Patent GB-549515-A (GB)
Title: Improvements relating to the production of synthetic resins from furfuryl alcohol
IPC: C08G16/02
Filed: 1941-03-20
Abstract: 549,515. Resins from furane derivatives. BRITISH THOMSON-HOUSTON CO., Ltd. March 20, 1941, No. 3798. Convention date, March 26, 1940. [Class 2 (iii)] Liquid resinous materials are prepared by heating furfuryl alcohol, or a mixture of furfuryl alcohol and furfural, together with a hardening catalyst consisting of an inorganic salt of an amine or of an amide, dehydrating the product after heating for about half an hour and before the resinous material loses its fluid state, and then adding an alkaline substance to adjust the pH value to between 4 and 6. The resinous materials are capable of being stored for three months or more in the absence of air without loss of their fluid state, but are capable of hardening to an insoluble infusible solid state when heated at from about 50‹ to 150‹C., with or without the addition of a further amount of the catalyst. Specified catalysts are the mineral acid salts of urea, thiourea, substituted ureas such as phenyl thiourea, and methyl, acetyl, benzoyl, asymmetrical diethyl, allyl, 2-chlorallyl, ethylidine and methylol urea, guanidine, dicyandiamide, guanyl urea, biguanidine, amino-guanidine, creatine, creatinine, guanoline, ethanol amines such as mono-, di- and tri-ethanolamines, tri-isopropanolamine, phenyl ethanolamine, ethyl phenyl ethanolamine, phenyl diethanolamine, diethylaminoethanol, ethylene diamine, diethylene triamine, triethylene tetramine, alkyl amines such as methyl, trimethyl, ethyl and propyl amines, aryl amines such as aniline and benzyl amine, acetoacetanilide, orthochloroacetoacetanilide, dichloroacetoacetanilide, morpholine, and phenyl morpholine. The salts may be derived from sulphuric, nitric or the halogen acids. In examples resinous materials are prepared (1) by heating furfuryl alcohol with urea monohydrochloride, and dehydrating the product under vacuum. The pH of the liquid resin is then adjusted, to promote storage stability, by the addition of hexamethylene tetramine, calcium or barium hydroxide, an alkali-metal hydroxide or carbonate, ammonia, an ethanolamine, an alkyl or aryl amine, or a mixture of ammonia and an amine. When heated, the liquid resin hardens to a dense, black, insoluble and infusible mass ; (2) furfuryl alcohol is heated with aniline hydrochloride, the product is dehydrated, and the pH is then adjusted by the addition of aniline. The liquid resins are practically insoluble in alcohol, but are soluble in dioxane, ethyl acetate, toluene, benzene and ethylene glycol monoethyl ether; they are suitable for use as bonding and impregnating agents, acid-resistant mortars, in the production of wire enamels, and in casting applications ; they may have incorporated therein fillers, e.g. sand, pumice, asbestos, mica, glass, fire clays, bentonite, magnesia, chromites, iron oxides, metals, wood flour, α-cellulose, cloth or paper, dyes, pigments of natural or synthetic resins. According to the Specification as open to inspection under Sect. 91, the process may be applied to liquid furane derivatives in general, the catalyst being a substance which is effective in polymerizing the furane derivative without a violent exothermic reaction, e.g. an inorganic acid salt of an organic compound. Specified furane derivatives are alkyl furane alcohols, e.g. methyl and ethyl furfuryl alcohols, halofurfuryl alcohols, e.g. chloro-, bromo- and fluoro-furfuryl alcohols, furfuryl aldehydes, e.g. furfuryl acrolein, halofurfurals, e.g. chlorobromo and fluoro-furane aldehydes, furfuryl ketones, e.g. furfuryl acetone, and furfuryl acetals, e.g. furfuryl formal, propional and furfural. This subject-matter does not appear in the Specification as accepted.