Phthalimide → Phthalamic acid

HRID 1276584Notes

Reaction equation

HRID 1276584 reaction equation
[C:1]1(=[O:11])[NH:5][C:4](=[O:6])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[O:12](C1C=C(C=CC=1)N)C1C=CC(N)=CC=1.NC1C=C(C=CC=1)OC1C=CC=C(OC2C=CC=C(N)C=2)C=1.C1C(C(C2C=CC3C(OC(=O)C=3C=2)=O)=O)=CC2C(OC(=O)C=2C=1)=O.C1(=O)OC(=O)C2=CC=CC=C12>CN1CCCC1=O>[CH:8]1[CH:7]=[C:3]([C:4]([NH2:5])=[O:6])[C:2]([C:1]([OH:11])=[O:12])=[CH:10][CH:9]=1

Participants

7

Reactant 5

HCID 6809PhthalimideHCID 6811Phthalic AnhydrideHCID 66342Benzenamine, 3,3'-(1,3-phenylenebis(oxy))bis-HCID 754984,4'-Carbonyldiphthalic anhydrideHCID 758713-(4-Aminophenoxy)aniline

Product 1

HCID 6957Phthalamic acid

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent2×

Conditions

Temperature
25 °C

Procedure

The following example illustrates the synthesis of a phthalimide-terminated imide oligomer with theoretical number average molecular weight of 12,000 g/mole. 3,4'-Oxydianiline (3,4'-ODA) (36.00 mmole, 7.2089 g) and 1,3-bis(3-aminophenoxy)benzene (APB) (4.00 mmole, 1.1693 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'-Benzophenone tetracarboxylic dianhydride (BTDA) (38.38 mmole, 12.3673 g) and phthalic anhydride (PA) (3.240 mmole, 0.4799 g) were added to the solution with enough NMP to total 84.9 g (20% solids). The reaction was stirred at 25° C. for 6 h to form the phthalamide acid-terminated polyamide acid. The inherent viscosity (ηinh) of the phthalamide acid-terminated polyamide acid was 0.43 dL/g in NMP at 25° C. To imidize, toluene (40 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 a glass transition temperature could not be detected while a melting endotherm peaked at 392° C. A film cast from the polyamide acid solution and dried 1 hour each at 100, 225, and 371° C. had a Tg of 252° C., a sharp Tm at 394° C. and was brittle.

Workup

  1. customterminated imide oligomer with theoretical number average molecular weight of 12,000 g/mole
  2. customequipped with a mechanical stirrer, condenser and nitrogen inlet

Sources & evidence

ORD record
ord-c9b2831f1d424b24ae1df216b3f5fa16
Source dataset
uspto-grants-2000_12
Patent number
US06166174

Reaction notes

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