Abstract
Chemical modification of polyethylene glycols by antioxidants belonging to the class of sterically hindered phenols is used to obtain water-soluble conjugates differing in the structure of the joined antioxidant and molecular weight. The inclusion of hydrophobic end groups in polyethylene glycol molecules leads to a decrease in the lower critical mixing point of the solution as compared to the original polymer. Dilute solution viscometry and light scattering are used to determine the molecular-mass characteristics of the polymers and the hydrodynamic radii of single conjugate molecules. The mass fraction of single molecules in aqueous solutions of the conjugates is greater than 95%. The aggregates are micellar-type particles whose core is formed by the hydrophobic moieties of sterically hindered phenols. It is shown that the antiradical activity of the antioxidants 3-(3-tert-butyl-4-hydroxy-5-methylphenyl)-propionic acid and 3- (3,5-di-tert-butyl-4-hydroxyphenyl)-propionic acid, which are used for the modification, differs only slightly, whereas the activity of the relevant conjugates increases significantly.
Similar content being viewed by others
References
Burlakova E.B. (ed.), in: Chemical and Biological Kinetics. New Horizons. Biological Kinetics [in Russian], vol. 2, Khimiya, Moscow (2005).
V. V. Korshak and M. I. Shtil’man, Polymers in the Processes of Immobilization and Modification of Natural Compounds [in Russian], Nauka, Moscow (1984).
D. V. Arefiev, I. S. Belostotskaya, V. B. Vol’eva, et al., Izv. Akad. Nauk, Ser. Khim., No. 4, 751 (2007).
S. K. Filippov, A. S. Komolov, O. Yu. Sergeeva, et al., Vysokomol. Soedin., Ser. A, 51, No. 2, 209 (2009).
S. Filippov, A. Lezov, O. Sergeeva, et al., Eur. Polym. J. 44, No. 10, 3361 (2008).
N. S, Domnina D. V. Arefiev, E. A. Komarova, and A. Yu. Bilibin, Macromol. Symp., 144, No. 1, 339 (1999).
N. S. Domnina, O. Yu. Sergeeva, A. N. Vil’bitskaya, et al., Vysokomol. Soedin., Ser. A, 52, No. 9, 1570 (2010).
D. V. Arefiev, N. S. Domnina, E. A. Komarova, et al., Zh. Prikl. Khim., 72, No. 4, 670 (1999).
H. Z. Cummins and E. R. Pike, Photon Correlation and Light Beating Spectroscopy, Plenum, New York (1974).
V. A. Rabinovich and Z. Ya. Khavin, A Brief Chemical Handbook [in Russian], Khimiya, Leningrad (1978).
V. N. Tsvetkov, V. E. Éskin, and S. Ya. Frenkel’, Structure of Macromolecules in Solutions [in Russian], Nauka, Moscow (1964).
A. A. Tager, S. A. Vshivkov, V. M. Andreeva, and T. V. Sekacheva, Vysokomol. Soedin., Ser. A, 16, No. 1, 9 (1974).
G. N. Malkolm and J. S. Rowlinson, Trans. Faraday Soc., 53, 921 (1957).
I. V. Blagodatskikh, O. V. Vasil’eva, S. V. Bykov, et al., Vysokomol. Soedin., Ser. A, 45, No. 10, 1749 (2003).
V. V. Ershov, G. A. Nikiforov, and A. A. Volod’kin, Sterically Hindered Phenols [in Russian], Khimiya, Moscow (1972).
D. V. Arefiev, N. S. Domnina, E. A, Komarova, and A. Yu. Bilibin, Eur. Polym. J., 36, 857 (2000).
Yasushi Maeda, Noriaki Tsukida, Hiromi Kitano, et al., J. Phys. Chem., 97, 13903 (1993).
Author information
Authors and Affiliations
Corresponding author
Additional information
Original Russian Text Copyright © 2011 by L. A. Dobrun, E. L. Kuzyakina, O. V. Rakitina, O. Yu. Sergeeva, M. E. Mikhailova, N. S. Domnina, and A. V. Lezov
__________
Translated from Zhurnal Strukturnoi Khimii, Vol. 52, No. 6, pp. 1197–1202, November–December, 2011.
Rights and permissions
About this article
Cite this article
Dobrun, L.A., Kuzyakina, E.L., Rakitina, O.V. et al. Molecular characteristics and antioxidant activity of polyethylene glycols modified by sterically hindered phenols. J Struct Chem 52, 1161–1166 (2011). https://doi.org/10.1134/S0022476611060229
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S0022476611060229