Abstract
2,6-Bis-(2,5-dioxo-tetrahydro-N-(4-carboxyphenyl)pyrrol-3-yl)-pyrrolo[3,4-f]isoindole-1,3,5,7-teraone, a chiral diacid, was prepared from pyromellitic anhydride and L-aspartic acid in a three steps reaction pathway. The polycondensation reactions of the monomer with aromatic diamines were carried out in direct condensation reaction conditions. The synthesized poly(amide-imide)s had inherent viscosities in the range of 0.30–0.80 dl/g. Identification of all of the products were performed by conventional analytical techniques such as TLC, IR and 1H NMR/13C MR spectroscopy. Thermoanalytical techniques (TGA/DSC) showed useful levels of thermal stability, associated with relatively high glass transition temperatures and carbonized residues in excess of 40% at 600°C for the synthesized polymers. Amorphous morphology was obtained based on XRD patterns and DSC traces. The polymers were soluble in a variety of polar organic solvents and afforded transparent and relatively flexible to brittle films by solution casting.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
T. Nakano and Y. Okamoto, Chem. Rev. 101, 4013 (2001).
J. J. L. M. Cornelissen, A. E. Rowan, R. J. M. Nolte, and N. A. J. M. Sommerdijk, Chem. Rev. 101, 4039 (2001).
T. Miyabe, Y. Hase, H. Iida, et al., Chirality 21, 44 (2009).
X. P. Hui, C. A. Chen, K. H. Wu, and H. M. Gau, Chirality 19, 10 (2007).
L. Wu, L. Zheng, L. Zong, et al., Tetrahedron 64, 2651 (2008).
T. Tonoi, W. Zhang, D. P. Curran, and K. Mikami, Chirality 20, 597 (2008).
Y. Okamoto and E. Yashima, Angew. Chem., Int. Ed. Engl. 37, 1020 (1998).
M. Nakagawa, Y. Ikeuchi, and M. Yoshikawa, Polymer 49, 4612 (2008).
T. Nakano, J. Chromatogr., A 906, 205 (2001).
M. Yoshikawa, K. Murakoshi, T. Kogita, et al., Eur. Polym. J. 42, 2532 (2006).
T. Gumi, C. Minguillon, and P. Palet, Polymer 46, 12306 (2005).
G. Qing, T. Sun, Z. Chen, et al., Chirality 21, 363 (2009).
Y. Liu, Q. Miao, S. Zhang, et al., Macromol. Chem. Phys. 209, 685 (2008).
L. Angiolini, T. Benelli, L. Giorgini, et al., Sens. Actuators B 126, 56 (2007).
G. D. Jaycox, Polymer 48, 82 (2007).
L. Angiolini, T. Benelli, F. Mauriello, and E. Salatelli, Macromol. Chem. Phys. 207, 1805 (2006).
E. Abdul-Rahim, F. Sanda, and T. Masuda, J. Polym. Sci., Part A: Polym. Chem. 44, 810 (2006).
D. J. Liaw, C. C. Huang, and W. H. Chen, Polymer 47, 2337 (2006).
E. Hamciuc, I. Sava, M. Bruma, et al., Polym. Adv. Technol. 17, 641 (2006).
D. J. Liaw and W. H. Chen, Polym. Degrad. Stab. 91, 1731 (2006).
S. E. Mallakpour, A. R. Hajipour, and M. R. Zamanlou, J. Appl. Polym. Sci. 85, 315 (2002).
S. E. Mallakpour, A. R. Hajipour, and M. R. Zamanlou, J. Polym. Sci., Part A: Polym. Chem. 41, 1077 (2003).
S. E. Mallakpour and M. R. Zamanlou, J. Appl. Polym. Sci. 91, 3281 (2004).
N. Yamazaki, F. Higashi, and J. Kawabata, J. Polym. Sci., Part A: Polym. Chem. 12, 2149 (1974).
S. M. Bush and M. North, Polymer 39, 933 (1998).
H. Zhao, F. Sanda, and T. Masuda, J. Polym. Sci., Part A: Polym. Chem. 45, 253 (2007).
E. Butta, S. De Petris, V. Ferrosini, and M. Pasquini, Eur. Polym. J. 7, 387 (1971).
P. M. Hergenrother, K. A. Watson, J. J. G. Smith, et al., Polymer 45, 5441 (2004).
Author information
Authors and Affiliations
Corresponding author
Additional information
The article is published in the original.
Rights and permissions
About this article
Cite this article
Zamanloo, M.R., Imanzadeh, G., Mansoori, Y. et al. Novel optically active poly(amide-imide)s derived from L-aspartic acid. Polym. Sci. Ser. B 53, 267–277 (2011). https://doi.org/10.1134/S1560090411050095
Received:
Revised:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1560090411050095