폴리(프로파길 페닐 에테르)의 합성과 그 특성에 관한 연구

이원철; 갈영순; 류문삼; 한성호; 최삼권

Polymer(Korea), Vol.15, No.3, 283-288, June, 1991

Export Citation

폴리(프로파길 페닐 에테르)의 합성과 그 특성에 관한 연구

Synthesis and Properties of Poly(phenyl propargyl ether)

이원철, 갈영순, 류문삼, 한성호, 최삼권

초록

여러 가지 전이금속촉매를 사용하여 프로파길 페닐 에테르(PPE)를 중합시켰다. MoCl₅계 촉매가 WCl₆계 촉매보다 훨씬 더 효과적이었으며 MoCl₅를 사용한 PPE의 중합에서 (n-Bu)₄Sn이 매우 우수한 조촉매로 밝혀졌다. 본 중합에 적합한 용매는 1,2-디클로로에탄, 톨루엔, 클로로벤젠등이였으며 NMR, IR, UV-visible 분광분석에 의해 합성한 중합체의 구조를 분석한 결과 공액 폴리엔 구조를 가지고 있음을 알 수 있었다. 폴리(PPE)는 벤젠, 클로로벤젠, 클로로포름과 같은 방향성 및 할로겐이 포함된 탄화수소 용매에는 완전히 녹는 반면 메탄올, 개미산, 헥산 등에는 용해하지 않았다. 열중량분석 결과 폴리(PPE)는 200℃까지 안정함을 알 수 있었다.

The polymerization of propargyl phenyl ether(PPE) was carried out by various transition metal catalysts. MoCl₅-based catalysts were more effective than WCl₆-based catalysts. (n-Bu)₄Sn was found the be very effective cocatalyst for the polymerization of PPE by MoCl₅. It was found that 1,2-di-chloroethane, toluene, chlorobenzene are good solvents for this polymerization. The resulting poly (propargyl phenyl ether) [poly(PPE)] structure was identified by NMR, IR, UV-visible spectroscopies to have highly conjugated polyene structure. The poly(PPE) was completely soluble in aromatic and halogenated hydrocarbons such as benzene, chlorobenzene, and chloroform, but insoluble in methanol, formic acid, and hexane. The poly(PPE) was thermally stable up to 200℃.

[References]

Paushkin YM, Vishnyakova TP, Nisova SA, Lunin AF, Omarov OY, Markov YY, Machus FF, Golubera IA, Polak LS, Patalakh II, Stychenko VA, Sokolinskya TA, J. Polym. Sci. A: Polym. Chem., 1(5), 1203 (1967)
Wnek GE, Chien JCW, Karasz FE, Lillya CP, Polymer, 20, 1441 (1979)
Kang ET, Bhatt AP, Villaroel E, Anderson WA, Ehrlich P, J. Polym. Sci. C: Polym. Lett., 20, 143 (1982)
Camus C, Faruffini V, Furlani A, Marsich N, Ortaggi G, Paolesse R, Russo MV, Appl. Org. Chem., 2, 533 (1988)
Masuda T, Higashimura T, Accounts Chem. Res., 17, 51 (1984)
Simionescu CI, Percec V, Prog. Polym. Sci., 8, 133 (1982)
Wegner G, Angew. Chem.-Int. Edit., 20, 361 (1981)
Masuda T, Hasegawa KI, Higashimura T, Macromolecules, 7, 728 (1974)
Gal YS, Cho HN, Choi SK, J. Polym. Sci. A: Polym. Chem., 24, 2021 (1986)
Gal YS, Cho HN, Choi SK, Polym.(Korea), 10(7), 688 (1986)
Okano Y, Masuda T, Higashimura T, Polym. J., 14, 477 (1982)
Chauser MG, Rodionov YM, Misin VM, Cherkashin MI, Russ. Chem. Rev., 45, 348 (1976)
Furlani A, Russo MV, Carusi P, Licoccia S, Leoni E, Valenti GG, Gazz. Chim. Ital., 113, 671 (1983)
Voronkov MG, Pukhnarevich VB, Sushchinskaya SP, Annenkova VZ, Annenkova VM, Andreeva NJ, J. Polym. Sci. A: Polym. Chem., 18, 53 (1980)
Lee WC, Sohn JE, Gal YS, Choi SK, Bull. Korean Chem. Soc., 9, 328 (1988)
Lee WC, Sohn JE, Gal YS, Choi SK, Polym.(Korea), 12(8), 720 (1988)
Gal YS, Choi SK, J. Polym. Sci. C: Polym. Lett., 26, 115 (1988)
Kim YH, Gal YS, Kim UY, Choi SK, Macromolecules, 21, 1991 (1988)
Ryoo MS, Lee WC, Choi SK, Macromolecules, 23, 3029 (1990)
Gal YS, Cho HN, Kwon SK, Choi SK, Polym.(Korea), 12(1), 30 (1988)
Lee WC, Huh MW, Gal YS, Choi SK, Polym.(Korea), 13(6), 520 (1989)

[Referenced By]

[1] Paushkin YM, Vishnyakova TP, Nisova SA, Lunin AF, Omarov OY, Markov YY, Machus FF, Golubera IA, Polak LS, Patalakh II, Stychenko VA, Sokolinskya TA, J. Polym. Sci. A: Polym. Chem., 1(5), 1203 (1967)

[2] Wnek GE, Chien JCW, Karasz FE, Lillya CP, Polymer, 20, 1441 (1979)

[3] Kang ET, Bhatt AP, Villaroel E, Anderson WA, Ehrlich P, J. Polym. Sci. C: Polym. Lett., 20, 143 (1982)

[4] Camus C, Faruffini V, Furlani A, Marsich N, Ortaggi G, Paolesse R, Russo MV, Appl. Org. Chem., 2, 533 (1988)

[5] Masuda T, Higashimura T, Accounts Chem. Res., 17, 51 (1984)

[6] Simionescu CI, Percec V, Prog. Polym. Sci., 8, 133 (1982)

[7] Wegner G, Angew. Chem.-Int. Edit., 20, 361 (1981)

[8] Masuda T, Hasegawa KI, Higashimura T, Macromolecules, 7, 728 (1974)

[9] Gal YS, Cho HN, Choi SK, J. Polym. Sci. A: Polym. Chem., 24, 2021 (1986)

[10] Gal YS, Cho HN, Choi SK, Polym.(Korea), 10(7), 688 (1986)

[11] Okano Y, Masuda T, Higashimura T, Polym. J., 14, 477 (1982)

[12] Chauser MG, Rodionov YM, Misin VM, Cherkashin MI, Russ. Chem. Rev., 45, 348 (1976)

[13] Furlani A, Russo MV, Carusi P, Licoccia S, Leoni E, Valenti GG, Gazz. Chim. Ital., 113, 671 (1983)

[14] Voronkov MG, Pukhnarevich VB, Sushchinskaya SP, Annenkova VZ, Annenkova VM, Andreeva NJ, J. Polym. Sci. A: Polym. Chem., 18, 53 (1980)

[15] Lee WC, Sohn JE, Gal YS, Choi SK, Bull. Korean Chem. Soc., 9, 328 (1988)

[16] Lee WC, Sohn JE, Gal YS, Choi SK, Polym.(Korea), 12(8), 720 (1988)

[17] Gal YS, Choi SK, J. Polym. Sci. C: Polym. Lett., 26, 115 (1988)

[18] Kim YH, Gal YS, Kim UY, Choi SK, Macromolecules, 21, 1991 (1988)

[19] Ryoo MS, Lee WC, Choi SK, Macromolecules, 23, 3029 (1990)

[20] Gal YS, Cho HN, Kwon SK, Choi SK, Polym.(Korea), 12(1), 30 (1988)

[21] Lee WC, Huh MW, Gal YS, Choi SK, Polym.(Korea), 13(6), 520 (1989)