Bio-Based Aromatic Epoxy Monomers for Thermoset Materials

Abstract

The synthesis of polymers from renewable resources is a burning issue that is actively investigated. Polyepoxide networks constitute a major class of thermosetting polymers and are extensively used as coatings, electronic materials, adhesives. Owing to their outstanding mechanical and electrical properties, chemical resistance, adhesion, and minimal shrinkage after curing, they are used in structural applications as well. Most of these thermosets are industrially manufactured from bisphenol A (BPA), a substance that was initially synthesized as a chemical estrogen. The awareness on BPA toxicity combined with the limited availability and volatile cost of fossil resources and the non-recyclability of thermosets implies necessary changes in the field of epoxy networks. Thus, substitution of BPA has witnessed an increasing number of studies both from the academic and industrial sides. This review proposes to give an overview of the reported aromatic multifunctional epoxide building blocks synthesized from biomass or from molecules that could be obtained from transformed biomass. After a reminder of the main glycidylation routes and mechanisms and the recent knowledge on BPA toxicity and legal issues, this review will provide a brief description of the main natural sources of aromatic molecules. The different epoxy prepolymers will then be organized from simple, mono-aromatic di-epoxy, to mono-aromatic poly-epoxy, to di-aromatic di-epoxy compounds, and finally to derivatives possessing numerous aromatic rings and epoxy groups.

En route to CO2-containing renewable materials: catalytic synthesis of polycarbonates and non-isocyanate polyhydroxyurethanes derived from cyclic carbonates

“…133 Any diol can be reacted with ECH to generate bis(epoxides) that can be converted to the corresponding COCs. 134 The diols can be derived from biomass sources (for example cellulose or lignin, see Fig. 8 for examples).…”

Protective role of luteolin against bisphenol A‐induced renal toxicity through suppressing oxidative stress, inflammation, and upregulating Nrf2/ARE/ HO‐1 pathway

“…BPA is a xenoestrogen, which mimics the action of regular estrogen and causes ominous health results. Besides its estrogenic activity, BPA appears to deregulate the cytokines and prompt OS in the cells of the brain, liver, and kidney .…”

Sustainable Alternative Composites Using Waste Vegetable Oil Based Resins

“…The use of these resins not only restricts the potential reductions in carbon footprint, but also presents challenges regarding eco-and human toxicity [10]. For example, diglycidyl ether of bisphenol A (DGEBA), a molecule predominantly used in the epoxy resin market, uses bisphenol A (BPA) as a precursor [11]. This molecule is a recognised teratogenic agent, endocrine disruptor, presents long lasting effects to aquatic life, and has been removed from polymers used in baby bottles [12][13][14].…”

“…This molecule is a recognised teratogenic agent, endocrine disruptor, presents long lasting effects to aquatic life, and has been removed from polymers used in baby bottles [12][13][14]. Specifically, bisphenol-based networks such as those formed with DGEBA can release BPA even after curing since these cross-linked units are susceptible to hydrolysis [11].…”