Room Temperature Cationic Polymerization of Epoxy Methyl Oleate with B(C6F5)3

We have found that B(C6F5)(3) in toluene can be an effective initiator for cationic polymerization of epoxidized fatty acid methyl esters and epoxidized oils with cis-disubstituted oxirane groups. The reaction is relatively fast, but controllable. The polymerization product of epoxy methyl oleate was a mixture of linear and cyclic oligomers of molar masses up to 27,000. MALDI-TOF analysis of oligomers of epoxidized methyl oleate revealed a clean pattern consistent with predominantly linear structures. The presence of hydroxyls from moisture, or resulting from epoxidation, seemed to initiate formation of linear polymers. A zwitterionic mechanism of polymerization was proposed. The process is suitable for fast conversion of epoxidized natural oils to useful epoxy resins.

Automated summary

Using B(C6F5)(3) in toluene as an initiator, cationic polymerization of epoxidized fatty acid methyl esters and epoxidized oils with cis-disubstituted oxirane groups can be effectively carried out. The polymerization product is a mixture of linear and cyclic oligomers, suitable for fast conversion of epoxidized natural oils into useful epoxy resins.