ES260356A1 - New epoxide compounds - Google Patents

Abstract

The invention comprises epoxide compounds of the formula: <FORM:0950285/C2/1> in which R1 and R2 represent methyl groups or hydrogen atoms and n=1 or 2. The novel compounds may be made by treating a compound of the formula: <FORM:0950285/C2/2> with a dehydrohalogenating agent to convert the halohydrin group to a 1:2 epoxide group and, if desired, epoxidising the carbon-to-carbon double bond in the cyclopentene ring, in any desired order of succession. As dehydrohalogenating agent, a strong alkali, such as sodium hydroxide or potassium hydroxide, is suitable. The double bond may be epoxidised with an organic per-acid such as peracetic, perbenzoic peradipic or monoperphthalic acid. Alternatively, the compound may be treated with hypochlorous acid followed by strong alkali. The starting materials of formula II may be made either (1) by an additive reaction of a monohalohydrin: <FORM:0950285/C2/3> where Hal is halogen, for example bromine or chlorine, with dicyclopentadiene in the presence of an acid catalyst or of a Lewis. acid, such as sulphuric acid or boron fluoride or a boron fluoride complex or (2) by condensing an epihalohydrin of the formula: <FORM:0950285/C2/4> with dihydrodicyclopentadiene -8- ol. Detailed examples are given.ALSO:Curable mixtures comprise diepoxides of the formula: <FORM:0950285/C3/1> in which R1 and R2 represent methyl groups or, preferably, hydrogen atoms and n is 2 or a curing agent for epoxide compounds, e.g., an amine or amide, anilene-formaldehyde resin, urea-formaldehyde resin, melamine-formaldehyde resin, polymer of aminostyrine, polyamide, isocyanate, isothiocyanate, polyhydric phenol, phenol-aldehyde resin, oil-modified phenol-aldehyde resin, reaction product of an aluminium alcoholate or phenolate with a compound of tautomeric reaction, a Friedel-Crafts catalyst, phosphoric acid, or preferably a di- or polybasic carboxylic acid or anhydride thereof. An accelerator such as a tertiary amine or polyhydroxy compound may also be added. The curable mixtures may also contain a proportion of the above epoxide compounds whose epoxide groups are wholly or partially hydrolysed and as active diluents, mono-epoxides. Further polyepoxides such as mono- or polyglycidyl ethers of mono or polyalcohols or phenols, polyglycidyl esters of polycarboxylic acids, and aminopolyepoxides. Fillers, plasticisers or colouring matters may also be added, e.g., asphalt, bitumen, glass fibres, mica, quartz meal, cellulose, kaolin, silicic acid or metal powders.