화학공학소재연구정보센터
Macromolecular Research, Vol.17, No.8, 557-562, August, 2009
Investigation on Chain Transfer Reaction of Benzene Sulfonyl Chloride in Styrene Radical Polymerization
E-mail:
The free radical polymerization of styrene was initiated with azobis(isobutyronitrile) in the presence of benzene sulfonyl chloride. Analysis of the terminal structures of the obtained polystyrene with 1H NMR spectroscopy revealed the presence of a phenylsulfonyl group at the α-end and a chlorine atom at the ω-end of each polystyrene chain. The terminal chlorine atom in the polystyrene chains was further confirmed through atom transfer radical polymerization (ATRP) of styrene and methyl acrylate using the obtained polystyrenes as macroinitiators and CuCl/2,2'-bipyridine as the catalyst system. GPC traces of the products obtained in ATRP at different reaction times were clearly shifted to higher molecular weight direction, indicating that nearly all the macroinitiator chains initiated ATRP of the second monomers. In addition, the number-average molecular weights of the polystyrenes increased directly proportional to the monomer conversions, and agreed well with the theoretical ones.
  1. Blum J, Scharf G, J. Org. Chem., 35, 1895 (1970)
  2. Truce WE, Goralski CT, Christensen LW, J. Org. Chem., 35, 4217 (1970)
  3. Amiel Y, J. Org. Chem., 36, 3691 (1971)
  4. Amiel Y, J. Org. Chem., 36, 3697 (1971)
  5. Truce WE, Wolf GC, J. Org. Chem., 36, 1727 (1971)
  6. Sinnreich J, Asscher M, J. Chem. Soc. Perkin. Trans. I, B4, 1543 (1972)
  7. Orochov A, Asscher M, Vofsi D, J. Chem. Soc. Perkin. Trans. II, BH, 1000 (1973)
  8. Amiel Y, J. Org. Chem., 39, 3867 (1974)
  9. Takahara Y, Iino M, Matsuda M, Bull. Chem. Soc. Jpn., 49, 2268 (1976)
  10. Namigata K, Sawada H, Kobayashi M, J. Org. Chem., 48, 3793 (1983)
  11. Kamigata N, Ozaki J, Kobayashi M, J. Org. Chem., 50, 5045 (1985)
  12. Kamigata N, Fukushima T, Yoshida M, J. Chem. Soc. Commun., 20, 1559 (1989)
  13. Kamigata N, Fukushima T, Terakawa Y, Yoshida M, Sawada H, J. Chem. Soc. Perkin. Trans. I, B4, 627 (1991)
  14. Percec V, Barboiu B, Macromolecules, 28(23), 7970 (1995)
  15. Percec V, Barboiu B, Neumann A, Ronda JC, Zhao MY, Macromolecules, 29(10), 3665 (1996)
  16. Percec V, Barboiu B, Polym. Prepr. (Am. Chem. Soc. Div. Polym. Chem.), 38, 733 (1997)
  17. Percec V, Kim HJ, Barboiu B, Macromolecules, 30(21), 6702 (1997)
  18. Percec V, Kim HJ, Barboiu B, Macromolecules, 30(26), 8526 (1997)
  19. Percec V, Barboiu B, Kim HJ, J. Am. Chem. Soc., 120(2), 305 (1998)
  20. Percec V, Barboiu B, Bera TK, van der Sluis M, Grubbs RB, Frechet JMJ, J. Polym. Sci. A: Polym. Chem., 38(S), 4776 (2000)
  21. Matsuyama M, Kamigaito M, Sawamoto M, J. Polym. Sci. A: Polym. Chem., 34(17), 3585 (1996)
  22. Grimaud T, Matyjaszewski K, Macromolecules, 30(7), 2216 (1997)
  23. Robello DR, Andre A, McCovick TA, Kraus A, Mourey TH, Macromolecules, 35(25), 9334 (2002)
  24. Ejaz M, Yamamoto S, Ohno K, Tsujii Y, Fukuda T, Macromolecules, 31(17), 5934 (1998)
  25. Ejaz M, Ohno K, Tsujii Y, Fukuda T, Macromolecules, 33(8), 2870 (2000)
  26. Ejaz M, Tsujii Y, Fukuda T, Polymer, 42(16), 6811 (2001)
  27. Tsujii Y, Ejaz M, Yamamoto S, Fukuda T, Shigeto K, Mibu K, Shinjo T, Polymer, 43(13), 3837 (2002)
  28. Ejaz M, Yamamoto S, Tsujii Y, Fukuda T, Macromolecules, 35(4), 1412 (2002)
  29. Iino M, Igarashi M, Matsuda M, Macromolecules, 12, 697 (1979)
  30. Boutevin B, J. Polym. Sci. A: Polym. Chem., 38(18), 3235 (2000)
  31. Li H, Zhang YM, Liu YG, J. Appl. Polym. Sci., 101(2), 1089 (2006)
  32. Destarac M, Pees B, Boutevin B, Macromol. Chem. Phys., 201, 1189 (2000)
  33. Batt-Coutrot D, Haddleton DM, Jarvis AP, Kelly RL, Eur. Polym. J., 39, 2243 (2003)
  34. Semsarzadeh MA, Mirzaei A, Vasheghani-Farahani E, Haghighi MN, Eur. Polym. J., 39, 2193 (2003)
  35. Ueda A, Nagai S, in Polymer handbook, 4th Ed., Brandup J, Immergut EH, Grulke EA, Eds., Wiley-Interscience, New York, 1999, Vol. 1, pp 97-168
  36. Kato M, Kamigaito M, Sawamoto M, Higashimura T, Macromolecules, 28(5), 1721 (1995)
  37. Wang JS, Matyjaszewski K, J. Am. Chem. Soc., 117(20), 5614 (1995)
  38. Matyjaszewski K, Xia JH, Chem. Rev., 101(9), 2921 (2001)
  39. Kamigaito M, Ando T, Sawamoto M, Chem. Rev., 101(12), 3689 (2001)
  40. Wang JS, Matyjaszewski K, Macromolecules, 28(22), 7572 (1995)