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Diastereoisomeric diversity dictates reactivity of epoxy groups in limonene dioxide polymerization

: Soto, M.; Koschek, Katharina

Fulltext ()

eXPRESS polymer letters 12 (2018), No.6, pp.583-589
ISSN: 1788-618X
Journal Article, Electronic Publication
Fraunhofer IFAM ()
biopolymers; thermal property; thermosetting resin

Limonene dioxide (LDO) has the potential to find a wide application as a bio-based epoxy resin. Its polymerizations by catalyzed ring-opening, and by poly addition with diamines were compared with the polymerizations of the commercial epoxy resins bisphenol-A diglycidyl ether (BADGE), and 3,4-epoxycyclohexylmethyl-3′,4′-epoxycyclohexane carboxylate(ECC). Differential scanning calorimetry (DSC) studies showed that LDO polymerizations suffer in all cases studied from incomplete conversions. Nuclear magnetic resonance (NMR) studies revealed that in cis-isomers of LDO the internal epoxide rings were not reacting. The low reactivity of this epoxide group was explained by mechanistic considerations making use of the Fürst-Plattner rule, or trans-diaxial effect. Due to diastereomeric diversity approximately one-fourth of epoxide groups present in LDO could not react. Therefore, a diastereo selective epoxidation of limonene could provide a fully reactive bio-based epoxy resin.