Microwave Assisted Rapid Synthesis of Novel Optically Active Poly(amide-imide)s Based on N-Trimellitylimido-L-Leucine Diacid Chloride and Hydantoin Derivatives

Khalil Faghihi

Macromolecular Research, Vol.12, No.3, 258-262, June, 2004

Khalil Faghihi^†

Organic Polymer Chemistry Research Laboratory, Department of Chemistry, Faculty of Science, Arak University, Arak 38156, Iran

E-mail:

We have developed facile and rapid polycondensation reactions of N-trimellitylimido-L-leucine diacid chloride 1 with eight different derivatives of hydantoin compounds 2a-h, in the presence of a small amount of a polar organic medium, such as o-cresol, by using a domestic microwave oven. The polycondensation reactions proceeded rapidly they were complete within 7-9 min-to produce a series of novel optically active poly(amide-imide)s (3a-h) in high yield with inherent viscosities of 0.33-0.51 dL/g. We characterized the resulting poly(amide-imide)s by elemental analysis, thermal gravimetric analysis (DSC, TGA, and DTG), and FTIR spectroscopy, and by measuring their viscosities, specific rotations, and solubilities. All of the polymers were soluble at room temperature in polar solvents such as N,N-dimethylacetamide, N,N-dimethylformamide, dimethylsulfoxide, tetrahydrofuran, and N-methyl-2-pyrrolidone.

Keywords:microwave-assisted rapid polycondensation;optically active polymers;poly(amide-imide)s;hydantoin derivatives;N-trimellitylimido-L-leucine diacid chloride.

[References]

Varma SR, Green Chem., 1, 43 (1999)
Gong YD, Sohn HY, Kurth MJ, J. Org. Chem., 63, 4854 (1998)
Bogdal D, Molecules, 4, 333 (1999)
Varma SR, Kumar D, Org. Lett., 1, 697 (1999)
Pylypiw HM, Arsenault TL, Thetford CM, Mattina MJI, J. Agric. Food Chem., 45, 3522 (1997)
Yaylayan VA, Matni G, J. Agric. Food Chem., 45, 149 (1997)
Vazques MJ, Carro AM, Lorenzo RA, Cela R, Anal. Chem., 69, 221 (1997)
Jullien H, Valot H, Polymer, 26, 506 (1985)
Silinski B, Kuzmycz C, Gourdenne A, Eur. Polym. J., 23, 273 (1987)
Imai Y, Nemoto H, Watanabe S, Kakimoto MA, Polym. J., 28, 256 (1996)
Liu YM, Sun XD, Xie XQ, Scola DA, J. Polym. Sci. A: Polym. Chem., 36(14), 2653 (1998)
Mallakpour SE, Hajipour AR, Faghihi K, Polym. Int., 49, 1383 (2000)
Mallakpour SE, Hajipour AR, Faghihi K, Eur. Polym. J., 37, 119 (2001)
Mallakpour SE, Hajipour AR, Faghihi K, Foroughifar N, Bagheri J, J. Appl. Polym. Sci., 80(13), 2416 (2001)
Faghihi K, Zamani K, Mirsamie A, Sangi MR, Eur. Polym. J., 39, 247 (2002)
Faghihi K, Zamani K, Mallakpour S, Polym. Int., in press (2003)
Faghihi K, Zamani K, Mallakpour S, Mirsamie A, J. Appl. Polym. Sci., in press (2003)
Okamoto Y, Nakano T, Chem. Rev., 94(2), 349 (1994)
Farina M, Top Stereochem., 17, 1 (1987)
Ciardelli F, Encycl. Polym. Sci. Eng., 10, 463 (1987)
Wulff G, Angew. Chem.-Int. Edit., 28, 21 (1989)
Fontanille M, Guyot A, Recent Advances in Synthetic and Mechanistic Aspects of Polymerization, Dordrechet, The Netherlands, Kluwer (1987)
Mallakpour SE, Dabbagh HA, Faghihi K, Iranian Polym. J., 9, 41 (2000)
Faghihi K, Zamani K, Mallakpour S, Iranian. Polym. J., 11, 339 (2002)
Kirk-Othmer Encyclopedia of Chemical Technology, Third edition, John Wiley and Sons, New York, Vol. 12, pp. 692-700 (1983)
Mallakpour SE, Hajipour AR, Roohipour-fard R, Eur. Polym. J., 36, 2455 (2000)
Mallakpour SE, Hajipour AR, Vahabi R, Iranian. Polym. J., 10, 321 (2001)
Lamothe M, Lannuzel M, Perez M, J. Comb. Chem., 4, 73 (2002)

[Referenced By]

[1] Varma SR, Green Chem., 1, 43 (1999)

[2] Gong YD, Sohn HY, Kurth MJ, J. Org. Chem., 63, 4854 (1998)

[3] Bogdal D, Molecules, 4, 333 (1999)

[4] Varma SR, Kumar D, Org. Lett., 1, 697 (1999)

[5] Pylypiw HM, Arsenault TL, Thetford CM, Mattina MJI, J. Agric. Food Chem., 45, 3522 (1997)

[6] Yaylayan VA, Matni G, J. Agric. Food Chem., 45, 149 (1997)

[7] Vazques MJ, Carro AM, Lorenzo RA, Cela R, Anal. Chem., 69, 221 (1997)

[8] Jullien H, Valot H, Polymer, 26, 506 (1985)

[9] Silinski B, Kuzmycz C, Gourdenne A, Eur. Polym. J., 23, 273 (1987)

[10] Imai Y, Nemoto H, Watanabe S, Kakimoto MA, Polym. J., 28, 256 (1996)

[11] Liu YM, Sun XD, Xie XQ, Scola DA, J. Polym. Sci. A: Polym. Chem., 36(14), 2653 (1998)

[12] Mallakpour SE, Hajipour AR, Faghihi K, Polym. Int., 49, 1383 (2000)

[13] Mallakpour SE, Hajipour AR, Faghihi K, Eur. Polym. J., 37, 119 (2001)

[14] Mallakpour SE, Hajipour AR, Faghihi K, Foroughifar N, Bagheri J, J. Appl. Polym. Sci., 80(13), 2416 (2001)

[15] Faghihi K, Zamani K, Mirsamie A, Sangi MR, Eur. Polym. J., 39, 247 (2002)

[16] Faghihi K, Zamani K, Mallakpour S, Polym. Int., in press (2003)

[17] Faghihi K, Zamani K, Mallakpour S, Mirsamie A, J. Appl. Polym. Sci., in press (2003)

[18] Okamoto Y, Nakano T, Chem. Rev., 94(2), 349 (1994)

[19] Farina M, Top Stereochem., 17, 1 (1987)

[20] Ciardelli F, Encycl. Polym. Sci. Eng., 10, 463 (1987)

[21] Wulff G, Angew. Chem.-Int. Edit., 28, 21 (1989)

[22] Fontanille M, Guyot A, Recent Advances in Synthetic and Mechanistic Aspects of Polymerization, Dordrechet, The Netherlands, Kluwer (1987)

[23] Mallakpour SE, Dabbagh HA, Faghihi K, Iranian Polym. J., 9, 41 (2000)

[24] Faghihi K, Zamani K, Mallakpour S, Iranian. Polym. J., 11, 339 (2002)

[25] Kirk-Othmer Encyclopedia of Chemical Technology, Third edition, John Wiley and Sons, New York, Vol. 12, pp. 692-700 (1983)

[26] Mallakpour SE, Hajipour AR, Roohipour-fard R, Eur. Polym. J., 36, 2455 (2000)

[27] Mallakpour SE, Hajipour AR, Vahabi R, Iranian. Polym. J., 10, 321 (2001)

[28] Lamothe M, Lannuzel M, Perez M, J. Comb. Chem., 4, 73 (2002)