Synthesis of renewable isosorbide-based monomer and preparation of the corresponding thermosets

Two kinds of difunctionalized isosorbide derivatives containing norbornene groups were designed and synthesized by a facile one-step reaction under mild conditions. 1H NMR spectroscopy confirmed the chemical composition and differential scanning calorimetry (DSC) revealed the distinct curing behaviors between conventional petroleum-based dicyclopentadiene (DCPD) and synthesized renewable isosorbided-based monomer (ISN). In contrast to DCPD, ISN was low viscous liquid at room temperature and had even higher reactivity to perform ring-opening metathesis polymerization (ROMP) in the presence of Grubbs’ catalyst. Due to the presence of flexible and elastic SiC long chains, the cured poly(ISN) thermosets not only had good mechanical properties but also exhibited much higher storage modulus at the rubbery state in comparison with traditional poly(DCPD).

A novel norbornenyl-functionalized isosorbide monomer (ISN) was synthesized via a facile one-step reaction under mild conditions and then ring-opening metathesis polymerization (ROMP) was conducted to prepare corresponding thermosets. Due to the presence of flexible and elastic SiC long chains and rigid two-fused ring of isosorbide, the cured poly(ISN) not only had good mechanical properties and but also exhibited much higher storage modulus than poly(DCPD) at the rubbery state.Figure optionsDownload as PowerPoint slide