Improvements in or relating to the manufacture of polymerizable esters

摘要

Compounds having the formula wherein n represents a whole number and R represents an allylic radical (e.g. allyl, methallyl) are obtained by esterifying o-benzoylbenzoic acid by any known method and, if necessary, subsequently, polymerizing the ester by heating alternatively the ester may be interpolymerized by treatment with one or more compounds which contain an olefinic linkage of the type R1CH=CR2R3, wherein R1 represents H, alkyl, acyl or carbalkoxy; R2 represents H, cyano, acyl, alkyl, or carbalkoxy; or, wherein R1 and R2 together represent the residue -CO-O-CO-; and R3 represents H or alkyl. Specified esterification catalysts are: p-toluenesulphonic acid and sodium ethylate. Specified interpolymerizing reagents are: vinyl acetate maleic anhydride, esters of acrylic acids, fumaric esters, acrylonitrile, methacrylonitrile, methyl isopropenyl ketone. Specified polymerization accelerators are: acetyl peroxide, benzoyl peroxide, lauroyl peroxide, succinyl peroxide, tert.-butyl hydrogen peroxide. In examples: (1) o-benzoyl-benzoic acid is heated with allyl alcohol, benzene and p-toluene sulphonic acid to form allyl o-benzoyl-benzoate; (2) to (8) allyl o-benzoyl benzoate is heated with: (2) 65 per cent aqueous tertiary-butyl hydrogen peroxide at 120 DEG C. to form a brown gum which after repeated precipitations from acetone becomes a yellow powder; (3) benzoyl peroxide at 75 DEG C. and the reaction product is poured into gasoline to obtain a soft white polymer; (4) vinyl acetate and 65 per cent aqueous butyl hydroperoxide at 120 DEG C. to form a green liquid which is purified by repeatedly dissolving it in acetone and precipitating it with ligroin to obtain a yellow powder; (5) maleic anhydride and 65 per cent aqueous tertiary-butyl hydrogen peroxide at 120 DEG C. to form a green gum which is purified by repeatedly dissolving it in acetone, precipitating it with methanol and washing it with ligroin to obtain a white powder; (6) acrylonitrile and 65 per cent aqueous tert.-butyl hydrogen peroxide at 120 DEG C. to obtain a yellow powder; (7) methyl isopropenyl ketone and benzoyl peroxide at 75 DEG C. to obtain a brown powder; (8) methyl methacrylate and tertiary butyl hydroperoxide at 120 DEG C. to obtain a white solid; (9) methyl o-benzoyl benzoate is heated with methallyl alcohol in the presence of 5 per cent sodium ethylate in ethanol and tert.-butyl catechol, to form methallyl o-benzoyl benzoate which is polymerized and copolymerized as in the previous examples. The allylic o-benzoylbenzoates may be used as plasticisers for polymethyl methacrylate and polystyrene.