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Polymer Bulletin

, Volume 75, Issue 3, pp 1055–1073 | Cite as

Synthesis, characterization and dehydrogenase activity of novel biodegradable nanostructure spherical shape poly(urethane-imide-sulfonamide) as pseudo-poly(amino acid)s from l-tyrosine

  • Farhang Tirgir
  • Mahboobeh Soleimani
  • Ghasem Moghadam
  • Mahsa Khorshidi
Original Paper

Abstract

For the first time, the N,N-(pyromelitoylimidyl)-bis-(4-hydroxy tyrosine dimethyl ester benzyl sulfonamide) (PHTBS) as diphenolic monomer containing tyrosine was formed in three steps. PHTBS employed as a monomer in the design of biodegradable and biological polymers. The polycondensation of the this monomer with various aromatic and aliphatic diisocyanates such as 4,4-methylenebis-(4-phenylisocyanate) (a), hexamethylene diisocyanate (b), isophorone diisocyanate (c) and toluene-2,4-diisocyanate (d) was carried out under traditional polymerization conditions to give poly(urethane-imide-sulfonamide)s (PUIS)s as pseudo-poly(amino acid)s (PAAs). The novel PHTBS and obtained PUISs were characterized with FTIR, 13C-NMR, 1H-NMR spectroscopy, X-ray diffraction (XRD), field emission scanning electron microscopy and elemental analysis. Differential scanning calorimetry and thermogravimetric analysis were used to determine the thermal properties of the polymers. Morphology probes showed these PUISs were nanoshape polymers. On the basis of thermogravimetric analysis data, such PUISs are thermally stable and can be classified as self-extinguishing polymers. The obtained PUISs possessed more bioactivity, moderate thermal stability and high solubility in common organic solvents. Furthermore, soil enzymatic of the PHTBS and the obtained PUISs assay showed that the synthetic materials are biologically active and then could be classified as bioactive and biodegradable compounds.

Keywords

Nanostructured polymers Poly(urethane-imide-sulfonamide)s Dehydrogenase activity Tyrosine 

Notes

Acknowledgements

We wish to express our gratitude to the Research Affairs Division, Islamic Azad University, Shahrekord Branch, for partial financial support. Further financial support from Young Researchers and Elites Club is gratefully acknowledged.

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Copyright information

© Springer-Verlag Berlin Heidelberg 2017

Authors and Affiliations

  • Farhang Tirgir
    • 1
  • Mahboobeh Soleimani
    • 2
  • Ghasem Moghadam
    • 2
  • Mahsa Khorshidi
    • 2
  1. 1.Department of Chemistry, Faculty of ScienceShahrekord BranchShahrekordIran
  2. 2.Young Researchers and Elite ClubShahrekord BranchShahrekordIran

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