Hydroxyaryl-substituted acid-esterified acid esters and method of making the same

摘要

Esters are prepared by reacting (1) an hydroxyaryl-substituted acid which is the condensation product of a phenol and an aliphatic keto acid having its carbonyl group adjacent to the terminal carbon atom; and (2) an ester of an alcohol and an aliphatic acid having from 10 to 36 carbon atoms containing at least one radical of the group consisting of hydroxyl or epoxy. Suitable hydroxylated or epoxidized long-chain acid esters are those of vegetable oils or fish oils, e.g. castor oil, oiticica oil, corn oil, cottonseed alcohols as pentaerythritols, glycols, methyl, ethyl and butyl alcohols, or those prepared from e.g. a mixture of phthalic anhydride, soya bean oil acids and glycerol, also the mixed esters of a polylol, a polycarboxylic acid and a long-chain monocarboxylic acid. Suitable hydroxyaryl-substituted acids are the condensation products of levulinic acid and phenol, substituted phenols or mixtures thereof. The phenols may be substituted with alkyl groups or halogens. Examples are given of the preparation of esters from 4,4-bis(4-hydroxyphenol)-pentanoic acid and (1) castor oil, (2) blown castor oil, (3) epoxidized butyl oleate, (4) epoxidized soya bean oil having an equivalent weight to epoxide of 260. Specifications 768,206 and 790,373 are referred to.ALSO:Esters are prepared by reaction of (1) an hydroxyaryl substituted acid which is the condensation product of a phenol and an aliphatic keto acid having its carbonyl group adjacent to the terminal carbon atom, and (2) an ester of an alcohol and an aliphatic acid having from 10-36 carbon atoms containing at least one radical of the group consisting of hydroxyl or epoxy. The ester of the aliphatic acid of 10-36 carbon atoms may be a complex product such as an epoxidized alkyd resin prepared from a mixture of phthalic anhydride soya bean oil acids and glycerol. It may be a mixed ester of a polyol, a polycarboxylic acid and a long chain monocarboxylic acid. In one example an alkyd resin is prepared from glycerol oleic acid and phthalic acid, epoxidized with hydrogen peroxide and is then esterified with 4,4-bis(4hydroxy phenyl) pentanoic acid to give a hard resin having an acid value of 17.1 and a softening point of 80 DEG C. In another example the ester, having an acid value of 13.5, produced by the reaction of 4,4-bis(4-hydroxyphenyl) pentanoic acid and castor oil is condensed with paraformaldehyde in the presence of methyl isobutyl ketone and toluenesulphonic acid, to produce thin films, which on heating give a hard tack-free flexible product. A similar type of product is obtained using epoxidized butyl oleate (equivalent weight to epoxide 410) instead of castor oil. Specifications 768,206 and 790,373 are referred to.