High performance, recyclable and sustainable by design natural polyphenol-based epoxy polyester thermosets

Renewable flavonoid and phlorotannin extracts were used as building blocks to synthesize biobased tris-epoxy monomers and further to design and develop sustainable thermosetting resins. The triglycidyl ethers of phloroglucinol and naringenin were combined and crosslinked with a series of anhydrides,...

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Bibliographic Details
Published in:Green chemistry : an international journal and green chemistry resource : GC 2023-03, Vol.25 (6), p.2327-2337
Main Authors: Dinu, Roxana, Pidvoronia, Anastasiia, Lafont, Ugo, Damiano, Olivier, Mija, Alice
Format: Article
Language:English
Subjects:
Anhydrides
Chemical bonds
Crosslinking
Epoxy resins
Ethers
Flavonoids
Glass transition
Green chemistry
Heat resistant materials
Mechanical properties
Modulus of elasticity
Monomers
Naringenin
Petroleum industry
Phloroglucinol
Sustainability
Thermosetting resins
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Summary:Renewable flavonoid and phlorotannin extracts were used as building blocks to synthesize biobased tris-epoxy monomers and further to design and develop sustainable thermosetting resins. The triglycidyl ethers of phloroglucinol and naringenin were combined and crosslinked with a series of anhydrides, four of them being bio-based. The thermosetting resins' reactivity has been studied, as well as the influence of the chemical structure of anhydride crosslinkers allowing us to obtain highly crosslinked networks with high performance. The designed thermosets show high glass transition values (134-199 °C), high storage moduli at 25 °C (2.7-3.5 GPa), and high crosslinking densities and gel content (>99%). These polyaromatic thermosets are characterized by high mechanical strength and toughness (Young's moduli ∼1.26-1.68 GPa), and they proved to be high heat-resistant materials (LOI ∼28-33%). The sustainability aspect could be related to a particularly important feature of these thermosets, their ability to be chemically recycled by bond exchange reactions. Therefore, the polyaromatic thermosets developed in this study demonstrate important characteristics recommending them as environmentally friendly alternatives to petroleum-based epoxy resins used in various industries such as civil, automotive, marine, aerospace, and space. Development of high-performance materials with a high content of aromatic units and high functionality, using natural and renewable polyphenolic synthons such as naringenin and phloroglucinol.
ISSN:1463-9262
1463-9270
DOI:10.1039/d2gc04414e