Conclusion
Recent chemistry has been developed for the efficient preparation of oligomeric cyclic esters and carbonates. The current techniques have made it possible to prepare hundreds of kilograms of the cyclic oligomers per batch, and have made these materials available for study. Both methods of synthesis have been studied mechanistically. Purification to polymerization quality has been simply achieved in both cases, with selective reactions for removal of linear oligomers. The cyclic oligomers melt at 130–180°C (polyesters) or 180–200°C (polycarbonates), and have melt viscosities about 4 orders of magnitude lower than the parent high molecular weight polymers. Polymerization of the cyclic oligomers has been achieved with a variety of initiators, and using various techniques. Polymerization can be complete within minutes, and leads to very high molecular weight polyesters or polycarbonates without formation of byproducts, and with essentially no exotherm. The ring opening chemistry facilitates a variety of new copolymer reactions, and has made the fabrication of composite structures with very high fiber loadings possible.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
Preview
Unable to display preview. Download preview PDF.
References
H. Schnell, L. Bottenbruch, Ger. Pat. 1,229,101 (1966).
H. Schnell, L. Bottenbruch, Belg. Pat., 620 620, (1960).
H. Schnell, L. Bottenbruch, Makromol. Chem., 57, 1 (1962).
R. J. Prochaska, U. S. Pat. 3,274,214 (1966).
L. S. Moody, U. S. Pat, 3,155,683 (1964).
D. J. Brunelle, T. G. Shannon, Macromolecules, 24, 3035 (1991).
D. J. Brunelle, T. L. Evans, T. G. Shannon, E. P. Boden, et al., Polym. Prepr., 30(#2), 569 (1989).
D. J. Brunelle, E. P. Boden, T. G. Shannon, J. Am. Chem. Soc., 112, 2399 (1990)
D. J. Brunelle and M. F. Garbauskas, Macromolecules, 26, 2724 (1993).
D. J. Brunelle, Makromol. Chem., Macromol. Symp., 64, 65 (1992).
D. J. Brunelle and E. P. Boden, Polym. Prepr., 31, 399 (1991).
D. J. Brunelle and E. P. Boden, Makromol. Chem., Macromol. Symp., 54/55, 397 (1992).
E. P. Boden and D. J. Brunelle, Contemporary Topics in Polymer Science, Vol. 7, pp. 21–34, J. C. Salamone and J. S. Riffle, Eds, Plenum Press: New York (1992).
E. Aquino, W. J. Brittain, D. J. Brunelle, Polym. Prepr., 33 (#1), 1185 (1992).
E. Aquino, W. J. Brittain, D. J. Brunelle, Macromolecules, 25, 3827 (1992)
E. Aquino, W. J. Brittain, D. J. Brunelle, Polym. Prepr. 34 (#1): 865 (1993).
E. A. Aquino, W. J. Brittain, D. J. Brunelle, Polymer International, 33, 161 (1994).
E. C. Aquino, W. J. Brittain, D. J. Brunelle, Jour. Poly. Sci: Part A: Poly. Chem., 32, 741 (1994).
T. L. Evans, C. B. Berman, J. C. Carpenter, D. Y. Choi, D. A. Williams, Polym. Prep., 30 (#2), 573 (1989).
D. J. Brunelle and T. L. Evans, Contemporary Topics in Polymer Science, Vol. 7, pp 5–19, J._C. Salamone and J. Riffle, Eds., Plenum Press, New York (1992).
K. R. Stewart, Polym. Prepr., 30(#2), 140 (1989).
J. E. Bartmess, R. L. Hays, G. Caldwell, J. Am. Chem. Soc., 103, 1338 (1981).
T. L. Evans, D. J. Brunelle, A. J. Salem, K. R. Stewart, Polymer Preprints, 32(# 2), 176 (1991).
D. J. Brunelle, T. L. Evans, M. A. Vallance, K. R. Stewart, T. G. Shannon, D. A. Williams, D. J. Patterson, N. R. Rosenquist, W. Hilakos, U. S. Patent 4,740,583 (1988).
D. J. Brunelle and T. G. Shannon, Polymer Preprints, 31(# 1), 14 (1990).
D. J. Brunelle and T. G. Shannon, Makromol. Chem., Macromol. Symp., 42/43, 155 (1991).
D. J. Brunelle, T. L. Guggenheim, J. A. Cella, T. L. Evans, et al., U. S. Patent 4,980,453 (1990).
D. J. Brunelle and D. K. Bonauto, U. S. Patent 4,920,200 (1990).
D. J. Brunelle, H. O. Krabbenhoft, and D. K. Bonauto, Polym. Prepr., 34 (#1), 73 (1993).
D. J. Brunelle, H. O. Krabbenhoft, and D. K. Bonauto, Macromol. Symp., 77, 117–124 (1994).
D. J. Brunelle, Trends in Polymer Science, 3, 154 (1995).
T. L. Guggenheim, J. M. Fukuyama, J. J. Kelly, Eur. Pat. Appl., 402676 (1990); CA, 114:208077k.
T. L. Evans, U. S. Patent 4,699,974 (1987).
T. L. Evans and J. C. Carpenter, Polym. Prepr., 31(#1): 18 (1990). (b) T. L. Evans and J. C. Carpenter, Makromol. Chem. Macromol. Symp., 42/43: 177 (1991).
T. L. Evans and J. C. Carpenter, Makromol. Chem. Macromol. Symp., 42/43, 177 (1991).
T. L. Evans, T. J. Shea, C. B. Wasserman, J. R. Campbell, U. S. Patent 5,010,143 (1991).
T. L. Evans, N. R. Rosenquist, E. E. Bostick, U. S. Patent 4,746,724 (1988).
T. L. Evans, Eur. Pat. Appl., EP 249,809 (1987); CA 108:187816j.
T. Takekoshi, P. P. Anderson, U. S. Patents 4,695,612 and 4,766,199 (1988).
H. O. Krabbenhoft, E. P. Boden, Polym. Prep., 31(#1), 16 (1990).
N. R. Rosenquist, L. P. Fontana, Polym. Prep., 30(#2), 577 (1989)
D. J. Brunelle and T. G. Shannon, U. S. Patents 4,755,586 (1988), 4,794,160 (1988), 4,888,411 (1989), and 4,972,039 (1990).
S. D. Ross, E. R. Coburn, W. A. Leach, W. B. Robinson, J. Polym. Sci., 13, 406 (1954).
E. Repin and E. Papanikolau, J. Polym. Sci.,A-1, 7, 3426 (1969).
G. Wick and H. Zeitler, Angew. Makromol. Chem., 112, 59 (1983).
I. Goodman and B. F. Nesbitt, Polymer, 1, 384 (1960).
L. H. Peebles, M. W. Huffman, C. T. Ablett, J. Polym. Sci. (A-1), 7, 479 (1969).
G. C. East, A. M. Girshab, Polymer, 23, 323 (1982).
G. Montaudo, C. Puglisi, F. Samperi, Polymer Degradation and Stability, 42, 13 (1993).
E. Meraskentis and H. Zahn, Chem. Ber., 103, 3034 (1970).
F.-J. Muller, P. Kusch, J. Windeln, H. Zahn, Makromol. Chem., 184, 2487 (1983).
Y. Kitano, A. Ishitani, T. Ashida, Polymer Journal, 23, 949 (1991).
D. J. Brunelle, J. E. Bradt, J. Serth-Guzzo, T. Takekoshi, T. L. Evans, E. J. Pearce, Macromolecules, 31, 4782 (1998).
J. W. Hill, W. H. Carothers, J. Am. Chem. Soc., 55, 5031 (1933).
W. H. Carothers, J. W. Hill, J. Am. Chem. Soc., 55, 5043 (1933).
E. W. Spanagel, W. H. Carothers, J. Am. Chem. Soc., 57, 929 (1935).
G. L. Warner, D. J. Brunelle, P. R. Wilson, U. S. Patent 5,446,122 (1995).
Nippon Gijutsu Boeki Co., Japanese Patent 21873 (1971)
H. Jacobson, W. H. Stockmayer, J. Chem. Phys., 18, 1600 (1950).
D. J. Brunelle and T. Takekoshi, U. S. Patent 5,407,984 (1995).
D. J. Brunelle, G. Kailasam, J. Serth-Guzzo, P. Wilson, U. S. Patent 5,668,186(1997).
J. J. L. Bryant and J. A. Semlyen, Polymer, 38, 2475 (1997).
J. J. L. Bryant and J. A. Semlyen, Polymer, 38, 4531 (1997).
S. C. Hamilton, J. A. Semlyen, and D. M. Haddleton, Polymer, 39, 3241 (1998).
P. A. Hubbard, W. J. Britain, W. L. Mattice, D. J. Brunelle, Macromolecules, 31, 1518 (1998).
Measurement taken using a Brookfield viscometer, Carbone, J. and Pearce, E. J., personal communication.
Kambour, R.P., personal communication.
T. L. Evans, D. J. Brunelle, J. E. Bradt, E. J. Pearce, P. R. Wilson, U. S. Patent 5,466,744 (1995).
Author information
Authors and Affiliations
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2000 Kluwer Academic Publishers
About this chapter
Cite this chapter
Brunelle, D.J. (2000). Cyclic Oligomers of Polycarbonates and Polyesters. In: Semlyen, J.A. (eds) Cyclic Polymers. Springer, Dordrecht. https://doi.org/10.1007/0-306-47117-5_6
Download citation
DOI: https://doi.org/10.1007/0-306-47117-5_6
Publisher Name: Springer, Dordrecht
Print ISBN: 978-0-412-83090-7
Online ISBN: 978-0-306-47117-9
eBook Packages: Springer Book Archive