Patent GB-576317-A (GB)
Title: Resinous products from castor oil and production of same
IPC: C09F5/06
Filed: 1943-11-25
Abstract: Coating materials for food containers are prepared by mixing castor oil with a neutral polybasic acid ester of an unsaturated alcohol, which unsaturated alcohol contains an olefinic linkage between two carbon atoms, one of which is directly linked by a single bond to the carbinol group, heating the mixture in the presence of a dehydration catalyst to dehydrate the castor oil so as to split out water chemically from and simultaneously heat-body the reaction mixture, separating the unreacted monomeric polybasic acid ester from the reaction mixture, hardening the resulting resinous material by heating it to a temperature above 100 DEG  C., and dissolving in a solvent.  Esters specified are diallyl carbonate, diallyl oxalate, dimethallyl oxalate, diallyl succinate, diallyl adipate, dimethallyl carbonate, dimethallyl succinate, dimethallyl adipate, diallyl phthalate, diallyl maleate, diallyl terephthalate, diallyl diglycollate, triallyl citrate, di - (beta - chlorallyl) succinate, di-(beta-chlorallyl) phthalate, di-(methyl vinyl carbinyl) adipate, di-(methyl vinyl carbinyl) phthalate, dicrotyl mesaconate, dicrotyl phthalate, dicinnamyl glutarate, dicinnamyl phthalate, triallyl borate, triallyl phosphate, trimethallyl borate, tricinnamyl phosphate, allyl methallyl phthalate, allyl cinnamyl adipate, dimethallyl crotyl borate.  Heating is effected in the range of from 150 DEG  C. to 350 DEG  C., preferably 200 DEG  C. to 300 DEG  C. or at two temperatures, namely 220 DEG  C. to 240 DEG  C. and 260 DEG C. to 300 DEG  C.  Catalysts specified are sodium and potassium bisulphate, bentonite, p-toluene sulfonic acid, tungsten trioxide, phosphorous pentoxide, phosphoric acid, sulfuric acid, boron oxide, molybdenum oxide, kaolin, ammonium acid sulfate, copper sulfate, aluminium sulfate, ferric sulfate, potassium alum, ferric ammonium alum, phthalic anhydride and maleic anhydride.  The monomer may be separated by solvent precipitation, for example, by adding alcohols or ethers to a solution of the product in acetone, or by vacuum distillation in presence of polymerization inhibitors, e.g. phenols, cresols tertiary amyl phenol, tertiary butyl phenol, dimethyl tertiary butyl phenol, hydroquinone, naphthols, carvacrol, thymol, the quinones, the amines, the alkylol amines, the nitro-aryl compounds, such as tri-ethyl amine, aniline, the naphtholamines, the phenylene diamines, pyridine, tetra phenyl hydrazine, acetaldehydeammonia, amino phenols, amino naphthols, ethanolamine, tri-ethanolamine, nitro-benzene, and amino nitro phenols, inorganic materials such as copper, copper alloys, elemental sulfur, selenium, tellurium, and iodine.  The product may be clarified by agitating with lime and filtration by diatomaceous earth.  Phosphoric acid may be added to the product to produce a colourless film, and solvents specified are benzene, toluene, xylene, hexane, octanes, naphtha, or combinations thereof, acetone, methyl ethyl ketone, methyl propyl ketone, mesityl oxide, methyl isobutyl ketone, isophorone, cyclohexanone, ethyl acetate, isopropyl acetate, normal butyl acetate, secondary butyl acetate, ethyl propionate, butyl butyrate and amyl acetate. Siccatives may be added to shorten the baking time of the solution, namely, lead cobalt and/or manganese resinates, lineolates and naphthenates.  Solutions of the product are used for impregnating wood, paper and cloth and for preparing oilcloth, linoleum and plywood or for the manufacture of moulded articles. Dyes, plasticisers, pigments may be incorporated.  In examples, diallyl phthalate and castor oil are mixed with sodium bisulfate and heated.  The monomeric material is removed by distillation in presence of 2.4-dimethyl-6-tertiary butyl phenol, and the product is formed into a coating composition by dissolving in toluol, xylol, or secondary butyl acetate.  Specification 576,316 is referred to.