Abstract
New initiator monomers, derivatives of 3,5-di-tert-butyl-o-benzoquinone containing the 2‑hydroxyethyl methacrylate (HEMA) and pentaerythritol triacrylate (PETA) moieties, have been synthesized. The activity of new o-quinones has been examined in the visible light-induced polymerization (coinitiator N,N-dimethylcyclohexylamine) of oligocarbonate dimethacrylate OCM‑2. The thermal stability of the obtained polymers has been studied. Polymers have been prepared by copolymerization of the synthesized o-quinones with HEMA and PETA (initiator azobisisobutyronitrile, 80°C), and the migration of o-quinones from the products has been evaluated.
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REFERENCES
Wang, D., Aqueous colored photocurable paint and preparation method thereof, A. c. CN 2021-10066000, 2021, p. 11.
Hou, H., Gan, Ya., Yin, J., and Jiang, X., Langmuir, 2017, vol. 33, no. 8, p. 2027.
Shah, A.H., Kartheek, P., Gandhi, P., Jonnalagadda, K., and Steele, T.W.J., Macromol. Mater. Eng., 2019, no. 11, Article 1900230.
Ao-Ieong, W.-S., Chien, S.-T., Jiang, W.-C., Yet, S.-F., and Wang, J., Polymers, 2021, vol. 13, no. 12, Article 1960.
Seror, J., Stern, M., Zarka, R., and Orr, N., Plast. Reconstr. Surg., 2021, vol. 148, no. 6S, p. 32.
Bagheri, A. and Jin, J., ACS Appl. Polym. Mater., 2019, vol. 1, no. 4, p. 593.
Van Bochove, B., Hannink, G., Buma, P., and Grijpma, D.W., Macromol. Biosci., 2016, vol. 16, no. 12, p. 1853.
Sutton, J., Rajan, K., Harper, D.P., and Chmely, S.C., ACS Appl. Mater. Interfaces, 2018, vol. 10, no. 42, p. 36456.
Chen, Yu., Sun, C., Zhou, H., Li, J., Xin, W., Xu, H., and Zhu, H., J. Phys. Chem. Lett., 2021, vol. 12, no. 40, p. 9989.
Levett, P.A., Melchels, F.P.W., Schrobback, K., Hutmacher, D.W., Malda, J., and Klein, T.J., Acta Biomater., 2013, vol. 10, no. 1, p. 214.
Ferracci, G., Zhu, M., Ibrahim, M.S., Ma, G., Fan, T.F., Lee, B.H., and Cho, N.-J., ACS Appl. Bio Mater., 2020, vol. 3, no. 2, p. 920.
Wu, Q., Mo, Y., Zhang, Y., Li, F., and Deng, M., Macromol. Chem. Phys., 2021, vol. 222, no. 20, p. 2100221.
Eren, T.N., Okte, N., Morlet-Savary, F., Fouassier, J.P., Lalevee, J., and Avci, D., J. Polym. Sci., Part A: Polym. Chem., 2016, vol. 54, no. 20, p. 3370.
Zhang, T., Jiang, B., and Huang, Yu., Compos., Part B: Eng., 2018, vol. 140, p. 214.
Tang, Y., Zhang, Y., Yang, J., and Nie, J., J. Polym. Sci., Part A: Polym. Chem., 2017, vol. 55, p. 313.
Shurygina, M.P., Zakharina, M.Yu., Baten’kin, M.A., Konev, A.N., Shavyrin, A.S., Chelnokov, E.A., Shushunova, N.Yu., Arsenyev, M.V., Chesnokov, S.A., and Abakumov, G.A., Eur. Polym. J., 2020, vol. 127, Article 109573.
Arsenyev, M.V., Shurygina, M.P., Poddel’sky, A.I., Druzhkov, N.O., Chesnokov, S.A., Fukin, G.K., Cherkasov, V.K., and Abakumov, G.A., J. Polym. Res., 2013, vol. 20, p. 98.
Shushunova, N.Yu., Arsenyev, M.V., Glukhova, T.A., Zaitsev, S.D., and Chesnokov, S.A., Polym. Sci., Ser. B, 2015, vol. 57, no. 3, p. 207.
Arsenyev, M.V., Baranov, E.V., Shurygina, M.P., Chesnokov, S.A., and Abakumov, G.A., Mendeleev Commun., 2016, vol. 26, no. 6, p. 552.
Poddel’sky, A.I., Arsenyev, M.V., Astaf’eva, T.V., Chesnokov, S.A., Fukin, G.K., and Abakumov, G.A., J. Organomet. Chem., 2017, vol. 835, p. 17.
Zhiganshina, E.R., Arsenyev, M.V., Shavyrin, A.S., Baranov, E.V., and Chesnokov, S.A., Mendeleev Commun., 2019, vol. 29, p. 91.
Armarego, W.L.F. and Chai, C.L.L., Purification of Laboratory Chemicals, Amsterdam: Elsevier, 2003, 5th ed.
Shurygina, M.P., Kurskii, Yu.A., Druzhkov, N.O., Chesnokov, S.A., and Abakumov, G.A., High Energy Chem., 2010, vol. 44, p. 234.
Si, Q.F., Wang, X., Fan, X.D., and Wang, S.J., J. Polym. Sci., Part A: Polym. Chem., 2005, vol. 43, p. 1883.
Funding
This work was supported by the Russian Science Foundation, project no. 19-73-10173. The work was performed using the equipment of the Shared-Use Analytical Center at the Institute of Organometallic Chemistry of the Russian Academy of Sciences with the support of the grant “Providing for the development of the material and technical infrastructure of centers for shared use of scientific equipment” (project unique identifier RF–2296.61321X0017, agreement no. 075-15-2021-670).
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Translated by S. Zatonsky
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Zhiganshina, E.R., Lysenkov, V.S., Lopatina, T.I. et al. (Met)acrylate-Containing Sterically Hindered o-Benzoquinones for free Radical Polymerization. High Energy Chem 56, 163–169 (2022). https://doi.org/10.1134/S0018143922030134
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DOI: https://doi.org/10.1134/S0018143922030134