Synthesis and Properties of New Aromatic Polyamides and Polyimides based on 1,4-Bis[N-(4-aminobenzoyl)-N-phenyl]phenylenediamine

Abstract

A new N-phenylated amide (N-phenylamide) unit-containing aromatic diamine, 1,4-bis[N-(4-aminobenzoyl)-N-phenyl]phenylenediamine, was prepared by the condensation of NŃ-diphenyl-1,4-phenylenediamine with 4-nitrobenzoyl chloride, followed by catalytic reduction. Two series of aromatic poly(N-phenylamide-imide)s and poly(N-phenylamide-amide)s with inherent viscosities of 0.25-0.42 and 0.25-0.54 dL g^-1 were prepared by a conventional two-stage method and the direct phosphorylation polycondensation, respectively, from the diamine with various aromatic dianhydrides and aromatic dicarboxylic acids. Some polymers based on rigid dianhydrides and diacids were semi-crystalline and insoluble in organic solvents. The other polymers were amorphous and organosoluble and could afford freestanding or tough films via solution casting. These polyimides and polyamides had glass transition temperatures in the range of 248-267 and 177-198°C, respectively. Decomposition temperatures of the polyimides for 10% weight loss all occurred above 470°C in both nitrogen and air atmospheres.

Keywords

Polyimides polyamides N-phenylated amide linkage 1,4-bis[N-(4-aminobenzoyl)-N-phenyl]phenylenediamine

Get full access to this article

View all access options for this article.

References

[1] Ghosh M K and Mittal K L (eds) 1996 Polyimides: Fundamentals and Applications ( New York: Marcel Dekker )

[2] Wilson D , Stenzenberger H D and Hergenrother P M (eds) 1990 Polyimides: ( New York: Chapman & Hall )

[3] Cassidy P E 1980 Thermally Stable Polymers ( New York: Dekker )

[4] Yang H H 1989 Aromatic High-Strength Fibers ( New York: John Wiley and Sons )

[5] Imai Y 1995 High Perform Polym. 7 337-337

[6] Imai Y , Maldar N N and Kakimoto M 1985 J. Polym. Sci. A: Polym. Chem. 23 1797-1797

[7] Liou G S and Hsiao S H 2001 J. Polym. Sci. A: Polym. Chem. 39 1786-1786

[8] Hsiao S H and Li C T 1998 Macromolecules 31 7213-7213

[9] Liou G S 1998 J. Polym. Sci. A: Polym. Chem. 36 1937-1937

10.

[10] Eastmond G C , Paprotny J and Irwin R S 1999 Polymer 40 469-469

11.

[11] Yang C P , Hsiao S H and Yang H W 1999 Macromol. Chem. Phys. 200 1528-1528

12.

[12] Espeso J F , de la Campa J G , Lozano A E and de Abajo J 2000 J. Polym. Sci. A: Polym. Chem. 38 1014-1014

13.

[13] Harris F W , Feld W A and Lanier L H 1975 J. Appl. Polym. Sci. Appl. Polym. Symp. 26 421-421

14.

[14] Harris F W , Norris S O , Lanier L H , Reinhardt B A , Case R D , Varaprath S , Padaki S M , Torres M and Feld W A 1984 Polyimides: Synthesis, Characterization, and Applications, K L Mittal (ed) ( New York: Plenum ) p 3-3

15.

[15] Imai Y. Maldar, N N and Kakimoto M 1984 J. Polym. Sci. A: Polymi Chem. 22 2189-2189

16.

[16] Imai Y and Kakimoto M 1989 Polym. Plast. Technol. Eng. 28 371-371

17.

[17] Jeong H J , Oishi Y , Kakimoto M and Imai Y 1991 J. Polym. Sci. A: Polym. Chem. 29 39-39

18.

[18] Jeong H J , Oishi Y , Kakimoto M and Imai Y 1991 J. Polym. Sci. A: Polym. Chem. 29 1691-1691

19.

[19] Xie M , Oishi Y , Kakimoto M and Imai Y 1991 J. Polym. Sci. A: Polym. Chem. 29 55-55

20.

[20] Oishi Y , Takado H , Yoneyama M , Kakimoto M and Imai Y 1990 J. Pol/ym. Sci. A: Polym. Chem. 28 1763-1763

21.

[21] Oishi Y , Ishida M , Kakimoto M , Imai Y and Kurosaki, T 1992 J. Polym. Sci. A: Polym. Chem. 30 1027-1027

22.

[22] Greenwood T D , Kahley R A , Wolfe J F , St Clair A and Johnston N J 1980 J. Polym. Sci. Polym. Chem. Ed. 18 1047-1047

23.

[23] lmai Y , Hamaoka N and Kakimoto M 1984 J. Polym. Sci. Polym. Chem. Ed. 22 1291-1291

24.

[24] Oishi Y , Kakimoto M and Imai Y 1987 J. Polym. Sci. A: Polym. Chem. 25 2493-2493

25.

[25] Goyal M , Kakimoto M and Imai Y 1998 J. Polym. Sci. A: Polym. Chem. 36 2193-2193

26.

[26] Yamazaki N , Matsumoto M and Higashi F 1975 J. Polym. Sci. Polym. Chem. Ed. 13 1373-1373