Abstract
Oligomeric aryloxycyclotriphosphazenes with mixed functional groups are synthesized by the interaction of hexachlorocyclotriphosphazene and two phenols, methyl-4-hydroxybenzoate (paraben) and 4‑allyl-2-methoxyphenol (eugenol), at different order of their introduction into the reaction mixture. The hydrolysis of ester groups of aryloxycyclotriphosphazenes yields corresponding carboxyphenoxycyclophosphazenes, and the oxidation of their allyl groups by m-chloroperbenzoic acid affords epoxy derivatives. Optimal conditions for the indicated transformations are determined, and structure of the resulting oligomers is studied by 1Н and 31Р NMR spectroscopy and MALDI-TOF mass spectrometry.
REFERENCES
A. Medici, G. Fantin, P. Pedrini, M. Gleria, and F. Minto, Macromolecules 25 (10), 2569 (1992).
D. Alekperov, T. Shirosaki, T. Sahurai, G. Popova, V. Kireev, and H. Ihara, Polym. J. 35 (5), 417 (2003).
V. Chandrasekhar, Inorganic and Organometallic Polymers (Springer Verlag, Berlin, 2005).
A. K. Andrianov, Polyphosphazenes for Biomedical Applications (Wiley: Hoboken, 2009).
Phosphazenes: A Worldwide Insight, R. De. Jaeger and M. Gleria, Eds. (Nova Sci. Publ., New York, 2011), 2nd Quarter.
V. V. Kireev, E. M. Chistyakov, S. N. Filatov, R. S. Borisov, and B. M. Prudskov, Polym. Sci., Ser. B 53 (7–8), 412 (2011)
J. Liu, J. Tang, X. Wang, and D. Wu, RSC Adv. 2 (13), 5789 (2012).
I. V. Terekhov, S. N. Filatov, E. M. Chistyakov, R. S. Borisov, and V. V. Kireev, Russ. J. Appl. Chem. 86 (10), 1600 (2013).
I. S. Sirotin, Yu. V. Bilichenko, A. N. Solodukhin, V. V. Kireev, M. I. Buzin, and R. S. Borisov, Polym. Sci., Ser. B 55 (5–6), 241 (2013).
I. S. Sirotin, Candidate’s Dissertation in Chemistry (Moscow, 2013).
Funding
This work was supported by the Ministry of Science and Higher Education of the Russian Federation within the framework of State Assignment (project no. FSSM-2022-0010).
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
The authors declare that they have no conflicts of interest.
Additional information
Translated by T. Soboleva
Rights and permissions
About this article
Cite this article
Bilichenko, Y.V., Van Thuan, P., Borisov, R.S. et al. Synthesis of Mixed Functional Oligoaryloxycyclotriphosphazenes. Polym. Sci. Ser. B 64, 855–862 (2022). https://doi.org/10.1134/S1560090422700610
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1560090422700610