Condensative chain polymerization. Chemoselectivity of aryloxysilane toward substituted aromatic acid chlorides in a model reaction

Polymer Journal

Volumn 28, Issue 7, 1996, Pages 633-636

  Yokozawa, Tsutomu ^a   Horio, Shin Ichi ^a  

^a KANAGAWA UNIVERSITY   (Japan)

Author keywords

Aromatic Acid Chloride; Aryloxysilane; Chain Polymerization; Chemosolectivity; Fluoride Ion; Polycondensation; Polyester; Siloxybenzoyl Chloride

Indexed keywords

AROMATIC POLYMERS; CATALYSTS; CHLORINE; CONFORMATIONS; ESTERS; FLUORINE; GAS CHROMATOGRAPHY; IONS; MONOMERS;

AMINO GROUP; AROMATIC ACID CHLORIDE; ARYLOXYSILANE; CARBOXYL GROUP; CHEMOSELECTIVITY; FLUORIDE ION; HYDROXY GROUP; SILOXYBENZOYL CHLORIDE;

POLYCONDENSATION;

EID: 0029720048     PISSN: 00323896     EISSN: None     Source Type: Journal    
DOI: 10.1295/polymj.28.633     Document Type: Article

References (19)

1. For examples of anionic living polymerization. see: (a) M. Morton, "Anionic Polymerization. Principles and Practice," Academic Press, New York, N.Y., 1983. (b) M. van Beylen, S. Bywater, G. Smets, M. Szware, and D. J. Worsfold, Adv. Polym. Sci., 86, 87 (1958). (c) O. W. Webster and B. C. Anderson, "New Methods for Polymer Synthesis," W. J. Mijs, Ed., Plenum, New York. N.Y., 1992, p 1. (d) M. T. Reetz, Angew. Chem. Int. Ed. Engl. 11, 994 (1988). (e) S. Inoue and T. Aida, "New Methods for Polymer Synthesis." W. J. Mijs. Ed., Plenum, New York, N.Y., 1992, p 33.
2. For examples of anionic living polymerization. see: (a) M. Morton, "Anionic Polymerization. Principles and Practice," Academic Press, New York, N.Y., 1983. (b) M. van Beylen, S. Bywater, G. Smets, M. Szware, and D. J. Worsfold, Adv. Polym. Sci., 86, 87 (1958). (c) O. W. Webster and B. C. Anderson, "New Methods for Polymer Synthesis," W. J. Mijs, Ed., Plenum, New York. N.Y., 1992, p 1. (d) M. T. Reetz, Angew. Chem. Int. Ed. Engl. 11, 994 (1988). (e) S. Inoue and T. Aida, "New Methods for Polymer Synthesis." W. J. Mijs. Ed., Plenum, New York, N.Y., 1992, p 33.
3. For examples of anionic living polymerization. see: (a) M. Morton, "Anionic Polymerization. Principles and Practice," Academic Press, New York, N.Y., 1983. (b) M. van Beylen, S. Bywater, G. Smets, M. Szware, and D. J. Worsfold, Adv. Polym. Sci., 86, 87 (1958). (c) O. W. Webster and B. C. Anderson, "New Methods for Polymer Synthesis," W. J. Mijs, Ed., Plenum, New York. N.Y., 1992, p 1. (d) M. T. Reetz, Angew. Chem. Int. Ed. Engl. 11, 994 (1988). (e) S. Inoue and T. Aida, "New Methods for Polymer Synthesis." W. J. Mijs. Ed., Plenum, New York, N.Y., 1992, p 33.
4. For examples of anionic living polymerization. see: (a) M. Morton, "Anionic Polymerization. Principles and Practice," Academic Press, New York, N.Y., 1983. (b) M. van Beylen, S. Bywater, G. Smets, M. Szware, and D. J. Worsfold, Adv. Polym. Sci., 86, 87 (1958). (c) O. W. Webster and B. C. Anderson, "New Methods for Polymer Synthesis," W. J. Mijs, Ed., Plenum, New York. N.Y., 1992, p 1. (d) M. T. Reetz, Angew. Chem. Int. Ed. Engl. 11, 994 (1988). (e) S. Inoue and T. Aida, "New Methods for Polymer Synthesis." W. J. Mijs. Ed., Plenum, New York, N.Y., 1992, p 33.
5. For examples of anionic living polymerization. see: (a) M. Morton, "Anionic Polymerization. Principles and Practice," Academic Press, New York, N.Y., 1983. (b) M. van Beylen, S. Bywater, G. Smets, M. Szware, and D. J. Worsfold, Adv. Polym. Sci., 86, 87 (1958). (c) O. W. Webster and B. C. Anderson, "New Methods for Polymer Synthesis," W. J. Mijs, Ed., Plenum, New York. N.Y., 1992, p 1. (d) M. T. Reetz, Angew. Chem. Int. Ed. Engl. 11, 994 (1988). (e) S. Inoue and T. Aida, "New Methods for Polymer Synthesis." W. J. Mijs. Ed., Plenum, New York, N.Y., 1992, p 33.
6. For examples of cationic living polymerization, see: (a) T. Higashimura, M. Miyamoto, and M. Sawamoto, Macromolecules, 18, 611 (1985). (b) R. Faust and J. P. Kennedy, Polym. Bull., 15, 317 (1986). (c) E. J. Goethals and R. R. DeClercq, "New Methods for Polymer Synthesis," W. J. Mijs, Ed., Plenum, New York, N.Y., 1992, p 67.
7. For examples of cationic living polymerization, see: (a) T. Higashimura, M. Miyamoto, and M. Sawamoto, Macromolecules, 18, 611 (1985). (b) R. Faust and J. P. Kennedy, Polym. Bull., 15, 317 (1986). (c) E. J. Goethals and R. R. DeClercq, "New Methods for Polymer Synthesis," W. J. Mijs, Ed., Plenum, New York, N.Y., 1992, p 67.
8. For examples of cationic living polymerization, see: (a) T. Higashimura, M. Miyamoto, and M. Sawamoto, Macromolecules, 18, 611 (1985). (b) R. Faust and J. P. Kennedy, Polym. Bull., 15, 317 (1986). (c) E. J. Goethals and R. R. DeClercq, "New Methods for Polymer Synthesis," W. J. Mijs, Ed., Plenum, New York, N.Y., 1992, p 67.
9. For examples of radical living polymerization, see: (a) T. Otsu and M. Yoshida, Makromol. Chem., Rapid Commun., 3, 127, 133 (1982). (b) D. H. Solomon, G. Waverly, E. Rizzardo, W. Hill, and P. Cacioli, U.S. Patent 4,581,429, 1986. (c) M. K. Georges, R. P. N. Veregin, P. M. Kazmaier, and G. K. Hamer, Macromolecules, 26, 5316 (1993). (d) B. B. Wayland, G. Poszmik, S. L. Mukerjee, and M. Fryd, J. Am. Chem. Soc., 116, 7943 (1994). (c) D. Greszta, D. Mardare, and K. Matyjaszewski, Macromolecules, 27, 638 (1994). (f) M. Kato, M. Kamigaito, M. Sawamoto, and T. Higashimura, Macromolecules, 28, 1721 (1995). (g) K. Matyjaszewski, S. Gaynor, and J.-S. Wang, Macromolecules, 28, 2093 (1995). (h) J.-S. Wang and K. Matyjaszewski, J. Am. Chem. Soc., 117, 5614 (1995).
10. For examples of radical living polymerization, see: (a) T. Otsu and M. Yoshida, Makromol. Chem., Rapid Commun., 3, 127, 133 (1982). (b) D. H. Solomon, G. Waverly, E. Rizzardo, W. Hill, and P. Cacioli, U.S. Patent 4,581,429, 1986. (c) M. K. Georges, R. P. N. Veregin, P. M. Kazmaier, and G. K. Hamer, Macromolecules, 26, 5316 (1993). (d) B. B. Wayland, G. Poszmik, S. L. Mukerjee, and M. Fryd, J. Am. Chem. Soc., 116, 7943 (1994). (c) D. Greszta, D. Mardare, and K. Matyjaszewski, Macromolecules, 27, 638 (1994). (f) M. Kato, M. Kamigaito, M. Sawamoto, and T. Higashimura, Macromolecules, 28, 1721 (1995). (g) K. Matyjaszewski, S. Gaynor, and J.-S. Wang, Macromolecules, 28, 2093 (1995). (h) J.-S. Wang and K. Matyjaszewski, J. Am. Chem. Soc., 117, 5614 (1995).
11. For examples of radical living polymerization, see: (a) T. Otsu and M. Yoshida, Makromol. Chem., Rapid Commun., 3, 127, 133 (1982). (b) D. H. Solomon, G. Waverly, E. Rizzardo, W. Hill, and P. Cacioli, U.S. Patent 4,581,429, 1986. (c) M. K. Georges, R. P. N. Veregin, P. M. Kazmaier, and G. K. Hamer, Macromolecules, 26, 5316 (1993). (d) B. B. Wayland, G. Poszmik, S. L. Mukerjee, and M. Fryd, J. Am. Chem. Soc., 116, 7943 (1994). (c) D. Greszta, D. Mardare, and K. Matyjaszewski, Macromolecules, 27, 638 (1994). (f) M. Kato, M. Kamigaito, M. Sawamoto, and T. Higashimura, Macromolecules, 28, 1721 (1995). (g) K. Matyjaszewski, S. Gaynor, and J.-S. Wang, Macromolecules, 28, 2093 (1995). (h) J.-S. Wang and K. Matyjaszewski, J. Am. Chem. Soc., 117, 5614 (1995).
12. For examples of radical living polymerization, see: (a) T. Otsu and M. Yoshida, Makromol. Chem., Rapid Commun., 3, 127, 133 (1982). (b) D. H. Solomon, G. Waverly, E. Rizzardo, W. Hill, and P. Cacioli, U.S. Patent 4,581,429, 1986. (c) M. K. Georges, R. P. N. Veregin, P. M. Kazmaier, and G. K. Hamer, Macromolecules, 26, 5316 (1993). (d) B. B. Wayland, G. Poszmik, S. L. Mukerjee, and M. Fryd, J. Am. Chem. Soc., 116, 7943 (1994). (c) D. Greszta, D. Mardare, and K. Matyjaszewski, Macromolecules, 27, 638 (1994). (f) M. Kato, M. Kamigaito, M. Sawamoto, and T. Higashimura, Macromolecules, 28, 1721 (1995). (g) K. Matyjaszewski, S. Gaynor, and J.-S. Wang, Macromolecules, 28, 2093 (1995). (h) J.-S. Wang and K. Matyjaszewski, J. Am. Chem. Soc., 117, 5614 (1995).
13. For examples of radical living polymerization, see: (a) T. Otsu and M. Yoshida, Makromol. Chem., Rapid Commun., 3, 127, 133 (1982). (b) D. H. Solomon, G. Waverly, E. Rizzardo, W. Hill, and P. Cacioli, U.S. Patent 4,581,429, 1986. (c) M. K. Georges, R. P. N. Veregin, P. M. Kazmaier, and G. K. Hamer, Macromolecules, 26, 5316 (1993). (d) B. B. Wayland, G. Poszmik, S. L. Mukerjee, and M. Fryd, J. Am. Chem. Soc., 116, 7943 (1994). (c) D. Greszta, D. Mardare, and K. Matyjaszewski, Macromolecules, 27, 638 (1994). (f) M. Kato, M. Kamigaito, M. Sawamoto, and T. Higashimura, Macromolecules, 28, 1721 (1995). (g) K. Matyjaszewski, S. Gaynor, and J.-S. Wang, Macromolecules, 28, 2093 (1995). (h) J.-S. Wang and K. Matyjaszewski, J. Am. Chem. Soc., 117, 5614 (1995).
14. For examples of radical living polymerization, see: (a) T. Otsu and M. Yoshida, Makromol. Chem., Rapid Commun., 3, 127, 133 (1982). (b) D. H. Solomon, G. Waverly, E. Rizzardo, W. Hill, and P. Cacioli, U.S. Patent 4,581,429, 1986. (c) M. K. Georges, R. P. N. Veregin, P. M. Kazmaier, and G. K. Hamer, Macromolecules, 26, 5316 (1993). (d) B. B. Wayland, G. Poszmik, S. L. Mukerjee, and M. Fryd, J. Am. Chem. Soc., 116, 7943 (1994). (c) D. Greszta, D. Mardare, and K. Matyjaszewski, Macromolecules, 27, 638 (1994). (f) M. Kato, M. Kamigaito, M. Sawamoto, and T. Higashimura, Macromolecules, 28, 1721 (1995). (g) K. Matyjaszewski, S. Gaynor, and J.-S. Wang, Macromolecules, 28, 2093 (1995). (h) J.-S. Wang and K. Matyjaszewski, J. Am. Chem. Soc., 117, 5614 (1995).
15. For examples of radical living polymerization, see: (a) T. Otsu and M. Yoshida, Makromol. Chem., Rapid Commun., 3, 127, 133 (1982). (b) D. H. Solomon, G. Waverly, E. Rizzardo, W. Hill, and P. Cacioli, U.S. Patent 4,581,429, 1986. (c) M. K. Georges, R. P. N. Veregin, P. M. Kazmaier, and G. K. Hamer, Macromolecules, 26, 5316 (1993). (d) B. B. Wayland, G. Poszmik, S. L. Mukerjee, and M. Fryd, J. Am. Chem. Soc., 116, 7943 (1994). (c) D. Greszta, D. Mardare, and K. Matyjaszewski, Macromolecules, 27, 638 (1994). (f) M. Kato, M. Kamigaito, M. Sawamoto, and T. Higashimura, Macromolecules, 28, 1721 (1995). (g) K. Matyjaszewski, S. Gaynor, and J.-S. Wang, Macromolecules, 28, 2093 (1995). (h) J.-S. Wang and K. Matyjaszewski, J. Am. Chem. Soc., 117, 5614 (1995).
16. For examples of radical living polymerization, see: (a) T. Otsu and M. Yoshida, Makromol. Chem., Rapid Commun., 3, 127, 133 (1982). (b) D. H. Solomon, G. Waverly, E. Rizzardo, W. Hill, and P. Cacioli, U.S. Patent 4,581,429, 1986. (c) M. K. Georges, R. P. N. Veregin, P. M. Kazmaier, and G. K. Hamer, Macromolecules, 26, 5316 (1993). (d) B. B. Wayland, G. Poszmik, S. L. Mukerjee, and M. Fryd, J. Am. Chem. Soc., 116, 7943 (1994). (c) D. Greszta, D. Mardare, and K. Matyjaszewski, Macromolecules, 27, 638 (1994). (f) M. Kato, M. Kamigaito, M. Sawamoto, and T. Higashimura, Macromolecules, 28, 1721 (1995). (g) K. Matyjaszewski, S. Gaynor, and J.-S. Wang, Macromolecules, 28, 2093 (1995). (h) J.-S. Wang and K. Matyjaszewski, J. Am. Chem. Soc., 117, 5614 (1995).
17. H. R. Kricheldorf and G. Schwarz, Makromol. Chem., 184, 475 (1983).
18. H. R. Kricheldorf, Q.-Z. Zang, and G. Schwarz, Polymer, 23, 1821 (1982).
19. A. Vilsmeier and A. Haack, Ber., 60, 119 (1927).