Patent GB-844312-A (GB)
Title: Epoxy alcohol and ethers or esters thereof
Inventor: PHILLIPS BENJAMIN
IPC: C08G59/24
Filed: 1957-11-23
Abstract: 2, 3-Epoxycyclopentanol (for preparation see Group IV(b)), may be polymerized with itself or with other monoepoxides or polyepoxides to produce resins.  It may also be used as a reactive diluent with polyepoxides and in such arts as casting, coating, laminating and bonding.  It may be used to reduce the viscosity of many liquid epoxide systems to which powdered oxide or fibrous fillers are added. This epoxy alcohol may be polymerized with polycarboxylic acids or polycarboxylic anhydrides to produce resins.  2, 3-epoxycyclopentanol ethers and esters are useful on the synthetic resins ant as monomers, reactive diluents, plasticizers, stabilizers mould release agents, or lubricants. The mono-epoxy ethers and esters are particularly useful as stabilizers for chlorine-containing resins such as polyvinyl chloride, polyvinylidene chloride or chlorinated synthetic rubbers. The ethers and esters can be polymerized to form viscous liquids which can be incorporated with other synthetic resins such as polystyrene and ethyl cellulose as plasticisers, lubricants and mould release agents.  Ethers and esters containing more than one epoxy group can also be polymerized and can be incorporated with and polymerized with other epoxides and polyepoxides to form new epoxide resins.  Ethers and esters of 2, 3-epoxycyclopentanol which contain an ethylenically unsaturated group may be polymerized through the unsaturated group to form a two-dimensional resin, and subsequently the polymer can be cured to produce a cross-linked three-dimensional resin.  These unsaturated ethers and esters of 2, 3-epoxycyclopentanol may also be copolymerized with other ethylenically unsaturated monomers such as ethylene, propylene, vinyl chloride, vinylidene chloride, vinyl acetate, styrene or acrylonitrile.  An example describes the polymerization of allyl 2, 3-epoxycyclopentyl ether through its unsaturated groups in the presence of acetyl peroxide in dimethyl phthalate.  Specification 812,374 is referred to.ALSO:The invention comprises 2-3-epoxycyclopentanol and ethers and esters thereof.  The ether and ester radicals specified include aliphatic, cycloaliphatic, aromatic and epoxidised aliphatic and cycloaliphatic radicals.  The novel compounds may be prepared by reacting 2-cyclopentenol or ethers or esters thereof with an epoxidizing agent, such as acetaldehyde monoperacetate, or peracetic acid, at a temperature of from -25 DEG C. to 150 DEG C., and preferably in the presence of an inert solvent. The preferred 2-cyclopentenyl ethers and esters are those in which the ether or ester radical is an aromatic, open chain aliphatic or monocyclic aliphatic group.  The particularly preferred ethers are those which contain not more than 23 carbon atoms and not more than 2 oxygen atoms and the most preferred esters are those which contain not more than 23 carbon atoms and not more than 3 oxygen atoms. The 2-cyclopentenyl starting materials may be obtained by reacting cyclopentadiene with anhydrous hydrogen chloride at about 0 DEG C. to -15 DEG C. to obtain 1-chloro-2-cyclopentene which is subjected to hydrolysis with sodium hydroxide or carbonate to yield 2-cyclopentenol.  The latter may be reacted with a monohydric alcohol in the presence of an acid catalyst such as boron trifluoride dietherate and mercuric oxide to form an ether, or with a carboxylic acid, at temperatures up to 94 DEG C. or higher, with or without a catalyst or solvent, to form an ester. 2-cyclopentenyl chloride and a monohydric compound or sodium derivative thereof may also be reacted in the presence of potassium or sodium carbonate to form an ether. Polyethers and polyesters of 2-cyclopentenol may be prepared by similar procedures to those described above and epoxidised to form the corresponding polyethers and polyesters of 2,3-epoxycyclopentanol.  The novel 2,3-epoxycyclopentanol and ethers and esters thereof are useful in the synthetic resins and as monomers, reactive diluents, plasticisers, stabilizers, mould release agents, or lubricants.  They may be polymerized or copolymerized to produce synthetic resins.  Specification 812,374 is referred to.