ADDITION-REACTION OF EPOXY COMPOUNDS WITH ESTERS AND ITS APPLICATION FOR POLYMER SYNTHESES

Regioselective addition reaction of epoxy compounds with esters was investigated using low molecular weight tert-amines, quaternary onium salts, complexes of crown ethers-metal salts, or insolublized poly (styrene) beads containing pendant amine, quaternary onium salt, or crown ether moieties, as catalysts. Although the reaction proceeded smoothly under relatively mild reaction conditions to give the corresponding adducts with high yields, the rate of addition reaction and the yield of product were strongly affected by the kind of catalyst. Poly-addition reaction of di-epoxy compounds with di-esters proceeded to give the corresponding polyesters in the presence of various quaternary onium salts. Addition reaction of poly (glycidyl methacrylate) (PGMA) with some esters such as S-phenylthio benzoate and p-nitorophenyl cinnamate proceeded with high efficiency to give the corresponding polymers. Insertion reaction of epoxy compounds into phenyl ester linkage of polymer chains was also achieved using those catalysts. Thermal crosslinking reaction of epoxy resins using poly-functional phenyl esters or thioesters proceeded to give gel products as well as the reaction of PGMA with poly-functional esters or the reaction of poly (phenyl methacrylate)s with poly-functional epoxy compounds using quaternary onium salts or crown ether complexes.