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Facile preparation of the novel castor oil-based benzoxazine–urethane copolymer with improved high-frequency dielectric properties

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Abstract

The novel star shaped benzoxazine-co-urethane prepolymers are first synthesized from the natural resource castor oil, hydroxyl terminated benzoxazine and diisocyanate through the facile one-pot formulation method. Then the cured benzoxazine copolymers can be obtained by the ring-opening polymerization of oxazine groups of the prepared prepolymers. Both hexamethylene diisocyanate and 4,4′-methylenediphenyl diisocyanate are employed as aliphatic and aromatic diisocyanate, respectively, to clarify their effects on the chemical structure and high-frequency dielectric properties of copolymers. In comparison with the pure polybenzoxazine, the copolymer films occupy the improved high-frequency dielectric properties owing to the introduction of three branching aliphatic castor oil, leading to the reduction of molecular polarity and the improvement of free volume. It should be noted that the aliphatic diisocyanate not only decreases the polarity of the copolymer, but also enhances the intermolecular interaction and intermolecular entanglement between castor oil and benzoxazine for the copolymers. Accordingly, the aliphatic diisocyanate based poly(benzoxazine-co-urethane) occupies the minimum high-frequency dielectric constants (2.94, 5 GHz; 2.96, 10 GHz) and relatively high glass transition temperature (220 °C). Therefore, this work not only provides a simple path for improving high-frequency dielectric properties of benzoxazine, but also gives some insight into the effects of diisocyanates on the formation and high-frequency dielectric properties of poly(benzoxazine-co-urethane)s.

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Acknowledgements

We gratefully thank the SRF for ROCS, State Education Ministry (SEM1341), People’s Republic of China, Hubei Provincial Department of Education (XD2010037), and the grant of the Opening Project of State Key Laboratory of Polymer Materials Engineering (Sichuan University) (KF201106) and Engineering Research Center of Nano-Geomaterials of Ministry of Education (CUG2015).

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Author notes

  1. Yiwan Huang

    Present address: Graduate School of Life Science, Hokkaido University, Sapporo, 060–0810, Japan

Authors and Affiliations

  1. Faculty of Materials Science and Chemistry, China University of Geosciences, Wuhan, 430074, People’s Republic of China

    Ming Zeng, Tao Pang, Jiangbing Chen, Yiwan Huang & Qingyu Xu

  2. Engineering Research Center of Nano-Geomaterials of Ministry of Education, China University of Geosciences, Wuhan, 430074, People’s Republic of China

    Ming Zeng

  3. State Key Laboratory of Polymer Materials Engineering, Sichuan University, Chengdu, 610000, People’s Republic of China

    Yi Gu

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  1. Ming Zeng
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Zeng, M., Pang, T., Chen, J. et al. Facile preparation of the novel castor oil-based benzoxazine–urethane copolymer with improved high-frequency dielectric properties. J Mater Sci: Mater Electron 29, 5391–5400 (2018). https://doi.org/10.1007/s10854-017-8505-y

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