Khalil FAGHIHI, Meisam SHABANIAN, Mohsen HAJIBEYGI

Synthesis and properties of new optically active and organosoluble poly(ester-imide)s containing L-valine moieties in the main chain by direct polycondensation reaction

New optically active poly(ester-imide)s (PEIs) containing bicyclo[2,2,2]oct-7-ene-2,3,5,6-tetracarboxylic diimide in the main chain were prepared by the reaction of N,N'-(bicyclo[2,2,2]oct-7- ene-2,3,5,6-tetra carboxylic)-bis-L-valine 4 as a diacid monomer with various aromatic diols 5a-g in a system of tosyl chloride (TsCl), pyridine (Py), and N,N-dimethylformamide (DMF). The reactions with TsCl were significantly promoted by controlling alcoholysis with diols, in the presence of catalytic amounts of DMF, to give a series of optically active poly(ester-imide)s. The resulting new polymers were obtained in good yields and inherent viscosities, ranging between 0.36 and 0.62 dL g-1, and were characterized with FT-IR and 1H-NMR spectroscopy, including specific rotation. All of these polymers were highly organosoluble at room temperature in solvents like N,N-dimethylacetamide (DMAc), N,N-dimethylformamide (DMF), dimethylsulfoxide (DMSO), N-methyl-2-pyrrolidone (NMP), and sulfuric acid. The thermal stability of the resulting PEIs was evaluated with thermogravimetric analysis (TGA) and differential scanning calorimetry (DSC) techniques under a nitrogen atmosphere, which indicated that the residual weight percent of the polymers at 600 °C was 43.69%-60.5% and showed that they are moderately thermally stable.

Anahtar Kelimeler:

Poly(ester-imide)s, direct polycondensation, optically active polymers, thermal properties

Synthesis and properties of new optically active and organosoluble poly(ester-imide)s containing L-valine moieties in the main chain by direct polycondensation reaction

Keywords:

Poly(ester-imide)s, direct polycondensation, optically active polymers, thermal properties,

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Ghosh, M. K.; Mittal, K. L. Polyimides: Fundamentals and Applications, Marcel Dekker, New York, 1996.
Cassidy, P. E. Thermally Stable Polymers, Marcel Dekker, New York, 1980.
Saxena, A.; Rao, V. L.; Prabhakaran, P. V.; Ninan, K. N. Eur. Polym. J. 2003, 39, 401-405.
Liaw, D. J.; Liaw, B. Y.; Hsu, P. N.; Hwang, C. Y. Chem. Mater. 2001, 13, 1811-1816.
Mallakpour, S.; Kowsari, E. Polym. Advan. Technol. 2006, 17, 174-179.
Faghihi, K.; Gholizadeh, M. Turk. J. Chem. 2009, 33, 87-97.
Faghihi, K.; Absalar, M.; Hajibeygi, M. Turk. J. Chem. 2010, 34, 81-90.
Nasr Isfahani, H.; Faghihi, K.; Izadkhah, A.; Shabanian, M. Turk. J. Chem. 2009, 33, 459-470.
Hajipour, A. R.; Zahmatkesh, S.; Ruoho, A. E. React. Funct. Polym. 2007, 67, 1040-1051.
Behniafar, H.; Jafari, A. J. Appl. Polym. Sci. 2006, 100, 3203-3211.
Cianga, L. Eur. Polym. J. 2003, 39, 2271-2282.
Faghihi, K.; Shabanian, M.; Hajibeygi, M.; Mohammadi, Y. J. Appl. Polym. Sci. 2010, 117, 1184-1192.
Faghihi, K.; Hajibeygi, M.; Shabanian, M. Macromol. Res. 2009, 10, 739-745.
Angiolini, L.; Benelli, T.; Giorgini, L.; Salatelli, E. Polymer 2005, 46, 2424-2432.
Higashi, F.; Mashimo, T. J. Polym. Sci. Polym. Chem. Ed. 1985, 23, 2999-3005.
Higashi, F.; Akiyama, N.; Takashi, I.; Koyama, T. J. Polym. Sci. Polym. Chem. Ed. 1984, 22, 1653-1660.
Mallakpour, S.; Kowsari, E. J. Appl. Polym. Sci. 2006, 101, 455-460.
Mallakpour, S.; Kowsari, E. Polym. Bull. 2005, 55, 51-59.