Phthalimide → Phthalamic acid

HRID 1276582Notes

Reaction equation

HRID 1276582 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=CC(N)=CC=1)C1C=CC(N)=CC=1.NC1C=C(C=CC=1)OC1C=CC=C(OC2C=CC=C(N)C=2)C=1.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

6

Reactant 4

HCID 6809PhthalimideHCID 6811Phthalic AnhydrideHCID 75794,4'-Diaminodiphenyl EtherHCID 66342Benzenamine, 3,3'-(1,3-phenylenebis(oxy))bis-

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. 4,4'-Oxydianiline (4,4'-ODA) (20.00 mmole, 4.0049 g) and 1,3-bis(3-aminophenoxy)benzene (APB) (20.00 mmole, 5.8467 g) were dissolved in N-methylpyrrolidinone (NMP) (~35 mL) in a flask equipped with a mechanical stirrer, condenser and nitrogen inlet. Pyromellitic dianhydride (PMDA) (38.596 mmole, 8.4187 g) and phthalic anhydride (PA) (2.808 mmole, 0.4159 g) were added to the solution with enough NMP to total 74.8 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 0.50 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 had a glass transition temperature 243° 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. 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-39e050efa1434e5fa30f7e638297f41a
Source dataset
uspto-grants-2000_12
Patent number
US06166174

Reaction notes

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