Polymer Science Series B

, Volume 56, Issue 6, pp 695–706 | Cite as

Alkenyl-substituted methacrylates as bifunctional monomers in radical polymerization

  • L. A. Vretik
  • E. A. Nikolaeva
  • V. V. Zagniy
  • V. G. Syromyatnikov
Polymerization
  • 56 Downloads

Abstract

This paper addresses the radical polymerization of dimethacryloyl monomers with double bonds of different activities. The preferential selective polymerization via methacrylate groups of bifunctional monomers with phenyl, phenyl benzoate, and biphenyl benzoate aromatic “cores” in the presence of less active methacrylamide double bonds is studied. It is shown that the initiated radical polymerization of the dimethacryloyl monomers in dimethylformamide at small conversions makes it possible to prepare soluble polymeric products containing free methacrylamide-methacrylate groups. The molar ratio of these methacrylamide-methacrylate groups depends on reactivity ratios r 1 and r 2 of the double bonds of different activities in the bifunctional monomers and on the conversions of the monomers.

Keywords

Polymer Science Series Radical Polymerization AIBN Methacrylamide Methacryloyl 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    M. A. Gauthier, M. I. Gibson, and H.-A. Klok, Angew. Chem., Int. Ed. Engl. 48, 48 (2009).CrossRefGoogle Scholar
  2. 2.
    P. Theato, J. Polym. Sci., Part A: Polym. Chem. 46, 6677 (2008).CrossRefGoogle Scholar
  3. 3.
    R. B. Breitenkamp and T. Emrick, Biomacromolecules 9, 2495 (2008).CrossRefGoogle Scholar
  4. 4.
    A. Khan, M. Malkoch, M. F. Montague, and C. J. Hawker, J. Polym. Sci., Part A: Polym. Chem. 46, 6238 (2008).CrossRefGoogle Scholar
  5. 5.
    D. E. Noga, T. A. Petrie, A. Kumar, M. Weck, A. J. Garcia, and D. M. Collard, Biomacromolecules 9, 2056 (2008).CrossRefGoogle Scholar
  6. 6.
    B. Parrish, R. B. Breitenkamp, and T. Emrick, J. Am. Chem. Soc. 127, 7404 (2005).CrossRefGoogle Scholar
  7. 7.
    D. A. Rankin and A. B. Lowe, Macromolecules 41, 614 (2008).CrossRefGoogle Scholar
  8. 8.
    Y. Q. Wang, D. E. Noga, K. Yoon, A. M. Wojtowicz, A. S. P. Lin, A. J. Garcia, D. M. Collard, and M. Weck, Adv. Funct. Mater. 18, 3638 (2008).CrossRefGoogle Scholar
  9. 9.
    L. P. Yang, X. H. Dong, and C. Y. Pan, J. Polym. Sci., Part A: Polym. Chem. 46, 7757 (2008).CrossRefGoogle Scholar
  10. 10.
    D. J. Liaw, C. C. Huang, and S. M. Hong, J. Polym. Sci., Part A: Polym. Chem. 44, 6287 (2006).CrossRefGoogle Scholar
  11. 11.
    A. W. York, S. E. Kirkland, and C. L. McCormick, Adv. Drug Delivery Rev. 60, 1018 (2008).CrossRefGoogle Scholar
  12. 12.
    Chemistry and Technology of UV and EB Formulation for Coatings, Inks and Paints, Vol. 4: Formulation (SITA Technology, London, 1991).Google Scholar
  13. 13.
    J. G. Kloosterboer, Adv. Polym. Sci. 84, 1 (1988).CrossRefGoogle Scholar
  14. 14.
    H. R. Ragin, in Radiation Curing, Science and Technology, Ed. by S. P. Pappas (Plenum Press, New York, London, 1992), p. 462.Google Scholar
  15. 15.
    K. S. Anseth, C. Decker, and C. N. Bowman, Macromolecules 28(8), 4040 (1995).CrossRefGoogle Scholar
  16. 16.
    K. S. Anseth, C. M. Wang, and C. N. Bowman, Macromolecules 27, 650 (1994).CrossRefGoogle Scholar
  17. 17.
    S. Zhu and A. E. Hamielec, Makromol. Chem., Macromol. Symp. 63, 135.Google Scholar
  18. 18.
    C. Decker, Material Science and Technology (VCH Verlagsgesellschaft mbH, Weinheim, 1997), Vol. 18, Chap. 13.Google Scholar
  19. 19.
    J. L. Mateo, M. Calvo, J. Serrano, and P. Bosch, Macromolecules 3, 5243 (1999).CrossRefGoogle Scholar
  20. 20.
    S. S. Satav, R. N. Karmalkar, M. G. Kulkarni, M. Nagaraju, and G. N. Sastry, J. Am. Chem. Soc. 128(24), 7752 (2006).CrossRefGoogle Scholar
  21. 21.
    L. Yu. Gryshchuk, L. O. Vretik, and V. G. Syromyatnikov, Mater. Sci. 20(3), P. 5 (2002).Google Scholar
  22. 22.
    L. Yu. Gryshuk, L. O. Vretik, and V. G. Syromyatnikov, Polym. Sci., Ser. A 49(2), 238 (2007).Google Scholar
  23. 23.
    L. Yu. Gryshuk, L. O. Vretik, V. G. Syromyatnikov, O. O. Novikova, L. P. Paskal, V. Yu. Voytekunas, and M. J. M. Abadie, Polym. Int. 53(1), 27 (2004).CrossRefGoogle Scholar
  24. 24.
    L. O. Vretik, V. V. Zagnij, O. A. Nikolaeva, and V. G. Syromyatnikov, Mol. Cryst. Liq. Cryst. 590(1), 211 (2014).CrossRefGoogle Scholar
  25. 25.
    M. Schadt, K. Schmitt, V. Kozinkov, and V. Chigrinov, Jpn. J. Appl. Phys. 31, 2155 (1992).CrossRefGoogle Scholar
  26. 26.
    A. Dyadyusha, V. Kozinkov, T. Marusii, Y. Reznikov, V. Reshetnyak, and A. Khizhnyak, Ukr. Fiz. Zh. 36, 1059 (1991).Google Scholar
  27. 27.
    M. O’Neill and S. M. Kelly, J. Phys. D: Appl. Phys. 33, R67 (2000).CrossRefGoogle Scholar
  28. 28.
    V. Kyrychenko, G. Smolyakov, V. Zagniy, L. Vretik, L. Paskal, V. Syromyatnikov, and O. Yaroshchuk, Mol. Cryst. Liq. Cryst. 496, 278 (2008).CrossRefGoogle Scholar
  29. 29.
    L. O. Vretik, V. G. Syromyatnikov, V. V. Zagniy, E. A. Savchuk, and O. V. Yaroshcuk, Mol. Cryst. Liq. Cryst. 486, 57 (2008).CrossRefGoogle Scholar
  30. 30.
    L. Vretik, V. Kyrychenko, G. Smolyakov, O. Yaroshchuk, V. Zagniy, T. Gavrilko, L. Paskal, and V. Syromyatnikov, Mol. Cryst. Liq. Cryst. 536, 224 (2011).CrossRefGoogle Scholar
  31. 31.
    L. Vretik, O. Yaroshchuk, V. Zagniy, V. Kyrychenko, and V. Syromyatnikov, in Liquid Crystalline Organic Compounds and Polymers as Materials of the XXI Century: From Synthesis to Applications (Transworld Research Network, Trivandrum, Kerala, 2011), p. 153.Google Scholar
  32. 32.
    A. M. Toroptseva, K. V. Belogorodskaya, and V. M. Bondarenko, Laboratory Manual for Chemistry and Engineering of Polymers (Khimiya, Leningrad, 1972) [in Russian].Google Scholar
  33. 33.
    L. P. Paskal’, Candidate’s Dissertation in Chemistry (Kiev National Univ., Kiev, 1984).Google Scholar
  34. 34.
    G. Ham, Copolymerization (Interscience, New York, 1964).Google Scholar
  35. 35.
    E. Yun, L. V. Lobanova, A. D. Litmanovich, N. A. Plate, M. V. Shishkina, and T. A. Polikarpova, Vysokomol. Soedin. 12(11), 2488 (1970).Google Scholar
  36. 36.
    Yu. S. Lipatov, A. E. Nesterov, T. M. Gritsenko, and R. A. Veselovskii, Handbook on Polymer Chemistry (Naukova dumka, Kiev, 1971) [in Russian].Google Scholar
  37. 37.
    L. Hammet, Physical Organic Chemistry: Reaction Rates, Equilibria and Mechanisms, (McGraw-Hill, New York, 1970).Google Scholar
  38. 38.
    A. Yu. Kolendo, Candidate’s Dissertation in Chemistry (Kiev National Univ., Kiev, 1990).Google Scholar
  39. 39.
    L. J. Bellamy, The Infrared Spectra of Complex Molecules (John Wiley & Sons Inc., New York, 1975).CrossRefGoogle Scholar

Copyright information

© Pleiades Publishing, Ltd. 2014

Authors and Affiliations

  • L. A. Vretik
    • 1
  • E. A. Nikolaeva
    • 1
  • V. V. Zagniy
    • 1
  • V. G. Syromyatnikov
    • 1
  1. 1.Faculty of ChemistryShevchenko National UniversityKievUkraine

Personalised recommendations