Abstract
A novel fluorinated diamine monomer, 3,3-bis[4-(4-amino-2-trifluoromethylphenoxy)phenyl]phthalide (II), was prepared through the nucleophilic substitution reaction of 2-chloro-5-nitrobenzotrifluoride with phenolphthalein in the presence of potassium carbonate to yield the intermediate dinitro compound I, followed by catalytic reduction with hydrazine and Pd/C. Polyimides V were synthesized from diamine II and various aromatic dianhydrides IIIa–f via thermal or chemical imidization of poly(amic acid)s. These polymers had inherent viscosities ranging from 0.63 to 0.95 dL/g and were soluble in a variety of organic solvents. Va–f films had tensile strengths of 105–125 MPa, elongations to break of 9–12%, and initial modulus of 2.35–2.65 GPa. The glass transition temperatures of these polymers were recorded 259–320 °C, and no significant weight loss was observed below a temperature of 500 °C in nitrogen or in air. Compared with nonfluorinated homologues VI, V showed better solubility and lower color intensity, dielectric constant (2.70–3.11 at 1 MHz), and moisture absorption (0.12–0.27 wt %). In particular, Vc–f afforded lightly colored films, which had cutoff wavelengths lower than 380 nm and yellowness index (b* values) ranging from 9 to 25. On comparing thermal imidized polymers with chemical imidized ones, films Va–f(C) showed a lower color intensity than Va–f(H) did.
Similar content being viewed by others
Article PDF
References
C. Feger, M. M. Khojasteh, and M. S. Htoo, Ed., “Advances in Polyimide Science and Technology,” Technomic Publishing, Lancaster, PA, 1993.
M. J. M. Adadie and B. Sillion, Ed., “Polyimides and other High-Temperature Polymers,” Elsevier Biomedical, Amsterdam, 1991.
K. L. Mittal, Ed., “Polyimide: Synthesis, Characterization, and Application,” Vol. I&II, Plemnum, New York, N.Y., 1984.
C. Feger, M. M. Khojasteh, and J. E. McGrath, Ed., “Polyimides, Chemistry and Characterization,” Elsevier Biomedical, Amsterdam, 1989.
P. E. Cassidy, “Thermally Stable Polymers,” Marcel Dekker, New York, N.Y., 1980.
H. H. Yang, “Aromatic High-Strength Fibers,” Wiley, New York, N.Y., 1989.
B. S. Dupont and N. Bilow, U.S. Patent, 4,592,925 (1986).
A. L. Landis and A. B. Naselow, U.S. Patent, 4,645,824 (1987).
K. Higashi and Y. Noda, Eur. Patent, 240249 (1986).
S. Tamai, M. Ohta, S. Kawashima, H. Oikawa, K. Ohkoshi, and A. Yamaguchi, Eur. Patent, 234882 (1987).
T. Matsuura, S. Ando, S. Sasaki, and F. Yamamoto, Electron. Lett., 29, 2107 (1993).
S. Ando, T. Sawada, and Y. Inoue, Electron. Lett., 29, 2143 (1993).
D. Wilson, H. D. Stenzenberger, and P. M. Hergenrother, Ed., “Polyimides,” Black & Son, Glasgow, U.K., 1990.
M. K. Ghosh and K. L. Mittal, Ed., “Polyimides: Fundamentals and Applications,” Marcel Dekker, New York, N.Y., 1996.
F. Li, S. Fang, J. J. Ge, P. S. Honigfort, J. C. Chen, F. W. Harris, and S. Z. D. Cheng, Polymer, 40, 4571 (1999).
F. Li, J. J. Ge, P. S. Honigfort, S. Fang, J. C. Chen, F. W. Harris, and S. Z. D. Cheng, Polymer, 40, 4987 (1999).
C. S. Wang and R. W. Yang, J. Appl. Polym. Sci., 66, 609 (1997).
C. P. Yang and J. H. Lin, J. Polym. Sci., Part A: Polym. Chem., 32, 369 (1994).
C. P. Yang and J. H. Lin, J. Polym. Sci., Part A: Polym. Chem., 32, 423 (1994).
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Yang, CP., Chiang, HC. & Su, YY. Fluorinated Polyimides Based on 3,3-Bis[4-(4-amino-2-trifluoromethylphenoxy)phenyl]phthalide. Polym J 36, 979–991 (2004). https://doi.org/10.1295/polymj.36.979
Published:
Issue Date:
DOI: https://doi.org/10.1295/polymj.36.979
Keywords
This article is cited by
-
Preparation and properties of light-colored and transparent semi-alicyclic polyimide films with enhanced flame retardancy from alicyclic dianhydrides and aromatic diamine containing phenolphthalein unit
Journal of Polymer Research (2021)
-
In situ synthesis and preparation of TiO2/polyimide composite containing phenolphthalein functional group
Journal of Materials Science: Materials in Electronics (2017)
-
Synthesis and characterization of organosoluble polyamides from quinoxaline based diamine
Chinese Journal of Polymer Science (2010)