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Effect of the type of hydrogen bonding on the reactivity of hydroxyl groups in the acetalization of poly(vinyl alcohol) with butanal

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Abstract

The parameters of hydrogen bonds formed during acetalization of poly(vinyl alcohol) with butanal are determined via computer-simulation methods. It is shown that alcohol groups involved in the formation of intermolecular hydrogen bonds are the least active in acetalization reactions. The kinetics of the acetalization reactions in 2,4-pentanediol-water-butanal and (vinyl alcohol)-water-butanal systems are studied at various concentrations of alcohols that model a change in the ratio of hydrogen bonds of various types and are realized in the aqueous solutions of poly(vinyl alcohol) and poly(vinyl butyral). The calculated rate constants are in agreement with the computer-simulation-based order of reactivity of alcohol groups involved in hydrogen bonds of various types. It is proposed that the reactivity of residual alcohol groups in a poly(vinyl butyral) macromolecule should increase when a certain conversion of the polymer is attained.

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References

  1. M. D. Fernandez, M. J. Fernandez, and P. Hoces, J. Appl. Polym. Sci. 102, 5007 (2006).

    Article  CAS  Google Scholar 

  2. Guo-dong Li and Zhang Yi, Chin. Adhes. 15 (6), 27 (2006).

  3. M. Dimitrova, S. Ilieva, and B. Galabov, J. Mol. Struct. 657, 317 (2003).

    Article  CAS  Google Scholar 

  4. B. G. Oliveira and M. L. Vasconcellos, J. Mol. Struct. (THEOCHEM) 774, 83 (2006).

    Article  CAS  Google Scholar 

  5. J. A. Padro, L. Saiz, and E. Guardia, J. Mol. Struct. 416, 243 (1997).

    Article  CAS  Google Scholar 

  6. M. A. Varfolomeev, D. I. Abaidullina, and B. N. Solomonov, Uch. Zap. Kazansk. Gos. Univ., Ser. Estestv. Nauki 151, 9 (2009).

    Google Scholar 

  7. M. S. Rumyantsev, V. I. Faerman, and A. V. Gushchin, Vestn. Nizhegorodsk. Gos. Univ. 2, 81 (2011).

    Google Scholar 

  8. G. N. Kormanovskaya and I. N. Vlodavets, Izv. Akad. Nauk SSSR, Ser. Khim. 10, 1748 (1964).

    Google Scholar 

  9. D. C. Young, Computational Chemistry (Wiley, New York, 2001).

    Book  Google Scholar 

  10. http://avogadro.openmolecules.net

  11. A. De la Rosa, L. Heux, J. Y. Cavaille, and K. Mazeau, Polymer 43, 5665 (2002).

    Article  Google Scholar 

  12. M. S. Raman, V. Ponnuswamy, P. Kolandaivel, and K. Perumal, J. Mol. Liq. 151, 97 (2010).

    Article  Google Scholar 

  13. J. A. Pople, P. M. W. Gill, and B. G. Johnson, Chem. Phys. Lett. 199, 557 (1992).

    Article  CAS  Google Scholar 

  14. G. E. Scuseria, J. Chem. Phys. 97, 7528 (1992).

    Article  CAS  Google Scholar 

  15. C. Adamo and V. Barone, Chem. Phys. Lett. 274, 242 (1997).

    Article  CAS  Google Scholar 

  16. A. D. Becke, J. Chem. Phys. 107, 8554 (1997).

    Article  CAS  Google Scholar 

  17. J. P. Merrick, D. Moran, and L. Radom, J. Phys. Chem. A 111, 11683 (2007).

    Article  CAS  Google Scholar 

  18. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery, T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J.V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez, and J. A. Pople, Gaussian, Revision B.03 (Gaussian, Pittsburgh, 2003).

  19. R. Parthasarathi, V. Subramanian, and N. Sathyamurthy, J. Phys. Chem. A 109, 843 (2005).

    Article  CAS  Google Scholar 

  20. E. V. Stovbun, E. R. Badamshina, V. A. Grigor’eva, V. P. Lodygina, A. I. Kuzaev, and S. M. Baturin, Polymer Science, Ser. A 40, 793 (1998) [Vysokomol. Soedin., Ser. A 40, 1291 (1998)].

    Google Scholar 

  21. E. R. Badamshina, V. A. Grigor’eva, G. A. Gorbushina, I. V. Doronina, V. P. Lodygina, and E. V. Stovbun, Polymer Science, Ser. A 43, 818 (2001) [Vysokomol. Soedin., Ser. A 43, 1321 (2001)].

    Google Scholar 

  22. B. J. Kline, E. J. Beckman, and A. J. Russel, J. Am. Chem. Soc. 120, 9475 (1998).

    Article  CAS  Google Scholar 

  23. N. Moitessier and Y. Chapleur, Tetrahedron Lett. 44, 1731 (2003).

    Article  CAS  Google Scholar 

  24. Y. He, B. Zhu, and Y. Inoue, Prog. Polym. Sci. 29, 1021 (2004).

    Article  CAS  Google Scholar 

  25. B. Stuart, Infrared Spectroscopy: Fundamentals and Applications (Wiley, New York, 2004).

    Book  Google Scholar 

  26. V. M. Bilobrov, Hydrogen Bond: Intramolecular Interactions (Naukova Dumka, Kiev, 1991) [in Russian].

    Google Scholar 

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Authors and Affiliations

  1. Nizhni Novgorod State University, pr. Gagarina 23, korp. 5, Nizhni Novgorod, 603950, Russia

    M. S. Rumyantsev, A. V. Gushchin & S. V. Zelentsov

  2. Kargin Research Institute of Polymers, Dzerzhinsk, Nizhni Novgorod oblast, 606000, Russia

    M. S. Rumyantsev

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  1. M. S. Rumyantsev
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  2. A. V. Gushchin
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  3. S. V. Zelentsov
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Correspondence to M. S. Rumyantsev.

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Original Russian Text © M.S. Rumyantsev, A.V. Gushchin, S.V. Zelentsov, 2012, published in Russian in Vysokomolekulyarnye Soedineniya, Ser. B, 2012, Vol. 54, No. 9, pp. 1497–1504.

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Rumyantsev, M.S., Gushchin, A.V. & Zelentsov, S.V. Effect of the type of hydrogen bonding on the reactivity of hydroxyl groups in the acetalization of poly(vinyl alcohol) with butanal. Polym. Sci. Ser. B 54, 464–471 (2012). https://doi.org/10.1134/S1560090412090047

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  • DOI: https://doi.org/10.1134/S1560090412090047

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