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[2 COO ] [ COO [ COO [ COO + CO2 + ] [CO2 + COO ] COO + CO2 +
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3-76 3-77 3-78 3-79
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3-80 3-81
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Reactions 3-76 and 3-79 coupled, respectively, with Reactions 3-78 and 3-81 do not lower f but do lower f when coupled, respectively, with Reactions 3-77 and 3-80. The radicals that escape the solvent cage (Eqs. 3-78 and 3-81) then react as per Eqs. 3-71 through 3-75.
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Lowering of f by reactions analogous to Eq. 3-68 is referred to as the cage effect [Bamford, 1988; Koenig and Fischer, 1973; Martin, 1973]. It is a general phenomenon observed in almost all initiation systems. About the only exceptions are the initiation systems such as
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which do not produce radicals in pairs. However, even in some such instances the radical may be capable of reacting with a nonradical species in the solvent cage. Acetoxy radicals from acetyl peroxide undergo partial decarboxylation and radical combination within the solvent cage leads to stable products incapable of producing radicals:
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3-83b) 3-83a)
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The homolysis of AIBN occurs in a concerted process with simultaneous breakage of the two C bonds to yield nitrogen and 2-cyano-2-propyl radicals. Reaction of the radicals N with each other can occur in two ways to yield tetramethylsuccinodinitrile and dimethylN-(2-cyano-2-isopropyl)ketenimine:
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3-84b) 3-84a)
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A minor reaction of 2-cyano-2-propyl radicals is disproportionation to methacrylonitrile and isobutyronitrile [Moad et al., 1984; Starnes et al., 1984]. This presents a complication for polymerizations carried out to high conversions where the methacrylonitrile concentration is signi cant since methacrylonitrile undergoes copolymerization with many monomers. The cage effect has also been well documented as the cause of lowered f values in photoinitiation [Berner et al., 1978; Braun and Studenroth, 1979]. Benzoin photolysis yields benzaldehyde:
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O OH C C H O C + OH C H O 2 CH
The photolysis of benzildimethylketal yields benzoyl and benzylketal radicals in the primary cleavage. The latter radical undergoes decay within the cage to yield methyl benzoate and
methyl radical. Coupling of the methyl and benzoyl radicals decrease f :
O OCH3 C C OCH3 O C + O CH3 + CH3O C O C + OCH3 C OCH3 O O
C CH3 + CH3O C
The initiator ef ciency and quantum yield for initiation are generally independent of monomer concentration and of the radical coupling reactions occurring outside the solvent cage (Eqs. 3-74, 3-75). The prime reason for f < 1 is the reactions occurring within the solvent cage. Once a radical has diffused out of the solvent cage, the reaction with monomer (Eq. 3-71) occurs predominantly in preference to other reactions [Fink, 1983]. Even if Reaction 3-72 occurs this will be followed by Reaction 3-73 in preference to the two radical combination reactions (Eqs. 3-74, 3-75). The preference for initiation of polymerization arises from the much greater monomer concentrations (10 1 10 M) compared to the radical concentrations (10 7 10 9 M) that are normally present in polymerization systems. However, one can observe a variation of f with the monomer concentration at low monomer concentrations. Figure 3-3 shows this effect in the AIBN initiation of styrene polymerization. The initiator ef ciency increases very rapidly with [M] and a limiting value is quickly reached. Theoretical predictions [Koenig and Fischer, 1973] indicate that an effect of [M] on f would be expected at monomer concentrations below 10 1 10 2 M, and this is the general observation. f is affected at lower concentrations as one increases the initiation rate, since the radical radical reactions become more probable. An example is the photopolymerization of methyl methacrylate using benzoin methyl ether [Carlblom and Pappas, 1977],
Fig. 3-3 Effect of styrene concentration on the initiator ef ciency of azobisisobutyronitrile. *, * and refer to experiments with initiator concentrations of 0.20, 0.50, and 1.00 g L 1 , respectively. After Bevington [1955] (by permission of Faraday Society, and Royal Society of Chemistry, London).