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WO2007052739A1 - Solubilisation de nanotube de carbone au moyen de polyimide aromatique - Google Patents

Solubilisation de nanotube de carbone au moyen de polyimide aromatique Download PDF

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Publication number
WO2007052739A1
WO2007052739A1 PCT/JP2006/321962 JP2006321962W WO2007052739A1 WO 2007052739 A1 WO2007052739 A1 WO 2007052739A1 JP 2006321962 W JP2006321962 W JP 2006321962W WO 2007052739 A1 WO2007052739 A1 WO 2007052739A1
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Prior art keywords
polyimide
aromatic polyimide
carbon nanotube
solution
solvent
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English (en)
Japanese (ja)
Inventor
Naotoshi Nakashima
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Kyushu University NUC
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Kyushu University NUC
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
    • C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • 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
    • 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
    • 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
    • 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
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/02—Elements
    • C08K3/04—Carbon
    • C08K3/041—Carbon nanotubes

Definitions

  • the present invention belongs to the technical field of nanotechnology, and particularly relates to a novel technique for solubilizing carbon nanotubes.
  • Non-patent Document 1 carbon nanotubes discovered in sediments during fullerene production by Sumio Iijima et al. Have high conductivity, tensile strength, heat resistance, etc. based on their unique structures. Is expected to be used in various fields.
  • CNT carbon nanotubes
  • Non-Patent Document 2 As a method for dissolving carbon nanotubes, a method was proposed in which CNTs were cut short and then chemically modified at both ends (for example, Non-Patent Document 2). It will denature the properties. Recently, the present inventors have found that it is possible to dissolve SCNT such as a specific aromatic compound or DNA (for example, Non-Patent Document 3, Non-Patent Document 4, Patent Document 1). In addition, a method of solubilizing carbon nanotubes using polysaccharides (j8-1, 3, -glucan) (Patent Document 2) and a method of forming aqueous micelles using a surfactant to solubilize (Non Patents) Document 5) is also proposed!
  • SCNT such as a specific aromatic compound or DNA
  • the carbon nanotubes can be solubilized together with the polymer, for example, it is expected that a composite material having an excellent function that has characteristics derived from the polymer in addition to the characteristics of CNT will be obtained.
  • Non-Patent Document 1 S. Iijima, Nature, 354, 56 (1991)
  • Non-Patent Document 2 J. Chen et al., Science, 282, 95 (1998)
  • Non-Patent Document 3 N. Nakashima et al., Trans. Mater. Research Soc. Jpn, 29 525-528 (2004)
  • Non-Patent Document 4 N. Nakashima et al., Chem. Lett. 32,456 (2003)
  • Non-Patent Document 5 R. E. Smalley et al., Science 298, 2361 (2002)
  • Non-Patent Document 6 K. E. Wse et al., Chem. Phys. Lett. 391, 207 (2004)
  • Patent Document 1 Japanese Patent Laid-Open No. 2005-28560
  • Patent Document 2 JP 2005-104762
  • An object of the present invention is to provide a new technology that can contribute to the effective use of carbon nanotubes by unwinding the bundle structure of carbon nanotubes to reliably dissolve the carbon nanotubes. There is to do.
  • the present invention provides a carbon nanotube solubilizing agent comprising an aromatic polyimide having a repeating unit represented by the following general formula [I].
  • AR represents a phenyl group or a condensed polycyclic aromatic group
  • X may or may not exist
  • Z represents a polarity for enhancing solvent solubility.
  • FIG. 1 shows a reaction scheme for synthesizing an example of an aromatic polyimide used in the present invention.
  • FIG. 2 Illustrates the visible near-infrared absorption spectrum of DMNT solution of SWNTZ aromatic polyimide measured in the solubility test of carbon nanotubes according to the present invention.
  • FIG. 3 illustrates an AFM image of SWNTZ polyimide obtained by the present invention.
  • FIG. 4 illustrates the results of two-dimensional mapping of near-infrared photoluminescence measured with a DMSO solution of SWNTZ aromatic polyimide according to the present invention.
  • FIG. 5 illustrates an absorption spectrum measured by mixing another solvent in a DMSO solution of SWNTZ aromatic polyimide according to the present invention.
  • FIG. 6a shows the FT-IR measurement result of one example of polyimide used in the present invention.
  • FIG. 6b shows the measurement result of 1 H-NMR of one example of polyimide used in the present invention.
  • FIG. 7a FT-IR measurement results of another example of polyimide used in the present invention are shown.
  • FIG. 7 b shows the measurement result of 1 H-NMR of another example of polyimide used in the present invention.
  • FIG. 8 shows the FT-IR measurement results of yet another example of the polyimide used in the present invention.
  • FIG. 9a shows the FT-IR measurement results of another example of polyimide used in the present invention.
  • FIG. 9b shows the measurement result of 1 H-NMR of another example of polyimide used in the present invention.
  • FIG. 10 illustrates a visible near infrared absorption spectrum of a DMSO solution of SWNTZ aromatic polyimide measured in a carbon nanotube solubility test according to the present invention.
  • FIG. 11 illustrates a visible near infrared absorption spectrum of an aqueous solution of SWNTZ aromatic polyimide measured in a carbon nanotube solubility test according to the present invention.
  • FIG. 12 illustrates the results of two-dimensional mapping of near-infrared photoluminescence obtained for a DMSO solution of SWNTZ aromatic polyimide according to the present invention.
  • AR represents a phenyl group or a condensed polycyclic aromatic group
  • X represents However, in some cases, when present, it represents an oxygen atom or a sulfur atom
  • Z represents a polar substituent or a nonpolar substituent for increasing the solvent solubility.
  • aromatic group represented by AR include benzene ring, naphthalene ring, anthracene ring, phenanthrene ring, pyrene ring, perylene ring, naphthacene ring, and other such tetravalent functional groups (substituted). May be included).
  • the polar substituent represented by Z is a functional group that imparts solubility to a polar solvent to the polyimide, and preferable examples include a sulfonic acid group, a phosphoric acid group, or Forces including, but not limited to, sulfate groups or their trialkylamine salts.
  • the alkyl of the trialkylamine salt has 1 to 18 carbon atoms, and particularly preferably 1 to 12 carbon atoms.
  • Polyimides of formula [I] having such polar substituents are soluble in polar solvents.
  • the polar solvent is not limited to an aprotic solvent, and may be a protonic polar solvent (eg, water, methanol, ethanol, propanol, butanol, etc.). Sulphoxide (DMSO), dimethylformamide (DMF), m-cresol, and acetonitrile are preferred.
  • a protonic polar solvent eg, water, methanol, ethanol, propanol, butanol, etc.
  • Sulphoxide (DMSO), dimethylformamide (DMF), m-cresol, and acetonitrile are preferred.
  • the aromatic polyimide represented by the formula [I] as an object of the present invention may have a nonpolar substituent as Z.
  • the nonpolar substituent include a force including a long-chain alkyl group having 8 to 18 carbon atoms (which may be branched), but is not limited thereto.
  • Polyimides of formula [I] with such polar substituents are soluble in polar solvents (eg, hexane, benzene, toluene, jetyl ether, black mouth form, etc.).
  • Et represents an ethyl group.
  • FIG. 1 shows a synthesis scheme of an aromatic polyimide composed of repeating units represented by the above formulas [Pl], [P2], [P3], and [P4].
  • m-taresol is used as a solvent, and the starting materials, acid dianhydride and diamine, are added in the presence of triethylamine and benzoic acid at 80 ° C for 4 hours and at 180 ° C for 2 hours.
  • the desired aromatic polyimide is obtained by heating for 0 hour and re-precipitation in acetone for recovery (see Non-Patent Document 7).
  • the molecular weight of the aromatic polyimide thus obtained and used in the present invention is generally about 15000 to 50000.
  • Non-Patent Document 7 J. Fang et al., Macromolecules, 35, 9022 (2002)
  • the aromatic polyimide of the formula [I] is soluble in various solvents at room temperature!
  • the carbon nanotubes can be dissolved as follows. First, the aromatic polyimide is dissolved in a polar or nonpolar solvent as described above. Next, carbon nanotubes are added to the solvent solution of the aromatic polyimide thus obtained. Furthermore, the obtained aromatic polyimide and carbon nanotube solvent solution is irradiated with ultrasonic waves. If necessary, the solution after ultrasonic irradiation is subjected to centrifugal separation, whereby the bundled carbon nanotubes are reliably removed.
  • Another feature of the soluble method according to the present invention using an aromatic polyimide having an aromatic moiety is to selectively dissolve nanotubes of several structures having a specific chiral vector. Is to get.
  • an aromatic polyimide having a repeating unit represented by the above-mentioned formula [P2] is used, a single layer having a chiral index of (8, 6) is different from the case of using a normal surfactant.
  • Carbon nanotubes can be particularly soluble (see Example 4 below). This is presumably because the mechanism of solubilization differs from that in the solubilization method (Non-Patent Document 5) in which a micelle aqueous solution is formed using a surfactant.
  • a solution (solvent solution) or gel composed of aromatic polyimide and carbon nanotubes can be obtained by performing the above-described soluble method.
  • a solution or gel can be directly used for a film forming process or an extrusion molding process.
  • the aromatic polyimide ZCNT solution obtained by the above-described soluble liquefaction operation and CNT is soluble can be obtained by using other solvents such as water, ethanol, and acetonitrile. It can be mixed with polar solvents and individual CNTs remain dissolved independently when diluted with those solvents (see Example 5 below). Therefore, it is possible to prepare a composite system in which, for example, a soluble component is added to these solvents, using this property.
  • carbon nanotubes include single-walled carbon nanotubes (abbreviated as SWCNT or SWNT) and multi-walled nanotubes (abbreviated as MWCNT or MWNT).
  • SWCNT single-walled carbon nanotubes
  • MWCNT multi-walled nanotubes
  • the principle of the present invention can be applied to multi-walled nanotubes, but is particularly suitable for single-walled carbon nanotubes.
  • Carbon nanotubes” or “CNTs” as used in connection with the present invention shall refer primarily to single-walled carbon nanotubes.
  • Carbon nanotubes Purified SWNT (HiPco) Purchased from Carbon Nanotechnologies Co. Ultraviolet Visible Near-infrared absorption spectrum measurement: Spectrophotometer JASCO, V-570.
  • Example 2 Using the aromatic polyimide synthesized in Example 1, a solubility test of carbon nanotubes was performed. Each aromatic polyimide was dissolved in DMSO to prepare a DMSO solution having a concentration of 1 mg / mL of each aromatic polyimide. Purified SWNT was added to this DMSO solution and subjected to ultrasonic treatment for 15 minutes. After visual observation and measurement of the absorption spectrum, the same operation was repeated by increasing the concentration of SWNT. The concentration of SWNT was in the range of 0.1 to about 3 mg / mL (to polyimide weight ratio 0.1 to 3).
  • Fig. 2 shows the visible and near-infrared absorption spectrum measured during the solubility test conducted using P2 polyimide.
  • Measurement of the near-infrared absorption spectrum is one of means for indicating the presence of carbon nanotubes in which a bundle structure is unwound and dissolved individually in a solution or dispersion system (Non-patent Document 8).
  • Non-patent Document 8 the solubilization of carbon nanotubes using the wholly aromatic polyimide according to the present invention is characterized by the individual dissolution of SWNTs over a wide concentration range of SWNTs.
  • the spectrum is observed in the near infrared region. That is, for the viscous solution (spectrum b in Fig. 2) and gel (spectrum c in Fig. 2), the waveform and peak position of the spectrum measured by the solution with the low concentration of SWNT (spectrum a in Fig.
  • a SWNT solution with a bundle structure can be obtained in water even in water, and this is, for example, the visible-near infrared absorption of P4 polyimide ZS WNT aqueous solution.
  • the spectrum (Fig. 11) is obvious.
  • Non-Patent Document 8 R. E. Smalley et al., Science 297, 593 (2002)
  • FIG. 3 shows an AFM image when P2 aromatic polyimide is used.
  • the SWNT has a diameter of 95% or more in the range of 0.7 to 2.0 nm, and it is shown that most SWNTs exist in the dissolved state. According to the near-infrared absorption spectrum of Example 2. It agrees with the result.
  • a near-infrared photoluminescence two-dimensional mapping was determined for the DMSO solution of SWNTZ aromatic polyimide obtained in Example 2.
  • Fig. 4 shows the results when P2 aromatic polyimide is used
  • Fig. 12 shows the results when P4 aromatic polyimide is used. Samples were prepared by subjecting the solution to centrifugation at 10000 g for 3 hours.
  • SWNT As shown in FIG. 4, the presence of (8, 6), (9, 5), (12, 1) (14, 0) and (14, 9) SWNTs was observed, (8, 6 ) SWNT is particularly strong. Also, from Fig. 11, P4's polyimide has (7, 6), (9, 4), (8, 6), (8, 7), (9, 5) and (10, 5) chirality. It is understood that SWNTs with sol are dissolved in isolation. These are different from SWNT (Non-Patent Document 5), which is present in micellar aqueous solution when the surfactant SDS (sodium dodecyl sulfate) is used, and the carbon nanotubes according to the present invention proceed by a unique mechanism. It is guessed.
  • SDS sodium dodecyl sulfate
  • Fig. 5 shows the results of an absorption spectrum measurement when water is mixed in a DMSO solution of SWNTZ polyimide using P1 aromatic polyimide.
  • (a) is the stock solution before mixing
  • the absorption spectrum No substantial change was observed, and it was confirmed that even when the soluble solution was diluted with water, SWNTs were dissolved individually. By visual observation, the SWNTs remained soluble evenly. Similar results were obtained when diluted with acetonitrile or ethanol.
  • the aromatic polyimide synthesized in Example 1 was protonated to convert the triethylamine salt moiety into a sulfonic acid group. Protony was performed by immersing P1 and P2 membranes washed in hot methanol in 1N hydrochloric acid for 8-12 hours, washing with ultrapure water, and drying.
  • the polyimide obtained by protonating P1 and P2 still maintained solubility in DMSO. Therefore, a solubilization test of SWNT was performed using protonated P1 and P2 DMSO solutions according to the same method as in Example 2, and a visible and near infrared absorption spectrum was measured. Even when using a protonated polyimide, SWNTs can be solubilized in the same manner as with P1 and P2, and substantially the same absorption spectrum can be obtained, and triethylamine salts of P1 and P2 can be obtained. It was understood that the structure did not affect the solubility.

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  • Organic Chemistry (AREA)
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  • Compositions Of Macromolecular Compounds (AREA)
  • Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
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Abstract

La présente invention concerne une technique permettant de délier la structure en gerbe d'un nanotube de carbone afin de solubiliser complètement le nanotube de carbone, cette technique étant particulièrement utile pour une utilisation efficace d'un nanotube de carbone. La technique décrite dans cette invention se caractérise par l'utilisation d'un polyimide aromatique présentant une unité récurrente représentée par la formule générale [I]: [I] dans cette formule, AR représente un groupe phényle ou un groupe aromatique polycyclique hybride; X peut être présent ou absent et, lorsqu'il est présent, X représente un atome d'oxygène ou de soufre; et Z représente un substituant polaire ou non polaire permettant d'augmenter la solubilité d'un solvant. Le polyimide est dissous dans un solvant polaire ou non polaire, un nanotube de carbone est ajouté à la solution de polyimide dans le solvant, puis la solution de polyimide et le nanotube de carbone dans le solvant sont exposés à un rayonnement d'ondes ultrasonores, ce qui permet de solubiliser le nanotube de carbone.
PCT/JP2006/321962 2005-11-04 2006-11-02 Solubilisation de nanotube de carbone au moyen de polyimide aromatique Ceased WO2007052739A1 (fr)

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Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010131421A1 (fr) * 2009-05-11 2010-11-18 東洋紡績株式会社 Procédé de production d'un film en polybenzoxazole
WO2011055776A1 (fr) * 2009-11-06 2011-05-12 学校法人 芝浦工業大学 Procédé de fabrication d'un gel contenant un matériau nanocarboné
JP2012055814A (ja) * 2010-09-07 2012-03-22 Chiba Univ 機能性可溶化剤
JP2013177295A (ja) * 2012-01-31 2013-09-09 Shibaura Institute Of Technology ナノカーボン材料含有ゲルの製造方法
WO2016080327A1 (fr) * 2014-11-17 2016-05-26 ニッタ株式会社 Dispersion de nanotubes de carbone (cnt), film fonctionnel, et matériau composite
JPWO2021033482A1 (fr) * 2019-08-19 2021-02-25
WO2025206316A1 (fr) * 2024-03-29 2025-10-02 Ｕｂｅ株式会社 Dispersion aqueuse à teneur en acide polyamique / nanotubes de carbone

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JP6155339B2 (ja) * 2013-08-29 2017-06-28 住友理工株式会社 柔軟導電材料およびトランスデューサ

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JP2005028560A (ja) * 2003-07-07 2005-02-03 Naotoshi Nakajima Ｄｎａおよびオリゴヌクレオチドを用いる水溶性カーボンナノチューブの製造方法

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Cited By (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010131421A1 (fr) * 2009-05-11 2010-11-18 東洋紡績株式会社 Procédé de production d'un film en polybenzoxazole
CN102421825A (zh) * 2009-05-11 2012-04-18 东洋纺织株式会社 聚苯并噁唑膜的制造方法
JP5707320B2 (ja) * 2009-05-11 2015-04-30 東洋紡株式会社 ポリベンズオキサゾールフィルムの製造方法
WO2011055776A1 (fr) * 2009-11-06 2011-05-12 学校法人 芝浦工業大学 Procédé de fabrication d'un gel contenant un matériau nanocarboné
JP5747354B2 (ja) * 2009-11-06 2015-07-15 学校法人 芝浦工業大学 ナノカーボン材料含有ゲルの製造方法
US9419235B2 (en) 2009-11-06 2016-08-16 Shibaura Institute Of Technology Method for producing gel containing nano-carbon material
JP2012055814A (ja) * 2010-09-07 2012-03-22 Chiba Univ 機能性可溶化剤
JP2013177295A (ja) * 2012-01-31 2013-09-09 Shibaura Institute Of Technology ナノカーボン材料含有ゲルの製造方法
JP2016094323A (ja) * 2014-11-17 2016-05-26 ニッタ株式会社 カーボンナノチューブ分散液、機能性膜および複合素材
WO2016080327A1 (fr) * 2014-11-17 2016-05-26 ニッタ株式会社 Dispersion de nanotubes de carbone (cnt), film fonctionnel, et matériau composite
JPWO2021033482A1 (fr) * 2019-08-19 2021-02-25
WO2021033482A1 (fr) * 2019-08-19 2021-02-25 Jsr株式会社 Composition de dispersion, dispersant, film anisotrope et son procédé de production, et appareil de formation de film anisotrope
CN114026178A (zh) * 2019-08-19 2022-02-08 Jsr株式会社 分散组合物、分散剂、各向异性膜及其制造方法、以及各向异性膜形成装置
CN114026178B (zh) * 2019-08-19 2024-01-30 Jsr株式会社 分散组合物、分散剂、各向异性膜及其制造方法、以及各向异性膜形成装置
TWI864056B (zh) * 2019-08-19 2024-12-01 日商Ｊｓｒ股份有限公司 分散組成物、分散劑、各向異性膜及其製造方法、以及各向異性膜形成裝置
JP7730760B2 (ja) 2019-08-19 2025-08-28 Jsr株式会社 分散組成物、分散剤、異方性膜及びその製造方法、並びに異方性膜形成装置
WO2025206316A1 (fr) * 2024-03-29 2025-10-02 Ｕｂｅ株式会社 Dispersion aqueuse à teneur en acide polyamique / nanotubes de carbone

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