Isoprene Soya Diels–Alder Adduct and Epoxidation for Photopolymerization

Abstract

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 by1H NMR,13C 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.

Cationic Copolymers of Norbornylized Seed Oils for Fiber-Reinforced Composite Applications

“…Nobornylization of linseed oil and soybean oil has been previously reported by Soucek and co-workers. 18 , 38 , 39 , 42 , 43 , 81 , 82 However, nobornylization of the genetically modified soybean oil, commonly known as the HOSO, is reported here for the first time (27% norbornylization). The investigation of norbornylization of seed oils having different major fatty acid constituents (oleic, linoleic, and linolenic fatty acids) was carried out.…”

“… 16 , 17 Even though soybeans are among the most common food crops in America, its easy availability and low cost have enabled its market expansion to coatings, plastics, and tire industries. 18 − 23 High oleic soybean oil (HOSO) is yet another new and dynamic category of soybean oil that are essentially replacing partially hydrogenated oils, in various food and even nonfood industrial applications. 24 It is a genetically modified variant of soybean, finding its niche potential in industrial application like coatings, copolymers, asphalt plasticizer, and so forth.…”

Sustainable Thermosets and Composites Based on the Epoxides of Norbornylized Seed Oils and Biomass Fillers

“…It can be due to the steric hindrance factor, playing the most important role during epoxidation. Lesser steric hindrance proved to be favorable for the epoxidation reaction than a higher ring strain energy moiety (norbornylized seed oil has higher ring strain energy due to the presence of norbornene moieties 19 ). The presence of norbornene groups only increases the steric hindrance in the moieties and leads to lower epoxidation.…”

“…A slightly modified procedure from the previous work by Soucek and co-workers 79 was used for the epoxidation of norbornylized seed oils. 27 It included three stages: nobornylization of seed oils, preparation of the epoxidation catalyst, followed by the subsequent epoxidation.…”

“…It has been reported to find their use in various applications such as in the coating and elastomer industries. 19 epoxidation agents such as peracids, dioxirane, and hydrogen peroxide were used by various researchers. 20,23,24 As reported in the previous work by Soucek and co-workers, 25 the hydrogen peroxide route, with the polyoxometalate quaternary ammonium tetrakis-diperoxotungsto phosphate (3−) as the epoxidation catalyst 26 (phase-transfer catalyst), was proved to be the most favorable route.…”