Synthesis and characterization of novel polyimide from bis-(3-aminophenyl)-4-(trifluoromethyl)phenyl phosphine oxide

A novel diamine, bis-(3-aminophenyl)-4-(trifluoromethyl)phenyl phosphine oxide (mDA3FPPO), containing phosphine oxide and fluorine moieties was prepared via the Grignard reaction from an intermediate, 4-(trifluoromethyl)phenyl diphenyl phosphine oxide, that was synthesized from diphenylphosphinic chloride and 4-(trifluoromethyl)bromobenzene, followed by nitration and reduction. The monomer was characterized by Fourier transform infrared (FTIR), H-1 NMR, P-31 NMR, F-19 NMR spectroscopies; elemental analysis; melting point measurements; and titration and was used to prepare polyimides with a number of dianhydrides such as pyromellitic dianhydride (PMDA), 5,5'-[2,2,2-trifluoro-1-(trifluoromethyl)ethyliden]-bis-1,3-isobenzofuranedione (6FDA), 3,3',4,4'-benzophenone tetracarboxylic dianhydride (BTDA), and 4,4'oxydiphthalic dianhydride (ODPA). Polyimides were synthesized via a conventional two-step route; preparation of polyamic acids, followed by solution imidization, and the molecular weight were controlled to 20,000 g/mol. Resulting polyimides were characterized by FTIR, NMR, DSC, and intrinsic viscosity measurements. Refractive-index, dielectric constant, and adhesive properties were also determined. The properties of polyimides were compared with those of polyimides prepared from 1,1-bis-(4-aminophenyl)-1-phenyl-2,2,2-trifluoroethane (3FDAm) and bis-(3-aminophenyl) phenyl phosphine oxide (mDAPPO). The polyimides prepared from mDA3FPPO provided high glass-transition temperatures (248-311 degreesC), good thermal stability, excellent solubility, low birefringence (0.0030-0.0036), low dielectric constants (2.9-3.1), and excellent adhesive properties with Cu. foils (107 g/mm). (C) 2001 John Wiley & Sons, Inc.