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WO2006112162A1 - Composition sous forme de gel et son procede de production - Google Patents

Composition sous forme de gel et son procede de production Download PDF

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Publication number
WO2006112162A1
WO2006112162A1 PCT/JP2006/303952 JP2006303952W WO2006112162A1 WO 2006112162 A1 WO2006112162 A1 WO 2006112162A1 JP 2006303952 W JP2006303952 W JP 2006303952W WO 2006112162 A1 WO2006112162 A1 WO 2006112162A1
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Prior art keywords
group
ionic liquid
gel
gel composition
neutralized salt
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/JP2006/303952
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English (en)
Japanese (ja)
Inventor
Gen Masuda
Yasuharu Kato
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Nisshinbo Holdings Inc
Original Assignee
Nisshinbo Industries Inc
Nisshin Spinning Co Ltd
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Publication of WO2006112162A1 publication Critical patent/WO2006112162A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B82—NANOTECHNOLOGY
    • B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
    • B82Y40/00—Manufacture or treatment of nanostructures
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B82—NANOTECHNOLOGY
    • B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
    • B82Y30/00—Nanotechnology for materials or surface science, e.g. nanocomposites
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
    • C01B32/00—Carbon; Compounds thereof
    • C01B32/15—Nano-sized carbon materials
    • C01B32/158—Carbon nanotubes
    • C01B32/168—After-treatment
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/09—Carboxylic acids; Metal salts thereof; Anhydrides thereof

Definitions

  • the present invention relates to a gel composition and a method for producing the same, and more specifically to a gel composition comprising carbon nanotubes and a neutralized salt type ionic liquid, and a method for producing the same.
  • Carbon nanotubes have various electrical properties ranging from metallic properties to semiconducting properties, and are attracting attention as new additives that can improve the physical properties of materials due to their mechanical strength properties. Take a bath.
  • carbon nanotubes exist in the form of a large bundle that is not as long as a single tube, and thus it has been pointed out that it has the disadvantage of poor processability and is difficult to put into practical use.
  • the above-described method (1) for increasing affinity by chemical treatment requires a separate process for chemically treating carbon nanotubes, resulting in complicated processes and increased costs, and chemical modification. Therefore, the problem that the characteristics of the carbon nanotube are impaired is pointed out.
  • the method (2) for dispersing without chemical treatment requires the use of a special dispersion medium with a complicated structure, which is also disadvantageous in terms of cost.
  • the dispersion method may cause the carbon nanotubes to re-aggregate when applied to a substrate or the like where the dispersion of the carbon nanotubes becomes insufficient and tends to occur.
  • the ionic liquid to be used has a high purity.
  • many ionic liquids are expensive because they have fluorine atoms in the structure, and there are concerns about environmental impact.
  • a gel composition is used, there is a problem that time is required for gelling.
  • Patent Document 1 Japanese Patent Application Laid-Open No. 2004-216516
  • Patent Document 2 Japanese Patent Laid-Open No. 2003-238126
  • Patent Document 3 Japanese Patent Laid-Open No. 2002-244490
  • Patent Document 4 Japanese Patent Laid-Open No. 2002-255528
  • Patent Document 5 Japanese Patent Application Laid-Open No. 2004-255481
  • Patent Document 6 Japanese Unexamined Patent Application Publication No. 2004-142972
  • the present invention has been made in view of such circumstances, and is a gel-like composition that is excellent in dispersibility of carbon nanotubes, is excellent in environmental adaptability, and can be obtained relatively inexpensively. And it aims at providing the simple manufacturing method.
  • the present inventor has obtained a neutralization reaction of an acid, preferably a benzoic acid, and a base as a gelling medium for carbon nanotubes.
  • the inventors have found that a gel-like composition in which carbon nanotubes are well dispersed can be obtained easily and quickly by using a Japanese salt type ionic liquid, and completed the present invention.
  • a gel composition comprising carbon nanotubes and a neutralized salt-type ion liquid obtained by a neutralization reaction of an acid and a base,
  • the neutralized salt type ionic liquid contains benzoic acid or a derivative thereof as an anion component.
  • 1 gel-like composition characterized in that
  • Gelatin composition according to 2 characterized by being represented by the following formula (1):
  • Ri to R 5 may be the same as or different from each other, a hydrogen atom, a hydroxyl group, a linear or branched alkyl group having 1 to 6 carbon atoms [this alkyl group is a bur group, a aryl group, a pro It may be substituted with a pargyl group, an attalyloyl group, a methacryloyl group or an epoxy group. ], — (CH) —OR ′ group, — (CH) —SR ′ group, — (CH) — OCO—R ′ group
  • Neutralized salt form obtained by neutralization of carbon nanotubes with acid and base
  • a method for producing a gel-like composition comprising applying a shearing force to a mixture obtained by mixing an on-liquid,
  • a neutralized salt type ionic liquid is used as a gelling (dispersing) medium for carbon nanotubes, so that a gel-like composition can be obtained at a lower cost and more easily than conventional methods. be able to.
  • the gel-like composition can be easily produced by simply mixing an acid and a base and carbon nanotubes and applying a shearing force, and a quaternary salt type ionic liquid is used as a gelling medium. Compared to the case, gelation speed is faster!
  • a carbon nanotube-containing polymer can be easily obtained by using a neutralized salt type ionic liquid having a polymerizable group.
  • This polymer is superior in electrical properties such as electrical conductivity compared to a polymer obtained using a quaternary salt type ionic liquid having a polymerizable group.
  • the gel composition according to the present invention comprises carbon nanotubes and a neutralized salt type ionic liquid obtained by a neutralization reaction of an acid and a base.
  • the carbon nanotube is a carbon-based material that has the shape force of a dullafen sheet rolled into a cylindrical shape.
  • Single-walled carbon nanotubes and double-walled carbon nanotubes are determined from the number of peripheral walls. They can be broadly classified into tubes and multi-walled carbon nanotubes, and any of them can be used in the gel composition of the present invention. In the present invention, single-walled carbon nanotubes are particularly suitable.
  • the neutralized salt type ionic liquid is a liquid salt obtained by a neutralization reaction between an acid and a base.
  • the ionic liquid is not particularly limited as long as it is a liquid at 100 ° C or lower, but it is preferably a liquid at 50 ° C or lower, more preferably 30 ° C or lower, in view of handling at around room temperature. It is desirable that there be.
  • Examples of the acid constituting the neutralized salt type ionic liquid include carboxylic acid such as trifluoroacetic acid, benzoic acid, propionic acid, formic acid, and derivatives thereof, sulfonic acid such as methanesulfonic acid, and derivatives thereof, HC1 , H SO, HNO, HBF, HPF, (CF SO) NH, etc.
  • benzoic acid and its derivatives propionic acid, formic acid, methanesulfonic acid, H 2 SO, and HNO, which do not contain halogen atoms, are suitable in view of obtaining a gel composition having a low environmental impact. .
  • benzoic acid or a derivative thereof is suitable, and by using these, a gel composition in which carbon nanotubes are more dispersed (large volume) can be obtained.
  • benzoic acid or a derivative thereof for example, those represented by the following formula (1) can be suitably used without particular limitation.
  • Ri to R 5 may be the same as or different from each other, a hydrogen atom, a hydroxyl group, a linear or branched alkyl group having 1 to 6 carbon atoms [this alkyl group is a bur group, a aryl group, a pro It may be substituted with a pargyl group, an attalyloyl group, a methacryloyl group or an epoxy group. ], — (CH) —OR ′ group, — (CH) —SR ′ group, — (CH) — OCO—R ′ group
  • n Represents a branched alkyl group having 1 to 6 carbon atoms (this alkyl group may be substituted with a buyl group, a allyl group, a propargyl group, an attalyloyl group, a methacryloyl group or an epoxy group), and n is 1. Indicates an integer of ⁇ 6. ], A bur group, a allyl group, a propargyl group, an attalyl group, a methacryloyl group, or an epoxy group. ⁇
  • linear or branched alkyl group having 1 to 6 carbon atoms include a methyl group, an ethinole group, an n-propinole group, an i-propinole group, an n-butinole group, an s-butinole group, an i-butinore group.
  • t-butinole group t-butinole group, n-pentinole group, i-pentinole group, neo pentinole group, t-pentinole group, 1 methylbutyl group, 2-methylbutyl group, 1-ethylpropyl group, n-hexyl group, i-hexyl group, Examples thereof include 1-methylpentyl group, 1,3 dimethylbutoxy group, 1-ethylbutyl group, 2-ethylbutyl group and the like.
  • n is a force of 1 to 6 Since a low molecular weight tends to become an ionic liquid, a force of 1 to 4 is preferable, and 1 to 2 is more preferable.
  • SR 'groups examples include CH SCH,-(CH) SCH,-(CH)
  • COC H one CH NHCOC H, one (CH) NHCOC H, one (CH) NHCOC H, and
  • NHC H one CH CONHC H, one (CH) CONHC H, one (CH) CONHC H, and
  • COR ′ group examples include —COCH, —COC H, —COC H, —COC H, —COC H
  • Ri to R 5 are represented by a hydrogen atom, a methyl group, an ethyl group, and n-propylene because they are easier to synthesize, more easily available, and more easily have a low molecular weight. And an alkoxyalkyl group having a total carbon number of less than 3 are preferred.
  • Preferred examples of the benzoic acid of the present invention include those represented by the following formulas (2) to (6), but are not limited thereto.
  • the base is not particularly limited, but amines, amidines, and guanidines are preferable.
  • amines include primary amines, secondary amines, and tertiary amines.
  • ammonia dimethylamine, jetylamine, triethylamine, dimethylethylamine, 2-methoxyethylamine, jetyl ( 2-methoxyethyl) amine, pyridine, piperidine, pyrrolidine, carbazole, indole, cyclohexylamine, aminohexanol, 2- (methylamino) ethanol, aline, hexamethylenediamine, dimethylallylamine Min and so on.
  • amidines include imidazole, N-methylimidazole, 2-methylimidazole and the like.
  • guanidines examples include 1,1,3,3-tetramethyldardine and 1,3-diphenyldazine.
  • the acid component and the Z or base component described above may have a polymerizable group therein.
  • the gel composition obtained using the neutralized salt type ionic liquid having a polymerizable group can be easily polymerized by polymerizing the polymerizable group present therein.
  • examples of the polymerizable group include a photopolymerizable functional group, a thermopolymerizable functional group, and a polyaddition functional group that are activated by light irradiation, heating, a polymerization initiator, a catalyst, and the like, and specific examples thereof.
  • Examples of such a force include, but are not limited to, a vinyl group, an aryl group, a propargyl group, an attalyloyl group, a methacryloyl group, an epoxy group, and an isocyanate group.
  • the resulting polymer skeleton can be composed of the acid component.
  • the above-described benzoic acid or derivative thereof is used.
  • Those having a polymerizable group are preferred.
  • Ri to R 5 in the formula (1) described above is preferably a polymerizable group such as a bur group, a allyl group, a propargyl group, an attalyloyl group, a methacryloyl group, and an epoxy group.
  • a vinyl group, an talyloyl group and a methacryloyl group are preferred.
  • Specific examples of the acid having a polymerizable group include a force S such as those represented by the following formulas (21) to (24).
  • Specific examples of the base having a polymerizable group include the following formulas (25) to (30 ) And so on.
  • the neutralized salt type ionic liquid described above can be obtained by a known acid-base neutralization method. For example, an acid and a base are mixed at a molar ratio of 1: 1 under cooling such as ice cooling. After mixing, the temperature can be raised to an appropriate temperature and stirred for 1 to 24 hours.
  • the method for producing the gel composition of the present invention is not particularly limited, but a carbon nanotube and a neutralized salt type ionic liquid obtained by neutralization reaction of acid and base are mixed. A method of applying a shearing force to the obtained mixture is preferably used.
  • the mixture can be prepared by neutralizing an acid and a base, and preparing a neutralized salt type ionic liquid and isolating it, and then adding carbon nanotubes.
  • Directly (without isolating or purifying ionic liquids) A method of covering single-bonn nanotubes can also be used.
  • an acid or base and carbon nanotubes are mixed, and then mixed into the mixture by a method of adding a base or acid thereto.
  • a known shearing force applying means force can be appropriately selected and used. Specific examples include a method of manually or automatically kneading in a mortar, a method using a ball mill, a roller mill, a vibration mill, a kneader type kneader, and the like.
  • the time for applying the shearing force is not particularly limited, and may be an appropriate time for obtaining a gel composition. In the present invention, it is usually 1 to: LO minutes, and in some cases, 1 to 5 minutes. A gel composition can be obtained in a short time.
  • a black gel composition is obtained.
  • the obtained composition can be used for various purposes as it is, but if necessary, the excess neutralized salt type ionic liquid may be removed by centrifugation.
  • the specific method and conditions of centrifugation are arbitrary force. Usually, the conditions of 1000-15000 rpm and 5-30 minutes are adopted.
  • the amount of surplus ionic liquid is reduced as compared with the case where other neutralized salt type ionic liquids are used.
  • a gel-like composition obtained using an ionic liquid containing benzoic acid or a derivative thereof as a constituent component has a larger gel volume than when other ionic liquids are used. Accordingly, it can be said that a certain amount of carbon nanotubes are contained in a gel having a larger volume, and a gel-like composition having excellent dispersibility is generated.
  • neutralized salt type ionic liquid 1: 100 (mass ratio)
  • the excess ionic liquid produced by centrifugation is usually 25% by mass or less of the ionic liquid used.
  • the gel-like composition obtained using the neutralized salt type ionic liquid having a polymerizable group is polymerized in the gel-like composition by a conventionally known means such as heating, ultraviolet ray irradiation, electron beam irradiation and the like. The group can be reacted to polymerize.
  • a polymerization initiator may be added to the gel composition before the polymerization reaction.
  • the blending may be performed when preparing a mixture of carbon nanotubes and ionic liquid, which may be performed after the gel composition.
  • what is necessary is just to select and use suitably from a well-known various thing as a polymerization initiator.
  • the carbon nanotube-containing polymer thus obtained preferably has a low volume resistivity and exhibits excellent electrical conductivity.
  • the volume resistivity is preferably 5. ⁇ ⁇ m or less. 2. ⁇ ⁇ ⁇ or less is more preferable.
  • the electrical conductivity is preferably 2 ⁇ 10— ⁇ ⁇ or more, and more preferably 5 ⁇ 10— ⁇ ⁇ or more.
  • the carbon nanotube-containing polymer of the present invention uses a neutralized salt type ionic liquid as a gelling agent !, it is compared with a polymer using a conventionally known quaternary salt type ionic liquid as a gelling agent. Excellent electrical characteristics such as electrical conductivity.
  • Benzoic acid manufactured by Kanto Chemical Co., Inc.
  • 1-methylimidazole manufactured by Kanto Chemical Co., Ltd.
  • a neutralized salt type ionic liquid (31) represented by the following formula.
  • the target product was a liquid at room temperature (25 ° C).
  • Neutralized salt type ionic liquid obtained (31) (not isolated / purified) 100 parts by mass and single-walled carbon nanotube (HiPco: Carbon Nanotechnologies) (hereinafter referred to as SWC NT) 1
  • SWC NT single-walled carbon nanotube
  • a neutralized salt type ionic liquid (33) of the following formula was obtained in the same manner as in Example 1 except that triethylamine (Kanto Chemical Co., Ltd.) was used instead of 1-methylimidazole.
  • the target product was a liquid at room temperature (25 ° C).
  • a gel composition was obtained in the same manner as in Example 1 except that this ionic liquid (33) was used. In addition, the surplus ionic liquid was 20 mass% with respect to the used ionic liquid.
  • Example 1 except that pyrrolidine (manufactured by Wako Pure Chemical Industries, Ltd.) was used instead of 1-methylimidazole, and m-toluic acid (manufactured by Kanto Igaku) was used instead of benzoic acid.
  • a neutralized salt type ionic liquid (35) represented by the following formula was obtained.
  • the target product was a liquid at room temperature (25 ° C).
  • a gel composition was obtained in the same manner as in Example 1 except that this ionic liquid (35) was used. In addition, the surplus ionic liquid was 10 mass% with respect to the used ionic liquid.
  • Jetylamine (Kanto Chemical Co., Ltd.) 100ml and 2-methoxyethyl chloride (Kanto Chemical Co., Ltd.) 85ml were mixed, and the resulting mixed solution was placed in an autoclave at 100 ° C. For 24 hours. At this time, the internal pressure was 1.3 kgfZcm 2 . After 24 hours, 200 ml of an aqueous solution in which 56 g of potassium hydroxide (made by Katayama Chemical Co., Ltd.) was dissolved was added to the mixture of the precipitated crystal and the reaction solution, and the organic layer separated into two layers was separated into a separating funnel. The liquid was separated.
  • a gel composition was obtained in the same manner as in Example 1 except that this ionic liquid (39) was used. In addition, the surplus ionic liquid was 2 mass% with respect to the used ionic liquid.
  • Example 2 The following formula was used in the same manner as in Example 1, except that 2-methoxyethyldetilamine was used instead of 1-methylimidazole and methanesulfonic acid (manufactured by Tokyo Chemical Industry Co., Ltd.) was used instead of benzoic acid.
  • the ionic liquid (36) shown in 3 was obtained.
  • the target product was a liquid at room temperature (25 ° C).
  • a gel composition was obtained in the same manner as in Example 1 except that this ionic liquid (36) was used and kneaded in a mortar for 8 minutes. In addition, the surplus ionic liquid was 33 mass% with respect to the used ionic liquid.
  • a neutralized salt ionic liquid (40) represented by the following formula was obtained in the same manner as in Example 1 except that methanesulfonimide (manufactured by Kanto Chemical Co., Ltd.) was used.
  • the target product was a liquid at room temperature (25 ° C).
  • a gel composition was obtained in the same manner as in Example 1 except that this ionic liquid (40) was used and kneaded in a mortar for 8 minutes.
  • the surplus ionic liquid was 3% by mass with respect to the ionic liquid used.
  • Example 1 except that quaternary salt-type ionic liquid 1-ethyl 3-methylimidazolium tetrafluoroborate (EMIBF4) (Kanto Yigaku Co., Ltd.) was used and kneaded in a mortar for 20 minutes. In the same manner as above, a gel composition was obtained. The excess ionic liquid was 42% by mass with respect to the ionic liquid used.
  • EMIBF4 quaternary salt-type ionic liquid 1-ethyl 3-methylimidazolium tetrafluoroborate
  • Example 1 except that quaternary salt-type ionic liquid 1-butyl-3-methylimidazole hexafluorophosphate (BMIPF6) (Kanto Yigaku Co., Ltd.) was used and kneaded in a mortar for 10 minutes. A gel composition was obtained. The surplus ionic liquid was 25% by mass with respect to the ionic liquid used.
  • MIPF6 quaternary salt-type ionic liquid 1-butyl-3-methylimidazole hexafluorophosphate
  • N, N-jetyl-N-methyl-N- (2-methoxyethyl) ammotetrafluoroborate (Kantoi Chemical Co., Ltd.) in a mortar
  • a gel-like composition was obtained in the same manner as in Example 1 except that the mixture was kneaded for 1 minute.
  • the surplus ionic liquid was 30% by mass with respect to the ionic liquid used.
  • 2-methylaminoethyl methacrylate (made by Wako Pure Chemical Industries, Ltd.) 12.04 g is dissolved in 30 ml of tetrahydrofuran (Wako Pure Chemical Industries, Ltd.). (Manufactured by Kogyo Co., Ltd.) 4. 86 ml was collected. After 30 minutes, the ice bath was removed and the mixture was stirred overnight at room temperature. The solvent of this reaction solution was distilled off under reduced pressure, and the resulting solid content was recrystallized with ethanol (manufactured by Wako Pure Chemical Industries, Ltd.)-Tetrahydrofuran system to give 17-jetylmethylaminoethyl iodine salt of methacrylate. 22g was obtained.
  • a gel composition was obtained in the same manner as in Example 1 except that this quaternary salt type ionic liquid (42) was used and kneaded in a mortar for 10 minutes. The excess ionic liquid was 5% by mass with respect to the ionic liquid used.
  • Polymerizable group-containing neutralized salt type ionic liquid (39) 2 parts by mass of 2, 2 dimethoxy-2-phenylacetophenone (manufactured by Tokyo Chemical Industry Co., Ltd.) as a polymerization initiator is dissolved in 100 parts by mass Then, after adding 3.8 parts by mass of SWCNT to this, and applying a shearing force in the same manner as in Example 1, a black paste was obtained. This is sandwiched between polyethylene terephthalate sheets (Therapeutic, Toray Film Co., Ltd., 100 / zm), and UV irradiation is performed for 15 minutes. As a result, a neutralized salt type ionic liquid ZSWCNT composite film containing a polymerizable group was produced.
  • a polymerizable group-containing neutralized salt ion / SWCNT composite film was prepared in the same manner as in Example 9 except that the polymerizable group-containing neutralized salt type ionic liquid (40) was used.
  • a polymerizable group-containing quaternary salt type ion, SWCNT composite film was prepared in the same manner as in Example 9 except that the polymerizable group-containing quaternary salt type ionic liquid (42) was used.

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  • Nanotechnology (AREA)
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Abstract

L’invention concerne une composition sous forme de gel caractérisée en ce qu’elle comprend des nanotubes de carbone et un sel de neutralisation de type liquide ionique obtenu par la réaction de neutralisation d'un acide avec une base. Cette composition sous forme de gel est excellente en termes de dispersibilité des nanotubes de carbone et de respect de l’environnement et peut être obtenue à un coût relativement faible. En particulier, l’utilisation de l'acide benzoïque ou d’un dérivé de celui-ci en tant qu’acide constituant le sel de neutralisation de type liquide ionique donne une composition sous forme de gel ayant une excellente dispersibilité des nanotubes de carbone.
PCT/JP2006/303952 2005-03-31 2006-03-02 Composition sous forme de gel et son procede de production Ceased WO2006112162A1 (fr)

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Cited By (4)

* Cited by examiner, † Cited by third party
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WO2013146745A1 (fr) * 2012-03-30 2013-10-03 国立大学法人 東京大学 Procédé de production de gel contenant un liquide ionique
RU2777040C1 (ru) * 2021-12-29 2022-08-01 МСД Текнолоджис С.а р.л. Водная дисперсия углеродных нанотрубок, способ приготовления дисперсии, катодная паста, анодная паста, способ изготовления катода, способ изготовления анода, катод и анод
WO2023128801A1 (fr) 2021-12-29 2023-07-06 МСД Текнолоджис С.а р.л. Dispersion aqueuse de nanotubes de carbone, pâte, cathode et anode
WO2023128802A1 (fr) 2021-12-29 2023-07-06 МСД Текнолоджис С.а р.л. Dispersion de nanotubes de carbone, pâte cathodique et cathode

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JP5018460B2 (ja) * 2007-12-26 2012-09-05 東洋インキＳｃホールディングス株式会社 カーボンナノチューブ分散体及びそれを用いてなる樹脂組成物ならびに成形体
JP5594727B2 (ja) * 2009-06-22 2014-09-24 独立行政法人産業技術総合研究所 カーボンナノチューブのより簡便な分離回収方法
JP5553282B2 (ja) 2010-03-05 2014-07-16 独立行政法人産業技術総合研究所 カーボンナノチューブの分離回収方法及びカーボンナノチューブ
EP2571909B1 (fr) * 2010-05-18 2016-10-05 3M Innovative Properties Company Liquide ionique polymérisable comprenant un anion carboxylate aromatique
US8383721B2 (en) * 2010-05-18 2013-02-26 3M Innovative Properties Company Polymerizable ionic liquid compositions
JP5994982B2 (ja) * 2012-07-20 2016-09-21 国立研究開発法人産業技術総合研究所 電解質としてイオン性液体、空気極としてカーボンを分散したイオン性ゲルを用いたリチウム−空気二次電池

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Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013146745A1 (fr) * 2012-03-30 2013-10-03 国立大学法人 東京大学 Procédé de production de gel contenant un liquide ionique
RU2777040C1 (ru) * 2021-12-29 2022-08-01 МСД Текнолоджис С.а р.л. Водная дисперсия углеродных нанотрубок, способ приготовления дисперсии, катодная паста, анодная паста, способ изготовления катода, способ изготовления анода, катод и анод
RU2777379C1 (ru) * 2021-12-29 2022-08-02 МСД Текнолоджис С.а р.л. Дисперсия углеродных нанотрубок, способ приготовления дисперсии, катодная паста, способ изготовления катода и катод
WO2023128801A1 (fr) 2021-12-29 2023-07-06 МСД Текнолоджис С.а р.л. Dispersion aqueuse de nanotubes de carbone, pâte, cathode et anode
WO2023128802A1 (fr) 2021-12-29 2023-07-06 МСД Текнолоджис С.а р.л. Dispersion de nanotubes de carbone, pâte cathodique et cathode
US12482825B1 (en) 2021-12-29 2025-11-25 Mcd Technologies S.A. R.L Aqueous carbon nanotube dispersion, paste, cathode and anode

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