Polymerization of Propargylammonium Bromides by Transition Metal Catalysts

Gal YS; Jung B; Lee WC; Choi SK

Korea Polymer Journal, Vol.2, No.2, 104-108, October, 1994

Novel conjugated ionic polymers from propargylammonium bromides having different ammonium cations were synthesized and characterized. PdCl₂ and PtCl₂ were found to be very effective catalysts whereas most of the W-and Mo-based catalysts except MoCl₅-EtAlCl₂ failed to polymerize these ionic acetylene monomers. In the polymerization by PdCl₂, DMF, DMSO, pyridine, and formic acid were found to be good solvent. The resulting polymers were brown or black powder and mostly insoluble in any organic solvents regardless of the polymerization conditions and the catalysts used. The infrared spectra of conjugated ionic polymers showed neither the acetylenic ≡C-H stretching nor the acetylenic C≡C stretching observed in the infrared spectra of monomers. Instead the conjugated double bond stretching of polymer backbone was newly observed at 1630-1652 cm^-1. Thermal and morphological properties of these polymers were also studied.

[References]

Gibson HW, Handbook of Conducting Polymers, Vol. I, p. 405, T.A. Skotheim, Ed., Dekker, New York (1986)
Cukor P, Krugler JI, Rubner MF, Makromol. Chem., 182, 165 (1981)
Gal Ys, Jung B, Choi SK, J. Appl. Polym. Sci., 42, 1793 (1991)
Tang BZ, Masuda T, higashimura T, J. Polym. Sci. A: Polym. Chem., 27, 1261 (1989)
Nagase Y, Mori S, Matsui K, J. Appl. Polym. Sci., 37, 1259 (1989)
Nagase Y, Sugimoto K, Takamura Y, Matsui K, J. Appl. Polym. Sci., 43, 1227 (1991)
Tang BZ, Masuda T, Higashimura T, Yamaoka H, J. Polym. Sci. A: Polym. Chem., 27, 1197 (1989)
Mujie Y, Jian Z, Aibing L, Zhiquan S, Mingjian Z, Senhao L, J. Polym. Sci. A: Polym. Chem., 27, 3829 (1989)
Masuda T, higashimura T, Adv. Polym. Sci., 81, 121 (1986)
Simionescu CI, Percec V, Prog. Polym. Sci., 8, 133 (1982)
Davidov BE, Krentsel BA, Kchutareva BV, J. Polym. Sci. C: Polym. Lett., 16, 1365 (1967)
Kawasaki M, Masuda T, higashimura T, Polym. J., 15, 767 (1983)
Subramanyam A, Blumstein A, Macromolecules, 24, 767 (1983)
Subramanyam A, Blumstein A, U.S. Patent, 503791 (1991)
Subramanyam A, Blumstein A, Li KP, Macromolecules, 25, 2065 (1992)
Gal Ys, J. Chem. Soc.-Chem. Commun., 327 (1994)
Kang KL, Cho HN, Choi KY, Choi SK, Macromolecules, 26, 4539 (1993)
Gal YS, Jung B, Lee WC, Choi SK, Macromolecules Reports, A31, 271 (1994)
Masuda T, Higashimura T, Accounts Chem. Res., 17, 51 (1984)

[Referenced By]

[1] Gibson HW, Handbook of Conducting Polymers, Vol. I, p. 405, T.A. Skotheim, Ed., Dekker, New York (1986)

[2] Cukor P, Krugler JI, Rubner MF, Makromol. Chem., 182, 165 (1981)

[3] Gal Ys, Jung B, Choi SK, J. Appl. Polym. Sci., 42, 1793 (1991)

[4] Tang BZ, Masuda T, higashimura T, J. Polym. Sci. A: Polym. Chem., 27, 1261 (1989)

[5] Nagase Y, Mori S, Matsui K, J. Appl. Polym. Sci., 37, 1259 (1989)

[6] Nagase Y, Sugimoto K, Takamura Y, Matsui K, J. Appl. Polym. Sci., 43, 1227 (1991)

[7] Tang BZ, Masuda T, Higashimura T, Yamaoka H, J. Polym. Sci. A: Polym. Chem., 27, 1197 (1989)

[8] Mujie Y, Jian Z, Aibing L, Zhiquan S, Mingjian Z, Senhao L, J. Polym. Sci. A: Polym. Chem., 27, 3829 (1989)

[9] Masuda T, higashimura T, Adv. Polym. Sci., 81, 121 (1986)

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

[11] Davidov BE, Krentsel BA, Kchutareva BV, J. Polym. Sci. C: Polym. Lett., 16, 1365 (1967)

[12] Kawasaki M, Masuda T, higashimura T, Polym. J., 15, 767 (1983)

[13] Subramanyam A, Blumstein A, Macromolecules, 24, 767 (1983)

[14] Subramanyam A, Blumstein A, U.S. Patent, 503791 (1991)

[15] Subramanyam A, Blumstein A, Li KP, Macromolecules, 25, 2065 (1992)

[16] Gal Ys, J. Chem. Soc.-Chem. Commun., 327 (1994)

[17] Kang KL, Cho HN, Choi KY, Choi SK, Macromolecules, 26, 4539 (1993)

[18] Gal YS, Jung B, Lee WC, Choi SK, Macromolecules Reports, A31, 271 (1994)

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