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Synthesis, Molecular, and Gas-Transport Properties of Homopolymers Based on 5-Ethylidene-2-norbornene and 5-Vinyl-2-norbornene

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Abstract—

Using the commercial derivative of norbornene—5-ethylidene-2-norbornene—a series of three isomeric homopolymers with different structure of the backbone is synthesized, and the effect of the chain structure on the gas-transport behavior of polynorbornenes is studied. The gas-transport characteristics of the polymers are presented together with data on the conformation properties of molecules of addition and metathesis polynorbornenes. The effect of the structure of side substituents on the equilibrium rigidity of addition polynorbornenes is confirmed by the example of poly(5-ethylidene-2-norbornene) and poly(5-vinyl-2-norbornene).

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Notes

  1. Static light scattering and refractive index increments were measured using equipment of the Resource Center for Diagnostics of Functional Materials for Medicine, Pharmacology, and Nanoelectronics, St. Petersburg State University.

REFERENCES

  1. M. V. Bermeshev and P. P. Chapala, Prog. Polym. Sci. 84, 1 (2018).

    Article  CAS  Google Scholar 

  2. M. S. Trimmer, in Handbook of Metathesis, Ed. by R. R. Schrock (Wiley-VCH, Weinheim, 2008), p. 407.

    Google Scholar 

  3. N. G. Gaylord, A. B. Deshpande, B. M. Mandal, and M. Martan, J. Macromol. Sci., Chem. 11, 1053 (1977).

    Article  Google Scholar 

  4. M. V. Bermeshev, B. A. Bulgakov, A. M. Genaev, J. V. Kostina, G. N. Bondarenko, and E. S. Finkelshtein, Macromolecules 47, 5470 (2014).

    Article  CAS  Google Scholar 

  5. G. Khanarian and H. Celanese, Opt. Eng. 40, 1024 (2001).

    Article  CAS  Google Scholar 

  6. V. I. Bykov, K. L. Makovetskii, D. S. Popov, M. V. Bermeshev, T. A. Butenko, M. P. Filatova, and E. S. Finkel’shtein, Polym. Sci., Ser. B 54, 99 (2012).

    Article  CAS  Google Scholar 

  7. V. I. Bykov, K. L. Makovetskii, D. S. Popov, M. V. Bermeshev, T. A. Butenko, and Y. A. Talyzenkov, Dokl. Chem. 439, 227 (2011).

    Article  CAS  Google Scholar 

  8. D. Shamiryan, T. Abell, F. Iacopi, and K. Maex, Mater. Today 7, 34 (2004).

    Article  CAS  Google Scholar 

  9. N. R. Grove, P. A. Kohl, AllenS. A. Bidstrup, S. Jayaraman, and R. Shick, J. Polym. Sci., Part B: Polym. Phys. 37, 3003 (1999).

    Article  CAS  Google Scholar 

  10. A. A. Shutova, A. N. Trusov, M. V. Bermeshev, S. A. Legkov, M. L. Gringolts, E. S. Finkelstein, G. N. Bondarenko, and A. V. Volkov, Oil Gas Sci. Technol. 69, 1059 (2014).

    Article  Google Scholar 

  11. F. Blank and C. Janiak, Coord. Chem. Rev. 253, 827 (2009).

    Article  CAS  Google Scholar 

  12. P. Chapala, M. Bermeshev, L. Starannikova, V. Shantarovich, N. Gavrilova, V. Lakhtin, Y. Yampolskii, and E. Finkelshtein, Macromol. Chem. Phys. 218 (2017). https://doi.org/10.1002/macp.201600385

  13. B. J. Sundell, IiiJ. A. Lawrence, D. J. Harrigan, J. T. Vaughn, T. S. Pilyugina, and D. R. Smith, RSC Adv. 6, 51619 (2016).

    Article  CAS  Google Scholar 

  14. D. A. Alentiev, E. S. Egorova, M. V. Bermeshev, L. E. Starannikova, M. A. Topchiy, A. F. Asachenko, P. S. Gribanov, M. S. Nechaev, Y. P. Yampolskii, and E. S. Finkelshtein, J. Mater. Chem. A 6, 19393 (2018).

    Article  CAS  Google Scholar 

  15. K. R. Gmernicki, E. Hong, C. R. Maroon, S. M. Mahurin, A. P. Sokolov, T. Saito, and B. K. Long, ACS Macro Lett. 5, 879 (2016).

    Article  CAS  PubMed  Google Scholar 

  16. B.-G. Kang, D.-G. Kim, and R. A. Register, Macromolecules 51, 3702 (2018).

    Article  CAS  Google Scholar 

  17. D.-G. Kim, T. Takigawa, T. Kashino, O. Burtovyy, A. Bell, and R. A. Register, Chem. Mater. 27, 6791 (2015).

    Article  CAS  Google Scholar 

  18. S. Liu, Y. Chen, X. He, L. Chen, and W. Zhou, J. Appl. Polym. Sci. 121, 1166 (2011).

    Article  CAS  Google Scholar 

  19. F. Pierre, B. Commarieu, A. C. Tavares, and J. Claverie, Polymer 86, 91 (2016).

    Article  CAS  Google Scholar 

  20. J.-C. Daigle, V. Dube-Savoie, A. C. Tavares, and J. P. Claverie, J. Polym. Sci., Part A: Polym. Chem. 51, 2669 (2013).

    Article  CAS  Google Scholar 

  21. U. Okoroanyanwu, T. Shimokawa, J. Byers, and C. G. Willson, Chem. Mater. 10, 3319 (1998).

    Article  CAS  Google Scholar 

  22. H. V. Tran, R. J. Hung, T. Chiba, S. Yamada, T. Mrozek, Y.-T. Hsieh, C. R. Chambers, B. P. Osborn, B. C. Trinque, M. J. Pinnow, S. A. MacDonald, C. G. Willson, D. P. Sanders, E. F. Connor, R. H. Grubbs, and W. Conley, Macromolecules 35, 6539 (2002).

    CAS  Google Scholar 

  23. E. Finkelshtein, M. Gringolts, M. Bermeshev, P. Chapala, and Y. Rogan, “Polynorbornenes,” in Membrane Materials for Gas and Vapor Separation, Ed. by Yu. Yampolskii and E. Finkelstein (Wiley, Chichester, 2017), p. 143.

    Google Scholar 

  24. E. S. Finkelshtein, M. V. Bermeshev, M. L. Gringolts, L. E. Starannikova, and Y. P. Yampolskii, Russ. Chem. Rev. 80, 341 (2011).

    Article  CAS  Google Scholar 

  25. J. P. Kennedy and J. A. Hinlicky, Polymer 6, 133 (1965).

    Article  CAS  Google Scholar 

  26. N. Tunoglu and N. Balcioglu, Macromol. Rapid Commun. 20, 546 (1999).

    Article  CAS  Google Scholar 

  27. M. V. Bermeshev, B. A. Bulgakov, and E. S. Finkel’shtein, Dokl. Chem. 449, 83 (2013).

    Article  CAS  Google Scholar 

  28. E. L. Kolychev, A. F. Asachenko, P. B. Dzhevakov, A. A. Bush, V. V. Shuntikov, V. N. Khrustalev, and M. S. Nechaev, Dalton Trans. 42, 6859 (2013).

    Article  CAS  PubMed  Google Scholar 

  29. M. Macchione, J. C. Jansen, G. De Luca, E. Tocci, M. Longeri, and E. Drioli, Polymer 48, 2619 (2007).

    Article  CAS  Google Scholar 

  30. B. Chu, Laser Light Scattering: Basic Principles and Practice (Dover Publ. Inc., Mineola; New York, 2007).

  31. W.-M. Kulicke and C. Clasen, Viscosimetry of Polymers and Polyelectrolytes (Springer, Berlin-Heidelberg, 2004).

    Book  Google Scholar 

  32. G. O. Karpov, E. V. Bermesheva, A. V. Zudina, A. F. Asachenko, L. I. Minaeva, M. A. Topchiy, P. S. Gribanov, M. S. Nechaev, and M. V. Bermeshev, Dokl. Chem. 479, 49 (2018).

    Article  CAS  Google Scholar 

  33. K. Endo, K. Fujii, and T. Otsu, Macromol. Chem. Phys. 197, 97 (1996).

    Article  CAS  Google Scholar 

  34. A. D. Hennis, J. D. Polley, G. S. Long, A. Sen, D. Yandulov, J. Lipian, G. M. Benedikt, L. F. Rhodes, and J. Huffman, Organometallics 20, 2802 (2001).

    Article  CAS  Google Scholar 

  35. B. Commarieu, J. Potier, M. Compaore, S. Dessureault, B. L. Goodall, X. Li, and J. P. Claverie, Macromolecules 49, 920 (2016).

    Article  CAS  Google Scholar 

  36. C.-T. Zhao, RibeiroM. Rosario, and M. F. Portela, J. Mol. Catal. A: Chem. 185 (1–2), 81 (2002).

    Article  CAS  Google Scholar 

  37. J. P. Kennedy and H. S. Makowski, J. Macromol. Sci., Chem. 1, 345 (1967).

    Article  CAS  Google Scholar 

  38. F. Blank, H. Scherer, and C. Janiak, J. Mol. Catal. A: Chem. 330, 1 (2010).

    Article  CAS  Google Scholar 

  39. L. Wang, X. Wang, M. Yang, Y. Wang, L. Li, B. Liu, and I. Kim, Macromol. Res. 19, 1071 (2011).

    Article  CAS  Google Scholar 

  40. D. A. Alentiev, S. A. Korchagina, E. S. Finkel’shtein, M. S. Nechaev, A. F. Asachenko, M. A. Topchiy, P. S. Gribanov, and M. V. Bermeshev, Russ. Chem. Bull. 67, 121 (2018).

    Article  CAS  Google Scholar 

  41. P. P. Chapala, I. L. Borisov, M. V. Bermeshev, V. V. Volkov, and E. S. Finkelshtein, Pet. Chem. 56, 1056 (2016).

    Article  CAS  Google Scholar 

  42. G. C. Vougioukalakis and R. H. Grubbs, Chem. Rev. (Washington, DC, U. S.) 110, 1746 (2010).

    Article  CAS  Google Scholar 

  43. R. R. Schrock, Handbook of Metathesis (Wiley-VCH, Weinheim, 2008).

    Google Scholar 

  44. K. Szwaczko, I. Czeluśniak, and K. Grela, J. Organomet. Chem. 847, 146 (2017).

    Article  CAS  Google Scholar 

  45. H. Balcar, T. Shinde, M. Lamač, J. Sedláček, and J. Zedník, J. Polym. Res 21, 557 (2014).

    Article  CAS  Google Scholar 

  46. J. Hakala, M. M. Hänninen, and A. Lehtonen, Inorg. Chem. Commun. 14, 1362 (2011).

    Article  CAS  Google Scholar 

  47. N. P. Yevlampieva, M. V. Bermeshev, A. V. Komolkin, O. S. Vezo, P. P. Chapala, and Y. V. Il’yasova, Polym. Sci., Ser. A 59, 473 (2017).

    Article  CAS  Google Scholar 

  48. N. P. Yevlampieva, M. V. Bermeshev, O. S. Vezo, P. P. Chapala, and Y. V. Il’yasova, Polym. Sci., Ser. A 60, 162 (2018).

    Article  CAS  Google Scholar 

  49. N. P. Yevlampieva, M. V. Bermeshev, A. S. Gubarev, P. P. Chapala, and M. A. Antipov, Polym. Sci., Ser. A 58, 324 (2016).

    Article  CAS  Google Scholar 

  50. H. Fujita, Polymer Solutions (Elsevier, Amsterdam, 1990).

    Google Scholar 

  51. N. P. Yevlampieva, M. L. Gringol’ts, I. I. Zaitseva, and E. I. Ryumtsev, Polym. Sci., Ser. C 52, 83 (2010).

    Article  Google Scholar 

  52. N. A. Belov, M. L. Gringol’ts, A. A. Morontsev, L. E. Starannikova, Y. P. Yampolskii, and E. S. Finkelstein, Polym. Sci., Ser. B 59, 560 (2017).

    Article  CAS  Google Scholar 

  53. E. S. Finkelshtein, K. L. Makovetskii, M. L. Gringolts, Y. V. Rogan, T. G. Golenko, L. E. Starannikova, Y. P. Yampolskii, V. P. Shantarovich, and T. Suzuki, Macromolecules 39, 7022 (2006).

    Article  CAS  Google Scholar 

  54. N. P. Yevlampieva, I. I. Zaitseva, M. L. Gringolts, P. P. Khlyabich, Y. V. Rogan, and E. I. Ryumtsev, Polym. Sci., Ser. A 50, 1082 (2008).

    Article  Google Scholar 

  55. N. Yevlampieva, M. Bermeshev, O. Vezo, P. Chapala, and Y. Il’yasova, J. Polym. Res. 25, article 162 (2018).

    Article  CAS  Google Scholar 

  56. W. Dujardin, C. Van Goethem, J. A. Steele, M. Roeffaers, I. F. J. Vankelecom, and G. Koeckelberghs, Polymers 11(4), 704 (2019).

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Funding

The study of the addition polymerization of bifunctional norbornenes and the characterization of the synthesized polymers were supported by the Russian Science Foundation (project no. 17-19-01595). Metathesis polymerization of 5-vinyl-2-norbornene and the study of properties of polymers based on it was carried out within the framework of the state task for the Topchiev Institute of Petrochemical Synthesis, Russian Academy of Sciences.

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Authors and Affiliations

  1. Topchiev Institute of Petrochemical Synthesis, Russian Academy of Sciences, 119991, Moscow, Russia

    E. V. Bermesheva, A. I. Wozniak, I. L. Borisov, G. O. Karpov, M. V. Bermeshev, A. F. Asachenko, M. A. Topchiy, P. S. Gribanov, M. S. Nechaev, V. V. Volkov & E. Sh. Finkelshtein

  2. Sechenov Moscow State Medical University, 119991, Moscow, Russia

    E. V. Bermesheva

  3. St. Petersburg State University, 198504, St. Petersburg, Russia

    N. P. Yevlampieva & O. S. Vezo

  4. Faculty of Chemistry, Moscow State University, 119991, Moscow, Russia

    M. S. Nechaev

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  1. E. V. Bermesheva
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  2. A. I. Wozniak
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  3. I. L. Borisov
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  4. N. P. Yevlampieva
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  6. G. O. Karpov
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  7. M. V. Bermeshev
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  8. A. F. Asachenko
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  10. P. S. Gribanov
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  12. V. V. Volkov
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  13. E. Sh. Finkelshtein
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Correspondence to M. V. Bermeshev.

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Translated by T. Soboleva

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Bermesheva, E.V., Wozniak, A.I., Borisov, I.L. et al. Synthesis, Molecular, and Gas-Transport Properties of Homopolymers Based on 5-Ethylidene-2-norbornene and 5-Vinyl-2-norbornene. Polym. Sci. Ser. C 61, 86–101 (2019). https://doi.org/10.1134/S181123821901003X

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  • DOI: https://doi.org/10.1134/S181123821901003X

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