Organosoluble and light-colored fluorinated polyrimides derived from 5,5′-bis[4-(4-amino-2-trifluoromethylphenoxy)phenyl]-4,7-methanohexahydroindan

A novel bis(ether amine) monomer, 5,5'-bis[4-(4-amino-2-trifluoromethylphenoxy)phenyll-4,7methanohexahydroindan (2), was synthesized through the nucleophilic aromatic substitution reaction of 5,5'-bis(4-hydroxyphenyl)-4,7-methanohexahydroindan with 2-chloro-5-nitrobenzotrifluoride to yield the intermediate dinitro compound, followed by catalytic reduction with hydrazine and Pd/C. A series of polyimides were synthesized from 2 and various aromatic dianhydrides using a standard two-stage process with chemical or thermal imidization of poly(amic acid). All of these polymer films were soluble in amide-type solvents above 10% w/v, had tensile strengths of 97-117 MPa, and the 10% weight loss temperature was above 464 degrees C with their residues exceeding 46% at 800 degrees C in nitrogen. Compared with the non-fluorinated polyimides, the fluorinated series were observed to have lower dielectric constants (2.92-3.28 at 1 MHz) and lower moisture absorptions (0.15-0.43 wt%) as well as lower color intensity and better solubility. (c) 2006 Society of Chemical Industry.