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and similarly between styrene radical and maleic anhydride monomer:
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The monomer complex participation (MCP) mechanism suggests that alternation results from homopolymerization of a 1 : 1 complex formed between donor and acceptor monomers [Cowie, 1989; Furukawa, 1986]:
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The pros and cons of the two mechanisms have been reviewed [Coote et al., 1998; Hall and Padias, 2001]. Spectroscopic (UV, visible, and NMR) evidence supports the formation of charge transfer complexes between electron-donor and electron-acceptor monomers [Dodgson and Ebdon, 1977; Hirai, 1976; Kuntz et al., 1978]. For example, color develops when many comonomer pairs are mixed and the color disappears on polymerization. The stereochemistry of alkyl vinyl ether copolymerizations with fumaronitrile and maleonitrile supports the complex mechanism [Butler and Do, 1989; Olson and Butler, 1984]. The two copolymerizations yield different stereochemical results, indicating that the cis and trans arrangements of substituents in maleonitrile and fumaronitrile, respectively, are preserved in the copolymer. If maleonitrile and fumaronitrile entered the copolymer as individual monomer molecules, instead of as part of a complex with the alkyl vinyl ether, the two copolymers would possess the same stereochemistry. Contradictory evidence for the complex mechanism was found during radical-trapping experiments in the copolymerization of N-phenylmaleimide (NPM) and 2-chloroethyl vinyl ether (CEVE) [Jones and Tirrell, 1986, 1987; Prementine et al., 1989]. Only N-phenylmaleimide added to the radical trap, whereas both monomers should have added if reaction involved the 1 : 1 complex of NPM and CEVE. Perhaps the strongest argument against the MCP mechanism is that charge-transfer complexes have not been isolated and are not known to undergo chemical reactions. Some pairs of very strongly electron-donor and electron-acceptor monomers, such as p-methoxystyrene and dimethyl cyanofumarate, undergo spontaneous alternating copolymerizations without any added free-radical initiator, although heat may be required [Hall and Padias, 1997, 2001]. Initiation involves reaction of the comonomer pair to form a diradical,
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which then propagates. The process, referred to as charge-transfer polymerization, is complicated. Some comonomer pairs do not form alternating copolymers, but instead form homopolymer and/or cyclobutane derivatives by 2 2 -cycloaddition between the two monomers. For example, vinylidene cyanide and alkyl vinyl ether react spontaneously at 25 C to form the separate homopolymers of the two monomers plus a small amount of the cyclobutane adduct. The addition of a Lewis acid such as zinc chloride, dialkylaluminum chloride, and alkylaluminum sesquichloride (AlR1.5Cl1.5) to some comonomer pairs increases the tendency to form alternating copolymers. Comonomer pairs that are mildly alternating become strongly alternating [Ban et al., 2000; Cowie, 1989; Furukawa, 1986]. Even more surprising, strongly alternating behavior occurs between monomers that seldom copolymerize or whose alternation tendency is very low. Thus alternating copolymerization is achieved between electronacceptor monomers such as acrylonitrile, methyl acrylate, methyl methacrylate, and methyl vinyl ketone and electron-donor monomers such as propene, isobutylene, vinyl chloride, vinylidene chloride, and vinyl acetate. A consideration of the r values in Table 6-2 for these comonomer pairs clearly indicates that the alternating tendency is not high in the absence of the Lewis acid. In the presence of the Lewis acid these comonomer pairs become strongly alternating. Two mechanisms have been proposed to explain the effect of Lewis acids, both involving initial complexation of the Lewis acid with the electron-acceptor monomer to produce a binary complex with enhanced electron-acceptor properties. The binary complex participates in copolymerization either through a cross-propagation mechanism or via interaction with the electron-donor monomer to form a ternary complex that subsequently undergoes homopropagation. Both mechanisms explain why copolymerization is possible with monomers such as propene or isobutylene, which do not homopolymerize as a result of degradative chain transfer. Degradative chain transfer is less competititve with polymerization through the binary or ternary complex. Both the cross-propagation and complex mechanisms may be operative in alternating copolymerizations with the relative importance of each depending on the particular reaction system. The tendency toward alternation, with or without added Lewis, acid, is temperatureand concentration-dependent. Alternation decreases with increasing temperature and decreasing total monomer concentration since the extent of complex formation decreases. When the alternation tendency is less than absolute because of high reaction temperature, low monomer concentration, absence of a Lewis acid, or an imbalance in the coordinating abilities of the two monomers, copolymerization proceeds simultaneously by the two mechanisms. The quantitative aspects of this situation are considered in Sec. 6-5. 6-3b-4 Q e Scheme
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Various attempts have been made to place the radical monomer reaction on a quantitative basis in terms of correlating structure with reactivity. Success in this area would give a better understanding of copolymerization behavior and allow the prediction of the monomer reactivity ratios for comonomer pairs that have not yet been copolymerized. A useful correlation is the Q e scheme of Alfrey and Price [1947], who proposed that the rate constant for a radical monomer reaction, for example, for the reaction of M1 radical with M2 monomer, be written as
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where P1 represents the intrinsic reactivity of M1 radical, Q2 represents the intrinsic reactivity of M2 monomer, e1 represents the polarity of M1 radical, and e2 represents the polarity