High-performance bio-based bismaleimide resins using succinic acid and eugenol

Abstract

Biseugenyl succinate (BEUS) and bis(4-maleimidephenyl) succinate (BMIS) were synthesized by the reaction of succinic acid (SA) with eugenol and the reaction of succinyl chloride with 4-hydroxyphenylmaleimide, respectively. A gelled mixture of BEUS and BMIS at a molar ratio of 1/1, 1/2 or 1/3 at 200 °C was compression-molded at 230 °C for 1 h to produce a cured BEUS/BMIS product. The properties of BEUS/BMIS were compared with the properties of 2,2′-diallyl bisphenol A (DABA)/4,4′-bismaleimidediphenylmethane (BMIM) cured at 230 °C for 1 h. The Fourier Transform Infrared (FTIR) analysis of the cured materials revealed that chain polymerization of allyl and maleimide groups occurred to produce BEUS/BMIS, whereas a stepwise ene reaction and subsequent chain polymerization in addition to an etherification reaction occurred to produce DABA/BMIM. The cured BEUS/BMIS (1/2, 1/3) showed a higher glass transition temperature and greater tensile strength than the corresponding DABA/BMIM. Bio-based thermosetting resins, biseugenyl succinate (BEUS) and bis(4-maleimidephenyl) succinate (BMIS) were synthesized from succinic acid and eugenol. The BEUS/BMIS cured at 230 °C for 1 h showed a higher glass transition temperature and a greater tensile strength than 2,2′-diallyl bisphenol A (DABA)/4,4′-bismaleimidediphenylmethane (BMIM) cured under the same condition. The Fourier Transform Infrared (FTIR) analysis of the cured materials revealed that chain polymerization of allyl and maleimide groups occurred to produce BEUS/BMIS, whereas a stepwise ene reaction and subsequent chain polymerization in addition to an etherification reaction occurred to produce DABA/BMIM.