Patent GB-936346-A (GB)
Title: Resins containing epoxide groups, their production and their uses
Inventor: HUMPHREYS KEITH WOOD
IPC: C07D303/24
Filed: 1960-05-04
Abstract: A hardenable composition comprises one or more mixtures of isomeric compounds of the formula <FORM:0936346/IV(a)/1> wherein X and Y are the same or different and each represents a hydrogen atom, an aliphatic, cycloaliphatic, araliphatic or aromatic hydrocarbon radical or a said radical containing an epoxy group, together with one or more hardening agents therefore.  Suitable hardeners are amines, amides, aniline-formaldehyde resins, polymers of amino-styrenes, polyamides, isocyanates, isothiocyanates, polyhydric phenols, phenol-aldehyde resins, reaction product of aluminium alkoxides or phenolates with tantomeric-reacting compounds, Friedel-Crafts catalysts and their complexes with organic compounds, and phosphoric acid.  Preferred hardeners are di- or polybasic carboxylic acids and their anhydrides.  Accelerators such as tertiary amines and polyhydroxy compounds may also be present. The compositions may contain a proportion of compounds of the above formula in which the epoxide groups are completely or partially hydrolysed to hydroxyl groups.  Other epoxides may be present such as mono- or poly-glycidyl ethers of mono- or poly-alcohols, or mono- or poly-phenols, polyglycidyl esters of polycarboxylic acids, or aminopolyepoxides.  The compositions may also contain asphalt, bitumen, glass fibres, mica, quartz powder, cellulose, kaolin, finely divided kieselguhr or metal powder.  In an example, the bisepoxide of bis-dihydrodicyclopentadienyl formal is hardened with phthalic anhydride and triamylammonium phenate.ALSO:The invention comprises a mixture of isomeric compounds of the general formula: <FORM:0936346/IV(a)/1> wherein X and Y are the same or different and each represents a hydrogen atom, an aliphatic, cycloaliphatic, araliphatic or aromatic hydrocarbon radical or a said radical containing an epoxy group.  The compounds may be made by epoxidising a mixture of isomeric compounds of the general formula <FORM:0936346/IV(a)/2> wherein X1 and Y1 have the meanings assigned to X and Y, or where X and Y in the product contain epoxy groups, are corresponding groups containing unsaturated epoxidisable linkages. The epoxidation may be effected by treatment with organic peracids, e.g. peracetic, perbenzoic, peradipic or monoperphthalic acids, or by treatment with hypochlorous acid followed by treatment with an HCl-eliminating agent, e.g. a strong alkali.  The unsaturated acetal or ketal starting materials may be made by reaction of tricyclo-(5:2:1:02,6)-dec-3-ene-8 (and 9) -ol (obtained by hydration of dicyclopentadiene) with aliphatic, cycloaliphatic or aromatic aldehydes or ketones in the presence of a dehydrating agent such as a suitable anhydrous salt or a strong acid.  Alternatively, a trans-alkylation reaction may be effected between an acetal or ketal of the appropriate aldehyde or ketone and a low-boiling alcohol, and dihydrodicyclopentadienol in the presence of strong acid catalysts. A further method for making the unsaturated acetals and ketals derived from acetaldehyde or acetone involves reaction of dihydrodicyclopentadienol with vinyl acetate or isopropenyl acetone in the presence of a catalyst consisting of mercuric oxide and the boron trifluoride-diethyl ether complex.  Detailed examples are given.