Volume 9, Issue 16 p. 2135-2142
Full Paper

Synthesis, Characterization, and Cross-Linking Strategy of a Quercetin-Based Epoxidized Monomer as a Naturally-Derived Replacement for BPA in Epoxy Resins

Samantha L. Kristufek

Samantha L. Kristufek

Department of Chemistry, Department of Chemical Engineering, Departments of Materials Science & Engineering, Texas A&M University, College Station, Texas, 77842-3012 United States

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Guozhen Yang

Guozhen Yang

Department of Chemical and Biomolecular Engineering, University of Houston, Houston, Texas, 77204-4004 United States

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Dr. Lauren A. Link

Dr. Lauren A. Link

Department of Chemistry, Department of Chemical Engineering, Departments of Materials Science & Engineering, Texas A&M University, College Station, Texas, 77842-3012 United States

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Brian J. Rohde

Brian J. Rohde

Department of Chemical and Biomolecular Engineering, University of Houston, Houston, Texas, 77204-4004 United States

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Prof. Megan L. Robertson

Prof. Megan L. Robertson

Department of Chemical and Biomolecular Engineering, University of Houston, Houston, Texas, 77204-4004 United States

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Prof. Karen L. Wooley

Corresponding Author

Prof. Karen L. Wooley

Department of Chemistry, Department of Chemical Engineering, Departments of Materials Science & Engineering, Texas A&M University, College Station, Texas, 77842-3012 United States

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First published: 14 July 2016
Citations: 26

Graphical Abstract

A natural solution: A diglycidyl monomer prepared in two steps using a natural polyphenolic starting material, quercetin, is reacted with nadic methyl anhydride to afford epoxy cross-linked networks. The thermal and mechanical properties of these networks are compared to similarly synthesized bisphenol A-based epoxy materials for potential replacement in advanced engineering applications.

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.