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Synthesis and characterization of an aromatic diamine and its polyimides containing asymmetric large side groups

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Abstract

A novel aromatic diamine monomer with asymmetric large side group: 4-(2,4,6-trimethyl)phenoxy-1,3-diaminobenzene, was synthesized by a two-step organic reaction. The monomer was separately subjected to a one-step high-temperature polycondensation reaction with three commercial aromatic dianhydrides to obtain a series of polyimides. Their structures and properties were characterized and studied by FTIR, NMR, UV, TGA, DSC, etc. The obtained polyimides showed excellent solubility not only in high-boiling solvents such as NMP, DMAc, and DMF, but also in low-boiling solvents such as CHCl3 and CH2Cl2. Their tensile strength was in the range of 76.9–93.5 MPa, the elongation at break was between 4.8% and 7.3%, and the modulus of elasticity was in the range of 1.6–1.8 GPa. The obtained films exhibited good optical transparency, and the representative polyimide derived from 4,4′-oxydiphthalic dianhydride exhibited a light transmittance of more than 83% at a wavelength of 450 nm. Moreover, these polyimides also possessed good thermal properties. Their glass transition temperatures are between 285 °C and 345 °C, and the 10% weight loss temperature in air and nitrogen is above 463 °C, showing excellent thermal properties.

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Acknowledgements

Foundation items: National Natural Science Foundation of China (21404016); Key Research Project of Jiangsu Province (BE2017645); Scientific Research and Innovation Project for Graduate Students in Jiangsu Province (SJCX18-0954), and a Project Funded by the Priority Academic Program Development of Jiangsu Higher Education Institutions of China.

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Authors and Affiliations

  1. Jiangsu Key Laboratory of Environmentally Friendly Polymeric Materials, School of Materials Science and Engineering, Changzhou University, Changzhou, 213164, Jiangsu, China

    Chenyi Wang, Bin Yu, Cairong Jiang, Xiaoyan Zhao, Jian Li & Qiang Ren

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  1. Chenyi Wang
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  2. Bin Yu
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  3. Cairong Jiang
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  4. Xiaoyan Zhao
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  5. Jian Li
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Correspondence to Chenyi Wang or Xiaoyan Zhao.

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Wang, C., Yu, B., Jiang, C. et al. Synthesis and characterization of an aromatic diamine and its polyimides containing asymmetric large side groups. Polym. Bull. 77, 6509–6523 (2020). https://doi.org/10.1007/s00289-019-03085-3

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  • DOI: https://doi.org/10.1007/s00289-019-03085-3

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