Patent GB-865967-A (GB)
Title: Lactone adducts
IPC: C08G63/08
Filed: 1957-04-10
Abstract: The invention comprises a lactone adduct or a lactone polyester made by reacting a lactone having at least 6 carbon atoms in the ring with a hydroxy carboxylic acid having at least 18 carbon atoms in the molecule or with an ester of a hydroxy carboxylic acid still containing at least one free hydroxy group, and having at least 18 carbon atoms in the molecule.  Suitable lactones include those of formula:-  <FORM:0865967/IV (a)/1> where n is at least 4, at least n + 2 Rs are hydrogen and the remaining Rs are hydrogen, alkyl, cycloalkyl alkoxy or single ring aromatic hydrocarbon radicals; epsilon-caprolactones are preferred in which none of the substituents contain more than 12 carbon atoms, and the total number of carbon atoms in ring substituents does not exceed 12.  Specified esters are 2-ethylhexyl ricinoleate, 3-methyl-1,5-pentanediol diricinoleate, glycerol triricinoleate, glycerol tri-(12-hydroxystearate) and tributyl citrate; ricinoleic and hydroxystearic are the specified acids.  Free hydroxy groups in the adducts or polyesters may be acylated, e.g. with acetic or propionic anhydride.  At least the stoichiometric proportions of lactone is generally used; excess lactone may be used to give adducts with several ester groups in each chain.  The adducts or polyesters are prepared by heating the reactants at 100 DEG -250 DEG C., optionally in the presence of a catalyst such as an organic or mineral acid, a base, or an organic metal compound.  The adducts, or polyesters, particularly after acylation, are stated to be useful as plasticizers, e.g. for vinyl chloride/vinyl acetate copolymers, natural rubber, GRS rubber, acrylonitrile copolymers and nitrocellulose.  Examples are given of vinyl chloride/vinyl acetate copolymer compositions containing adducts according to the invention as plasticizers.ALSO:The invention comprises an adduct of a lactone having at least 6 carbon atoms in the ring with a hydroxy carboxylic acid having at least 18 carbon atoms in the molecule or with an ester of a hydroxy carboxylic acid still containing at least one free hydroxy group, and having at least 18 carbon atoms in the molecule. Suitable lactones include those of formula:  <FORM:0865967/IV (b)/1> where n is at least 4, at least n + 2 Rs are hydrogen and the remaining Rs are hydrogen, alkyl, cycloalkyl, alkoxy or single ring aromatic hydrocarbon radicals; epsilon-caprolactones are preferred in which none of the substituents contain more than 12 carbon atoms, and the total number of carbon atoms in ring substituents does not exceed 12.  Specified esters are 2-ethylhexyl ricinoleate, 3-methyl-1, 5-pentanediol diricinoleate, glycerol triricinoleate, glycerol tri-(12-hydroxystearate) and tributyl citrate; ricinoleic and hydroxystearic are the specified acids.  Free hydroxy groups in adducts may be acylated e.g. with acetic or propionic anhydride.  At least the stoichiometric proportion of lactone is generally used; excess lactone may be used to give adducts with several ester groups in each chain.  The adducts are prepared by heating the reactants at 100-250 DEG C. optionally in the presence of a catalyst such as an organic or mineral acid, a base, or an organic metal compound.  The adducts, particularly after acylation, are stated to be useful as plasticisers, e.g. for vinyl chloride/vinyl acetate copolymers, natural rubber, GRS rubber, acrylonitrile copolymers and nitrocellulose.  3-Methyl-1, 5-pentanediol diricinoleate is prepared as starting material in Example 7.