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Polymerizations in Supercritical Carbon Dioxide Chemical Reviews, 1999, Vol. 99, No. 2 561 Scheme 13. Oxidative Coupling of 2,6-Dimethylphenol (2) Jessop, P. G.; Ikariya, T.; Noyori, R. Organometallics 1995, 14, 1510. (3) Kaupp, G. Angew. Chem., Int. Ed. Engl. 1994, 33, 1452. (4) DeSimone, J. M.; Guan, Z.; Elsbernd, C. S. Science 1992, 257, 945-947. (5) Barer, S. J.; Stern, K. M. In Catalytic Activation of Carbon Dioxide; Ayers, W. M., Ed.; American Chemical Society: Wash- ington, DC, 1988; p 1. (6) Quinn, E. L.; Jones, C. L. Carbon Dioxide; Reinhold: New York, 1936. (7) Hyatt, J. A. J. Org. Chem. 1984, 49, 5097-5101. (8) Rindfleisch, F.; DiNoia, T.; McHugh, M. A. Polym. Mater. Sci. Eng. 1996, 74, 178. (9) Yilgor, I.; McGrath, J. E.; Krukonis, V. J. Polym. Bull. 1984, 12, 499. (10) Krukonis, V. Polym. News 1985, 11, 7-16. (11) Guan, Z.; Combes, J. R.; Menceloglu, Y. Z.; DeSimone, J. M. Macromolecules 1993, 26, 2663-2669. (12) Hoefling, T. A.; Newman, D. A.; Enick, R. M.; Beckman, E. 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(33) Shieh, Y.-T.; Su, J.-H.; Manivannan, G.; Lee, P. H. C.; Sawan, S. P.; Spall, W. D. J. Appl. Polym. Sci. 1996, 59, 695-705. (34) Hsiao, Y.-L.; Maury, E. E.; DeSimone, J. M.; Mawson, S. M.; Johnston, K. P. Macromolecules 1995, 28, 8159-8166. (35) Watkins,J.J.;McCarthy,T.J.Macromolecules1994,27,4845- 4847. (36) Watkins,J.J.;McCarthy,T.J.Macromolecules1995,28,4067- 4074. (37) Kwag, C.; Gerhardt, L. J.; Khan, V.; Gulari, E.; Manke, C. W. Polym. Mater. Sci. Eng. 1996, 74, 183. (38) Garg, A.; Gulari, E.; Manke, C. W. Macromolecules 1994, 27, 5643. (39) Mertsch, R.; Wolf, B. A. Macromolecules 1994, 27, 3289-3294. (40) Elliott, J. R.; Srinivasan, G.; Dhanuka, M.; Akhaury, R. United States Patent 5,128,382, 1992. (41) Srinivasan,G.;Elliot,J.R.Ind.Eng.Chem.Res.1992,31,1414- 1417. (42) Wessling, M.; Borneman, Z.; Van Den Boomgaard, T.; Smolders, C. A. J. Appl. Polym. Sci. 1994, 53, 1497-1512. (43) Goel, S. K.; Beckman, E. J. AIChE J. 1995, 41, 357-367. (44) Barrett, K. E. J. Dispersion Polymerization in Organic Media; John Wiley and Sons: New York, 1975. (45) Arshady, R. Colloid Polym. Sci. 1992, 270, 717. (46) Miller,C.M.;Blythe,P.J.;Sudol,E.D.;Silebi,C.A.;El-Aasser, M. S. J. Polym. Sci.: Part A: Polym. Chem. 1994, 32, 2365- 2376. (47) El-Aasser, M. S.; Miller, C. M. In Polymeric Dispersions: Prin- ciples and Applications; Asua, J. M., Ed.; Kluwer Academic Press: Boston, 1997; Vol. 335, p 109-126. acrylate (DMAEA)] and CO2-soluble polymeric amines [poly(FOA-co-vinylpyridine) (10) and poly(FOA-co- DMAEA) (11)] were used in the reaction. While the small molecule bases should produce a heterogeneous catalyst, the polymeric amines should increase the solubility of the catalyst, although the solubility characteristics of either system were not reported. It was hoped that the polymeric amines would result in a dispersion polymerization and give higher yields. Although the polymeric amines produced a stable latex, an increase in yields or molecular weights of polymer normally associated with dispersion poly- merization was not observed. Because polystyrene is miscible with poly(2,6- dimethylphenylene oxide), it was thought to be a good candidate as the CO2-phobic component in surfac- tants for the dispersion polymerization of 2,6-di- methylphenol. Random and block copolymers of styrene and FOA were synthesized and were added to the dimethylphenol polymerizations.60 Presence of the random copolymer led to higher yields but not higher molecular weights. However, the reaction stabilized with the block copolymer gave higher yields (up to 86%) and higher molecular weights (up to 1.7 × 104 g/mol). Thus, block copolymers of FOA and styrene were effective stabilizers for the dispersion polymerization of 2,6-dimethylphenol in supercritical CO2. IV. Conclusions The numerous examples presented here demon- strate that supercritical CO2 is rapidly becoming a viable alternative solvent for polymerizations. Su- percritical CO2 has been used as the continuous phase for all types of chain-growth and step-growth polymerization mechanisms, including metal-cata- lyzed, free-radical, and ionic processes. Several unique aspects of supercritical CO2, including the ability to tailor the solvent quality by changing the pressure, have been exploited to prepare materials with various morphologies and properties. In addition, the design and synthesis of surfactants which are interfacially active in supercritical CO2 has opened the door for the preparation of a wide range of polymeric materi- als in this unique solvent. V. References (1) McHugh, M. A.; Krukonis, V. J. Supercritical Fluid Extraction: Principles and Practice, 2nd ed.; Butterworth-Heineman: Stone- ham, 1993.PDF Image | Polymerizations in Supercritical Carbon Dioxide
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