Abstract
A new monomer containing thermosetting groups of two types, namely, propargyl ether and phthalonitrile, in the structure of the molecule was synthesized and studied. It was found that thermal polymerization was accompanied by the degradation of the monomer with propargyl ether decomposition. This problem can be solved using catalysts based on Cu(i) favoring the polymerization at both the propargyl group and phthalonitrile fragments. The cured monomer has a non-porous structure and high thermal properties (Vicat softening temperature 395 °C, T5% 451 °C). The low viscosity of the melt (<200 mPa s at 120 °C) and low glass-transition temperature (9 °C) of the monomer make it possible to use it for the formation of composite materials by vacuum infusion or injection into a mold.
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B. Bulgakov, D. Kalugin, A. Babkin, I. Makarenko, A. Malakho, A. Kepman, V. Avdeev, N. Garadja, A. Rogozin, Can. J. Chem. Eng., 2016, 94, 46.
S. S. Nechausov, B. A. Bulgakov, A. V. Solopchenko, A. A. Serdan, D. I. Kalugin, A. Lyalin, A. V. Kepman, A. P. Malakho, J. Polym. Res., 2016, 23, 114.
S. E. Evsyukov, T. Pohlmann, H. D. Stenzenberger, Polym. Adv. Technol., 2015, 26, 574.
A. V. Babkin, E. M. Erdni-Goryaev, A. V. Solopchenko, A. V. Kepman, V. V. Avdeev, Polym. Adv. Technol., 2016, 27, 774.
I. Hamerton, Chemistry and Technology of Cyanate Ester Resins, Springer Science & Business Media, 2012.
C. Uhlig, M. Bauer, J. Bauer, O. Kahle, A. C. Taylor, A. J. Kinloch, React. Funct. Polym., 2018, 129, 2.
B. C. Kholkhoev, Mendeleev Commun., 2019, 29, 223.
H. R. Lubowitz, C. H. Sheppard, EU Pat. 0405128A2, 1992.
H. D. Stenzenberger, Addition Polyimides, in High Performance Polymers, Springer-Verlag, 1994, 165; DOI: https://doi.org/10.1007/BFb0021199.
S. B. Sastri, T. M. Keller, J. Polym. Sci., Part A: Polym. Chem., 1998, 36, 1885.
M. Laskoski, D. D. Dominguez, T. M. Keller, Am. Chem. Soc., 2009, 922, 378.
T. M. Keller, J. R. Griffith, US Pat. 4259471A, 1979.
B. A. Bulgakov, A. V. Sulimov, A. V. Babkin, D. V. Afanasiev, A. V. Solopchenko, E. S. Afanaseva, A. V. Kepman, V. V. Avdeev, Mendeleev Commun., 2017, 27, 257.
M. V. Yakovlev, O. S. Morozov, E. S. Afanaseva, B. A. Bulgakov, A. V. Babkin, A. V. Kepman, React. Funct. Polym., 2020, 146, 104409; DOI: https://doi.org/10.1016/j.reactfunctpolym.2019.104409.
M. Derradji, N. Ramdani, T. Zhang, Mater. Des., 2015, 71, 48.
T. M. Keller, J. R. Griffith, US Pat. 4223123, 1980.
R. Y. Ting, T. M. Keller, T. R. Price, C. F. Poranski, Characterization of the Cure of Diether-Linked Phthalonitrile Resins, in ACS Symposium Series, 1982, 337; DOI: https://doi.org/10.1021/bk-1982-0195.ch026.
T. M. Keller, T. R. Price, J. Macromol. Sci., Part A: Chem., 1982, 18, 931.
Ke Zeng, Ke Zhou, Wen Rui Tang, Yan Tang, Hong Fei Zhou, Tao Liu, Yi Peng Wang, Hai Bing Zhou, Gang Yang, Chinese Chem. Lett., 2007, 18, 523.
K. Zeng, K. Zhou, S. H. Zhou, H. B. Hong, H. F. Zhou, Y. P. Wang, P. K. Miao, G. Yang, Eur. Polym. J., 2009, 45, 1328.
D. Augustine, D. Mathew, C. P. Reghunadhan Nair, Polymer, 2015, 60, 308.
D. Augustine, D. Mathew, C. P. Reghunadhan Nair, Eur. Polym. J., 2015, 71, 389.
S. K. Dirlikov, High Performance Polymers, 1990, 2, 67; DOI: https://doi.org/10.1177/152483999000200107.
S. Dirlikov, Z. Chen, D. Wang, Polymer, 1993, 34, 705.
B. A. Bulgakov, A. V. Sulimov, A. V. Babkin, A. V. Kepman, A. P. Malakho, V. V. Avdeev, J. Appl. Polym. Sci., 2017, 133, 44786.
W. E. Douglas, A. S. Overend, Eur. Polym. J., 1993, 29, 1513.
W. E. Douglas, A. S. Overend, Polymer, 1993, 34, 1544.
K. Balaraman, V. Kesavan, Synthesis, 2010, 3461; DOI: https://doi.org/10.1055/s-0030-1258199.
B. Bulgakov, A. Babkin, I. Makarenko, Eur. Polym. J., 2015, 73, 247.
S. B. Sastri, J. P. Armistead, T. M. Keller, Polym. Compos., 1996, 17, 816.
J. Wang, J. Hu, K. Zeng, G. Yang, RSC Adv., 2015, 5, 105038.
M. Laskoski, J. Polym. Sci., Part A: Polym. Chem., 2018, 56, 1128.
B. G. Sun, Qin Lei, Ying Guo, Han-Qiao Shi, Jian-Bo Sun, Kun-Xiao Yang, Heng Zhou, Yuan-Qing Li, Ning Hu, Hao Wang, Shao-Yun Fu, Compos., Part B: Eng., 2019, 166, 681.
B. A. Bulgakov, A. V. Babkin, P. B. Dzhevakov, A. A. Bogolyubov, A. V. Sulimov, A. V. Kepman, Yu. G. Kolyagin, D. V. Guseva, V. Yu. Rudyak, A. V. Chertovich, Eur. Polym. J., 2016, 84, 205.
A. V. Babkin, E. B. Zodbinov, B. A. Bulgakov, A. V. Kepman, V. V. Avdeev, Eur. Polym. J., 2015, 66, 452.
B. A. Bulgakov, A. V. Babkin, A. A. Bogolyubov, E. S. Afanas’eva, A. V. Kepman, Russ. Chem. Bull., 2016, 65, 287.
V. E. Terekhov, V. V. Aleshkevich, E. S. Afanaseva, S. S. Nechausov, A. V. Babkin, B. A. Bulgakov, A. V. Kepman, V. V. Avdeev, React. Funct. Polym., 2019, 139, 34.
B. A. Bulgakov, A. V. Sulimov, A. V. Babkin, I. A. Timoshkin, A. V. Solopchenko, A. V. Kepman, V. V. Avdeev, J. Compos. Mater., 2017, 51, 4157.
B. A. Bulgakov, K. S. Belsky, S. S. Nechausov, E. S. Afanaseva, A. V. Babkin, A. V. Kepman, V. V. Avdeev, Mendeleev Commun., 2018, 28, 44.
A. V. Babkin, A. V. Sulimov, B. A. Bulgakov, A. V. Kepman, SAMPE Tech. Conf., Society for the Advancement of Material and Process Engineering, 2017, 713.
F. C. Campbell, Manufacturing Processes for Advanced Composites, 2003, Elsevier, 517; DOI: https://doi.org/10.1016/B978-1-85617-415-2.X5000-X.
M. Wang, L. Wei, T. Zhao, Eur. Polym. J., 2005, 41, 903.
S. A. Znoyko, T. V. Tikhomirova, A. I. Petlina, I. V. Novikov, A. S. Vashurin, O. I. Koifman, Russ. Chem. Bull., 2019, 68, 1271.
Mehdi Derradji, Wang Jun, Liu Wenbin, Phthalonitrile Resins and Composites: Properties and Applications, Elsevier, 2018, 404.
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This work was carried out in the framework of the state assignment of the Department of Chemistry of the M. V. Lomonosov Moscow State University (Agreement No. AAAA-A16-116053110012-5).
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 2183—2190, November, 2020.
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Yakovlev, M.V., Morozov, O.S., Afanaseva, E.S. et al. Trifunctional thermosetting monomer with propargyl and phthalonitrile groups. Russ Chem Bull 69, 2183–2190 (2020). https://doi.org/10.1007/s11172-020-3020-3
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DOI: https://doi.org/10.1007/s11172-020-3020-3