Patent GB-1016952-A (GB)
Title: Plasticised halogen-containing resins
IPC: C08K5/11
Filed: 1962-07-23
Abstract: A plastic composition comprises in uniform admixture a polymer of which at least 50% by weight is formed from a halogen-containing monomer having a terminal ethylenically unsaturated group and, as plasticizer therefor, a polymerizable fumaric acid ester composition, the said plastic composition further containing a polyallyl ester of a polybasic acid. The fumaric acid ester compositions may have the general formula <FORM:1016952/C3/1> where A is the fumaryl radical <FORM:1016952/C3/2> R is a divalent aliphatic or alicylic hydrocarbon or oxyhydrocarbon radical; R1 and R2 are each alkyl, cycloalkyl, alkenyl or aralkyl n is 0, 1 or 2; m and y are unlike and each is 0 or 1 and the sum of m+n is at least 1.  They may be prepared as in Specification 997,172. The polyalkyl esters are esters of any allyl alcohol, substituted or unsubstituted, with a polybasic acid which is saturated or unsaturated. A substantially non-volatile alkyl substituted monoaryl compound may be added to improve the viscosity (hereinafter called an aryl alkane). Preferred aryl alkanes are obtained by (1) condensing an aromatic hydrocarbon of the benzene series with an acylic propylene polymer containing 12 to 18 carbon atoms and (2) mono-alkylating benzene with the product obtained by substantial mono-chlorination of paraffin base kerosene fractions. Peroxy compounds, fillers, stabilizers and colouring materials may be added.  In the examples the halogen containing polymer is polyvinyl chloride and the polyallyl esters employed are diallyl adipate, diallyl phthalate, diallyl succinate, diallyl sebacate, diallyl oxalate, diallyl malonate, diallyl dimerate, diallyl diglycollate and triallyl citrate.ALSO:Fumaric acid esters of the general formula <FORM:1016952/C2/1> where A is the fumaryl radical <FORM:1016952/C2/2> R is a divalent aliphatic or alicyclic hydrocarbon or oxyhydrocarbon radical; R1 and R2 are each alkyl, cycloalkyl, alkenyl or aralkyl; n is 0, 1 or 2; m and y are unlike and are each 0 or 1 and the sum of m and n is at least 1 may be prepared by one of the following methods:-  (1) Reacting a partial ester of maleic acid <FORM:1016952/C2/3> where X is an aliphatic or alicyclic hydrocarbon radical of valency X and X is a whole number from 2 to 6, with at least one hydroxy compound R1OH where R1 is alkyl, cycloalkyl, alkenyl or aralkyl, in the presence of a halogen-containing compound; (2) Reacting a fumaryl chloride of formula <FORM:1016952/C2/4> where R1 is above, with a polyhydroxy compound having 2 to 6 hydroxyl groups, the molar ratio of chloride to polyhydroxy compound being X:1 where X equals the number of hydroxyl groups; and (3)  Reacting a fumarate ester of formula <FORM:1016952/C2/5> where R1 is as above, with a polyhydroxy compound having 2 to 6 hydroxyl groups, the molar ratio of the fumarate ester to polyhydroxy compound being 1 to 1.5 X: 1 where X is the number of hydroxyl groups.  In the examples fumaric acid esters are formed by (1) reacting isobutyl fumaryl chloride with 1,3-butanediol and (2) reacting the following dialkyl fumarates with the following polyhydroxy compounds :- diisohexyl, dibutyl, dimethylamyl, diiso-octyl, diisohexyl, di-2-ethylhexyl or diisobutyl fumarates and 1,2-, 1,3- or 1,4-butanediol; neopentyl glycol; dipropylene glycol and di- or triethylene glycol.