Eugenol, a Promising Building Block for Biobased Polymers with Cutting-Edge Properties

Morales‐Cerrada, Roberto; Molina‐Gutiérrez, Samantha; Lacroix‐Desmazes, Patrick; Caillol, Sylvain

doi:10.1021/acs.biomac.1c00837

Cited by 54 publications

(34 citation statements)

References 212 publications

(459 reference statements)

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“…It is believed that by using appropriate eugenolbased monomers, the transition from a linear to circular chemistry and thus a circular (bio)economy will be easier and more adaptable, which would minimize waste and reduce demands on finite raw materials and input of lignocellulosic feedstock in future biorefineries. Certainly, the exceptional structural versatility of eugenol molecules 176,177 will continue to inspire the development of methods for preparing new monomers and thus new, more effective thermosets in an economical and sustainable manner.…”

Section: Discussionmentioning

confidence: 99%

Synthesis of eugenol‐based monomers for sustainable epoxy thermoplastic polymers

Kouznetsov

Méndez

2022

J of Applied Polymer Sci

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New developments in thermosets based on bioproducts are gaining significance due to the importance of replacing thermosets and their monomers, traditionally obtained from petrochemical processes, with biobased thermosets prepared from biomass. In the context of new BPA/DGEBA replacements with both enhanced performance and reduced toxicity and the development of innovative biobased thermosetting resins, the conversion of plant biomass, especially natural phenols, into useful polymeric materials is believed to have considerable environmental and economic value. Eugenols are receiving encouraging interest, not only due to their sourcing but also due to their structure and chemical properties, which could enhance the physical characteristics of thermosetting materials, and which could reduce their toxic effects on the environment and human health. The present review mainly focuses on the utilization of eugenol for the synthesis of biobased epoxy and its thermosetting resins, describing synthetic details of new designs for eugenol-based monomer and/or additive component preparation that are conducive to the formation of eugenol-containing polymeric materials. Synthetic methods for eugenol-based monomers are classified according to the principles of green chemistry and are divided into three large groups: single reactions, consecutive reactions, and multicomponent reactions. Outstanding physical characteristics of the formulated eugenol-based thermosetting epoxy materials are also described.

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Section: Discussionmentioning

confidence: 99%

Synthesis of eugenol‐based monomers for sustainable epoxy thermoplastic polymers

Kouznetsov

Méndez

2022

J of Applied Polymer Sci

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“…124,125 Eugenol is commonly used in perfumes, antioxidants, food, and taste additives and also can be a representative high-value renewable biomass material. 126 Eugenol, as renewable feedstock, has a distinctive molecular structure, containing both allyl and phenolic hydroxyl groups, which means that it can be used as a monomer for a bio-based polymer to replace petroleumbased polymers 127 and possesses multifunctionality such as antimicrobial activity, 128 mechanical strength and flame retardant properties. 129…”

Section: Eugenol-based Polymersmentioning

confidence: 99%

Bio‐renewable polymers based on lignin‐derived phenol monomers: Synthesis, applications, and perspectives

Yang

Ding

Puglia

et al. 2022

SusMat

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In recent decades, the continuous depletion of fossil fuels and the increasingly serious environmental issue have aroused wide attention on the development of biopolymers based on renewable biomass. Lignin is the second most abundant organic bio‐based macromolecule second to cellulose, and it can be widely found in plants. Furthermore, various phenol derivatives can be obtained by their depolymerization processes. The development of bio‐renewable polymeric materials originating from lignin‐derivative phenol monomers, such as vanillin, syringaldehyde, eugenol, vanillyl alcohol, vanillic acid, and ferulic acid, will not only valorize the bio‐sourced materials but also effectively reduce petroleum resource consumption and mitigate the environmental pollution. Therefore, an updated overview of the synthesis processes of these bio‐based polymers developed in the past decade, which includes both thermosets and thermoplastics such as epoxy, phenolic, polyimine, polybenzoxazine, polyurethane, and polyesters, are elucidated. In addition, the applications of these bio‐based polymers and their composites in flame‐retarded materials, degradable and reprocessable materials, dielectric materials, optoelectronic materials, as well as smart responsive materials are also intensively discussed. In line with the gradual development of synthesis technologies, we believe that derivatives of lignin will turn into one of the most promising materials to be considered for the preparation of high‐performance and functional bio‐based polymer materials.

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“…[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.…”

Section: Doi: 101002/mame202100833mentioning

confidence: 99%

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

Zhang

Zhai

et al. 2021

Macro Materials & Eng

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Eugenol-based epoxy monomer (Eu-EP) is prepared here, followed by curing with a novel eugenol-derived diamine (Eu-DA) curing agent for fully eugenol-based epoxy thermosets. The cure behavior, thermal stability, mechanical properties, and thermomechanical properties of these eugenol-based epoxy resins are investigated and compared with a partially biobased epoxy thermoset prepared from diglycidyl ether of bisphenol A (DGEBA) and Eu-DA. Both epoxy materials exhibit storage moduli higher than 2.1 GPa at room temperature. The tensile strength of Eu-EP/Eu-DA (21.9 MPa) is comparable to that of the DGEBA/Eu-DA (24.3 MPa) thermosets and the epoxy thermoset cured from DGEBA and Eu-DA shows a higher glass transition temperature than those from Eu-EP and Eu-DA. The synthesis strategy of Eu-DA and Eu-EP shows great potential to be applied in other biobased building blocks with hydroxyl groups. Overall, eugenol is a renewable resource to develop high value-added chemicals and sustainable polymers with comparable properties to petroleum-based counterparts.

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Eugenol, a Promising Building Block for Biobased Polymers with Cutting-Edge Properties

Cited by 54 publications

References 212 publications

Synthesis of eugenol‐based monomers for sustainable epoxy thermoplastic polymers

Synthesis of eugenol‐based monomers for sustainable epoxy thermoplastic polymers

Bio‐renewable polymers based on lignin‐derived phenol monomers: Synthesis, applications, and perspectives

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

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