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Rigid biphenyl-contained epoxy resins with improved thermal resistant properties

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Abstract

Biphenyl-contained monomer of 1,4-bis[2-(3,4-epoxy cyclohexyl ethyl) dimethylsilyl] biphenyl (BP-SiH-EP) was prepared via hydrosilylation reaction of 1,4-bis(dimethylsilyl) biphenyl (BP-SiH) and 1,2-epoxy-4-vinylcyclohexane in the presence of Karstedt’s catalyst. 1H-NMR, 13C-NMR and FTIR were used to characterize the structure of the obtained monomer. BP-SiH-EP was then cured by methyl hexahydrophthalic anhydride (MeHHPA) with 1-cyanoethyl-2-ethyl-4-methylimidazole as an accelerator. The polymerization behavior was studied by DSC. The results of DMA measurement demonstrate that the cured BP-SiH-EP/MeHHPA can maintain high storage modulus (> 1 GPa) in a wide range of temperature up to 176 °C. According to the damping factor curve of DMA, cured BP-SiH-EP/MeHHPA exhibits a high glass transition temperature (T g) of 192 °C, which is 20 °C higher than that of cured 1,4-bis[2-(3,4-epoxy cyclohexyl ethyl) dimethylsilyl] benzene (DEDSB)/MeHHPA. TGA results show that cured BP-SiH-EP/MeHHPA has good thermal stability (T 5% = 339 °C) due to the high heat-resistance of rigid biphenyl group. Moreover, the crosslinking density of cured BP-SiH-EP/MeHHPA should be lower than that of cured DEDSB/MeHHPA estimated from their chemical structures, which conflicts with the calculated results based on the rubber elasticity equation. The inconsistence indicates that the calculated crosslinking densities are not comparable, possibly owing to their differences in the rigidity of polymer chains and intermolecular interaction.

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Authors and Affiliations

  1. Key Laboratory for Advanced Materials, School of Chemistry & Molecular Engineering, East China University of Science and Technology, Shanghai, 200237, China

    Xiao-yan Wei & Ya-zhuo Shang  (尚亚卓)

  2. Shanghai Wujing Optoelectronics Sci&Tech Co., Ltd, Shanghai, 200093, China

    Bo-xuan Zhao

  3. Department of Materials Science, Fudan University, Shanghai, 200433, China

    Yuan-rong Cheng  (程元荣)

Authors
  1. Xiao-yan Wei
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  2. Bo-xuan Zhao
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  3. Ya-zhuo Shang  (尚亚卓)
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  4. Yuan-rong Cheng  (程元荣)
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Corresponding authors

Correspondence to Ya-zhuo Shang  (尚亚卓) or Yuan-rong Cheng  (程元荣).

Additional information

This work was financially supported by the National Natural Science Foundation of China (Nos. 51403039 and 21476072) and the Natural Science Foundation of Shanghai (No. 13ZR1451300).

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Wei, Xy., Zhao, Bx., Shang, Yz. et al. Rigid biphenyl-contained epoxy resins with improved thermal resistant properties. Chin J Polym Sci 35, 1428–1435 (2017). https://doi.org/10.1007/s10118-017-1975-9

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  • DOI: https://doi.org/10.1007/s10118-017-1975-9

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