Hybrid phosphazene-organosilicon polymers: II. High-polymer and materials synthesis and properties

Two previous reviews describe some of the hybrid phosphazene organosilicon hydrids synthesized in a number of laboratories and in our own research program. See Refs. 2 and 3.

V. V. Kireev, G. S. Kolesnikov, and I. M. Raigorodskii,Russ. Chem. Rec. 38(8), 667 (1969) (Engl. transl.).

H. R. Allcock and D. J. Brennan,Organomet. Chem. 341, 231 (1988).

S. J. Clarson and J. A. Semlyen (eds.).Siloxane Polymers (Prentice Hall, Englewood Cliffs, NJ, 1993.

J. M. Zeigler and F. W. G. Fearon (eds.).Silicon-Based Polymer Science. A Comprechenire Resource, Advances in Chemistry Series (American Chemical Society. Washington, DC, 1990), Vol. 224.

M. Zeldin, K. J. Wynne, and H. R. Allcock (eds.),Inorganic and Organometallic Polymers, ACS Symposium Series (American Chemical Society. Washington, DC, 1988). Vol. 360.

H. R. Allcock,J. Inorg. Organometal. Polym. 2, 197 (1992).

Note that technological polysiloxanes fall into three main classes: The ?resins? or ?varnishes? that are used to bind glass fiber wire insulation; the linear short-chain silicone oils that are employed as transformer fluids, weter repellent, and specialized lubricants or hydraulic fluids: and the linear high polymers which, when cross-linked, yield silicone rubber.

H. N. Stokes,Am. Chem. J. 19, 782 (1897).

H. R. Alleock and R. L. Kugel,J. Am. Chem. Soc. 87, 4216 (1965).

H. R. Allcock, R. I. Kugel, and K. J. Valan,Inorg. Chem. 5, 1709 (1966).

H. R. Allcock and R. I. Kugel,Inorg. Chem. 5, 1716 (1966).

H. R. Allcock,Adv. Mater. 6, 106 (1994).

J. E. Mark, H. R. Allcock, and R. West,Inorganic Polymers (Prentice Hall, Englewood Cliffs, NJ, 1992).

H. R. Allcock, S. R. Pucher, and A. G. Scopelianos,Biomaterials 15, 563 (1994).

H. R. Allcock and S. Kwon,Macromolecules 21, 1980 (1988).

C. T. Laurencin, H. J. Koh, T. X. Neenan, H. R. Allcock, and R. Langer,J. Biomed. Mater. Res. 21, 1231 (1987).

H. R. Allcock and T. J. Fuller,J. Am. Chem. Soc. 103, 2250 (1981).

H. R. Allcock and F. W. Lampe,Contemporary Polymer Chemistry, 2nd ed., (Prentice Hall, Englewood Cliffs, NJ. 1990.

H. R. Allcock,Heteroatom Ring Systems and Polymers (Academic Press, New York, 1967).

H. R. Allcock, C. H. Kolich, and W. C. Kossa,Inorg. Chem. 16, 3362 (1977).

H. R. Allcock,Chem. Mater. 6, 1476 (1994).

E. G. Rochow,Silicon and Silicones (Springer-Verlag, Berlin, 1987).

T. C. Kendrick, B. Parbhoo, and I. W. White, inThe Chemistry of Organic Silicon Compounds, S. Patai and Z. Rappoport, eds. (John Wiley, New York, 1989).

B. Hardman and A. Torkelson, inEncyclopedia of Polymer Science and Engineering, 2nd ed. (Wiley Interscience, New York, 1987).

J. Liebig,Ann. Chem. 11, 139 (1934).

H. Rose,Ann. Chem. 11, 129 (1834).

A. N. Mujumdar, S. G. Young, R. I. Merker, and J. H. Merker, and J. H. Magill,Makromol. Chem. 190, 2293 (1989).

M. S. Sennett, G. L. Hagnauer, R. E. Singler, and G. Davies,Macromolecules 19, 959 (1986).

H. R. Allcock, and R. J. Best,Can. J. Chem. 42, 447 (1964).

F. Seel, J. Langer,Z. Anorg. Allg. Chem. 295, 317 (1958).

R. Schmutzler,Inorg. Synth. 9, 76 (1967).

H. R. Allcock and G. Y. Moore,Macromolecules 8, 377 (1975).

H. R. Allcock, R. J. Ritchie, and R. J. Harris,Macromolecules 13, 1332 (1980).

I. Manners, G. H. Riding, J. A. Dodge, and H. R. Allcock,J. Am. Chem. Soc. 111, 3067 (1989).

H. R. Allcock, K. D. Lavin, and G. H. Riding,Macromolecules 18, 1340 (1985).

A. G. Scopelianos, J. P. O'Brien, and H. R. Allcock.J. Chem. Soc. Coem Commun. 198 (1980).

H. R. Allcock, J. A. Dodge, I. Manners, and G. H. Riding,J. Am. Chem. Soc. 113, 9596 (1991).

H. R. Allcock and M. L. Turner,Macromolecules 26, 3 (1993).

H. R. Allcock, J. A. Dodge, and I. Manners,Macromolecules 26, 11 (1993).

I. Manners and H. R. Allcock.J. Am. Chem. Soc. 111, 5478 (1989).

H. R. Allcock, S. M. Coley, I. Manners, K. B. Visscher, M. Parvez., O. Nuyken, and G. Renner,Inorg. Chem. 32, 5088 (1993).

E. D. Hornbaker and H. M. Li, U.S. Patent 4.198.381 (1980).

R. De Jaeger, M. Helioui, and E. Puskaric, U.S. Patent 4.377.558 (1983).

M. Helioui, R. De Jaeger, E. Puskaric, and J. Heubel,Makromol. Chem. 183, 1137 (1982).

G. D'Halluin, R. De Jaeger, J. P. Chambrette, and Ph. Potin,Macromolecules 25, 1254 (1992).

a)R. De Jaeger and Ph. Potin,Phosphorus Sulfur Silicon 76, 223 (1993).

Ph. Potin and R. De Jaeger,Phosphorus Sulfur Silicon 76, 227 (1993).

C. H. Honeyman, I. Manners, C. T. Morrssey, and H. R. Allcock.J. Am. Chem. Soc. 117, 7035 (1995).

P. Wisian-Neilson and R. H. Neilson,J. Am. Chem. Soc. 102, 2848 (1980).

R. H. Neilson, R. Hani, P. Wisian-Neilson, J. J. Meister, A. K. Roy, and G. C. Hagnauer.Macromolecules 20, 910 (1987).

E. P. Flindt and H. Rose,Z. Anorg. Allg. Chem. 428, 204 (1977).

R. A. Montague and K. Matyjaszewski,J. Am. Chem. Soc. 112, 6721 (1990).

R. A. Montague and K. Matyjaszewski,Polym Preprints 31(2), 679 (1990).

D. I. Herring,Chem. Ind. (London) 717 (1960).

G. Tesi, C. P. Haber, and C. M. Douglas,Proc. Chem. Soc. London 219 (1960).

K. Matyjaszewski, M. K. Moore, and M. L. White,Macromolecules 26, 6741 (1993).

U. Franz, O. Nuyken, and K. Matyjaszewski.Macromolecules 26, 3723 (1993).

K. Matyjaszewski, U. Franz, R. A. Montague, and M. L. White,Polymer 35, 5005 (1994).

K. Matyjaszewski, R. Montague, J. Dauth, and O. Nuyken,J. Polym. Sci. Part A Polym. Chem. 30, 813 (1992).

S. I. Belykh, S. M. Zhivukhin, V. V. Kireev, and G. S. Kolesniko,Russ. J. Inorg. Chem. 14(5), 668 (1969) (Engl. transl.).

V. V. Kireev, G. S. Kolesnikov, I. M. Raigorodskii, and P. O. Okulevich,J. Gen. Chem. USSR 41, 798 (1971) (Engl. transl.).

A. A. Volodin, V. V. Kireev, V. V. Korshak, E. A. Filippov, and V. M. Chukova,J. Gen. Chem. USSR 42, 1493 (1972) (Engl. transl.).

L. M. Volkova, V. V. Pisarenko, N. M. Voichenko, K. A. Andrianov, M. I. Kabachnik,Bull. Acad. Sci. USSR Div. Chem. Sci. 3, 470 (Engl. transl.) (1972).

K. D. Gallicano, R. T. Oakley, N. L. Paddock, and R. D. Sharma,Can. J. Chem. 59, 2654 (1981).

H. P. Calhoun, R. H. Lindstrom, R. T. Oakley, and N. L. Paddock.J. Chem. Soc. Chem. Communn. 343 (1975).

S. M. Zhivukhin, V. B. Tolstoguzov, and A. I. Ivanov,Russ. J. Inorg. Chem. 7(9), 1134 (1962) (Engl. transl.).

S. N. Borisov, M. G. Voronkov, and E. Ya. Lukevits,Organosilicon Derivatives of Phosphorus and Sulfur (Plenum Press, New York London, 1971). Chap. 1.

T. N. Beloglazova, V. V. Kireyev, H. S. Kolesnikov, and I. M. Raigorodskii,Polym. Sci. USSR A 13(7), 1828 (1971) (Engl. transl.).

S. I. Belykh, S. M. Zhivukhin, V. V. Kireyev, and H. S. Kolesnikov,Polym. Sci. USSR 11, 711 (1969) (Engl. transl.).

D. J. Brennan. Doctoral thesis (The Pennsylvania State University, University Park, 1987).

H. R. Allcock, D. J. Brennan, and R. W. Allen,Macromolecules 18, 139 (1985).

C. W. Allen, J. L. Desorcie, and K. Ramachandran,J. Chem. Soc. Dalton Trans 2843 (1984).

H. R. Allcock, D. J. Brennan, J. M. Graaskamp, and M. Parvez,Organometallics 5, 2434 (1986).

H. R. Allcock, D. J. Brennan, B. S. Dunn, and M. Parvez,Inorg. Chem. 27, 3226 (1989).

H. R. Allcock, D. J. Brennan, and B. S. Dunn,Macromolecules 22, 1534 (1989).

H. R. Allcock, D. J. Brennan, and J. M. Graaskamp,Macromolecules 21, 1 (1988).

H. R. Allcock, J. L. Desorcie, and G. H. Riding,Polyhedron 6, 119 (1987).

T. L. Evans, D. B. Patterson, P. R. Suszko, and H. R. Allcock.Macromolecules 14, 218 (1981).

N. L. Paddock, T. N. Ranganathan, and S. M. Todd,Can. J. Chem. 49, 164 (1971).

K. Ramachandran and C. W. Allen,J. Am. Chem. Soc. 104, 2396 (1982).

H. R. Allcock, W. D. Coggio, M. Parvez, and M. Turner,Organometallics 10, 677 (1991).

P. Wisian-Neilson, R. R. Ford, R. H. Neilson, and A. K. Roy,Macromolecules 19, 2089 (1986).

R. H. Neilson and P. Wisian-Neilson,Chem. Rev. 88, 541 (1988).

H. R. Allcock,Phosphorus-Nitrogen Compounds: Cyclic,Linear, and High Polymeric Systems (Academic Press, New York. 1972).

K. Hills and R. A. ShawJ. Chem. Soc. London 130 (1964).

B. Capon, K. Hills, and R. A. Shaw.J. Chem. Soc. London 4059 (1965).

M. Becke-Goehring, K. John, and E. Fluck,Z. Anorg. Allg. Chem. 302, 103 (1959).

T. Moeller, and S. G. Kokalis,J. Inorg. Nucl. Chem. 25, 1397 (1963).

V. V. Kireev, V. A. Kovyazin, V. M. Kopylov, M. G. Zaitseva, and G. I. Mitropol'skaya,J. Gen. Chem. USSR 54(8), 1692 (1984) (Engl. transl.).

H. R. Allcock and W. D. Coggio,Macromolecules 23, 1626 (1990).

H. R. Allcock, C. J. Nelson, and W. D. Coggio,Organometallics 10, 3819 (1991).

J. C. van de Grampel, A. P. Jekel, R. Puyenbroek, T. J. Arling, M. C. Faber, W. Fransen, A. Meetsma, and J. H. Wubbels,Phosphorus Sulfur Silicon 76, 215 (1993).

H. R. Allcock, D. F. Smith, Y. B. Kim, and J. J. Fitzgerald,Macromolecules 27, 5206 (1994).

T. L. Evans, T. J. Fuller, and H. R. Allcock,J. Am. Chem. Soc. 101, 242 (1979).

H. R. Allcock, T. L. Evans, and T. J. Fuller,Inorg. Chem. 19, 1026 (1980).

H. R. Allcock, W. D. Coggio, R. S. Archibald, and D. J. Brennan,Macromolecules 22. 3571 (1989).

Yu. E. Ovchinnikov, V. E. Shklover, Yu. T. Struchkov, A. A. Remizova, V. M. Kopylov, V. A. Kovyazin, and V. V. Kireyev,Z. Anorg. Allg. Chem. 523, 14 (1985).

W. D. Coggio, Doctoral thesis (The Pennsylvania State University, University Park. 1991).

H. R. Allcock and M. S. Connolly,Macromolecules 18, 1330 (1985).

H. R. Allcock, J. L. Schmutz, and K. M. Kosydar,Macromolecules 11, 179 (1978).

W. T. Ferrar, F. V. DiStefano, and H. R. Allcock.Macromolecules 13, 1345 (1980).

H. R. Allcock,Polymer 21, 673 (1980).

H. R. Allcock, A. G. Gardner, and K. M. Smeltz,Macromolecules 8, 36 (1975).

H. R. Allcock, A. G. Scopelianos, R. R. Whittle, and N. M. Tollefson,J. Am. Chem. Soc. 105, 1316 (1983).

C. Eaborn,Organosilicon Compounds (Butterworth, London, 1960).

G. F. Roedel,J. Am. Chem. Soc. 71, 269 (1949).

J. P. O'Brien, W. T. Ferrar, and H. R. Allcock,Macromolecules 12, 108 (1979).

H. R. Allcock and W. D. Coggio,Macromolecules 26, 764 (1993).

J. H. L. Crommen, J. Vandorpe, and F. H. Schacht,Makromol. Chem. 193, 1261 (1992).

R. Puyenbrock, A. P. Jekel, and J. C. van de Grampel,J. Inorg. Organomet. Polym. 1, 105 (1991).

J. C. van de Grampel, R. D. van de Grampel, R. H. J. Hendriks, A. P. Jekel, A. Meetsma. E. G. M. Veldman, and J. H. Wubbels,Phosphorus Sulfur Silicon 93?94, 273 (1994).

R. H. Neilson, and P. J. Wisian-Neilson,Macromol. Sci. Chem. A 16, 1981 (1981).

P. Wisian-Neilson: and M. S. Islam,Macromolecules 22, 2026 (1989).

P. Wisian-Neilson, M. S. Islam, and M. A. Schaefer,Phosphorus Sulfur Silicon 41, 135 (1989).

P. Wisian-Neilson, M. A. Schaefer, and M. S. Islam.Polym. Preprints 30, 185 (1989).

H. R. Allcock, R. J. Fitzpatrick, and I., Salvati,Chem. Mater. 3, 1120 (1991).

H. R. Allcock, J. S. Rutt, and R. J. Fitzpatrick,Chem. Mater. 3, 442 (1991).

H. R. Allcock, R. J. Fitzpatrick, and L. Salvati,Chem. Mater. 4, 769 (1992).

H. R. Allcock, R. J. Fitzpatrick, and L. Salvati,Chem. Mater. 4, 450 (1991).

H. R. Allcock, and D. E. Smith,Chem. Mater. 7, 1469 (1995).

S. Krause,J. Macromol. Sci.-Res. Macromol. Chem. C7(2), 251 (1972).

O. Olabisi, L. M. Robeson and M. T. Shaw,Polymer-Polymer Miscibility (Academic Press, New York, 1979), p. 207.

P. C. Painter,Macromolecules 22, 570 (1989).

D. R. Paul, J. W. Barlow, and H. Keskkula, inPolymer Blends, H. F. Mark, N. M. Bilakes, C. G. Overberger, and G. Menges, eds. (Encyclopedia of Polymer Science and Engineering, 2nd ed.) (Wiley-Interscience. New York, 1988), Vol. 12, pp. 399?461.

D. R. Paul and L. H. Sperling (eds.),Multicomp. Polym. Mater., Adv. Chem. Ser. 211 (ACS, Washington, DC, 1986).

J. A. Manson, and L. H. Sperling,Polymer Blends and Composites (Plenum Press, New York, 1986).

K. B. Visscher, Doctoral thesis (The Pennsylvania State University, University Park. 1993).

L. H. Sperling,Interpenetrating Polymer Networks and Related Materials (Plenum Press, New York, 1981).

L. H. Sperling,Chemtech 18, 104 (1988).

H. F. Mark, N. M. Bikales, C. G. Overberger, and G. Menges (eds.).Encyclopedia of Polymer Science and Engineering, 2nd ed., Vol. 8 (Wiley and Sons. New York, 1987). pp. 279.

L. H. Sperling,Interpenetrating Polymer Networks and Related Materials (Plenum Press. New York, 1981).

B. K. Coltrain, W. T. Ferrar, C. J. T. Landry, and T. R. Molaire,Polym. Prepr. 32, 477 (1991).

B. K. Coltrain, W. T. Ferrar, C. J. T. Landry, T. R. Molaire, and N. Zumbulyadis,Chem. Mater. 4, 358 (1992).

W. T. Ferrar, B. K. Coltrain, C. J. T. Landry, V. K. Long, T. R. Molaire, and D. E. Schildkraut, inInorganic and Organometallic Polymers II. P. Wisian-Neilson, H. R. Allcock, and J. K. Wynne (eds.)ACS Symp. Ser. 572, 258 (1994).

G. Facchin, G. Fantin, M. Gleria, M. Guglielmi, and F. Spizzo,Polym. Preprints 34, 322 (1994).

C. S. Reed and H. R. Allcock, unpublished results (1995).

J. Brandrup and E. H. Immergut (eds.),Polymer Handbook, 3rd ed. (Wiley, New York, 1989), p. V-37.

Ibid. (eds.),Polymer Handbook, 3rd ed., (Wiley, New York, 1989), p. V-37.

P. Wisian-Neilson, L. Bailey, and M. Bahadur,Macromolecules 27, 7713 (1994).

H. R. Allcock, C. J. Nelson, W. D. Coggio, I. Manners, W. J. Koros, D. R. B. Walker, and L. A. Pessan,Macromolecules 26, 1493 (1993).

T. Higashimura, T. Masuda, and M. Okada,Polym. Bull. 10, 114 (1983).

S. M. Zhivukhin, V. B. Tolstoguzov, and S. I. Belykh,Russ. J. Inorg. Chem. 9, 73 (1964). (Engl. transl.).

N. N. Kalmykova, V. V. Kireyev, V. V. Korshak, I. M. Raigorodskii, and V. I. Gorokhov.Polym. Sci. USSR A15:10, 2474 (1973) (Engl. transl.).

V. V. Korshak, S. V. Vinogradova, M. A. Andreyeva, Ye. G. Bulycheva, K. A. Andrianov, A. A. Zhdanov, Ye. F. Rodionova, and N. G. Vasilenko,Polym. Sci. USSR A 23:2, 477 (1981) (Engl. transl.).