WO2021095600A1 - カーボンナノチューブ分散液およびその製造方法 - Google Patents

カーボンナノチューブ分散液およびその製造方法 Download PDF

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WO2021095600A1
WO2021095600A1 PCT/JP2020/041195 JP2020041195W WO2021095600A1 WO 2021095600 A1 WO2021095600 A1 WO 2021095600A1 JP 2020041195 W JP2020041195 W JP 2020041195W WO 2021095600 A1 WO2021095600 A1 WO 2021095600A1
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mpa
dispersion
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carbon nanotube
cellulose derivative
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French (fr)
Japanese (ja)
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斐之 野々口
壯 河合
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Nara Institute of Science and Technology NUC
Tatsuta Electric Wire and Cable Co Ltd
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Nara Institute of Science and Technology NUC
Tatsuta Electric Wire and Cable Co Ltd
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Priority to CN202080078761.2A priority Critical patent/CN114728796A/zh
Priority to JP2021556035A priority patent/JPWO2021095600A1/ja
Priority to KR1020227007134A priority patent/KR20220100572A/ko
Publication of WO2021095600A1 publication Critical patent/WO2021095600A1/ja
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    • 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
    • C01B32/174—Derivatisation; Solubilisation; Dispersion in solvents
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
    • C01B2202/00—Structure or properties of carbon nanotubes
    • C01B2202/20—Nanotubes characterized by their properties
    • C01B2202/36—Diameter

Definitions

  • the present invention relates to a carbon nanotube dispersion liquid and a method for producing the same.
  • Patent Document 1 does not show the relationship between the cellulose derivative and the selected solvent, and only extremely limited dispersion conditions are proposed. In addition, it is considered that such a technique may be accompanied by denaturation or deterioration of carbon nanotubes.
  • One aspect of the present invention is to provide a dispersion liquid capable of satisfactorily dispersing carbon nanotubes by a wide range of dispersion media specified by physical characteristics.
  • the present inventors include a dispersoid containing carbon nanotubes and a cellulose derivative, and a dispersion medium specified by the Hansen solubility parameter and the Hildebrand solubility parameter depending on the cellulose derivative.
  • the dispersion liquid disperses carbon nanotubes well, and have completed the present invention. That is, the present invention includes the following aspects. ⁇ 1> A dispersoid containing carbon nanotubes and a cellulose derivative represented by the following formula (1) and a dispersion medium are contained.
  • R is independently an H, an alkyl group, a hydroxyalkyl group, or an acyl group, except that at least one of R in the formula is an alkyl group, a hydroxyalkyl group, or an acyl group.
  • n 5 to 5000
  • the cellulose derivative and the dispersion medium are carbon nanotube dispersion liquids, which are any combination selected from the following (A) to (C).
  • Carbon nanotube dispersion liquid (A) Cellulose derivative having an alkyl group and Hansen solubility parameter have a dispersion term of 15.0 to 20.0 MPa 1/2 , a polar term of 1.5 to 15.0 MPa 1/2 , and a hydrogen bond term of 3.0 to. Dispersion medium, 23.0 MPa 1/2, (B) Cellulose derivative having a hydroxyalkyl group and Hansen solubility parameter have a dispersion term of 15.0 to 20.0 MPa 1/2 , a polar term of 5.0 to 17.5 MPa 1/2 , and a hydrogen bond term of 5.0.
  • Dispersion medium of ⁇ 50.0 MPa 1/2 (C) Cellulose derivative having an acyl group and Hansen solubility parameter have a dispersion term of 15.0 to 18.3 MPa 1/2 , a polar term of 5.0 to 20.0 MPa 1/2 , and a hydrogen bond term of 4.0 to 4.0.
  • R is independently an H, an alkyl group, a hydroxyalkyl group, or an acyl group, except that at least one of R in the formula is an alkyl group, a hydroxyalkyl group, or an acyl group.
  • n 5 to 5000
  • the cellulose derivative and the dispersion medium are a combination of any of the following (A) to (C), which is a method for producing a carbon nanotube dispersion liquid.
  • Method for producing carbon nanotube dispersion liquid (A) Cellulose derivative having an alkyl group and Hansen solubility parameter have a dispersion term of 15.0 to 20.0 MPa 1/2 , a polar term of 1.5 to 15.0 MPa 1/2 , and a hydrogen bond term of 3.0 to. Dispersion medium, 23.0 MPa 1/2, (B) Cellulose derivative having a hydroxyalkyl group and Hansen solubility parameter have a dispersion term of 15.0 to 20.0 MPa 1/2 , a polar term of 5.0 to 17.5 MPa 1/2 , and a hydrogen bond term of 5.0.
  • Dispersion medium of ⁇ 50.0 MPa 1/2 (C) Cellulose derivative having an acyl group and Hansen solubility parameter have a dispersion term of 15.0 to 18.3 MPa 1/2 , a polar term of 5.0 to 20.0 MPa 1/2 , and a hydrogen bond term of 4.0 to 4.0.
  • ⁇ 5> The method for producing a carbon nanotube dispersion liquid according to ⁇ 4>, wherein the cellulose derivative is at least one selected from the group consisting of ethyl cellulose, hydroxypropyl cellulose and acetyl cellulose.
  • ⁇ 6> The method for producing a carbon nanotube dispersion liquid according to ⁇ 4> or ⁇ 5>, wherein the carbon nanotube has a diameter of 0.5 to 250 nm.
  • a dispersion liquid capable of satisfactorily dispersing carbon nanotubes by using a wide range of dispersion media specified by physical characteristics.
  • the carbon nanotube dispersion liquid according to the embodiment of the present invention contains a dispersoid containing carbon nanotubes and a cellulose derivative represented by the following formula (1), and a dispersion medium.
  • R is independently an H, an alkyl group, a hydroxyalkyl group, or an acyl group, except that at least one of R in the formula is an alkyl group, a hydroxyalkyl group, or an acyl group.
  • n 5 to 5000
  • the cellulose derivative and the dispersion medium are any combination selected from the following (A) to (C).
  • (A) Cellulose derivative having an alkyl group and Hansen solubility parameter have a dispersion term of 15.0 to 20.0 MPa 1/2 , a polar term of 1.5 to 15.0 MPa 1/2 , and a hydrogen bond term of 3.0 to.
  • Dispersion medium 23.0 MPa 1/2
  • (B) Cellulose derivative having a hydroxyalkyl group and Hansen solubility parameter have a dispersion term of 15.0 to 20.0 MPa 1/2 , a polar term of 5.0 to 17.5 MPa 1/2 , and a hydrogen bond term of 5.0.
  • Dispersion medium of ⁇ 50.0 MPa 1/2 (C) Cellulose derivative having an acyl group and Hansen solubility parameter have a dispersion term of 15.0 to 18.3 MPa 1/2 , a polar term of 5.0 to 20.0 MPa 1/2 , and a hydrogen bond term of 4.0 to 4.0.
  • a method of dispersing carbon nanotubes a method of encapsulating the carbon nanotubes with micelles using a surfactant in water, or a method of coordinating or winding a conductive polymer on the carbon nanotubes in a hydrophobic aqueous solution. There is a method through attachment.
  • dispersion mediums for carbon nanotubes are highly polar water.
  • an organic solvent as a dispersion medium, a method of using an alcohol as a dispersion medium is also being studied, except for an aprotic solvent such as 1-methyl-2-pyrrolidone, which has a relatively high polarity and is highly toxic.
  • an aprotic solvent such as 1-methyl-2-pyrrolidone
  • the present inventors have conducted carbon nanotubes even if the dispersion medium is an organic solvent by using a dispersion liquid containing a dispersion medium specified by the Hansen solubility parameter and the Hildebrand solubility parameter. Was found to be able to be dispersed in a high yield. According to the dispersion liquid, it is not necessary to chemically modify the carbon nanotubes, so that the carbon nanotubes can be dispersed without being modified or deteriorated.
  • the carbon nanotube dispersion liquid according to one embodiment of the present invention is a mixture containing a dispersoid and a dispersion medium specified by the Hansen solubility parameter and the Hildebrand solubility parameter depending on the cellulose derivative.
  • a carbon nanotube dispersion liquid is also simply referred to as a "dispersion liquid”.
  • the dispersion liquid according to the embodiment of the present invention is a supernatant liquid obtained by centrifuging the dispersion liquid having a charge concentration of 0.25 g / L at 13200 ⁇ g for 10 minutes using carbon nanotubes having a central diameter of 1.8 nm.
  • the absorbance of the transition between the second bands in the absorption spectrum is preferably 0.1 or more.
  • the “second band-to-band transition” refers to the second smallest band gap (S22) among the plurality of band gaps found between the band structures reflecting the nanostructures in the carbon nanotubes.
  • the absorbance is indexed by the absorption spectrum corresponding to the transition between the second bands measured at an optical path length of 2 mm. According to Lambert's law, if the concentration of carbon nanotubes in the dispersion medium is constant, the absorbance is proportional to the optical path length.
  • the absorbance of the transition between the second bands of the dispersion is more preferably 0.5 or more, and even more preferably 1.0 or more. When the absorbance of the transition between the second bands of the dispersion liquid is 0.1 or more, it means that the carbon nanotubes could be dispersed in a high yield without the dispersoid precipitating in the dispersion medium.
  • the upper limit of the absorbance of the transition between the second bands of the dispersion liquid is not particularly limited, but the absorbance of the transition between the second bands when measured with a carbon nanotube having a central diameter of 1.8 nm and an optical path length of 2 mm is obtained. It is preferably 1.9 or less.
  • the above dispersion can be used as ink, paste, etc.
  • the dispersion liquid is used, for example, by being applied onto a substrate.
  • a substrate such as glass, transparent ceramics, metal, or plastic film can be used.
  • the thickness of the substrate is not particularly limited, but is preferably 1 ⁇ m to 1000 ⁇ m.
  • the method of applying the dispersion liquid onto the substrate is not particularly limited, but is limited to spin coating, extrusion die coating, blade coating, bar coating, screen printing, stencil printing, roll coating, curtain coating, spray coating, dip coating, and inkjet printing.
  • a known coating method such as Dispens can be used.
  • various devices suitable for applying the dispersion liquid can be used, and the present invention is not particularly limited.
  • Dispersion> refers to a mixture consisting of carbon nanotubes and a cellulose derivative, and carbon nanotubes and a cellulose derivative described later can be used in any combination.
  • the carbon nanotubes may be single-walled or multi-walled (for example, two-walled, three-walled, four-walled or more multi-walled). From the viewpoint of good dispersion, single-walled carbon nanotubes are preferable.
  • the diameter of the carbon nanotubes is preferably 0.5 to 250 nm, more preferably 0.5 to 10 nm, and even more preferably 0.5 to 5 nm from the viewpoint of dispersing the dispersoid.
  • the method for obtaining the carbon nanotubes is not particularly limited, and may be one synthesized based on a known technique or a commercially available one.
  • the concentration of carbon nanotubes in the dispersion is preferably 1 to 10000 mM, more preferably 10 to 1000 mM.
  • the concentration of carbon nanotubes in the ink can be calculated from the mass of carbon nanotubes in the dispersion liquid, for example, assuming that the atomic weight of carbon is 12.
  • R is independently an H (hydrogen atom), an alkyl group, a hydroxyalkyl group, or an acyl group, except that at least one of R in the formula is an alkyl group or a hydroxy group. It is an alkyl group or an acyl group.
  • Examples of the cellulose derivative having an alkyl group include methyl cellulose, ethyl cellulose, propyl cellulose, methyl ethyl cellulose, methyl propyl cellulose, ethyl propyl cellulose and the like.
  • the alkyl chain may be a straight chain or a branched chain.
  • Examples of the cellulose derivative having a hydroxyalkyl group include hydroxyethyl cellulose, hydroxypropyl cellulose, hydroxypropyl methyl cellulose and the like.
  • Examples of cellulose having an acyl group include acetyl cellulose and propionyl cellulose. Since these cellulose derivatives have a hydrophobic group, carbon nanotubes can be dispersed well.
  • the cellulose derivative is preferably at least one selected from the group consisting of ethyl cellulose, hydroxypropyl cellulose and acetyl cellulose.
  • Ethyl cellulose has a structure in which R is H or C 2 H 5 and at least one of R is C 2 H 5 in the formula (1).
  • Hydroxypropyl cellulose has a structure in which R is H or CH 2 CH (OH) CH 3 in the formula (1), and at least one of R is CH 2 CH (OH) CH 3 .
  • Acetyl cellulose has a structure in which R is H or COCH 3 in the formula (1), and at least one of R is COCH 3.
  • cellulose derivative only one kind of cellulose derivative may be used, or a mixture in which two or more kinds of cellulose derivatives are arbitrarily combined may be used.
  • the concentration of the dispersoid in the dispersion is not particularly limited, but is preferably 0.001 to 10.0 w / v%, more preferably 0.02 to 2.0 w / v%, and further, for example. It is preferably 0.1 to 1.0 w / v%.
  • Dispersion medium refers to a dispersion medium used to disperse carbon nanotubes.
  • examples of the dispersion medium include water and organic solvents, preferably organic solvents, and more preferably ethers, esters, ketones, alcohols, amines, amides, nitriles and the like.
  • ether examples include tetrahydrofuran (THF), 1,4-dioxane, diethyl ether, diethylene glycol dimethyl ether (bis (2-methoxyethyl) ether), ethyl carbitol acetate (diethylene glycol monoethyl ether acetate), and butyl carbitol acetate (diethylene glycol monoethyl ether acetate).
  • THF tetrahydrofuran
  • 1,4-dioxane diethyl ether
  • diethylene glycol dimethyl ether bis (2-methoxyethyl) ether
  • ethyl carbitol acetate diethylene glycol monoethyl ether acetate
  • butyl carbitol acetate diethylene glycol monoethyl ether acetate
  • Diethylene glycol monobutyl ether acetate dibenzyl ether, anisole and the like.
  • ester examples include ethyl acetate, butyl acetate (n-butyl acetate), dimethyl carbonate, ethyl lactate, butyl lactate, dimethyl phthalate, ⁇ -butyrolactone (GBL) and the like.
  • ketone examples include cyclohexanone, methyl ethyl ketone, acetone, methyl isobutyl ketone, 3-pentanone (diethyl ketone), acetophenone and the like.
  • alcohols examples include methanol, ethanol, isopropanol (2-propanol), 1-butanol, benzyl alcohol, phenol, 2-ethoxyethanol, ethylene glycol and the like.
  • Examples of other dispersion media include toluene, o-xylene, and a dispersion medium containing a nitrogen atom (1-methyl-2-pyrrolidone (N-methylpyrrolidone), 1-cyclohexyl-2-pyrrolidone (N-cyclohexylpyrrolidone), etc.
  • examples thereof include dimethylformamide, N, N'-dimethylpropylene urea, benzonitrile, acetonitrile, etc.), and dispersion media containing a sulfur atom (dimethylsulfoxide, etc.).
  • the dispersion medium may be a non-aromatic dispersion medium or a non-amide dispersion medium. Further, the dispersion medium may be a dispersion medium excluding a dispersion medium containing a nitrogen atom and a dispersion medium containing a sulfur atom, or a dispersion medium excluding an aprotic polar solvent.
  • the Hansen solubility parameter and the Hildebrand solubility parameter are used as indicators of the dispersibility of the dispersion medium.
  • the Hansen solubility parameter is a kind of parameter used by defining the Hildebrand solubility parameter ⁇ T , which predicts the solubility of one substance in another substance, with three-dimensional parameters ( ⁇ D , ⁇ P , ⁇ H). ..
  • the relationship between the Hildebrand solubility parameter and the Hansen solubility parameter is expressed by the following equation (2).
  • ⁇ T 2 ( ⁇ D ) 2 + ( ⁇ P ) 2 + ( ⁇ H ) 2 ... (2)
  • ⁇ D represents the dispersion term
  • ⁇ P represents the polarity term
  • ⁇ H represents the hydrogen bond term.
  • dispersion term is preferably from 15.0 ⁇ 20.0 MPa 1/2, and more preferably 15.0 ⁇ 18.0 MPa 1/2.
  • polarity term is 1.5 ⁇ 15.0 MPa 1/2, more preferably 1.5 ⁇ 7.5 MPa 1/2.
  • hydrogen bond is 3.0 ⁇ 23.0MPa 1/2, more preferably 3.0 ⁇ 12.0 MPa 1/2.
  • the dispersion term is preferably 15.0 to 20.0 MPa 1/2 , more preferably 15.5 to 18.5 MPa 1/2.
  • the polarity term is preferably 5.0 to 17.5 MPa 1/2 , and more preferably 6.5 to 12.5 MPa 1/2.
  • the hydrogen bond term is preferably 5.0 to 50.0 MPa 1/2 , and more preferably 6.0 to 30.0 MPa 1/2.
  • the dispersion term is preferably 15.0 to 18.3 MPa 1/2 , and more preferably 16.0 to 18.2 MPa 1/2.
  • polarity term is 5.0 ⁇ 20.0 MPa 1/2, more preferably 6.0 ⁇ 10.0 MPa 1/2.
  • the hydrogen bond term is preferably 4.0 to 13.5 MPa 1/2 , and more preferably 6.0 to 13.0 MPa 1/2.
  • the Hildebrand solubility parameter is 19.5 ⁇ 25.0 MPa 1/2, and more preferably 19.5 ⁇ 22.0MPa 1/2.
  • a dispersion liquid capable of dispersing carbon nanotubes in a high yield can be provided.
  • the dispersion medium only one kind of dispersion medium may be used, or a mixture in which two or more kinds of dispersion media are arbitrarily combined may be used.
  • the dispersion medium is a mixture, it is sufficient that at least one kind of dispersion medium contained in the mixture satisfies the above parameters.
  • the method for producing a dispersion liquid according to an embodiment of the present invention includes a step of dispersing a dispersoid containing carbon nanotubes and a cellulose derivative represented by the following formula (1) in a dispersion medium.
  • R is independently an H, an alkyl group, a hydroxyalkyl group, or an acyl group, except that at least one of R in the formula is an alkyl group, a hydroxyalkyl group, or an acyl group.
  • n 5 to 5000
  • the cellulose derivative and the dispersion medium are any combination selected from the following (A) to (C).
  • (A) Cellulose derivative having an alkyl group and Hansen solubility parameter have a dispersion term of 15.0 to 20.0 MPa 1/2 , a polar term of 1.5 to 15.0 MPa 1/2 , and a hydrogen bond term of 3.0 to.
  • Dispersion medium 23.0 MPa 1/2
  • (B) Cellulose derivative having a hydroxyalkyl group and Hansen solubility parameter have a dispersion term of 15.0 to 20.0 MPa 1/2 , a polar term of 5.0 to 17.5 MPa 1/2 , and a hydrogen bond term of 5.0.
  • Dispersion medium of ⁇ 50.0 MPa 1/2 (C) Cellulose derivative having an acyl group and Hansen solubility parameter have a dispersion term of 15.0 to 18.3 MPa 1/2 , a polar term of 5.0 to 20.0 MPa 1/2 , and a hydrogen bond term of 4.0 to 4.0.
  • Examples of the method for dispersing the dispersoid in the dispersion medium include a method using a homogenizing device.
  • Examples of the homogenizer include a stirring homogenizer and an ultrasonic homogenizer. From the viewpoint of more uniform dispersion, it is preferable to disperse the dispersoid in the dispersion medium using an ultrasonic homogenizer.
  • the time for dispersion is not particularly limited, but is, for example, 5 to 60 minutes, preferably 10 to 30 minutes.
  • the temperature at which dispersion is performed is also not particularly limited, but is, for example, 5 ° C.
  • Dispersion 2 by the same method as dispersions 1- (1), 1- (2) and 1- (3) except that benzyl alcohol was changed to each of the dispersion media shown in Tables 1 and 2 below. -37 (1), (2) and (3) were obtained.
  • the dispersion media used in the dispersion liquids 1 to 37 are shown in Tables 1 and 2 below.
  • the Hansen solubility parameter and Hildebrand solubility parameter of the dispersion medium used in the dispersion liquids 1 to 37, and the absorbance of the transition between the second bands of the dispersion liquids 1 to 37 are shown in Tables 3 to 9 below.
  • Tables 3, 4 and 7 were used for the dispersions prepared using (1) ethyl cellulose solution
  • Tables 5 and 8 were used for the dispersions prepared using (2) hydroxypropyl cellulose solution, and (3) acetyl cellulose solution was used.
  • the dispersions produced in the above are shown in Tables 6 and 9.
  • the Hansen solubility parameter of the dispersion medium is described in the literature: Grulke, EA Solubility Parameter Values.
  • the evaluation criteria are ⁇ for the absorbance of the transition between the second bands of 0.1 or more when the optical path length is 2 mm, ⁇ for those with less than 0.1, and “-” for those that cannot be measured.
  • the absorbance of the transition between the second bands is about 1.9 when the optical path length is 2 mm, it corresponds to the total amount of the charged carbon nanotubes being dispersed.
  • the absorbance of the transition between the second bands is 0.1 or more when the optical path length is 2 mm, it corresponds to a dispersion yield of about 5% or more.
  • the "dispersion yield” is a ratio indicating how much the carbon nanotubes are dispersed in the dispersion medium with respect to the amount of carbon nanotubes added to the dispersion medium. Specifically, it is calculated from the ratio of the absorbance of the transition between the second bands of each dispersion medium when the absorbance of the transition between the second bands is 100% when the carbon nanotubes are completely dispersed in the dispersion medium. Will be done.
  • the dispersion liquid according to the embodiment of the present invention can disperse carbon nanotubes in an organic solvent in a high yield.
  • HiPco Nanointegras small diameter single-walled carbon nanotubes
  • PT Raymor Industries Plasma Tubes single-walled carbon nanotubes
  • AD Sigma-Aldrich 689695 single-walled carbon nanotubes
  • Tubel OCSiAl single-walled carbon nanotubes
  • FIG. 1 The results are shown in Fig. 1.
  • the vertical axis of FIG. 1 shows the absorbance of the dispersion liquid, and the horizontal axis shows the observation wavelength.
  • the absorbance of the transition between the second bands is proportional to the concentration of the dispersed carbon nanotubes. In these dispersions, the peak absorbance of the transition between the second bands could be confirmed in all carbon nanotubes. That is, it was suggested that the dispersion liquid according to the embodiment of the present invention can disperse carbon nanotubes in an organic solvent.
  • One aspect of the present invention can be suitably used for producing inks and pastes in which carbon nanotubes are dispersed.

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PCT/JP2020/041195 2019-11-14 2020-11-04 カーボンナノチューブ分散液およびその製造方法 Ceased WO2021095600A1 (ja)

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WO2023090403A1 (ja) * 2021-11-22 2023-05-25 日本ゼオン株式会社 カーボンナノチューブ分散液、炭素膜の製造方法、エラストマー混合液、複合材料の製造方法、及びエラストマー成形体の製造方法
WO2023145612A1 (ja) * 2022-01-31 2023-08-03 日本ゼオン株式会社 カーボンナノチューブ分散液、非水系二次電池負極用スラリー、非水系二次電池用負極及び非水系二次電池
WO2025058672A3 (en) * 2023-04-13 2025-04-24 Molecular Rebar Design, Llc Coatings with discrete carbon nanotubes for energy storage and additive manufacturing

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WO2023090403A1 (ja) * 2021-11-22 2023-05-25 日本ゼオン株式会社 カーボンナノチューブ分散液、炭素膜の製造方法、エラストマー混合液、複合材料の製造方法、及びエラストマー成形体の製造方法
WO2023145612A1 (ja) * 2022-01-31 2023-08-03 日本ゼオン株式会社 カーボンナノチューブ分散液、非水系二次電池負極用スラリー、非水系二次電池用負極及び非水系二次電池
WO2025058672A3 (en) * 2023-04-13 2025-04-24 Molecular Rebar Design, Llc Coatings with discrete carbon nanotubes for energy storage and additive manufacturing

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