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Synthesis and Deblocking Investigations of Phenol Blocked Aliphatic Isocyanates and Their Application in the Development of Epoxy-Polyurethane Films
Corresponding Author(s) : Sankar Govindarajan
Asian Journal of Chemistry,
Vol. 34 No. 2 (2022): Vol 34 Issue 2
Abstract
Phenol blocked hexamethylenediisocyanate adducts and polyisocyanates were synthesized and their structure was validated by FTIR, 1H & 13C NMR spectroscopy, TGA, DSC and CO2 evolution techniques were used to evaluate the deblocking temperature of blocked isocyanates. Gel time studies of blocked isocyanates with terathane polyol and solubility study of blocked isocyanates with different polyols were conducted to demonstrate the structure-property correlation. Epoxy-polyurethane films were produced utilizing the blocked isocyanates reported in this work with epoxy resin and their structure was verified by ATR Spectroscopy. TGA, DSC, shore A hardness, tensile strength and flexural strength analysis were used to investigate the thermal and mechanical characteristics of these films. The findings of deblocking temperature and gel time revealed that unsubstituted phenol blocked isocyanates and polyisocyanates deblock at lower temperatures and cure for a shorter time period than substituted phenol blocked isocyanates. Thermal and mechanical characteristics of epoxy-polyurethane films based on blocked polyisocyanates are satisfactory.
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M.T. Li, R.S. Yang and L.Y. Yu, Adv. Mater. Res., 648, 15 (2013).
R.L. Briggs, J. Mater. Manufac., 104, 753 (1995).
M. Schink, G. Rix and J.Kirwin, Wire Coating Composition and Process for Producing the Same, US Patent 5854334 A (1995).
M.S. Rolph, A.L.J. Markowska, C.N. Warriner and R.K. O’Reilly, Polym. Chem., 7, 7351 (2016); https://doi.org/10.1039/C6PY01776B
B.K. Bandlish, Sealant Compositions or Coating Mixtures Containing Functional Silane or Siloxane Adhesion Promotors Nonreactive with Blocked Isocyanates, US Patent 4847319A (1989).
J. Mazanek, C. Thiebes, J. Meixner, O. Fleck and H. Muller, Blocked Polyisocyanates, US Patent 7074852B2 (2003).
P. Kamarchik Jr., G.J. McCollum and G.W. Mauer, Novel Blocked Isocyanates and Curable Compositions Containing the Same, US Patent 4824925A (1987).
M.F. Molaire, Blocked Polyisocyanates Incorporating Planar ElectronDeficient Tetracobonylbisimide Moieties, US Patent 7579127B2 (2006).
L.G. Snow, Processes for Preparing Printable and Printed Articles, EP Patent 1699843B1 (2003).
Z.W. Wicks Jr., Prog. Org. Coat., 9, 3 (1981); https://doi.org/10.1016/0033-0655(81)80013-1
D.A. Wicks and Z.W. Wicks Jr., Prog. Org. Coat., 41, 1 (2001); https://doi.org/10.1016/S0300 9440(00)00164-8
G. Sankar and N. Yan, J. Macromol. Sci. A Pure Appl. Chem., 52, 47 (2015); https://doi.org/10.1080/10601325.2014.976748
D.A. Wicks and Z.W. Wicks Jr., Prog. Org. Coat., 43, 131 (2001); https://doi.org/10.1016/S0300 9440(01)00188-6
T.A. Potter, J.W. Rosthanser and H.G. Schmeler, Proceedings of the 11th International Conference on Organic Coatings Science and Technology, Athens, Greece, July 8-12 (1985).
Z.W. Wicks Jr., Prog. Org. Coat., 3, 73 (1975); https://doi.org/10.1016/0300-9440(75)80002-6
D.A. Wicks and Z.W. Wicks Jr., Prog. Org. Coat., 36, 148 (1999); https://doi.org/10.1016/S0300-9440(99)00042-9
G. Sankar and A.S. Nasar, J. Polym. Sci. A Polym. Chem., 45, 1557 (2007); https://doi.org/10.1002/pola.21924
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A.S. Dunn, Eds.: G. Challa, An Introduction of Polymer Chemistry, Ellis Harwood: Prentice Hall, pp. 192 (1993).
J. Hu, Z. Chen, Y. He, H. Huang and X. Zhang, Res. Chem. Intermed., 43, 2799 (2017); https://doi.org/10.1007/s11164-016-2795-1
J. Bently, Eds.: R. Lambourne and T.A. Strivens, Organic Film Formers, Paints and Surface Coatings, Woodhead Publisher: UK, pp. 72-74 (1999).
M. Choi, M.G. Kim, K.I. Jung, T.H. Lee, M. Ha, W. Hyung, H.W. Jung and S.M. Noh, Coatings, 10, 974 (2020); https://doi.org/10.3390/coatings10100974
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K.K. Majumdar, A. Kundu, I. Das and S. Roy, Appl. Organomet. Chem., 14, 79 (2000); https://doi.org/10.1002/(SICI)1099-0739(200002)14:2<79::AIDAOC931>3.0.CO;2-9
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J.M. Hunter and J.E. Lee, Polyamine-Polyisocyanate Reaction Products as Epoxy Resin Curing Agents, EP Patent 0293110A2 (1988).
C. Lou, X. Zhang, Y. Wang, Z. Chen and H. Li, J. Appl. Polym. Sci., 132 (2015); https://doi.org/10.1002/app.41345
M. Harja, M. Barbuta and N. Taranu, Environ. Eng. Manag. J., 8, 1145 (2009);
https://doi.org/10.30638/eemj.2009.167
S. Oprea, J. Mater. Sci., 43, 5274 (2008); https://doi.org/10.1007/s10853-008-2789-5
Y. Shi, W. Ma, J. Wang and J. Mo, J. Macromol. Sci A Pure Appl. Chem., 56, 750 (2019); https://doi.org/10.1080/10601325.2019.1586438
A. Kausar, Eds.: F. Yilmaz, Polyurethane/Epoxy Interpenetrating Polymer Network, Aspects of Polyurethanes, IntechOpen (2017); https://doi.org/10.5772/676