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Utilization of Lignin-Derived Small Molecules: Epoxy Polymers from Lignin Oxidation Products
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    Utilization of Lignin-Derived Small Molecules: Epoxy Polymers from Lignin Oxidation Products
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    • Zhen Fang
      Zhen Fang
      Department of Chemistry, University of Kentucky, Lexington, Kentucky 40506, United States
      More by Zhen Fang
    • Matthew C. Weisenberger
      Matthew C. Weisenberger
      Center for Applied Energy Research (CAER), University of Kentucky, 2540 Research Park Drive, Lexington, Kentucky 40511, United States
    • Mark S. Meier*
      Mark S. Meier
      Department of Chemistry, University of Kentucky, Lexington, Kentucky 40506, United States
      *E-mail: [email protected]
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    ACS Applied Bio Materials

    Cite this: ACS Appl. Bio Mater. 2020, 3, 2, 881–890
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    https://doi.org/10.1021/acsabm.9b00954
    Published January 6, 2020
    Copyright © 2020 American Chemical Society

    Abstract

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    Much effort has been invested in developing methods for producing small molecules from lignin as a way to source feedstock chemicals from renewable sources. Significant progress is being made, and methods for deconstructing lignin are producing good yields of small, mononuclear aromatic products—sufficient amounts to enable studies of the potential use of these compounds as replacements for compounds currently produced from petroleum. To investigate the use of lignin products in epoxies, we begin with aromatic acids that can be produced from lignin, treat them with epichlorohydrin to make glycidyl ethers, and investigate the thermal and mechanical properties of cured mixtures of these compounds with a commercial epoxy resin (EPON 826) and an anhydride curing agent (NMA). While most of the lignin-modified epoxy polymers exhibit good physical and thermal properties, the polymer prepared from p-hydroxybenzoic acid (compound 6) has a higher glass-transition temperature (Tg = 159 °C) than do thermosets made with other lignin-derived materials, such as vanillic acid diglycidyl ether (compound 4) and matches the Tg of cured samples of the commercial EPON-826/NMA epoxy system. This is significant, as p-hydroxybenzoic acid is readily available by simple hydrolysis of several different lignins and functions as a drop-in replacement for 50% of the BPA-based material in this commercial system without significant degradation of material properties. The use of lignin-derived small molecules in high-value systems such as epoxies may help improve the economics of biorefineries.

    Copyright © 2020 American Chemical Society

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    Supporting Information

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    The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acsabm.9b00954.

    • 1H and 13C NMR spectra of products 46; maximum degradation temperature (Tmax) of cured samples; replicated DSC analysis of EPON with NMA; replicated FTIR analysis of sample containing 4 and 6; replicated TGA analysis of sample containing 4 and 6; photographs of cured samples from different monomers with NMA (PDF)

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    This article is cited by 16 publications.

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    ACS Applied Bio Materials

    Cite this: ACS Appl. Bio Mater. 2020, 3, 2, 881–890
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acsabm.9b00954
    Published January 6, 2020
    Copyright © 2020 American Chemical Society

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