Isoprene Soya Diels-Alder Adduct and Epoxidation for Photopolymerization

A novel cyclohexane derivatized soybean oil (CSO) is synthesized by Diels-Alder cycloaddition of soybean oil with isoprene. Then, the epoxidized cycloaliphatic soybean oil (ECSO) is prepared via epoxidation of CSO. For comparison purpose, norbornylized soybean oil (NSO) and epoxy norbornane soybean oil (ENSO) are synthesized. The CSO, ECSO, NSO, and ENSO are characterized by H-1 NMR, C-13 NMR, gradient heteronuclear single quantum correlation (gHSQC) 2D NMR, and mass spectroscopy. The epoxidized soybean oil (ESO), ECSO, and ENSO are photopolymerized using UV-light, and the kinetics of the photocuring reactions is evaluated by real-time Fourier transform infrared (FT-IR) and photo-differential scanning calorimetry (DSC). Real-time FT-IR and photo-DSC indicate the improved reactivity of ECSO and ENSO compared to ESO. It is found that the curing rate and final conversion of novel developed ECSO is higher than ESO, but lower than ENSO.

Automated summary

A novel cyclohexane derivatized soybean oil (CSO) was synthesized via Diels-Alder cycloaddition, and then epoxidized to form epoxidized cycloaliphatic soybean oil (ECSO). Compared to epoxidized soybean oil (ESO), ECSO and epoxy norbornane soybean oil (ENSO) exhibit improved reactivity. The curing rate and final conversion of ECSO are higher than ESO, but lower than ENSO.