Patent GB-819018-A (GB)
Title: Improvements in or relating to resinous polyhydric phenols
IPC: C08G63/06
Filed: 1956-05-31
Abstract: New polyester resins are the interesters of a 4,4 - bis - (4 - hydroxyphenyl) - pentanoic acid of formula <FORM:0819018/IV (a)/1> where x and y are a hydrogen atom, a lower alkyl radical or a halogen atom.  The interesters preferably contain 2-15 recurrent units.  They may be made (a) by heating the diphenolic acid in presence of acetic anhydride, any excess anhydride resulting in acetylation of the free phenolic hydroxyl groups, or (b) by converting the carboxyl group of the diphenolic acid to an acid chloride group which immediately reacts with the phenolic hydroxyl groups.  The phenolic hydroxyl groups in the interesters may be esterified with unsaturated monocarboxylic acids containing at least 10 carbon atoms, e.g. the acids of chinawood, oiticica, linseed, soyabean, corn, cottonseed, dehydrated castor, menhaden or sardine oil, or oleic, or underenoic acid, or a mixture of oleic and linoleic acids.  These esters may be prepared by (c) effecting reaction (a) in presence of the acid (d) re-esterifying the acetylated product of process (a) with the acid or (e) esterifying the interester with the acid chlorides of the acid. The new resins are useful as adhesive or as moulding composition but are especially useful in coating compositions to which end they may be dissolved in an organic solvent (e.g. xylol or naphtha) and have a cobalt drier added thereto.  The examples describe the interesterification of 4,4-bis-(4-hydroxyphenyl)-pentanoic acid and methyl, dimethyl and dichloro nuclear substituted derivatives thereof and the esterification of these interester with some of the monocarboxylic acids specified above.  Specifications 768,206 and 790,373 are referred to.ALSO:New esters are the interesters of a 4,4-bis-(4-hydroxyphenyl)-pentanoic acid of formula <FORM:0819018/IV (b)/1> where x and y are a hydrogen atom, a lower alkyl radical or a halogen atom.  The interesters preferably contain 2-15 substituted pentanoic acid residues, an example of a low molecular weight compound being <FORM:0819018/IV (b)/2> They may be made (a) by heating the diphenolic acid in presence of acetic anhydride, any excess of the anhydride resulting in acetylation of the free hydroxyl groups, or (b) by converting the carboxyl group of the diphenolic acid to an acid chloride group which immediately reacts with the phenolic hydroxyl group. The phenolic hydroxyl groups in the interesters may be esterified with unsaturated monocarboxylic acids containing at least 10 carbon atoms, e.g. the acids of chinawood, oiticica, linseed, soya bean, corn, cottonseed, dehydrated castor, manhaden or sardine oil, or oleic, undecenoic or a mixture of oleic and linoleic acids.  These esters may be prepared by (c) effecting reaction (a) in the presence of the acid, (d) re-esterifying the acetylated product of process (a) with the acid or (e) esterifying the interester with the acid chloride of the acid.  The examples describe the interesterification of 4,4-bis-(4-hydroxyphenyl)-pentanoic acid and methyl, dimethyl and dichloro nuclear substituted derivatives thereof and the esterification of these interesters with some of the monocarboxylic acids specified above.  The nuclear unsubstituted and nuclear alkyl substituted acids may be prepared as described in Specifications 768,206 and 790,373.  The dichloro substituted acid is prepared in Example 13 by reacting the ethyl ester of 4,4-bis-(4-hydroxyphenyl)-pentanoic acid with sulphonyl chloride.