Phthalic Anhydride → Phthalamic acid

Participants

Reaction Conditions

Reaction Steps

The following example illustrates the synthesis of a phthalimide-terminatedimide polymer with theoretical number average molecular weight of 23,400 g/mole. 3,4'-Oxydianiline (ODA) (42.5 mmole, 8.5105 g) and 1,3-bis(3-aminophenoxy)benzene (APB) (7.5 mmole, 2.1925 g) were dissolved in N-methylpyrrolidinone (NMP) ( ~ 35 mL) in a flask equipped with a mechanical stirrer, condenser and nitrogen inlet. 3,3',4,4'-Biphenyl tetracarboxylic dianhydride (BPDA) (49.0 mmole, 14.4170g) and phthalic anhydride (PA) (2.0 mmole, 0.2962 g) were slurried in NMP (~ 35 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 hours to form the phthalamide acid-terminated polyamide acid. The inherent viscosity (ninh) of the phthalamide acid-terminated polyamide acid was 0.68 dL/g in NMP at 25° C. To imidize, toluene (30 mL) was added and the reaction was heated at 160° C. for 24 hours. After cooling, a powder precipitated which was washed twice in water and dried to afford a yellow solid in high yield. The resulting phthalimide-terminated polyimide was insoluble in NMP and had a glass transition temperature 248° C. A film cast from the polyamide acid solution and dried one hour each at 100°, 225°, and 371° C. had a Tg of 252° C. and was tough and creasible.

Provenance & Evidence