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A Study of Isosorbide Synthesis from Sorbitol for Material Applications Using Isosorbide Dimethacrylate for
Vojtěch Jašek1, Jan Fučík2, Jiří Krhut1
1Institute of Materials Chemistry, Faculty of Chemistry, Brno University of Technology, 61200 Brno, Czech Republic.
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 °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 E of 146.2 kJ/mol) and the heat-resistant index of ISDMMA (T 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 (ν). Therefore, the enhancement influence of bio-based ISDMMA on resins from renewable sources was confirmed.
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