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Environmentally Friendly Methodology for Preparation of Amino Acid Containing Polyamides

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Abstract

A short and green method for the preparation of optically active aromatic polyamides (PAs) using tetrabutylammonium bromide (TBAB) as a molten ionic liquid is reported. Polycondensation reactions of amino acid containing diacid (2S)-5-(4-methyl-2-phthalimidylpentanoylamino)isophthalic acid with various commercially available diisocyanates in molten TBAB as a green medium or in N-methylpyrrolidone as common organic solvent with or without dibutyltin dilaurate as a catalyst under microwave irradiation were carried out. Various PAs were obtained with high yields and moderate inherent viscosities in the rang of 0.30–0.57 dL/g. The obtained polymers were characterized by FT-IR, specific rotation measurements, and representative of them by 1H NMR and elemental analysis techniques. Thermal properties of PAs were evaluated by thermogravimetric analysis and the results showed that the 10% weight loss temperature in a nitrogen atmosphere for four representative samples were more than 258 °C, which indicates that the resulting PAs have good thermal stability as well as excellent solubility.

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Acknowledgments

We wish to express our gratitude to the Research Affairs Division Isfahan University of Technology (IUT), Isfahan, for partial financial support. Further financial support from National Elite Foundation (NEF) and Center of Excellency in Sensors and Green Chemistry Research (IUT) is gratefully acknowledged.

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Authors and Affiliations

  1. Organic Polymer Chemistry Research Laboratory, Department of Chemistry, Isfahan University of Technology, Isfahan, 84156-83111, IR, Iran

    Shadpour Mallakpour & Mohammad Dinari

  2. Nanotechnology and Advanced Materials Institute, Isfahan University of Technology, Isfahan, 84156-83111, IR, Iran

    Shadpour Mallakpour

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  1. Shadpour Mallakpour
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  2. Mohammad Dinari
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Correspondence to Shadpour Mallakpour.

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Mallakpour, S., Dinari, M. Environmentally Friendly Methodology for Preparation of Amino Acid Containing Polyamides. J Polym Environ 18, 705–713 (2010). https://doi.org/10.1007/s10924-010-0253-5

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