Synthesis of multifunctional monomers from rosin for the properties enhancement of soybean-oil based thermosets

Abstract

Two kinds of rosin derivatives, (2-hydroxy-3-(methacryloyloxy)propyl 7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,4b,5,6,10,10a-decahydrophenanthrene-1-carboxylate) (HMPIDDC) and (((7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthren-1-yl)methyl)azanediyl)bis(2-hydroxypropane-3,1-diyl)bis(2-methylacrylate) (IDOMAHM) were synthesized under mild and easy to implement conditions. The two derivatives were employed as the rigid monomers to copolymerize with acrylated epoxidized soybean oil (AESO), as so to improve the performance of the cured resins. The chemical structures of HMPIDDC and IDOMAHM were confirmed by nuclear magnetic resonance (NMR) and Fourier Transform Infrared (FT-IR) before copolymerization. The curing behaviors of pristine AESO, AESO/HMPIDDC blend, and AESO/IDOMAHM blend were monitored by differential scanning calorimetry (DSC). Moreover, the thermal and mechanical properties of the cured resins were evaluated by universal mechanical testing, dynamic mechanical analysis (DMA) and thermogravimetric analysis (TGA). The results demonstrated that after the introduction of HMPIDDC and IDOMAHM, the glass transition temperature and mechanical properties of the copolymerized resin were significantly increased. In one word, HMPIDDC and IDOMAHM showed dramatic potential to be used as bio-based compounds to improve the properties of soybean-oil based thermosets.