Patent GB-943925-A (GB)
Title: Mixtures of compounds containing epoxide groups, their production and their uses
Inventor: HUMPHREYS KEITH WOOD
IPC: C08G59/14
Filed: 1960-05-04
Abstract: The invention comprises a mixture of isomeric monoepoxy compounds of the general formula: <FORM:0943925/C2/1> where R represents a hydrogen atom or an alkyl, alkenyl, hydroxyalkyl, hydroxyalkoxyalkyl, polyhydroxyalkyl or hydroxy (polyalkoxy)-alkyl group.  The mixtures of isomeric compounds may be made by epoxidising a corresponding mixture of isomeric unsaturated compounds, for example by treatment with organic peracids, e.g. peracetic, perbenzoic, peradipic or monoperphthalic acid, preferably at 0 DEG  to 40 DEG C.  The unsaturated alcohols and ethers used as starting materials for the epoxidation may be obtained by reaction of dicyclopentadiene with water or an alcohol ROH, if necessary, in the presence of a strong acid or Lewis acid.  A mixture of isomeric alcohols or ethers results. Suitable alcohols are methyl, ethyl, propyl, or allyl alcohols, glycerine, sorbitol, mannitol, pentaerythritol, ethylene glycol, polyethylene glycols, propylene glycol and poly-propylene glycols.ALSO:A mixture of isomeric monoepoxy compounds of the general formula: <FORM:0943925/C3/1> where R represents a hydrogen atom or an alkyl, alkenyl, hydroxyalkyl, hydroxyalkoxy-alkyl, polyhydroxyalkyl or hydroxy- (polyalkoxy)-alkyl group, reacts with the usual hardeners for epoxy compounds.  Suitable hardeners are amines, amides aniline formaldehyde resins, polymers of amino-styrenes, polyamides, isocyanates, isothiocyanates, polyhydric phenols, phenol-aldehyde resins, reaction products of aluminium alkoxides or phenolates with tautomeric-reacting compounds, Friedel-Crafts catalysts and their complexes with organic compounds and phosphonic acid.  Preferred hardeners are polybasic carboxylic acids and their anhydrides. Accelerators such as tertiary amines and polyhydroxy compounds may also be present.  A preferred hardenable composition comprises a mixture of the isomeric monoepoxy compounds together with a di- or poly-epoxide and one or more hardening agents.  Other epoxides include polyepoxides of alicyclic compounds, polyglycidyl ethers of polyalcohols or of polyphenols, polyglycidyl esters of polycarboxylic acids, or aminopolyepoxides.  There may also be included compounds in which the epoxide groups of the above general formula are hydrolysed to hydroxyl and/or acyloxy groups. The compositions may also contain fillers, plasticizers or colouring agents, e.g. asphalt, bitumen, glass fibres, mica, quartz powder, cellulose, kaolin, finely-divided kieselguhr or metal powder.  In an example, a composition comprising a mixture of the above formula where R is hydrogen, a polyglycidyl ether (obtained from epichlorohydrin and bis (4-hydroxyphenyl) dimethyl methane in alkali) phthalic anhydride with or without tris-(dimethylaminomethyl) phenol as accelerator, is hardened, first for 3 hours at 120 DEG C., then for 24 hours at 160 DEG C.  Isomeric compounds of the formula: <FORM:0943925/C3/2> are prepared by reacting dicyclopentadiene with an alcohol which may be a polyethylene or polypropylene glycol of molecular weight up to 1,000. Epoxidation of these compounds yields the compounds of formula (1).