IONIC CHAIN POLYMERIZATION in .NET

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IONIC CHAIN POLYMERIZATION
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stable to be very ef cient in polymerizing the less reactive monomers such as isobutylene and styrene but polymerization of the more reactive monomers (p-methoxystyrene, vinyl ethers, indene, N-vinylcarbazole) proceeds rapidly [Ledwith, 1979a,b; Rooney, 1978]. (Trityl and tropylium carbocations are suf ciently stable that their salts with stable anions such as hexa uoroantimonate, SbF , can be purchased in pure crystalline form from chemical vendors.) 6 Acylium ions (oxacarbocations) have also been used to initiate cationic polymerization [Sawamoto et al., 1977, 1978]. These can be formed in situ or separately prepared as the solid salt, which is subsequently added to the monomer solution:
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O R C F + SbF3 O
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R C +(SbF6 )
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5-6
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Many polymerizations exhibit a maximum polymerization rate at some ratio of initiator to coinitiator [Biswas and Kabir, 1978, 1978; Colclough and Dainton, 1958; Taninaka and Minoura, 1976]. The polymerization rate increases with increasing [initiator]/[coinitiator], reaches a maximum, and then either decreases or levels off. Figure 5-1 shows this behavior for the polymerization of styrene initiated by tin(IV) chloride water in carbon tetrachloride. The decrease in rate at higher initiator concentration is usually ascribed to inactivation of the coinitiator by initiator. The inactivation process in a system such as SnCl4 -H2 O may involve hydrolysis of Sn bonds to Sn Cl OH. There is experimental evidence for such reactions when comparable concentrations of coinitiator and initiator are present. However, the rate maxima as in Fig. 5-1 are observed at quite low [initiator]/[coinitiator] ratios where corresponding experimental evidence is lacking. An alternate mechanism for the behavior in Fig. 5-1 is that initiator, above a particular concentration, competes successfully with monomer for the initiator coinitiator complex (V) to yield the oxonium salt (VI), which
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SnCl4 + H2O
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SnCl4 OH2 V
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(H3O+)(SnCl4OH ) VI
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Fig. 5-1 Effect of water concentration on the SnCl4 -initiated polymerization rate of styrene in carbon tetrachloride at 25 C. Symbols * and * refer to initiator concentrations of 0.08 and 0.12 M, respectively. After Colclough and Dainton [1958] (by permission of the Faraday Society and Royal Society of Chemistry, London).
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CATIONIC POLYMERIZATION OF THE CARBON CARBON DOUBLE BOND
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is too unreactive in protonating ole ns because the basicity of the carbon carbon double bond is far less than that of water [Ledwith and Sherrington, 1974] (see also Sec. 5-2c-4). The optimum initiator to coinitiator ratio varies considerably depending on the initiator, coinitiator, monomer, solvent, and temperature, since these factors affect the balance between the competing processes of initiation and inactivation. Initiation by some organotransition metal complexes involves addition of a positive metallic site to monomer [Baird, 2000]. For example, the complex formed from cyclopentadienyltrimethyltitanium and triper uorophenyl boron initiates polymerization by the sequence
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(C5H5)(CH3)3Ti + (C6F5)3B (C5H5)(CH3)2Ti + (C 6F5)3(CH3)B
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5-3e
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(C5H5)(CH3)2TiM + (C 6F5)3(CH3)B
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5-2a-3
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Halogen
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Chlorine, bromine, and iodine act as cationogens in the presence of the more active Lewis acids such as trialkylaluminum or dialkylaluminum halide [DiMaina et al., 1977; Magagnini et al., 1977]. The initiating species is the halonium ion X present in low concentration via the equilibrium reaction between Lewis acid and halogen. Iodine is unique among the halogens in that it initiates polymerization of the more reactive monomers (styrene, vinyl ether, acenaphthylene. N-vinylcarbazole) even in the absence
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Acenaphthylene
of a Lewis acid [Johnson and Young, 1976; Sauvet and Sigwalt, 1989]. Iodine is not the actual initiator in this system. Iodine adds to the double bond to form a diiodide that eliminates hydrogen iodide. The hydrogen iodide generated by this process acts as the cationogen with iodine acting as a Lewis acid to form the initiating system. It was noted earlier (Sec. 52a-1) that hydrogen iodide is not an ef cient initiator because iodide ion is too nucleophilic. The presence of iodine activates (dissociates) the C bond suf ciently to allow propaga I tion to proceed. (See Sec. 5-2g for details of the propagation mechanism.) This initiation route is more ef ciently utilized by directly adding a mixture of hydrogen iodide and either iodine or a metal halide such as ZnX2 or SnX2 to the reaction system [Higashimura et al., 1988]. 5-2a-4 Photoinitiation by Onium Salts
Aryldiazonium (ArN Z ), diaryliodonium (Ar2 I Z ), and triarylsulfonium (Ar3 S Z ) 2 salts, where Z is a nonnucleophilic and photostable anion such as tetra uoroborate (BF ), hexa uoroantimonate (SbF ), and tetraper uorophenylborate [(C6 F5 )4 B ], and 4 6