Epoxidized glycidyl esters of fatty acids (EGE) derived from soybean oil/linseed oil have been synthesized to have higher oxirane contents and enhanced reactivities compared to epoxidized soybean oil (ESO), epoxidized linseed oil (ELO) or epoxidized alkyl soyate (EAS). The thermoset polymers were fabricated through direct cationic curing of the epoxy monomers or by copolymerization with anhydride or polyamines. The curing behaviors of each system and glass transition temperatures (Tg) of the respective polymers were monitored by differential scanning calorimetry. The performance of the polymer products was further studied by measurements of thermal stability and mechanical properties. The results indicated that Tg and performance, i.e., reactivity and strength, of the vegetable oil derived epoxies were mostly a function of the respective oxirane contents.Performance was enhanced by presence of the glycidyl moiety versus only internal oxirane. In addition, the presence of pendant chain chemical structures or presence of saturated components tended to reduce performance. Therefore, EGE products displayed improved Tg and mechanical properties compared to their ESO or ELO counterparts or EAS. An added benefit is that the biorenewable EGEs have inherently low viscosity, are efficient solvents with regard to viscosity reduction and superior as a reactive diluent for commercial epoxy, the diglycidyl ether of bisphenol A (DGEBA). EGE could be advantageous for defect-free fabrication of complex, shaped epoxy composites for structural applications by modern resin infusion techniques.

Structure-property relationships of vegetable oil derived epoxy monomers and thermosetting polymers

245th National Meeting (2013)

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