Abstract
Environmentally friendly method for the synthesis of crosslinked poly(siloxane-urethanes) avoiding the use of toxic isocyanates has been presented. The synthesis has been performed in two stages: at the first stage, non-isocyanate poly(siloxane-urethanes) have been synthesized via aminolysis of cyclocarbonates (differing in the structure and functionality) with oligomer dimethylsiloxanes bearing aminopropyl and ethoxy substituents, and crosslinked non-isocyanate poly(siloxane-urethanes) have been obtained via hydrolysis of the ethoxy groups with air moisture. According to the TGA data, processes of thermooxidative decomposition of the non-isocyanate poly(siloxane-urethanes) begin at 240‒260°C, depending on the structure of the organic block. Structural organization of the films has been investigated and glass transition temperature of two blocks (flexible siloxane and rigid urethane ones) has been determined by means of DSC and TMA. Surface of the film samples of non-isocyanate poly(siloxane-urethanes) has been assessed by means of scanning electron microscopy.
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REFERENCES
M. F. Sonnenschein, Polyurethanes. Science, Technology, Markets and Trends (Wiley, New York, 2014).
J. Lesage, I. DeGraff, and R. Danchik, Isocyanates: Sampling, Analysis and Health Effects (American Society for Testing and Materials, 2002, p. 138).
A. Redlich Carrie, Int. Immunopharmacol. 2 (2–3), 213 (2002).
S. K. Meredith, Occup. Environ. Med. 57 (12), 830 (2000).
Commission Regulation (EC). Off. J. Eur. Communities p. 552 (2009).
Methylene Diphenyl Isocyanate (MDI) and Related Compounds Action Plan, Toluene Diisocyanate (TDI) Action Plan [RIN 2070-ZA15]. U.S. Environmental Protection Agency, 2011.
O. Kreye, H. Mutlu, and M. A. R. Meier, Green Chem. 15 (6), 1431 (2013).
L. Maisonneuve, O. Lamarzelle, E. Rix, E. Grau, and H. Cramail, Chem. Rev. 115 (22), 12407 (2015).
M. R. Kember, A. Buchard, and C. K. Williams, Chem. Commun. 47 (1), 141 (2011).
L. Guo, K. J. Lamb, and M. North, Green Chem. 23, 77 (2021).
C. Le. Quere, R. B. Jackson, M. W. Jones, A. J. P. Smith, S. Abernethy, R. M. Andrew, A. J. De-Gol, D. R. Willis, Y. Shan, J. G. Canadell, P. Friedlingstein, F. Creutzig, and G. P. Peters, Nat. Clim. Change, No. 10, 647 (2020).
L. Poussard, J. Mariage, B. Grignard, C. Detrembleur, C. Jérôme, C. Calberg, B. Heinrichs, J. De Winter, P. Gerbaux, J.-M. Raquez, L. Bonnaud, and Ph. Dubois Ph, Macromolecules 49, 2162 (2016).
G. Beniah, K. Liu, W. H. Heath, M. D. Miller, K. A. Scheidt, and J. M. Torkelson, Eur. Polym. J. 84, 770 (2016).
S. Gennen, B. Grignard, J.-M. Thomassin, B. Gilbert, B. Vertruyen, C. Jerome, and C. Detrembleur, Eur. Polym. J. 84, 849 (2016).
A. Cornille, S. Dworakowska, D. Bogdal, B. Boutevin, and S. A. Caillol, Eur. Polym. J. 66, 129 (2015).
E. Dolci, G. Michaud, F. Simon, B. Boutevin, S. Fouquay, and S. Caillol, Polym. Chem., No. 6, 7851 (2015).
A. Cornille, G. Michaud, F. Simon, S. Fouquay, R. Auvergne, B. Boutevin, and S. Caillol, Eur. Polym. J. 84, 404 (2016).
B. Ochiai, S. Inoue, and T. Endo, J. Polym. Sci., Polym. Chem. 43, 6615 (2005).
A. Cornille, R. Auvergne, O. Figovsky, B. Boutevin, and S. Caillol, Eur. Polym. J. 87, 535 (2017).
M. Blain, L. Jean-Gérard, R. Auvergne, D. Benazet, S. Caillol, and B. Andrioletti, Green Chem. 16, 4286 (2014).
R. H. Lambeth and T. J. Henderson, Polymer 54, 5568 (2013).
A. P. Dove, ACS Macro Lett. 1, 1409 (2012).
Mhd. Abd. Haniffa Mhd. Cader, K. Munawar, Y. Ch. Ching, H. A. Illias, and Ch. H. Chuah, Chem. Asian J. 16, 1281 (2021).
M. Decostanzi, Y. Ecochard, and S. Caillol, Eur. Polym. J. 109, 1 (2018).
O. Figovsky, L. Shapovalov, and F. Buslov, Surf. Coat. Int., Part B 88 (B1), 1 (2005).
K. M. F. Rossi de Aguiar, E. P. Ferreira-Neto, S. Blunk, J. F. Schneider, C. A. Picon, C. M. Lepienski, K. Rischkae, and U. P. Rodrigues-Filho, RSC Adv., No. 6, 19160 (2016).
B. C. Weijie, W. Zhou, and T.-H. Wang, Lab Chip 12, 4120 (2012).
F. Askari, M. Barikani, and M. Barmar, J. Appl. Polym. Sci. 130 (3), 1743 (2013).
Ch.-An. Lu, M. Xu, Zh. Tan, Zh. Qu, K. Wu, and J. Shi, Colloid. Polym. Sci. 298, 1215 (2020).
N. Riehle, K. Athanasopulu, L. Kutuzova, T. Götz, A. Kandelbauer, G. E. M. Tovar, and G. Lorenz, Polymers 13, 212 (2021).
K. Hanada, K. Kimura, K. Takahashi, and M. Uruno, US Patent No. 2014/0024274A1 (2012).
K. R. Aguiar, V. G. Santos, M. N. Eberlin, K. Rischka, M. Noeske, G. Tremiliosi-Filho, and U. P. Rodrigues-Filho, RSC Adv. 4, 24334 (2014).
I. B. Meshkov, A. A. Kalinina, V. V. Gorodov, A. V. Bakirov, S. V. Krasheninnikov, S. N. Chvalun, and A. M. Muzafarov, Polymers 13 (17), 2848 (2021).
S. E. Lyubimov, A. A. Zvinchuk, V. A. Davankov, B. Chowdhury, A. V. Arzumanyan, and A. M. Muzafarov, Russ. Chem. Bull. 69 (6), 1076 (2020).
M. A. Levina, M. V. Zabalov, V. G. Krasheninnikov, and R. P. Tiger, Polym. Sci., Ser. B 6 (5), 563 (2018).
S. V. Vinogradova and V. A. Vasnev, Polycondensation Processes and Polymers (Nauka, Moscow, 2000) [in Russian].
Funding
This study was performed in the scope of the State Task from the Ministry of Science and Higher Education of the Russian Federation (no. 075-03-2023-642) and performed using the equipment of the Center for Investigation of Molecular Structure, Nesmeyanov Institute of Organoelement Compounds, RAS and the Center for Investigation of Polymers, Enikolopov Institute of Synthetic Polymeric Materials, RAS, supported by the Ministry of Science and Higher Education of the Russian Federation (no. FFSM-2021-0004) for 2021‒2023.
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Translated by E. Karpushkin
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Trankina, E.S., Kazantseva, A.Y., Khanin, D.A. et al. Non-Isocyanate Poly(Siloxane-Urethanes) Based on Oligodimethylsiloxanes Containing Aminopropyl and Ethoxy Substituents. Polym. Sci. Ser. C 65, 152–161 (2023). https://doi.org/10.1134/S1811238223700406
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DOI: https://doi.org/10.1134/S1811238223700406