SpringerLink
Log in

Elastomers Based on Nitrile Butadiene Rubber Stabilized with N-Aryl-substituted Camphan-2 and Fenchan-2-amines

  • TO THE ANNIVERSARY OF ACADEMICIAN I. A. NOVAKOV
  • Published:
Polymer Science, Series B Aims and scope Submit manuscript

Abstract—

For the first time, it was proposed to use aniline derivatives with a skeleton monoterpene fragment at the nitrogen atom (N-(het)aryl-substituted camphan-2-amines and N-aryl-substituted fenchan-2-amines) as antioxidants for rubbers. Using nitrile butadiene rubber as an example, the kinetics of accumulation of carbonyl groups in macromolecules was studied using IR spectroscopy and the potential ability of these compounds to inhibit the process of thermal-oxidative aging was revealed. N-[(1RS,2RS)-Camphan-2-yl]-4-methoxyaniline and N-[(1RS,2RS)-camphan-2-yl]-4-ethoxyaniline, which differ in the presence of polar ethoxy and methoxy substituents at the p-position at aniline and characterized by the lowest bond energy >N–H. The results of a comprehensive assessment of the retention of elastic-strength properties, hardness, and degree of cross-linking of samples after thermal-oxidative aging in laboratory conditions, as well as long-term full-scale climatic tests in the tropical climate of southern Vietnam, allow us to conclude that after additional testing these compounds can be used as antioxidants in rubber formulations.

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

Access this article

Log in via an institution

Subscribe and save

Springer+ Basic
EUR 32.99 /Month
  • Get 10 units per month
  • Download Article/Chapter or Ebook
  • 1 Unit = 1 Article or 1 Chapter
  • Cancel anytime
Subscribe now

Buy Now

Price includes VAT (Germany)

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1.
Fig. 2.
Fig. 3.

Similar content being viewed by others

REFERENCES

  1. R. N. Datta, N. M. Huntink, S. Datta, and A. G. Talma, Rubber Chem. Technol. 80, 436 (2007).

    Article  CAS  Google Scholar 

  2. N. M. Emanuel, Vysokomol. Soed. A 21, 2624 (1979).

    CAS  Google Scholar 

  3. N. N. M. Emanuel and A. L. Buchachenko, Chemical Physics of Polymer Degradation and Stabilization (Utrecht, VSP, 1987).

    Google Scholar 

  4. G. Scott, Rubber Chem. Technol. 58, 269 (1985).

    Article  CAS  Google Scholar 

  5. K. B. Piotrovsky and Z. N. Tarasova, Aging and Stabilizing Synthetic Rubber (Moscow, 1980) [in Russian].

    Google Scholar 

  6. W. Zhao, J. He, P. Yu, X. Jiang, and L. Zhang, Polym. Degrad. Stab. 207, 110223 (2023).

  7. Q. Liu, D. Peng, P. Wei, H. Song, C. Cong, X. Meng, and Q. Zhou, Polym. Degrad. Stab. 218, 110585 (2023).

  8. G. Y. Li and J. L. Koenig, Rubber Chem. Technol. 78, 355 (2005).

    Article  CAS  Google Scholar 

  9. T. Nishiyama, T. Suzuki, Y. Hashiguchi, S. Shiotsu, and M. Fujioka, Polym. Degrad. Stab. 75, 549 (2002).

    Article  CAS  Google Scholar 

  10. T. Yamazaki and T. Seguchi, J. Polym. Sci., Part A: Polym. Chem. 35, 279 (1997).

    Article  CAS  Google Scholar 

  11. E. Klein, M. Matis, V. Lukes, and Z. Cibulkova, Polym. Degrad. Stab. 91, 262 (2006).

    Article  CAS  Google Scholar 

  12. N. S. Allen, E. B. Zeynalov, K. Taylor, and P. Birkett, Polym. Degrad. Stab. 94, 1932 (2009).

    Article  CAS  Google Scholar 

  13. D. J. Carlsson, J. P. T. Jensen, and D. M. Wiles, Makromol. Chem. 8, 79 (1984).

    Article  CAS  Google Scholar 

  14. D. Al-Sammerrai and Z. S. Salih, Thermochim. Acta 88, 461 (1985).

    Article  CAS  Google Scholar 

  15. R. Davand, M. R. Rahimpour, S. Hassanajili, and R. Rashedi, J. Appl. Polym. Sci. 138, 51262 (2021).

    Article  CAS  Google Scholar 

  16. D. G. Lin and E. V. Vorobyova, J. Appl. Polym. Sci. 118, 1430 (2010).

    Article  CAS  Google Scholar 

  17. Y. Sun, J. He, B. Zhong, L. Zhu, F. Liu, Polym. Degrad. Stab. 170, 108999 (2019).

  18. I. N. Svibovich, Kauch. Rez. 6, 15 (1999).

    Google Scholar 

  19. S. Winfield, Patent USA 2,211,629 (1940).

  20. A. A. Vernigora, R. V. Brunilin, V. V. Burmistrov, A. V. Davidenko, M. B. Navrotskii, N. A. Salykin, V. V. Chernyshov, and I. A. Novakov, Dokl. Chem. 512, 260 (2023).

    Article  CAS  Google Scholar 

  21. R. V. Brunilin, A. A. Vernigora, O. V. Vostrikova, A. V. Davidenko, M. B. Navrotskii, N. A. Salykin, I. A. Novakov, Russ. Chem. Bull. 71, 1662 (2022).

    Article  CAS  Google Scholar 

  22. E. da Silva, A. Araújo da Silva, A. Moraes, L. de Souza, M. Silva Lourenço, M. de Souza, J. Wardell, and S. Wardell, Sci. Pharm. 84, 467 (2016).

    Article  CAS  Google Scholar 

  23. O. I. Yarovaya and N. F. Salakhutdinov, Russ. Chem. Rev. 90, 488 (2021).

    Article  Google Scholar 

  24. A. A. Vernigora, D. A. Nilidin, and A. V. Davidenko, Fan Ngok Tu, S. G. Gubin, E. V. Gubina, M. A. Vaniev, and I. A. Novakov, Izv. VolgGTU 5, 47 (2021).

    Google Scholar 

  25. K. Schwetlick and W. D. Habicher, Polym. Degrad. Stab. 78, 35 (2002).

    Article  CAS  Google Scholar 

  26. P. Gijsman, Polym. Degrad. Stab. 145, 2 (2017).

    Article  CAS  Google Scholar 

  27. A. A. Vernigora, A. V. Davidenko, N. A. Salykin, L. L. Brunilina, D. N. Nebykov, S. N. Lavrenov, E. B. Isakova, A. S. Trenin, A. A. Nefedov, V. I. Krasnov, D. N. Polovyanenko, and I. A. Novakov, Russ. Chem. Bull. 73, 168 (2024).

    Article  CAS  Google Scholar 

  28. P. J. Flory and J. Rehner, Jr., J. Chem. Phys. 11, 521 (1943).

    Article  CAS  Google Scholar 

Download references

Funding

The work was supported by the Russian Science Foundation (project 22-13-20062) https://rscf.ru/project/22-13-20062/ and the Administration of the Volgograd Region (agreement No. 2 of June 10, 2022).

Author information

Authors and Affiliations

  1. Volgograd State Technical University, 400005, Volgograd, Russia

    D. A. Nilidin, M. A. Vaniev, A. A. Vernigora, A. V. Davidenko, N. A. Salykin & I. A. Novakov

  2. Institute of Tropical Materials Science, Joint Russian-Vietnamese Tropical Research and Technology Center, Hanoi, Vietnam

    Dang Minh Thuy

  3. Severtsov Institute of Ecology and Evolution Problems, Russian Academy of Sciences, 400005, Volgograd, Russia

    S. G. Gubin

Authors
  1. D. A. Nilidin
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. M. A. Vaniev
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. A. A. Vernigora
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Dang Minh Thuy
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. S. G. Gubin
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. A. V. Davidenko
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. N. A. Salykin
    View author publications

    You can also search for this author in PubMed Google Scholar

  8. I. A. Novakov
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to D. A. Nilidin.

Ethics declarations

The authors of this work declare that they have no conflicts of interest.

Additional information

Translated by V. Avdeeva

Publisher’s Note.

Pleiades Publishing remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Nilidin, D.A., Vaniev, M.A., Vernigora, A.A. et al. Elastomers Based on Nitrile Butadiene Rubber Stabilized with N-Aryl-substituted Camphan-2 and Fenchan-2-amines. Polym. Sci. Ser. B (2024). https://doi.org/10.1134/S1560090424600487

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • DOI: https://doi.org/10.1134/S1560090424600487

Search

Navigation