GB907149A - Esters containing epoxide groups, their production and their uses - Google Patents

Abstract

A hardenable composition comprises one or more epoxy esters containing two epoxide groups and having the general formula <FORM:0907149/IV(a)/1> wherein R1, R2, R3, R4, R5, R6, R7, R8 and R9 represent hydrogen atoms or monovalent substituents, e.g. halogen atoms, alkoxy groups, or hydrocarbon residues, n represents 1 or 2 and Z represents the residue of a non-aromatic monocarboxylic acid which contains an epoxide group or a non-aromatic dicarboxylic acid free from epoxide groups, wherein the term non-aromatic excludes only those acids in which a carboxylic group is attached directly to an aromatic nucleus, together with one or more hardening agents for epoxy resins, preferably polycarboxylic acids and their anhydrides. Other hardening agents specified include amines, amides, anilineformaldehyde resins, aminostyrene polymers, isocyanates, isothiocyanates, polyhydric phenols, phenol-aldehyde resins, products of aluminium alkoxides or phenolates with tautomeric compounds, FriedelCrafts catalysts and phosphoric acid. The hardenable mixtures may also contain a proportion of said epoxy ester in which the epoxide groups are complete or partially hydrolysed to hydroxyl groups, and/or other polyhydroxy compounds or other epoxides. The compositions may contain fillers, plasticizers or colouring agents.ALSO:The invention comprises epoxy esters containing two epoxide groups having the formula: <FORM:0907149/IV (b)/1> wherein R1, R2, R3, R4, R5, R6, R7, R8 and R9 represent hydrogen atoms or monovalent substituents such as halogen atoms, alkoxy groups or aliphatic, cycloaliphatic, araliphatic or aromatic hydrocarbon residues, n represents 1 or 2 and Z represents the residue of a non-aromate monocarboxylic acid which contains an epoxide group or stands for the residue of a non-aromatic dicarboxylic acid free from epoxide groups, wherein the term non-aromatic excludes only those acids in which a carboxylic group is attached directly to an aromatic nucleus. The novel esters are made by epoxidation of the corresponding esters containing a carbon-carbon double bond in the ring and, when n is 1, an epoxidisable group in Z, i.e. a double bond or a halohydrin group. The starting materials are made by esterifying D 3-cyclohexanols using the carboxylic acid, anhydride or acid halide, if necessary in the presence of an esterification catalyst, e.g. toluene-p-sulphonic acid. The epoxidation of the double bonds may be effected by treatment with organic peracids, e.g. peracetic, perbenzoic, peradipic or monoperphthalic acid, or by treatment with hypochlorous acid followed by an HCl-eliminating agent, e.g. a strong alkali. The epoxidation of halohydrin groups in Z may be effected with a dehydrohalogenating agent such as potassium hydroxide or sodium hydroxide. Examples describe the preparation of bis-3 : 4-epoxycyclohexyl succinate and 3 : 4-epoxycyclohexyl-3 : 4 - epoxy - tetrahydrobenzoate.