전이금속촉매에 의한 프로파길 벤젠술폰에이트의 중합

갈영순; 정발; 이원철; 최삼권

Polymer(Korea), Vol.16, No.2, 191-196, March, 1992

Export Citation

전이금속촉매에 의한 프로파길 벤젠술폰에이트의 중합

Polymerization of Propargyl Benzenesulfonate by Transition Metal Catalysts

갈영순, 정발, 이원철, 최삼권

초록

여러가지 전이금속촉매를 사용하여 프로파길 벤젠술폰에이트(PBS)를 중합시켜 술본에이트 기능기를 갖는 새로운 공액구조 고분자를 합성하였다. Mo-계 촉매가 W-계 촉매보다 본 중합이 더 효과적이였으며 특히 MoCl₅-유기알루미늄 촉매가 매우 효과적인 것으로 밝혀 졌다. W 및 Mo 에톡사이드-EtAICI₂ 역시 PBS를 효과적으로 중합하였다. PdCl₂와 PtCl₂를 사용하여 PBS를 중합시킨 결과 높은 수율의 고분자를 합성할 수 있었다. 생성된 폴리(PBS)들은 사용한 촉매와 중합조건에 관계없이 유기용매에 용해하지 않았으며 검은색의 분말형이였다. 폴리(PBS)들의 열특성에 관해서도 연구하였다.

A new conjugated polymer containing sulfonate functional group was synthesized by the polymerization of propargyl benzenesulfonate(PBS) with various transition metal catalysts. Mo-based catalysts were more effective than W-based catalysts. Especially MoCl₅-organoaluminum catalysts were very effective. W and Mo ethoxide-EtAlCl₂ catalysts were also found to be very active for this polymerization. PdC1₂ also polymerized PBS to produce a high yield of polymer. The resulting poly(PBS) were insoulble in organic solvents regardless of catalysts used. This polymer was dark colored powder. Thermal properties of poly(PBS) were also studied.

[References]

Chauser MG, Rodionov YM, Misin VM, Cherkashin MI, Rubber Chem. Rev., 45, 348 (1976)
Akopyan LA, Ambartsumyan GV, Ovakimyan EV, Matsoyan SG, Vysokomol. Soyed., A19, 271 (1977)
Gibson HW, "Handbook of Conducting Polymers," ed. by T.A. Skotheim, Chapter II, Marcel Dekker Inc., Y.Y. (1986)
Akopyan LA, Grigoryan SG, Zhamkochyan GA, Matsoyan SG, Vysokomol. Soedin. Ser. A, 17(11), 2517 (1975)
Akopyan LA, Grigoryan SG, Zhamkochyan GA, Matsoyan SG, Chem. Abstr., 84, 45039 (1976)
Okamura S, Hayashi K, Japan Patent, 7889 (1963)
Okamura S, Hayashi K, Chem. Abstr., 59, 7672a (1963)
Okamura S, Kogyo Kagaku Zasshi, 65, 728 (1962)
Okamura S, Chem. Abstr., 57, 15320b (1962)
Furlani A, Russo MV, Carusi P, Licoccia S, Leoni E, Valenti G, Gazz. Chim. Ital., 113, 671 (1983)
Manassen J, Wallach J, J. Am. Chem. Soc., 87, 2671 (1965)
Masuda T, Kuwane Y, Yamamoto Y, Higashimura T, Polym. Bull., 2, 823 (1980)
Voronkov MG, Pukhnarevich VB, Sushchinskaya SP, Annenkova VZ, Annenkova VM, Andreeva NJ, J. Polym. Sci. A: Polym. Chem., 18, 53 (1980)
Kiyashikima S, Pomogailso AD, Kuzayev AD, Lagodzinskaya AI, Dyachkovskii GV, J. Polym. Sci. Polym. Symp., 68, 13 (1980)
Pomogailo AD, Kiyashikina S, Kuzaev AI, Yechmaev SB, Ivleva IN, Dyachkovskii FS, Vysokomol. Soedin, 17, 707 (1985)
Pomogailo AD, Kiyashikina S, Kuzaev AI, Yechmaev SB, Ivleva IN, Dyachkovskii FS, Chem. Abstr., 102, 221246 (1985)
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)
Kunzler J, Percec V, J. Polym. Sci. A: Polym. Chem., 28, 1043 (1990)
Yoshimura K, Kitade T, Kitamura K, Hozumi K, J. Appl. Polym. Sci., 38, 1011 (1989)
Katz TJ, Ho TH, Shih NY, Ying YC, Stuat VIW, J. Am. Chem. Soc., 106, 2659 (1984)
Gal YS, Choi SK, Polym.(Korea), 11(6), 563 (1987)
Lee WC, Huh MW, Gal YS, Choi SK, Polym.(Korea), 13(6), 520 (1989)
Lee WC, Gal YS, Ryoo MS, Han SH, Choi SK, Polym.(Korea), 15(3), 283 (1991)
Tsuda K, J. Adhes. Soc. Jpn., 24, 200 (1988)
Gal YS, Cho HN, Choi SK, J. Polym. Sci. A: Polym. Chem., 24, 2021 (1986)
Gal YS, Cho HN, Choi SK, Polym.(Korea), 9(5), 361 (1985)
Gal YS, Choi SK, J. Polym. Sci. C: Polym. Lett., 26, 115 (1988)
Masuda T, Matsumoto T, Yoshimura T, Higashimura T, Macromolecules, 23, 4902 (1990)
Masuda T, Kawai M, Higashimura T, Polymer, 23, 744 (1982)
Ryoo MS, Lee WC, Choi SK, Macromolecules, 23, 3029 (1990)
Han SH, Kim UY, Kang YS, Choi SK, Macromolecules, 24, 973 (1991)
Masuda T, Thieu KQ, Sasaki N, Higashimura T, Macromolecules, 9, 661 (1976)
Natta G, Dall'Asta G, Mazzanti G, Montroni G, Makromol. Chem., 69, 163 (1963)
Tanielian C, Keffer R, Harfouch A, J. Mol. Catal., 10, 269 (1981)
Mocella MT, Rovner R, Muetterties EL, J. Am. Chem. Soc., 98, 4689 (1976)
Streck R, J. Mol. Catal., 15, 3 (1982)
Lambert JB, Shurvell HF, Verbit L, Cooks RG, Stout GH, "Organic Structural Analysis," p. 225, Macmillan Publishing Co., Inc., N.Y. (1976)
Gal YS, unpublished data

[Referenced By]

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

[2] Akopyan LA, Ambartsumyan GV, Ovakimyan EV, Matsoyan SG, Vysokomol. Soyed., A19, 271 (1977)

[3] Gibson HW, "Handbook of Conducting Polymers," ed. by T.A. Skotheim, Chapter II, Marcel Dekker Inc., Y.Y. (1986)

[4] Akopyan LA, Grigoryan SG, Zhamkochyan GA, Matsoyan SG, Vysokomol. Soedin. Ser. A, 17(11), 2517 (1975)

[5] Akopyan LA, Grigoryan SG, Zhamkochyan GA, Matsoyan SG, Chem. Abstr., 84, 45039 (1976)

[6] Okamura S, Hayashi K, Japan Patent, 7889 (1963)

[7] Okamura S, Hayashi K, Chem. Abstr., 59, 7672a (1963)

[8] Okamura S, Kogyo Kagaku Zasshi, 65, 728 (1962)

[9] Okamura S, Chem. Abstr., 57, 15320b (1962)

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

[11] Manassen J, Wallach J, J. Am. Chem. Soc., 87, 2671 (1965)

[12] Masuda T, Kuwane Y, Yamamoto Y, Higashimura T, Polym. Bull., 2, 823 (1980)

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

[14] Kiyashikima S, Pomogailso AD, Kuzayev AD, Lagodzinskaya AI, Dyachkovskii GV, J. Polym. Sci. Polym. Symp., 68, 13 (1980)

[15] Pomogailo AD, Kiyashikina S, Kuzaev AI, Yechmaev SB, Ivleva IN, Dyachkovskii FS, Vysokomol. Soedin, 17, 707 (1985)

[16] Pomogailo AD, Kiyashikina S, Kuzaev AI, Yechmaev SB, Ivleva IN, Dyachkovskii FS, Chem. Abstr., 102, 221246 (1985)

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

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

[19] Kunzler J, Percec V, J. Polym. Sci. A: Polym. Chem., 28, 1043 (1990)

[20] Yoshimura K, Kitade T, Kitamura K, Hozumi K, J. Appl. Polym. Sci., 38, 1011 (1989)

[21] Katz TJ, Ho TH, Shih NY, Ying YC, Stuat VIW, J. Am. Chem. Soc., 106, 2659 (1984)

[22] Gal YS, Choi SK, Polym.(Korea), 11(6), 563 (1987)

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

[24] Lee WC, Gal YS, Ryoo MS, Han SH, Choi SK, Polym.(Korea), 15(3), 283 (1991)

[25] Tsuda K, J. Adhes. Soc. Jpn., 24, 200 (1988)

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

[27] Gal YS, Cho HN, Choi SK, Polym.(Korea), 9(5), 361 (1985)

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

[29] Masuda T, Matsumoto T, Yoshimura T, Higashimura T, Macromolecules, 23, 4902 (1990)

[30] Masuda T, Kawai M, Higashimura T, Polymer, 23, 744 (1982)

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

[32] Han SH, Kim UY, Kang YS, Choi SK, Macromolecules, 24, 973 (1991)

[33] Masuda T, Thieu KQ, Sasaki N, Higashimura T, Macromolecules, 9, 661 (1976)

[34] Natta G, Dall'Asta G, Mazzanti G, Montroni G, Makromol. Chem., 69, 163 (1963)

[35] Tanielian C, Keffer R, Harfouch A, J. Mol. Catal., 10, 269 (1981)

[36] Mocella MT, Rovner R, Muetterties EL, J. Am. Chem. Soc., 98, 4689 (1976)

[37] Streck R, J. Mol. Catal., 15, 3 (1982)

[38] Lambert JB, Shurvell HF, Verbit L, Cooks RG, Stout GH, "Organic Structural Analysis," p. 225, Macmillan Publishing Co., Inc., N.Y. (1976)

[39] Gal YS, unpublished data