Polyaramide-Imide from N-Phenylphthalimide-Containing Diamine and Dicarboxylic Acid I. Synthesis and Thermal Properties

N-Phenylphthalimide를 포함하는 디아민과 디카르복시산으로 제조된 폴리아라미드-이미드 I. 제조와 열적 성질

  • Received : 1998.08.31
  • Accepted : 1998.09.30
  • Published : 1999.02.10

Abstract

Imide-containing diamine and dicarboxylic acid monomers, N-(4-aminophenyl)-4-aminophthalimide(APAP), N-(4-carboxyphenyl)-4-carboxyphthalimide(CPCP), N,N'-oxydiphenylenebis(4-aminophthalimide)(ODPAP) and N,N'-oxydiphenylenebis(4-carboxyphthalimide)(ODPCP) were prepared. Poly(amide-imide)s were prepared by condensation reaction of the diamine and the dicarboxylic acid monomers. Poly(amide-imide)s were also prepared from the diamine monomers and aromatic acid chlorodes such as terephthaloyl chloride and isophthaloyl chloride. The polymers possess inherent viscosity of 0.18~0.67 dL/g and brittle films were cast from NMP/LiCl solution. The poly(amide-imide)s are easily soluble in NMP/LiCl and also partially soluble in polar aprotic solvents such as DMF, DMSO, NMP and DMAc even at $80^{\circ}C$. DSC traces of polymers showed no glass transition temperature and melting temperature, and TGA traces showed a 10% weight loss at $500^{\circ}C$.

Imide 단위를 포함하는 diamine과 dicarboxylic acid 단량체들, N-(4-aminophenyl)-4-aminophthalimide(APAP), N-(4-carboxyphenyl)-4-carboxyphthalimide(CPCP), N,N'-oxydiphenylenebis(4-aminophthalimide)(ODPAP), 그리고 N,N'-oxydiphenylenebis(4-carboxy-phthalimide)(ODPCP)를 합성하였다. 상기 디아민을 포함한 단량체들과 디카르복시산을 포함한 단량체들을 서로 축합반응하여 imide 단위가 교대로 치환된 poly(imide-amide)s를 합성하였다. 또한 imide단위를 포함하는 diamine 단량체들과 terephthaloyl chloride, 그리고 isophthaloyl chloride를 축합하여 poly(imide-amide)s들도 합성하였다. 이렇게 합성된 중합체들은 NMP/LiCl용액에 매우 잘 용해하였으나 그밖에 극성 비양자성 극성 용매인 DMF, DMSO, 그리고 DMAc 등에는 $80^{\circ}C$에서도 작은 용해도를 보여주었다. 그밖에 고유점도는 0.18~0.67 dL/g를 보여주었으며 NMP/LiCl 용액으로부터 단단하고 부서지기 쉬운 막이 형성되었다. 중합체들은 $500^{\circ}C$ 이하에서 유리 전이 온도 및 융점은 관찰되지 않았으며 열 중량 분석에서 10% 중량 감량은 $500^{\circ}C$ 부근에서 나타나 우수한 열적 성질을 보여주었다.

Keywords

Acknowledgement

Supported by : 단국대학교

References

  1. Modern Plastic Encyclopedia B. L. Dickenson
  2. Comprehensive Polymer Science v.5 G. Allen;J. C. Bevington
  3. Eur. Polym. J. v.16 P. Honore;G. Deleens;E. Marechal
  4. Angew. Chem. Int. Ed. Engl. v.15 K. Friedrich;J. Rieser
  5. Makromol. Chem., Rapid Commun. v.11 H. R. Kricheldorf;R. Hunter
  6. Makromol. Chem. v.184 K. Kurita;S. Matsuda
  7. Makromol. Chem. v.191 H. R. Kricheldorf;G. Schwarz;J. De la Abazo;J. De Campa
  8. Makromol. Chem. v.189 H. R. Kricheldorf;V. Doring;V. Eckhardt
  9. Polymer v.30 H. R. Kricheldorf;W. Nowatzky;G. Schwarz
  10. Macromolecules v.24 H. R. Kricheldorf;A. Domschke;G. Schwarz
  11. J. Polym. Sci.: Part A: Polym. Chem. v.28 S-H. Hsiao;C-, P. Yang
  12. J. Polym. Sci.: Part A: Polym. Chem. v.28 S-H. Hsiao;C-, P. Yang
  13. J. Polym. Sci. Polym. Chem. Ed. v.16 K. Kurita;H. Itoh;Y. Iwakura