KR101267316B1 - Separation method of carbon nanotube - Google Patents
Separation method of carbon nanotube Download PDFInfo
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- KR101267316B1 KR101267316B1 KR1020100036705A KR20100036705A KR101267316B1 KR 101267316 B1 KR101267316 B1 KR 101267316B1 KR 1020100036705 A KR1020100036705 A KR 1020100036705A KR 20100036705 A KR20100036705 A KR 20100036705A KR 101267316 B1 KR101267316 B1 KR 101267316B1
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82B—NANOSTRUCTURES FORMED BY MANIPULATION OF INDIVIDUAL ATOMS, MOLECULES, OR LIMITED COLLECTIONS OF ATOMS OR MOLECULES AS DISCRETE UNITS; MANUFACTURE OR TREATMENT THEREOF
- B82B3/00—Manufacture or treatment of nanostructures by manipulation of individual atoms or molecules, or limited collections of atoms or molecules as discrete units
- B82B3/0061—Methods for manipulating nanostructures
- B82B3/0071—Sorting nanostructures
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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
- B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- 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
- C01B32/172—Sorting
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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
- C01B2202/00—Structure or properties of carbon nanotubes
- C01B2202/20—Nanotubes characterized by their properties
- C01B2202/22—Electronic properties
Abstract
The present invention relates to a method for separating semiconducting carbon nanotubes and metallic carbon nanotubes by utilizing the fact that the magnetic nanoparticles surface-modified with an amine group or the like selectively bond with the carboxyl groups of the semiconducting carbon nanotubes. As such, it can be separated without additional expensive equipment.
Description
The present invention relates to a method for separating semiconducting carbon nanotubes and metallic carbon nanotubes using magnetic nanoparticles.
Carbon nanotubes have excellent mechanical and electrical properties. For this reason, the carbon nanotubes can be used in a wide range of fields such as electron source materials and conductive resin materials. In particular, since single-walled carbon nanotubes (SWNTs) have excellent electronic properties, the use of these properties is strongly desired.
The single-walled carbon nanotubes have a diameter of several nm, lengths of several tens of nm to several cm, and have walls corresponding to one atomic layer thickness. Such single-walled carbon nanotubes have the properties of semi-conducting (sc-SWNTs) or metallic (met-SWNTs) according to chirality, and conventionally synthesized single-walled carbon nanotubes have about 70% semiconducting single-walled carbon. It consists of nanotubes and 30% metallic single-walled carbon nanotubes.
Therefore, for practical application of single-walled carbon nanotubes, mass separation of semiconducting single-walled carbon nanotubes and metallic single-walled carbon nanotubes must be preceded.
To solve this problem, various methods for separating semiconducting single-walled carbon nanotubes and metallic single-walled carbon nanotubes have been developed. Examples are alternating dielectric electrophoresis, selective oxidation, amine group extraction, aromatic extraction, polymer wrapping, density gradient fast centrifugation, and the use of a surfactant called ODA (octadecylamine). However, the above method has a problem in that it is difficult to separate single-walled carbon nanotubes in large quantities, or a high separation cost is required. In addition, the single-walled carbon nanotubes have a problem in that they are difficult to be practical because they have low dispersibility (agglomeration due to bundle phenomenon).
The present invention provides a method for separating semiconducting carbon nanotubes and metallic carbon nanotubes by utilizing the fact that the magnetic nanoparticles surface-modified with functional groups such as amine groups selectively bond with the carboxyl groups of the semiconducting carbon nanotubes. For the purpose of
The present invention provides a means for solving the above problems, comprising: mixing a carbon nanotube solution containing a carbon nanotube formed with a functional group on the surface and the magnetic nanoparticles surface-modified with a functional group capable of covalently bonded to the functional group; And
It provides a method for separating carbon nanotubes comprising the step of separating the semiconducting carbon nanotubes and metallic carbon nanotubes by applying a magnetic field to the mixture prepared by the above step.
In another aspect, the present invention provides a composition comprising a carbon nanotube formed with a functional group on the surface and magnetic nanoparticles surface-modified with a functional group capable of covalently bonded to the functional group.
In the present invention, there is an advantage that the semiconductor carbon nanotubes and the metallic carbon nanotubes can be easily separated without low cost and additional expensive equipment.
Figure 1 schematically shows a method for producing a magnetic nanoparticles surface-modified with an amine group according to the present invention.
FIG. 2 (a) is a photograph of a mixed solution (right test bottle) of single-walled carbon nanotubes and magnetic nanoparticles surface-modified with dispersed carbon nanotubes (left test bottle) and an amine group, and FIG. The magnetic field is applied to the mixed solution of magnetic nanoparticles and single-walled carbon nanotubes surface-modified by using permanent magnets. FIG. 2 (c) shows the supernatant separated from FIG. 2 (b), that is, metallic carbon nanotubes. This is a picture showing the remaining solution after separating the tube (left test bottle) and the supernatant, that is, a semiconductor single-walled carbon nanotube mixed solution (right test bottle).
Figure 3 (a) is a SEM picture of the solution (right test bottle) remaining in Figure 2 (c), 3 (b) is a SEM picture of the supernatant (left test bottle) in Figure 2 (c).
4 is a graph showing the 633 nm Raman spectrum of single-walled carbon nanotubes before and after the reaction with the surface-modified magnetic nanoparticles according to the present invention.
The present invention comprises the steps of mixing a carbon nanotube solution containing carbon nanotubes with a functional group formed on the surface and magnetic nanoparticles surface-modified with a functional group capable of covalently bonding the functional group; And
The present invention relates to a method for separating carbon nanotubes comprising the step of separating a semiconducting carbon nanotube and a metallic carbon nanotube by applying a magnetic field to the mixture prepared by the above step.
Hereinafter, the carbon nanotube separation method of the present invention will be described in more detail.
Carbon nanotube solution in the present invention is characterized in that it comprises a carbon nanotube having a functional group formed on the surface.
The type of the carbon nanotubes in the present invention is not particularly limited, and may be used alone or two or more, such as single-walled carbon nanotubes and double-walled carbon nanotubes. In the present invention, single-walled carbon nanotubes are preferred. The single-walled carbon nanotubes have high electronic properties, and thus have high industrial applicability.
In the present invention, the carbon nanotubes preferably include semiconducting carbon nanotubes and metallic carbon nanotubes.
In the present invention, the carbon nanotubes can be used commercially available products without limitation, and can also be synthesized in the laboratory and the like.
In the present invention, the method for synthesizing the carbon nanotubes is not particularly limited, and methods commonly used in the art may be used. In the present invention, the carbon nanotubes may be synthesized by an electric discharge method, laser ablation, chemical vapor deposition (CVD), or carbon monoxide (HiPco). have.
The carbon nanotubes synthesized by the above method include semiconducting carbon nanotubes and metallic carbon nanotubes.
In the carbon nanotube of the present invention, a functional group is formed on the surface thereof. The kind of the functional group is not particularly limited and may be, for example, a carboxyl group.
When the carboxyl group is formed on the surface of the carbon nanotubes in the present invention, the formation of the carboxyl group may be performed by acid treatment of the carbon nanotubes.
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In the present invention, the acid treatment may use an acid solvent. Here, the acid solvent to be used is not particularly limited, and a general acid solvent used in this field may be used without limitation. In particular, in the present invention, nitric acid, hydrochloric acid, sulfuric acid, hydrogen peroxide and mixtures thereof can be used as the acid solvent, and preferably a mixture of sulfuric acid and nitric acid can be used. At this time, the ratio of sulfuric acid and nitric acid is preferably 3: 1.
Acid treatment time in the present invention is not particularly limited and may be carried out for 15 to 35 hours.
In the present invention, the ultrasonic treatment may be performed together with the acid treatment of the carbon nanotubes. At this time, the ultrasonic treatment is preferably performed for about 10 hours during the performance of the acid treatment. At this time, the intensity of the ultrasonic wave is preferably 400 W to 500 W. By controlling the acid treatment time and the ultrasonic intensity, the size of the carbon nanotubes can be controlled.
The carbon nanotubes acid-treated by the present invention form carboxyl groups on the surfaces of carbon nanotubes, that is, semiconducting carbon nanotubes and metallic carbon nanotubes.
In addition, the acid treatment in the present invention has the effect of removing impurities in addition to the formation of a carboxyl group. When synthesizing carbon nanotubes in the present invention, the carbon nanotubes may include other impurities such as transition metals and / or amorphous carbon. Other impurities included in the carbon nanotubes can be removed through acid treatment.
In the present invention, the carbon nanotube solution may include a dispersant in addition to the carbon nanotube having a functional group formed on the surface thereof.
The dispersant inhibits the formation of a bundle consisting of semiconducting carbon nanotubes and metallic carbon nanotubes to the maximum, and increases dispersibility of the semiconducting carbon nanotubes or metallic carbon nanotubes, thereby increasing separation efficiency.
In this case, a surfactant may be used as the dispersant, and specifically, a cationic surfactant, an anionic surfactant, or a nonionic surfactant may be used. Examples of the cationic surfactant include DTAB (Dodecyltrimethylammonium bromide) and CTAB (Cetyltrimethylammonium bromide), and examples of anionic surfactants include sodium dodecyl sulfate (SDS), lithium dodecyl sulfate (LDS), and sodium dodecylbenzene sulfonate (SDBS). And SDSA (sodium dodecylsulfonate), and the like, and examples of nonionic surfactants include Triton X-100, polyethylene oxide-polybutylene oxide-polyethylene oxide 3-block copolymer (Poly (ethylene oxide) -Poly (butylene oxide) ) -Poly (ethylene oxide) triblock copolymer) and polyethylene oxide-polyphenylene oxide-polyethylene oxide 3-block copolymer (Poly (ethylene oxide) -Poly (phenylene oxide) -Poly (ethylene oxide) triblock copolymer) In the present invention, preferably selected from the group consisting of sodium dodecyl sulfate (SDS), sodium cholate hydrate (SC), sodium dodecylbenzene sulfonate (SDBS), Triton X-100, and the like. You can use more than one.
In the present invention, the acid-treated carbon nanotubes may be added to the dispersant, followed by high-speed centrifugation to remove the carbon nanotube bundles. As a result, the carbon nanotubes, that is, the semiconducting carbon nanotubes and the metallic carbon nanotubes are well dispersed in the dispersant.
In the present invention, in the magnetic nanoparticles surface-modified with a functional group covalently bonded to the functional group of carbon nanotubes, the type of the magnetic nanoparticles is not particularly limited as long as they are paramagnetic nanoparticles. For example, Co, Mn, Fe, It may comprise one or more selected from the group consisting of Ni, Gd, Mo, MM ' 2 O 4 and MpOq. Herein, M and M ′ represent Co, Fe, Ni, Mn, Zn, Gd, or Cr, respectively, and 0 <p ≦ 3 and 0 <q ≦ 5. In the present invention, Fe 2 O 3 and MnFe 2 O 4 may be preferably used.
In addition, the particle diameter of the magnetic nanoparticles of the present invention may be 10 nm to 20 nm.
In the present invention, the type of the functional group capable of covalently bonding with the functional group of the carbon nanotube is not particularly limited, and an amine group may be used.
Surface modification of the magnetic nanoparticles in the present invention may be made by mixing the magnetic nanoparticles and the amine compound, followed by sonication. The amine compound used in the present invention is TP80, aniline (aniline), methylamine (methylamine), propylamine (propylamine), butylamine (butylamine), isopropylamine (isopropylamine) and octylamine (octylamine) group One or more selected from may be used, preferably
The sonication may be performed for about 10 minutes.
By the above method, the magnetic nanoparticles form functional groups covalently bonded to the functional groups formed on the surface of the carbon nanotubes on their surfaces. Preferably, the amine groups formed on the magnetic nanoparticles may react with the carboxyl groups formed on the surface of the carbon nanotubes. Can be.
The mixing step of the present invention takes advantage of the property that the functional groups of the surface-modified magnetic nanoparticles selectively bind to the functional groups of the semiconducting carbon nanotubes rather than the functional groups of the metallic carbon nanotubes.
When the carbon nanotube solution and the surface-modified magnetic nanoparticles are mixed in the present invention, the magnetic nanoparticles selectively bind to the functional groups of the semiconducting carbon nanotubes rather than the metallic carbon nanotubes in the carbon nanotubes.
In the step of separating the semiconducting carbon nanotubes or the metallic carbon nanotubes of the present invention, the semiconducting carbon nanotubes may be separated by application of a magnetic field. In the mixing step, the semiconducting carbon nanotubes form covalent bonds through selective bonding with functional groups of the magnetic nanoparticles. When the magnetic field is applied thereto, since the magnetic nanoparticles are paramagnetic, the semiconducting carbon nanotubes combined with the surface-modified magnetic nanoparticles move in the direction in which the magnetic field is applied. Since the magnetic nanoparticles are brown, the semiconducting carbon nanotubes moved in the magnetic field direction form a brown layer and can be easily separated.
In the present invention, the method of applying the magnetic field is not particularly limited and can be performed using a magnet.
By performing the separation step one or more times, it is possible to increase the separation efficiency of the semiconducting carbon nanotubes.
The present invention also relates to a composition comprising a carbon nanotube having a functional group formed on its surface and magnetic nanoparticles surface-modified with a functional group covalently bonded to the functional group.
In the present invention, the type of carbon nanotubes is not particularly limited, and the above-described types of carbon nanotubes may be used, and preferably single-wall carbon nanotubes may be used.
In addition, the carbon nanotubes in the present invention may include semiconducting carbon nanotubes and metallic carbon nanotubes.
In the present invention, the kind of the functional group formed on the surface of the carbon nanotubes is not particularly limited, and the above-described kind may be used, and carboxyl groups may be preferably used.
In addition, the kind of functional group which can be covalently bonded to a functional group in this invention is not restrict | limited, The above-mentioned kind can be used, Preferably an amine group can be used.
The composition of the present invention may further include a dispersant in addition to the carbon nanotubes formed with functional groups on the surface and the magnetic nanoparticles surface-modified with the functional groups covalently bonded to the functional groups.
The type of the dispersant is not particularly limited, and the above-described type may be used.
Hereinafter, the present invention will be described in more detail with reference to the following examples. However, the scope of the present invention is not limited by the following examples.
Example 1 Preparation of Single Wall Carbon Nanotubes
After manufacturing single-walled carbon nanotubes using an electric discharge method, acid treatment was carried out in an acid solution containing sulfuric acid and nitric acid 3: 1 for 24 hours, and 10 hours of the 24 hours was subjected to sonication for single wall carbon nanotubes. Nanotubes were purified.
Thereafter, the purified carbon nanotubes were added to a sodium dodecyl sulfate (SDS) solution, followed by high-speed centrifugation to remove bundles of single-walled carbon nanotubes.
Example 2 Preparation of Magnetic Nanoparticles Surface-Modified with Amine Group
(1) Preparation of Magnetic Nanoparticles
2 mmol of iron (III) acetylacetonate, 1 mmol of manganese (II) acetylacetonate, 10 mmol of 1,2-hexadecanediol (1,2) -hexadecanediol), 6 mmol of dodecanoic acid and 6 mmol of dodecylamine were dissolved in 20 mL of benzyl ether in a nitrogen atmosphere to prepare a mixture. Thereafter, the mixture was heat-treated at 200 ° C. for 2 hours, refluxed at 300 ° C. for 30 minutes, cooled at room temperature, and purified using excess ethanol to prepare manganese ferrite (MnFe 2 O 4 ). .
(2) Synthesis of tri-aminated polysorbate 80 (TP80)
5 mmol of polysorbate (P80) and 15 mmol of 1,1'-carbonyldiimidazole (CDI) in 100 mL of 1,4-dioxane (1 , 4-dioxane) and 15 mmol of ethylenediamine (EDA) were added with stirring for 1 hour. After the reaction for 24 hours, the solvent was blown using a rotary evaporator to obtain a transparent gel.
The gel was dissolved in 10 mL of distilled water and dialyzed for 7 days to obtain TP80. Thereafter, the TP80 was lyophilized and stored under vacuum.
(3) Surface modification of magnetic nanoparticles
50 mg of magnetic nanoparticles (MnFe 2 O 4 ) prepared by (1) was dissolved in 4 mL of hexane, and then mixed with 20 mL of PBS (phosphate buffer saline) containing 100 mg of TP80 to prepare an emulsion. Prepared. Thereafter, the emulsion was sonicated for 10 minutes, the organic solvent was evaporated at room temperature, purified by centrifugal filters to prepare magnetic nanoparticles surface-modified with an amine group.
1 shows a method of preparing the magnetic nanoparticles surface-modified with the amine group. As shown in FIG. 1, when the magnetic nanoparticles (MnFe 2 O 4 ) and TP80 react, MnFe 2 O 4 TP80 is bonded to the phase, and the magnetic nanoparticles (MnFe 2 O 4 ) have an amine group.
Example 3 Separation of Semiconducting Carbon Nanotubes and Metallic Carbon Nanotubes
After mixing the carbon nanotubes prepared in Example 1 and the magnetic nanoparticles surface-modified with the amine group prepared in Example 2, a magnetic field was applied to the mixed solution using a permanent magnet. When the magnetic field is applied, the semiconducting carbon nanotubes combined with the magnetic nanoparticles move toward the permanent magnet, thereby forming a brown layer. The formed layer was separated to separate semiconducting carbon nanotubes and metallic carbon nanotubes.
FIG. 2 (a) is a photograph of a mixed solution (right test bottle) of single-walled carbon nanotubes and magnetic nanoparticles surface-modified with dispersed carbon nanotubes (left test bottle) and an amine group, and (b) is an amine group The magnetic field is applied to the mixed solution of surface-modified magnetic nanoparticles and single-walled carbon nanotubes using permanent magnets, and (c) shows the supernatant separated from (b), that is, metallic carbon nanotubes (left test bottle). ) And the supernatant and the remaining solution, that is, a semiconducting single-walled carbon nanotube mixed solution (right test bottle).
In addition, the SEM image of Figure 3 (a) is a photograph of the solution (right test bottle) remaining in Figure 2 (c), the SEM image on the right is a photograph of the supernatant (left test bottle) in Figure 2 (c). Indicates.
As shown in FIG. 2 (b), when a magnetic field is applied to a mixed solution of magnetic nanoparticles surface-modified with an amine group and a single-wall carbon nanotube using permanent magnets, the magnetic nanoparticles are paramagnetic, Very sensitive. Accordingly, the semiconducting single-walled carbon nanotubes combined with the surface-modified magnetic nanoparticles move in the direction in which the magnetic field is applied, that is, toward the permanent magnet, and the metallic carbon nanotubes are in a dispersed state. 2 (c), when the solution is moved toward the permanent magnet (right test tube), since the color of the magnetic nanoparticles is brown, the solution also becomes dark brown.
Separation of the semiconducting carbon nanotubes and the metallic carbon nanotubes may also be confirmed through the SEM photograph of FIG. 3. As shown in FIG. 3, the supernatant (FIG. 3B) hardly adheres the magnetic nanoparticles surface-modified with the amine group, but the remaining solution (SEM photograph of FIG. 3A) has a single wall of the magnetic nanoparticles surface-modified with the amine group. It can be seen that it is bonded to carbon nanotubes.
4 shows the 633 nm Raman spectrum of single-walled carbon nanotubes before and after the reaction with the magnetic nanoparticles surface-modified with an amine group. Figure (a) shows Raman spectra of single-walled carbon nanotubes before reaction with magnetic nanoparticles surface-modified with amine groups, and Figure (b) shows the semiconducting behavior toward magnets after reaction with magnetic nanoparticles surface-modified with amine groups. Raman spectra of single-walled carbon nanotubes. Figure (c) shows the Raman spectra of a portion of the metal single-walled carbon nanotubes, which are not collected toward the magnet. Raman spectra represent Radial Breathing Modes (RBMs). The spectrum before the reaction with the magnetic nanoparticles can be seen that the respective peaks in the S33, M11 region. This indicates that the carbon nanotubes before the reaction with the magnetic nanoparticles exist as semiconducting single-walled carbon nanotubes and metallic single-walled carbon nanotubes. The semiconducting single-walled carbon nanotubes reacted with the magnets were markedly reduced in the M11 region, and the metallic single-walled carbon nanotubes not reacted with the magnets had a strong peak in the M11 region. The single-walled carbon nanotubes attracted to the magnet after reaction with magnetic nanoparticles surface-modified with an amine group consist of semiconducting carbon nanotubes, and the single-walled carbon nanotubes not attracted to the magnet consist of metallic carbon nanotubes. Prove that.
Claims (14)
Separation method of the single-walled carbon nanotubes comprising the step of separating the semiconducting carbon nanotubes and metallic carbon nanotubes by applying a magnetic field to the mixture prepared by the step.
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| KR20140033555A (en) | 2012-08-29 | 2014-03-19 | 삼성전자주식회사 | Method for separating carbon nanotubes |
| CN104931628B (en) * | 2015-06-02 | 2017-03-22 | 华南师范大学 | Fe3O4-COOH magnetic nano-material modified open tubular column as well as preparation method and application thereof |
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| US20050022726A1 (en) * | 2003-01-13 | 2005-02-03 | Stanislaus Wong | Carbon nanotube-nanocrystal heterostructures and methods of making the same |
| JP2007031238A (en) | 2005-07-29 | 2007-02-08 | Sony Corp | Method for separation of metallic carbon nanotube, method for producing thin film of semiconducting carbon nanotube, thin-film transistor and its production method, electronic element, and method of producing the element |
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| WO2005069789A2 (en) * | 2003-12-18 | 2005-08-04 | Clemson University | Process for separating metallic from semiconducting single-walled carbon nanotubes |
| KR20100025113A (en) * | 2008-08-27 | 2010-03-09 | 재단법인서울대학교산학협력재단 | Separation method of carbon nanotubes |
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| US20050022726A1 (en) * | 2003-01-13 | 2005-02-03 | Stanislaus Wong | Carbon nanotube-nanocrystal heterostructures and methods of making the same |
| JP2007031238A (en) | 2005-07-29 | 2007-02-08 | Sony Corp | Method for separation of metallic carbon nanotube, method for producing thin film of semiconducting carbon nanotube, thin-film transistor and its production method, electronic element, and method of producing the element |
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| Yonghui Deng et al. Chem. Commun. 2005, pp. 5548-5550* |
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