Phthalimide → Phthalamic acid

HRID 1276575노트

반응식

HRID 1276575 반응식
[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.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

참가 물질

6

반응물 4

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

생성물 1

HCID 6957Phthalamic acid

시약·촉매·용매 1

HCID 13387N-methyl-2-pyrrolidone용매2회

반응 조건

온도
25 °C

실험 절차

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) (47.5 mmole, 9.5117 g) and 1,3-bis(3-aminophenoxy)benzene (APB) (2.50 mmole, 0.7308 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) (48.043 mmole, 14.1354 g) and phthalic anhydride (PA) (3.914 mmole, 0.5797 g) were slurried in NMP (~35 mL) and were added to the solution. After washing with ~30 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 0.54 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 at ~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 253° C. and melting endotherms at ~340 and ~373° C. A film cast from the polyamide acid solution and dried 1 hour each at 100, 225, and 371° C. had a Tg of 253° C. and a Tm at 340° C. and 373° C. and was tough and creasible.

후처리

  1. customterminated imide oligomer with theoretical number average molecular weight of 11,600 g/mole
  2. customequipped with a mechanical stirrer, condenser and nitrogen inlet
  3. additionwere added to the solution
  4. washAfter washing with ~30 mL of NMP
  5. customto provide
  6. customan exotherm of 10-15° C.

출처 및 근거

ORD 기록
ord-87ecb1560111423ab633cc3b4bdf071f
출처 데이터셋
uspto-grants-2000_12
특허 번호
US06166174

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