Living cationic polymerization of vinyl monomers by organoaluminum halides. 3. Living polymerization of isobutyl vinyl ether by ethyldichloroaluminum in the presence of ester additives

Aoshima, Sadahito; Higashimura, Toshinobu

doi:10.1021/ma00193a001

Cited by 251 publications

(215 citation statements)

References 2 publications

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“…To investigate the effects of the pendant structure in a monomer on cationic polymerization behavior with a baseassisting system, cationic polymerization of a series of VEs containing ether and/or ester groups was first performed with Et 1.5 AlCl 1.5 using an adduct of isobutyl VE (IBVE) with acetic acid [IBEA; CH 3 CH(OiBu)OCOCH 3 ] as an initiator in toluene at 0 C in the presence of an added base (1,4-dioxane or ethyl acetate); these represent typical reaction conditions for base-assisting living cationic polymerization of vinyl ethers with alkyl and oxyethylene groups 28,30,31 (Chart 1, Table 1). The polymerization of EOVE, EVEH, and EVH using Et 1.5 AlCl 1.5 proceeded quantitatively and yielded polymers with narrow molecular weight distributions (MWDs) despite the presence of ether and/or ester groups in their pendant structures.…”

Section: Resultsmentioning

confidence: 99%

“…26 3 ] was prepared from IBVE and acetic acid as previously reported. 28 Commercial Et 1.5 AlCl 1.5 (Nippon Aluminum Alkyls; 1.0 M solution in toluene), TiCl 4 (Aldrich; 1.0 M solution in dichloromethane), SnCl 4 (Aldrich; 1.0 M solution in heptane), and ZnCl 2 (Aldrich; 1.0 M solution in diethyl ether) were used without further purification. For FeCl 3 , stock solution in diethyl ether was prepared from anhydrous FeCl 3 (Aldrich; 99.99%).…”

Section: Methodsmentioning

confidence: 99%

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Lewis acid‐specific polymerization behaviors in living cationic polymerization of vinyl ether with a malonate group

Oda

Tsujino

Kanaoka

et al. 2012

J. Polym. Sci. A Polym. Chem.

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Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Lewis acid‐specific polymerization behaviors in living cationic polymerization of vinyl ether with a malonate group

Oda

Tsujino

Kanaoka

et al. 2012

J. Polym. Sci. A Polym. Chem.

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“…Et 1.5 AlCl 1.5 (Aldrich; 0.4 M in toluene) was used as supplied. 1-(Isobutoxy) ethyl acetate (CH 3 CH(OiBu)OCOCH 3 (IBEA)), as a cationogen, was prepared by the addition reaction of isobutyl vinyl ether and acetic acid, and then IBEA was distilled over CaH 2 under reduced pressure [18]. Sodium hydroxide (NaOH), aqua ammonia, dimethyl sulfoxide (DMSO), and diluted hydrochloric acid (HCl) were purchased from Tianjin Sailboat Chemical Reagent Co., Ltd., (Tianjin Guangfu Fine Chemical Research Institute, Tianjin, China) and used as received.…”

Section: Methodsmentioning

confidence: 99%

Poly(mono/diethylene glycol n-tetradecyl ether vinyl ether)s with Various Molecular Weights as Phase Change Materials

2018

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At present, research on the relationship of comb-like polymer phase change material structures and their heat storage performance is scarce. Therefore, this relationship from both micro and macro perspectives will be studied in this paper. In order to achieve a high phase change enthalpy, ethylene glycol segments were introduced between the vinyl and the alkyl side chains. A series of poly(mono/diethylene glycol n-tetradecyl ether vinyl ethers) (PC 14 E n VEs) (n = 1, 2) with various molecular weights were polymerized by living cationic polymerization. The results of PC 14 E 1 VE and PC 14 E 2 VE showed that the minimum number of carbon atoms required for side-chain crystallization were 7.7 and 7.2, which were lower than that reported in the literature. The phase change enthalpy 89 J/g (for poly(mono ethylene glycol n-tetradecyl ether vinyl ethers)) and 86 J/g (for poly(hexadecyl acrylate)) were approximately equal. With the increase of molecular weight, the melting temperature, the melting enthalpy, and the initial thermal decomposition temperature of PC 14 E 1 VE changed from 27.0 to 28.0 • C, from 95 to 89 J/g, and from 264 to 287 • C, respectively. When the number average molar mass of PC 14 E n VEs exceeded 20,000, the enthalpy values remained basically unchanged. The introduction of the ethylene glycol chain was conducive to the crystallization of alkyl side chains.

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“…1-(Isobutoxy)ethyl acetate (IBEA; CH 3 CH(OiBu)OCOCH 3 ) was prepared from IBVE and acetic acid as previously reported. 19 Commercial Et 1.5 AlCl 1.5 (Nippon Aluminum Alkyls, Tokyo, Japan; 1.0 M solution in toluene), EtAlCl 2 (Wako; 1.0 M solution in hexane), and TiCl 4 (Aldrich; 1.0 M solution in toluene) were used without further purification. All materials except for PIVE, hexane and toluene were stored in brown ampules under dry nitrogen.…”

Section: Experimental Procedures Materialsmentioning

confidence: 99%

Highly efficient synthesis of heteroarm star-shaped polymers using polymer-linking reaction and their characteristic stimuli-responsive behaviors

Oda

Shibata

Tsujimoto

et al. 2012

Polym J

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Heteroarm star-shaped polymers containing independent stimuli-responsive moieties were synthesized by a one-pot arm-linking reaction based on base-assisting living cationic polymerization. Mixing two or more kinds of living polymers followed by the linking reaction with a divinyl compound successfully produced a heteroarm star-shaped polymer containing a number of arm chains with a narrow molecular weight distribution (M w /M n ¼ 1.14-1.48) and high yield. For example, four kinds of linear poly(vinyl ether)s containing oxyethylene and alicyclic pendants were linked quantitatively to give a star polymer without any deactivation of the starting polymers. The heteroarm star-shaped polymers exhibited their unique stimuli-responsive behaviors in water or their film surfaces. Furthermore, linear living poly(2-methoxyethyl vinyl ether) and poly(2-phthalimidoethyl vinyl ether) were linked efficiently despite their different reactivities, producing a heteroarm star-shaped polymer with amino-containing and thermosensitive arms. The obtained star polymer exhibited unique aggregation behaviors in response to both pH and temperature in water. This report demonstrates that this one-pot arm-linking reaction is a facile and effective methodology for synthesis of heteroarm star polymers with various combinations of stimuli-responsive arm chains.

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Living cationic polymerization of vinyl monomers by organoaluminum halides. 3. Living polymerization of isobutyl vinyl ether by ethyldichloroaluminum in the presence of ester additives

Cited by 251 publications

References 2 publications

Lewis acid‐specific polymerization behaviors in living cationic polymerization of vinyl ether with a malonate group

Lewis acid‐specific polymerization behaviors in living cationic polymerization of vinyl ether with a malonate group

Poly(mono/diethylene glycol n-tetradecyl ether vinyl ether)s with Various Molecular Weights as Phase Change Materials

Highly efficient synthesis of heteroarm star-shaped polymers using polymer-linking reaction and their characteristic stimuli-responsive behaviors

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