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RADICAL CHAIN POLYMERIZATION
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itself, reacts rapidly with the propagating radical to decrease the concentration of propagating radicals suf ciently that conventional bimolecular termination is negligible. The propagating radical concentration is much lower than that of the dormant species; speci cally, K is small, and this results in living radical polymerization with control of molecular weight and molecular weight distribution. The general characteristics of ATRP described in Sec. 3-15b apply to NMP, that is, reaction variables control polymerization rate, molecular weight, and PDI in the same way [Ananchenko and Fischer, 2001; Greszta and Matyjaszewski, 1996; LacroixDesmazes et al., 2000, 2001; Lutz et al., 2001; Yoshikawa et al., 2002]. NMP with TEMPO generally requires higher temperatures (125 145 C) and longer reaction times (1 3 days) compared to ATRP, and only styrene and 4-vinylpyridine polymerizations proceed with good control of molecular weight and polydispersity. Narrow molecular weight distributions with PDI below 1.1 1.2 are dif cult to achieve with other monomers. The sluggishness of TEMPO systems is ascribed to K values being too low. K values are lower than in ATRP. Various techniques have been used to increase Rp . Adding a conventional initiator with a long half-life (slowly decomposing) to continuously generate reactive radicals throughout the reaction works well. Another technique is the addition of an acylating agents to reduce the concentration of nitroxide radicals via their acylation [Baumann and Schmidt-Naake, 2001]. Self-initiation in styrene polymerization also enhances the reaction rate. However, it is not easy to increase reaction rates and maintain narrow PDI. Some improvements occurred by changing to nitroxides with a hydrogen on at least one of the a-carbons of the piperidine ring, in contrast to TEMPO, which has no hydrogens on a-carbons. However, the major breakthrough came by using sterically hindered alicyclic nitroxides with a hydrogen on one of the a-carbons. t-Butyl 2-methyl-1-phenylpropyl nitroxide (LVIII) and t-butyl 1-diethylphosphono-2,2-dimethylpropyl nitroxide (LIX) are examples of
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nitroxides that yield considerably faster polymerizations with control of molecular weight and polydispersity [Benoit et al., 2000a,b; Farcet et al., 2002; Grimaldi et al., 2000; Le Mercier et al., 2002]. These nitroxides and their corresponding alkoxyamines have allowed NMP of styrenes at lower temperatures and also extended NMP to monomers other than styrene. Acrylates, acrylamides, 1,3-dienes, and acrylonitrile polymerizations proceed with good molecular weight and PDI control, especially when ne-tuned in terms of the relative amounts of nitroxide radical, alkoxyamine, and conventional initiator and the reaction conditions (temperature, concentrations). The upper molecular weight limit of NMP is about 150,000 200,000, similar to the situation for ATRP. NMP has not been extended to methacrylate monomers, in contrast to ATRP, which is successful with methacrylates. Many attempts to polymerize methacrylates by NMP have been unsuccessful, resulting in low conversions and/or broad PDI [Hawker et al., 2001]. This is generally ascribed to degradation of propagating radicals via b-hydrogen abstraction
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3-240
by nitroxide (Eq. 3-240) followed by the formed hydroxylamine acting as a chain-transfer agent to terminate another propagating chain. There is one report of successful NMP of methacrylate monomers [Yousi et al., 2000], but many other workers using very similar reaction conditions were unsuccessful [Burguiere et al., 1999; Cheng and Yang, 2003]. Statistical, gradient, and block copolymers as well as other polymer architectures (graft, star, comb, hyperbranched) can be synthesized by NMP following the approaches described for ATRP (Secs. 3-15b-4, 3-15b-5) [Hawker et al., 2001]. Block copolymers can be synthesized via NMP using the one-pot sequential or isolated macromonomer methods. The order of addition of monomer is often important, such as styrene rst for styrene-isoprene, acrylate rst for acrylate-styrene and acrylate-isoprene [Benoit et al., 2000a,b; Tang et al., 2003]. Different methods are available to produce block copolymers in which the two blocks are formed by different polymerization mechanisms: 1. A dual-function alkoxyamine with an appropriate functional group, such as the hydroxyl-containing alkoxyamine LX, can initiate anionic polymerization (in the presence of