A Study on the Cyclodehydration Reaction Converting Poly(amidoxime)s to Poly(1,2,4-oxadiazole)s

Choi EJ; Jung JC

Korea Polymer Journal, Vol.2, No.2, 80-84, October, 1994

A study was made on the thermal cyclodehydration reaction converting poly(amidoxime)s (PAOs) into the corresponding poly(1,2,4-oxadiazole)s (PODs), The PAOs were prepared by condensation of terephthaloyl chloride with isophthalamidoxime(ID), 2,5-dimethylterephthalamidoxime(DTD) and terephthalamidoxime(TD). The cyclodehydration reaction was found to be an exothermic reaction taking place in a broad range of temperatures between 120 and 320℃ . ID-PAO revealed the highest rate of reaction and DTD-PAO showed that the polymer DTD-POD may not be cyclodehydrated at 300℃ due to termal degradation, while ID-POD and TD-POD were stable enough at that temperature to be heated for cyclization.

[References]

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[1] Barton D, Ollis WD, Comprehensive Org. Chem., The Synthesis and Reactions of Organic Compounds, Vol. 4, p. 102, Pergamon Press (1979)

[2] Timeann F, Krueger P, Chem. Ber., 17, 1685 (1984)

[3] Blomstrom DC, U.S. Patent, 3,044,994, July 17 (1962)

[4] Blomstrom DC, Chem. Abstr., 57, 13990d (1962)

[5] Klein DA, Fouty RA, Macromolecules, 1, 318 (1968)

[6] Overberger CG, Fujimoto S, J. Polym. Sci. B: Polym. Phys., 3, 735 (1965)

[7] Akiyama M, Iwakura Y, Shiraishi S, Imai Y, J. Polym. Sci. B: Polym. Phys., 4, 305 (1966)

[8] Ballauff M, Angew. Chem.-Int. Edit., 28, 253 (1989)

[9] Park SB, Jung JC, Makromol. Chem., 193, 2519 (1992)

[10] Jung JC, Choi EJ, Angew. Makromol. Chem., 197, 73 (1992)

[11] Choi EJ, Jung JC, Polym. J., 24, 121 (1992)

[12] Huisgen R, Tetrahedron Lett., 3, 587 (1961)

[13] Dokoshi N, Bamba Y, Kurihara M, Yoda N, Makromol. Chem., 108, 107 (1967)

[14] Batzill VW, Funke W, Makromol. Chem., 99, 1 (1966)

[15] Jung JC, Park SB, J. Polym. Sci. A: Polym. Chem., 31, 3351 (1993)