A Study of Isosorbide Synthesis from Sorbitol for Material Applications Using Isosorbide Dimethacrylate for Enhancement of Bio-Based Resins
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Date
2023-09-04
Authors
Jašek, Vojtěch
Fučík, Jan
Krhut, Jiří
Mravcová, Ludmila
Figalla, Silvestr
Přikryl, Radek
0000-0002-8020-4948Advisor
Referee
Mark
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MDPI
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Abstract
Bio-based cross-linkers can fulfill the role of enhancing additives in bio-sourced curable materials that do not compare with artificial resin precursors. Isosorbide dimethacrylate (ISDMMA) synthesized from isosorbide (ISD) can serve as a cross-linker from renewable sources. Isosorbide is a bicyclic carbon molecule produced by the reaction modification of sorbitol and the optimal conditions of this reaction were studied in this work. The reaction temperature of 130 & DEG;C and 1% w/w amount of para-toluenesulfonic acid (p-TSA) were determined as optimal and resulted in a yield of 81.9%. Isosorbide dimethacrylate was synthesized via nucleophilic substitution with methacrylic anhydride (MAA) with the conversion of 94.1% of anhydride. Formed ISD and ISDMMA were characterized via multiple verification methods (FT-IR, MS, 1H NMR, and XRD). Differential scanning calorimetry (DSC) proved the curability of ISDMMA (activation energy Ea of 146.2 kJ/mol) and the heat-resistant index of ISDMMA (Ts reaching value of 168.9) was determined using thermogravimetric analysis (TGA). Characterized ISDMMA was added to the precursor mixture containing methacrylated alkyl 3-hydroxybutyrates (methyl ester M3HBMMA and ethyl ester E3HBMMA), and the mixtures were cured via photo-initiation. The amount of ISDMMA cross-linker increased all measured parameters obtained via dynamic mechanical analysis (DMA), such as storage modulus (E') and glass transition temperature (Tg), and the calculated cross-linking densities (& nu;e). Therefore, the enhancement influence of bio-based ISDMMA on resins from renewable sources was confirmed.
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Peer-reviewed
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en