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  • 1
    Electronic Resource
    Electronic Resource
    Selective vinyl cationic polymerization of monomers with two cationically polymerizable groups. II. p-vinylphenyl glycidyl ether: An epoxy-functionalized styreneFor Part I see Ref. 1. (1987)
    Bognor Regis [u.a.] : Wiley-Blackwell
    Journal of Polymer Science Part A: Polymer Chemistry 25 (1987), S. 2827-2838 
    Details
    ISSN: 0887-624X
    Keywords: Chemistry ; Polymer and Materials Science
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: p-Vinylphenyl glycidyl ether (VPGE), a styrene derivative with an epoxy pendant, was polymerized by various cationic initiators, and its selective vinyl polymerization was investigated at low temperatures below -15°C. BF3OEt2 (a metal halide) and CF3SO3H (a strong protonic acid) polymerized both vinyl and epoxy groups of VPGE, and produced cross-linked insoluble polymers. The HI/I2 initiating system and iodine, in contrast, polymerized its vinyl group in polar solvents (CH2Cl2 and nitroethane) highly selectively in the temperature range of -15 to -40°C to give soluble polymers with a polystyrene backbone and epoxy pendants; however, under these conditions, 10-15% of the epoxy groups of the polymers were consumed during the polymerization by the reaction with the growing species. The polymerization by HI/I2 in CH2CI2 involved a long-lived propagating species, as indicated by a progressive increase in the molecular weight (M̄n) of the polymers with monomer conversion and their fairly narrow molecular weight distributions (M̄w/M̄n ∼ 1.6). The differences between the polymerizations of VPGE and p-isopropenylphenyl glycidyl ether, an α-methylstyrene-type counterpart of VPGE, were also discussed with an emphasis on the effects of the α-methyl group in the latter monomer.
    Additional Material: 5 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/pola.1987.080251018
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  • 2
    Electronic Resource
    Electronic Resource
    Selective vinyl cationic polymerization of monomers with two cationically polymerizable groups. III. 2-vinyloxyethyl glycidyl ether: An epoxy-functionalized vinyl etherFor part II, see Ref. 2. (1987)
    Bognor Regis [u.a.] : Wiley-Blackwell
    Journal of Polymer Science Part A: Polymer Chemistry 25 (1987), S. 2717-2727 
    Details
    ISSN: 0887-624X
    Keywords: Chemistry ; Polymer and Materials Science
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Cationic polymerization of 2-vinyloxyethyl glycidyl ether (VEGE), a vinyl ether with an epoxy group, was conducted with various initiators in CH2Cl2 in the temperature range from +15 to -78°C, and the possibility of its selective vinyl polymerization was investigated. BF3OEt2 polymerized both vinyl and epoxy groups of VEGE to yield polymers partially insoluble in organic solvents. HI/I2, iodine, and CF3SO3H gave soluble, low-molecular-weight oligomers with epoxy pendants. 1H-NMR structural analysis of the oligomeric products showed that the epoxy/vinyl ratio of the pendants decreases in the order: 100% epoxy ∼ CF3SO3H 〉 HI/I2 ∼ I2 ≫ BF3OEt2. Although HI/I2 or iodine mainly polymerized the vinyl group, the reaction of the vinyl ether-type growing end with an epoxy group of VEGE took place during the polymerization, so that the monomer conversion leveled off at about 40%.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/pola.1987.080251008
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  • 3
    Electronic Resource
    Electronic Resource
    End-Functionalized polymers by living cationic polymerization. IV. Poly(vinyl ethers) with acidic or basic terminal groups by functional initiator method (1990)
    Bognor Regis [u.a.] : Wiley-Blackwell
    Journal of Polymer Science Part A: Polymer Chemistry 28 (1990), S. 1137-1148 
    Details
    ISSN: 0887-624X
    Keywords: Chemistry ; Polymer and Materials Science
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Carboxylic acid or primary amine-terminated poly(isobutyl vinyl ethers) were synthesized by living cationic polymerizations with functionalized initiators (CH3CHIO—CH2CH2 — X; X: that are the adducts of the corresponding vinyl ethers (CH2 = CH — OCH2CH2—X) with hydrogen iodide. In the presence of iodine, these initiators induced living cationic polymerization of isobutyl vinyl ether to give polymers with the α-end group of X originating from the initiators. The polymer molecular weights were regulated by the monomer to initiator feed ratio and the molecular weight distributions were very narrow (Mw/Mn ≤ 1.15). Subsequent deprotection of the terminal group X led to polymers with a terminal carboxylic acid or primary amine. 1H- and 13C-NMR analyses showed that the end functionalities of these polymers were all close to unity.
    Additional Material: 6 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/pola.1990.080280514
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  • 4
    Electronic Resource
    Electronic Resource
    Living cationic polymerization of ethyl 2-(vinyloxy)ethoxyacetate: A vinyl ether with an ether and an ester function in the pendant (1989)
    Bognor Regis [u.a.] : Wiley-Blackwell
    Journal of Polymer Science Part A: Polymer Chemistry 27 (1989), S. 3303-3314 
    Details
    ISSN: 0887-624X
    Keywords: Chemistry ; Polymer and Materials Science
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Ethyl 2-(vinyloxy)ethoxyacetate (4; CH2=CH—OCH2CH2OCH2—COOC2H5), a vinyl ether having both carboxylic acid ester and oxyethylene unit in its pendant, afforded well-defined living polymers when polymerized by the hydrogen iodide/iodine (HI/I2) initiating system in toluene at -40°C. The polymers possessed a narrow molecular weight distribution (Mw/Mn ≤ 1.15), and their molecular weight (Mn) increased proportionally to monomer conversion or the molar ratio of the monomer to hydrogen iodide. The polymer molecular weight also increased upon addition of a fresh feed of the monomer to a completely polymerized reaction mixture. Polymers of high molecular weights (Mn 〉 5 × 105) and broad molecular weight distributions were obtained by BF3OEt2 in toluene at -40°C. Polymerization rate of 4 with HI/I2 is ca. 100 times greater than that of the corresponding alkyl vinyl ether, and thus 4 was found to be one of the most reactive vinyl ethers thus far studied. Alkaline hydrolysis of the pendant ester groups of the polymers gave a vinyl ether-based polymeric carboxylic acid 6 with a narrow molecular weight distribution.
    Additional Material: 6 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/pola.1989.080271010
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  • 5
    Electronic Resource
    Electronic Resource
    Living cationic polymerization of vinyl ethers with carboxylic acid/tin tetrahalide initiating systems. I. New initiating systems based on acetic acid and selection of Lewis acid and basic additive leading to living polymers with low polydispersity (1998)
    Bognor Regis [u.a.] : Wiley-Blackwell
    Journal of Polymer Science Part A: Polymer Chemistry 36 (1998), S. 3173-3185 
    Details
    ISSN: 0887-624X
    Keywords: cationic polymerization ; living polymerization ; vinyl ether ; initiator ; acetic acid ; tin tetrabromide ; Chemistry ; Polymer and Materials Science
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Cationic polymerization of isobutyl vinyl ether (IBVE) with acetic acid (CH3COOH)/tin tetrahalide (SnX4: X = Cl, Br, I) initiating systems in toluene solvent at 0°C was investigated, and the reaction conditions for living polymerization of IBVE with the new initiating systems were established. Among these tin tetrahalides, SnBr4 was found to be the most suitable Lewis acid to obtain living poly(IBVE) with a narrow molecular weight distribution (MWD). The polymerization with the CH3COOH/SnBr4 system, however, was accompanied with the formation of a small amount of another polymer fraction of very broad MWD, probably due to the occurrence of an uncontrolled initiation by SnBr4 coupled with protonic impurity. Addition of 1,4-dioxane (1-1.25 vol %) or 2,6-di-tert-butylpyridine (0.1-0.6mM) to the polymerization mixture completely eliminated the uncontrolled polymer to give only the living polymer with very narrow MWD (Mw/Mn ≤ 1.1; Mw, weight-average molecular weight; Mn, number-average molecular weight). The Mn of the polymers increased in direct proportion to monomer conversion, continued to increase upon sequential addition of a fresh monomer feed, and was in good agreement with the calculated values assuming that one CH3COOH molecule formed one polymer chain. Along with these results, kinetic study and direct 1H-NMR observation of the living polymerization indicated that CH3COOH and SnBr4 act as so-called “initiator” and “activator”, respectively, and the living polymerization proceeds via an activation of the acetate dormant species. The basic additives such as 1,4-dioxane and 2,6-di-tert-butylpyridine would serve mainly as a “suppressor” of the uncontrolled initiation by SnBr4. The polymers produced after quenching the living polymerization with methanol possessed the acetate dormant terminal and they induced living polymerization of IBVE in conjunction with SnBr4 in the presence of 1,4-dioxane. © 1998 John Wiley & Sons, Inc. J Polym Sci A: Polym Chem 36: 3173-3185, 1998
    Additional Material: 12 Ill.
    Type of Medium: Electronic Resource
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  • 6
    Electronic Resource
    Electronic Resource
    Gel formation in cationic polymerization of divinyl ethers. I. 1,4-Bis(2-vinyloxyethoxy)benzene (1998)
    Bognor Regis [u.a.] : Wiley-Blackwell
    Journal of Polymer Science Part A: Polymer Chemistry 36 (1998), S. 675-683 
    Details
    ISSN: 0887-624X
    Keywords: cationic polymerization ; vinyl ether ; divinyl ether ; crosslinking ; gelation ; Chemistry ; Polymer and Materials Science
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Polymerization of 1,4-bis(2-vinyloxyethoxy)benzene (CH2=C—O—CH2—CH2—O—C6H4—O—CH2CH2—O—C=CH2; 1) was investigated in CH2Cl2 at 0°C with the use of a variety of cationic initiators. SnCl4, SnBr4, AlEtCl2, and BF3OEt2 (strong Lewis acids) and CF3SO3H (a strong protonic acid) yielded crosslinked insoluble polymers immediately after the polymerizations were initiated. The binary initiating systems such as HCl/ZnCl2 and (C6H5O)2P(O)OH/ZnCl2 also produced insoluble poly(1)s. At the low initial concentration of ZnCl2, however, the (C6H5O)2P(O)OH/ZnCl2 system gave the soluble polymers quantitatively, and gelation occurred only when the reaction mixture was stored for a long time after complete consumption of the monomer. The content of the unreacted pendant vinyl ether groups of the soluble polymers decreased with monomer conversion, and almost all the pendant vinyl ether groups were consumed in the soluble polymer obtained at 100% monomer conversion; this may be ascribed to frequent occurrence of intramolecular crosslinking. © 1998 John Wiley & Sons, Inc. J Polym Sci A: Polym Chem 36: 675-683, 1998
    Additional Material: 10 Ill.
    Type of Medium: Electronic Resource
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  • 7
    Electronic Resource
    Electronic Resource
    Photochromic and photomechanical ionene elastomer containing poly(tetrahydrofuran) segments and viologen units (1991)
    Bognor Regis [u.a.] : Wiley-Blackwell
    Journal of Polymer Science Part A: Polymer Chemistry 29 (1991), S. 651-655 
    Details
    ISSN: 0887-624X
    Keywords: Chemistry ; Polymer and Materials Science
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Elastomeric polymer consisting of poly(oxytetramethylene) segments and viologen units (PTV) was synthesized by the reaction of dicationic living poly(tetrahydrofuran) with 4,4′-bipyridine at -70°C. The chloride or bromide ion was introduced as the counter anion into the viologen groups of PTV by the treatment of the reaction mixture with aqueous sodium chloride or bromide, respectively. The solid film of PTV having chloride inon showed photochromism, i.e., color change by light irradiation, via photoreduction of the violegen groups. In contrast. PTV of bromide counter anion required a small amount of poly(N-vinyl-2-pyrrolidone) to undergo the photochromic reaction. The irradiation of light also affected the stress relaxation of the polymers, namely PTV showed photomechanical behavior. This phenomenon is considered to be induced by the decrease of total number of ionic charges of PTV by photo-reduction of the viologen groups followed by the change of a state of ionic clustering in the polymer matrix.
    Additional Material: 5 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/pola.1991.080290506
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  • 8
    Electronic Resource
    Electronic Resource
    Selective vinyl cationic polymerization of monomers with two cationically polymerizable groups. I. p-isopropenylphenyl glycidyl ether: An epoxy-functionalized α-methylstyrene (1987)
    Bognor Regis [u.a.] : Wiley-Blackwell
    Journal of Polymer Science Part A: Polymer Chemistry 25 (1987), S. 1073-1084 
    Details
    ISSN: 0887-624X
    Keywords: Chemistry ; Polymer and Materials Science
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: p-Isopropenylphenyl glycidyl ether (IPGE), a monomer of dual cationic functionality (isopropenyl and epoxy), was polymerized by a variety of initiators, and optimum conditions were established for its selective vinyl cationic polymerization. The hydrogen iodide/iodine (HI/I2) initiating system or iodine polymerized selectively the isopropenyl group in CH2Cl2 at a low temperature (-78°C), to produce soluble poly(IPGE) with epoxy pendants. Under these conditions, the number-average molecular weight of the polymers was inversely proportional to the initial initiator concentration, indicating the formation of long-lived propagating species. Soluble poly(IPGE) was also obtained at -15 and -40°C by HI/I2 or iodine. However, at these higher temperatures, transfer and/or termination reactions took place to give olefin-terminated polymers, in which some of the pendant epoxy groups were consumed. BF3OEt2 (a metal halide) and CF3SO3H (a strong protonic acid) polymerized both epoxy and isopropenyl groups of IPGE and yielded crosslinked insoluble polymers.
    Additional Material: 4 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/pola.1987.080250413
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  • 9
    Electronic Resource
    Electronic Resource
    Living cationic polymerization of 2-vinyloxyethyl phthalimide: Synthesis of poly(vinyl ether) with pendant primary amino functions (1988)
    Bognor Regis [u.a.] : Wiley-Blackwell
    Journal of Polymer Science Part A: Polymer Chemistry 26 (1988), S. 3361-3374 
    Details
    ISSN: 0887-624X
    Keywords: Chemistry ; Polymer and Materials Science
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Cationic polymerization of 2-vinyloxyethyl phthalimide (1) in CH2Cl2 at -15°C with hydrogen iodide/iodine (HI/I2) as initiator led to living polymers of a narrow molecular weight distribution (M̄w/M̄n = 1.1-1.25). The number-average molecular weight of the polymers was in direct proportion to monomer conversion and could be controlled in the range of 1000-6000 by regulating the 1/HI feed ratio. However, when a fresh monomer was supplied to the completely polymerized reaction mixture, the molecular weight of the polymers was not directly proportional to monomer conversion. The polymerization of 1 by boron trifluoride etherate (BF3OEt2) in CH2Cl2 at -78°C gave polymers with relatively high molecular weight (M̄w 〉 20,000) and broad molecular weight distribution (M̄w/M̄n ∼ 2). The HI/I2-initiated polymerization of 1 was an order of magnitude slower than that of ethyl vinyl ether, probably because of the electron-withdrawing phthalimide pendant. Hydrazinolysis of the imide functions in poly(1) gave a water-soluble poly(vinyl ether) (3) with aliphatic primary amino pendants.
    Additional Material: 9 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/pola.1988.080261219
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  • 10
    Electronic Resource
    Electronic Resource
    Selective vinyl cationic polymerization of monomers with two cationically polymerizable groups. IV. New initiating systems for selective and living polymerization of p-isopropenylphenyl glycidyl etherFor Part III, see Ref. 4. (1991)
    Bognor Regis [u.a.] : Wiley-Blackwell
    Journal of Polymer Science Part A: Polymer Chemistry 29 (1991), S. 339-346 
    Details
    ISSN: 0887-624X
    Keywords: Chemistry ; Polymer and Materials Science
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: A variety of cationic initiators were employed for p-isopropenylphenyl glycidyl ether (IPGE), an α-methylstyrene derivative with an epoxy pendant, and optimum initiators and reaction conditions were evaluated in terms of its selective vinyl polymerization and living polymerization. Despite the coexistence of two cationically polymerizable groups in IPGE, binary initiating systems (HI, CF3COOH, or CH3CH(OiBu)-OCOCH3, each coupled with ZnI2) and sulfonic acids (CF3SO3H and CH3SO3H) selectively polymerized the vinyl group of IPGE in CH2Cl2 at -78°C to produce soluble polymers with epoxy pendant groups in high yield. Metal halides (BF3OEt2 and AlEtCl2) polymerized both the vinyl and epoxy groups of IPGE to give crosslinked insoluble polymers. In contrast, under these conditions, the HI/ZnI2 system also led to a long-lived polymer, the molecular weight of which increased upon addition of a fresh feed of monomer to a completely polymerized reaction mixture, whereas the use of other initiators resulted in nonliving polymers. At higher temperatures (-40 and -15°C), soluble poly(IPGE) was also obtained with HI/ZnI2, but the polymer yield decreased with raising temperature, because of the occurrence of termination reaction.
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/pola.1991.080290306
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