GB869997A - Process for the production of condensation products - Google Patents

Abstract

A process for the production of condensation products comprises reacting one or more isocyanates and/or polyisocyanates, in the presence of an acid catalyst, with one or more organic compounds comprising one or more groups of the general formula -O,CH2X in which X represents chlorine or bromine. Examples of such compounds are the reaction products of methyl alcohol, hydrogen chloride and an oxo compound such as formaldehyde, acetaldehyde, benzaldehyde or glyoxal. Monoisocyanates mentioned are phenyl, alkyl or aryl phenyl, halophenyl, nitrophenyl, carbalkoxy phenyl and cyanophenyl isocyanates; isocyanato-benzyl ethers and aliphatic, araliphatic or hydroaromatic isocyanates, including alkyl, allyl, cyclohexyl, benzyl and chloropropyl isocyanates and isocyanato-acetic acid esters. Polyisocyanates listed are tetramethylene, hexamethylene, and thiodipropyl diisocyanates, o , o 1-di-isocyanatoalkyl benzenes or naphthalenes, cyclohexane and aryl diisocyanates, derivatives of alkyl and aryl-substitution products of benzene and naphthalene and their hydrogenation products, 3-(a -isocyanato-ethyl) phenyl isocyanate and diphenyl ether and diphenyl sulphone polyisocyanates. Reaction products (still containing isocyanate groups) of the polyisocyanates with alcohols, phenols, amines, polyesters, polyethers, polythioethers and polyacetals are also suitable. Catalysts specified are hydrochloric acid, BF3, BCl3 and their adducts, FeCl3, CrCl3, SbCl5, SnCl4 and sulphuric and phosphoric acids. Reaction may be effected in aliphatic and aromatic hydrocarbons, chlorinated hydrocarbons, ethers, esters or ketones. The halomethyl groups are polyfunctional and the products are soluble resins or insoluble cross-linked plastics. Free isocyanate groups may be present. The products may be used as substances which split off isocyanates on heating. Those containing free isocyanate groups can be used together with polyhydroxy or polyamino compounds in lacquers, coatings or adhesives. Those with double bonds can be polymerized to form moulded elements. Examples describe production of resins and brittle masses by the reaction of (1) to (8) methyl chloromethyl ether and (1) phenyl isocyanate in the presence of BF3 etherate; (2) phenyl isocyanate in the presence of sulphuric acid; (3) phenyl isocyanate in the presence of BF3 etherate in chlorobenzene solution; (4) phenyl isocyanate in the presence of antimony pentachloride or tin tetrachloride; (5) toluylene 2, 4- and 2, 6-diisocyanates in the presence of BF3 etherate; (6) and (7) toluylene-2, 4-diisocyanate; (8) hexamethylene diisocyanate; (9) n-octyl chloromethyl ether and phenyl isocyanate in the presence of BF3 etherate; (10) phenyl isocyanate and hexanediol-1, 6- dichloromethyl ether. The product of Example (6) contains free NCO and toluylene diisocyanate and is soluble in acetone, glycol monomethyl ether acetate and dimethyl formamide. It is mixed with a hydroxy polyester of adipic acid, trimethylol propane and butylene glycol to form a lacquer.