Polymerization reactions of epoxidized soybean oil and maleate esters of oil-soluble resoles

ABSTRACT In this study, the polymerization reactions of epoxidized soybean oil (ESO) with the maleate half‐esters of oil‐soluble resoles and the properties of the final products were demonstrated. The maleate half‐esters of the dimeric oil‐soluble resoles were obtained by the esterification reaction of maleic anhydride with a p‐tertiary butyl phenol (p‐TBP) resole and p‐nonyl phenol resole resins in the first step. The monomers were characterized by IR and 1H‐NMR techniques. Then, the oil‐soluble resole maleates were polymerized with ESO to obtain tough and load‐bearing thermoset materials. The thermal and mechanical properties of the materials were determined by dynamic mechanical analysis, differential scanning calorimetry, thermogravimetric analysis, and tensile strength testing. The tensile strengths and storage moduli of the crosslinked polymers varied between 0.17 and 13 MPa and 10 and 1088 MPa, respectively. The elongation percentages of the materials were between 1 and 128%. The thermal resistance of the thermosets was measured as the 5% weight loss temperature. The reaction product of the ESO and maleate ester of p‐TBP showed the highest 5% weight loss at 247°C. © 2014 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2015, 132, 41457.