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Kinetics of urethane formation from isophorone diisocyanate: The catalyst and solvent effects

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Abstract

The dependence of the kinetic parameters of urethane formation in the reaction between isophorone diisocyanate and alcohols of different structure (n-propanol, isopropanol, propargyl alcohol, 1,3-diazidopropan-2-ol, and phenol) in diluted solutions on the natures of solvent (toluene, carbon tetrachloride) and catalyst (dibutyltin dilaurate, diazobicyclooctane) was found using an original IR spectroscopic procedure. The ratio of the apparent rate constants for the reactions involving the aliphatic and cycloaliphatic NCO groups of isophorone diisocyanate was determined, and the efficiency of catalysis in these reactions was estimated. The reaction conditions under which the difference between the reactivities of isocyanate groups can reach 40 were determined.

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References

  1. Luo, Q., Shen, Y., Li, P., Wang, C., and Zhao, Z., J. Appl. Polym. Chem., 2014, vol. 131, no. 21, p. 40970.

    Article  Google Scholar 

  2. Xu, J., Rong, X., Chi, T., Wang, M., Wang, Y., Yang, D., and Qiu, F., J. Appl. Polym. Chem., 2013, vol. 130, no. 5, p. 3142.

    Article  CAS  Google Scholar 

  3. Ma, G., Guan, T., Hou, C., Wu, J., Wang, G., Ji, X., and Wang, B., J. Coat. Technol. Res., 2015, vol. 12, no. 3, p. 505.

    Article  CAS  Google Scholar 

  4. Wang, H., Zhou, Y., He, M., and Dai, Z., Colloid Polym. Sci., 2015, vol. 293, no. 3, p. 875.

    Article  CAS  Google Scholar 

  5. Koshiba, M., Hwang, K.K.S., Foley, S.K., Yarusso, D.J., and Cooper, S.L., J. Mater. Sci., 1982, vol. 17, no. 5, p. 1447.

    Article  CAS  Google Scholar 

  6. Organic Coatings: Science and Technology, Wicks, Z.W., Jones, F.N., Pappas, S.P., and Wicks, D.A., Eds., Hoboken, N.J.: Wiley, 2007, 3rd ed., p. 231.

  7. Wang, S., Yang, P., Zhao, C., Li, J., and Li, T., Gaofenzi Caliliao Kexue Yu Gongcheng, 2012, vol. 28, no. 3, p. 107.

    Google Scholar 

  8. Ono, H.-K., Jones, F.N., and Pappas, S.P., J. Polym. Sci., Part C: Polym. Lett., 1985, vol. 23, no. 10, p. 509.

    CAS  Google Scholar 

  9. Gogoi, S., Barua, S., and Karak, N., Prog. Org. Coat., 2014, vol. 77, no. 9, p. 1418.

    Article  CAS  Google Scholar 

  10. Yin, W., Zeng, X., Li, X., Ren, B., and Tong, Z., J. Coat. Technol. Res., 2013, vol. 10, no. 1, p. 57.

    Article  Google Scholar 

  11. Han, W., Lin, B., Yang, H., and Zhang, X., J. Appl. Polym. Sci., 2013, vol. 128, no. 6, p. 3891.

    Article  Google Scholar 

  12. Mishra, A.K., Narayan, R., Raju, K.V.S.N., and Aminabhavi, T.M., Prog. Org. Coat., 2012, vol. 74, no. 1, p. 134.

    Article  CAS  Google Scholar 

  13. Karpov, S.V., Perepelitsina, E.O., and Malkov, G.V., Polym. Sci., Ser. B: Polym. Chem., 2014, vol. 56, no. 3, p. 298.

    Article  CAS  Google Scholar 

  14. Han, J.L., Yu, C.H., Lin, Y.H., and Hsieh, K.H., J. Appl. Polym. Sci., 2008, vol. 107, no. 6, p. 3891.

    Article  CAS  Google Scholar 

  15. Lima, V., Pelissoli, N.S., Dullius, J., Ligabue, R., and Einloft, S., J. Appl. Polym. Sci., 2010, vol. 115, no. 3, p. 1797.

    Article  Google Scholar 

  16. Yang, P.F., Yu, Y.H., Wang, S.P., and Li, T.D., Int. J. Polym. Anal. Chem., 2011, vol. 16, no. 8, p. 584.

    Article  CAS  Google Scholar 

  17. Lomolder, R., Plogmann, F., and Speier, P., J. Coat. Technol., 1997, vol. 69, no. 868, p. 51.

    Article  Google Scholar 

  18. Karpov, S.V., Lodygina, V.P., Komratova, V.V., Dzhalmukhanova, A.S., Malkov, G.V., and Badamshina, E.R., Kinet. Catal., 2016, vol. 57, no. 3, p. 319.

    Article  CAS  Google Scholar 

  19. Karpov, S.V., Lodygina, V.P., and Malkov, G.V., J. Appl. Spectrosc., 2014, vol. 81, no. 1, p. 23.

    Article  CAS  Google Scholar 

  20. Stagg, H.E., Analyst, 1946, vol. 71, no. 849, p. 557.

    Article  CAS  Google Scholar 

  21. Weissberger, A., Proskauer, E.S., Riddick, J.A., and Toops, E.E., Organic Solvents: Physical Properties and Methods of Purification, New York: Interscience, 1955, p. 295.

    Google Scholar 

  22. Armarego, W.L.F. and Perrin, D.D., Purification of Laboratory Chemicals, Woburn, Mass.: Butterworth Heinemann, 1996, 4th ed., p. 329.

    Google Scholar 

  23. Werf, C.A.V., Heisler, R.V., and McEwen, W.E., J. Am. Chem. Soc., 1954, vol. 76, no. 5, p. 1231.

    Article  Google Scholar 

  24. Dzhalmukhanova, A.S., Lodygina, V.P., Komratova, V.V., Karpov, S.V., Malkov, G.V., and Badamshina, E.R., J. Appl. Spectrosc., 2015, vol. 82, no. 1, p. 145.

    Article  Google Scholar 

  25. Saunders, J.H. and Frish, K.C., Polyurethanes Chemistry and Technology, vol. 1: Chemistry, New York: Interscience, 1962, p. 129.

    Google Scholar 

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Authors and Affiliations

  1. Institute of Problems of Chemical Physics, Russian Academy of Sciences, Chernogolovka, Moscow oblast, 142432, Russia

    S. V. Karpov, V. P. Lodygina, V. V. Komratova, A. S. Dzhalmukhanova, G. V. Malkov & E. R. Badamshina

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  1. S. V. Karpov
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  2. V. P. Lodygina
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  3. V. V. Komratova
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  4. A. S. Dzhalmukhanova
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  5. G. V. Malkov
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  6. E. R. Badamshina
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Correspondence to S. V. Karpov.

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Original Russian Text © S.V. Karpov, V.P. Lodygina, V.V. Komratova, A.S. Dzhalmukhanova, G.V. Malkov, E.R. Badamshina, 2016, published in Kinetika i Kataliz, 2016, Vol. 57, No. 4, pp. 429–435.

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Karpov, S.V., Lodygina, V.P., Komratova, V.V. et al. Kinetics of urethane formation from isophorone diisocyanate: The catalyst and solvent effects. Kinet Catal 57, 422–428 (2016). https://doi.org/10.1134/S0023158416040066

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  • DOI: https://doi.org/10.1134/S0023158416040066

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