Synthesis of hyperbranched aromatic polyimides via polyamic acid methyl ester precursor

Macromolecules

Volumn 33, Issue 4, 2000, Pages 1111-1114

  Yamanaka, Kazuhiro ^a   Jikei, Mitsutoshi ^a   Kakimoto, Masa Aki ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ESTERS; GEL PERMEATION CHROMATOGRAPHY; INFRARED SPECTROSCOPY; MOLECULAR WEIGHT; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POLYCONDENSATION; POLYMERIZATION; SYNTHESIS (CHEMICAL);

HYPERBRANCHED AROMATIC POLYIMIDES; IMIDIZATION; POLYAMIC ACID METHYL ESTER;

POLYIMIDES;

EID: 0033894225     PISSN: 00249297     EISSN: None     Source Type: Journal    
DOI: 10.1021/ma991327r     Document Type: Article

References (38)

1. Tomalia, D. A.; Naylor, A. M.; Goddard, W. A. G., III. Angew. Chem., Int. Ed. Engl. 1990, 29, 138.
2. Newkome, G. R.; Moorefield, C. N.; Baker, G. R.; Johnson, A. L.; Behera, R. K. Angew. Chem., Int. Ed. Engl. 1991, 30, 1176.
3. Voit, B. I. Acta Polym. 1995, 46, 87.
4. Fréchet, J. M. J.; Hawker, C. J.; Gitsov, I.; Leon, J. W. J. Macromol. Sci.-Pure Appl. Chem. 1996, A33, 1399.
5. Malmström, E.; Hult, A. J. Macromol. Sci.-Rev. Macromol. Chem. Phys. 1997, C37, 555.
6. Kim, Y. H.; Webster, O. W. J. Macromol. Sci.-Rev. Macromol. Chem. Phys. 1990, 112, 4592. Kim, Y. H.; Webster, O. W. Macromolecules 1992, 25, 5561. Kim, Y. H.; Becker-bauer, R. Macromolecules 1994, 27, 1968.
7. Kim, Y. H.; Webster, O. W. J. Macromol. Sci.-Rev. Macromol. Chem. Phys. 1990, 112, 4592. Kim, Y. H.; Webster, O. W. Macromolecules 1992, 25, 5561. Kim, Y. H.; Becker-bauer, R. Macromolecules 1994, 27, 1968.
8. Kim, Y. H.; Webster, O. W. J. Macromol. Sci.-Rev. Macromol. Chem. Phys. 1990, 112, 4592. Kim, Y. H.; Webster, O. W. Macromolecules 1992, 25, 5561. Kim, Y. H.; Becker-bauer, R. Macromolecules 1994, 27, 1968.
9. Johansson, M.; Malmstörm, E.; Hult, A. J. Polym. Sci., Part A: Polym. Chem. 1993, 31, 619. Hawker, C. J.; Lee, R.; Fréchet, J. M. J. J. Am. Chem. Soc. 1991, 113, 4583. Turner, S. R.; Voit, B. I.; Mourey, T. M. Macromolecules 1993, 26, 4617. Kricheldorf, H. R.; Stöber, O. Macromol. Rapid. Commun. 1994, 15, 87. Malmstörm, E.; Johansson, M.; Hult, A. Macromolecules 1995, 28, 1698.
10. Johansson, M.; Malmstörm, E.; Hult, A. J. Polym. Sci., Part A: Polym. Chem. 1993, 31, 619. Hawker, C. J.; Lee, R.; Fréchet, J. M. J. J. Am. Chem. Soc. 1991, 113, 4583. Turner, S. R.; Voit, B. I.; Mourey, T. M. Macromolecules 1993, 26, 4617. Kricheldorf, H. R.; Stöber, O. Macromol. Rapid. Commun. 1994, 15, 87. Malmstörm, E.; Johansson, M.; Hult, A. Macromolecules 1995, 28, 1698.
11. Johansson, M.; Malmstörm, E.; Hult, A. J. Polym. Sci., Part A: Polym. Chem. 1993, 31, 619. Hawker, C. J.; Lee, R.; Fréchet, J. M. J. J. Am. Chem. Soc. 1991, 113, 4583. Turner, S. R.; Voit, B. I.; Mourey, T. M. Macromolecules 1993, 26, 4617. Kricheldorf, H. R.; Stöber, O. Macromol. Rapid. Commun. 1994, 15, 87. Malmstörm, E.; Johansson, M.; Hult, A. Macromolecules 1995, 28, 1698.
12. Johansson, M.; Malmstörm, E.; Hult, A. J. Polym. Sci., Part A: Polym. Chem. 1993, 31, 619. Hawker, C. J.; Lee, R.; Fréchet, J. M. J. J. Am. Chem. Soc. 1991, 113, 4583. Turner, S. R.; Voit, B. I.; Mourey, T. M. Macromolecules 1993, 26, 4617. Kricheldorf, H. R.; Stöber, O. Macromol. Rapid. Commun. 1994, 15, 87. Malmstörm, E.; Johansson, M.; Hult, A. Macromolecules 1995, 28, 1698.
13. Johansson, M.; Malmstörm, E.; Hult, A. J. Polym. Sci., Part A: Polym. Chem. 1993, 31, 619. Hawker, C. J.; Lee, R.; Fréchet, J. M. J. J. Am. Chem. Soc. 1991, 113, 4583. Turner, S. R.; Voit, B. I.; Mourey, T. M. Macromolecules 1993, 26, 4617. Kricheldorf, H. R.; Stöber, O. Macromol. Rapid. Commun. 1994, 15, 87. Malmstörm, E.; Johansson, M.; Hult, A. Macromolecules 1995, 28, 1698.
14. Uhrich, K. E.; Boegeman, S.; Fréchet, J. M. J.; Turner, S. R. Polym. Bull. 1991, 25, 551. Kim, Y. H. Adv. Mater. 1992, 4, 764. Yang, G.; Jikei, M.; Kakimoto, M. Macromolecules 1998, 31, 5964. Yang, G.; Jikei, M.; Kakimoto, M. Macromolecules 1999, 32, 2215. Jikei, M.; Chon, S.; Kakimoto, M.; Kawauchi, S.; Imase, T.; Watanabe, J. Macromolecules 1999, 32, 2061.
15. Uhrich, K. E.; Boegeman, S.; Fréchet, J. M. J.; Turner, S. R. Polym. Bull. 1991, 25, 551. Kim, Y. H. Adv. Mater. 1992, 4, 764. Yang, G.; Jikei, M.; Kakimoto, M. Macromolecules 1998, 31, 5964. Yang, G.; Jikei, M.; Kakimoto, M. Macromolecules 1999, 32, 2215. Jikei, M.; Chon, S.; Kakimoto, M.; Kawauchi, S.; Imase, T.; Watanabe, J. Macromolecules 1999, 32, 2061.
16. Uhrich, K. E.; Boegeman, S.; Fréchet, J. M. J.; Turner, S. R. Polym. Bull. 1991, 25, 551. Kim, Y. H. Adv. Mater. 1992, 4, 764. Yang, G.; Jikei, M.; Kakimoto, M. Macromolecules 1998, 31, 5964. Yang, G.; Jikei, M.; Kakimoto, M. Macromolecules 1999, 32, 2215. Jikei, M.; Chon, S.; Kakimoto, M.; Kawauchi, S.; Imase, T.; Watanabe, J. Macromolecules 1999, 32, 2061.
17. Uhrich, K. E.; Boegeman, S.; Fréchet, J. M. J.; Turner, S. R. Polym. Bull. 1991, 25, 551. Kim, Y. H. Adv. Mater. 1992, 4, 764. Yang, G.; Jikei, M.; Kakimoto, M. Macromolecules 1998, 31, 5964. Yang, G.; Jikei, M.; Kakimoto, M. Macromolecules 1999, 32, 2215. Jikei, M.; Chon, S.; Kakimoto, M.; Kawauchi, S.; Imase, T.; Watanabe, J. Macromolecules 1999, 32, 2061.
18. Uhrich, K. E.; Boegeman, S.; Fréchet, J. M. J.; Turner, S. R. Polym. Bull. 1991, 25, 551. Kim, Y. H. Adv. Mater. 1992, 4, 764. Yang, G.; Jikei, M.; Kakimoto, M. Macromolecules 1998, 31, 5964. Yang, G.; Jikei, M.; Kakimoto, M. Macromolecules 1999, 32, 2215. Jikei, M.; Chon, S.; Kakimoto, M.; Kawauchi, S.; Imase, T.; Watanabe, J. Macromolecules 1999, 32, 2061.
19. Uhrich, K. E.; Hawker, C. J.; Fréchet, J. M. J.; Turner, S. R. Macromolecules 1992, 25, 4583. Uhrich, K. E.; Hawker, C. J.; Fréchet, J. M. J. Polym. Mater. Sci. Eng. 1991, 64, 237.
20. Uhrich, K. E.; Hawker, C. J.; Fréchet, J. M. J.; Turner, S. R. Macromolecules 1992, 25, 4583. Uhrich, K. E.; Hawker, C. J.; Fréchet, J. M. J. Polym. Mater. Sci. Eng. 1991, 64, 237.
21. Chu, F.; Hawker, C. J. Polym. Bull. 1993, 30, 265. Miller, T. M.; Neeman, T. X.; Kwock, E. W.; Stein, S. M. J. Am. Chem. Soc. 1993, 115, 356. Miller, T. M.; Neeman, T. X.; Kwock, E. W.; Stein, S. M. Macromol. Symp. 1994, 77, 35. Shu, C.-F.; Leu, C.-M. Macromolecules 1999, 32, 100.
22. Chu, F.; Hawker, C. J. Polym. Bull. 1993, 30, 265. Miller, T. M.; Neeman, T. X.; Kwock, E. W.; Stein, S. M. J. Am. Chem. Soc. 1993, 115, 356. Miller, T. M.; Neeman, T. X.; Kwock, E. W.; Stein, S. M. Macromol. Symp. 1994, 77, 35. Shu, C.-F.; Leu, C.-M. Macromolecules 1999, 32, 100.
23. Chu, F.; Hawker, C. J. Polym. Bull. 1993, 30, 265. Miller, T. M.; Neeman, T. X.; Kwock, E. W.; Stein, S. M. J. Am. Chem. Soc. 1993, 115, 356. Miller, T. M.; Neeman, T. X.; Kwock, E. W.; Stein, S. M. Macromol. Symp. 1994, 77, 35. Shu, C.-F.; Leu, C.-M. Macromolecules 1999, 32, 100.
24. Chu, F.; Hawker, C. J. Polym. Bull. 1993, 30, 265. Miller, T. M.; Neeman, T. X.; Kwock, E. W.; Stein, S. M. J. Am. Chem. Soc. 1993, 115, 356. Miller, T. M.; Neeman, T. X.; Kwock, E. W.; Stein, S. M. Macromol. Symp. 1994, 77, 35. Shu, C.-F.; Leu, C.-M. Macromolecules 1999, 32, 100.
25. Mathias, L. J.; Carothers, T. W. J. Am. Chem. Soc. 1991, 113, 4043.
26. Hedrick, J. L.; Hawker, C. J.; Miller, R. D.; Tweieg, R.; Srinivasan, S. A.; Trollsås, M. Macromolecules 1997, 30, 7607.
27. Tao, X.; Zhang, Y.; Wada, T.; Sasabe, H.; Watanabe, T.; Miyama, S. Adv. Mater. 1998, 10, 226. Zhang, Y.; Wang, L.; Wada, T.; Sasabe, H. J. Polym. Sci., Part, A. Polym. Chem. 1996, 34, 1359.
28. Tao, X.; Zhang, Y.; Wada, T.; Sasabe, H.; Watanabe, T.; Miyama, S. Adv. Mater. 1998, 10, 226. Zhang, Y.; Wang, L.; Wada, T.; Sasabe, H. J. Polym. Sci., Part, A. Polym. Chem. 1996, 34, 1359.
29. Kricheldorf, H. R.; Holender, O.; Wollheim, T. High Perform. Polym. 1998, 10, 217.
30. Thompson, D. S.; Markoski, L. J.; Moore, J. S. Macromolecules 1999, 32, 4764.
31. Ueda, M.; Kameyama, A.; Hashimoto, K. Macromolecules 1988, 21, 19. Ueda, M.; Mori, H. Macromol. Chem. 1993, 194, 511.
32. Ueda, M.; Kameyama, A.; Hashimoto, K. Macromolecules 1988, 21, 19. Ueda, M.; Mori, H. Macromol. Chem. 1993, 194, 511.
33. 7: C, 66.66; H, 4.56; N, 5.76. Found: C, 66.12; H, 4.56; N, 5.61.
34. 6,100°C) δ 10.10 (s, 1H, amide-H), 6.65-7.86 (m, 11H, Ar-H), 6.23-6.41 (m, 3H, Ar-H), 3.75 (br, 3H, methyl ester) ppm.
35. 6: C, 70.28; H, 3.79; N, 5.85) Found: C, 67.74; H, 3.53; N, 5.55.
36. Gel permeation chromatography (GPC) was performed in DMF containing 0.01 mol/L of lithium bromide as an eluent. The absolute molecular weight was calculated by GPC with a laser light scattering detector. The specific refractive increment (dn/dc) at 690 nm was determined to be 0.168 mL/g.
37. Hawker, C. J.; Fréchet, J. M. J. J. Am. Chem. Soc. 1990, 112, 7638.
38. 6, 100°C) δ 9.60 (s, 4H, amide-H), 7.81-7.96 (m, 3H, Ar-H), 7.55-7.62 (d, 9H, Ar-H), 7.43-7.48 (m, 9H, Ar-H), 7.21-7.24 (m, 5H, Ar-H), 7.01-7.04 (m, 9H, Ar-H), 6.57-6.58 (m, 3H, Ar-H), 6.41-6.42 (m, 6H, Ar-H), 2.00 (s, 12H, acetyl) ppm.