Phthalic Anhydride → Phthalamic acid

Temperature

25 °C

The following example illustrates the synthesis of a phthalimide-terminatedimide polymer with theoretical number average molecular weight of 11,600 g/mole. 3,4'-Oxydianiline (ODA) (25.0 mmole, 5.0062 g) and 1,3-bis(3-aminophenoxy)benzene (APB) (25.0 mmole, 7.3084 g) were dissolvedin 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) (47.87 mmole, 14.0845 g) and phthalic anhydride (PA) (4.260 mmole, 0.6310 g) were slurried in NMP (~ 35 mL) and were added to the solution. Afterwashing with ~ 38 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 0.41 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 to 25° C., the polymer was still soluble. The solution was poured into water to precipitate a powder which was washed twice in water and dried at >100° C. to afford a yellow solid in high yield. The resulting phthalimide-terminated polyimide was soluble in NMP and had a glass transition temperature of 219° C. A film cast from the polyamide acid solution and dried one hour each at 100°, 225°, and 371° C. had a Tg of 223° C. and was tough and creasible.

1. customequipped with a mechanical stirrer, condenser and nitrogen inlet
2. additionwere added to the solution
3. customan exotherm of 10°-15° C.

ORD record

ord-5a9f00a3dc0a4f5fa04557306039cd5d

Source dataset

uspto-grants-1999_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05866676