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.
Article PDF
Similar content being viewed by others
Avoid common mistakes on your manuscript.
References
Luo, Q., Shen, Y., Li, P., Wang, C., and Zhao, Z., J. Appl. Polym. Chem., 2014, vol. 131, no. 21, p. 40970.
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.
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.
Wang, H., Zhou, Y., He, M., and Dai, Z., Colloid Polym. Sci., 2015, vol. 293, no. 3, p. 875.
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.
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.
Wang, S., Yang, P., Zhao, C., Li, J., and Li, T., Gaofenzi Caliliao Kexue Yu Gongcheng, 2012, vol. 28, no. 3, p. 107.
Ono, H.-K., Jones, F.N., and Pappas, S.P., J. Polym. Sci., Part C: Polym. Lett., 1985, vol. 23, no. 10, p. 509.
Gogoi, S., Barua, S., and Karak, N., Prog. Org. Coat., 2014, vol. 77, no. 9, p. 1418.
Yin, W., Zeng, X., Li, X., Ren, B., and Tong, Z., J. Coat. Technol. Res., 2013, vol. 10, no. 1, p. 57.
Han, W., Lin, B., Yang, H., and Zhang, X., J. Appl. Polym. Sci., 2013, vol. 128, no. 6, p. 3891.
Mishra, A.K., Narayan, R., Raju, K.V.S.N., and Aminabhavi, T.M., Prog. Org. Coat., 2012, vol. 74, no. 1, p. 134.
Karpov, S.V., Perepelitsina, E.O., and Malkov, G.V., Polym. Sci., Ser. B: Polym. Chem., 2014, vol. 56, no. 3, p. 298.
Han, J.L., Yu, C.H., Lin, Y.H., and Hsieh, K.H., J. Appl. Polym. Sci., 2008, vol. 107, no. 6, p. 3891.
Lima, V., Pelissoli, N.S., Dullius, J., Ligabue, R., and Einloft, S., J. Appl. Polym. Sci., 2010, vol. 115, no. 3, p. 1797.
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.
Lomolder, R., Plogmann, F., and Speier, P., J. Coat. Technol., 1997, vol. 69, no. 868, p. 51.
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.
Karpov, S.V., Lodygina, V.P., and Malkov, G.V., J. Appl. Spectrosc., 2014, vol. 81, no. 1, p. 23.
Stagg, H.E., Analyst, 1946, vol. 71, no. 849, p. 557.
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.
Armarego, W.L.F. and Perrin, D.D., Purification of Laboratory Chemicals, Woburn, Mass.: Butterworth Heinemann, 1996, 4th ed., p. 329.
Werf, C.A.V., Heisler, R.V., and McEwen, W.E., J. Am. Chem. Soc., 1954, vol. 76, no. 5, p. 1231.
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.
Saunders, J.H. and Frish, K.C., Polyurethanes Chemistry and Technology, vol. 1: Chemistry, New York: Interscience, 1962, p. 129.
Author information
Authors and Affiliations
Corresponding author
Additional information
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.
Rights and permissions
About this article
Cite this article
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
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S0023158416040066