University of Oulu

Tuomo P. Kainulainen, Pyry Erkkilä, Terttu I. Hukka, Juho A. Sirviö, and Juha P. Heiskanen, Application of Furan-Based Dicarboxylic Acids in Bio-Derived Dimethacrylate Resins, ACS Applied Polymer Materials 2020 2 (8), 3215-3225, DOI: 10.1021/acsapm.0c00367

Application of furan-based dicarboxylic acids in bio-derived dimethacrylate resins

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Author: Kainulainen, Tuomo P.1; Erkkilä, Pyry1; Hukka, Terttu I.2;
Organizations: 1Research Unit of Sustainable Chemistry, University of Oulu, P.O. Box 4300, FI-90014 Oulu, Finland
2Chemistry and Advanced Materials, Faculty of Engineering and Natural Sciences, Tampere University, P.O. Box 541, FI-33014 Tampere, Finland
3Fibre and Particle Engineering Research Unit, University of Oulu, P.O. Box 4300, FI-90014 Oulu, Finland
Format: article
Version: published version
Access: open
Online Access: PDF Full Text (PDF, 2.3 MB)
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Language: English
Published: American Chemical Society, 2020
Publish Date: 2020-08-14


Two renewable dicarboxylic acids, furan-2,5-dicarboxylic acid and 2,2′-bifuran-5,5′-dicarboxylic acid, were applied as bisphenol A substitutes to prepare partially bio-based dimethacrylate resins. The furan-based dimethacrylates were synthesized using their diglycidyl esters as intermediates, which were then reacted with methacrylic acid. This reaction was found to give isomeric mixtures, where the formed methacrylate end group had three different configurations as elucidated using one-dimensional (1D) and two-dimensional (2D) NMR. The ratio between the different end groups could be controlled to an extent by using 1,1,1,3,3,3-hexafluoroisopropanol as the sole reagent to facilitate a reaction between the furan diglycidyl esters and methacrylic acid. The control over the configuration of the methacrylate end group is demonstrated to be a possible tool to influence the properties of the resultant dimethacrylate monomer and the cured resin. The bifuran dimethacrylates were found to have viscosities of ca. 110–120 Pa·s at 25 °C, while the furan dimethacrylate had a viscosity of about 40 Pa·s at 25 °C. It is demonstrated that by diluting the furan-based dimethacrylates with 40 wt % of methacrylated eugenol, a bio-based reactive diluent, the liquid resins could be cured into thermosets with glass-transition temperatures of 177–209 °C and 5% mass loss temperatures of 359–375 °C under a nitrogen atmosphere.

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Series: ACS applied polymer materials
ISSN: 2637-6105
ISSN-E: 2637-6105
ISSN-L: 2637-6105
Volume: 2
Issue: 8
Pages: 3215 - 3225
DOI: 10.1021/acsapm.0c00367
Type of Publication: A1 Journal article – refereed
Field of Science: 116 Chemical sciences
Funding: Alfred Kordelin Foundation and Magnus Ehrnrooth Foundation are acknowledged for funding.
Copyright information: © 2020 American Chemical Society. This is an open access article published under a Creative Commons Attribution (CC-BY) License, which permits unrestricted use, distribution and reproduction in any medium,provided the author and source are cited.