Patent GB-812374-A (GB)
Title: A new epoxide ether, polymerisation products thereof, and their preparation
IPC: C08G59/24
Filed: 1955-12-08
Abstract: Essential oils and perfumed soaps are stabilized by incorporating therein the bis-cyclopentenyl ether diepoxide of the formula <FORM:0812374/III/1> Its preparation is given (see Group IV (b)).ALSO:The invention comprises homo-polymers of bis-cyclo pentenyl ether di-epoxide of the formula <FORM:0812374/IV (a)/1> and copolymers of this di-epoxide with other epoxy materials, e.g. ethylene oxide, propylene oxide, butylene oxide, styrene oxide, vinyl cyclohexene oxide, allyl glycidyl ether or dicyclo pentadiene epoxide.  They may be prepared by polymerization in the presence of an acidic polymerization catalyst, e.g. BF3, AlCl3, SnCl4, ZnCl2, H3PO4, HF and HF treated clay.  Examples describe the homopolymerization of the diepoxide or copolymerization of equimolar amounts of the diepoxide and propylene oxide using BF3 in toluene as the catalyst.  The polymeric products and the monomeric biscyclopentenyl ether diepoxide, whose preparation is given (see Group IV (b)), may be used to stabilize resins especially chlorine-containing resins such as polyvinyl chloride, neoprene, polyvinylidene chloride and chlorendic acid polyesters.ALSO:The invention comprises the di-epoxide of biscyclopentenyl ether having the formula <FORM:0812374/IV (b)/1> and its preparation by reacting bis-cyclopentenyl ether with an organic per-acid at a temperature below about 65 DEG  C., there being used at least 2 mols. of per-acid per mol. of the ether.  In an example, hydrogen chloride is reacted with cyclo pentadiene to form 3-chloro cyclo pentene which is reacted with dilute aqueous alkali (K2CO3) yielding 3-hydroxy cyclopentene which, if desired after isolation, is treated with a mineral acid catalyst, e.g. HCl, to form bis-cyclopentenyl ether from which the desired di-epoxide is obtained by treatment with 2.4 mols. of per-acetic acid containing a minor amount of sodium acetate, at 15-20 DEG  C.; pressures from slightly below to slightly above atmospheric may be used.  A small quantity of the mono-epoxidized ether is obtained which may be recycled to the epoxide reaction to form more di-epoxide.  The per-acetic acid may be replaced by per-benzoic or per-phthalic acid.  The isolation of the various intermediates is described.  The di-epoxides may be used to prepare polyether resins or in the stabilization of resins (see Group IV(a)).  They may also be used to stabilize unsaturated compounds present in perfumes, perfumed soaps, essential oils and cosmetics generally and insecticides containing chlorine (see Groups III and VI).ALSO:Perfumes and perfumed toilet articles such as creams, skin lotions, hair dressings are stabilized against degradation by incorporating therein the bis-cyclopentenyl ether diepoxide of the formula <FORM:0812374/VI/1> Insecticides containing chlorine such as endrin and dieldrin are also stabilized by the above diepoxide or a polymer thereof or a copolymer of the di-epoxide with another epoxy compound such as ethylene oxide, propylene oxide, butylene oxide, vinyl cyclo-hexene oxide, styrene oxide, allyl glycidyl ether or dicyclpentadiene epoxide.  The preparation of the diepoxide and its polymers and copolymers is described (see Groups IV (a) and IV (b)).