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Bio-based cross-linked polyitaconamides synthesized through a Michael ene-amine addition and bulk polycondensation

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Abstract

A simple method is established to synthesize bio-based cross-linked polyitaconamides (cPITAs) through a Michael ene-amine addition and bulk polycondensation. A tetraester, i.e. tetramethyl piperazine-N,N′-bis(2-methylene butanedioate) (TMPB), was synthesized through a Michael addition of dimethyl itaconate and piperazine at 90 °C. Bulk polycondensation of TMPB with butanediamine or hexamethylenediamine was conducted at 130–170 °C under atmospheric pressure, and several cPITAs with tunable properties were prepared. The Michael addition and the polycondensation were monitored by FT-IR and 1H NMR spectra. The cPITA films were characterized by DSC, WAXS, TGA, dynamic mechanical analysis, and tensile test. cPITAs exhibited Tg ranging from 58 to 72 °C, tensile strength up to 85 MPa, and strain at break from 9% to 17%.

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Acknowledgments

This work was financially supported by Beijing Natural Science Foundation (No. 2182056) and National Natural Science Foundation of China (Grant No. 21244006).

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Authors and Affiliations

  1. Key Laboratory of Carbon Fiber and Functional Polymers (Beijing University of Chemical Technology), Ministry of Education, College of Materials Science and Engineering, Beijing University of Chemical Technology, Beijing, 100029, China

    Kuan Liang, Jingbo Zhao, Ganggang Zhang, Zhiyuan Zhang, Ling Shi & Junying Zhang

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  1. Kuan Liang
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  2. Jingbo Zhao
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  3. Ganggang Zhang
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  4. Zhiyuan Zhang
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  5. Ling Shi
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Correspondence to Jingbo Zhao or Junying Zhang.

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Liang, K., Zhao, J., Zhang, G. et al. Bio-based cross-linked polyitaconamides synthesized through a Michael ene-amine addition and bulk polycondensation. J Polym Res 27, 56 (2020). https://doi.org/10.1007/s10965-020-2030-z

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