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Salts in Aromatic Solvents Polymer Journal, Vol. 7, No. 3, pp 366-371 (1975) Photoreactions of N-Vinylcarbazole Induced by Metal Salts. V. Mechanistic Studies of the Cationic Polymerization Induced by Silver(I) Salts in Aromatic Solvents Yoshihiko TAKEDA,* Michihiko AsAr,** and Shigeo TAZUKE*** Department of Polymer Chemistry, Kyoto University, Kyoto 606, Japan. (Received October 9, 1974) ABSTRACT: Photosensitized cationic polymerizations of N-vinylcarbazole (VCZ) in­ duced by silver(!) perchlorate and tetrafluoroborate in various aromatic solvents were investigated under irradiation at 365 nm at 30°C. The polymerization rates decreased in the following order: nitrobenzene> benzene> toluene The specific in­ teraction between VCZ and silver which was observed spectroscopically only in the perchlorate-benzene system does not participate in the initiation processes. It was concluded that the effective absorption species leading to initiation is VCZ itself. Arguing from the kinetic behavior and the similarity in molecular weights of the poly­ mers, the polymerization in benzene and toluene proceeded via an identical mechanism. The poor photochemical reactivity in p-xylene was assumed to be attributable to the initial processes. Moreover, excitation of the charge-transfer band of the VCZ-nitroben­ zene complex in the presence of silver perchlorate enhanced the polymerization rate in comparison to the photopolymerization without silver perchlorate. The following initia­ tion mechanism was proposed: The electron transfer from excited VCZ* to solvent molecule produces a cation radical, vcz+, which in turn reacts with AgCI04 to pro­ duce the initiating species. KEY WORDS N-Vinylcarbazole I Cationic Polymerization I Silver(!) Salts I Photopolymerization I Charge Transfer Polymerization I In the preceding paper/ kinetic features of (p-Xy), and nitrobenzene (NB) as well as Bz, the photosensitized cationic polymerization of using silver(!) tetrafluoroborate and tetra-n­ N-vinylcarbazole (VCZ) induced by silver(!) butylammonium perchlorate, as well as silver perchlorate in benzene (Bz) were investigated perchlorate, as catalysts. The molecular interac­ under irradiation at 365 nm at 30°C. The pre­ tion between VCZ and silver salt in the ground sent article describes the mechanistic studies of state was measured by absorption spectroscopy. the initiation processes; here two sorts of pro­ From these results, a possible mechanism of blems are examined: What is the effective light initiation was proposed. Kinetic data obtained absorbing species leading to initiation? And previously were interpreted in accordance with what is the role of silver(!) salt-silver cation this mechanism. or counter anion? To elucidate these problems, photopolymerizations were carried out in various EXPERIMENTAL aromatic solvents such as toluene (Tol), p-xylene N- Vinylcarbazole, silver(!) perchlorate, and * Present address: Mitsubishi Monsanto Co., Ltd., benzene were purified as described in the pre­ Yokkaichi, Mie 510. ceding article. 1 Toluene and p-xylene were ** Present address: Research Institute for Polymers purified by methods similar to that used for and Textiles, Sawatari 4, Kanagawa-ku, Yokohama, Kanagawa 221. To whom correspondence should benzene. Nitrobenzene was purified as reported be addressed. previously. 2 Silver( I) tetrafluoroborate was *** Present address: Research Laboratory of Re­ dried in vacuo for more than 10 hr at room sources Utilization, Tokyo Institute of Technology, temperature before use. Tetra-n-butylammonium Meguro-ku, Tokyo 152. perchlorate was prepared and purified using the 366 Photopolymerization of N-Vinylcarbazole: Mechanisms procedures reported by Fujinaga, et al. 3 All 100r----------------. other experimental methods were the same as described in the preceding article. RESULTS AND DISCUSSION Photopolymerization in Benzene As shown in the preceding paper/ the photo­ ..., 60 sensitized cationic polymerization of N-vinyl­ Ql u carbazole (VCZ) in the presence of silver(!) c: ..... perchlorate was induced under irradiation at ......"' 30°C in benzene, whereas thermal as well as E 40 "'c: noncatalytic photosensitized polymerization were ... 1-"' negligibly slow. The problem of the photo­ absorbing species is not straightforward, just as 20 encountered in the photopolymerization system sensitized by tetrahaloaurate(III) in nitroben­ zene. 4 Under the polymerization condition ([VCZ] 0 =0.25M) no change in absorption spectra 310 330 350 (Figure 1) was observed by the addition of Wavelength (nm) silver(!) perchlorate up to 2 x 10-4M. However, in absorption spectroscopy in the short wave­ Figure 2. Absorption spectra of relevant com­ length region under very dilute conditions, com­ pounds in benzene: I, benzene; 2, [AgCI04], I0-4M; 3, [VCZ]o, I0-4M; 4, [VCZ]o, IQ-4M, plex formation between VCZ and silver perchlo­ [AgCI04]o, I0-5M; room temperature, rate was observed, as shown in Figure 2. Therefore, the photoabsorbing species effective for the initiation is either VCZ itself or some Table I. Effect of (n-C4H9)4NCI04 (TBP) on the photopolymerization• kind of VCZ-AgC104 complex. Reference experiments using tetra-n-butyl­ TBP, M [VCZ]o, M Time, min Conv.,% ammonium perchlorate were performed as shown I X I0-2 0.25 120 in Table I. Since the complete inertness of the 5 0 0.25 120 7 1 00 .----------, • Under irradiation of unfiltered light, 30°C. ;;:; 80 perchlorate anion as photosensitizer was proved, the active part of silver perchlorate must be Q) u c: Ag(I) itself and not the perchlorate anion. Also, .....ItS 60 silver(!) tetrafluoroborate as sensitizer was effec­ ..... e tive for the photopolymerization, although its c: activity was a little less than that of AgC104 , "'ItS 40 .....s.. as shown in Figure 3, indicating that the role of the anion is minor. However, the blue shift 20 in absorption spectra attributed to the complex formation observed in the VCZ-AgCl04 system was not detected in the VCZ-AgBF4 system. 365 370 The total amount of VCZ-AgC104 complex Wavelength (nm) is negligibly small in comparison with the free Figure 1. Absorption spectrum of the polymeriza­ VCZ under the present experimental conditions 4 tion system: [VCZ]o, 0.25M; [AgC104]0 , 1 X I0-4M; for polymerization ([Ag(I)]=l0- M, [VCZ]= room temperature, solvent, benzene. O.lM) even if the complex formation is nearly Polymer J., Vol. 7, No. 3, 1975 367 Y. TAKEDA, M. ASAI, and S. TAZUKE 7 6 5 i. t c c 4 0 g Ill Q; > 5 <1> 3 c > 0 c u 0 u 2 0 50 100 150 0 40 80 120 160 time (min) time (min) Figure 4. Photopolymerizations catalyzed by Figure 3. Photopolymerizations catalyzed by AgCl04 in various aromatic solvents: [VCZ]o, AgCI04 and AgBF4 in benzene: [VCZ]o, 0.5M; 0.25M; [AgC104]o, 1 x 10-4M; )., 365 nm; 30°C: )., 365 nm; 30°C: -e-, [AgCI04]o, 1 x I0-4M; -0-, benzene; -e-, toluene; -0-, p-xylene; -0-, [AgBF4], 2x I0-4M. -•-, nitrobenzene. completed. Furthermore, the blue shift of the Table II. Thermal polymerization initiated absorption band of VCZ is brought about as a by AgCl04 in various solvents result of the complexation. 6 Consequently, the photoenergy at 365 nm is absorbed exclusively Solvent [VCZ]o, [AgC104]o, Temp, Rp, M M oc M/min by VCZ itself. The relation Rpw/0 o.s [ AgBF4]0 , 5 similar to the AgC104-Bz system/ was obtained. Benzene 0.25 1 X J0-4 30 3. 7 X J0- 1 X 10-4 X 5 Polymerization Induced by Silver(!) Perchlorate Toluene 0.25 30 3.1 J0- p-Xylene 0.25 1 X 10-4 30 2.9 X J0-5 in Several Aromatic Solvents (Figure 4) Nitro- 0.225 1 X 10-4 30 6.5 X J0-5 In toluene, which is chemically close to ben­ benzene zene, photopolymerization proceeded with a somewhat slower rate than in benzene; the 0.4 formation of VCZ-AgC104 complex was not observed, indicating light absorption by VCZ alone. Both thermal and noncatalyzed photo­ polymerizations were also negligibly slow. The d 0.2 kinetic investigation leads to the rate expression: a: 5 Rpw/0°" [AgC104]0 , which is again similar to 2'" that for the AgCl04-Bz system. 1 In contrast ' to benzene and toluene, however, photoirradia­ tion of the reaction mixture in p-xylene was almost ineffective, whereas thermal and non­ 0 0.2 0.4 0.6 catalyzed photopolymerizations proceed with a -log 10 (arb.) rate comparable to other solvent systems. The Figure 5. Dependence of Rp on lo in nitrobenzene: absorbance of the polymerization solution was [VCZ]o, 0.25M; [AgC104]o, 1 X I0-4M: -e-, )., nearly identical for 'AgC104-Bz, AgC104-Tol, 365 nm, 1ZOC; -0-, )., 436 nm, 23°C. AgBF4-Bz, and AgClO.-p-Xy systems. Con­ sequently, the marked differences in Rp in these styrene derivatives in benzene, toluene, or p­ systems must be attributed either to the efficiency xylene proceeds with almost identical rates/ and of initiation or to the propagation andjor ter­ in addition, the slow dark cationic polymeriza­ mination processes. The latter possibility is tion of VCZ by silver perchlorate was hardly precluded since the cationic polymerization of affected by the kind of solvent (Table II). 368 Polymer J., Vol. 7, No. 3, 1975 Photopolymerization of N-Vinylcarbazole: Mechanisms Table III. Photopolymerizations of VCZ catalyzed by silver(I) salts under irradiation at 365 nm Ag(l) salt [Ag(l)]o, M [VCZ]o, M Temp, oc Solvent UV spectra X y AgC104 0.3-2x 104 0.25 30 Benzene 1/2 Blue shift AgC104 0.5-5x 104 0.5 30 Toluene 1/2 No shift AgC104 1 X 104 0.5 30 p-Xylene No polymerization No shift AgC104 0.5-2x 104 0.25 23 Nitrobenzene 1/2 0 AgBF4 1 -5x 104 0.5 30 Benzene 1/2 No shift In nitrobenzene, another type of aromatic Table IV. Degree of polymerization for solvent, a rapid photopolymerization resulted photopolymerization in various solvent under irradiations at 365 nm and 436 nm, al­ Solvent [VCZ]o, M [AgC104]o, M F though the problem of absorption species was considerably different from the above systems; Toluene 0.5 1 X J0-4 4.4xl02 this will be discussed later.
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