Patent GB-666604-A (GB)
Title: Improvements in interpolymers
IPC: C08F2/00
Filed: 1949-06-10
Abstract: Interpolymers of (1) a 2-propenyl polyester, (2) a compound of the formula RR1C=CR11, R111 where R is selected from hydrogen, fluorine, and methyl, R1 from hydrogen, fluorine, carboxyl and radicals hydrolysable to carboxyl, R11 from hydrogen, lower alkyl, chlorine, fluorine, carboxyl and radicals hydrolysable to carboxyl, R111 from hydrogen, lower alkyl, chlorine, fluorine, carboxyl and radicals hydrolysable to carboxyl, alkoxy, aryloxy, aralkoxy, acyloxy, acyl and additionally R111 may represent a radical selected from carboxyl and radicals hydrolysable to carboxyl when R11 is selected from carboxyl or radicals hydrolysable to carboxyl and R111 may with R11 comprise a radical selected from the groups -CO-O-CO-and-CO-NR#f-CO-where R#f is selected from hydrogen, alkyl, aryl, and aralkyl, and (3) a compound selected from 2-propenyl alcohols, 2-propenyl chlorides, 2-propenyl alcohol mono-ethers of non-ethylenic alcohols and 2-propenyl alcohol mono-esters of non-ethylenic carboxylic acids are made by heating, optionally in the presence of a polymerization catalyst, (1) at 25 DEG  to 120 DEG  C. with from 0.1 to 8.0 molar equivalents of (2) and from 0.2 to 15.0 molar equivalents of (3) and stopping the reaction before the mixture gels.  Specified polyesters are diallyl fumarate, diallyl maleate, dimethallyl itaconate, di-2-chloroallyl itaconate, diallyl mesaconate, dimethallyl citraconate, triallyl aconitate, diallyl oxalate, diallyl malonate, diallyl alphamethyl malonate, diallyl succinate, dimethallyl glutarate, di-2-chlorallyl adipate, diallyl sebacate, diallyl azelaate, dimethallyl suberate, dimethallyl and diallyl phthalate, triallyl carballylate, diallyl carbonate, dimethallyl sulphate, triallyl phosphate, tetraallyl silicate, tetramethallyl stannate and tetraallyl titanate. Compounds mentioned of (2) are methyl, butyl, octyl, beta-chloroethyl, benzyl, and phenyl acrylates, methyl and butyl methacrylates, diethyl, bis-(beta-chloroethyl), dibutyl, dibenzyl, benzyl ethyl, and bis-(2-ethylhexyl) fumarates, dimethyl, diethyl, dihexyl, di-cyclohexyl, bis-(beta-phenylethyl), dioctyl, and bis-(beta-chloroethyl itaconates and the corresponding esters of mesaconic, citraconic, and aconitic acids, vinyl acetate, chloroacetate, butyrate, benzoate, phenyl-acetate and trichloroacetate, isobutylene, vinyl chloride, vinylidene chloride, acrylamide, N-methylacrylamide, acrylonitrile, methacrylonitrile, fumaronitrile, maleimide, N-butylmaleimide, vinyl n-butyl ether, vinyl hexyl ether, vinyl phenyl ether, and vinyl benzyl ether.  The 2-propenyl (3) compound may be allyl chloride, methallyl chloride, crotyl chloride, 2,3 - dichloropropene, 1,4 - dichlorobutene-2, 2-(chloromethyl) allyl chloride, allyl, methallyl, 2-chloroallyl, crotyl, cinnamyl, and 2-ethyl-allyl alcohols, allyl methyl, methallyl ethyl, allyl propyl, methallyl butyl, methallyl amyl, methallyl heptyl, allyl octyl, crotyl ethyl, 2-chloroallyl ethyl, methallyl phenyl and allyl benzyl ethers, beta-allyloxyethanol, allyl acetate, 2-chloroallyl propionate, methallyl butyrate, ethallyl valerate and cinnamyl acetate.  Specified catalysts are acetyl and benzoyl peroxides, cumene and t-butyl hydroperoxides.  The interpolymers alone or dissolved in a solvent which may be a copolymerizable ethylenic compound, e.g. styrene, diallyl adipate, diethyl fumarate, n-butyl acrylate, phenyl acrylate, allyl methacrylate, and vinyl benzoate may be moulded, e.g. into rods, blocks or sheets, or used as coatings, impregnants, or in laminating and the interpolymer further polymerized to the hard, solvent-insoluble stage by heat and/or pressure and/or polymerization catalysts. The interpolymers prior to the hardening treatment may be mixed with dyes, pigments, fillers and plasticizers.