RING-OPENING POLYMERIZATION in .NET

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RING-OPENING POLYMERIZATION
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There are very few reported copolymerizations between cyclic monomers and carbon carbon double-bond monomers. Such copolymerizations would require a careful selection of the monomers and reaction conditions to closely match the reactivities of the different monomers and propagating centers. The almost complete absence of successes indicates that the required balancing of reactivities is nearly impossible to achieve. There are a few reports of copolymerizations between carbon carbon double-bond monomers and cyclic ethers or acetals [Higashimura et al., 1967; Inoue and Aida, 1984; Yamashita et al., 1966]. Some copolymerizations have been studied where one of the reactants is a compound not usually considered as a monomer. These include copolymerizations of epoxides and higher cyclic ethers with carbon dioxide, episul des with carbon dioxide and carbon disul de, and epoxides with sulfur dioxide [Aida et al., 1986; Baran et al., 1984; Chisholm et al., 2002; Inoue and Aida, 1989; Soga et al., 1977]. The copolymers are reported to be either 1 : 1 alternating copolymers or contain 1 : 1 alternating sequences together with blocks of the cyclic monomer. 7-12c Block Copolymers
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A wide range of different block copolymers have been synthesized by using the sequential addition method applicable to living polymer systems. These include various copolymers in which the different blocks are derived from two different cyclic monomers containing the same functional group, such as two cycloalkenes, cyclic ethers, lactams, lactones, Ncarboxy-a-amino acid anhydrides, and episul des [Cannizzo and Grubbs, 1988; Dreyfuss and Dreyfuss, 1989; Greene et al., 1988; Hashimoto, 2000; Imanishi, 1984; Inoue and Aida, 1989; Jedlinski et al., 1987; Sigwalt and Spassky, 1984; Yasuda et al., 1984]. There are very few reports of block copolymers of lactams or cyclic siloxanes produced by sequential addition, probably indicative of the exchange reactions that occur in polymerizations of these monomers. The sequential addition method also allows the synthesis of many different block copolymers in which the two monomers have different functional groups, such as epoxide with lactone, lactide or cyclic anhydride, cyclic ether with 2-methyl-2-oxazoline, imine or episul de, lactone with lactide or cyclic carbonate, cycloalkene with acetylene, and ferrocenophane with cyclosiloxane [Aida et al., 1985; Barakat et al., 2001; Dreyfuss and Dreyfuss, 1989; Farren et al., 1989; Inoue and Aida, 1989; Keul et al., 1988; Kobayashi et al., 1990a,b,c; Massey et al., 1998; Yasuda et al., 1984]. Further, there have been a number of successes in synthesizing block copolymers by sequential polymerization of a cyclic monomer and an alkene monomer. Examples include the combination of methyl methacrylate with epoxide, episul de or lactone, polystyrene with hexamethylcyclotrisiloxane, lactone or cyclic carbonate, and 2-isopropenylnaphthalene with hexamethylcyclotrisiloxane [Keul and Hocker, 1986; Krause et al., 1982; Kuroki et al., 1988a,b; Rhein and Schulz, 1985; Sigwalt and Spassky, 1984]. It turns out to be much easier to obtain block copolymers from these combinations than to obtain the corresponding statistical copolymers. Synthesis of a statistical copolymer requires that there not be a large imbalance between the various homo- and cross-propagation rates. Synthesis of a block copolymer by sequential addition requires that the system be living with one or the other cross-propagation proceeding at a reasonable rate. Thus, anionic copolymerization of styrene with ethylene oxide does not occur because the addition of alkoxide ion to the carbon carbon double bond and homopropagation of polystyryl anion are much less favored relative to addition of polystyryl anion to ethylene oxide and homopropagation of alkoxide anion. However, block
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COPOLYMERIZATION
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copolymerization is easily achieved by adding ethylene oxide to living polystyrene. Triblock polymers can be obtained in some systems by using appropriate difunctional initiators. Another route to block copolymers is the use of a macroinitiator, a telechelic homopolymer with appropriate end group, to initiate the polymerization of the second monomer. For example, polybutadiene containing a terminal hydroxyl group is reacted with triethylaluminum to form an aluminum alkoxide initiator that polymerizes lactide [Wang and Hillmyer, 2000]. Polystyrene and polysiloxane with p-toluenesulfonyl ester end groups initiate the polymerizations of 2-methyl-2-oxazoline and N-t-butylaziridine [Ishizu et al., 1985; Kazama et al., 1988]. The macroinitiator route has been used for many different combinations, including styrene NCA, ethylene oxide lactam, ethylene oxide phosphazene, ADMET-NCA [Allcock et al., 2001a,b; Brzezinska and Deming, 2001; Hashimoto, 2000; Janssen et al., 1988]. Coupling reactions have also been studied for producing block copolymers. Although not extensively studied, various architectures such as star and comb polymers have also been synthesized [Bielawski et al., 2000; Goethals et al., 2000]. 7-12d Zwitterion Polymerization
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Certain combinations of nucleophiles and electrophiles undergo polymerization without the need for initiator [Culbertson, 2002; Kobayashi and Saegusa, 1985; Kobayashi and Uyama, 2002; Saegusa, 1977, 1979, 1981]. The polymerization, referred to as zwitterion polymerization, proceeds via zwitterion intermediates. For example, polymerization between 2-oxazoline and b-propiolactone involves nucleophilic attack of 2-oxazoline on b-propiolactone to form the dimer zwitterion LXXXIX, which reacts with itself to form the tetramer zwitterion LXXXX. The latter reacts with itself and with LXXXIX to form octamer and hexamer
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