Patent GB-653337-A (GB)
Title: Improvements in or relating to plasticized resin compositions
IPC: C08K5/372
Filed: 1948-04-06
Abstract: A plasticized resin composition comprises a thermoplastic polymer of a monomeric material comprising a vinyl halide, and, as a plasticizer therefor, one or more esters of sulphur-containing polycarboxylic acids, said esters containing from 14 to 36 carbon atoms, from 4 to 8 oxygen atoms connected only to carbon, and from 2 to 4 sulphur atoms, the remaining atoms being hydrogen atoms connected only to carbon, and said ester being characterized by possessing from 2 to 4 carbalkoxyalkylenethio radicals of the structure <FORM:0653337/IV (a)/1> wherein R is alkylene and R1 is alkyl.  Preferred esters among a considerable number referred to in the Specification include dioctyl dithiopropionate, dioctyl-4,7-dithiadecanedioate and dibutyl-4,10-dithia-7-oxa-tridecanedioate.  The composition preferably contains from 20 to 80 parts by weight of plasticizer to 100 parts by weight of resin.  The polymer may be polyvinyl chloride, polyvinyl bromide or a copolymer of vinyl chloride or vinyl bromide with one or more of vinyl acetate, vinylidene chloride, vinylidene bromide, styrene, acrylonitrile, methyl acrylate, ethyl acrylate, methyl chloroacrylate, ethyl cyanoacrylate, methyl methacrylate, diethyl fumarate, diethyl chloromaleate, isobutyl crotonate, vinyl isobutyl ether, vinyl methyl ketone, vinyl benzoate, vinyl butyrate, vinyl furane, vinyl pyridine, dichlorostyrene, isobutylene and ethylene.  The Specification as open to inspection under Sect. 91 refers also to compositions containing polymers and copolymers of vinyl acetate, vinyl benzoate, methyl acrylate, ethyl acrylate, vinylidene chloride, vinyl ethers, vinyl ketones, styrene and acrylonitrile, and to compositions containing polyethylene, polyvinyl alcohol, and polyvinyl acetals.  This subject-matter does not appear in the Specification as accepted.ALSO:The Specification refers to the preparation of esters containin from 2 to 4 radicals of the structure <FORM:0653337/IV (b)/1> where R is alkylene and R1 is alkyl, and of theacids from which they are derived.  A compound of the formula <FORM:0653337/IV (b)/2> is prepared by esterifying the oxidation product of omega-mercaptoundecylic acid.  Compounds of the formula <FORM:0653337/IV (b)/3> may be made by reacting a dihaloalkane with two moles of a mercapto substituted aliphatic carboxylic acid in the presence of an alkali and then esterifying the resulting acid, e.g. dioctyl 4,7-dithia-decane dioates may be made by reacting two moles. of beta-mercaptopropionic acid with 1,2-dichloroethane in the presence of alkali and then heating the resulting acid with an octyl alcohol in the presence of an esterification catalyst.  Compounds of the general formula <FORM:0653337/IV (b)/4> where A may contain any or all of carbon, hydrogen, oxygen and sulphur, and x is an integer from 2 to 4, may be prepared by esterifying the acids obtained by reacting a compound of the formula A(Cl)x such as the various aliphatic dichloroethers, dichlorothioethers, dichloroketones and dichlorocarboxylic acids, with a mercapto-substituted carboxylic acid such as p  mercapto-acetic acid, mercaptopropionic acids and mercapto-butyric acids, e.g. dialkyl 4,8-dithia-5-oxo-undecanedioates are prepared by esterifying the acid prepared from dichloroacetone and beta-mercaptopro-pionic acid.  Phosgene or thiophosgene may be reacted with mercapto-carboxylic acids and the resulting acids esterified to give esters such as dioctyl 4,6-dithio-5-oxo-nonanedioate.