IONIC CHAIN POLYMERIZATION in .NET

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IONIC CHAIN POLYMERIZATION
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hexa uorophosphate (PF ), are effective photoinitiators of cationic polymerization [Crivello, 6 1999; Crivello et al., 1999; Crivello and Sangermano, 2001; Decker et al., 2001]. Aryldiazonium salts have limited practical utility because of their inherent thermal instability. Diaryliodonium and triarylsulfonium salts are very stable so stable that their mixtures with highly reactive monomers do not undergo polymerization on long-term storage. Some of these initiators have found commerical application in the photocrosslinking of epoxy resins through cationic polymerization. Diaryliodonium and triarylsulfonium salts act as photoinitiators of cationic polymerization. Photolytic celeavage of an Ar or Ar bond yields a radical cation (Eq. 5-8) that I S reacts with HY to yield an initiator coinitiator complex that acts as a proton donor to initiate
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cationic polymerization. HY may be solvent or some other deliberately added substance such as an alcohol (or adventitious impurity, including water) with a labile hydrogen. Overall, the process is a photolytically induced redox reaction between the cation radical and HY. Interestingly, the same result has been achieved thermally without photolysis by coupling the appropriate reducing agent (e.g., ascorbic acid or copper(I) benzoate) with a diaryliodonium salt [Crivello et al., 1983]. The spectral response (absorption wavelength, absorption coef cient, quantum yield, photosensitivity) and thermal stability of the onium salt photoinitiators can be altered by modifying the structure of the aromatic groups in the cation portion. The choice of anion in the onium salt alters its behavior in polymerization by altering the identity of the initiating species. Cationic photoinitiators are used in coatings, printing inks, adhesives, sealants, and photoresist applications. Most of the applications involve vinyl ether polymerizations or ringopening polymerizations of epoxy monomers (Sec. 7-2b). Quantitative aspects of photopolymerization have been described in Sec. 3-4c. There are some differences between radical and cationic photopolymerizations. The dependence of Rp on light intensity is half-order for radical polymerization, but rst-order for cationic polymerization. Radical photopolymerizations stop immediately on cessation of irradiation. Most cationic photopolymerizations, once initiated, continue in the absence of light because most of the reaction systems chosen are living polymerizations (Sec. 5-2g). 5-2a-5 Electroinitiation
Electrolytic or electroinitiated polymerization involves initiation by cations formed via electrolysis of some component of the reaction system (monomer, solvent, electrolyte, or other deliberately added substance) [Cerrai et al., 1976, 1979; Funt et al., 1976; Oberrauch et al.,
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CATIONIC POLYMERIZATION OF THE CARBON CARBON DOUBLE BOND
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1978; Olaj, 1987]. Thus initiation in the presence of perchlorate ion proceeds by oxidation of perchlorate followed by hydrogen abstraction
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where HY is some hydrogen donor in the system. Perchloric acid is the actual initiating species. Some electroinitiated polymerizations proceed via monomer radical cations (VII) formed by electron transfer
CH OR
+ CH2 CH OR VII
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5-11
from monomer either to the anode or to a polynuclear aromatic compound. Propagation is proposed to proceed via the dicarbocation VIII formed by dimerization of VII. 5-2a-6 Ionizing Radiation
Ionizing radiations (Sec. 3-4d) initiate cationic polymerization [Def eux et al., 1983; Plesch, 1993; Stannett, 1989]. The rst event is the formation of a radical cation such as VII by the ejection of a p-electron. The radical cation can react to form other radical, anionic, and cationic species (Sec. 3-4d). Whether one observes radical, cationic, or anionic polymerization depends on the monomer and reaction conditions. Styrene can undergo polymerization by all three mechanisms. For superdry reaction systems at 25 C, the overwhelming mechanism for polymerization is cationic with about 2.5% anionic and negligible radical reaction. Radical polymerization becomes the dominant process with increasing reaction temperature. The presence of water or other protogens markedly decreases the extent of ionic polymerization relative to radical polymerization. Isobutylene shows negligible tendency to undergo any polymerization expect cationic, and that occurs only at lower temperatures (usually considerably below 0 C). At higher temperatures, no polymerization occurs since the cationic reaction is not favored. The actual species responsible for cationic polymerizations initiated by ionizing radiation is not established. The most frequently described mechanism postulates reaction between radical cation and monomer to form separate cationic and radical species; subsequently, the cationic species propagates rapidly while the radical species propagates very slowly. The proposed mechanism for isobutylene involves transfer of a hydrogen radical from monomer to the radical cation to form the t-butyl carbocation and an unreactive allyl-type radical: