Diastereoisomeric diversity dictates reactivity of epoxy groups in limonene dioxide polymerization

eXPRESS Polymer Letters

M. Soto¹ 

关键词: biopolymers;    thermosetting resins;    thermal properties;   

DOI  :  10.3144/expresspolymlett.2018.48

学科分类：生物科学（综合）

来源: eXPRESS Polymer Letters

【 摘 要 】

Limonene dioxide (LDO) has the potential to find a wide application as a bio-based epoxy resin. Its polymerizationsby catalyzed ring-opening, and by polyaddition with diamines were compared with the polymerizations of the commercialepoxy 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 studiedfrom incomplete conversions. Nuclear magnetic resonance (NMR) studies revealed that in cis-isomers of LDO the internalepoxide rings were not reacting. The low reactivity of this epoxide group was explained by mechanistic considerationsmaking use of the Fürst-Plattner rule, or trans-diaxial effect. Due to diastereomeric diversity approximately one-fourth ofepoxide groups present in LDO could not react. Therefore, a diastereoselective epoxidation of limonene could provide afully reactive bio-based epoxy resin.

【 授权许可】

CC BY