New monomers or co-monomers based on the alkoxyfuranone Scaffold: Toward new alternatives to Petroleum-Based structures

• Published in: European polymer journal Vol. 215; p. 113259
• Main Authors: Le Dot, Marie, Andrés Gomez Fernandez, Mario, Langovist, Anne, Charrière, Bruno, Gérard, Pierre, Dumur, Frédéric, Hoffmann, Norbert, Lalevée, Jacques
• Format: Journal Article
• Language: English
• Published: Elsevier Ltd 17-07-2024; Elsevier
• Subjects: Chemical Sciences; Polymers; copolymerization; high-T$_g$ bio-based polymers; Alkoxyfuranones; Elium; bio-based monomers
• ISSN: 0014-3057; 1873-1945
• DOI: 10.1016/j.eurpolymj.2024.113259

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•A series of alkoxyfuranones derived from furfural have been synthesized.•The four alkoxyfuranones were studied as potential monomers or co-monomers.•The homopolymerization of two of them was successfully achieved.•High-glass transition temperature (Tg) bio-based polymer can be obtained.
Over the past decade, the circular economy has become a key component of sustainability due to environmental issues and more stringent environmental regulations. In this connection, the valuation of bio-based monomers possessing innovative structures remains an important challenge. Furthermore, several goals must be achieved: 1) the homopolymerization of such bio-based monomers by free radical photopolymerization which requires small energy inputs with limited emission of volatile organic compounds (COV) and 2) their copolymerization with Elium® thermoplastic resins to increase biogenic carbon in these novel low-viscosity methacrylic resins developed by Arkema. The challenge will be, in this context, to maximize the biomass carbon content while maintaining or even surpassing the properties exhibited by their petrochemical counterpart. In this work, a series of alkoxyfuranones derived from furfural have been synthesized. The four alkoxyfuranones (AF1, AF2, AF3 and AF4) varying by the functionality of the side chains (but-3-en-1-yl, acrylate, isopropyl and ethyl) attached via acetalization of the 5-hydroxy-2(5H)-furanone were studied as potential monomers or co-monomers for free radical polymerization. The synthesis of AF1 and AF2 has never been reported in the literature. The homopolymerization of two of them (AF1 and AF2) was successfully achieved, but only one led to a high-glass transition temperature (Tg) bio-based polymer. On the other hand, copolymerization with Elium® thermoplastic resins was obtained with different ratios of AF2 as a co-monomer. As a result, the expected gain value, such as faster photopolymerization was successfully obtained. Nevertheless, the copolymerization doesn’t lead to obtaining high-Tg polymers.