Eugenol, a developing asset in biobased epoxy resins

Abstract

bisphenol A (BPA), bisphenol F (BPF), metachloroperbenzoïc acid (m-CPBA), Steric exclusion chromatography (SEC), nuclear magnetic resonance (NMR), Dichloromethane (DCM), Acetic anhydride (Ac2O)Mono glycidyl silyl etherated eugenol (GSE), diglycidylether of bisphenol A (DGEBA), hexahydrophtalic anhydride (HHPA), Methylhexahydrophthalic anhydride (MHHPA),2,4,6tris(diMethylaminomethyl)phenol (DMP), diglycidylether diphenolates n-pentyle (DGEDP-Pe), eugenol mono-glycidyl ether (GE), 2-ethyl-4methylimidazole (EMID), diepoxidized isoeugenol (Iso-eug), diepoxidized eugenol (Eug), maleopimaric acid (MPA), isophoronediamine (IPDA), diglycidyl benzyl bis-eugenol (DEU-EP), diglycidyl butyl bis-eugenol (Eu-EP), 3,3'-Diaminodiphenylsulfone (33DDS), N,N-Dimethylacetamide (DMAc), N,N-diméthylpyridin-4-amine (DMAP), 4,4′-methylenedianiline (DDM), m-xylylenediamine (MXDA), hexachlorocyclotriphosphazene (HCP), Matrix Assisted Laser Desorption Ionisation/Time Of Flight (Maldi-TOF), hexachlorocyclotriphosphazene (HCP).

Synthesis of a Curing Agent Derived from Limonene and the Study of Its Performance to Polymerize a Biobased Epoxy Resin Using the Epoxy/Thiol-Ene Photopolymerization Technique

“…Within the area of thermoset polymers, one of the priorities is the investigation of novel biobased epoxy monomers as well as new curing agents [ 4 , 5 , 6 ]. Some biobased thermosetting polyethers depict similar or superior properties to the polymers derived from the commercial epoxy resin diglycidyl ether of bisphenol A, which has the highest cost-benefit ratio in the global market [ 7 , 8 , 9 , 10 , 11 , 12 , 13 ]. The synthesis of novel biomass-derived curing agents for epoxy resins has also been studied and documented [ 14 , 15 , 16 , 17 , 18 ].…”

Fully Eugenol‐Based Epoxy Thermosets: Synthesis, Curing, and Properties

“…[11] Increasing environmental concerns, strict safety regulations, and scarcity of nonrenewable petroleum-based resources have driven researchers in academia and manufacturing to develop sustainable epoxy thermosetting materials. [12][13][14][15][16][17] Numerous biobased building blocks have been applied to develop bioderived epoxy polymers. Vegetable oils (such as soybean oil and castor oil) with nonconjugated double bonds have been employed to develop epoxy monomers or oligomeric epoxidized vegetable oils through the epoxidation of their carbon-carbon double bonds.…”

Synthesis of eugenol‐based monomers for sustainable epoxy thermoplastic polymers

“…Showing reduced toxicity and reduced production costs, some bioderived materials look very attractive as sustainable alternative precursors for the preparation of monomers and polymers. [9][10][11][12] Among them, natural phenols, such as lignocellulosic derivatives (i.e., vanillin (4), [13][14][15] ferulic acid (5), 16 and guaiacol (6) 17 ), the 3-alkenyl phenolic molecule cardanol (7), [18][19][20] anethole (8), 21 or (iso)eugenols (9)(10), the main monolignol constituents of clove oil 22 and other similar phenolic molecules (Figure 1b) are all being considered as sustainable alternatives and potential molecular replacements for BPA and DGEBA in epoxy resin 11 manufacturing.…”

“…It is worth noting that the expansive literature on the diverse chemical, pharmacological, and medical aspects of eugenol and clove oil have been periodically reviewed, [34][35][36] but research on the preparation of epoxy and thermosets and other materials from eugenol platform chemicals is much less discussed from the point of view of the synthesis of monomers based on eugenol molecules. 22 Consequently, enhancing and focusing on this theme will be timely, very useful, and important for the sustainable development of the field.…”