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Limonene-Based Epoxy: Anhydride Thermoset Reaction Study

Institut Charles Gerhardt Montpellier-UMR 5253-CNRS, Université Montpellier, ENSCM–240 Avenue Emile Jeanbrau, CEDEX 5, 34296 Montpellier, France
Author to whom correspondence should be addressed.
Molecules 2018, 23(11), 2739;
Received: 27 September 2018 / Revised: 10 October 2018 / Accepted: 22 October 2018 / Published: 23 October 2018
(This article belongs to the Special Issue Natural Polymers and Biopolymers)
PDF [3609 KB, uploaded 29 October 2018]


The development of epoxy thermosets from renewable resources is of paramount importance in a sustainable development context. In this paper, a novel bio-based epoxy monomer derived from limonene was synthesized without epichlorohydrine and characterized. In fact, this paper depicts the synthesis of bis-limonene oxide (bis-LO). However, intern epoxy rings generally exhibit a poor reactivity and allow reaction with anhydride. Therefore, we used a reaction model with hexahydro-4-methylphthalic anhydride to compare reactivity of terminal and interepoxy functions. We also studied the influence of methyl group on intern epoxy functions. Furthermore, the influence of epoxy:anhydride stoichiometry and initiator amount was studied. These studies allow to propose an optimized formulation of bis-LO. Finally, a bis-LO-based thermoset was obtained and characterized. View Full-Text
Keywords: limonene; biobased polymers; anhydride; epoxy; DSC limonene; biobased polymers; anhydride; epoxy; DSC

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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Couture, G.; Granado, L.; Fanget, F.; Boutevin, B.; Caillol, S. Limonene-Based Epoxy: Anhydride Thermoset Reaction Study. Molecules 2018, 23, 2739.

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