Anionic Polymerization of Ethyl 2-Cyanoacrylate Initiated by 1,3-Dimethylimidazolium (phosphonooxy-)oligosulfanide

Natalia Tarasova; Efrem Krivoborodov; Alexey Zanin; Ilya Toropygin; Ekaterina Pascal; Valerie Dyatlov; Yaroslav Mezhuev

Macromolecular Research, Vol.29, No.12, 847-850, December, 2021

DOI10.1007/s13233-021-9104-6 Export Citation

Anionic Polymerization of Ethyl 2-Cyanoacrylate Initiated by 1,3-Dimethylimidazolium (phosphonooxy-)oligosulfanide

Natalia Tarasova^{1, 2}, Efrem Krivoborodov¹, Alexey Zanin^{1, †}, Ilya Toropygin³, Ekaterina Pascal¹, Valerie Dyatlov¹, and Yaroslav Mezhuev¹

¹Institute of Chemistry and Problems of Sustainable Development, Dmitry Mendeleev University of Chemical Technology of Russia, 12047 Moscow, Russia, Russian Federation
²Institute of Geology of Ore Deposits, Petrography, Mineralogy, and Geochemistry, Russian Academy of Sciences, 119017 Moscow, Russia, Russian Federation
³V. N. Orekhovich Research Institute of Biomedical Chemistry, Russian Academy of Medical Sciences, 119121 Moscow, Russia, Russian Federation

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The possibility of initiating anionic polymerization in the presence of 1,3-dimethylimidazolium (phosphonooxy-)oligosulfanide is shown by the example of the synthesis of poly(ethyl 2-cyanoacrylate). The structure of the synthesized poly(ethyl 2-cyanoacrylate) was characterized by 13C nuclear magnetic resonance (NMR), 1H NMR, and matrix-assisted laser desorption ionization-time of flight methods on positively and negatively charged ions. It is shown that the chains of synthesized poly(ethyl 2-cyanoacrylate) have a terminal group containing sulfur and phosphorus atoms. The presence of sulfur and phosphorus atoms in the terminal group confirms the initiation of anionic polymerization as a result of nucleophilic attack by (phosphonooxy- oligosulfanide anion by electrophilic ethyl 2-cyanoacrylate.

Keywords:poly(ethyl 2-cyanoacrylate);ionic liquids;elemental sulfur;anionic polymerization

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[1] Boyd DA, Angew. Chem.-Int. Edit., 55, 2 (2016)

[2] Worthington MJH, Kucera RL, Chalker JM, Green Chem., 19, 2748 (2017)

[3] Smith JA, Mulhall R, Goodman S, Fleming G, Allison H, Raval R, Hasell T, ACS Omega, 5, 5229 (2020)

[4] Tarasova NP, Zanin AA, Krivoborodov EG, Mezhuev YO, RSC Adv., 11, 9008 (2021)

[5] Steudel R, Paßlack-Stephan S, Holdt G, Z. Anorg. Allg. Chem., 517, 7 (1984)

[6] Steudel R, Top. Curr. Chem., 230, 1 (2003)

[7] Terada N, Kouge K, Komaguchi K, Hayakawa S, Tsutsumi H, Anal. Sci., 36, 75 (2020)

[8] Chung WJ, Griebel JJ, Kim ET, et al., Nat. Chem., 5, 518 (2013)

[9] Zhang YY, Pavlopoulos NG, Kleine TS, Karayilan M, Glass RS, Char K, Pyun J, J. Polym. Sci. A: Polym. Chem., 57(1), 7 (2019)

[10] Griebel JJ, Glass RS, Char K, Pyun J, Prog. Polym. Sci, 58, 90 (2016)

[11] Zhang Y, Glass RS, Char K, Pyun J, Polym. Chem., 10, 4078 (2019)

[12] Orme K, Fistrovich AH, Jenkins CL, Macromolecules, 53(21), 9353 (2020)

[13] Zhang Y, Kleine T, Carothers K, Phan D, Glass RS, Mackay M, Char K, Pyun J, Polym. Chem., 9, 2290 (2018)

[14] Wu X, Simth JA, Petcher S, Zhang B, Parker DJ, Griffin JM, Hassel T, Nat. Commun., 10, 647 (2019)

[15] Karayilan M, Kleine TS, Carothers KJ, Griebel JJ, Frederick KM, Loy DA, Glass RS, Mackay ME, Char K, Pyun J, J. Polym. Sci. A: Polym. Chem., 58, 35 (2020)

[16] Kwon MH, Lee HC, Lee SH, Jeon HB, Oh MC, Pyun J, Paik HJ, Macromol. Res., 28(11), 1003 (2020)

[17] Kim JS, Noh ST, Kweon JO, Cho BS, Macromol. Res., 23(4), 341 (2015)

[18] Mostoni S, Milana P, Di Credico B, D’Arienzo M, Scotti R, Catalysts, 9, 664 (2019)

[19] Bhargav A, Bell ME, Cui Y, Fu YZ, ACS Appl. Energ. Mater., 1, 5859 (2018)

[20] Maladeniya CP, Karunarathna MS, Lauer MK, Lopez CV, Thiounn T, Smith RC, Mater. Adv., 1, 1665 (2020)

[21] Kausar A, Zulfiqar S, Sarwar MI, Polym. Rev., 54, 185 (2016)

[22] Zhu X, Zhou F, Yang Y, Deng G, Liang Y, ACS Omega, 5, 13136 (2020)

[23] Tarasova NP, Mezhuev YO, Zanin AA, Krivoborodov EG, Doklady Chem., 484, 8 (2019)

[24] Tarasova N, Krivoborodov E, Egorova A, Glukhov AZL, Toropygin I, Mezhuev Y, Pure Appl. Chem., 92, 1297 (2020)

[25] Tarasova N, Krivoborodov E, Zanin A, Mezhuev Y, Pure Appl. Chem., 93, 29 (2021)

[26] Tarasova N, Zanin A, Krivoborodov E, Motyakin M, Levina I, Dyatlov V, Toropygin I, Dyakonov V, Mezhuev Y, Green Chem. Lett. Rev., 14, 435 (2021)

[27] Tarasova N, Zanin A, Krivoborodov E, Pascal E, Mezhuev Y, Polymers, 13, 1806 (2021)

[28] Leonard F, Kulkarni RK, Brandes G, Nelson J, Cameron JJ, J. Appl. Polym. Sci., 10, 259 (1966)

[29] Katti D, Krishnamurti N, J. Appl. Polym. Sci., 74(2), 336 (1999)

[30] Han MG, Kim S, Liu SX, Polym. Degrad. Stabil., 93, 1243 (2008)

[31] Denchev Z, Tomanova M, Lederer A, J. Polym. Sci. A: Polym. Chem., 46(15), 5142 (2008)

[32] Robello DR, Eldridge TD, Swanson MT, J. Polym. Sci. A: Polym. Chem., 37(24), 4570 (1999)

[33] Rustamov IR, Dyatlov VA, Grebeneva TA, Dyatlov AV, Zaitsev VV, Maleev VI, J. Mater. Chem. B, 2, 4310 (2014)

[34] Tripodo G, Wischke C, Lendlein A, Macromol. Symp., 309, 49 (2011)

[35] Holloczki O, Gerhard D, Massone K, Szarvas L, Nemeth B, Veszpremi T, Nyulaszi L, New J. Chem., 34, 3004 (2010)

[36] Sowmiah S, Srinivasadesikan V, Tseng MC, Chu YH, Molecules, 14, 3780 (2009)

[37] Olofson RA, Thompson WR, Michelman JS, J. Am. Chem. Soc., 86, 1865 (1964)