the polymer may be effected by elimination of ammonia between amido groups on adjacent chains. Conversion into insoluble products may also be effected by reacting the polymer with formaldehyde or substances yielding it, e.g. by heating a mixture of the powdered polymer and paraformaldehyde, or by soaking foils, films or fibres in aqueous formaldehyde followed by baking. Alternatively the formaldehyde treatment may be effected simultaneously with the polymerization, or preformed reaction products of p-vinylbenzamide and formaldehyde, such as N-methylol-p-vinyl benzamide may be polymerized alone or with other monomers and cross-linked by heating. In examples there are described the polymerization of p-vinylbenzamide; (3) by heating in a sealed tube; (4) in toluene solution; (5) and (6) in admixture with styrene, by heating in a sealed tube in solution with isopropylbenzene and benzoyl peroxide catalysts; (7) as an aqueous emulsion together with styrene, sodium stearate and ammonium sulphate. Examples (8), (9) and (10) describe the hardening of the solid products of (5), (6) and (7) by soaking in formaldehyde solution followed by baking. In example (11) there is polymerized an emulsion of p-vinyl-benzamide, styrene, aqueous sodium stearate, ammonium persulphate and formaldehyde. In (12) a formaldehyde/p-vinyl-benzamide condensation product (N-methylol p-vinylbenzamide mainly) is emulsion copolymerized with styrene. In example (13) a styrene-p-vinylbenzamide copolymer is rendered insoluble by hot-milling with paraformaldehyde. The polymers, previously soluble in, e.g. benzene, cresol, dimethylformamide, are rendered insoluble. Other hardening agents mentioned are dimethylolurea, hexamethylol-melamine, phenol-aldehyde condensation products and hexamethoxymethyl-melamine. In place of styrene as comonomer are mentioned diene hydrocarbons, ethyl acrylate, methacrylic esters, maleic anhydride, drying oils, e.g. linseed and tung oils and their fatty acids, oil-modified alkyd resins and polymerizable unsaturated alkyd resins.ALSO:The Specification comprises p-vinyl benzamide. Examples describe its preparation by (1) the hydrolysis of p-cyanostyrene with aqueous sodium hydroxide and hydrogen peroxide; (2) the reaction of thionyl chloride with p-vinyl benzoic acid to form p-vinyl benzoyl chloride and th2 reaction of the latter with dry ammonia. N-methylol p-vinyl benzamide is made (12) by reacting the p-vinyl benzamide with formaldehyde. The amide and the methylol amide are used to prepare synthetic resins (see Group IV (a)).