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Soybean Oil-Based Thermoset Films and Fibers with High Biobased Carbon Content via Thiol–Ene Photopolymerization
journal contribution
posted on 2018-05-21, 00:00 authored by Sung-Soo Kim, Heonjoo Ha, Christopher J. EllisonWhile a number of
vegetable oil derivatives have been integrated
with petroleum-based materials to prepare thermosetting polymers,
existing examples usually incorporate low total biorenewable content
into the final product. With the goal of generating thermosets with
high biorenewable content, two different soybean oil derivatives with
multifunctional thiol and acrylate groups were photocured via thiol–acrylate
photopolymerization. For this purpose, l-cysteine, a nonhazardous
amino acid, was coupled with epoxidized soybean oil to synthesize
a mercaptanized soybean oil derivative containing multiple thiol groups.
After being mixed with acrylate counterparts suitable for performing
thiol–ene photopolymerizations, these monomer mixtures were
processed into thermoset films (via monomer mixture film casting followed
by photopolymerization) and fibers (via simultaneous electrospinning
of the monomer mixture and photopolymerization in flight). The resulting
materials possessed high biobased carbon content (BCC; over 90%) and
higher elasticity than cross-linked acrylated epoxidized soybean oil
without the thiol-containing component. This can be attributed to
a change in the cross-link density that is controlled by different
photopolymerization mechanisms (e.g., step-growth polymerization vs
chain-growth homopolymerization). We anticipate that the approaches
outlined in this study could be generalized to other bioderived triglyceride
oils for increasing the BCC and imparting biodegradability in a number
of materials applications.
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bioderived triglyceride oilsbiorenewable contentmaterialcross-linked acrylated epoxidized soybean oilmonomer mixture filmSoybean Oil-Based Thermoset Filmsthiolepoxidized soybean oilBCCmercaptanized soybean oilsoybean oil derivativesHigh Biobased Carbonvegetable oil derivativesphotopolymerizationbiobased carbon content
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