WO2002088025A1 - Method for dissolving carbon nanotubes - Google Patents
Method for dissolving carbon nanotubes Download PDFInfo
- Publication number
- WO2002088025A1 WO2002088025A1 PCT/US2002/013193 US0213193W WO02088025A1 WO 2002088025 A1 WO2002088025 A1 WO 2002088025A1 US 0213193 W US0213193 W US 0213193W WO 02088025 A1 WO02088025 A1 WO 02088025A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- nanotubes
- group
- carbon nanotubes
- electron donor
- donor compound
- Prior art date
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Classifications
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01J—ELECTRIC DISCHARGE TUBES OR DISCHARGE LAMPS
- H01J9/00—Apparatus or processes specially adapted for the manufacture, installation, removal, maintenance of electric discharge tubes, discharge lamps, or parts thereof; Recovery of material from discharge tubes or lamps
- H01J9/02—Manufacture of electrodes or electrode systems
- H01J9/022—Manufacture of electrodes or electrode systems of cold cathodes
- H01J9/025—Manufacture of electrodes or electrode systems of cold cathodes of field emission cathodes
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- B82Y10/00—Nanotechnology for information processing, storage or transmission, e.g. quantum computing or single electron logic
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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
- B82Y30/00—Nanotechnology for materials or surface science, e.g. nanocomposites
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
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- B82Y40/00—Manufacture or treatment of nanostructures
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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
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/005—Reinforced macromolecular compounds with nanosized materials, e.g. nanoparticles, nanofibres, nanotubes, nanowires, nanorods or nanolayered materials
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/20—Carbon compounds, e.g. carbon nanotubes or fullerenes
- H10K85/221—Carbon nanotubes
-
- 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
- C01B2202/02—Single-walled nanotubes
-
- 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
- C01B2202/06—Multi-walled nanotubes
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01J—ELECTRIC DISCHARGE TUBES OR DISCHARGE LAMPS
- H01J2201/00—Electrodes common to discharge tubes
- H01J2201/30—Cold cathodes
- H01J2201/304—Field emission cathodes
- H01J2201/30446—Field emission cathodes characterised by the emitter material
- H01J2201/30453—Carbon types
- H01J2201/30469—Carbon nanotubes (CNTs)
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K30/00—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation
- H10K30/30—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation comprising bulk heterojunctions, e.g. interpenetrating networks of donor and acceptor material domains
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K30/00—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation
- H10K30/50—Photovoltaic [PV] devices
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P70/00—Climate change mitigation technologies in the production process for final industrial or consumer products
- Y02P70/50—Manufacturing or production processes characterised by the final manufactured product
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S977/00—Nanotechnology
- Y10S977/84—Manufacture, treatment, or detection of nanostructure
- Y10S977/842—Manufacture, treatment, or detection of nanostructure for carbon nanotubes or fullerenes
- Y10S977/845—Purification or separation of fullerenes or nanotubes
Definitions
- the present invention provides a method for dissolving nanostructured materials such as carbon nanotubes and solutions for carbon nanotubes.
- Nanostructured materials such as carbon nanotubes (NTs) have been the subject of much research in recent years because their unique electronic, mechanical and physical properties can be used in all areas of science. 1 ' 2 Nanostructured tubes are becoming increasingly important because their mechanical properties, notably strength, stiffness, and toughness, make them useful in a variety of applications. Composites made from carbon nanotubes have superior strength and stiffness per weight, and thus are already being used in aerospace and sporting goods applications. Carbon nanotubes are also excellent electron emitters, emitting electrons at very low voltage, which makes them particularly useful in the field of flat panel displays. Their good electron conductivity and high thermal conductivity also make carbon nanotubes ideal materials for making antistatic and/or anti-corrosion coatings as well as thermal conductors. Additionally, carbon nanotubes can be used in electronic circuits where silicon and other standard semiconductor materials do not work.
- Carbon nanotubes are particularly stable because of the strength with which the carbon atoms bond together.
- the carbon atoms arrange themselves in hexagonal rings, similar to the arrangement in graphite.
- a nanotube resembles a sheet or several stacked sheets of graphite rolled into a seamless cylinder.
- carbon nanotubes are difficult to dissolve or disperse in most organic or inorganic solvents because of their long structured features, large molecular size, or severe aggregation.
- the common agents used to help disperse carbon nanotubes are surfactants, which, however, can only increase the dispersibility to a limited extent, and surfactants do not affect the solubility of carbon nanotubes.
- nanotube materials can be dissolved in a variety of solvents by treating carbon nanotubes with an electron donor, such as an aromatic amine.
- the electron donor acts to solubilize the nanotubes in the solvents.
- the carbon nanotubes can be readily dissolved in other polar or nonpolar organic solvents, including but not limited to solvents such as chloroform, acetone, toluene, benzene, methanol, ethanol, DMF, TMF, and the like.
- solvents such as chloroform, acetone, toluene, benzene, methanol, ethanol, DMF, TMF, and the like.
- Figure 1 is an SEM picture of dissolved carbon nanotubes after solvent evaporation.
- Figure 2A shows the UN-visible absorption spectra of a solution of carbon nanotubes dissolved in aniline.
- 2B shows the absorbance of an aniline solution of carbon nanotubes diluted with acetone.
- Figure 3 shows the emission spectra of carbon nanotubes in aniline in different solvents.
- Nanostructured materials such as carbon nanotubes can be dissolved in polar or nonpolar organic solvents using small electron donor molecules as solubilizers.
- Aromatic amines are among the preferred electron donor molecules.
- the nanostructured materials used can be nano carbon materials, such as carbon nanotubes, either single- or multi-walled, pristine or chemically functionalized.
- the aromatic amine compounds which solubilize nanotubes comprise at least one amino group and at least one phenyl ring.
- the amino group can be a primary, secondary, or tertiary amino group.
- the phenyl ring can be substituted or substituted by other functional groups.
- Preferred substituents on the phenol ring are electron donor groups such as Ci-Cio alkyl.
- the preferred amines have the following structure:
- R H, -CH 3 . -CH 2 CH 3 , -fa -OH, -NH, - SH , -NH2 etc
- R can be hydrogen, Ci-Cio, phenyl, hydroxyi, primary or secondary amino, thio, etc. including -SH or -SR, wherein R is an aryl group; selino, either -SeH or -SeR, wherein R can be an aryl group.
- any one of R can be selected from the following:
- N- substituted aromatic amines wherein either one or two of the hydrogen on the ring is substituted by an aromatic group such as phenyl, or a C1-C12 alkyl group, either straight chain or branched, saturated or unsaturated.
- aromatic group such as phenyl, or a C1-C12 alkyl group, either straight chain or branched, saturated or unsaturated.
- the following compounds illustrate such electron donors: (N substituted aromatic amines, either one or two of H substituted by no ⁇ or aromatic groups -CH2CH3, -Ar, etc)
- Additional compounds which can be used as electron donors to dissolve nanotubes include aromatic amines in which there is substitution in the benzene ring, alone or together with N substitution by aromatic or nonaromatic hydrocarbon groups.
- These hydrocarbon groups can have from 1 to 12 carbon atoms, and can be aryl, saturated, or unsaturated, branched chain or straight chain. Examples of these compounds are as follows :
- solubilizing agents are amines
- other solvents with different aromatic and heterocyclic ring structures may also function as electron donor solvents.
- the electron donors can be either in a solid or a liquid state.
- the amine group can be attached to any type of heterocyclic aromatic ring, including fused rings with more than one heterocyclic atom, as illustrated by the following compounds :
- the heterocycle atoms can be N, S, Se, 0, or P.
- the dissolution process can be facilitated significantly by applying an exogenous energy source to a mixture of carbon nanotubes and the electron donor compounds.
- the energy sources can include heating, mechanical stirring, ultra-sonification, microwave irradiation, or any combination thereof.
- the resulting solution can be mixed with polymers, for example, polyolifins such as polyethylene, polyvinyl chloride, polytetrafluoroethylene, polyacrylonitrile, polymethyl methacrylate, polyvinyl acetate, polyester, polystyrene, polyamide, and the like, to form nanocomposites .
- the solutions of nanotubes can be coated onto a substrate and the solvent removed by conventional means to form a coating or layer of nanotubes.
- SWNT Single-walled carbon nanotubes
- 2 Multi-walled nanotubes were purchased from Nanocs Inc., New York.
- 40 mg of accurately weighed NTs were added to 5 mL aniline and the mixture was heated at reflux for 3 hours in the dark. Dissolution of carbon nanotubes in aniline was observed by the color change of the solution after reflux for a short time. Thus, with continuous heating, the original colorless aniline solution first became brownish and then turned dark red.
- Carbon nanotubes from tubes from Rice University were dispersed in toluene and 10 mL of this dispersion was placed into a 100 mL flask. 20 mL of aniline was added, and the mixture was heated at reflux for two hours. The resulting browning solution was filtered through 2 micrometer PTEE filter paper, and the nanotube solution was collected.
- Example 4 Carbon nanotubes from tubes from Rice University were dispersed in toluene and 10 mL of this dispersion was placed into a 100 mL flask. 20 mL of aniline was added, and the mixture was heated at reflux for two hours. The resulting browning solution was filtered through 2 micrometer PTEE filter paper, and the nanotube solution was collected.
- Figure 2A shows the UN-Vis absorption spectra of the SW ⁇ T-aniline diluted with acetone solution. Absorption between 310-400 nm is very strong while a new peak at 530 nm suggests the formation of an aniline-SW ⁇ T charge-transfer complex. In very dilute solution, the broad peak between 310- 400 n can be resolved into two sharp peaks at 325 nm and 375 nm respectively, while the peak at 530 nm is no longer observed.
- C6o has been shown to form donor-acceptor complexes in the liquid state when dissolved in tertiary amines and substituted anilines.
- the room temperature solubility of Cs 0 in aniline, W-methylaniline, and N, ZV-dimethyl aniline was found to be 1.05, 1.16, and 3.89 mg/mL, respectively.
- 10"12 Complexation with aniline has also been applied to separate Ceo from various endohedral complexes.
- 13 C 6 o also showed reactivity in the ground state with various primary, secondary and tertiary amines, attributed to electron transfer from the amines to the fullerene.
- NT should be a good electron acceptor, 4 '' while aniline is a fairly good electron donor.
- aniline may form a charge transfer complex in its ground state, as evidenced by the appearance of new absorption in the visible region ( Figure 2) .
- This may be followed by proton transfer from aniline to the fullerene, (see Scheme 1) .
- the NT-aniline complex (or adduct) is quite stable, even after three months, as shown by the persistence of the new spectral features. In contrast, no measurable dissolution of carbon nanotubes was observed in nitrobenzene, an electron acceptor.
- Luminescence has been observed 4 at slightly longer wavelengths for polymer-bound (i.e., NTs covalently linked to poly- (propionylethylenimine-co- ethylenimine) .
- the quantum yield for our NT-aniline solutions are also higher than that for the polymer-bound NTs. 4
- precautions were taken to prevent interference from fluorescence of small aromatic species and other impurities. 4
- a solution of carbon nanotubes and an electron donor compound is mixed with an appropriate fluorescent or luminescent polymer.
- a fluorescent substance is one that absorbs radiant energy of certain wavelengths and, after a fleering instant, gives off part of the absorbed energy as quanta of longer wavelengths.
- Most fluorescent pigments are of the toluenesulfonamide-melamine-formaldehyde resin matrix type. A mixture of o- and p- toluenesulfonamide, paraformaldehdye, and a B-stage unmodified melamine- for aldehyde resin is heated together.
- Fluorescent dyes such as Rhodamine F3B, Rhodamine 6GDN, or Brilliant Yellow 6G Base are added along with a dispersion or solution of carbon nanotubes and an electron emitting molecule, and heating continued.
- the finished colored resin is clear, brittle, and friable, and can be pulverized by impact milling to a fine powder, which is the final fluorescent pigment which can be used in a wide variety of applications.
- the presence of the carbon nanotubes imparts superior fluorescence to the pigment.
- the use of the electron donor compound makes it possible to disperse the carbon nanotubes uniformly in the polymer composition so that a uniform pigment is produced.
- Figure 3 Emission spectra of SWNT-aniline in different solvents. Solid line: acetone; dashed line: toluene; dotted line: methanol. Excitation of all solutions at 500 nm.
- the present invention provides a simple, economical way to disperse or dissolve nanotube materials in solvents so that the nanotube materials can be used in a variety of applications.
- the nanotubes in solution or dispersion form can be coated onto substrates or mixed into a variety of other materials, including polymers, to form composites with outstanding characteristics.
- a high-current field emitter can be made by forming a dispersion of nanotubes as described in the above examples and mixing the dispersion into a composite paste with suitable polymeric resins. This paste is then smeared onto an electrode. When voltage is applied, some of the nanotubes in the layer point toward the opposite electrode and emit electrons.
- An electron emitter composition according to one embodiment of the present invention comprises carbon nanotubes as electron emitting materials.
- the composition also comprises a binder, dispersing agent, and water.
- the amount of the electron emitting material is preferably 1 to 50% by weight, more preferably 5 to 30% by weight, and most preferably 10 to 20% by weight, of the total composition.
- nanotubes are dispersed in a dispersion agent such as polyoxyethylene nonyl phenyl ether derivative, polyvinylpyrrolidone, etc., with the aid of an electron donor molecule as described above.
- a dispersion agent such as polyoxyethylene nonyl phenyl ether derivative, polyvinylpyrrolidone, etc.
- This mixture is then added to a binding composition, such as a silane based compound or colloidal silica, and the composition is bound to a cathode electrode made of silver, ITO, etc. Water can be used as the dispersion medium. Additional details of this production, with the exception of dispersion of the nanotubes with an electron donor molecule, can be found in Jin et al . , U.S.
- Patent No: 6,250,984 the entire contents of which are hereby incorporated by reference.
- the use of an electron donor compound to disperse the nanotubes provides improved dispersion so that a more uniform device can be prepared.
- nanotube solutions can be used for the formation of nano-composites or cast into thin films, which would solve the practical problems involved in making nanotube-based electronic and field emission display devices. 17
- the strong fluorescence emission of carbon nanotubes should also be a useful probe in elucidation of the physical and biological properties of these materials.
- the process of the present invention makes it possible to manipulate nanotubes in order to produce desirable electronic and other types of devices.
- Nanotubes can be attached to chips to draw away heat, allowing them to run cooler. Additionally, as the transistors become smaller, so do the thin metal wires connecting them, making them more likely to break. Nanotubes can be used as replacement wires, as they are much stronger and thinner than metal wires .
- Nanotubes can be formed from condensed carbon vapor, and they are only 1/50, 000th as thick as a human hair.
- the carbon rings of the nanotube line up with the main axis of the nanotube, the nanotube conducts electricity as well as a metal.
- the pattern of hexagonal rings in a nanotube is twisted, the nanotube acts like a semiconductor, i.e., it conducts electricity only after a certain threshold.
- Nanotubes dissolved or dispersed with the aid of an electron donor molecule can readily be used to fabricate electron emitting sources such as described in Uemura et al., U.S. Patent No. 6,239,547, the entire contents of which are hereby incorporated by reference.
- This electron emitting source is produced from carbon nanotubes formed from a columnar graphite layer in which a plurality of carbon nanotubes aggregate to form a needle-like structure.
- the electron-emitting source can be made by recessing a substrate and filling the recess with a solution or dispersion of carbon nanotubes which have been dissolved or dispersed with the aid of an electron donor molecule.
- a paste is formed by dispersing the carbon nanotubes in a conductive viscous solution with the aid or an electron donor molecule.
- This paste is used to form a pattern on a substrate.
- the use of the electron donor molecule makes it easy to disperse the nanotubes in the conductive solution so that the nanotubes are distributed evenly in the pattern.
- nanotubes can be added to plastics to make the resin electrically conductive. Because the present invention makes it possible to dissolve or disperse nanotubes, the nanotubes can readily be evenly distributed throughout a resin composition. Alternatively, nanotubes can- be incorporated into plastics to make them antistatic, or for use in EMI shielding.
- Nonlimiting examples of such polymers include epoxy resins, polyolefins, polyvinylchloride, polyacrylinitrile, polymethyl methacrylate, polyvinyl acetate, polyester, polystyrene, polyamide, and mixtures and copolymers thereof.
- nanotubes are about 100 times as strong as steel, they are too small to use as individual fibers. However, they can be assembled into bits of "rope”. Being able to disperse the nanotubes evenly by the process of the present invention makes it much easier to assemble the nanotube "ropes.”
- Self-oriented bundles of carbon nanotubes such as those disclosed in Dai et al . , U.S. Patent No. 6,232,706, the entire contents of which are hereby incorporated by reference, can be produced from carbon nanotubes which have been dispersed or dissolved in a fluid using an electron donor molecule.
- a silicon substrate is electrochemically etched to form a thin nanoporous layer on top of a macroporous layer.
- a dispersion or solution of carbon nanotubes with an electron donor molecule is deposited in a predetermined pattern on the substrate. This deposition is repeated until the carbon naotubes are deposited on the substrate in sufficient quantity to produce a superior field emission device.
- the treated carbon nanotubes according to the present invention have much stronger light emission properties than untreated carbon nanotubes.
- Nanotubes of differing sizes and configurations can be more easily separated after dissolution. The dissolved carbon nanotubes are applied to gel chro atography (gel permeation, affinity, or size exclusion) and eluted with different solvents. Because of the structural differences among different nanotubes, the ability to bind with the gel will differ, and the tubes can be washed out with common solvents .
- Solutions of carbon nanotubes can be used to produce a variety of products incorporating carbon nanotubes as described above.
- solutions of carbon nanotubes can be used in making devices as described in the following U.S. patents, the entire contents of which are hereby incorporated by reference:
Abstract
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Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5505879A (en) * | 1991-07-15 | 1996-04-09 | E. I. Du Pont De Nemours And Company | Charge transfer complexes |
US6019656A (en) * | 1997-11-29 | 2000-02-01 | Electronics And Telecommunications Research Institute | Method of fabricating a field emission device by using carbon nano-tubes |
US6187823B1 (en) * | 1998-10-02 | 2001-02-13 | University Of Kentucky Research Foundation | Solubilizing single-walled carbon nanotubes by direct reaction with amines and alkylaryl amines |
Family Cites Families (18)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB9418937D0 (en) | 1994-09-20 | 1994-11-09 | Isis Innovation | Opening and filling carbon nanotubes |
US5866434A (en) | 1994-12-08 | 1999-02-02 | Meso Scale Technology | Graphitic nanotubes in luminescence assays |
WO1997019208A1 (en) | 1995-11-22 | 1997-05-29 | Northwestern University | Method of encapsulating a material in a carbon nanotube |
US5640705A (en) | 1996-01-16 | 1997-06-17 | Koruga; Djuro L. | Method of containing radiation using fullerene molecules |
US5800706A (en) | 1996-03-06 | 1998-09-01 | Hyperion Catalysis International, Inc. | Nanofiber packed beds having enhanced fluid flow characteristics |
US6231744B1 (en) | 1997-04-24 | 2001-05-15 | Massachusetts Institute Of Technology | Process for fabricating an array of nanowires |
EP1361592B1 (en) | 1997-09-30 | 2006-05-24 | Noritake Co., Ltd. | Method of manufacturing an electron-emitting source |
US6087765A (en) | 1997-12-03 | 2000-07-11 | Motorola, Inc. | Electron emissive film |
US6203864B1 (en) | 1998-06-08 | 2001-03-20 | Nec Corporation | Method of forming a heterojunction of a carbon nanotube and a different material, method of working a filament of a nanotube |
US6146230A (en) | 1998-09-24 | 2000-11-14 | Samsung Display Devices Co., Ltd. | Composition for electron emitter of field emission display and method for producing electron emitter using the same |
US6232706B1 (en) | 1998-11-12 | 2001-05-15 | The Board Of Trustees Of The Leland Stanford Junior University | Self-oriented bundles of carbon nanotubes and method of making same |
US6250984B1 (en) | 1999-01-25 | 2001-06-26 | Agere Systems Guardian Corp. | Article comprising enhanced nanotube emitter structure and process for fabricating article |
US6265466B1 (en) | 1999-02-12 | 2001-07-24 | Eikos, Inc. | Electromagnetic shielding composite comprising nanotubes |
US6361861B2 (en) | 1999-06-14 | 2002-03-26 | Battelle Memorial Institute | Carbon nanotubes on a substrate |
US6277318B1 (en) | 1999-08-18 | 2001-08-21 | Agere Systems Guardian Corp. | Method for fabrication of patterned carbon nanotube films |
US6062931A (en) | 1999-09-01 | 2000-05-16 | Industrial Technology Research Institute | Carbon nanotube emitter with triode structure |
US6256996B1 (en) | 1999-12-09 | 2001-07-10 | International Business Machines Corporation | Nanoscopic thermoelectric coolers |
US6783746B1 (en) * | 2000-12-12 | 2004-08-31 | Ashland, Inc. | Preparation of stable nanotube dispersions in liquids |
-
2002
- 2002-04-26 US US10/132,387 patent/US7250569B2/en not_active Expired - Fee Related
- 2002-04-26 WO PCT/US2002/013193 patent/WO2002088025A1/en not_active Application Discontinuation
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5505879A (en) * | 1991-07-15 | 1996-04-09 | E. I. Du Pont De Nemours And Company | Charge transfer complexes |
US6019656A (en) * | 1997-11-29 | 2000-02-01 | Electronics And Telecommunications Research Institute | Method of fabricating a field emission device by using carbon nano-tubes |
US6187823B1 (en) * | 1998-10-02 | 2001-02-13 | University Of Kentucky Research Foundation | Solubilizing single-walled carbon nanotubes by direct reaction with amines and alkylaryl amines |
Non-Patent Citations (7)
Title |
---|
AGO H ET AL: "COMPOSITES OF CARBON NANOTUBES AND CONJUGATED POLYMERS FOR PHOTOVOLTAIC DEVICES", ADVANCED MATERIALS, VCH VERLAGSGESELLSCHAFT, WEINHEIM, DE, vol. 11, no. 15, 20 October 1999 (1999-10-20), pages 1281 - 1285, XP000869420, ISSN: 0935-9648 * |
AUSMAN K D ET AL: "Organic solvent dispersions of single-walled carbon nanotubes: toward solutions of pristine nanotubes", JOURNAL OF PHYSICAL CHEMISTRY. B, MATERIALS, SURFACES, INTERFACES AND BIOPHYSICAL, WASHINGTON, DC, US, vol. 104, no. 38, 28 September 2000 (2000-09-28), pages 8911 - 8915, XP002206260, ISSN: 1089-5647 * |
COCHET, MURIELLE ET AL: "Synthesis of a new polyaniline/nanotube composite: "in-situ" polymerisation and charge transfer through site-selective interaction", CHEMICAL COMMUNICATION, no. 16, 2001, pages 1450 - 1451, XP002212790 * |
HAMON M A ET AL: "DISSOLUTION OF SINGLE-WALLED CARBON NANOTUBES", ADVANCED MATERIALS, VCH VERLAGSGESELLSCHAFT, WEINHEIM, DE, vol. 11, no. 10, 9 July 1999 (1999-07-09), pages 834 - 840, XP000865122, ISSN: 0935-9648 * |
JIAN CHEN ET AL: "Solution properties of single-walled carbon nanotubes", SCIENCE, AMERICAN ASSOCIATION FOR THE ADVANCEMENT OF SCIENCE,, US, vol. 282, 2 October 1998 (1998-10-02), pages 95 - 98, XP002186144, ISSN: 0036-8075 * |
SUN, YI ET AL: "High dissolution and strong light emission of carbon nanotubes in aromatic amine solvents", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2001), 123(22), 5348-5349, XP002212789 * |
VIGOLO B ET AL: "MACROSCOPIC FIBERS AND RIBBONS OF ORIENTED CARBON NANOTUBES", SCIENCE, AMERICAN ASSOCIATION FOR THE ADVANCEMENT OF SCIENCE,, US, vol. 290, no. 290, 17 November 2000 (2000-11-17), pages 1331 - 1334, XP008004074, ISSN: 0036-8075 * |
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