Soluble aromatic polyimides based on 2,2-bis(3-amino-4-hydroxyphenyl)hexafluoropropane: Synthesis and properties

Journal of Applied Polymer ScienceVolume 59, Issue 4 p. 725-735 Article Soluble aromatic polyimides based on 2,2-bis(3-amino-4-hydroxyphenyl)hexafluoropropane: Synthesis and properties D. Likhatchev, Corresponding Author D. Likhatchev IIM, UNAM, Apdo. Postal 70–360, Deleg. Coyocan, 04510, MexicoIIM, UNAM, Apdo. Postal 70–360, Deleg. Coyocan, 04510, Mexico===Search for more papers by this authorC. Gutierrez-Wing, C. Gutierrez-Wing IIM, UNAM, Apdo. Postal 70–360, Deleg. Coyocan, 04510, MexicoSearch for more papers by this authorI. Kardash, I. Kardash Karpov Research Institute of Physical Chemistry, Vorontsovo Pole, 10, 103064, Moscow, RussiaSearch for more papers by this authorR. Vera-Graziano, R. Vera-Graziano IIM, UNAM, Apdo. Postal 70–360, Deleg. Coyocan, 04510, MexicoSearch for more papers by this author D. Likhatchev, Corresponding Author D. Likhatchev IIM, UNAM, Apdo. Postal 70–360, Deleg. Coyocan, 04510, MexicoIIM, UNAM, Apdo. Postal 70–360, Deleg. Coyocan, 04510, Mexico===Search for more papers by this authorC. Gutierrez-Wing, C. Gutierrez-Wing IIM, UNAM, Apdo. Postal 70–360, Deleg. Coyocan, 04510, MexicoSearch for more papers by this authorI. Kardash, I. Kardash Karpov Research Institute of Physical Chemistry, Vorontsovo Pole, 10, 103064, Moscow, RussiaSearch for more papers by this authorR. Vera-Graziano, R. Vera-Graziano IIM, UNAM, Apdo. Postal 70–360, Deleg. Coyocan, 04510, MexicoSearch for more papers by this author First published: 24 January 1996 https://doi.org/10.1002/(SICI)1097-4628(19960124)59:4<725::AID-APP18>3.0.CO;2-OCitations: 51AboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Abstract Aromatic polyimides were synthesized from 2,2-bis(3-amino-4-hydroxyphenyl)hexafluoropropane (6F-OH diamine) and different aromatic dianhydrides by a one-step hightemperature polycondensation, or by a two-step procedure using either thermal or chemical imidization of poly(amic acids), PAA. The obtained polyimides were compared in terms of their chemical structure, molecular weight, mechanical and thermal properties. The reaction of 6F-OH diamine with different aromatic dianhydrides in amide solvents at room temperature resulted in the formation of PAA with moderate molecular weight (ηinh ⩽ 0.7 g/dL). The thermal imidization of these PAAs led to brittle hydroxy polyimides (PI-6F-OH). In contrast, chemical imidization of similar PAAs in acetic anhydride and pyridine brought about flexible self-supporting polyimide films. The FTIR analysis indicated that the latter process was accompanied by an esterification of the OH groups in the diamine moieties, resulting in the formation of the polymers with side acetate groups (PI-6F-Ac). The high molecular weight hydroxy polyimides, suitable for preparation of films with good tensile properties, were synthesized by a one-step high-temperature polycondensation in phenolic solvents. All obtained polyimides were well soluble in common organic solvents. The highest solubility was observed for PI-6F-Ac. It was found by means of FTIR and TGA that the polyimides with the R group (R = OH or acetate) in orto position to the nitrogen atom in the diamine moiety underwent a rearrangement to benzoxazoles above 300°C. The starting temperature and conversion of this rearrangement reaction were controlled by the type of R group. The imide-to-benzoxazole rearrangement shifted to lower temperatures, and higher conversion was encountered for the polyimides with side acetate group, PI-6F-Ac, obtained by chemical imidization. © 1996 John Wiley & Sons, Inc. References 1 Y. Oishi, M. Shirasaki, M. Kakimoto, and Y. Imai, J. Polym. Sci., Part A: Polym. Chem., 31, 293 (1993). 2 T. M. Moy and J. E. McGrath, J. Polym. Sci., Part A: Polym. Chem., 32, 1903 (1994). 3 D. Yu, A. Gharavi, and L. Yu, Macromolecules, 28, 784 (1995). 4 D. N. Khanna and W. H. Mueller, Polym. Eng. Sci., 29, 954 (1989). 5 T. Omote, Guo-Jin, K. Koseki, and T. Yamaoka, J. Appl. Polym. Sci., 41, 929 (1990). 6 T. Omote, K. Koseki, and T. Yamaoka, Macromolecules, 23, 4788 (1990). 7 T. Omote, H. Mochizuki, K. Koseki, and T. Yamaoka, Macromolecules, 23, 4796 (1990). 8 B.-C. Ho, Y.-S. Lin, and Y.-D. Lee, J. Appl. Polym. Sci., 53, 1513 (1994). 9 I. Ye. Kardash, A. Ya. Ardashnikov, V. S. Yakubovich, G. I. Braz, A. Ya. Yakubovich, and A. N. Pravednikov, Vyskomol. Soedin., A9, 1914 (1967). 10 I. Ye. Kardash, D. Yu. Likhatchev, N. V. Nikitin, A. Ya. Ardashnikov, N. V. Koslova, and A. N. Pravednikov, Polym. Sci. USSR, 27, 1961 (1985). 11 C. E. Sroog, Prog. Polym. Sci., 16, 561 (1991). 12 R. A. Dine-Hart and W. W. Wright, J. Appl. Polym. Sci., 11, 561 (1967). 13 D. Yu. Likhatchev, M. S. Arzhakov, S. N. Chvalun, Ye. A. Sinevich, Yu. A. Zubov, and I. Ye. Kardash, Vysokomol. Soyed., B27, 723 (1985). 14 A. K. Saini, C. M. Carlin, and H. H. Patterson, J. Polym. Sci., Polym. Chem., 31, 2751 (1993). 15 R. W. Snyder, B. Thomson, B. Bartges, D. Czerniawski, and P. C. Painter, Macromolecules, 22, 4166 (1989). 16 M. L. Wallach, J. Polym. Sci., A-2, 1995 (1969). 17 M. I. Bessonov, M. M. Koton, V. V. Kudryavtsev, and L. A. Laius, Polyimides—Thermally Stable Polymers, Plenum, New York, 1987. 18 D. Likhatchev, L. Alexandrova, M. Tlenkopatchev, R. Vilar, and R. Vera-Graziano, J. Appl. Polym. Sci., 57, 37 (1995). 19 D. Yu. Likhatchev, S. N. Chvalun, Yu. A. Zubov, and I. Ye. Kardash, Polym. Sci. USSR, 33, 2010 (1991). 20 A. P. Simonov, V. P. Bazov, G. I. Braz, N. N. Voznesenskaya, A. Ya. Yakubovich, Khim. Geterotsikl. Soedin., 2, 292 (1970). 21 P. Bassignana, C. Cogrossi, and M. Gandino, Spectrochim. Acta, 19, 1855 (1963). 22 G. F. L. Ehlers, K. R. Fishch, and W. R. Powell, J. Polym. Sci. Symp., 43, 55 (1973). 23 M. Bruma, F. Mercer, B. Schulz, R. Dietel, and W. Neumann, Polym. Adv. Technol., 5, 535 (1994). 24 I. Ye. Kardash, and A. N. Pravednikov, Vysokomol. Soyed., B9, 873 (1967). Citing Literature Volume59, Issue424 January 1996Pages 725-735 ReferencesRelatedInformation