Aggregation behavior and solubilization properties of 3-hydroxypiperidinium surfactants


Systematic data on the aggregation behavior of novel 3-hydroxypiperidinium surfactants in aqueous solutions were obtained. The ability of the surfactants to solubilize hydrophobic compounds, including the Orange OT dye and biologically active flavonoid quercetin, was characterized. The maximally achieved limiting content of these substances in micellar solutions of 3-hydroxypiperidinium surfactants is by two to three times higher than that in solutions of their non-functionalized analogs. The solubility of quercetin depends on the pH of the medium, and the highest effect observed on going from water to micellar solutions of the studied surfactants reaches two orders of magnitude.

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  1. 1.

    K. R. Lange, Surfactants: A Practical Handbook, Hanser Publishers, Munich, 1999, 237 pp.

    Google Scholar 

  2. 2.

    Th. F. Tadros, Applied Surfactants: Principles and Application, Wiley-VCH, Weinheim, 2005, 634 pp.

    Google Scholar 

  3. 3.

    D. Myers, Surfactant Science and Technology, John Wiley and Sons, Hoboken, New Jersey 2006, 380 pp.

    Google Scholar 

  4. 4.

    S. Abbott, Surfactant Science. Principles and Practice, DEStech Publishing Inc, Lancaster, Pennsylvania, 2017, 198 pp.

    Google Scholar 

  5. 5.

    V. Pandey, S. Kohli, Crit. Rev. Ther. Drug Carrier Syst., 2018, 35, 99.

    Article  Google Scholar 

  6. 6.

    E. E. Badr, Adv. Appl. Sci Res., 2017, 8, 81.

    CAS  Google Scholar 

  7. 7.

    E. A. Vasilieva, S. S. Lukashenko, A. D. Voloshina, A. S. Strobikina, L. A. Vasileva, L. Y. Zakharova, Russ. Chem. Bull., 2018, 67, 1280.

    CAS  Article  Google Scholar 

  8. 8.

    A. B. Mirgorodskaya, S. S. Lukashenko, E. I. Yatskevich, N. V. Kulik, A. D. Voloshina, D. B. Kudryavtsev, A. R. Panteleeva, V. V. Zobov, L. Ya. Zakharova, A. I. Konovalov, Prot. Met. Phys. Chem. Surf., 2014, 50, 538.

    CAS  Article  Google Scholar 

  9. 9.

    Zh. Zhang, H. Wang, W. Shen, J. Chem. Eng. Data, 2013, 58, 2326.

    CAS  Article  Google Scholar 

  10. 10.

    W.-Sh. Liu, Ch.-H. Wang, J.-F. Sun, G.-G. Hou, Y.-P. Wang, R.-J. Qu, Chem. Biol. Drug Des., 2015, 85, 91.

    CAS  Article  Google Scholar 

  11. 11.

    E. I. Yackevich, A. B. Mirgorodskaya, S. S. Lukashenko, L. Ya. Zakharova, Russ. Chem. Bull., 2014, 63, 1801.

    CAS  Article  Google Scholar 

  12. 12.

    A. B. Mirgorodskaya, F. G. Valeeva, S. S. Lukashenko, T. M. Prokopieva, T. M. Zubareva, V. A. Mikhailov, L. Y. Zakharova, J. Mol. Liq., 2018, 250, 229.

    CAS  Article  Google Scholar 

  13. 13.

    O. Kaczerewska, B. Brycki, I. Ribosa, F. Comelles, M. T. Garcia, J. Ind. Eng. Chem., 2018, 59, 141.

    CAS  Article  Google Scholar 

  14. 14.

    V. L. Klimova, Osnovnye mikrometody analiza organicheskikh soedinenii [The Main Methods for Analysis of Organic Compounds], Khimiya, Moscow, 1974, 224 pp. (in Russian).

    Google Scholar 

  15. 15.

    Yu. Zhao, X. Yue, X. Wang, D. Huang, X. Chen, Colloids Surf., A, 2012, 412, 90.

    CAS  Article  Google Scholar 

  16. 16.

    A. I. Rusanov, Mitselloobrazovanie v rastvorakh poverkhnostno-aktivnykh veshchestv [Micelle Formation in Solutions of Surfactants], Khimiya, St. Petersburg, 1992, 280 pp. (in Russian).

    Google Scholar 

  17. 17.

    L. Ya. Zakharova, R. R. Kashapov, T. N. Pashirova, A. B. Mirgorodskaya, O. G. Sinyashin, Mendeleev Commun., 2016, 26, 457.

    CAS  Article  Google Scholar 

  18. 18.

    M. Pisárcik, F. Devínsky, M. Pupák, Open Chem., 2015, 13, 922.

    Article  Google Scholar 

  19. 19.

    H. Schott, J. Phys. Chem., 1966, 70, 2966.

    CAS  Article  Google Scholar 

  20. 20.

    M. H. Alimohammadi, S. Javadian, H. Gharibi, A. R. Tehrani Bagha, M. R. Alavijeh, K. Kakaei, J. Chem. Thermodyn., 2011, 43, 1349.

    Article  Google Scholar 

  21. 21.

    A. N. Chebotarev, D. V. Snigur, J. Anal. Chem., 2015, 70, 55.

    CAS  Article  Google Scholar 

  22. 22.

    I. G. Zenkevich, A. Yu. Eshchenko, S. V. Makarova, A. G. Vitenberg, Yu. G. Dobryakov, V. A. Utsal, Molecules, 2007, 12

    Google Scholar 

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Correspondence to A. B. Mirgorodskaya.

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Dedicated to Academician of the Russian Academy of Sciences A. I. Konovalov on the occasion of his 85th birthday.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 2, pp. 0328–0333, February, 2019.

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Mirgorodskaya, A.B., Kushnazarova, R.A., Lukashenko, S.S. et al. Aggregation behavior and solubilization properties of 3-hydroxypiperidinium surfactants. Russ Chem Bull 68, 328–333 (2019).

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Key words

  • surfactants
  • aggregation
  • solubilization
  • drugs