Abstract
“Living” polymerization is of great utility both in understanding the mechanism of chain propagation reactions and in synthesizing well-defined block copolymers. In this review we deal with the development of soluble Ziegler-Natta catalysts for the living coordination polymerization of ethylene and α-olefins and discuss the possibility of synthesis of new block copolymers.
The first example of “living” polyolefin with a uniform chain length was found in the low-temperature polymerization of propylene with the soluble catalyst composed of V (acac)3 and Al(C2H5)2 Cl. The mechanism of the living coordination polymerization is discussed on the basis of the kinetic and stereochemical data. Subsequently, some applications of living polypropylene are introduced to prepare tailormade polymers such as terminally functionalized polymers and block copolymers which exhibit new characteristic properties. Finally, new types of soluble Ziegler-Natta catalysts are briefly surveyed in connection with the synthesis of living polyolefins.
In conclusion, we indicate the future trends of research and development in the field of soluble Ziegler-Natta catalysts for the synthesis of living polyolefins and block copolymers.
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9 References
Boor, J. Jr.: Ziegler-Natta Catalysts and Polymerizations, New York, Academic Press, 1979
Chien, J. C. W. (ed.): Coordination Polymerization, New York, Academic Press, 1975
Quirk, R. P. (ed.): Transition Metal Catalyzed Polymerizations, Part A and B, New York, Harwood Academic Publ., 1983
Price, C. C., Vandenberg, E. J. (eds.): Coordination Polymerization, New York-London, Plenum Press, 1983
Keii, T.: Kinetics of Ziegler-Natta Polymerization, Tokyo-London, Kodansha-Chapman and Hall, 1972
Keii, T.: in ref. 2, p. 263
Cooper, W.: in Comprehensive Chemical Kinetics, Bamford, C. H., Tipper. C. F. H. (eds.), Vol. 15, p. 133, Amsterdam, Elsevier, 1976
Tait, P. J. T.: in Developments in Polymerization, Haward, R. N. (ed.), Vol. 2, p. 81, London, Applied Science Publ., 1979
Cossee, P.: in The Stereochemistry of Macromolecules, Ketley, A. D. (ed.), Vol. 1, p. 145, New York, Marcel Dekker, Inc., 1968
Zambelli, A., Tosi, C.: Adv. Polym. Sci. 15, 31 (1974)
Zambelli, A., Sacchi, M. C., Locatelli, P.: in ref. 3, p. 83
Pino, P., Mülhaupt, R.: Angew. Chem. Int. Ed. Engl. 19, 857 (1980)
Henrici-Olivé, G., Olivé, S.: Angew. Chem. Int. Ed. Engl. 6, 790 (1967)
Henrici-Olivé, G., Olivé, S.: Adv. Polym. Sci., 15, 1 (1974)
Henrici-Olivé, G., Olivé, S.: Coordination and Catalysis, Weinheim-New York, Verlag Chemie 1976
Dyachkovskii, F. S.: in ref. 2, p. 199
Fink, G., Rotter, R., Schnell, D., Zoller: J. Appl. Polym. Sci. 20, 2779 (1976)
Fink, G.: in ref. 3, p. 495
Reichert, K. H.: Angew. Makromol. Chem. 94, 1 (1981)
Reichert, K. H.: in ref. 3, p. 465
Sinn, H., Kaminsky, W.: Adv. Organomet. Chem. 18, 99 (1980)
Ballard, D. G. H., Adv. Catal., 23, 263 (1973)
Yamamoto, A., Yamamoto, T.: Macromol. Rev. 13, 161 (1978)
Karol, F. J.: in Encyclopedia of Polymer Science and Technology, Mark, H. F., Gikales, N. M. (eds.), Suppl. 1, p. 120, New York, Interscience, 1976
Sivaram, S.: Ind. Eng. Chem, Prod. Res. Dev. 16, 121 (1977)
Galli, P., Luciani, L., Cecchin, G.: Angew. Makromol. Chem. 94, 63 (1981)
Kashiwa, N.: in ref. 3, p. 379
Keii, T., Suzuki, E., Tamura, M., Murata, M., Doi, Y.: Makromol. Chem. 183, 2285 (1982)
Tait, P. J. T.: in Preparation and Properties of Stereoregular Polymers, Lenz, R. W., Ciardelli, F. (eds.), p. 85, Dordrecht (Holland), D. Reidel Publ., 1980
Tait, P. J. T.: in ref. 3, p. 115
Zakharov, V. A., Yermakov, Yu. I.: Catal. Rev. Sci. Eng. 19, 67 (1979)
Yermakov, Yu. I., Zakharov, V. A.: in ref. 2, p. 91
Zakharov, V. A., Bukatov, G. D., Yermakov, Yu. I.: in ref. 4, p. 267
Zucchini, U., Cecchin, G.: Adv. Polym. Sci. 51, 101 (1983)
Taylor, T. W., Choi, K. Y., Yuan, H., Ray, W. H.: in ref. 3, p. 191
Vanderberg, E. J., Repka, B. C.: in Polymerization Processes, High Polymer Ser., 29, Schildknecht, C. E., Skeist, I. (eds.): p. 337, New York, Interscience, 1977
Karol, F. J.: Chemtech 222, april 1983
Short, J. N.: in ref. 3, p. 651
Brockmeier, N. F.: in ref. 3, p. 671
Flory, J. P.: J. Am. Chem. Soc. 62, 1561 (1940)
Gold, L.: J. Chem. Phys. 28, 91 (1958)
Szwarc, M.: Carbanions, Living Polymers and Electron Transfer Processes, New York, Interscience, 1968
Morton, M.: Anionic Polymerization, Principles and Practice, New York, Academic Press, 1983
Bier, G., Lehmann, G.: in Copolymerization, Ham, G. E. (ed.), Chapter 1VB, New York, Interscience, 1964
Heggs, T. G.: in Block Copolymers, Allport, O. C., Janes, W. H. (eds.), Chapter 4, New York, Interscience, 1973
Boor, J. Jr., in ref. 1, Chapter 21
Doi, Y., Ueki, S., Keii, T.: Macromolecules 12, 814 (1979)
Doi, Y., Ueki, S., Keii, T.: Makromol. Chem. 180, 1359 (1979)
Natta, G., Pasquon, I., Svab, J., Zambelli, A.: Chim. Ind. (Milan) 44, 621 (1962)
Grieveson, B. M.: Makromol. Chem. 84, 93 (1965)
Böhm, L. L.: Polymer 19, 545 (1978)
Largo-Cabrerizo, J., Guzman, J.: Macromolecules 12, 526 (1979)
Schulz, G. V.: Z. Phys. Chem., Abt. B 30, 379 (1935); ibid. 43, 25 (1939)
Agasaryan, A. B., Belov, G. P., Davtyan, S. P., Eritsyan, M. L.: Europ. Polym. J. 11, 549 (1975)
Doi, Y., Takada, M., Keii, T.: Bull. Chem. Soc. Jpn, 52, 1802 (1979)
Berger, M. N., Boocook, G., Haward, R. N.: Adv. Catal. 19, 211 (1968)
Keii, T., Doi, Y., Suzuki, E., Tamura, M., Murata, M., Soga, K.: Makromol. Chem., 185, 1537 (1984)
Coleman, B. D., Fox, T. G.: J. Am. Chem. Soc. 85, 1241 (1963)
Figini, R. V.: Makromol. Chem. 44, 497 (1961)
Orofino, T. A., Wenger, F.: J. Chem. Phys. 35, 532 (1961)
Henrici-Olivé, G., Olivé, S.: in ref. 2, P. 291
Höcker, H., Saeki, K.: Makromol. Chem. 148, 107 (1971)
Belov, G. P., Kuznetsov, V. I., Solovyeva, T. I., Chirkov, N. M., Ivanchev, S. S.: Makromol. Chem. 140, 213 (1970)
Reichert, K. H., Meyer, K. R.: Makromol. Chem. 169, 163 (1973)
Henrici-Olivé, G., Olivé, S.: Adv. Polym. Sci. 6, 421 (1969)
Hay, J. N., Obaid, R. M. S.: Eurp. Polym. J. 14, 965 (1978)
Waters, J. A., Mortimer, G. A.: J. Polym. Sci., Part A-1 10, 895 (1972)
Cihlár, J., Mejzlik, J., Hamrik, O., Hudec, P., Majer, J.: Makromol. Chem. 181, 2549 (1980)
Reichert, K. H.: Angew. Makromol. Chem. 13, 177 (1970)
Fink, G., Zoller, W.: Makromol. Chem. 182, 3265 (1981)
Fink, G., Schnell, D.: Angew. Makromol. Chem. 105, 15 (1982)
Fink, G., Rottler, R.: Angew. Makromol. Chem. 94, 25 (1981)
Natta, G., Pasquon, I., Zambelli, A.: J. Am. Chem. Soc. 84, 1488 (1962)
Natta, G., Zambelli, A., Lanzi, G., Pasquon, I., Magnaschi, E. R., Segre, A. L., Centola, P.: Makromol. Chem. 81, 161 (1965)
Zambelli, A., Natta, G., Pasquon, I., Signorini, R.: J. Polym. Soc., Part C 16, 2485 (1967)
Zambelli, A., Pasquon, I., Signorini, R., Natta, G.: Makromol. Chem. 112, 160 (1968)
Boor, J. Jr., Youngman, E. A.: J. Polym. Sci., Part A-1 4, 1861 (1966)
Mitani, K., Suzuki, T., Matsuo, A., Takegami, Y.: J. Polym. Sci., Polym. Chem. Ed. 12, 771 (1974)
Doi, Y., Kinioshita, J., Morinaga, A., Keii, T.: J. Polym. Sci., Polym. Chem. Ed. 13, 2491 (1975)
Doi, Y., Takada, M., Keii, T.: Makromol. Chem. 180, 57 (1979)
Evens, G. G., Pijpers, E. M. J.: in ref. 3, p. 245
Ueki, S.: Doctor of Engineering, Thesis, Tokyo Institute of Technology, 1982
Doi, Y., Koyama, T., Soga, K., Asakura, T.: Makromol. Chem. 185, 1827 (1984)
Doi, Y., Ueki, S., Keii, T.: in ref. 4, p. 249
Doi, Y., Ueki, S., Tamura, S., Nagahara, S., Keii, T.: Polymer 23, 258 (1982)
Machin, D. J., Murray, K. S.: J. Chem. Soc., A 1498 (1968)
Suzuki, T., Takegami, Y.: Bull. Chem. Soc. Jpn 43, 148 (1970)
Dewar, M. J. S., Patterson, D. B., Sympson, W. I.: J. Am. Chem. Soc. 93, 1030 (1971)
Bovey, F. A., Tiers, G. V. D.: J. Polym. Sci. 44, 173 (1960)
Bovey, F. A., Sacchi, M. C., Zambelli, A.: Macromolecules 7, 752 (1974)
Zambelli, A., Bajo, G., Rigamonti, E.: Makromol. Chem. 179, 1249 (1979)
Zambelli, A., Allegra, G.: Macromolecules 13, 42 (1980)
Asakura, T., Ando, I., Nishioka, A., Doi, Y., Keii, T.: Makromol. Chem. 178, 791 (1977)
Asakura, T., Doi, Y.: Macromolecules 13, 454 (1980)
Doi, Y.: Macromolecules 12, 1012 (1979)
Doi, Y.: Macromolecules 12, 248 (1979)
Zambelli, A., Tosi, C., Sacchi, C.: Macromolecules 5, 649 (1972)
Doi, Y., Nozawa, F., Soga, K.: Makromol. Chem., in press.
Vandenberg, E. J.: U.S. Patent 3,051,690 (1962)
Natta, G., Mazzanti, G., Longi, P., Bernadini, F.: Chim. Ind. (Milan) 41, 519 (1959)
Shindler, A.: Makromol. Chem. 73, 94 (1964)
Doi, Y., Ueki, S., Keii, T.: Polymer 21, 1352 (1980)
Ueki, S., Doi, Y., Keii, T.: Makromol. Chem., Rapid Commun. 2, 403 (1981)
Doi, Y., Watanabe, Y., Ueki, S., Soga, K.: Makromol. Chem., Rapid Commun. 4, 533 (1983)
Mejzlik, J., Lesna, M.: Makromol. Chem. 178, 261 (1977)
Warzelhan, V., Burger, T. F., Stein, D. J.: Makromol. Chem. 183, 489 (1982)
Fachinetti, G., Floriani, C., Soeckii-Evens, H.: J. Chem. Soc., Dalton Trans. 2297 (1977)
Grigoryan, E. A., Gyulumyan, Kh. R.: Kinet. Katal. 22, 164 (1981)
Tritto, I., Sacchi, M. C., Locatelli, P.: Makromol. Chem., Rapid Commun. 4, 623 (1983)
Doi, Y., Murata, M., Soga, K.: Makromol. Chem., Rapid Commun., 5, 811 (1984)
Doi, Y., Ueki, S., Keii, T.: Makromol. Chem., Rapid Commun. 3, 225 (1982)
Doi, Y., Koyama, T., Soga, K.: Makromol. Chem., 186, 11 (1985)
Lee, M., Morigami, T., Minoura, Y.: J. Chem. Soc. Faraday Trans. I, 74, 1738 (1978)
Burgess, F. J., Cunliffe, A. V., Richards, D. H., Thompson, D.: Polymer 19, 334 (1978)
Andersen, A., Cordes, H.-G., Herwig, J., Kaminsky, W., Merck, A., Mottweiler, R., Pein, J., Sinn, H., Vollmer, H.-J.: Angew. Chem. Int. Ed. Engl. 15, 630 (1976)
Kaminsky, W.: in ref. 3, p. 225
Herwig, J., Kaminsky, W.: Polym. Bull. 9, 464 (1983)
Kaminsky, W., Miri, M., Sinn, H., Woldt, R.: Makromol. Chem., Rapid Commun. 4, 417 (1983)
Kaminsky, W., Lüker, H.: Makromol. Chem., Rapid Commun. 5, 225 (1984)
Shen, Z., Ouyang, J., Wang, F., Hu, Z., Yu, F., Qian, B.: J. Polym. Chem., Polym. Chem. Ed., 18, 3345 (1980)
Shen, Z., Song, X., Xiao, S., Yang, J., Kan, X.: J. Appl. Polym. Sci. 28, 1585 (1983)
Ouyang, J., Wang, F.-S., Huang, B.-T.: in ref. 3, p. 265
Ballard, D. G. H., Courtis, A., Holton, J., McMeeking, J., Pearce, R.: J. Chem. Soc., Chem. Commun. 994 (1978)
Watson, P. L.: J. Am. Chem. Soc. 104, 337 (1982)
Watson, P. L., Roe, D. C.: J. Am. Chem. Soc. 104, 6471 (1982)
Watson, P. L., Herskovitz, T.: A.C.S. Symposium Series 210, 459 (1983)
Ziegler, K.: Angew. Chem. 64, 323 (1952)
Soga, K., Shiono, T., Doi, Y.: J. Chem. Soc., Chem. Commun. 840 (1984)
Ewen, J. A.: J. Am. Chem. Soc. 106, 6355 (1984)
Wolfsgruber, C., Zannoni, G., Rigamonti, E., Zambelli, A.: Makromol. Chem. 176, 2765 (1975)
Doi, Y., Suzuki, T., Keii, T.: Makromol. Chem., Rapid Commun. 2, 293 (1981)
Doi, Y., Asakura, T.: Makromol. Chem. 176, 507 (1975)
Sheldon, R. A., Fueno, T., Tsunetuga, T., Furukawa, J.: J. Polym. Sci., Part B, 3, 23 (1965)
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Doi, Y., Keii, T. (1986). Synthesis of “living” polyolefins with soluble Ziegler-Natta catalysts and application to block copolymerization. In: Chromatography/Foams/Copolymers. Advances in Polymer Science, vol 73/74. Springer, Berlin, Heidelberg. https://doi.org/10.1007/3-540-15786-7_10
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