Phthalimide → Phthalamic acid

Participants

Reaction Conditions

Reaction Steps

The following example illustrates the synthesis of a phthalimide-terminated imide oligomer with theoretical number average molecular weight of 11,600 g/mole. 3,4'-Oxydianiline (ODA) (63.75 mmole, 12.7653 g) and 1,3-bis(3-aminophenoxy)benzene (APB) (11.25 mmole, 3.2888 g) were dissolved in N-methylpyrrolidinone (NMP) (~50 mL) in a flask equipped with a mechanical stirrer, condenser and nitrogen inlet. 3,3',4,4'-Biphenyl tetracarboxylic dianhydride (BPDA) (72.0 mmole, 21.1838 g) and phthalic anhydride (PA) (6.0 mmole, 0.8888 g) were slurried in NMP (~50 mL) and were added to the solution. After washing with ~32 mL of NMP to provide a 20% solids content reaction, an exotherm of 10-15° C. was observed. The exotherm quickly subsided and the reaction was stirred at 25° C. for 16 h to form the phthalamide acid-terminated polyamide acid. The inherent viscosity (ηinh)) of the phthalamide acid-terminated polyamide acid was 0.47 dL/g in NMP at 25° C. To imidize, toluene (30 mL) was added and the reaction was heated at 160° C. for 24 h. After cooling, a powder precipitated which was washed twice in water and dried ~230° C. in a vacuum to afford a yellow solid in high yield. The resulting phthalimide-terminated polyimide was insoluble in NMP and had a glass transition temperature 245° C. and a melting point at ~357° C. A film cast from the polyamide acid solution and dried 1 hour each at 100, 225, and 371° C. had a Tg of 248° C. and a Tm at 357° C. and was tough and creasible.

Provenance & Evidence