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Erschienen in: Polymer Bulletin 5/2016

12.11.2015 | Original Paper

Synthesis of ionic liquid based on polysiloxane with quaternized imidazolium moiety

verfasst von: Tsukasa Ichikawa, Tsuyoshi Wako, Nobukatsu Nemoto

Erschienen in: Polymer Bulletin | Ausgabe 5/2016

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Abstract

Polysiloxane derivatives having quaternized imidazolium moieties with different length of alkyl chains ([HPIm n ]Cl) (n is the number of methylene group) were prepared via quaternization reaction of poly(3-chloropropylmethylsiloxane) (P1) with 1-alkylimidazole derivatives (Im ns). [HPIm n ]Cls were obtained with high quaternization ratio from 95 to 100 mol%. The glass transition temperatures (T gs) of a series of [HPIm n ]Cls were lowered with increase in the length of alkyl chain in the case of the number of methylene group from 1 to 6; however, those were a little raised when the number of methylene group was 7 and 8 plausibly owing to the effects of the van der Waals interactions among long alkyl chains. [HPIm n ]Cls were dissolved in high polar solvents such as methanol, dimethyl sulfoxide, N,N-dimethylformamide and water. Also, the increase in the length of alkyl chains in [HPIm n ]Cls improved the solubility in low polar organic solvents such as chloroform and dichloromethane.

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Literatur
1.
Zurück zum Zitat Earle MJ, Esperanca JM, Gilea MA, Lopes JN, Rebelo LP, Magee JW, Seddon RK, Widegren JA (2006) The distillation and volatility of ionic liquids. Nature 439:831–834CrossRef Earle MJ, Esperanca JM, Gilea MA, Lopes JN, Rebelo LP, Magee JW, Seddon RK, Widegren JA (2006) The distillation and volatility of ionic liquids. Nature 439:831–834CrossRef
2.
Zurück zum Zitat Fox DM, Gilman JW, Morgan AB, Shields JR, Maupin PH, Lyon RE, De Long HC, Trulove PC (2008) Flammability and thermal analysis characterization of imidazolium-based ionic liquids. Ind Eng Chem Res 47:6327–6332CrossRef Fox DM, Gilman JW, Morgan AB, Shields JR, Maupin PH, Lyon RE, De Long HC, Trulove PC (2008) Flammability and thermal analysis characterization of imidazolium-based ionic liquids. Ind Eng Chem Res 47:6327–6332CrossRef
3.
Zurück zum Zitat Galinski M, Lewandowski A, Stepniak I (2006) Ionic liquids as electrolytes. Electrochim Acta 51:5567–5580CrossRef Galinski M, Lewandowski A, Stepniak I (2006) Ionic liquids as electrolytes. Electrochim Acta 51:5567–5580CrossRef
4.
Zurück zum Zitat Nishimura N, Ohno H (2014) 15th anniversary of polymerized ionic liquids. Polymer 55:3289–3297CrossRef Nishimura N, Ohno H (2014) 15th anniversary of polymerized ionic liquids. Polymer 55:3289–3297CrossRef
5.
Zurück zum Zitat Yu B, Zhou F, Wang C, Liu W (2007) A novel gel polymer electrolyte based on poly ionic liquid 1-ethyl 3-(2-methacryloyloxy ethyl) imidazolium iodide. Eur Polym J 43:2699–2707CrossRef Yu B, Zhou F, Wang C, Liu W (2007) A novel gel polymer electrolyte based on poly ionic liquid 1-ethyl 3-(2-methacryloyloxy ethyl) imidazolium iodide. Eur Polym J 43:2699–2707CrossRef
6.
Zurück zum Zitat Batra D, Hay DNT, Firestone MA (2007) Formation of biomimetic, liquid-crystalline hydrogel by self-assembly and polymerization of an ionic liquid. Chem Mater 19:4423–4431CrossRef Batra D, Hay DNT, Firestone MA (2007) Formation of biomimetic, liquid-crystalline hydrogel by self-assembly and polymerization of an ionic liquid. Chem Mater 19:4423–4431CrossRef
7.
Zurück zum Zitat Batra D, Seifert S, Firestone MA (2007) The effect of cation structure on the mesophase architecture of self-assembled and polymerized imidazolium-based ionic liquids. Macromol Chem Phys 208:1416–1427CrossRef Batra D, Seifert S, Firestone MA (2007) The effect of cation structure on the mesophase architecture of self-assembled and polymerized imidazolium-based ionic liquids. Macromol Chem Phys 208:1416–1427CrossRef
8.
Zurück zum Zitat Matsumoto K, Talukdar B, Endo T (2011) Methacrylate-based ionic liquid: radical polymerization/copolymerization with methyl methacrylate and evaluation of molecular weight of the obtained homopolymers. Polym Bull 66:199–210CrossRef Matsumoto K, Talukdar B, Endo T (2011) Methacrylate-based ionic liquid: radical polymerization/copolymerization with methyl methacrylate and evaluation of molecular weight of the obtained homopolymers. Polym Bull 66:199–210CrossRef
9.
Zurück zum Zitat Tang J, Tang H, Sun W, Plancher H (2005) Poly(ionic liquid)s: a new material with enhanced and fast CO2 absorption. Chem Commun 26:3325–3327 Tang J, Tang H, Sun W, Plancher H (2005) Poly(ionic liquid)s: a new material with enhanced and fast CO2 absorption. Chem Commun 26:3325–3327
10.
Zurück zum Zitat Tang J, Tang H, Sun W, Radosz M, Shen Y (2005) Poly(ionic liquid)s as new materials for CO2 absorption. J Polym Sci Part A Polym Chem 43:5477–5489CrossRef Tang J, Tang H, Sun W, Radosz M, Shen Y (2005) Poly(ionic liquid)s as new materials for CO2 absorption. J Polym Sci Part A Polym Chem 43:5477–5489CrossRef
11.
Zurück zum Zitat Tang H, Tang J, Ding S, Radosz M, Shen Y (2005) Atom transfer radical polymerization of styrenic ionic liquid monomers and carbon dioxide absorption of the polymerized ionic liquids. J Polym Sci Part A Polym Chem 43:1432–1443CrossRef Tang H, Tang J, Ding S, Radosz M, Shen Y (2005) Atom transfer radical polymerization of styrenic ionic liquid monomers and carbon dioxide absorption of the polymerized ionic liquids. J Polym Sci Part A Polym Chem 43:1432–1443CrossRef
12.
Zurück zum Zitat Tang J, Radosz M, Shen Y (2008) Poly(ionic liquid)s as optically transparent microwave-absorbing materials. Macromolecules 41:493–496CrossRef Tang J, Radosz M, Shen Y (2008) Poly(ionic liquid)s as optically transparent microwave-absorbing materials. Macromolecules 41:493–496CrossRef
13.
Zurück zum Zitat Seno K, Kanaoka S, Aoshima S (2008) Synthesis and LCST-type phase separation behavior in organic solvents of poly(vinyl ethers) with pendant imidazolium or pyridinium salts. J Polym Sci Part A Polym Chem 46:5724–5733CrossRef Seno K, Kanaoka S, Aoshima S (2008) Synthesis and LCST-type phase separation behavior in organic solvents of poly(vinyl ethers) with pendant imidazolium or pyridinium salts. J Polym Sci Part A Polym Chem 46:5724–5733CrossRef
14.
Zurück zum Zitat Hu H, Yuan W, Lanshu L, Zhao H, Jia Z, Baker GL (2014) Low glass transition temperature polymer electrolyte prepared from ionic liquid grafted polyethylene oxide. J Polym Sci Part A Polym Chem 52:2104–2110CrossRef Hu H, Yuan W, Lanshu L, Zhao H, Jia Z, Baker GL (2014) Low glass transition temperature polymer electrolyte prepared from ionic liquid grafted polyethylene oxide. J Polym Sci Part A Polym Chem 52:2104–2110CrossRef
15.
Zurück zum Zitat Ohno H, Ito K (1998) Room-temperature molten salt polymers as a matrix for fast ion conduction. Chem Lett 27:751–752CrossRef Ohno H, Ito K (1998) Room-temperature molten salt polymers as a matrix for fast ion conduction. Chem Lett 27:751–752CrossRef
16.
Zurück zum Zitat Mark JE (1990) Silicon-containing polymers. In: Zeigler JM, Gordon Fearon FW (eds) Silicon-based polymer science. American Chemical Society, Washington, DC, pp 47–68 Mark JE (1990) Silicon-containing polymers. In: Zeigler JM, Gordon Fearon FW (eds) Silicon-based polymer science. American Chemical Society, Washington, DC, pp 47–68
17.
Zurück zum Zitat Mizerska U, Fortuniak W, Chojnowski J, Halasa R, Konopacka A, Werel W (2009) Polysiloxane cationic biocides with imidazolium salt (Ims) groups, synthesis and antibacterial properties. Eur Polym J 45:779–787CrossRef Mizerska U, Fortuniak W, Chojnowski J, Halasa R, Konopacka A, Werel W (2009) Polysiloxane cationic biocides with imidazolium salt (Ims) groups, synthesis and antibacterial properties. Eur Polym J 45:779–787CrossRef
18.
Zurück zum Zitat Niino M, Ueno Y, Araki T, Sekine Y (1983) Binding of methyl orange by water-soluble synthetic polyorganosiloxane. Polym Commun 24:124–128 Niino M, Ueno Y, Araki T, Sekine Y (1983) Binding of methyl orange by water-soluble synthetic polyorganosiloxane. Polym Commun 24:124–128
19.
Zurück zum Zitat Green MD, Cruz DS, Ye Y, Layman JM, Elabd YA, Winey KI, Long TE (2011) Alkyl-substituted N-vinylimidazolium polymerized ionic liquids: thermal properties and ionic conductivities. Macromol Chem Phys 212:2522–2528CrossRef Green MD, Cruz DS, Ye Y, Layman JM, Elabd YA, Winey KI, Long TE (2011) Alkyl-substituted N-vinylimidazolium polymerized ionic liquids: thermal properties and ionic conductivities. Macromol Chem Phys 212:2522–2528CrossRef
Metadaten
Titel
Synthesis of ionic liquid based on polysiloxane with quaternized imidazolium moiety
verfasst von
Tsukasa Ichikawa
Tsuyoshi Wako
Nobukatsu Nemoto
Publikationsdatum
12.11.2015
Verlag
Springer Berlin Heidelberg
Erschienen in
Polymer Bulletin / Ausgabe 5/2016
Print ISSN: 0170-0839
Elektronische ISSN: 1436-2449
DOI
https://doi.org/10.1007/s00289-015-1552-8

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