Patent GB-786116-A (GB)
Title: A process for preparing epoxidized condensation polymers and the resulting products
IPC: C08G59/34
Filed: 1955-09-01
Abstract: An epoxidized condensation polymer is made from a condensation polymer containing a plurality of non-terminal ethylenically or acetylenically unsaturated linkages and containing in a polymer chain, in addition to carbon, at least one of the following elements: oxygen, nitrogen, silicon, phosphorus and sulphur, by reacting the condensation polymer with an epoxidizing agent in an amount to convert at least two of the unsaturated linkages per molecule to epoxy groups.  The unsaturated condensation polymer may be (a) a polyester obtained by reacting a polyhydric alcohol, a polycarboxylic acid and, if desired, a modifying agent in which at least one of the reactants is unsaturated; (b) a polymerization product of the above unsaturated alkyd with pentadiene or butadiene; (c) a polyester obtained by polymerizing an unsaturated hydroxy acid; (d) a polythioester obtained by reacting an unsaturated polymercaptan with a polycarboxylic acid or acid halide; (e) a polyamide obtained by reacting a polycarboxylic acid with a polyamine in which one or both reactants is unsaturated and which may be further reacted with a monoamine, acetic anhydride, ketene, ethylene oxide or allyl glycidyl ether; (f) a polyamide obtained by polymerizing an unsaturated aminocarboxylic acid; (g) a polyesteramide obtained by reacting a polycarboxylic acid with an amino alcohol in which one or both reactants is unsaturated; (h) a polycarbamate obtained by reacting a polyhydric alcohol with a polyisocyanate or a polyamine with a bischloroformate, either or both of the reactants being unsaturated; (i) a polysulphide obtained by reacting sodium sulphide with an unsaturated organic dihalide or by reacting an unsaturated polymercaptan with an organic dihalide; (j) a solicon-containing polymer obtained by reacting a silicon-containing polycarboxylic acid with an unsaturated polyhydric alcohol or an unsaturated polyamine; (k) a silicon-containing polymer obtained by reacting an unsaturated polycarboxylic acid with a silane-polyhydric alcohol reaction product as described in U.S.A. Specification 2,628,215; (1) a phosphorus-containing polymer obtained by reacting a phosphorus-containing polybasic acid with an unsaturated polyhydric alcohol or unsaturated polyimine or by reacting an unsaturated phosphorus-containing acid with a polyhydric alcohol.  A large number of reactants are specified for making the polycondensates (a)-(1) above, those used in making the polyesters, polyesteramides or polyamides may contain sulphur linkages.  Epoxidation of the unsaturated condensation polymers may be effected with performic, peracetic, perbenzoic or monoperphthalic acid at -20 DEG  C. to 80 DEG  C.  The epoxidized polymers may be cured with an epoxy curing agent (e.g. a polybasic acid, polyamine, polymercaptan, Friedel-Crafts catalyst, dialdehyde or amine- or amide-aldehyde resins).  They may be used as adhesives, preferably with a diluent (e.g. benzene, toluene, xylene, propionitrile, crotonitrile or benzonitrile) or in the preparation of patting or coating compositions.  The epoxidized polymers may be used in combination with other epoxy-containing materials, e.g. epichlorhydrin, glycidol, butadiene monoxide, diglycidyl ether, allyl glycidyl ether, glycidyl ethers of polyhydric phenols or polyhydric alcohols and diglycidyl esters of dicarboxylic acids.  They may be hydrated to form glycols, may be reacted with monoamines or may be reacted with monocarboxylic acids (including oil and resin acids) to produce derivatives valuable as plasticizers, lubricating oils and drying oils. Examples describe the epoxidation of the following condensation polymers: (1) a polyester from dimerized linoleic acid and ethylene glycol; (2) a polyester from 2-butenediol-1.4 and adipic acid; (3) a polyamide from fumaric acid and decamethylene diamine; (4) a polycarbamate from tetramethylene diamine and 2-butenediol-1.4 bis chloroformate; (5) a polycarbamate from 2-butenediol-1.4 and benzene diisocyanate; (6) a polyester from 4.41-thiodibutanol and maleic acid; (7) a polymer from dicarboxyphenyldimethylsilane and 2-butenediol-1.4; (8) a polymer from benzenephosphonic acid and cyclohexenediol-1.4.  The epoxidized polyester of Example (1) or the epoxidized silicon-containing polymer of Example (7) was mixed with 2,2-bis (2,3-epoxypropoxyphenyl) propane and a little 2.4.6-tri (dimethylaminomethyl) phenol and the mixture heated to form a casting.  The epoxidized polyamide of Example (3) or the epoxidized polycarbamate of Examples (4) or (5) was mixed with 2.2-bis (2,3-epoxypropoxyphenyl) propane and the mixture diluted with acetonitrile to form an adhesive.  The invention of Specification 744,831 is disclaimed.  Specification 701,238 also is referred to.