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A highly active bio-based epoxy resin with multi-functional group: synthesis, characterization, curing and properties

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Abstract

A bio-based epoxy resin, triglycidyl ether of resveratrol (TGER), was synthesized based on the renewable resveratrol deriving from tannins. The structure and properties of TGER have been characterized by 1H NMR, 13C NMR, FTIR, GPC and viscosity measurement. Besides, systematical investigation was carried out on the curing reaction of TGER and diaminodiphenylmethane (DDM), assisted by the characterization of mechanical properties and thermal properties of cured TGER/DDM by means of differential scanning calorimetry, thermogravimetric analysis, dynamic mechanical analysis (DMA), flexural and impact measurement. Non-isothermal and isothermal curing analysis showed that TGER/DDM system, deriving from autocatalytic curing reaction, possessed 40 °C lower curing temperature (84 °C) than bisphenol A diglycidyl ether (DGEBA) (124 °C) and much lower activation energy than DGEBA/DDM system calculated by Kissinger equation. DMA revealed that TGER possessed high glass transition temperature (T g = 148 °C) and glassy storage modulus (2.391 GPa@23 °C). Meanwhile, TGER/DDM thermosets also exhibited good mechanical properties and heat resistance, illustrating that multi-phenol group and stilbene group of resveratrol endowed polymer with high cross-linking density and rigidness. Therefore, TGER could be a promising alternative to petroleum-based epoxy resin.

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Acknowledgements

The authors acknowledge financial support from The Jilin Province Science and Technology Innovation and Achievements Transformation Project of China (20140306011GX), the National Natural Science Foundation of China (Grant No. 21644003), the National Natural Science Foundation of China (Grant No. 51603020).

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Authors and Affiliations

  1. College of Chemistry and Life Science, Jilin Province Key Laboratory of Carbon Fiber Development and Application, Changchun University of Technology, Changchun, 130012, People’s Republic of China

    Lei Shang, Xiuping Zhang, Mengjie Zhang, Lin Jin, Liu Liu, Linghan Xiao, Ming Li & Yuhui Ao

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  1. Lei Shang
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  2. Xiuping Zhang
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Contributions

LS and YA conceived and designed the experiments. YA contributed to reagents, materials and analysis tools. LS, XZ, MZ, LJ and LL performed the experiments. LS, LX and ML contributed significantly to analysis and manuscript preparation. LS performed the data analyses and wrote the manuscript. LS and YA helped perform the analysis with constructive discussions.

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Correspondence to Yuhui Ao.

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Shang, L., Zhang, X., Zhang, M. et al. A highly active bio-based epoxy resin with multi-functional group: synthesis, characterization, curing and properties. J Mater Sci 53, 5402–5417 (2018). https://doi.org/10.1007/s10853-017-1797-8

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