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(CH3)3C + + CH3
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The evidence for this mechanism is based on mass spectroscopy of the gas-phase radiolysis of isobutylene, which may not be applicable to the typical liquid-phase polymerization system. Initiation in condensed systems may follow the same course as electroinitiation coupling of radical cations to form dicarbocations.
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Cationic polymerization initiated by ionizing radiation is markedly different from other cationic polymerizations in that the propagating species is a free ion remote from a counterion. Overall electrical neutrality is maintained by electrons trapped by the monomer.
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The initiator ion pair (consisting of the carbocation and its negative counterion) produced in the initiation step (Eq. 5-4) proceeds to propagate by successive additions of monomer molecules
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H CH2C(CH3)2 + (BF3OH) + (CH3)2C CH2 n H CH2C(CH3)2
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+ HMn (IZ) + M
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This addition proceeds by insertion of monomer between the carbocation and its negative counterion. The propagation reaction can be complicated in some cases by the occurrence of intramolecular rearrangements due to 1,2-hydride ion (H: ) or 1,2-methide (CH3 : ) shifts. Polymerizations proceeding with rearrangement are referred to as isomerization polymerizations. The extent of rearrangement during cationic propagation will depend on the relative stabilities of the propagating and rearranged carbocations and the relative rates of propagation and rearrangement. Both factors favor propagation without rearrangement for monomers such as styrene, indene, acenaphthylene, coumarone, vinyl ethers, and isobutylene. Not only do these
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O Coumarone Indene
monomers propagate via reasonably stable carbocations such as tertiary, benzyl, and oxycarbocations; the carbocations have no routes available for rearrangement to more stable carbocations. Extensive rearrangement during propagation occurs for a variety of 1-alkenes (a-ole ns) [Cesca, 1985]. Propene, 1-butene, and higher 1-alkenes yield oligomers (DP no higher than 10 20) with highly irregular structures due to various combinations of 1,2hydride and 1,2-methide shifts. For example, propene polymerization proceeds to give an extremely complicated oligomer structure with methyl, ethyl, n- and isopropyl, and other groups. (Hydride transfer to polymer is also involved; see Sec. 5-2c-3.) The propagating secondary carbocations are insuf ciently stable to propagate without extensive rearrangement. Simultaneously, only oligomers are formed since none of the rearrangement pathways are favorable for rapid propagation (relative to a variety of chain-transfer and termination reactions). Isomerization polymerizations yield high-molecular-weight products when reaction proceeds through relatively simple rearrangement routes involving stable carbocations. Thus
polymerization of 3-methyl-1-butene yields high polymer containing both the rst-formed (IXa) and rearranged (IXb) repeating units in varying amounts depending on the temperature
CH2 CH CH(CH3)2 IXa IXb CH2 CH2 C(CH3)2
[Kennedy et al., 1964]. Isomerism occurs by a 1,2-hydride shift in the rst-formed carbocation (Xa) prior to the addition of the next monomer unit. The rearranged ion (Xb) is a tertiary
H CH2 C + (CH3)2C H Xa Xb
CH2 CH2 C(CH3)2
carbocation and is more stable than the rst-formed carbocation, which is a secondary carbocation. The product contains mostly the rearranged repeating unit, but some normal propagation occurs at higher temperatures as a result of kinetic factors. The product contains about 70 and 100% of the rearranged repeating unit at polymerization temperatures of 100 and 130 C, respectively. High resolution 1 H and 13 C NMR shows that there is great complexity to the rearrangements occurring for certain monomers. Five different repeating units, derived from carbocations XI XV, are found in the polymer from 4-methyl-1-pentene [Ferraris et al., 1977; Kennedy and Johnston, 1975]. The rst-formed carbocation XI undergoes hydride shift to form carbocations XII, XIII, and XIV; XIII rearranges to XV by a methide shift. The repeating unit derived from XIV, the most stable carbocation, is present in the greatest abundance (42 51%). The other carbocations are of comparable stability, and the repeating units derived from them are found in comparable amounts.