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Synthesis and properties of crosslinked poly(arylene ether nitriles) containing pendant phthalonitrile

Authors

  • Jian Yang,

    1. Research Branch of Functional Materials, Institute of Microelectronic and Solid State Electronic, High-Temperature Resistant Polymers and Composites Key Laboratory of Sichuan Province, University of Electronic Science and Technology of China, Chengdu 610054, People's Republic of China
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  • Xulin Yang,

    1. Research Branch of Functional Materials, Institute of Microelectronic and Solid State Electronic, High-Temperature Resistant Polymers and Composites Key Laboratory of Sichuan Province, University of Electronic Science and Technology of China, Chengdu 610054, People's Republic of China
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  • Yingqing Zhan,

    1. Research Branch of Functional Materials, Institute of Microelectronic and Solid State Electronic, High-Temperature Resistant Polymers and Composites Key Laboratory of Sichuan Province, University of Electronic Science and Technology of China, Chengdu 610054, People's Republic of China
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  • Yanke Zou,

    1. Research Branch of Functional Materials, Institute of Microelectronic and Solid State Electronic, High-Temperature Resistant Polymers and Composites Key Laboratory of Sichuan Province, University of Electronic Science and Technology of China, Chengdu 610054, People's Republic of China
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  • Rui Zhao,

    1. Research Branch of Functional Materials, Institute of Microelectronic and Solid State Electronic, High-Temperature Resistant Polymers and Composites Key Laboratory of Sichuan Province, University of Electronic Science and Technology of China, Chengdu 610054, People's Republic of China
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  • Xiaobo Liu

    Corresponding author
    1. Research Branch of Functional Materials, Institute of Microelectronic and Solid State Electronic, High-Temperature Resistant Polymers and Composites Key Laboratory of Sichuan Province, University of Electronic Science and Technology of China, Chengdu 610054, People's Republic of China
    • Research Branch of Functional Materials, Institute of Microelectronic and Solid State Electronic, University of Electronic Science and Technology of China, Chengdu 610054, People's Republic of China
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Abstract

In this study, poly(arylene ether nitriles) containing pendant carboxyl groups (PEN-COOH) was first synthesized via nucleophilic aromatic substitution reaction from phenolphthalein, hydroquinone and 2,6-dicholorobenzonitrile. Then, poly(arylene ether nitriles) with pendant phthalonitrile groups (PEN-CN) was obtained via the Yamazaki–Higashi phosphorylation route from 4-(4-aminophenoxy)phthalonitrile (APN) with PEN-COOH in the presence of CaCl2, thus the phthalonitrile as pendant groups in PEN-CN were easily crosslinked by further thermal treatment. The effect of crosslinking density on the thermal stabilities, dielectric properties and water absorption of the PEN-CNs was investigated. These results showed that the Tg of PEN-CN was improved from 182 to 213°C, dielectric constant (ε) was increased from 3.1 to 3.9, and dielectric loss (tan δ) was decreased from 0.090 to 0.013 at 1 kHz. The water absorption of PEN-CNs after thermal crosslinking was <1.01 wt %, which showed excellent water resisting property. Therefore, this kind of poly(arylene ether nitriles) containing pendant phthalonitrile could be a good candidate as matrix resins for high-performance polymeric materials. © 2012 Wiley Periodicals, Inc. J. Appl. Polym. Sci., 2013

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