Facile synthesis of novel optically active poly(amide-imide)s containing N,N′-(pyromellitoyl)-bis-l-phenylalanine diacid chloride and 5,5-disubstituted hydantoin derivatives under microwave irradiation

Authors

  • Khalil Faghihi,

    Corresponding author
    1. Organic Polymer Chemistry Research Laboratory, Department of Chemistry, Faculty of Science, Arak University, Arak, 38156, I.R. Iran
    • Organic Polymer Chemistry Research Laboratory, Department of Chemistry, Faculty of Science, Arak University, Arak, 38156, I.R. Iran
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  • Khosrow Zamani,

    1. Organic Polymer Chemistry Research Laboratory, Department of Chemistry, Faculty of Science, Arak University, Arak, 38156, I.R. Iran
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  • Azzizullah Mirsamie,

    1. Organic Polymer Chemistry Research Laboratory, Department of Chemistry, Faculty of Science, Arak University, Arak, 38156, I.R. Iran
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  • Shadpour Mallakpour

    1. Organic Polymer Chemistry Research Laboratory, College of Chemistry, Isfahan University of Technology, Isfahan, 84156, I.R. Iran
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Abstract

Pyromellitic dianhydride (1,2,4,5-benzenetetracarboxylic acid 1,2,4,5-dianhydide) (1) was reacted with L-phenylalanine (2) in a mixture of acetic acid and pyridine (3 : 2) at room temperature, then was refluxed at 90–100°C and N,N′-(Pyromellitoyl)-bis-L-phenylalanine diacid (3) was obtained in quantitative yield. The imide-acid (3) was converted to N,N′-(Pyromellitoyl)-bis-L-phenylalanine diacid chloride (4) by reaction with thionyl chloride. Rapid and highly efficient synthesis of poly(amide-imide)s (6a–f) was achieved under microwave irradiation by using a domestic microwave oven from the polycondensation reactions of N,N′-(Pyromellitoyl)-bis-L-phenylalanine diacid chloride (4) with six different derivatives of 5,5-disubstituted hydantoin compounds (5a–f) in the presence of a small amount of a polar organic medium that acts as a primary microwave absorber. Suitable organic media was o-cresol. The polycondensation proceeded rapidly, compared with the conventional melt polycondensation and solution polycondensation, and was almost completed within 10 min, giving a series of poly(amide-imide)s with inherent viscosities about 0.28–0.44 dL/g. The resulting poly(amide-imide)s were obtained in high yield and are optically active and thermally stable. All of the above compounds were fully characterized by means of FTIR spectroscopy, elemental analyses, inherent viscosity (ηinh), solubility test and specific rotation. Thermal properties of the poly(amide-imide)s were investigated using thermal gravimetric analysis (TGA). © 2003 Wiley Periodicals, Inc. J Appl Polym Sci 91: 516–524, 2004

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