Light-colored fluorinated polyimides based on 2,5-bis(4-amino-2-trifluoromethylphenoxy)biphenyl and various aromatic dianhydrides

• Published in: Journal of applied polymer science 2006-12, Vol.102 (5), p.4101-4110
• Main Authors: Yang, Chin-Ping, Su, Yu-Yang, Chen, Yung-Chung
• Format: Article
• Language: English
• Subjects: Applied sciences; Exact sciences and technology; fluorinated bis(ether amine); Organic polymers; Physicochemistry of polymers; polyimides; Polymers with particular properties; Preparation, kinetics, thermodynamics, mechanism and catalysts; solubility; thermal stability; transparency
• ISSN: 0021-8995; 1097-4628
• DOI: 10.1002/app.24118

A novel trifluoromethyl‐containing aromatic diamine monomer, 2,5‐bis (4‐amino‐2‐trifluoromethylphenoxy)biphenyl (2), was prepared through the nucleophilic substitution reaction of 2‐chloro‐5‐nitrobenzotrifluoride and phenylhydroquinone in the presence of potassium carbonate to yield the intermediate dinitro compound (1), followed by catalytic reduction with hydrazine and Pd/C. A series of fluorinated polyimides (code 5a–f) were synthesized from diamine (2) with six commercially available aromatic dianhydrides using a standard two‐stage process with thermal or chemical imidization of poly(amic acid). Most of fluorinated polyimides showed good solubility at a concentration of 5–10 wt % and even in pyridine and dioxane. For improving solubility of 5c, copolyimides (5c/a–f) were also prepared from 2 and a pair of dianhydrides (3c/a–f), which were mixed in the molar ratio 1:1. All the polyimide films had a tensile strength in the range from 73 to 112 MPa, an elongation at break within a range of 9–23%, and an initial modulus in the range of 1.6–2.2 GPa. These polyimides exhibited glass transition temperatures of 220–267°C and showed no significant decomposition below 500°C under either nitrogen or air atmosphere. In comparison with the analogous nonfluorinated polyimides based on 2,5‐bis (4‐aminophenoxy) biphenyl (2′), the fluorinated polyimides showed better solubility as well as reduced color intensity, lower dielectric constant, and moisture absorption. © 2006 Wiley Periodicals, Inc. J Appl Polym Sci 102: 4101–4110, 2006