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1 Mem. Grad. Eng. Univ. Fukui, Vol. 55 (March 2007) Cationic Polymerization of Vinyl Ethers Containing an Oxyethylene Chain and a Urethane Linkage in Their Substituents Kenta ICHIMURA* and Tamotsu HASHIMOTO* (Received January 31, 2007) 2-(2-vinyloxyethoxy)ethyl phenylcarbamate (VEEPC) and 2-[2-(2-vinyloxyethoxy)ethoxy] ethyl phenylcarbamate (VEEEPC) were synthesized by the reactions of phenyl isocyanate with di(ethylene glycol) mono vinyl ether and tri(ethylene glycol) mono vinyl ether, respectively, and were purified by molecular distillation. These new vinyl ethers with both an oxyethylene chain and a urethane group were polymerized under the various reaction conditions to investigate the possibility of their living polymerization. The HC1/ZnCl2-initiated polymerization of VEEPC proceeded in CH2C12 at -30 C, where the number-average molecular weights (Mn's) of the product polymers were in direct proportion to monomer conversion. However, the polymer molecular weight distributions (MWDs) were somewhat broad (Mw/Mn = 1.25). The polymerization of VEEEPC may involve more side reactions to produce rather low-molecular-weight products under the same reaction conditions, although the Mn's of the polymers increased with increasing monomer conversion. The thermal and other properties of the obtained polymers were also studied. Key Words : Cationic polymerization, Living polymerization, Vinyl ether, Oxyethylene, Urethane, Phenylcarbamate *Materials Science an d Engineering Course, Graduate School of Engineering
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3 k 3 a C ath----mo00 C N b\ \ II I cd e f H b CH2=CH OLIOLf\ 0 II H I cde fgh h Fig. 11 _10 C N k D" b h a ' j H2O 1,11 DMSO '0 893Pm) NMR spectra of VEEPC in 1MSO-d6: DMSO-d6: 1H NMR; (B) 13C NIVIR. NMR. d,e,f,g C h,aii 1120 DMSO (B) ch2=ch-ooo C Nk ab/ /II I h cdef 0 H b h, i, j, k a I iii 9 f (B) a b CH2=CH 0 H 0 00O C m I ViLILJN c de f g hk I j, k, I, M a f, g b r""j"-- d, e I C I DMSO 1:1,e I, a (PPrn) Fig (1)Pm) NMR spectra of VEEEPC in DMSO-d6: 11-1 NMR; (B) '3C NMR. 0 a, ppm
4 8 4 Table l Cationic Polymerization of VEEP& Initiator (mm) Solvent Temperature ( C) Time (h) mnb) m,, tm b) BF3OEt2 (5.0) CH2Cl BF3OEt2 (5.0) CH2Cl BF3OEt2 (5.0) CH3CH2NO HC1/ZnC12 (5.0/2.0) CH2C HC1/ZnCl2 (5.0/2.0) CH3CH2NO2 a) [M10 = 0.30M; conversion: 100%. b) Measured by CPC, polystyrene calibration M 10,-, 6 Cale. -'" (C) Conversion, % Mn Mw/Mr, Fig ',1:3-1.1 (B) Conversion, % MW(PSt) Polymerization of VEEPC with HCI/ZnC12 in CH2C12 at -30 C: [VEEPC]o = 0.30M; [HCl]o = 5.0mM; [ZnCl2]0 = 2.0mM. vs. conversion: by GPC(0); M by NMR( ); (B) Mw/M, vs. conversion ; (C) GPC traces of polymerization products
5 5 ka b I m CH3CI-11,C F12-CH)-C FI2-?H-O-CH3 C r-oec dc CO CO Co fl---- OCO C=0 C=0 b, c, d, e, I, H2O DMSO N-H N-H gn-h h,i jr-^-^ TA" Ohioa gafii chci31m410/ivko% i 1 I _.:',- Lb", A i acppm) Fig NMR spectrum of PolyVEEPC. (B) IH I' NMR spectrum of the lowest-molecular-weight fraction I of the product [shown in Fig.3(C)] by the polymerization of VEEPC with HC1/ZnC12 in CH2C12 at -30 C: [VEEPC]0 = 0.30M; 11-1C110 = 5.0M; iznc1210= 2.0M. (B) a 0 bh CH3 C H C N 0 d C e1c) LO h i C=0 NH g g 10 9 CHCI3 f jill, d, e, H2O L h, i, j c, r-a-1 DMSO CH2C12 I? alppm1 g CH2=CH HCI CH3-CH-CI ZnCl2 CH3-CH-Cli-ZnC12 I I OR OR OR G 0 Monomer CH3-CHiCH2-CH)-CH2-CH-Clii-ZnC12 On R OR 0 R 2 and 3 H2O CH3-CH-OH 4 OR+ HCI (and ZnCl2) CH3CHO + HOR 5 HOR(5) C1-13-CH-OR 2 and 3 I + HCI (and ZnCl2) OR 6 4HOR(5)CH3-CH-ECH2-CH)-CH2-CH-OR ORn OR OR + HCI 7 4 CH3OHCH31H-ECH2-?1-1)TCH2-CH-OCH3 (NH4OH) OR OR OR 8 Scheme 1 R = \0/III0 0 O C N Reaction mechanism of the polymerization of VEEPC and the formation of low-molecular-weight side H products with the HCI/ZnC12 initiating system.
6 20 15 r ;) 10 5 op Cale. (C) Conversion, "A.5.I.-rip ".82\---AA.1.45 ' I I I Conversion, % MW(PSt) M/m. L L I 1.45 Fig. 5 Polymerization of VEEEPC with HC1/ZnCl2 in CH2Cl2 at -30 C: [VEEEPC]o = 0.30M; [HCl]o = 5.0mM; [ZnCldo = 2.0mM. Mn vs. conversion; (13) Ajw/M, vs. conversion and (C) GPC traces of polymerization products.
7 6 o O C O 7 Table 2 Glass Transition Temperature of Polymers ( CH2 CH ) CO 0=C +CH2 CH 9 0=C CH2-CH+, CO [ 0 0=C ( ch2ch ) co 0=C H-1^I COC VEPC %IBM VEEPC %TEEM M. 19,500 21,900 16, Tg( C)a) T(1(0C)h) a) By DSC; 2nd heating scan. b) By TGDTA; 5% weight loss. Table 3 Solubility of Polymers') -CH,?H+ C: 0=? a 4, CH9H± Co CX.0 H a 4, = 670(1 Hexane Toluene.DiHlh4lChloro- Tel rahyd ro- Diehroether fora n methane form Nitro- Dirndl-0 -Prominol Acetone. ethane solfosille X X X X x x x ±CHFyH± Co O.? x x x X = ±chic0± O X X X x =y a41, = a) Polymer concentration, lwt/vol%.
8 [1] T. Higashimura, In Cationic Polymerization (in Japanese); Kagaku Dojin: Kyoto, Chapter 6 (1971). [2] J. P. Kennedy, and E. Marechal, In Carbocationic Polymerization; John Wiley & Sons: New York, Chapter 3 (1982). [3] M. Sawamoto, Prog. Polym. Sci. 16, 111 (1991). [4] T. Higashimura, S. Aoshima, and M. Sawamoto, Makromol. Chem. Macromol. Symp. 3, 99 (1986). [5] T. Namikoshi, T. Hashimoto, and T. Kodaira, J. Polym. Sci., Part A: Polym. Chem. 42, 2960 (2004). [6] T. Namikoshi, and T. Hashimoto, Mem. Grad. Eng. Univ. Fukui 54, 33 (2006). [7] S. Sugihara, K. Hashimoto, S. Okabe, M. Shibayama, S. Kanaoka, and S. Aoshima, Macromolecules 37, 336 (2004).
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