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Synthesis of reactive polyamide bearing vinylcyclopropane moieties in the main chain and its cross-linking reaction

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Abstract

A new polyamide bearing vinylcyclopropane (VCP) moieties in the main chain was synthesized from a diamine bearing a VCP moiety. Thermal properties of the resulting polyamide were evaluated by thermogravimetry (TG) and differential scanning calorimetry. TG clarified that the polyamide was much more heat resistant than that of the analogous linear polyurea reported previously, implying that the VCP moieties in the polyamide underwent thermally induced ring-opening reaction to enable cross-linking of the polyamide. The polyamide was cross-linked also by ring-opening reaction triggered by addition of thiyl radical to the vinyl group, demonstrating the usefulness of VCP structure for designing cross-linkable polymers.

Graphical abstract

Polycondensation of diamine bearing a vinylcyclopropane moiety with an acid dichloride proceeded smoothly, affording a novel reactive polyamide bearing vinylcyclopropane moieties in the main chain. The synthesized linear polyamide exhibited much higher thermal resistance compared to the analogous linear polyurea. In addition, the linear polymer underwent cross-linking reaction with a dithiol via ring-opening reactions to produce a cross-linked polymer, suggesting that the introduction of vinylcyclopropane moiety into polymer structure enable an application for polymer reactions.

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Acknowledgements

This research was financially supported by JSR Corporation. High-resolution mass analyses of compounds were performed by the Cooperative Research Program of “Network Joint Research Centre for Materials and Devices” and in the Center for Instrumental Analysis, Kyushu Institute of Technology (KITCIA).

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Authors and Affiliations

  1. Molecular Engineering Institute, Kyushu Institute of Technology, Sensui-cho 1-1, Tobata-ku, Kitakyushu, Fukuoka, 804-8550, Japan

    Shusuke Okamoto & Takeshi Endo

  2. School of Food and Nutritional Science, University of Shizuoka, Yada 1-1, Suruga-ku, Shizuoka, Shizuoka, 422-8525, Japan

    Shusuke Okamoto

  3. Development of Energy and Materials, Faculty of Science and Engineering, Kindai University, Kowakae 3-4-1, Higashiosaka, Osaka, 577-8502, Japan

    Atsushi Sudo

  4. Molecular Engineering Institute, Shiga University of Medical Science, Seta, Otsu, Shiga, 520-2192, Japan

    Takeshi Endo

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  1. Shusuke Okamoto
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Correspondence to Takeshi Endo.

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Okamoto, S., Sudo, A. & Endo, T. Synthesis of reactive polyamide bearing vinylcyclopropane moieties in the main chain and its cross-linking reaction. Polym. Bull. 81, 3545–3562 (2024). https://doi.org/10.1007/s00289-023-04881-8

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  • DOI: https://doi.org/10.1007/s00289-023-04881-8

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