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Studies on the isomeric effect of nitrile functionality on the polymerization and thermal properties of ortho-norbornene-based benzoxazine resins

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Abstract

Three norbornene-functional mono-benzoxazines with attached nitrile group at the para-, meta-, and ortho-position with respect to the nitrogen atom in the oxazine ring, respectively, have been synthesized to investigate the isomeric effect of nitrile group on the polymerization and thermal properties of resulting polybenzoxazines. The chemical structures of newly obtained benzoxazine monomers are investigated by 1H and 13C NMR spectroscopy and FT-IR spectroscopy. Besides, the polymerization behaviors including oxazine ring, nitrile group as well as norbornene functionality in each benzoxazine are studied by differential scanning calorimetry (DSC) and in situ FT-IR. In addition, the thermal properties of corresponding polybenzoxazines are investigated by TGA. The nitrile group at ortho-position in benzoxazine has been found to be easier activated to polymerize compared with other two isomers. Moreover, the resulting polybenzoxazine derived from ortho-nitrile containing benzoxazine also shows the best thermal stability with a Td5 of 371 °C, and a char yield of 56%.

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Acknowledgements

This work was financially supported by the National Natural Science Foundation of China (51603093), the Natural Science Foundation of Jiangsu Province (BK 20160515) and the China Postdoctoral Foundation (2018 T110451).

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  1. Research School of Polymeric Materials, School of Materials Science and Engineering, Jiangsu University, Zhenjiang, 212013, China

    Xinye Yu & Kan Zhang

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  1. Xinye Yu
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Correspondence to Kan Zhang.

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Yu, X., Zhang, K. Studies on the isomeric effect of nitrile functionality on the polymerization and thermal properties of ortho-norbornene-based benzoxazine resins. J Polym Res 27, 130 (2020). https://doi.org/10.1007/s10965-020-02087-4

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