Biobased epoxy resin derived from eugenol with excellent integrated performance and high renewable carbon content

Abstract

Developing biobased epoxy resin with high renewable carbon content and outstanding integrated performance is beneficial for both sustainable development and applications in cutting-edge fields. Herein, a biobased epoxy monomer (TEUP-EP) with high renewable carbon content (100%) was synthesized from renewable eugenol with a sustainable process; TEUP-EP was then blended with 4,4 ′ -diaminodiphenylmethane (DDM) to develop a new biobased epoxy resin (TEUP-EP/DDM). The integrated performance of TEUP-EP/DDM resin was studied and compared with that of petroleum-based diglycidyl ether of bisphenol A (DGEBA)/DDM resin. Compared with DGEBA/DDM resin, TEUP-EP/DDM resin has much better integrated performance and not only exhibits a glass transition temperature about 26 ∘ C higher and a 24.4% or 57% increased flexural strength or modulus, but also shows outstanding flame retardancy. Specifically, the limiting oxygen index increases from 26.5% to 31.4% and the UL-94 grade improves from no rating to the V-0 level; moreover, the peak heat release rate and total heat release decreased by 63.1% and 57.4%, respectively. All these results fully prove that TEUP-EP/DDM is a novel biobased high performance epoxy resin. The mechanism behind these attractive integrated performances is discussed intensively.

New Epoxy Thermosets Derived from Clove Oil Prepared by Epoxy-Amine Curing

“…Liu et al [25] took advantage of the phenol group for connecting two eugenol moieties by reaction with 1,4-dibromobutane and further epoxidation of allyl groups to get a diepoxy monomer. In addition, a trimer from eugenol was synthesized by reacting it with phosphorous oxychloride followed by further epoxidation [26]. This tripoxy monomer was cured with 4,4'-diaminodiphenylmethane and the thermoset obtained was compared with the one obtained from DGEBA, reaching the eugenol derivative better performances.…”

Eugenol-based thermally stable thermosets by Alder-ene reaction: From synthesis to thermal degradation

“…In a previous study, we also showed that the use of a phosphorus containing monomer synthesized with three eugenol residues led to the enhancement of the stability of epoxy thermosets, [32] which has been confirmed in a following study investigating flame retardancy properties. [33] Moreover, it has been showed that the use of a phosphorus-containing allylated monomer can enhance the properties of BMI thermosets. [34] Recently, it has been shown that an eugenol-based phosphate is a suitable monomer for the synthesis of bismaleimide thermosets with flame retardant properties.…”

Tunable thermal, mechanical, and controlled-release properties of epoxy phenolic novolac resin microcapsules mediated by diamine crosslinkers

“…16 Currently, epoxy resins play an indispensable role in various elds, such as coatings, aerospace, adhesives, paints, and engineering plastics. [17][18][19] Up to now, there were few literatures relevant to the fabrication of microcapsules/microspheres using epoxy resins as shells. [20][21][22] Recently, we synthesized MCs with porous surface using epoxy resin and demonstrated that epoxy resin based MCs prepared with a high epoxy value tended to yield a higher crosslinking degree, less porosity and a better thermal stability.…”