Synthesis and Preparation of Bio-Based ROMP Thermosets from Functionalized Renewable Isosorbide Derivative

One novel monomer based on renewable isosorbide, isosorbide silicon norbornene (ISN), is synthesized and a series of bio-based thermosets is prepared via ring-opening metathesis polymerization (ROMP) of ISN in place of partial dicyclopentadiene (DCPD) in the presence of Grubbs' catalyst. ¹H and ¹³C NMR spectroscopy and nonisothermal differential scanning calorimetry (DSC) have been implemented to confirm the chemical composition of ISN and examine the curing behaviors of ISN/DCPD comonomers, respectively. Compared to DCPD, ISN is found to exhibit higher reactivity that allows facile lower temperature ROMP making it an ideal candidate for bio-based self-healing applications. The effect of incorporation of ISN on the thermal and mechanical properties of cured poly(ISN/DCPD) thermosets is also evaluated by dynamic mechanical analysis, thermogravimetric analysis, thermal mechanical analysis, and universal tensile test. The poly(ISN/DCPD) thermosets display good thermal/mechanical properties due to the introduction of less rigid ISN moieties and higher cross-linking density of the material.