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Synthesis, curing behavior, and thermal properties of fluorene-based benzoxazine-endcapped copoly(ether ketone ketone)s

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Abstract

A series of fluorene-based benzoxazine-endcapped copoly(ether ketone ketone)s (co-PEKKs) were successfully synthesized, in which the co-PEKKs were prepared with different molar ratios of 2,7-dihydroxy-9-fluorenone to bisphenol-A. The obtained phenol-ended co-PEKKs reacted with formaldehyde and n-butylamine to yield the benzoxazine-endcapped co-PEKKs (B-PEKKs). The structure of these oligomers was studied by Fourier transform infrared spectroscopy and 1H nuclear magnetic resonance spectroscopy, and the molecular mass of these phenol-ended co-PEKKs was detected by gel permeation chromatography. The thermal behaviors of these B-PEKKs were determined by differential scanning calorimetry. In addition, the thermal and dynamic mechanical properties of the polymer films were investigated by thermogravimetric analysis and dynamic mechanical analysis. The results indicate that the incorporation of co-PEKKs within the benzoxazine backbone considerably improves the toughness of the fluorene-containing polybenzoxazines without much sacrifice of their thermal properties. Furthermore, as the content of 2,7-dihydroxy-9-fluorenone increases, the T 5 values decrease, while the T g values and char yields of the prepared polymers increase to reach their highest values at 256 °C and 64 %, respectively.

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Acknowledgements

The authors greatly appreciated the financial supports from National Natural Science Foundation of China (Project Nos 50973022), Specialized Research Funds for the Doctoral Program of Higher Education (Project No. 20122304110019), Fundamental Research Funds for the Central Universities (Project Nos. HEUCFT1009 and HEUCF201310006), and the open fund of Key Laboratory of Superlight Material and Surface Technology of Ministry of Education, Harbin Engineering University.

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Authors and Affiliations

  1. Polymer Materials Research Center, Key Laboratory of Superlight Material and Surface Technology of Ministry of Education, College of Materials Science and Chemical Engineering, Harbin Engineering University, Harbin, 150001, People’s Republic of China

    Hui Wang, Jun Wang, Tian-tian Feng, Noureddine Ramdani, Yue Li, Xiao-dong Xu & Wen-bin Liu

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  1. Hui Wang
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  2. Jun Wang
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  7. Wen-bin Liu
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Correspondence to Jun Wang or Wen-bin Liu.

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Wang, H., Wang, J., Feng, Tt. et al. Synthesis, curing behavior, and thermal properties of fluorene-based benzoxazine-endcapped copoly(ether ketone ketone)s. J Therm Anal Calorim 119, 1913–1921 (2015). https://doi.org/10.1007/s10973-014-4294-1

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