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P CH2 P CH2
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N OH CH2 N HOOC XXXXII XXXXIII
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the hydroxyl and nitrogen functions. The metal is separated by ltration of the polymer and can be recovered from the polymer by changing the pH. Other chelating polymers have been studied for removal of pertechnetate ion, TcO , from contaminated groundwater at nuclear 4 reactor facilities [Alexandratos and Natesan, 1999; Bonnesen et al., 2000]. Polymers containing crown ether or cryptand macrocyclic ligands bind and separate various cations [Jaycox and Smid, 1981; Mathias and Al-Jumah, 1980]. Polymers containing chiral groups are useful for resolving racemic mixtures into the individual enantiomers [Kiniwa et al., 1987; Mathur et al., 1980; Wulff et al., 1980]. For example, the copper(II) complex of XXXXIII (either the R- or S-enantiomer) resolves racemates of amino acids [Sugden et al., 1980]. The separation is based on the formation of a pair of diastereomeric complexes from the reaction of the polymer reagent with the two enantiomers. One of the enantiomers is complexed more strongly than the other and this achieves separation of the enantiomers. A polymer drug can be synthesized by the covalent bonding of a drug to a polymer or the synthesis and (co)polymerization of a monomer containing the drug moiety [Callant and Schacht, 1990; Donaruma and Vogl, 1978; Hsieh, 1988; Levenfeld et al., 1990; Ottenbrite
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REACTIONS OF POLYMERS
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and Sunamoto, 1986]. (Ionic bonding or complexing of a drug to the polymer are other approaches.) Polymer drugs are of interest since they offer a number of potential advantages relative to the corresponding low-molecular-weight drugs. The action of a polymer drug usually depends on in vivo hydrolytic or enzymatic cleavage of the drug moiety from the polymer. This gives the advantage of a delayed and sustained release of the drug over a longer time period with a corresponding decrease in side effects such as irritation, intolerance, and toxicity. There is the potential to tailor-make a polymer drug with a speci c required solubility, rate of diffusion, and increased or decreased activity by appropriate choice of the polymer and drug. Other possibilities include the synthesis of polymer drugs with negligible absorptivity for situations where localized drug action is desired (e.g., skin treatment), the ability to design drugs capable of getting to a speci c organ (via appropriate af nity groups) in the desired amounts at the required time, and the coupling of two or more drugs onto the same polymer to achieve enhanced or synergistic activity. The term polymer drug also includes the physical encapsulation of a low-molecular-weight drug by a polymer. Drug action requires the hydrolytic or enzymatic degradation of the polymer. Such materials can show many of the advantages of polymer drugs in which the drug is chemically bound to a polymer. Also of interest are polymer drugs that do not depend on release of a lowmolecular-weight drug moiety for activity but possess activity as polymers. Polymeric agricultural chemicals such as polymer herbicides, fertilizers, and insecticides have also been studied [Lohmann and d Hondt, 1987; Scher, 1977; Shambhu et al., 1976]. Controlled and slow release of the herbicide, fertilizer, or insecticide moiety has the advantages of prolonged action and decreased indiscriminant pollution of the environment. Other polymer reagents of interest include polymer antioxidants, ame retardants, and UV stabilizers as additives to polymers [Scott, 1987, 1989; Vogl et al., 1985]. The advantage of the polymeric additive is decreased migration or leaching from the polymer compared to the corresponding low-molecular-weight additive.
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9-13
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POLYMER CATALYSTS
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Some examples of polymer catalysts have previously been described hydrogenation by the polymer rhodium catalyst (II) (Sec. 9-1g) and ester hydrolysis by poly[4(5)-vinylimidazole] (VII) (Sec. 9-1j). Many other types of polymer catalysts have been described [Akelah and Sherrington, 1983; Bergbeiter, 2001, 2002; Blossey and Ford, 1989; Corma and Garcia, 2002; Fan et al., 2002; Hodge and Sherrington, 1980; Leadbeater and Marco, 2002; Mathur et al., 1980; McNamara et al., 2002; Sherrington, 2001]. The physical method of carrying out a reaction using a polymer catalyst is the same as the scheme described in Fig. 9-1, with the exception that two low-molecular-weight substances, instead of only one, are usually involved. Many of the general advantages of polymer catalysts have been described (Sec. 9-11b). Polymer catalysts are often easier to handle, less toxic, and more stable toward moisture and atmospheric contaminants. The products of reactions catalyzed by lowmolecular-weight catalysts, especially metal catalysts, are often contaminated by the catalysts. Catalyst removal can be dif cult in such systems but necessary if the properties of the products are adversely affected by the presence of catalyst. Catalyst removal is much simpler with the use of a polymer catalyst. Further, the recovery and regeneration of an expensive catalyst is facilitated since the polymer catalyst can be separated from the reaction mixture by ltration. Various polymer acids are used as polymer catalysts. Sulfonated polystyrene (Eq. 9-39) has been used to catalyze a variety of acid-catalyzed reactions, including acetal and ketal
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