Polymer Bulletin

, Volume 57, Issue 5, pp 611–621 | Cite as

Step-Growth Polymerization of 4-(1-Naphthyl)-1,2,4-triazolidine-3,5-dione with Diisocyanates

  • Shadpour MallakpourEmail author
  • Hassan Zandi


We have synthesized 4-(1-naphthyl)-1,2,4-triazolidine-3,5-dione (4-NTD) in high yield and purity from 1-naphthyl isocyanate and used it as a new monomer for polymer synthesis. A series of novel naphthalene-containing polyureas have been successfully prepared from 4-NTD with hexamethylene diisocyanate (HMDI), isophorone diisocyanate (IPDI) and toluene-2,4-diisocyanate (TDI) in N,N-dimethylacetamide (DMAc) or N-methylpyrrolidone (NMP) solution in the presence of pyridine, triethylamine or dibutyltin dilurate as catalysts. Some physical properties and structural characterization of these novel polyureas are reported. Fluorimetric studies of the new monomer, model compound as well as polymers were also investigated.


DMAc Thermal Gravimetric Analysis Polyureas Semicarbazide HMDI 
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  1. 1.
    Morgan PW. (1965) Wiley-Interscience, New York, Chap. 5.Google Scholar
  2. 2.
    Chantarasiri N, Chulamanee C, Mananunsap T, Muangsin N. (2004) Polym. Degr. Stab. 86: 505.Google Scholar
  3. 3.
    Akcelrud L. (2003) Prog. Polym. Sci. 28: 875.Google Scholar
  4. 4.
    Simas ER, Akcelrud L. (2003) J. Luminescence 105: 69.Google Scholar
  5. 5.
    Wang CS, Leu TS. (2000) Polymer 41: 3581.Google Scholar
  6. 6.
    Jikihara T, Matsuya K, Ohta H, Suzuki S, Wakabayashi O. (1981) US, 4, 249, 934, Japan. Chemical Abstract 95, 62219y.Google Scholar
  7. 7.
    (a) Mallakpour SE, Nasr-Isfahani H. (2001) J. Appl. Polym. Sci. 82: 3177 (b) Mallakpour SE, Sheikholeslami B. (1999) Polym. Int. 48: 41.Google Scholar
  8. 8.
    Simlot R, Izydore RA, Wong OT, Hall AH. (1994) J. Pharm. Sci. 83: 367.Google Scholar
  9. 9.
    Hall IH, Wong OT, Simlot R, Miller MC, Izydore R. (1992) Anticancer Res. 12: 1355.Google Scholar
  10. 10.
    Boldi AM, Johnson CE, Eissa HO. (1999) Tetrahedron Lett. 40: 619.Google Scholar
  11. 11.
    Barton DHR, Lusihchi X, Sandoval-Ramirez J. (1983) Tetrahedron Lett. 24: 2995.Google Scholar
  12. 12.
    Paquette LA, Kretschmer G. (1979) J. Am. Chem. Soc. 101: 4655.Google Scholar
  13. 13.
    Herweh JE, Fantazier RM. (1973) Tetrahedron Lett. 14: 2101.Google Scholar
  14. 14.
    Mallakpour S, Rafiee Z. (2004) J. Appl. Polym. Sci. 91: 2103.Google Scholar
  15. 15.
    Mallakpour S, Rafiee Z. (2004) Iranian Polym. J. 13(3): 225.Google Scholar
  16. 16.
    Mallakpour SE, Nasr-Isfahani H. (2001) Polym. Sci. Ser B. 43: 1.Google Scholar

Copyright information

© Springer-Verlag 2006

Authors and Affiliations

  1. 1.Organic Polymer Chemistry Research Laboratory, College of ChemistryIsfahan University of TechnologyIsfahanI.R. Iran

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