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Synthesis and properties of ortho-linked aromatic poly(ester-amide)s and poly(ester-imide)s bearing 2,3-bis(benzoyloxy)naphthalene units

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Abstract

Two new naphthalene-ring-containing bis(ester-amine)s, 2,3-bis(4-aminobenzoyloxy)naphthalene (p-2) and 2,3-bis(3-aminobenzoyloxy)naphthalene (m-2), were prepared from the condensation of 2,3-dihydroxynaphthalene with 4-nitrobenzoyl chloride and 3-nitrobenzoyl chloride, respectively, followed by catalytic hydrogenation. The novel aromatic poly(ester-amide)s and poly(ester-imide)s having 2,3-linked bis(benzoyloxy)naphthalene units have been synthesized from the polycondensation reactions of bis(ester-amine)s (p-2 and m-2) or an equimolar mixture of 4,4′-oxydianiline and p-2 or m-2 with various aromatic dicarboxylic acids and dianhydrides. The synthesis of the poly(ester-amide)s was achieved by the phosphorylation polyamidation reaction by means of triphenyl phosphate, and the synthesis of the poly(ester-imide)s included ring-opening polyaddition to give poly(amic acid)s followed by chemical imidization to polyimides. Most of the poly(ester-amide)s were readily soluble in various organic solvents. Six poly(ester-amide)s and two poly(ester-imide)s derived from less rigid diacids and dianhydrides, respectively, were amorphous and could be solution-cast into transparent and tough films with good mechanical properties. Most of the poly(ester-amide)s displayed discernible glass-transition temperatures (T gs) between 192 and 223 °C in the DSC traces. All of the poly(ester-imide)s, except for one sample, showed clear T g values between 225 and 265 °C by DSC. These poly(ester-imide)s showed excellent thermal stability with 10 wt% loss temperatures above 460 °C in nitrogen or air.

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Authors and Affiliations

  1. Department of Chemical Engineering, National Taipei University of Technology, 1 Chunghsiao East Road, 3rd Section, Taipei, 100, Taiwan, Republic of China

    Wenjeng Guo

  2. Department of Chemical Engineering, Tatung University, 40 Chungshan North Road, 3rd Section, Taipei, 104, Taiwan, Republic of China

    Wen-Tsuen Leu & Sheng-Huei Hsiao

Authors
  1. Wenjeng Guo
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  2. Wen-Tsuen Leu
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  3. Sheng-Huei Hsiao
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Correspondence to Sheng-Huei Hsiao.

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Guo, W., Leu, WT. & Hsiao, SH. Synthesis and properties of ortho-linked aromatic poly(ester-amide)s and poly(ester-imide)s bearing 2,3-bis(benzoyloxy)naphthalene units. J Polym Res 14, 359–372 (2007). https://doi.org/10.1007/s10965-007-9118-6

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  • DOI: https://doi.org/10.1007/s10965-007-9118-6

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