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Sulfonated polyimide copolymers based on 4,4′-diaminostilbene-2,2′-disulfonic acid and 3,5,3′,5′-tetramethylbenzidine with enhanced solubility

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Abstract

A new series of six-membered ring sulfonated polyimides with different combinations of two comonomers in the nonsulfonated diamine was prepared by one-step high-temperature polycondensation in m-cresol to improve the solubility of the resulting sulfonated polyimides. They are based on 1,4,5,8-naphthalenetetracarboxylic dianhydride, 4,4′-diaminostilbene-2,2-disulfonic acid sulfonated diamine, and equimolar mixture of 3,5,3′,5′-tetramethylbenzidine (TMB) and 4,4′-oxydianiline, bis(4-aminophenyl)methane, or bis(4-(aminophenoxy)-4-phenyl)isopropylidene nonsulfonated diamines. The introduction of TMB comonomer in the nonsulfonated diamine resulted in a remarkable improvement in the solubility of the resulting polyimides in comparison with the corresponding single-monomer nonsulfonated diamine polyimides. Flexible, transparent, and tough membranes were prepared by solution casting method from the different polyimides. The membranes were characterized with FTIR and 1H-NMR spectroscopy, differential scanning calorimetry, thermogravimetric analysis, water uptake, and ion-exchange capacity measurements. They exhibit high thermal stability and good correlation between the ion-exchange capacity and water uptake values.

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Acknowledgments

We thank the University of Jordan for providing chemicals and facilities that made this work possible. We also thank Miss Ruba Zalloum and Miss Fatima Mustafa for their assistance in performing the FTIR, TGA, and 1H-NMR measurements.

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Authors and Affiliations

  1. Department of Chemistry, The University of Jordan, Amman, 11942, Jordan

    Faten M. Abu-Orabi, Mohammed H. Kailani, Bassam A. Sweileh & Mohammad Y. Mustafa

  2. Department of Physics, The University of Jordan, Amman, 11942, Jordan

    Mahmoud Al-Hussein

Authors
  1. Faten M. Abu-Orabi
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  2. Mohammed H. Kailani
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  3. Bassam A. Sweileh
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  4. Mohammad Y. Mustafa
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  5. Mahmoud Al-Hussein
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Correspondence to Mohammed H. Kailani or Mahmoud Al-Hussein.

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Abu-Orabi, F.M., Kailani, M.H., Sweileh, B.A. et al. Sulfonated polyimide copolymers based on 4,4′-diaminostilbene-2,2′-disulfonic acid and 3,5,3′,5′-tetramethylbenzidine with enhanced solubility. Polym. Bull. 74, 895–909 (2017). https://doi.org/10.1007/s00289-016-1752-x

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  • DOI: https://doi.org/10.1007/s00289-016-1752-x

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