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Nitroxyl radicals of the imidazoline series as agents of pseudoliving polymerization of styrene

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Abstract

Radical polymerization of styrene in the presence of 2,2,4,5,5-pentamethyl-2,5-dihydro- Imidazol-1-oxyl, 2,2-diethyl-4,5,5-trimethyl-2,5-dihydroimidazol-1-oxyl, 2,2,5,5-tetramethyl- 4-phenyl-2,5-dihydroimidazol-1-oxyl, 2,2,5-trimethyl-4,5-diphenyl-2,5-dihydroimidazol- 1-oxyl, and 2-methyl-2,3-diphenyl-1,4-diazaspiro[4.5]deca-3-en-1-oxyl was studied. Effect of substituents in the nitroxyl radical and the nature of initiator on the features of “pseudoliving” polymerization and the molecular-weight characteristics of polystyrene synthesized were considered. Nitroxyl radicals of imidazoline series, like TEMPO and its derivatives, allow one to regulate polymerization of styrene and obtain polymers with relatively low values of polydispersity index.

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References

  1. G. V. Korolev, A. P. Marchenko, Usp. Khim., 2000, 69, 447 [Russ. Chem. Rev. (Engl. Transl.), 2000, 69].

    Google Scholar 

  2. M. Yu. Zaremskii, V. B. Golubev, Vysokomolekulyar. Soedin., Ser. C, 2001, 43, 1689 [Polym. Sci., Ser. C (Engl. Transl.), 2000, 43].

    CAS  Google Scholar 

  3. D. F. Grishin, L. L. Semenycheva, Usp. Khim., 2001, 70, 486 [Russ. Chem. Rev. (Engl. Transl.), 2001, 70].

    Google Scholar 

  4. K. Matyjaszewski, T. P. Davis, Handbook of Radical Poly- merization, Wiley-Interscience, Hoboken, 2002, 920 pp.

    Book  Google Scholar 

  5. H. Fischer, Chem. Rev., 2001, 101, 3581.

    Article  CAS  Google Scholar 

  6. W. A. Braunecker, K. Matyjaszewski, Prog. Polym. Sci., 2007, 32, 93.

    Article  CAS  Google Scholar 

  7. Y. Miura, N. Nakamura, I. Taniguchi, Macromolecules, 2001, 34, 447.

    Article  CAS  Google Scholar 

  8. Y. Miura, N. Nakamura, I. Taniguchi, A. Ichikawa, Poly-mer, 2003, 44, 3461.

    CAS  Google Scholar 

  9. Y. Miura, A. Ichikawa, I. Taniguchi, Polymer, 2003, 44, 5187.

    Article  CAS  Google Scholar 

  10. Md. A. Mannan, A. Ichikawa, Y. Miura, Polymer, 2007, 48, 743.

    Article  CAS  Google Scholar 

  11. C. A. Knoop, A. Studer, J. Am. Chem. Soc., 2003, 125, 16327.

    Article  CAS  Google Scholar 

  12. K. O. Siegenthaler, A. Studer, Macromolecules, 2006, 39, 1347.

    Article  CAS  Google Scholar 

  13. S. Grimaldi, J. P. Finet, F. le Moigne, A. Zeghdaoui, P. Tordo, D. Benoit, M. Fontanille, Y. Gnanou, Macro-molecules, 2000, 33, 1141.

    CAS  Google Scholar 

  14. D. Benoit, S. Grimaldi, S. Robin, J. P. Finet, P. Tordo, Y. Gnanou, J. Am. Chem. Soc., 2000, 122, 5929.

    Article  CAS  Google Scholar 

  15. A. Debuigne, D. Chang-Seng, L. Lichun, G. K. Hamer, M. K. Georges, Macromolecules, 2007, 40, 6224.

    Article  CAS  Google Scholar 

  16. J. Ruehl, N. L. Hill, E. D. Walter, G. Millhauser, R. Braslau, Macromolecules, 2008, 41, 1972.

    Article  CAS  Google Scholar 

  17. D. F. Grishin, L. L. Semenycheva, E. V. Kolyakina, Dokl. Akad. Nauk, 1998, 362, 634 [Dokl. Chem. (Engl. Transl.), 1998, 362].

    CAS  Google Scholar 

  18. D. F. Grishin, L. L. Semyonycheva, E. V. Kolyakina, Mendeleev Commun., 1999, 250.

  19. E. V. Kolyakina, D. F. Grishin, Usp. Khim., 2009, 78, 579 [Russ. Chem. Rev. (Engl. Transl.), 2009, 78].

    Google Scholar 

  20. M. Yu. Zaremskii, A. P. Orlova, E. S. Garina, A. V. Olenin, M. B. Lachinov, V. B. Golubev, Vysokomolekulyar. Soedin., Ser. A, 2003, 45, 871 [Polym. Sci., Ser. C (Engl. Transl.), 2003, 45].

    CAS  Google Scholar 

  21. C. Detrembleur, V. Sciannamea, C. Koulic, M. Claes, M. Hoebeke, R. Jerome, Macromolecules, 2002, 35, 7214.

    Article  CAS  Google Scholar 

  22. V. Sciannamea, R. Jérôme, C. Detrembleur, Chem. Rev., 2008, 108, 1104.

    Article  CAS  Google Scholar 

  23. E. H. H. Wong, M. H. Stenzel, T. Junkers, C. Barner-Kowollik, J. Polym. Sci., Part A: Polym. Chem., 2009, 47, 1098.

    Article  CAS  Google Scholar 

  24. D. Zubenko, I. Kirilyuk, G. Roshchupkina, I. Zhurko, V. Reznikov, S. Marque, E. G. Bagryanskaya, Helv. Chim. Acta, 2006, 89, 2341.

    Article  CAS  Google Scholar 

  25. M. A. Lazarev, I. A. Kirilyuk, I. A. Grigoŕev, D. F. Grishin, Vysokomolekulyar. Soedin., Ser. B, 2007, 49, 1735 [Polym. Sci., Ser. B (Engl. Transl.), 2000, 49].

    CAS  Google Scholar 

  26. M. V. Pavlovskaya, I. A. Kirilyuk, A. A. Shchepalov, I. A. Grigoŕev, D. F. Grishin, Vysokomolekulyar. Soedin., Ser. B, 2008, 50, 2181 [Polym. Sci., Ser. B (Engl. Transl.), 2000, 50].

    CAS  Google Scholar 

  27. J. P. van Hook, A. V. J. Tobolsky, J. Am. Chem. Soc., 1958, 80, 779.

    Article  Google Scholar 

  28. B. Barnett, W. E. Vaughan, J. Phys. Chem., 1947, 51, 926.

    Article  CAS  Google Scholar 

  29. F. J. Hua, Y. L. Yang, Polymer, 2001, 42, 1361.

    Article  CAS  Google Scholar 

  30. K. Matyjaszewski, T. Shigemoto, J. M. J. Frechet, M. Leduc, Macromolecules, 1996, 29, 4167.

    Article  CAS  Google Scholar 

  31. A. Goto, T. Fukuda, Prog. Polym. Sci., 2004, 29, 329.

    Article  CAS  Google Scholar 

  32. D. P. Zubenko, Ph.D. Thesis (Chem.), International Tomographic Center SB RAS, Novosibirsk, 2008, 119 pp. (in Russian).

    Google Scholar 

  33. H. Fischer, A. Kramer, S. R. A. Marque, P. Nesvadba, Macromolecules, 2005, 38, 9974.

    Article  CAS  Google Scholar 

  34. G. S. Ananchenko, H. Fischer, J. Polym. Sci., Part A: Polym. Chem., 2001, 39, 3604.

    Article  CAS  Google Scholar 

  35. D. Benoit, V. Chaplinski, R. Braslau, C. J. Hawker, J. Am. Chem. Soc., 1999, 121, 3904.

    Article  CAS  Google Scholar 

  36. A. Studer, K. Harms, Ch. Knoop, Ch. Muller, T. Schulte, Macromolecules, 2004, 37, 27.

    Article  CAS  Google Scholar 

  37. M. Souaille, H. Fischer, Macromolecules, 2002, 35, 248.

    Article  CAS  Google Scholar 

  38. M. Buback, R. G. Gilbert, R. A. Hutchinson, B. Klumperman, F.-D. Kuchta, B. G. Manders, K. F. ÓDriscoll, G. T. Russell, J. Schweer, Macromol. Chem. Phys., 1995, 169, 3267.

    Article  Google Scholar 

  39. F. Chauvin, P.-E. Dufils, D. Gigmes, Y. Guillaneuf, S. R. A. Marque, P. Tordo, D. Bertin, Macromolecules, 2006, 39, 5238.

    Article  CAS  Google Scholar 

  40. G. V. Korolev, G. M. Bakova, M. P. Berezin, Vysokomole-kulyar. Soedin., Ser. A, 2001, 43, 405 [Polym. Sci., Ser. A (Engl. Transl.), 2000, 43].

    CAS  Google Scholar 

  41. A. Weissberger, E. Proskauer, J. Riddick, E. Toops, Organic Solvents, Interscience Publishers, INC, New York, 1955.

    Google Scholar 

  42. Organic Syntheses, Third Printing, Interscience Publishers, New York—London, 1946–1952, 26–32.

  43. Entsiklopediya polimerov [Encyclopedia of Polymers], Sovetskaya Entsiklopediya, Moscow, 1972, 1, 1224 pp. (in Russian).

  44. L. B. Volodarskii, V. A. Reznikov, V. S. Kobrin, Zh. Org. Khim., 1979, 13, 415 [J. Org. Chem. USSR (Engl. Transl.), 1979, 13].

    Google Scholar 

  45. D. Zubenko, Y. Tsentalovich, N. Lebedeva, I. Kirilyuk, G. Roshchupkina, I. Zhurko, V. Reznikov, S. R. A. Marque, E. Bagryanskaya, J. Org. Chem., 2006, 71, 6044.

    Article  CAS  Google Scholar 

  46. T. K. Sevast’yanova, L. B. Volodarskii, Izv. Akad. Nauk SSSR, Ser. Khim., 1972, 2339 [Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.), 1972, 31, 2276].

  47. I. A. Kirilyuk, I. A. Grigoŕev, L. B. Volodarskii, Izv. Akad. Nauk SSSR, Ser. Khim., 1991, 2113 [Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.), 1991, 40, 1871].

    Google Scholar 

  48. L. B. Volodarskii, A. N. Lysak, V. A. Koptyug, Khim. Geterotsikl. Soedin., 1968, 334 [Chem. Heterocycl. Compd. (Engl. Transl.), 1968].

  49. B. G. Beleńkii, L. Z. Vilenchik, Khromatografiya polimerov [Chromatography of Polymers], Moscow, Khimiya, 1978, 344 pp. (in Russian).

    Google Scholar 

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Correspondence to D. F. Grishin.

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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 8, pp. 1519–1527, August, 2010.

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Kolyakina, E.V., Lazarev, M.A., Pavlovskaya, M.V. et al. Nitroxyl radicals of the imidazoline series as agents of pseudoliving polymerization of styrene. Russ Chem Bull 59, 1556–1564 (2010). https://doi.org/10.1007/s11172-010-0278-x

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  • DOI: https://doi.org/10.1007/s11172-010-0278-x

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