Synthesis and characterization of new soluble polyamides from Acenaphtohydrazinomercaptotriazole diamine
Mighani, Hossein; Kia, Najmeh
Abstract
A diamine Acenaphtohydrazinomercaptotriazole (AHTD) was synthesized in one step from acenaphthoqinone and 4-amino-3-hydrazino-5-mercapto-1,2,4-triazole. The diamin was characterized by FTIR, 1HNMR, 13CNMR and melting point. Diamin was used to prepare novel polyamides. The low temperature solution polycondensation of diamin with tow aromatic and tow aliphatic diacid chlorides afforded diamin-containing polyamides with inherent viscosities of 0.38–0.47 dl/g in DMF at 25 °C. The polyamides were generally soluble in a wide range of solvents such as dimethylformamide(DMF), N-Methylpyrolidone(NMP), tetrachloroethane (TCE), dimethylsulfoxide(DMSO) and H2SO4. Thermal analysis showed that these polyamides were practically crustily and with Tg under 100 °C.
Keywords
References
1. Maxwell, J. R., Wasdahl, D. A., Wolfson, A. C., & Stenberg, V. I. (1984). Synthesis of 5-aryl-2H-tetrazoles, 5-aryl-2H-tetrazole-2-acetic acids, and [(4-phenyl-5-aryl-4H-1,2,4-triazol-3-yl)thio]acetic acids as possible superoxide scavengers and antiinflammatory agents. Journal of Medicinal Chemistry, 27(12), 1565-1570. http://dx.doi.org/10.1021/jm00378a007. PMid:6094808.
2. Vicentini, C. B., Manfrini, M., Veronese, A. C., & Guarneri, M. (1998). Synthesis of 4-(pyrazol-5-yl)-1,2,4-triazole-3-thiones. Journal of Heterocyclic Chemistry, 35(1), 29-32. http://dx.doi.org/10.1002/jhet.5570350106.
3. Couderchet, M., Schmalfuß, J., & Böger, P. (1998). A specific and sensitive assay to quantify the herbicidal activity of chloroacetamides. Pesticide Science, 52(4), 381-387. http://dx.doi.org/10.1002/(SICI)1096-9063(199804)52:4<381::AID-PS735>3.0.CO;2-8.
4. Cassidy, P. E. (1980). Thermally stable polymers. New York: Marcel Dekker.
5. Imai, Y., Maldar, N. N., & Kakimoto, M. (1984). Synthesis and characterization of soluble aromatic polyazomethines from 2,5-bis(4-aminophenyl)-3,4 diphenylthiophene and aromatic dialdehydes. Journal of Polymer Science: Polymer Chemistry Edition, 22(12), 3771-3778. http://dx.doi.org/10.1002/pol.1984.170221214.
6. Liaw, D.-J., Uexama, N., & Havada, A. (2004). In N. Ueyama & A. Harada (Eds.), Macromolecules nanostructured materials (chap. 2.2, pp. 80). Berlin: Springer.
7. Liaw, D.-J. (2005). Optically high transparency and light color of organosoluble polyamides containing trifluoromethyl and kink diphenylmethylene linkage. Journal of Polymer Science. Part A, Polymer Chemistry, 43(19), 4559-4569. http://dx.doi.org/10.1002/pola.20782.
8. Liaw, D.-J., Huang, C. C., & Chen, W. H. (2006). Color lightness and highly organosoluble fluorinated polyamides, polyimides and poly(amide–imide)s based on noncoplanar 2,2′-dimethyl-4,4′-biphenylene units. Polymer, 47(7), 2337-2348. http://dx.doi.org/10.1016/j.polymer.2006.01.028.
9. Wu, S.-C., & Shu, C. F. (2003). Synthesis and properties of soluble aromatic polyamides derived from 2,2′-bis(4-carboxyphenoxy)-9,9′-spirobifluorene. Journal of Polymer Science. Part A, Polymer Chemistry, 41(8), 1160-1166. http://dx.doi.org/10.1002/pola.10657.
10. Yang, C.-P., Hsiao, S.-H., & Lin, J.-H. (1992). New poly(amide-imide)s syntheses. II. Soluble poly(amide-imide)s derived from 2,5-bis(4-aminophenyl)-3,4-diphenylthiophene and various N-(ω-carboxyalkyl)-trimellitimides, N-(carboxyphenyl)trimellitimides, or N,N″-bis(ω-carboxyalkyl)pyromellitimides. Journal of Polymer Science. Part A, Polymer Chemistry, 30(9), 1865-1872. http://dx.doi.org/10.1002/pola.1992.080300909.
11. Siracusa, G., Pollicino, A., & Borrello, G. M. (1997). The preparation by a solid-solid interaction route of aromatic polyamide materials containing sulphone, ether and ketone linkages. Journal of Thermal Analysis and Calorimetry, 50(4), 633-646. http://dx.doi.org/10.1007/BF01979035.
12. Fujimura, T., Sarugaku, N., Tsuchiya, M., Ishimaru, K., & Kojima, T. (2001). Thermogravimetric Analysis of Aromatic Polyamides with Various Benzimidazolyl Contents. Journal of Thermal Analysis and Calorimetry, 64(2), 425-431. http://dx.doi.org/10.1023/A:1011516804961.
13. Ghaemy, M., Mighani, H., & Alizadeh, R. (2011). Synthesis and characterization of Schiff-base-containing polyamides. Chinese Journal of Polymer Science, 29(2), 148-155. http://dx.doi.org/10.1007/s10118-010-1004-8.
14. Ghaemy, M., & Mighani, H. (2010). Synthesis and characterization of Schiff-base-containing polyimides. Journal of Applied Polymer Science, 118(5), 2496-2501. http://dx.doi.org/10.1002/app.31178.
15. Ghaemy, M., Mighani, H., & Ziaei, P. (2009). Synthesis and characterization of novel organosoluble polyesters based on a DIOL with azaquinoxaline ring. Journal of Applied Polymer Science, 114(6), 3458-3463. http://dx.doi.org/10.1002/app.30726.
Facebook
Google+
Twitter
LinkedIn
Mendeley
StumbleUpon
CiteULike
Reddit
Email