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Aromatic polyimides with tertbutyl-substituted and pendent naphthalene units: synthesis and soluble, transparent properties

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Abstract

A novel non-coplanar aromatic diamine monomer, 3,3′-ditertbutyl-4,4′-diaminodiphenyl-4″-naphthylmethane (TAPN) was synthesized by a condensation reaction of 2-tertbutylaniline and 1-naphthaldehyde under catalyst hydrochloric acid. The structure of the monomer was confirmed by FTIR, NMR, elementary analysis and mass spectrometry. A series of aromatic polyimides (PIs) were synthesized via conventional one-step polycondensation from TAPN and various commercial aromatic dianhydrides. All of the PIs exhibit excellent solubility in common organic solvents, even in low boiling point solvents such as chloroform (CHCl3), tetrahydrofuran (THF) and acetone. The PIs present outstanding thermal stability with the glass transition temperature (T g) ranged from 299 °C to 350 °C, and the temperature at 10% weight loss ranged from 490 °C to 504 °C, and high optical transparency with the cutoff wavelengths of 306–356 nm. Moreover, the flexible and tough PI films have prominent mechanical properties with tensile strengths in the range of 77.6–90.5 MPa, tensile modulus in the range of 1.8–2.4 GPa and elongation at break in the range of 6.3%–9.5%, as well as lower dielectric constant (2.89–3.12 at 1 MHz) and lower moisture absorption (0.35%–0.66%).

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Authors and Affiliations

  1. Key Laboratory of New Processing Technology for Nonferrous Metal & Materials, Ministry of Education, and School of Material Science and Engineering, Guilin University of Technology, Guilin, 541004, China

    Chan-juan Liu, Mei Mei, Xiang-lin Pei, Xiao-hua Huang  (黄孝华) & Chun Wei

  2. Ministry of Education Key Laboratory for the Chemistry and Molecular Engineering of Medicinal Resources, School of Chemistry and Pharmaceutical Science, Guangxi Normal University, Guilin, 541004, China

    Chan-juan Liu

Authors
  1. Chan-juan Liu
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  2. Mei Mei
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  3. Xiang-lin Pei
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  4. Xiao-hua Huang  (黄孝华)
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  5. Chun Wei
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Corresponding author

Correspondence to Xiao-hua Huang  (黄孝华).

Additional information

This work was financially supported by the National Natural Science Foundation of China (Nos. 51163003 and 21264005), the fund of Guangxi Natural Science Foundation (Nos. 2014GXNSFAA118040 and 2013GXNSFDA019008) and Guangxi Funds for Specially-appointed Expert.

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Liu, Cj., Mei, M., Pei, Xl. et al. Aromatic polyimides with tertbutyl-substituted and pendent naphthalene units: synthesis and soluble, transparent properties. Chin J Polym Sci 33, 1074–1085 (2015). https://doi.org/10.1007/s10118-015-1658-3

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  • DOI: https://doi.org/10.1007/s10118-015-1658-3

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