Facile Synthetic Route Toward High Conversion Primary Aliphatic Poly(vinyl benzyl isocyanate) via Iodination

High Conversion Aliphatic Polyisocyanates via Iodination

Abstract

Aliphatic isocyanato polymers, poly(vinyl benzyl isocyanate)s were synthesized via iodination and isocyanation from starting materials poly(vinyl benzyl chloride)s. This new process does not require phosgene which is highly toxic. This synthetic route takes advantage of the unique property of iodide ion which functions not only as a good nucleophile for iodination but also as a leaving group for isocyanation. The isocyanation conditions are mild with reaction temperatures ranging from 30 to 70 °C. In addition, the process is very efficient with conversions over 90%, yielding no dimer, trimer or other byproducts.

References

  1. 1

    A. Mahajan, S. R. Chhabra, and W. C. Chan, Tetrahedron Lett., 40, 4909 (1999).

  2. 2

    R. J. Booth and J. C. Hodges, J. Am. Chem. Soc., 119, 4882 (1997).

  3. 3

    G. H. Hu, H. Li, L. F. Feng, and L. A. Pessan, J. Appl. Polym. Sci., 88, 1799 (2003).

  4. 4

    S. Mohammed, E. S. Daniels, A. Klein, and M. S. El-Aasser, J. Appl. Polym. Sci., 67, 559 (1998).

  5. 5

    D. D. Wisnoski, W. H. Leister, K. A. Strauss, Z. Zhao, and C. W. Lindsley, Tetrahedron Lett., 44, 4321 (2003).

  6. 6

    K. R. Yoon and S. Lee, J. Macromol. Sci., Part B: Phys., 45, 859 (2006).

  7. 7

    L. Barner, S. Perera, S. Sandanayake, and T. P. Davis, J. Polym. Sci., Part A: Polym. Chem., 44, 857 (2006).

  8. 8

    M. C. Himel, M. Park, and L. M. Richard, U. S. Patent 2 866 801 (1958).

  9. 9

    S. R. Gaonkar, K. Srinivasan, and G. S. Kumar, J. Polym. Sci., Part A: Polym. Chem., 30, 1911 (1992).

  10. 10

    A. Holm and C. Wentrup, Acta Chem. Scand., 20, 2123 (1966).

  11. 11

    C. J. Hawker, J. Am. Chem. Soc., 116, 11185 (1994).

  12. 12

    C. J. Hawker and J. L. Hedrick, Macromolecules, 28, 2993 (1995).

  13. 13

    C. J. Hawker, Acc. Chem. Res., 30, 373 (1997).

  14. 14

    M. K. Georges, R. P. N. Veregin, P. M. Kazmaier, and G. K. Hamer, Macromolecules, 26, 2987 (1993).

  15. 15

    A. Goto and T. Fukuda, Macromol. Chem. Phys., 201, 2138 (2000).

  16. 16

    M. Baumann and G. Schmidt-Naake, Macromol. Chem. Phys., 202, 2727 (2001).

  17. 17

    W. Devonport, L. Michalak, E. Malmström, M. Mate, B. Kurdi, C. J. Hawken, G. G. Barclay, and R. Sinta, Macromolecules, 30, 1929 (1997).

  18. 18

    P. M. Kazmaier, K. Daimon, M. K. Georges, G. K. Hamer, and R. P. N. Veregin, Macromolecules, 30, 2228 (1997).

  19. 19

    T. Tsoukatos, S. Pispas, and N. Hadjichristidis, Macromolecules, 33, 9504 (2000).

  20. 20

    D. A. Wang, C. G. Williams, Q. Li, B. Sharma, and J. H. Elisseeff, Biomaterials, 24, 3969 (2003).

  21. 21

    R. W. Arcís, A. López-Macipe, M. Toledano, E. Osorio, R. Rodríguez-Clemente, J. Murtra, M. A. Fanovich, and C. D. Pascual, Dent. Mater., 18, 49 (2002).

  22. 22

    W. H. Ting, S. A. Dai, Y. F. Shih, I. K. Yang, W. C. Su, and R. J. Jeng, Polymer, 49, 1497 (2008).

  23. 23

    W. H. Ting, C. C. Chen, S. A. Dai, S. Y. Suen, I. K. Yang, Y. L. Liu, F. M. C. Chen, and R. J. Jeng, J. Mater. Chem., 19, 4819 (2009).

  24. 24

    L. H. Sperling, “Introduction to physical polymer science,” 2nd ed., Wiley, New York, 1992.

    Google Scholar 

Download references

Author information

Affiliations

Authors

Corresponding author

Correspondence to Ru-Jong Jeng.

Rights and permissions

Reprints and Permissions

About this article

Cite this article

Ting, WH., Dai, S., Lee, HT. et al. Facile Synthetic Route Toward High Conversion Primary Aliphatic Poly(vinyl benzyl isocyanate) via Iodination. Polym J 41, 1011–1017 (2009). https://doi.org/10.1295/polymj.PJ2009132

Download citation

Keywords

  • Poly(vinylbenzyl isocyanate)
  • Iodination
  • Isocyanation
  • TEMPO

Search

Quick links