사각산으로부터 유도된 고분자의 합성과 그들의 물성

이봉구; 김정수

Polymer(Korea), Vol.19, No.5, 652-658, September, 1995

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사각산으로부터 유도된 고분자의 합성과 그들의 물성

Synthesis of Polymers Derived from Squaric Acid and Their Properties

이봉구, 김정수

초록

사각산 및 사각산 에스테르와 디아민과의 축합반응에 의하여 폴리사각산아미드를 중합하였다. 또 사각산아미드를 테레프탈산 염소화물이나 아디프산 염소화물과 축합하여 새로운 형의 폴리사각산이미드를 합성하였다. 합성한 고분자는 용해성 실험과 IR, UV/VIS, 열분석을 통하여 구조 및 물성을 관찰하였다. 모든 고분자들은 높은 열안정성을 보였으며 용해성은 일반 극성용매에서도 매우 나빴다. 사각산 단위의 π-전자는 1,3-축합형의 폴리사각산아미드나 폴리사각산이미드들이 1, 2-축합형의 고분자보다 더 비편재화되며, 폴리사각산아미드형의 고분자들이 폴리사각산이미드형의 고분자들보다 더 비편재화 되었다.

Poly(squaryl amides) were synthesized by the condensation reaction of squaric acrid and its ester with diamines. Poly(squaryl imides), as a new form of polymers, were synthesized by the condensation of squaryl amides with terephthaloyl chloride and adipoyl chloride. The solubility of synthesized polymers was tested. The structure and physical properties of polymers were observed with IR, UV/VIS and thermal analysis. All the polymers show high thermal stability but poor solubility in many polar solvents. The poly(squaryl amides) and poly(squaryl imides) of 1,3-condensation type have more delocalized π-electrons in squaric acid moiety than those of 1,2-condensation type. Additionally, the π-electrons are more delocalized in the case of the poly(squaryl amides) than the poly (squaryl imides).

Keywords:squaric acid;poly(squaryl amides);poly(squaryl imides);delocalization;solubility

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[5] West R, Niu HY, J. Am. Chem. Soc., 85, 2586 (1963)

[6] West R, Niu HY, J. Am. Chem. Soc., 85, 2589 (1963)

[7] Akhara J, Bull. Chem. Soc. Jpn., 60, 2268 (1987)

[8] Cohen S, Cohen SG, J. Am. Chem. Soc., 88, 1533 (1966)

[9] Weiss A, Riegler E, Alt I, Bohme H, Robl C, Z. Naturforsch., 41B, 18 (1986)

[10] Wrobleski JT, Brown DB, Inorg. Chem. Acta, 35, 109 (1979)

[11] Merritt VY, Hovel HJ, Appl. Phys. Lett., 29, 414 (1976)

[12] Gauger J, Manecke G, Chem. Ber., 103, 3553 (1970)

[13] Manecke G, Gauger J, Tetrahedron Lett., 3509 (1967)

[14] Manecke G, Gauger J, Tetrahedron Lett., 1339 (1968)

[15] Manecke G, Gauger J, Makromol. Chem., 125, 231 (1969)

[16] Neuse EW, Green BR, Polymer, 15, 339 (1974)

[17] Schmidt AH, Ried W, Synthesis, 1 (1978)

[18] Knorr K, Ried W, Synthesis, 649 (1978)

[19] Schmidt AH, Ried W, Synthesis, 869 (1978)

[20] Griffiths GR, Rowe MD, Webb GA, J. Mol. Structure, 8, 363 (1971)

[21] Neuse EW, Green BR, Holm R, Macromolecules, 8, 730 (1975)

[22] Rabek JF, "Experimental Methods in Polymer Chemistry," pp. 549-581, John Wiley & Sons (1980)