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High-performance bio-based thermosetting bismaleimide resins utilizing difurfurylidenecyclopentanone and dicinnamylidene cyclopentanone

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Abstract

Difurfurylidenecyclopentanone (DFCPN) and dicinnamylidene cyclopentanone (DCCPN) were synthesized by aldol condensation reactions of cyclopentanone with furfural and cinnamaldehyde, both derived from renewable resources. The DFCPN and DCCPN were prepolymerized with 4,4′-bismaleimidodiphenylmethane (BMI) at 190 °C and then compression molded at 250 °C to produce cured DFCPN/BMI and DCCPN/BMI resins (DFCPN–BMI and DCCPN–BMI) with a molar ratio of 1/1, 1/2 or 1/3. The FT-IR spectral analysis of the cured resins and FD-MS analysis of the model reaction products using N-phenylmaleimide revealed that maleimide-rich addition copolymerization occurred. All of the cured resins except DCCPN–BMI 1/1 exhibited glass transition temperatures higher than 350 °C and 5 % weight loss temperatures higher than 450 °C, and their values increased with increasing BMI content. When cured resins with the same molar ratio were compared, DFCPN–BMI exhibited a higher flexural strength than DCCPN–BMI. Especially, DFCPN–BMI 1/1 exhibited extremely excellent flexural properties and heat resistance.

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Acknowledgments

We gratefully acknowledge the financial support from the Chiba Institute of Technology. We thank Dr. Naozumi Teramoto and Dr. Toshiaki Shimasaki of our department for their helpful suggestions.

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Authors and Affiliations

  1. Department of Applied Chemistry, Faculty of Engineering, Chiba Institute of Technology, 2-17-1, Tsudanuma, Narashino, Chiba, 275-0016, Japan

    Mitsuhiro Shibata & Eigo Miyazawa

Authors
  1. Mitsuhiro Shibata
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  2. Eigo Miyazawa
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Corresponding author

Correspondence to Mitsuhiro Shibata.

Electronic supplementary material

FT-IR and 1H NMR spectra of DFCPN–PMIs and DCCPN–PMIs are available from electric supplementary material.

Supplementary material 1 (DOCX 584 kb)

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Shibata, M., Miyazawa, E. High-performance bio-based thermosetting bismaleimide resins utilizing difurfurylidenecyclopentanone and dicinnamylidene cyclopentanone. Polym. Bull. 74, 1949–1963 (2017). https://doi.org/10.1007/s00289-016-1815-z

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  • DOI: https://doi.org/10.1007/s00289-016-1815-z

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