Abstract
Four novel polyurethanes were prepared from 4-{(4-hydroxyphenyl)iminomethyl}phenol by reactions with two aromatic diisocyanates, 4,4′-diphenylmethane diisocyanate and toluene 2,4-diisocyanate, and two aliphatic diisocyanates, isophorone diisocyanate and hexamethylene diisocyanate. The polyurethanes formed were characterized by UV-vis, fluorescence, FT-IR,1H-NMR,13C-NMR, differential scanning calorimetry, thermogravimetry, and X-ray diffraction. The polymers were semi-crystalline and all polymers were soluble in polar aprotic solvents.
Similar content being viewed by others
References
Z. Wirpsza,Polyurethanes: Chemistry, Technology and Applications, Ellis Horwood, London, 1993.
O. Bayer, E. Muller, S. Petersen, H. F. Piepenbrink, and E. Windemuth,Angew. Chem.,62, 57 (1950).
B. K. Kim, J. W. Seo, and H. M. Jeong,Macromol. Res.,11, 198 (2003).
P. P. G. Industries, U. K. Patent 2157702 (1985).
B. Bogdanov, V. Toncheva, E. Schacht, L. Finelli, B. Sarti, and so Scandola,Polymer,40, 3171 (1999).
Y. Frere, L. Danicher, and P. Germain,Eur. Polym. J.,34, 193 (1998).
J. Y. Kwon and H. D. Kim,Macromol. Res.,14, 373 (2006).
S.- H. Kang, D.-C. Ku, J.-H. Lim, Y.- K. Yang, N.- S. Kwak, and T.- S. Hwang,Macromol. Res.,13, 212 (2005).
S. Subramani, J. M. Lee, J. H. Kim, and I. W. Cheng,Macromol. Res.,13, 418 (2005).
B. K. Kim, S. Y. Lee, and M. Xu,Polymer,26, 5781 (1996).
N. R Legge, G. Holden, and H. E. Schroeder,Thermoplastic Elastomers: A comprehensive review, Carl Hansser Verslag, New York, 1987.
G. Deleens, P. Foy, and E. Marechal,Eur. Polym. J.,13, 337 (1977).
M. F. Frontini and A. Pavan,J. Appl. Polym. Sci.,48, 2003 (1993).
R. A. Phillips and S. L. Cooper,J. Polym. Sci. Polym. Phys.,34, 737 (1996).
J. T. Koberstein and A. F. Galambos,Macromolecules,25, 5618 (1992).
J. Higgins and C. S. Marvel,J. Polym. Sci. A1,8, 171 (1970).
A. V. Raghu, S. S. Jawalkar, G. S. Gadaginamath, S. B. Halligudi, and T. M. Aminabhavi,J. Polym. Sci. Polym. Chem.,44, 6032 (2006).
A. V. Raghu, G. S. Gadaginamath, N. T. Mathew, S. B. Halligudi, and T. M. Aminabhavi,J. Appl. Polym. Sci.,106, 299 (2007).
A. V. Raghu, G. S. Gadaginamath, N. T. Mathew, S. B. Halligudi, and T. M. Aminabhavi,Reac. Funct. Polym.,67, 503 (2007).
A. V. Raghu, G. Anita, Y. M. Barigaddi, G. S. Gadaginamath, and T. M. Aminabhavi,J. Appl. Polym. Sci.,104, 81 (2007).
A. V. Raghu and H. M. Jeong,J. Appl. Polym. Sci.,107, 3401 (2008).
M. Calvin,J. Am. Chem. Soc.,69, 1886 (1947).
M. Dumitriu, M. Daranga, M. Pastravanu, C. R. Dumitriu, and T. Lixandru,Thermochimica Acta,134, 177 (1988).
M. S. Patel and S. R Patel,J. Polym. Sci. Polym. Chem.,20, 1985 (1982).
X. Li, Y. Jiao, and S. Li,Eur. Polym. J.,27, 1353 (1991).
A. V. Raghu, G. S. Gadaginamath, and T. M. Aminabhavi,J. Appl. Polym. Sci.,98, 2236 (2005).
A. V. Raghu, G. S. Gadaginamath, N. N. Mallikarjuna, and T. M. Aminabhavi,J. Appl. Polym. Sci.,100, 576 (2006).
L. Sacconi, M. Ciampolini, and so Campigli,Inorg. Chem.,4, 407 (1965).
C. Mealares and A. Gandini,Polym. Int.,40, 33 (1996).
D. Evans, T. A. Hicks, W. R. N. Williamson, W. Dawson, S. C. R. Meacock, and E. A. Kitchen,Eur. J. Med. Chem.,31, 635 (1996).
R. W. Seymour and S. L. Cooper,Macromolecules,6, 48 (1973).
T. R. Hesketh, J. W. C. van Bogart, and S. L. Copper,Polym. Eng. Sci.,20, 190 (1980).
C. H. M. Jacques,Polymer Alloys, D. K. Klempner and K. C. Frisch, Eds., Plenum Press, New York, 1977.
J. T. Koberstein and A. F. Galambos,Macromolecules,25, 5618 (1992).
D. J. Martin, G. Meijs, P. A. Fgunatillake, S. J. McCarthy, and G. M. Renvvick,J. Appl. Polym. Sci.,64, 803 (1997).
J. W. C. van Bogart, D. A. Bluemke, and S. L. Cooper,Polymer,22, 1428 (1981).
J. Blackwell and C. D. Lee,J. Polym. Sci. Polym. Phys. Ed.,22, 769 (1984).
S. Mitsuhiro, S. Masakatsu, S. Shinichi, Y. Tomoyuki, and N. Shunji,Macromolecules,24, 6254 (1991).
D. W. van Krevelen, Properties of Polymers, Elsevier, New York, 1990.
Z. Petrovic and J. Ferguson,Prog. Polym. Sci.,16, 695 (1991).
Author information
Authors and Affiliations
Corresponding authors
Rights and permissions
About this article
Cite this article
Raghu, A.V., Jeong, H.M., Kim, J.H. et al. Synthesis and characterization of novel polyurethanes based on 4-{(4-hydroxyphenyl)iminomethyl}phenol. Macromol. Res. 16, 194–199 (2008). https://doi.org/10.1007/BF03218852
Received:
Revised:
Issue Date:
DOI: https://doi.org/10.1007/BF03218852