Patent GB-792028-A (GB)
Title: Esters of polyhydric alcohols and pentanoic acids
IPC: C11C3/00
Filed: 1956-04-06
Abstract: Esters of a polyhydric alcohol and a nuclear substituted or unsubstituted 4,4-bis-(hydroxy phenyl) pentanoic acid, and mixed esters of a polyhydric alcohol, a pentanoic acid (as above) and at least one unsaturated acid free of hydroxyl or epoxy groups and having 10 to 36 carbon atoms, are prepared.  Examples are given of the preparation of esters from 4,4-bis(4-hydroxy phenyl) pentanoic acid and the following polyhydric alcohols, ethylene glycol, glycerol, methyl a -d-glucoside, diethanolamine, trimethylol ethane, sorbitol, pantaerythritol.  Suitable acids for preparing the mixed esters are those obtained from china wood oil, oiticica oil, linseed oil, soyabean oil, corn oil, cottonseed oil, and oils from menhaden and sardine; linoleic acids, and undecenoic acid, the decomposition product of castor oil acids. Esterification of the polyhydric alcohols with diphenolic acid may be carried out by heating at temperatures from 190-275 DEG  C. under conditions such that the water produced during condensation is continuously removed as it is formed.  Lower temperatures may be used when a resinous compound containing epoxide groups and alcoholic hydroxyl troups is esterified only to the extent of one carboxyl group reacting with one epoxide group.  Any water formed during the reaction may be removed by permitting it to volatilize during esterification, by continuously bubbling an inert gas through the reaction mixture, or by refluxing in such a way with a volatile, water insoluble solvent that the water is continuously removed by azeotropic distillation and dropped into a water trap, the solvent being returned to the reaction mixture. Specifications 768,206 and 790,373 are referred to.ALSO:Esters of a polyhydric alcohol and a nuclear substituted or unsubstituted 4,4-bis-(hydroxyphenyl) pentanoic acid, and mixed esters of a polyhydric alcohol, a pentanoic acid (as above) and at least one unsaturated acid free of hydroxyl or epoxy groups and having 10-36 carbon atoms are prepared.  Suitable polyhydric alcohols are polyethylene glycol,of molecular weight 3350, polypropylene glycol, a resinous polyhydric alcohol containing some epoxide, prepared from epichlorohydrin and bis-(4-hydroxyphenyl) isopropylidene and similar compounds, and the reaction product of p-tertiary butylphenol with formaldehyde and ethylene chlorohydrin.  Suitable acids for preparing the mixed esters are those obtained from china wood oil, oiticica oil, linseed oil, soyabean oil, corn oil, cottonseed oil, sardine and menhaden oils, linoleic acids and undecanoic acid, the decomposition product of castor oil acids.  The esterification process may be carried out by heating the polyhydric alcohols with the acids at temperatures from 190-275 DEG  C. under conditions such that the water produced during condensation is removed as it is formed.  Lower temperatures may be used when a composition of the Epon resin type is esterified only to the extent of one carboxyl group reacting with one epoxide group.  Any water formed during the reaction may be removed by permitting it to volatilize during esterification, by continuously bubbling an inert gas through the reaction mixture or by refluxing in such a way, with a volatile water insoluble solvent, that the water is continuously removed by azeotropic distillation and dropped into a water trap, the solvent being returned to the reaction mixture. Specifications 768,206 and 790,373 are referred to.