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which follows the order of their electron-donating effect as indicated by the sigma values shown in parentheses. Log 1=r1 for meta- and para-substituted styrenes has also been correlated with the 13C NMR chemical shifts of the b-carbon of the substituted styrenes [Hatada et al., 1977, 2002; Wood et al., 1989]. Similar correlations have been observed for the cationic copolymerizations of para-substituted benzyl vinyl ethers with benzyl vinyl ether. The correlation of log 1=r1 with chemical shift (d) is analogous to the correlation with s, since both d and s measure the electron-donating ability of the substituent.

,Bl(k, k')



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TABLE 6-9 Steric Effects in Cationic Copolymerization of a- and b-Methylstyrenes (M1) with p-Chlorostyrene (M2)a,b M1 Styrene a-Methylstyrene trans-b-Methylstyrene cis-b-Methylstyrene

3 4 1

r1 2.31 9.44 0.32 0.32

[a(k), bt(k')]

r2 0.21 0.11 0.74 1.0

+ i8 '

Although the Hammett-type approach is most useful for the quantitative correlation of monomer reactivity with structure, it is applicable only to substituted styrenes. One is, however, usually more interested in the relative reactivities of the commonly encountered monomers such as isoprene, acrylonitrile, and isobutylene. The appropriate quantitative data are relatively sparse for these monomers. The generally observed order of monomer reactivity is

(9.42)





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which is the order expected on the basis of the electron-donating ability of the various substituents. Monomers with electron-withdrawing substituents such as acrylonitrile, methyl methacrylate, and vinyl chloride show negligible reactivity in cationic copolymerization. There has been some success in correlating log 1=r1 with the e values from the Q e scheme [Ham, 1977]. Steric effects similar to those in radical copolymerization are also operative in cationic copolymerizations. Table 6-9 shows the effect of methyl substituents in the a- and bpositions of styrene. Reactivity is increased by the a-methyl substituent because of its electrondonating power. The decreased reactivity of b-methylstyrene relative to styrene indicates that the steric effect of the b-substituent outweighs its polar effect of increasing the electron density on the double bond. Furthermore, the trans-b-methylstyrene appears to be more reactive than the cis isomer, although the difference is much less than in radical copolymerization (Sec. 6-3b-2). It is worth noting that 1,2-disubstituted alkenes have nite r values in cationic copolymerization compared to the values of zero in radical copolymerization (Table 6-2). There is a tendency for 1,2-disubstituted alkenes to self-propagate in cationic copolymerization, although this tendency is low in the radical reaction.

~(k, k') = [b(k'), a(k)]

6-4a-2

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= 7r

It has previously been shown that large changes can occur in the rate of a cationic polymerization by using a different solvent and/or different counterion (Sec. 5-2f). The monomer reactivity ratios are also affected by changes in the solvent or counterion. The effects are often complex and dif cult to predict since changes in solvent or counterion often result in alterations in the relative amounts of the different types of propagating centers (free ion, ion pair, covalent), each of which may be differently affected by solvent. As many systems do not show an effect as do show an effect of solvent or counterion on r values [Kennedy and Marechal, 1983]. The dramatic effect that solvents can have on monomer reactivity ratios is illustrated by the data in Table 6 10 for isobutylene-p-chlorostyrene. The aluminum bromide-initiated copolymerization shows r1 1:01, r2 1:02 in n-hexane but

(9.43)

TABLE 6-10 Effect of Solvent and Initiator on r Values in Cationic Copolymerization r1 Isobutylene 1.01 14.7 8.6

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11 Perfect here is used just to indicate that these are the modes obtained when the semitransparent mirror is regarded as if it were a perfectly reflecting mirror.

Solvent n-C6H14 (E 1.8) f-NO2 (E 36) f-NO2 (E 36)

r1 14:7, r2 0:15 in nitrobenzene The variation in r values has been attributed to the preferential solvation of propagating centers in the nonpolar medium (n-hexane) by the more polar monomer (p-chlorostyrene) The increased local concentration of p-chlorostyrene at the reaction site results in its greater incorporation into the copolymer than expected, based on the composition of the comonomer feed in the bulk solution Calculation of r values using the bulk comonomer feed composition results in a lower value of r1 coupled with a higher value of r2 In the polar nitrobenzene the propagating centers are completely solvated by the solvent without participation by p-chlorostyrene, and the more reactive isobutylene exhibits its greater reactivity The effect of solvent on monomer reactivity ratios cannot be considered independent of the counterion employed.

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