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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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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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Keywords

  • Bio-based
  • Polyitaconamides
  • Michael ene-amine addition
  • Bulk polycondensation
  • Cross-linked polyamides