Patent GB-859642-A (GB)
Title: Lactone polyesters and a process for their preparation
IPC: C08G69/44
Filed: 1957-04-15
Abstract: A polyester is made by heating at 50 DEG -300 DEG C. a lactone having at least six carbon atoms in the ring with an initiator which is an organic compound containing at least one alcoholic group or a primary or secondary amino group attached directly to carbon or with a polycarboxylic acid, a hydroxycarboxylic acid or an aminocarboxylic acid.  The lactone preferably has the formula: <FORM:0859642/IV(a)/1> where n is at least four, at least n + 2 Rs are hydrogen and the remaining Rs are hydrogen, alkyl, cycloalkyl, alkoxy or single ring aromatic hydrocarbon radicals.  A very large number of initiators are specified, including aliphatic, cycloaliphatic, aromatic and heterocyclic mono-, di- and higher poly-hydric alcohols; aliphatic, cycloaliphatic, aromatic and heterocyclic mono-, di- and higher poly-amines in which the amino groups are primary or secondary; polyols which are polyoxyalkylated derivatives of di- or higher poly-functional compounds having their functional groups in the form of primary or secondary hydroxyl, phenolic hydroxyl, primary or secondary amino, amido, hydrazino, guanido, ureido, mercapto, sulphino, sulphonamide or carboxyl groups; polymeric cyclic oxides with hydroxyend groups; oxyalkylated phosphoric acid; di; and higher poly-functional amino alcohols, carbohydrates and alkyl glycosides; aliphaticcycloaliphatic and aromatic di- and higher polycarboxylic acids; aliphatic and aromatic hydroxycarboxylic and aminocarboxylic acids; a mixture of a dicarboxylic acids with a molar excess of a glycol, a diamine or an amine alcohol; and vinyl polymers containing hydroxyl or amino groups, e.g. saponified ethylene/vinyl acetate copolymers, polyvinyl alcohol, and copolymers of ethylene with amino styrenes, 3-butene-1, 2-diol, allyl alcohol, methallyl alcohol, 3-phenyl-3-butene-1-ol and diethylene glycol monovinyl ether.  Catalysts for the reaction are certain metals; certain metallic oxides, carbonates, alkoxides, silicates, borates, acetates and arsenates; and certain organic titanium compounds.  The polyesters, preferably after esterification of their terminal hydroxyl or carboxyl groups, may be used as plasticizers, e.g. for polyvinyl chloride, vinyl chloride, vinyl acetate copolymers, polyvinyl butyral, copolymers of acrylonitrile with butadiene, G.R.S. rubber and natural rubber: thus an acetylated lactone polyester may be milled with a 96 : 4 vinyl chloride-vinyl acetate copolymer together with dibutyl tin maleate as a stabilizer and the mixture moulded into sheets.  The polyester containing terminal hydroxy or carboxyl groups may be reacted with polyisocyanates to form polyurethane rubbers or foams.  In Examples (1)-(27) and (33)-(34) epsilon-caprolactone, certain methyl substituted epsiloncaprolactones and various mixtures thereof were polymerized in the presence of various initiators and catalysts; (28-(32) polyesters were made by reacting together epsilon-caprolactane or certain methyl-epsilon-caprolactones, ethylene glycol and (28) adipic acid, (29) a mixture of glutaric acid and glutaric anhydride; (30) adipic acid; (31) phthalic anhydride (32) isophthalic acid.  Specifications 859,639 859,640, 859,641, 859,643, 859,644 and 859,645 are referred to.