ABSTRACT The synthesis and characterization of a novel series of soluble polyimides bearing long-chain alkyl groups on their side chains using aromatic diamine monomers such as

_N_-alkyl-3,5-diaminobenzamide (ADBA-X, X = carbon numbers of alkyl chain, 9∼14) and _N_-(3,5-diaminophenyl)-3,4,5-tris(alkoxy)benzamide (DPABA-X, X = 6,12) are described. Polyimides

obtained from 3,3′,4,4′-benzophenonetetracarboxylic dianhydride (BTDA) and ADBA-9∼14 were insoluble, however, copolyimides based on BTDA, ADBA-9∼14, and 4,4′-diaminodiphenylether (DDE) were

soluble. The solubility of these copolyimides may be improved by the entropy effect of long-chain linear alkyl groups as well as the randomizing effect based on copolymerization. The effect

functional diamines are increased as AODB (ether linkage) > ADBP (benzoyl linkage) > ADBA (amide linkage) > DBAE (ester linkage). The polyimides and copolyimides based on BTDA,

DPABA-6 or DPABA-12, and DDE containing 50 mol % or more DPABA were soluble, showing that the effect of DPABA for the enhancement of solubility was larger than ADBA. It is speculated that

the three long-chain alkyl groups in DPABA enhance the solubility of polyimides. Above polyimides and copolyimides were soluble in various polar solvents and exhibited good heat-resistance.

SIMILAR CONTENT BEING VIEWED BY OTHERS CHCL3/TRIETHANOLAMINE: A NEW MIXED SOLVENT FOR PREPARING HIGH-MOLECULAR-WEIGHT MAIN-CHAIN BENZOXAZINES THROUGH MANNICH-TYPE POLYCONDENSATION Article 09

June 2022 DIRECT OBSERVATION OF CYCLIC POLY(_N_-SUBSTITUTED MALEIMIDE)S WITH BROAD SIZE DISTRIBUTIONS SYNTHESIZED BY ANIONIC POLYMERIZATION USING AN N-HETEROCYCLIC CARBENE AND SUCCESSIVE

RING CLOSURE WITHOUT HIGH DILUTIONS Article 22 July 2020 SYNTHESIS OF POLYARYLATES AND ALIPHATIC POLYESTERS BY DIVALENT ACYL-1,2,4-TRIAZOLE: A ROUTE TO METAL-FREE SYNTHESIS AT LOW

TEMPERATURE Article 20 April 2021 ARTICLE PDF REFERENCES * “Polyimides,” K. L. Mittal, Ed., Plenum Press, New York, N. Y., 1984. * “Polyimides,” M. K. Ghosh and K. L. Mittal, Ed., Marcel

Dekker, New York, N. Y., 1996. * D. Yao and P. R. Sundrarajan, _Eur. Polym. J._, 42, 302 (2006). * H. Li, J. Liu, K. Wang, L. Fan, and S. Yang, _Polymer_, 47, 1443 (2006). * C.-P. Yang,

Y.-Y. Su, and M.-Y. Hsu, _Polym. J._, 38, 132 (2006). * J. K. Park, D. H. Lee, B. J. Song, J. B. Oh, and H. K. Kim, _J. Polym. Sci., Part A: Polym. Chem._, 44, 1326 (2006). * H.-S. Li, J.-G.

Liu, J.-M. Rui, L. Fan, S.-Y. Yang, and H.-S. Li, _J. Polym. Sci., Part A: Polym. Chem._, 44, 2665 (2006). * L. Wang, Z. Zhao, J. Li, and C. Chen, _Eur. Polym. J._, 42, 1266 (2006). * X. Z.

Jin and H. Ishii, _J. Appl. Polym. Sci._, 100, 4240 (2006). * C.-P. Yang, Y.-P. Chen, E.-M. Woo, and S.-H. Li, _Polym. J._, 38, 457 (2006). * C.-P. Yang, Y.-Y. Su, and H.-C. Chiang, _React.

Funct. Polym._, 66, 689 (2006). * Z. Qiu, J. Wang, Q. Zhang, S. Zhang, M. Ding, L. Gao, Z. Qiu, J. Wang, and Q. Zhang, _Polymer_, 47, 8444 (2006). * C.-P. Yang, Y.-Y. Su, and Y.-C. Chen,

_J. Appl. Polym. Sci._, 102, 4101 (2006). * Y. Shao, Y.-F. Li, X. Zhao, X.-L. Wang, T. Ma, and F.-C. Yang, _J. Polym. Sci., Part A: Polym. Chem._, 44, 6836 (2006). * R. Hariharan and M.

Sarojadevi, _Polym. Int._, 56, 22 (2007). * X.-J. Zhao, J.-G. Liu, J.-M. Rui, L. Fan, and S.-Y. Yang, _J. Appl. Polym. Sci._, 103, 1442 (2007). * W. Li, S. Zhang, G. Chen, Q. Zhang, W. Li,

G. Chen, and Q. Zhang, _Polymer_, 48, 3082 (2007). * Z. Qiu, S. Zhang, W. Li, Z. Qiu, and W. Li, _J. Appl. Polym. Sci._, 104, 2395 (2007). * B.-K. Chen, S.-Y. Tsay, and Y.-J. Tsai, _Polym.

Int._, 55, 93 (2006). * C.-H. Lee, H. B. Park, Y. S. Chung, Y. M. Lee, H. B. Park, and B. D. Freeman, _Macromolecules_, 39, 755 (2006). * D.-J. Liaw, C.-C. Huang, and W.-H. Chen, _Macromol.

Chem. Phys._, 207, 434 (2006). * X. Liu, J. Tang, J. Wang, and Y. Gu, _J. Appl. Polym. Sci._, 101, 2255 (2006). * S.-H. Hsiao, Y.-M. Chang, H.-W. Chen, and G.-S. Liou, _J. Polym. Sci., Part

A: Polym. Chem._, 44, 4579 (2006). * R. Hariharan and M. Sarojadevi, _J. Appl. Polym. Sci._, 102, 4127 (2006). * Z. Qiu, G. Chen, Q. Zhang, S. Zhang, Z. Qiu, G. Chen, and Q. Zhang, _Eur.

Polym. J._, 43, 194 (2007). * A. S. Mathews, I. Kim, and S.-C. Ha, _J. Appl. Polym. Sci._, 102, 3316 (2006). * Q. Zhang, G. Chen, S. Zhang, Q. Zhang, and G. Chen, _Polymer_, 48, 2250 (2007).

* S. Cao, Y. Jin, S. Xu, M. Yang, S. Xu, and F. Bai, _Polym. Adv. Technol._, 17, 556 (2006). * C.-P. Yang, Y.-Y. Chen, and S.-H. Hsiao, _J. Appl. Polym. Sci._, 104, 1104 (2007). * X. Wang,

Y. Li, S. Zhang, T. Ma, Y. Shao, and X. Zhao, _Eur. Polym. J._, 42, 1229 (2006). * X. Wang, Y. Li, C. Gong, S. Zhang, and T. Ma, _J. Appl. Polym. Sci._, 104, 212 (2007). * W. Anannarukan, S.

Tantayanon, D. Zhang, F. W. Harris, E. A. Aleman, and D. A. Modarelli, _Polymer_, 47, 4936 (2006). * S. Xu, S. Cao, S. Xu, and M. Yang, _Polymer_, 48, 2241 (2007). * S. Chen, K. Tanaka, H.

Kita, K. Okamoto, and Y. Yin, _Polymer_, 47, 2660 (2006). * Z. Hu, Y. Yin, S. Chen, O. Yamada, K. Tanaka, H. Kita, and K. Okamoto, _J. Polym. Sci., Part A: Polym. Chem._, 44, 2862 (2006). *

Z. Qiu, S. Wu, S. Zhang, Z. Qiu, S. Wu, Z. Li, Z. Li, W. Xing, and C. Liu, _Macromolecules_, 39, 6425 (2006). * Y. Li, R. Jin, Z. Wang, Z. Cui, W. Xing, L. Gao, Y. Li, and Z. Cui, _J. Polym.

Sci., Part A: Polym. Chem._, 45, 222 (2007). * J. R. Sasthav and F. W. Harris, _Polymer_, 36, 4911 (1995). * K.-W. Lee, S.-H. Paek, A. Lien, C. Durning, and H. Fukuro, _Macromolecules_, 29,

8894 (1996). * C. Lee, T.-H. Woo, and M. Lee, _Mol. Cryst. Liq. Cryst._, 316, 205 (1998). * B. S. Ban, Y. N. Rin, and Y. B. Kim, _Liq. Cryst._, 27, 125 (2000). * J.-T. Jung, M.-H. Yi, S.-K.

Kwon, and K.-Y. Choi, _Mol. Cryst. Liq. Cryst._, 333, 1 (1999). * L. Li, J. Yin, Y. Sui, H.-J. Xu, J.-H. Fang, Z.-K. Zhu, and Z.-G. Wang, _J. Polym. Sci., Part A: Polym. Chem._, 38, 1943

(2000). * S. J. Lee, J. C. Jung, S. W. Lee, and M. Ree, _J. Polym. Sci., Part A: Polym. Chem._, 42, 3130 (2004). * Y. Tsuda, Y. Tanaka, K. Kamata, N. Hiyoshi, S. Mataka, Y. Matsuki, M.

Nishikawa, S. Kawamura, and N. Bessho, _Polym. J._, 29, 574 (1997). * Y. Tsuda, K. Etou, N. Hiyoshi, M. Nishikawa, Y. Matsuki, and N. Bessho, _Polym. J._, 30, 222 (1998). * Y. Tsuda, R.

Kuwahara, K. Fukuda, K. Ueno, and J.-M. Oh, _Polym. J._, 37, 126 (2005). * Y. Tsuda, T. Kawauchi, N. Hiyoshi, and S. Mataka, _Polym. J._, 32, 594 (2000). * Y. Tsuda, K. Kanegae, and S.

Yasukouchi, _Polym. J._, 32, 941 (2000). * Y. Tsuda, M. Kojima, and J.-M. Oh, _Polym. J._, 38, 1043 (2006). * Y. Tsuda, R. Kuwahara, and J.-M. Oh, _Trans. Mater. Res. Soc., Japan_, 29, 267

(2004). * Y. Tsuda, T. Yoshida, and T. Kakoi, _Polym. J._, 38, 88 (2005). * J. J. van Gorp, J. A. J. M. Vekemans, and E. W. Meijer, _Mol. Cryst. Liq. Cryst._, 397, 191 (2003). * Y. Oishi, M.

Ishida, H. Takado, M. Yoneyama, M. Kakimoto, and Y. Imai, _J. Polym. Sci., Polym. Chem. Ed._, 28, 1763 (1990). * V. S. K. Balagurusamy, G. Ungar, V. Percec, and G. Johansson, _J. Am. Chem.

Soc._, 119, 1539 (1997). * V. Percec, W.-D. Cho, M. Moeller, S. A. Prokhorova, G. Ungar, and D. J. P. Yeardley, _J. Am. Chem. Soc._, 122, 4299 (2000). * S.-H. Hsiao and T.-L. Huang, _J.

Polym. Res._, 11, 9 (2004). * T. Ozawa, _J. Therm. Anal._, 40, 1379 (1993). * F. M. Rugg, J. J. Smith, and R. C. Bacon, _J. Polym. Sci._, 13, 535 (1954). * J. P. Luongo, _J. Polym. Sci._,

42, 139 (1960). * D. J. Liaw, B. Y. Liaw, J. R. Chen, and C. M. Yang, _Macromolecules_, 32, 6860 (1999). Download references AUTHOR INFORMATION AUTHORS AND AFFILIATIONS * Department of

Biochemistry & Applied Chemistry, Kurume National College of Technology, 1-1-1 Komorino, Kurume, 830-8555, Japan Yusuke Tsuda & Takaaki Matsuda * Advanced Engineering School, Kurume

National College of Technology, 1-1-1 Komorino, Kurume, 830-8555, Japan Manami Kojima * Electronic Chemical Material Division, SAMSUNG Cheil Industries Inc., 332-2, Gochun-Dong, Euiwang-Shi,

Kyoungki-Do, 437-010, Korea Jae Min Oh Authors * Yusuke Tsuda View author publications You can also search for this author inPubMed Google Scholar * Manami Kojima View author publications

You can also search for this author inPubMed Google Scholar * Takaaki Matsuda View author publications You can also search for this author inPubMed Google Scholar * Jae Min Oh View author

publications You can also search for this author inPubMed Google Scholar CORRESPONDING AUTHOR Correspondence to Yusuke Tsuda. RIGHTS AND PERMISSIONS Reprints and permissions ABOUT THIS

ARTICLE CITE THIS ARTICLE Tsuda, Y., Kojima, M., Matsuda, T. _et al._ Soluble Polyimides Based on Long-chain Alkyl Groups _via_ Amide Linkages. _Polym J_ 40, 354–366 (2008).

https://doi.org/10.1295/polymj.PJ2007169 Download citation * Received: 11 October 2007 * Accepted: 16 January 2008 * Published: 04 March 2008 * Issue Date: 01 April 2008 * DOI:

https://doi.org/10.1295/polymj.PJ2007169 SHARE THIS ARTICLE Anyone you share the following link with will be able to read this content: Get shareable link Sorry, a shareable link is not

currently available for this article. Copy to clipboard Provided by the Springer Nature SharedIt content-sharing initiative KEYWORDS * Polyimide * Soluble Polyimide * Amide Linkage * Long

Chain Alkyl Group * Copolymerization * Thermal Stability * Solubility