An aryl substituted pentanoic acid ester and method of making the same

摘要

Esters of the general formula: (where R and R1 are para-hydroxyphenyl or C1-C5 mono or dialkyl substituted ortho or para hydroxyphenol. R11 is alkenyl radical with 10-36 carbon atoms) are prepared from a monohydric unsaturated alcohol with 10-36 carbon atoms and an acid of the general formula: Suitable aryl-substituted pentanoic acids are those produced by the condensation of levulinic acid with phenol or a substituted phenol. Suitable alcohols are those produced by the reduction of naturally occurring unsaturated oils such as china wood oil, dehydrated castor oil, linseed oil, soya bean oil, corn oil, cottonseed oil and fish oils. Specified alcohols are those prepared from soyabean oil, linseed oil and a mixture of C10, C18 and C20 alcohols, also undecenol prepared by reduction of undecenoic acid, and octadecadienol from methyl oleate by oxidation to dihydroxymethyl stearate followed by dehydration and reduction. The esters are prepared by heating the acid and alcohol at 190-275 DEG C., the water so produced being continuously recovered as it is formed through a water trap attached to the condenser during the reaction or by any other suitable means. The products are used in the preparation of protective coating materials, by heating with formaldehyde using hydrochloric acid as a catalyst. Specifications 768,206 and 790,373 are referred to.ALSO:Esters of general formula (where R and R1 are parahydroxyphenol or C1-C5 mono or dialkyl substituted ortho or para hydroxyphenol, R11 is alkenyl with 10-36 carbon atoms) are used for coating steel panels. An example is given of the use of an ester prepared from a diphenolic acid (prepared from phenol and levalinic acid) and an alcohol prepared by reduction of a soyabean oil, having an iodine value 138-154. The ester is treated with 37 per cent aqueous formaldehyde using HCl as catalyst, and heated. After removal of water the resinous amber product is dissolved in a solvent consisting of a mixture of butyl acetate, butanol, and methyl isobutyl ketone. Thin films of this product are then flowed on steel panels and baked for 15 mins. at 200 DEG C. Specifications 768,206 and 790,373, [both in Group IV (a)], are referred to.ALSO:Esters of general formula: (where R and R1 are parahydroxyphenol or C1-C5 mono or dialkyl substituted ortho or para hydroxyphenol, R11 is alkenyl with 10-36 carbon atoms) are condensed with aldehydes or epoxides to form resinous products. An example is given of the condensation with 37 per cent aqueous formaldehyde of an ester prepared from diphenolic acid (prepared from phenol and levulinic acid) and an alcohol prepared by the reduction of a soyabean oil having an iodine value 138-154. Films are prepared from a solution of the resulting resin in equal parts of butyl acetate, butanol and methyl isobutyl ketone. Specifications 768,206 and 790,373 are referred to.