title: Synthesis, Characterization, and Cross-Linking Strategy of a Quercetin-Based Epoxidized Monomer as a Naturally-Derived Replacement for BPA in Epoxy Resins.
abstract: The natural polyphenolic compound quercetin was functionalized and cross-linked to afford a robust epoxy network. Quercetin was selectively methylated and functionalized with glycidyl ether moieties using a microwave-assisted reaction on a gram scale to afford the desired monomer (Q). This quercetin-derived monomer was treated with nadic methyl anhydride (NMA) to obtain a cross-linked network (Q-NMA). The thermal and mechanical properties of this naturally derived network were compared to those of a conventional diglycidyl ether bisphenol A-derived counterpart (DGEBA-NMA). Q-NMA had similar thermal properties [i.e., glass transition (Tg ) and decomposition (Td ) temperatures] and comparable mechanical properties (i.e., Young's Modulus, storage modulus) to that of DGEBA-NMA. However, it had a lower tensile strength and higher flexural modulus at elevated temperatures. The application of naturally derived, sustainable compounds for the replacement of commercially available petrochemical-based epoxies is of great interest to reduce the environmental impact of these materials. Q-NMA is an attractive candidate for the replacement of bisphenol A-based epoxies in various specialty engineering applications.
authors.affiliation: Department of Chemistry, Department of Chemical Engineering, Departments of Materials Science & Engineering, Texas A&M University, College Station, Texas, 77842-3012, United States.
authors.forename: Samantha L
authors.initials: SL
authors.lastname: Kristufek
authors.affiliation: Department of Chemical and Biomolecular Engineering, University of Houston, Houston, Texas, 77204-4004, United States.
authors.forename: Guozhen
authors.initials: G
authors.lastname: Yang
authors.affiliation: Department of Chemistry, Department of Chemical Engineering, Departments of Materials Science & Engineering, Texas A&M University, College Station, Texas, 77842-3012, United States.
authors.forename: Lauren A
authors.initials: LA
authors.lastname: Link
authors.affiliation: Department of Chemical and Biomolecular Engineering, University of Houston, Houston, Texas, 77204-4004, United States.
authors.forename: Brian J
authors.initials: BJ
authors.lastname: Rohde
authors.affiliation: Department of Chemical and Biomolecular Engineering, University of Houston, Houston, Texas, 77204-4004, United States.
authors.forename: Megan L
authors.initials: ML
authors.lastname: Robertson
authors.affiliation: Department of Chemistry, Department of Chemical Engineering, Departments of Materials Science & Engineering, Texas A&M University, College Station, Texas, 77842-3012, United States. wooley@chem.tamu.edu.
authors.forename: Karen L
authors.identifier: 0000-0003-4086-384X
authors.initials: KL
authors.lastname: Wooley
mesh_terms: D001559:Benzhydryl Compounds / Q000737:chemistry*; D001688:Biological Products / Q000737:chemistry*; D060326:Chemistry Techniques, Synthetic; D004852:Epoxy Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D004853:Epoxy Resins / Q000737:chemistry*; D055595:Mechanical Phenomena; D010636:Phenols / Q000737:chemistry*; D011794:Quercetin / Q000737:chemistry*; D013696:Temperature; D000098826:Bisphenol A Compounds
chemical_list: D001559:Benzhydryl Compounds; D001688:Biological Products; D004852:Epoxy Compounds; D004853:Epoxy Resins; D010636:Phenols; D011794:Quercetin; C006780:bisphenol A; D000098826:Bisphenol A Compounds
keywords: biomass; materials science; quercetin; renewable resources; sustainable chemistry