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Received June 5, 2014
Accepted August 10, 2014
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Thermal curing and degradation kinetics of terpolymer resins derived from vanillin oxime, formaldehyde and p-chloro-/p-methylacetophenone
Department of Chemistry, B. N. P. G. College, Udaipur - 313001, Rajasthan, India
narendrapalsingh14@gmail.com, rajveerchauhan14@gmail.com
Korean Journal of Chemical Engineering, March 2015, 32(3), 552-562(11), 10.1007/s11814-014-0230-0
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Abstract
A novel class of linear terpolymer resins have been prepared from various macromers formed by vanillin oxime (VO), formaldehyde (F) and p-chloro/p-methylacetophenone in the presence of an acid as catalyst by convenient polycondensation process. The conversion of different macromers into respective terpolymeric resin was studied by DSC analysis from -50 ℃ to 250 ℃. The first thermal transition endotherms ranging from 108-137 ℃ (VOFCA) and 125-150 ℃ (VOFMA) are due to expulsion of water molecules, and the second thermal transition exotherms 177-247 ℃ (VOFCA) and 183.9-249.8 ℃ (VOFMA) are attributed to the formation of methylene linkage between macromers moieties by utilizing methlol groups at terminals. The activation energy required for conversion of methylol into methylene groups for VOFCA and VOFMA was 3.4 and 3.9 kJ/mol, respectively. Structural confirmations were determined through IR, Uv-Vis, 1H NMR spectroscopy and GPC data. The activation energy (Ea) and thermodynamic parameters of the thermal decomposition process were investigated with thermogravimetric analysis (TGA) by isoconversional integral Kissinger-Akahira-Sunose (KAS) and differential Friedman methods. Empirical kinetic models, as well as generalized master plots, were applied to explain the degradation mechanisms of terpolymer resins. The degradation reaction follows Avrami-Erofeev (nucleation and growth) at initial stage to Jander (three-dimensional diffusion) model for PVOMAF and Jander (two-dimensional diffusion) for PVOFCA governed mechanisms. Among all the tested_x000D_
terpolymers, both resins revealed better activity compared to standard drugs as Gentamycin, Amphicilin, Chloramphenicol, Ciprofloxacin and Noorfloxacin.
Keywords
References
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Gandini A, Green Chem., 13, 1061 (2011)
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Chauhan NPS, Kataria P, Chaudhary J, Ameta SC, Int. J. Polym. Mater., 61, 57 (2012)
Chauhan NPS, Des. Monomers Polym., 15, 587 (2012)
Joseph FS, Joshua MS, John JLS, Kaleigh HR, Richard PW, Green Chem., 14, 2346 (2012)
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Yao F, Wu QL, Lei Y, Guo WH, Xu YJ, Polym. Degrad. Stab., 93, 90 (2008)
Alonso MV, Oliet M, Dominguez JC, Rojo E, Rodriguez F, J. Therm. Anal. Calorim., 105, 349 (2011)
Perez JM, Fernandez A, J. Appl. Polym. Sci., 123(5), 3036 (2012)
Dominguez JC, Alonso MV, Oliet M, Rojo E, Rodriguez F, Thermochim. Acta, 498(1-2), 39 (2010)
Chauhan NPS, Ameta SC, Polym. Degrad. Stab., 96, 1420 (2011)
Chauhan NPS, J. Therm. Anal. Calorim., 110, 1377 (2012)
Chauhan NPS, J. Macromol. Sci. Pure Appl. Chem., 49, 655 (2012)
Chauhan NPS, J. Ind. Eng. Chem., 19(3), 1014 (2013)
Chauhan NPS, Des. Monomers Polym., 17, 176 (2014)
Chauhan NPS, Ameta R, Ameta SC, J. Appl. Polym. Sci., 122(1), 573 (2011)
Malek J, Thermochim. Acta, 200, 257 (1992)
Sbirrazzuoli N, Girault Y, Elegant L, Thermochim. Acta, 249, 179 (1995)
Iyer BD, Mathakiya IA, Shah AK, Rakshit AK, Polym. Int., 49, 685 (2000)
Lein EJ, Hansch C, Anderson SM, J. Med. Chem., 11, 430 (1968)
Zhao WH, Hu ZO, Okubo S, Hara Y, Shimamura T, Antimicrob. Agents Chemother., 45, 1737 (2001)
Gottenbos BG, Van-der Mei HC, Klatter F, Nieuwenhuis P, Busscher HJ, Biomaterials, 24, 2707 (2003)