Skip to main content
SpringerLink
Log in

Cross-Metathesis between Polynorbornene and Poly(5,6-epoxy-1-octenamer)

  • Published:
Polymer Science, Series C Aims and scope Submit manuscript

Abstract

The macromolecular reaction of interchain cross-metathesis between polynorbornene and poly(5,6-epoxy-1-octenamer) in the presence of the first-generation Grubbs catalyst is studied. Chemically stable poly(5,6-epoxy-1-octenamer) is obtained through metathesis polymerization of 5,6-epoxycyclooct-1-ene with the second-generation Grubbs ruthenium catalyst. New random multiblock copolymers of norbornene and 5,6-epoxycyclooct-1-ene with different average block lengths determined by the reaction time, solvent type, and concentrations of the catalyst and initial homopolymers are synthesized and characterized by NMR, GPC, and DSC. Despite a distance between the epoxy substituent and the reaction center (double bond), poly(5,6-epoxy-1-octenamer) shows a lower activity in the cross-metathesis reaction with polynorbornene compared to unsubstituted polyoctenamer. The influence of epoxy groups present in the backbones of homopolymer and norbornene–cyclooctene multiblock copolymers on their thermal characteristics is studied. It is shown that the glass transition and melting temperatures increase with the concentration of epoxy groups upon the incorporation of an oxirane fragment into both homopolymers and copolymers. The crystallinity of poly(5,6-epoxy-1-octenamer) increases with the content of trans-С=С bonds in the polymer.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1.
Fig. 2.

Similar content being viewed by others

REFERENCES

  1. Olefin Metathesis and Metathesis Polymerization, Ed. by K. J. Ivin and J. C. Mol (Acad. Press, San Diego, 1997).

    Google Scholar 

  2. H. Otsuka, T. Muta, M. Sakada, T. Maeda, and A. Takahara, Chem. Commun. 2009, 1073 (2009).

    Article  Google Scholar 

  3. T. Maeda, S. Kamimura, T. Ohishi, A. Takahara, and H. Otsuka, Polymer 55, 6245 (2014).

    Article  CAS  Google Scholar 

  4. T. Ohishi, K. Suyama, S. Kamimura, M. S. K. Imato, S. Kawahara, A. Takahara, and H. Otsuka, Polymer 78, 145 (2015).

    Article  CAS  Google Scholar 

  5. S. Daniele, A. Mariconda, G. Guerra, P. Longo, and L. Giannin, Polymer 130, 143 (2017).

    Article  CAS  Google Scholar 

  6. M. R. Radlauer, M. E. Matta, and M. A. Hillmyer, Polym. Chem. 7, 6269 (2016).

    Article  CAS  Google Scholar 

  7. N. L. Wagner, F. J. Timmers, D. J. Arriola, G. Jueptner, and B. G. Landes, Macromol. Rapid Commun. 29, 1438 (2008).

    Article  CAS  Google Scholar 

  8. Yu. I. Denisova, M. L. Gringolts, A. S. Peregudov, L. B. Krentsel, E. A. Litmanovich, A. D. Litmanovich, E. Sh. Finkelshtein, and Y. V. Kudryavtsev, Beilstein J. Org. Chem. 11, 1796 (2015).

    Article  CAS  Google Scholar 

  9. M. L. Gringolts, Yu. I. Denisova, G. A. Shandryuk, L. B. Krentsel, A. D. Litmanovich, E. S. Finkelshtein, and Y. V. Kudryavtsev, RSC Adv. 5, 316 (2015).

  10. Yu. I. Denisova, M. L. Gringolts, L. B. Krentsel’, G. A. Shandryuk, A. D. Litmanovich, E. Sh. Finkelshtein, and Ya. V. Kudryavtsev, Polym. Sci., Ser. B 58, 292 (2016).

    Article  CAS  Google Scholar 

  11. G. A. Shandryuk, Y. I. Denisova, M. L. Gringolts, L. B. Krentsel, A. D. Litmanovich, E. Sh. Finkelshtein, and Y. V. Kudryavtsev, Eur. Polym. J. 86, 143 (2017).

    Article  CAS  Google Scholar 

  12. Yu. I. Denisova, M. L. Gringolts, L. B. Krentsel’, G. A. Shandryuk, A. S. Peregudov, E. Sh. Finkelshtein, and Y. V. Kudryavtsev, Polym. Sci., Ser. B 59, 412 (2017).

    Article  CAS  Google Scholar 

  13. Y. I. Denisova, M. L. Gringolts, A. V. Roenko, G. A. Shandryuk, E. Sh. Finkelshtein, and Y. V. Kudryavtsev, Mendeleev Commun. 27, 416 (2017).

    Article  CAS  Google Scholar 

  14. Yu. I. Denisova, A. V. Roenko, M. L. Gringolts, L. B. Krentsel’, A. S. Peregudov, G. A. Shandryuk, E. Sh. Finkelshtein, and Ya. V. Kudryavtsev, Polym. Sci., Ser. B 60, 735 (2018).

    Article  CAS  Google Scholar 

  15. C. M. Bates and F. S. Bates, Macromolecules 50, 3 (2017).

    Article  CAS  Google Scholar 

  16. Y.-X. Lu, F. Tournilhac, L. Leibler, and Z. Guan, J. Am. Chem. Soc. 134, 8424 (2012).

    Article  CAS  Google Scholar 

  17. C. Descour, T. Macko, I. Schreur-Piet, and M. P. F. Pepels, R. Duchateau, RSC Adv. 5, 9658 (2015).

  18. M. Bornand and P. Chen, Angew. Chem., Int. Ed. 44, 7909 (2005).

    Article  Google Scholar 

  19. N. Naga, G. Kikuchi, and A. Toyota, Polymer 47, 6081 (2006).

    Article  CAS  Google Scholar 

  20. A. J. Ultree, in Encyclopedia of Polymer Science and Engineering, Ed. by J. I. Kroschwitz (John Wiley and Sons, New York; Chichester, 1986), Vol. 6, p. 733.

    Google Scholar 

  21. J. E. Bolick and A. W. Jensen, in Kirk-Othmer Encyclopedia of Chemical Technology, Ed. by M. Howe-Grant (Wiley, New York, 1993), Vol. 10, p. 624.

    Google Scholar 

  22. A. G. Margaritis and N. K. Kalfoglou, Polym. J. 24, 1043 (1988).

    CAS  Google Scholar 

  23. K. Wang, G. Zhu, Y. Wang, and F. Ren, J. Appl. Polym. Sci. 132, 42045 (2015).

    Google Scholar 

  24. J. Karger-Kocsis and S. Kéki, Polymers 10, 34 (2018).

    Article  Google Scholar 

  25. U.S. Patent No. 4859746 (1989).

  26. A. A. Morontsev, M. L. Gringolts, M. P. Filatova, and E. Sh. Finkelshtein, Polym. Sci., Ser. B 58, 695 (2016).

    Article  CAS  Google Scholar 

  27. T. J. Boyd and R. R. Schrock, Macromolecules 32, 6608 (1999).

    Article  CAS  Google Scholar 

  28. N. A. Belov, M. L. Gringolts, A. A. Morontsev, L. E. Starannikova, Yu. P. Yampolskii, and E. Sh. Finkelstein, Polym. Sci., Ser. B 59, 560 (2017).

    Article  CAS  Google Scholar 

  29. A. A. Morontsev, V. A. Zhigarev, R. Yu. Nikiforov, N. A. Belov, M. L. Gringolts, E. Sh. Finkelshtein, and Yu. P. Yampolskii, Eur. Polym. J. 99, 340 (2018).

    Article  CAS  Google Scholar 

  30. A. Muhlebach, P. A. van der Schaaf, and A. Hafner, “New Materials from Thermal and Photoinduced Ring Opening Metathesis Polymerisation (ROMP/PROMP),” in Ring Opening Metathesis Polymerisation and Related Chemistry, Ed. by E. Khosvari and T. Szymanska-Buzar (Springer, Dordrecht, 2002).

    Google Scholar 

  31. A. A. Morontsev, Yu. I. Denisova, M. L. Gringolts, M. P. Filatova, G. A. Shandryuk, E. Sh. Finkel’shtein, and Ya. V. Kudryavtsev, Polym. Sci., Ser. B 60, 688 (2018).

    Article  CAS  Google Scholar 

  32. A. Demonceau, A. W. Stumpf, E. Saive, and A. F. Noels, Macromolecules 30, 3127 (1997).

    Article  CAS  Google Scholar 

  33. M. A. Hillmyer, W. R. Laredo, and R. H. Grubbs, Macromolecules 28, 6311 (1995).

    Article  CAS  Google Scholar 

  34. A. W. Stumpf, E. Saive, A. Demonceau, and A. F. Noels, J. Chem. Soc., Chem. Commun., No. 11, 1127 (1995).

  35. J. Wang, T. B. Kouznetsova, Z. S. Kean, L. Fan, B. D. Mar, T. J. Martínez, and S. L. Craig, J. Am. Chem. Soc. 136, 15162 (2014).

    Article  CAS  Google Scholar 

  36. S. Nakagawa, T. Tanaka, T. Ishizone, S. Nojima, K. Kamimura, K. Yamaguchi, and S. Nakahama, Polymer 55, 4394 (2014).

    Article  CAS  Google Scholar 

  37. T. R. Panthani and F. S. Bates, Macromolecules 48, 4529 (2015).

    Article  CAS  Google Scholar 

Download references

ACKNOWLEDGMENTS

The authors are grateful to S.A. Korchagina for the GPC analyses. The structure of the obtained compounds was studied using the equipment of the Shared Research Center of the Topchiev Institute of Petrochemical Synthesis, Russian Academy of Sciences and the Center for Molecular Structure Studies of the Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences.

Funding

This work was supported by the Russian Foundation for Basic Research (project no. 16-33-60213), and carried out within the State Program of Topchiev Institute of Petrochemical Synthesis, Russian Academy of Sciences.

Author information

Authors and Affiliations

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

    A. V. Roenko, Yu. I. Denisova, M. L. Gringolts, G. A. Shandryuk, E. Sh. Finkelshtein & Y. V. Kudryavtsev

  2. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 119991, Moscow, Russia

    A. S. Peregudov

Authors
  1. A. V. Roenko
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Yu. I. Denisova
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. M. L. Gringolts
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. A. S. Peregudov
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. G. A. Shandryuk
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. E. Sh. Finkelshtein
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Y. V. Kudryavtsev
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to A. V. Roenko.

Additional information

Translated by L. Tkachenko

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Roenko, A.V., Denisova, Y.I., Gringolts, M.L. et al. Cross-Metathesis between Polynorbornene and Poly(5,6-epoxy-1-octenamer). Polym. Sci. Ser. C 61, 134–144 (2019). https://doi.org/10.1134/S1811238219010156

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1811238219010156

Search

Navigation