Abstract
A modified synthetic method for amino-terminated oligo tetramethylene oxides is presented. Diamines were synthesized via a three-step route from oligo tetramethylene oxide diol with an average molecular weight of 2000. The final step – oligoether-diphthalimide hydrazinolysis – has been improved. The yield of the target product has been shown to be more than 1.5 times higher when the molar ratio of the reacting components was changed. The oligoether-diamine and the reaction intermediates have been identified by 1H and 13C NMR spectroscopy. It has been demonstrated that the synthesized amine can be used as a curing agent for epoxy urethane oligomers. It is shown that the glass transition temperature of the cured elastomers is lower than −70 °C. These elastomers can be recommended for the use in the conditions of the Arctic and the Far North or Far South of the globe.
Acknowledgments
The reported study was funded by RFBR and Perm Territory, project number No. 20-43-596010. The research was carried out within the framework of the State Assignment (theme state registration number 122011900165-2) and the project “Chemical Products in Subsoil Use” of the Perm Scientific and Educational Center “Rational Subsoil Use”.
-
Author contributions: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.
-
Research funding: None declared.
-
Conflict of interest statement: The authors declare no conflicts of interest regarding this article.
References
1. Leonardi, A. B., Fasce, L. A., Zucchi, I., Hoppe, C. E., Soulé, E. R., Perez, C. J., Williams, R. J. Eur. Polym. J. 2011, 47, 362–369; https://doi.org/10.1016/j.eurpolymj.2010.12.009.Search in Google Scholar
2. Xiao, X., Kong, D., Qiu, X., Zhang, W., Liu, Y., Zhang, S., Zhang, F., Hu, Y., Leng, J. Sci. Rep. 2015, 5, 14137 (12 pages); https://doi.org/10.1038/srep14137.Search in Google Scholar PubMed PubMed Central
3. Zhang, F. H., Zhang, Z. C., Luo, C. J., Lin, I.-T., Liu, Y., Leng, J., Smoukov, S. K. J. Mater. Chem. C 2015, 3, 11290–11293; https://doi.org/10.1039/c5tc02464a.Search in Google Scholar
4. Xiao, R., Guo, J., Safranski, D. L., Nguyen, T. D. Soft Matter 2015, 11, 3977–3985; https://doi.org/10.1039/c5sm00543d.Search in Google Scholar PubMed
5. Dong, Y., Xia, H., Zhu, Y., Ni, Q.-Q., Fu, Y. Compos. Sci. Technol. 2015, 120, 17–25; https://doi.org/10.1016/j.compscitech.2015.09.011.Search in Google Scholar
6. Prathumrat, P., Tiptipakorn, S., Rimdusit, S. Smart Mater. Struct. 2017, 26, 065025 (9 pages); https://doi.org/10.1088/1361-665x/aa6d47.Search in Google Scholar
7. Ang, J. Y., Chan, B. Q. Y., Kai, D., Loh, X. J. Macromol. Mater. Eng. 2017, 302, 1700174 (11 pages); https://doi.org/10.1002/mame.201700174.Search in Google Scholar
8. Puszka, A., Sikora, J. W. Materials 2022, 15, 4940; https://doi.org/10.3390/ma15144940.Search in Google Scholar PubMed PubMed Central
9. Xu, J., Xiao, W., Zhang, S., Dong, Z., Lei, C. Eur. Polym. J., 2022, 179, 111553 (9 pages).10.1016/j.eurpolymj.2022.111553Search in Google Scholar
10. Jing, X., Li, X., Di, Y., Zhao, Y., Wang, J., Kang, M., Li, Q. Polymer 2021, 233, 124205 (13 pages); https://doi.org/10.1016/j.polymer.2021.124205.Search in Google Scholar
11. Candau, N., Stoclet, G., Tahon, J. F., Demongeot, A., Yilgor, E., Yilgor, I., Menceloglu, Y. Z., Oguz, O. Polymer 2021, 223, 123708.10.1016/j.polymer.2021.123708Search in Google Scholar
12. Filip, D., Macocinschi, D., Tuchilus, C. G., Zaltariov, M. F., Varganici, C. D. Macromol. Res. 2021, 9, 613–624; https://doi.org/10.1007/s13233-021-9069-5.Search in Google Scholar
13. Zarei, M. A., Bayat, Y., Oskueyan, G. J. Macromol. Sci., Pure Appl. Chem. 2022, 59, 666–674; https://doi.org/10.1080/10601325.2022.2108442.Search in Google Scholar
14. Volkova, E. R., Strelnikov, V. N., Borisova, I. A., Slobodinyuk, A. I., Savchuk, A. V. Polym. Sci., Ser. D 2018, 11, 292–296; https://doi.org/10.1134/s1995421218030231.Search in Google Scholar
15. Volkova, E. R., Tereshatov, V. V., Vnutskikh, Z. A. Russ. J. Appl. Chem. 2010, 83, 1372–1379; https://doi.org/10.1134/s1070427210080082.Search in Google Scholar
16. Ahn, T. O., Jung, S. U., Jeong, H. M., Lee, S. W. J. Appl. Polym. Sci. 1994, 51, 43–49; https://doi.org/10.1002/app.1994.070510105.Search in Google Scholar
17. Strel’nikov, V. N., Senichev, V. Y., Slobodinyuk, A. I., Savchuk, A. V., Volkova, E. R., Makarova, M. A., Belov, Yu. L., Derzhavinskaya, L. F., Selivanova, D. G. Russ. J. Appl. Chem. 2018, 91, 1937–1944; https://doi.org/10.1134/s1070427218120042.Search in Google Scholar
18. Tereshatov, V. V., Tereshatova, E. N., Makarova, M. A., Tereshatov, S. V. Polymer Science A 2002, 44, 275–281.Search in Google Scholar
19. Yeganeh, H., Jamshidi, S., Talemi, P. H. Eur. Polym. J. 2006, 42, 1743–1754; https://doi.org/10.1016/j.eurpolymj.2006.02.011.Search in Google Scholar
20. Izadi, M., Mardani, H., Roghani-Mamaqani, H., Salami-Kalajahi, M., Khezri, K. ChemistrySelect 2021, 6, 2692–2699; https://doi.org/10.1002/slct.202004307.Search in Google Scholar
21. Byczyński, Ł., Dutkiewicz, M., Maciejewski, H. Prog. Org. Coating 2015, 84, 59–69; https://doi.org/10.1016/j.porgcoat.2015.02.017.Search in Google Scholar
22. Levchik, S. V., Weil, E. D. Polym. Int. 2004, 53, 1901–1929; https://doi.org/10.1002/pi.1473.Search in Google Scholar
23. Levchik, S., Piotrowski, A., Weil, E., Yao, Q. Polym. Degrad. Stabil. 2005, 88, 57–62; https://doi.org/10.1016/j.polymdegradstab.2004.02.019.Search in Google Scholar
24. Wang, J. S., Liu, Y., Zhao, H. B., Liu, J., Wang, D. Y., Song, Y. P., Wang, Y. Z. Polym. Degrad. Stabil. 2009, 94, 625–631; https://doi.org/10.1016/j.polymdegradstab.2009.01.006.Search in Google Scholar
25. Dogan, M., Unlu, S. M. Polym. Degrad. Stabil. 2014, 99, 12–17; https://doi.org/10.1016/j.polymdegradstab.2013.12.017.Search in Google Scholar
26. Slobodinyuk, A., Strelnikov, V., Senichev, V. Y., Slobodinyuk, D. Polymers 2022, 14, 524; https://doi.org/10.3390/polym14030524.Search in Google Scholar PubMed PubMed Central
27. Brandl, F., Henke, M., Rothschenk, S., Gschwind, R., Breunig, M., Blunk, T., Tessmar, J., Göpferich, A. Adv. Eng. Mater. 2007, 9, 1141–1149; https://doi.org/10.1002/adem.200700221.Search in Google Scholar
28. Abdollahi, H., Salimi, A., Barikani, M., Zeynizadeh, B. Mater. Manuf. Process. 2017, 32, 1296–1303; https://doi.org/10.1080/10426914.2017.1279292.Search in Google Scholar
29. Slobodinyuk, A., Strelnikov, V., Kiselkov, D., Slobodinyuk, D. Z. Naturforsch. 2021, 76b, 511–515.10.1515/znb-2021-0085Search in Google Scholar
30. Slobodinyuk, A., Strelnikov, V., Elchisheva, N., Kiselkov, D., Slobodinyuk, D. Polymers 2022, 14, 2136; https://doi.org/10.3390/polym14112136.Search in Google Scholar PubMed PubMed Central
31. Kissinger, H. E. Anal. Chem. 1957, 29, 1702–1706; https://doi.org/10.1021/ac60131a045.Search in Google Scholar
32. Ma, S., Liu, X., Fan, L., Jiang, Y., Cao, L., Tang, Z., Zhu, J. ChemSusChem 2014, 7, 555–562; https://doi.org/10.1002/cssc.201300749.Search in Google Scholar PubMed
33. Chung, S. H., Chung, S. H., Lin, T. J., Hu, Q. Y., Tsai, C. H., Pan, P. S. Molecules 2013, 18, 12346–12367; https://doi.org/10.3390/molecules181012346.Search in Google Scholar PubMed PubMed Central
34. Strel’nikov, V. N., Senichev, V. Y., Slobodinyuk, A. I., Savchuk, A. V., Volkova, E. R., Makarova, M. A., Nechaev, A. I., Krasnosel’skikh, S. F., Ukhin, K. O. Russ. J. Appl. Chem. 2018, 91, 463–468; https://doi.org/10.1134/s1070427218030199.Search in Google Scholar
© 2023 Walter de Gruyter GmbH, Berlin/Boston