Dicyanovinyl기를 포함하는 폴리아릴레이트의 합성과 그들의 열적 성질

류지헌; 공명선

Polymer(Korea), Vol.20, No.3, 439-446, May, 1996

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Dicyanovinyl기를 포함하는 폴리아릴레이트의 합성과 그들의 열적 성질

Preparation of Dicyanovinyl-Containing Polyarylates and Their Thermal Properties

류지헌, 공명선

초록

Dicyanovinyl기를 포함한 폴리아릴레이트를 terephthaloyl chloride 및 p-bis(1-chloro-2,2-dicyanovinyl)benzene (2)과 alkyl, sulfide, sulfone, ether 그리고 ester 결합을 가진 방향족 디올들과 계면 중합에 의하여 합성하였다. 생성된 중합체들는 고유 점도가 0.24-0.42dL/g이었으며 80℃에서 극성 반양자성 용매인 DMF, DMSO, NMP 및 DMAc 등에 잘 녹았다. Alkyl ether 그리고 ester기를 가진 방향족 디을부터 합성된 중합체는 THF에도 매우 잘 녹았다. 중합체들은 350℃ 부근에서 정점을 이루는 발열 피이크를 보여 주는데 이때 열에 의한 경화 반응이 진행되어 불용성 물질이 형성되었다. 중합체들 6과 7을 제외하고, 거의 모든 중합체가 400∼465℃사이에서 10% 중량 감량을 나타내었으며, 500℃에서 잔사량은 73∼84%로서 열안정성을 보여주었다.

Polyarylates containing dicyanovinyl moiety were prepared by interfacial polymerization of terephthaloyl chloride and p-bis(1-chloro-2,2-dicyanovinyl)benzene (2) with various diphenol derivatives containing alkyl, sulfide, sulfone, ether and ester group. The resulting polymers possessed intrinsic viscosities of 0.24-0.42dL/g and they are easily soluble in polar aprotic solvents such as DMF, DMSO, NMP and DMAc at 80℃. The polymers derived from diphenols with alkyl ether and ester units were even soluble in common organic solvent such as THF. These polymers showed a large exotherm in differential scanning calorimetry and undergo a curing reaction around 350℃ to form insoluble materials. Almost all the polyarylates, except 6 and 7 exhibited a decomposition with 10% weight loss between 400-465℃ in nitrogen and displayed 73∼84% residual weight at 500℃.

Keywords:polyarylate;dicyanovinyl group;thermally curable polymer;thermally stable polymer

[References]

Dickinson BL, "Polyarylate, Modern Plastics Encyclopedia," Vo. 59 (10A), McGraw-Hill, New York (1982)
Conix AJ, U.S. Patent, 3,216,970 (1965)
Temin SC, "Interfacial Synthesis," Vol. 11, Marcel Dekker, Inc., New York (1977)
Wallenfles K, Friedrich K, Rieser J, Angew. Chem.-Int. Edit., 15, 261 (1976)
Moon HS, Kim ST, Gong MS, Makromol. Chem. Rapid Commun., 12, 591 (1991)
Moore JA, Robello DR, Macromolecules, 22, 1084 (1989)
Moore JA, Mehta PG, Polym. Mater. Sci. Eng., 63, 351 (1990)
Moon HS, Kim JS, Kim CB, Gong MS, Polym. J., 25, 193 (1993)
Shin JC, Kim TM, Gong MS, Macromolecules, 28(7), 2212 (1995)
Gong MS, Kim BG, Cho HG, Choi SH, Macromolecules, 26, 6654 (1993)
Gong MS, Kim BG, Kim YS, Polym. J., 26, 1910 (1994)
Gong MS, Kim ST, Moon HS, Macromolecules, 25, 7392 (1992)
Gally G, Nieri P, Ober CK, Makromol. Chem. Rapid Commun., 3, 543 (1982)
Moon SH, Lee SJ, Kim JB, Gong MS, Bull. Korean Chem. Soc., 15, 1809 (1994)
Robello DR, Ph.D. Thesis of Rensselaer Polytechnic Institute (1986)
Brzozowski ZK, Dubczynski J, Petrus J, J. Macromol. Sci.-Chem., A13, 875 (1979)
Tsai HB, Lee YD, J. Polym. Sci. A: Polym. Chem., 25, 1505 (1987)
Kim SY, Mehta PG, Moore JA, Macromolecules, 26, 3504 (1993)

[Referenced By]

[1] Dickinson BL, "Polyarylate, Modern Plastics Encyclopedia," Vo. 59 (10A), McGraw-Hill, New York (1982)

[2] Conix AJ, U.S. Patent, 3,216,970 (1965)

[3] Temin SC, "Interfacial Synthesis," Vol. 11, Marcel Dekker, Inc., New York (1977)

[4] Wallenfles K, Friedrich K, Rieser J, Angew. Chem.-Int. Edit., 15, 261 (1976)

[5] Moon HS, Kim ST, Gong MS, Makromol. Chem. Rapid Commun., 12, 591 (1991)

[6] Moore JA, Robello DR, Macromolecules, 22, 1084 (1989)

[7] Moore JA, Mehta PG, Polym. Mater. Sci. Eng., 63, 351 (1990)

[8] Moon HS, Kim JS, Kim CB, Gong MS, Polym. J., 25, 193 (1993)

[9] Shin JC, Kim TM, Gong MS, Macromolecules, 28(7), 2212 (1995)

[10] Gong MS, Kim BG, Cho HG, Choi SH, Macromolecules, 26, 6654 (1993)

[11] Gong MS, Kim BG, Kim YS, Polym. J., 26, 1910 (1994)

[12] Gong MS, Kim ST, Moon HS, Macromolecules, 25, 7392 (1992)

[13] Gally G, Nieri P, Ober CK, Makromol. Chem. Rapid Commun., 3, 543 (1982)

[14] Moon SH, Lee SJ, Kim JB, Gong MS, Bull. Korean Chem. Soc., 15, 1809 (1994)

[15] Robello DR, Ph.D. Thesis of Rensselaer Polytechnic Institute (1986)

[16] Brzozowski ZK, Dubczynski J, Petrus J, J. Macromol. Sci.-Chem., A13, 875 (1979)

[17] Tsai HB, Lee YD, J. Polym. Sci. A: Polym. Chem., 25, 1505 (1987)

[18] Kim SY, Mehta PG, Moore JA, Macromolecules, 26, 3504 (1993)