Polymerization of 3,3-Diethoxy-1-propyne by Transition Metal Catalysts

Gal YS; Jung B; Lee WC; Choi SK

Korea Polymer Journal, Vol.1, No.1, 40-44, April, 1993

The polymerization of 3,3-diethoxy-1-propyne having acetal functional group by various Mo- and W-based catalysts. MoCl5 and MoCl5-organoaluminum catalyst systems give some moderate yield of polymer (30~41%). Mo-based catalyst systems were found to be more effective for the present polymerization of 3,3-diethoxy-1-propyne than W-based catalyst systems. The MoCl5-EtAlCl2 catalyst system yielded the best results. The resulting polymers were found to be insoluble in most organic solvents regardless of the polymerization conditions and the catalyst employed. The infrared spectrum of polymer showed neither the acetylenic hydrogen stretching nor the carbon-carbon triple bond stretching frequencies in contrast with that of the monomer. Thermal properties of the resulting polymer were also studied.

[References]

Simonuscu CI, Persec V, Dumitrescu SJ, J. Polym. Sci. A: Polym. Chem., 16, 2497 (1977)
Gal YS, Choi SK, Polym.(Korea), 13(3), 188 (1989)
Masuda T, Higashimura T, Adv. Polym. Sci., 81, 121 (1989)
Chauser MG, Rodionov YM, Misin VM, Cherkashin MI, Russ. Chem. Rev., 45, 348 (1976)
Chiang AC, Waters PF, Aldridge MH, J. Polym. Sci. A: Polym. Chem., 20, 1987 (1982)
Cotton FA, Hall WT, Cann KJ, Karol FJ, Macromolecules, 14, 233 (1981)
Dumitrescu S, Percec V, Simionescu IJ, J. Polym. Sci. A: Polym. Chem., 15, 2893 (1977)
Carlini C, Chien JCW, J. Polym. Sci. A: Polym. Chem., 22, 2749 (1984)
Masuda T, Hasegawa KI, Higashimura T, Macromolecules, 7, 728 (1974)
Masuda T, Kuwane Y, Higashimura T, J. Polym. Sci. A: Polym. Chem., 20, 1043 (1982)
Masuda T, Higashimura T, Accounts Chem. Res., 17, 51 (1984)
Kunzler J, Percec V, J. Polym. Sci. A: Polym. Chem., 28, 1221 (1990)
Masuda T, Mishima K, Fujimori JI, Nishida M, Muramatus H, higashimura T, Macromolecules, 25, 1401 (1992)
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)
Gal YS, Choi SK, Kim CY, J. Polym. Sci. A: Polym. Chem., 27, 31 (1989)
Gal YS, Choi SK, J. Polym. Sci. C: Polym. Lett., 26, 115 (1988)
Jang MS, Kwon SK, Choi SK, Macromolecules, 23, 4135 (1990)
Gal YS, Jung B, Lee WC, Choi SK, Polym.(Korea), 16(5), 597 (1992)
Masuda T, Kawai M, Higashimura T, Polymer, 23, 744 (1992)
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)
Moriya M, Mano S, Yamashita T, Chem. High Polym., 28, 143 (1971)
Brandsma L, Preparative Acetylenic Chemistry 2nd. Ed., Elsevier, Amsterdam, pp. 176-177 (1988)
Gal YS, Cho HN, Kwon SK, Choi SK, Polym.(Korea), 12(1), 30 (1988)
Gal YS, Jung B, Cho HN, Lee WC, Choi SK, Bull. Korean Chem. Soc., 13, 4 (1992)
Gal YS, unpublished results
Gal YS, Jung B, Lee WC, Choi SK, J. Polym. Sci. A: Polym. Chem., 30, 2657 (1992)

[1] Simonuscu CI, Persec V, Dumitrescu SJ, J. Polym. Sci. A: Polym. Chem., 16, 2497 (1977)

[2] Gal YS, Choi SK, Polym.(Korea), 13(3), 188 (1989)

[3] Masuda T, Higashimura T, Adv. Polym. Sci., 81, 121 (1989)

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

[5] Chiang AC, Waters PF, Aldridge MH, J. Polym. Sci. A: Polym. Chem., 20, 1987 (1982)

[6] Cotton FA, Hall WT, Cann KJ, Karol FJ, Macromolecules, 14, 233 (1981)

[7] Dumitrescu S, Percec V, Simionescu IJ, J. Polym. Sci. A: Polym. Chem., 15, 2893 (1977)

[8] Carlini C, Chien JCW, J. Polym. Sci. A: Polym. Chem., 22, 2749 (1984)

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

[10] Masuda T, Kuwane Y, Higashimura T, J. Polym. Sci. A: Polym. Chem., 20, 1043 (1982)

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

[12] Kunzler J, Percec V, J. Polym. Sci. A: Polym. Chem., 28, 1221 (1990)

[13] Masuda T, Mishima K, Fujimori JI, Nishida M, Muramatus H, higashimura T, Macromolecules, 25, 1401 (1992)

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

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

[16] Gal YS, Choi SK, Kim CY, J. Polym. Sci. A: Polym. Chem., 27, 31 (1989)

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

[18] Jang MS, Kwon SK, Choi SK, Macromolecules, 23, 4135 (1990)

[19] Gal YS, Jung B, Lee WC, Choi SK, Polym.(Korea), 16(5), 597 (1992)

[20] Masuda T, Kawai M, Higashimura T, Polymer, 23, 744 (1992)

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

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

[23] Moriya M, Mano S, Yamashita T, Chem. High Polym., 28, 143 (1971)

[24] Brandsma L, Preparative Acetylenic Chemistry 2nd. Ed., Elsevier, Amsterdam, pp. 176-177 (1988)

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

[26] Gal YS, Jung B, Cho HN, Lee WC, Choi SK, Bull. Korean Chem. Soc., 13, 4 (1992)

[27] Gal YS, unpublished results

[28] Gal YS, Jung B, Lee WC, Choi SK, J. Polym. Sci. A: Polym. Chem., 30, 2657 (1992)