Sustainable Epoxy Vitrimers from Epoxidized Soybean Oil and Vanillin

Abstract

Epoxidized soybean oil (ESO)-derived epoxy thermosets are usually limited by their poor mechanical properties and non-reprocessability. Herein, we report sustainable epoxy vitrimers synthesized facilely by curing ESO with vanillin-derived Schiff base (VSB) dynamic hardener with 1,2-dimethylimidazole as an accelerator. The phenolic hydroxyl of VSB showed high reactivity toward the epoxy group of ESO with a curing activation energy of 108.9 kJ•mol −1 . The network rigidness and cross-link density of the epoxy vitrimers are adjustable by simply changing the feed ratio of flexible ESO and rigid VSB, which enables us to tailor the mechanical properties of the vitrimers easily over a wide range from soft to tough and hard. The dynamic Schiff base bonds provide the epoxy vitrimer with excellent reprocessability, weldability, reconfigurability, and programmability, which facilitates the recycling and processing of the cured epoxy materials. With tunable mechanical properties, reprocessability, and multifunctionality, the ESO-derived epoxy vitrimers are of great potential as alternatives to traditional epoxy thermosets.

Biobased High-Performance Epoxy Vitrimer with UV Shielding for Recyclable Carbon Fiber Reinforced Composites

“…However, these fabrication procedures usually require multiple steps accompanied by complicated and lengthy processes, and also unsatisfactory yields in some steps, which makes the final composites less cost-effective and unattractive for industrial applications. Recently, some efforts have been paid to simplify the fabrication procedures of biobased epoxy vitrimers by curing commercially available biobased epoxy resins (such as epoxidized soybean oils) with dynamic covalent bond containing hardeners. − However, these biobased epoxy vitrimers generally show poor mechanical properties and are not qualified as matrix for composites. Therefore, the development of biobased, high-performance, and cost-effective epoxy vitrimers is still a challenge for preparation of sustainable, recyclable, and competitive carbon fiber reinforced composites.…”

Biobased Dynamic Polymer Networks with Rapid Stress Relaxation

“…With the rapid growth of population and huge use of resources to generate nonrenewable materials, fossil resources face serious depletion. Consequently, numerous sustainable, nontoxic, biobased resources have been used as alternatives to petroleum-based feedstocks, including, for example, epoxidized soybean oil (ESO), natural rubber, lignin, vanillin, and chitosan . As a low-cost, abundant biomass resource, ESO has several advantages and has attracted significant attention in the academic and industrial sectors. − For example, Hu et al prepared a completely biobased DPN by cross-linking ESO with glycyrrhizic acid.…”

Catalyst‐free reprocessable crosslinked biobased polybenzoxazine‐polyurethane based on dynamic carbamate chemistry

“…Nowadays, the number of renewable or sustainable phenolic or amine derivatives to replace the petroleum-based ones as well as the development of environmentally compatible and sustainable polymers have attracted considerable attention. In recent years, a large number of renewable phenol derivatives such as cardanol, 5,6 vanillin, 7,8 eugenol, [9][10][11] chavicol, 12 guaiacol, 13 sesamol, 14 umbelliferone, 15 arbutin, 16 urushiol, 17 catechol, 18 para-coumaric acid, 19 tyrosol, 20 and so forth have been chosen as the naturally occurring materials for benzoxazine precursors synthesis.…”