JP2005200272A - Carbon nanotube and method of manufacturing the same - Google Patents
Carbon nanotube and method of manufacturing the same Download PDFInfo
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- JP2005200272A JP2005200272A JP2004008597A JP2004008597A JP2005200272A JP 2005200272 A JP2005200272 A JP 2005200272A JP 2004008597 A JP2004008597 A JP 2004008597A JP 2004008597 A JP2004008597 A JP 2004008597A JP 2005200272 A JP2005200272 A JP 2005200272A
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- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 title claims abstract description 56
- 239000002041 carbon nanotube Substances 0.000 title claims abstract description 55
- 229910021393 carbon nanotube Inorganic materials 0.000 title claims abstract description 55
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 17
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims abstract description 28
- 125000004432 carbon atom Chemical group C* 0.000 claims description 15
- 239000002904 solvent Substances 0.000 claims description 15
- 239000000463 material Substances 0.000 abstract description 10
- 125000001153 fluoro group Chemical group F* 0.000 abstract description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 6
- 239000003814 drug Substances 0.000 abstract description 3
- -1 perfluoro Chemical group 0.000 abstract description 2
- 230000004071 biological effect Effects 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 16
- 238000000034 method Methods 0.000 description 10
- 229960004624 perflexane Drugs 0.000 description 7
- ZJIJAJXFLBMLCK-UHFFFAOYSA-N perfluorohexane Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F ZJIJAJXFLBMLCK-UHFFFAOYSA-N 0.000 description 7
- 229910052731 fluorine Inorganic materials 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 230000001766 physiological effect Effects 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
- HZBIPQWVEKXYMJ-UHFFFAOYSA-N bis(1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluorooctyl)diazene Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)N=NC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F HZBIPQWVEKXYMJ-UHFFFAOYSA-N 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 3
- 229910052753 mercury Inorganic materials 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000002341 toxic gas Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 238000004833 X-ray photoelectron spectroscopy Methods 0.000 description 2
- 239000012300 argon atmosphere Substances 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 239000008204 material by function Substances 0.000 description 2
- LGUZHRODIJCVOC-UHFFFAOYSA-N perfluoroheptane Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F LGUZHRODIJCVOC-UHFFFAOYSA-N 0.000 description 2
- YVBBRRALBYAZBM-UHFFFAOYSA-N perfluorooctane Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F YVBBRRALBYAZBM-UHFFFAOYSA-N 0.000 description 2
- 125000005007 perfluorooctyl group Chemical group FC(C(C(C(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)* 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- YTQXZZNYAQZJOU-FOCLMDBBSA-N (e)-bis(1,1,2,2,2-pentafluoroethyl)diazene Chemical compound FC(F)(F)C(F)(F)\N=N\C(F)(F)C(F)(F)F YTQXZZNYAQZJOU-FOCLMDBBSA-N 0.000 description 1
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 1
- 238000000026 X-ray photoelectron spectrum Methods 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- QVXSVCGEIWPBMH-UHFFFAOYSA-N bis(1,1,2,2,3,3,3-heptafluoropropyl)diazene Chemical compound FC(F)(F)C(F)(F)C(F)(F)N=NC(F)(F)C(F)(F)C(F)(F)F QVXSVCGEIWPBMH-UHFFFAOYSA-N 0.000 description 1
- SFKQEHRVVHZQRE-UHFFFAOYSA-N bis(1,1,2,2,3,3,4,4,5,5,6,6,6-tridecafluorohexyl)diazene Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)N=NC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F SFKQEHRVVHZQRE-UHFFFAOYSA-N 0.000 description 1
- DAFMJBZCDIPWQR-UHFFFAOYSA-N bis(1,1,2,2,3,3,4,4,5,5,6,6,7,7,7-pentadecafluoroheptyl)diazene Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)N=NC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F DAFMJBZCDIPWQR-UHFFFAOYSA-N 0.000 description 1
- YDBRUXDOAMOVPN-UHFFFAOYSA-N bis(trifluoromethyl)diazene Chemical compound FC(F)(F)N=NC(F)(F)F YDBRUXDOAMOVPN-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000007385 chemical modification Methods 0.000 description 1
- 238000012377 drug delivery Methods 0.000 description 1
- 239000012776 electronic material Substances 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 239000002048 multi walled nanotube Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 230000002940 repellent Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000002109 single walled nanotube Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Abstract
Description
本発明は、フッ素官能基がその表面に結合しているカーボンナノチューブ及びその製造方法に関する。 The present invention relates to a carbon nanotube having a fluorine functional group bonded to its surface and a method for producing the carbon nanotube.
カーボンナノチューブは、燃料電池および電子部品分野をはじめとし、種々な分野で用いられている。このカーボンナノチューブの表面に各種の処理を施すことにより、電気的、物理的、化学的に優れた高機能特性を付加することができることが期待されている。このようなことから、より広範囲の分野での利用が期待されている材料である。
その一例として表面に化学修飾を施すことにより、より高付加価値を有する材料となることが期待される。化学修飾を施す場合に、従来から特異な特性を有する官能基を導入することにより付加価値を高めることができる。
Carbon nanotubes are used in various fields including fuel cells and electronic parts. It is expected that highly functional characteristics excellent in electrical, physical, and chemical properties can be added by performing various treatments on the surface of the carbon nanotube. For these reasons, the material is expected to be used in a wider range of fields.
As an example, it is expected that a material having higher added value can be obtained by chemically modifying the surface. When chemical modification is performed, the added value can be increased by introducing a functional group having unique characteristics.
一般に、フッ素官能基を有する材料は、フッ素原子やフッ素原子含有官能基特有の特異な性質を有し、生理活性、電導性、撥水性、撥油性、潤滑性等の機能を発現することができることから、医薬、電子デバイス、機能性材料として有用であるとして注目を浴びてきた材料である。
カーボンナノチューブ表面上へフッ素基を導入することによって化学的に安定となり、極限環境に耐えうる材料としての利用が期待されている。
In general, a material having a fluorine functional group has unique properties peculiar to a fluorine atom or a fluorine atom-containing functional group, and can exhibit functions such as physiological activity, electrical conductivity, water repellency, oil repellency, and lubricity. Therefore, it is a material that has attracted attention as being useful as a medicine, an electronic device, and a functional material.
The introduction of fluorine groups onto the surface of carbon nanotubes is expected to be used as a material that is chemically stable and can withstand extreme environments.
従来、カーボンナノチューブ表面上にフッ素を導入する方法としては、（イ）ＣＦ４プラズマを作用させる方法、（ロ）フッ素を作用させる方法、及び（ハ）ヨウ化ペルフルオロアルキルを作用させる方法（非特許文献１、２、３参照）が、知られている。
しかしながら、（イ）、（ロ）の方法においては使用するガスは、取り扱いが困難である有毒ガスを使用する必要がある。このような特殊材料ガスを使用する場合、特別な反応容器が必要となり操作も煩雑となる。また、（ハ）の方法としては反応に伴う副生成物であるヨウ素ラジカルがカーボンナノチューブと反応し、所望の生成物が得られないといった欠点があった。
Conventionally, as a method of introducing fluorine onto the surface of a carbon nanotube, (a) a method of applying CF 4 plasma, (b) a method of operating fluorine, and (c) a method of operating perfluoroalkyl iodide (non-patented) Documents 1, 2, and 3) are known.
However, in the methods (a) and (b), it is necessary to use a toxic gas that is difficult to handle. When such a special material gas is used, a special reaction vessel is required and the operation becomes complicated. Further, the method (c) has a drawback that iodine radicals, which are by-products accompanying the reaction, react with the carbon nanotubes and a desired product cannot be obtained.
本発明は、生理活性、電導性、撥水性、撥油性、潤滑性等の機能を有し、医薬、電子デバイス、機能性材料として極めて有用なカーボンナノチューブ表面上にフッ素官能基を導入した（結合した）、新規なカーボンナノチューブおよびこのものを有毒ガスを使用することなく安全、かつ高純度で、工業的に有利に製造し得る方法を提供することを目的とする。 The present invention has functions such as physiological activity, electrical conductivity, water repellency, oil repellency, lubricity, etc., and has introduced a fluorine functional group on the surface of a carbon nanotube that is extremely useful as a pharmaceutical, electronic device, or functional material (bonding). It is an object of the present invention to provide a novel carbon nanotube and a method for producing the carbon nanotube safely and with high purity without using a toxic gas and industrially advantageously.
本発明者らは、紫外線照射下、カーボンナノチューブとペルフルオロアゾアルカンを反応させると、意外にも、カーボンナノチューブ表面上にペルフルオロアルキル基が化学的に結合することを見いだし、本発明を完成するに至った。
すなわち、本発明によれば、以下の発明が提供される。
（１）ペルフルオロアルキル基がその表面に結合していることを特徴とするカーボンナノチューブ。
（２） ペルフルオロアルキル基の炭素数が１〜１２であることを特徴とする上記（１）に記載のカーボンナノチューブ。
（３） ペルフルオロアルキル基の炭素数が６〜１０であることを特徴とする上記（１）記載のカーボンナノチューブ。
（４） ペルフルオロアルキル基の炭素数が７〜９であることを特徴とする上記（１）に記載のカーボンナノチューブ。
（５） 紫外線照射下、カーボンナノチューブと下記一般式（１）で表されるペルフルオロアゾアルカンを反応させることを特徴とするペルフルオロアルキル基がその表面に結合したカーボンナノチューブの製造方法。
ＲＦＮ＝ＮＲＦ （１）
（式中、ＲＦはペルフルオロアルキル基を示す。）
（６） ペルフルオロアルキル基の炭素数が１〜１２であることを特徴とする上記（５）に記載のカーボンナノチューブの製造方法。
（７） ペルフルオロアルキル基の炭素数が６〜１０であることを特徴とする上記（５）に記載のカーボンナノチューブの製造方法。
（８） ペルフルオロアルキル基の炭素数が７〜９であることを特徴とする上記（５）に記載のカーボンナノチューブの製造方法。
（９） ペルフルオロアルカン溶媒中にペルフルオロアゾアルカンを添加することを特徴とする上記（５）乃至（８）のいずれかに記載のカーボンナノチューブの製造方法。
（１０） ペルフルオロアゾアルカン１ｍｇに対してペルフルオロアルカン溶媒を０．５ｍｌ〜３ｍｌ使用することを特徴とする上記（９）に記載のカーボンナノチューブの製造方法。
The present inventors have unexpectedly found that when a carbon nanotube and a perfluoroazoalkane are reacted under ultraviolet irradiation, a perfluoroalkyl group is chemically bonded to the surface of the carbon nanotube, and the present invention has been completed. It was.
That is, according to the present invention, the following inventions are provided.
(1) A carbon nanotube characterized in that a perfluoroalkyl group is bonded to the surface thereof.
(2) The carbon nanotube as described in (1) above, wherein the perfluoroalkyl group has 1 to 12 carbon atoms.
(3) The carbon nanotube according to (1), wherein the perfluoroalkyl group has 6 to 10 carbon atoms.
(4) The carbon nanotube as described in (1) above, wherein the perfluoroalkyl group has 7 to 9 carbon atoms.
(5) A method for producing a carbon nanotube in which a perfluoroalkyl group is bonded to the surface of the carbon nanotube and a perfluoroazoalkane represented by the following general formula (1) under ultraviolet irradiation.
R F N = NR F (1)
(In the formula, R F represents a perfluoroalkyl group.)
(6) The method for producing carbon nanotubes as described in (5) above, wherein the perfluoroalkyl group has 1 to 12 carbon atoms.
(7) The carbon nanotube production method as described in (5) above, wherein the perfluoroalkyl group has 6 to 10 carbon atoms.
(8) The method for producing carbon nanotubes as described in (5) above, wherein the perfluoroalkyl group has 7 to 9 carbon atoms.
(9) The method for producing carbon nanotubes according to any one of (5) to (8) above, wherein perfluoroazoalkane is added to a perfluoroalkane solvent.
(10) The method for producing carbon nanotubes as described in (9) above, wherein 0.5 ml to 3 ml of a perfluoroalkane solvent is used per 1 mg of perfluoroazoalkane.
本発明に係る、カーボンナノチューブの表面上にペルフルオロアルキル基が導入された（結合した）、カーボンナノチューブは新規物質であり、生理活性、撥水性、撥油性、潤滑性等の機能を有し、医薬、電子デバイス、機能性材料として極めて有用なものである。また、本発明の製造方法によれば、有毒ガスを使用することなく、常温の溶液中で紫外光照射をするだけの簡便な反応操作により、カーボンナノチューブ表面上にフッ素官能基を導入した（結合した）、新規なカーボンナノチューブを得ることができる。また本方法においては、反応に伴って生成する窒素は化学的に不活性なため、副反応が抑制されるので、高純度で上記カーボンナノチューブを得ることができる。 According to the present invention, a perfluoroalkyl group is introduced (bonded) onto the surface of the carbon nanotube, and the carbon nanotube is a novel substance and has functions such as physiological activity, water repellency, oil repellency, lubricity, and the like. They are extremely useful as electronic devices and functional materials. In addition, according to the production method of the present invention, a fluorine functional group was introduced onto the surface of carbon nanotubes (bonding) by a simple reaction operation by simply irradiating ultraviolet light in a solution at room temperature without using a toxic gas. New carbon nanotubes can be obtained. Moreover, in this method, since the nitrogen produced | generated with reaction is chemically inactive, a side reaction is suppressed, Therefore The said carbon nanotube can be obtained with high purity.
本発明に係るカーボンナノチューブは、その表面にペルフルオロアルキル基が結合していることを特徴としている。
ペルフルオロアルキル基としては、炭素数が１〜１２、好ましくは、６〜１０、更に好ましくは炭素数が７〜９のものである。
原材料であるカーボンナノチューブとしては、単層あるいは多層の何れのものも使用することができる。
本発明で得られる、カーボンナノチューブはその表面にペルフルオロアルキル基が結合していることから、生理活性、電導性、撥水性、撥油性、潤滑性等の機能を有し、医薬（ドラッグデリバリーシステム）、電子材料（電子デバイス）、機能性材料（撥水剤、廃油剤、潤滑剤）等として極めて有用なものである。
The carbon nanotube according to the present invention is characterized in that a perfluoroalkyl group is bonded to the surface thereof.
The perfluoroalkyl group has 1 to 12 carbon atoms, preferably 6 to 10 carbon atoms, and more preferably 7 to 9 carbon atoms.
As the carbon nanotube as a raw material, either single-walled or multi-walled carbon nanotubes can be used.
The carbon nanotubes obtained by the present invention have functions such as physiological activity, electrical conductivity, water repellency, oil repellency, lubricity, etc., because a perfluoroalkyl group is bonded to the surface thereof, and pharmaceuticals (drug delivery systems) They are extremely useful as electronic materials (electronic devices), functional materials (water repellents, waste oils, lubricants).
本発明に係るカーボンナノチューブは、紫外線照射下、カーボンナノチューブと下記一般式（１）で示されるペルフルオロアゾアルカンと反応させることによって製造することができる。
ＲＦＮ＝ＮＲＦ （１）
（式中、ＲＦは、ペルフルオロアルキル基を示す）。
The carbon nanotube according to the present invention can be produced by reacting a carbon nanotube with a perfluoroazoalkane represented by the following general formula (1) under ultraviolet irradiation.
R F N = NR F (1)
(Wherein R F represents a perfluoroalkyl group).
前記ペルフルオロアゾアルカンのペルフルオロアルキル基の炭素数は、反応の簡便さ及び高機能性の発現という理由から１〜１２とする。好ましくは６〜１０、より好ましくは７〜９である。
具体的にはペルフルオロアゾオクタン、ペルフルオロアゾヘプタン、ペルフルオロアゾヘキサン、ペルフルオロアゾプロパン、ペルフルオロアゾエタン、ペルフルオロアゾメタン等が用いられる。本発明方法の反応においては、これらのペルフルオロアルカンの鎖長による反応性の差はない。
The carbon number of the perfluoroalkyl group of the perfluoroazoalkane is set to 1 to 12 because of the simplicity of the reaction and the expression of high functionality. Preferably it is 6-10, More preferably, it is 7-9.
Specifically, perfluoroazooctane, perfluoroazoheptane, perfluoroazohexane, perfluoroazopropane, perfluoroazoethane, perfluoroazomethane and the like are used. In the reaction of the method of the present invention, there is no difference in reactivity due to the chain length of these perfluoroalkanes.
本発明の方法では、前記一般式（１）で表されるペルフルオロアゾアルカンの脱窒素反応によるペルフルオロアルキルラジカルの発生が必要であることから、このために紫外光照射下に行う。波長は１８０ｎｍから３００ｎｍのものを使用することが望ましい。 In the method of the present invention, it is necessary to generate a perfluoroalkyl radical by denitrogenation of the perfluoroazoalkane represented by the general formula (1). It is desirable to use a wavelength of 180 nm to 300 nm.
光源としては公知のものが用いられ、低圧水銀灯、高圧水銀灯、ＡｒＦまたはＸｅＣｌエキシマレーザー、エキシマランプ等が適用でき、広範囲の波長の光を利用できる。
反応の高効率化のためには、２００ｎｍ以下の波長を有する紫外光照射下に反応を行うことが好ましい。光量は、０．１〜１００ｍＷ／ｃｍ２の範囲で照射される。
照射時間は１から８時間程度が必要である。
A known light source is used, and a low-pressure mercury lamp, a high-pressure mercury lamp, an ArF or XeCl excimer laser, an excimer lamp, or the like can be applied, and light having a wide range of wavelengths can be used.
In order to increase the efficiency of the reaction, the reaction is preferably performed under irradiation with ultraviolet light having a wavelength of 200 nm or less. The amount of light is irradiated in the range of 0.1 to 100 mW / cm 2 .
The irradiation time needs about 1 to 8 hours.
本発明の方法に際しては、原料物質である前記ペルフルオロアゾアルカンを、溶媒中に添加するのが望ましい。推奨される溶媒は、ペルフルオロアルカンである。このペルフオロアルカンの具体例としては、ペルフルオロヘキサン、ペルフルオロヘプタン、ペルフルオロオクタンなどをあげることができる。原料物質であるペルフルオロアゾアルカンは通常の有機溶媒に溶けにくいので、これらの溶媒を使用するのが望ましい。
溶媒量は、ペルフルオロアゾアルカンの使用量に応じて決定する。この反応原料を溶媒中に保存することができる量であれば差し支えないが、十分に溶媒中に混和することができ、かつ反応に際して光照射を十分に行うことができる量を必要とする。
このようなことを考慮して、ペルフルオロアゾアルカン１ｍｇに対して、０．５ｍｌ以上、３ｍｌ以下のペルフルオロアルカンが使用することが望ましい。
In the method of the present invention, it is desirable to add the perfluoroazoalkane which is a raw material to a solvent. The recommended solvent is perfluoroalkane. Specific examples of the perfluoroalkane include perfluorohexane, perfluoroheptane, perfluorooctane, and the like. Since perfluoroazoalkane as a raw material is hardly soluble in ordinary organic solvents, it is desirable to use these solvents.
The amount of solvent is determined according to the amount of perfluoroazoalkane used. Any amount can be used as long as the reaction raw material can be stored in the solvent, but an amount that can be sufficiently mixed in the solvent and sufficiently irradiated with light during the reaction is required.
Considering this, it is desirable to use 0.5 to 3 ml of perfluoroalkane per 1 mg of perfluoroazoalkane.
本発明の反応は、加熱する必要がなく、室温下で容易に進行させることができる。本発明の反応を行うにあたっては、アルゴンまたは窒素雰囲気を介して懸濁液に光照射を行うのが望ましい。 The reaction of the present invention does not need to be heated and can easily proceed at room temperature. In carrying out the reaction of the present invention, it is desirable to irradiate the suspension with light through an argon or nitrogen atmosphere.
また、本発明においては、反応終了後、溶媒を除去する。カーボンナノチューブを溶剤により洗浄し、不必要な付着物を除去する。溶剤には前記ペルフルオロアルカン及びアルカンを用いることができる。
このようにして得られるフッ素化カーボンナノチューブの同定は、表面に前記ペルフルオロアルキル基が化学結合しているかどうかを各種の分析機器たとえばＸＰＳなどを利用することにより行われる。
In the present invention, the solvent is removed after completion of the reaction. The carbon nanotubes are washed with a solvent to remove unnecessary deposits. The perfluoroalkane and alkane can be used as the solvent.
Identification of the fluorinated carbon nanotubes thus obtained is performed by using various analytical instruments such as XPS to determine whether or not the perfluoroalkyl group is chemically bonded to the surface.
以下、本発明を実施例により詳細に説明する。 Hereinafter, the present invention will be described in detail with reference to examples.
実施例１
合成石英製の反応容器に、ペルフルオロアゾオクタン（４ｍｇ）をペルフルオロヘキサン（４ｍｌ）に溶解させ、カーボンナノチューブを入れた。
アルゴン雰囲気下で攪拌しつつ低圧水銀灯を室温で８時間照射した。その後、ペルフルオロヘキサン溶液を除去し、カーボンナノチューブをペルフルオロヘキサンおよびヘキサンで洗浄し、減圧下で乾燥を行った。
反応後のカーボンナノチューブのＸＰＳ測定を行った。その結果を図１に示す。図１に示されるように、フッ素に由来するピークが観測され、表面上にペルフルオロオクチル基が導入されたことが判る。
Example 1
In a reaction vessel made of synthetic quartz, perfluoroazooctane (4 mg) was dissolved in perfluorohexane (4 ml), and carbon nanotubes were placed therein.
While stirring in an argon atmosphere, a low-pressure mercury lamp was irradiated at room temperature for 8 hours. Thereafter, the perfluorohexane solution was removed, the carbon nanotubes were washed with perfluorohexane and hexane, and dried under reduced pressure.
The XPS measurement of the carbon nanotube after reaction was performed. The result is shown in FIG. As shown in FIG. 1, a peak derived from fluorine was observed, and it was found that a perfluorooctyl group was introduced on the surface.
なお、上記実施例１においては、反応材料としてペルフルオロアゾオクタン及び溶媒としてペルフルオロヘキサンを使用したが、ペルフルオロアゾアルカンであるペルフルオロアゾヘプタン、ペルフルオロアゾヘキサン、ペルフルオロアゾプロパン、ペルフルオロアゾエタン、ペルフルオロアゾメタン等を使用した場合、また溶媒としてペルフルオロアルカンであるペルフルオロヘキサン、ペルフルオロヘプタン、ペルフルオロオクタンなどを使用した場合でも、上記実施例と同様の結果を得ることができた。 In Example 1, perfluoroazooctane was used as a reaction material and perfluorohexane was used as a solvent. Even when perfluorohexane, perfluorohexane, perfluoroheptane, perfluorooctane or the like was used as a solvent, the same results as in the above examples could be obtained.
Claims (10)
ＲＦＮ＝ＮＲＦ （１）
（式中、ＲＦはペルフルオロアルキル基を示す。） A method for producing a carbon nanotube having a perfluoroalkyl group bonded to its surface, which comprises reacting a carbon nanotube with a perfluoroazoalkane represented by the following general formula (1) under ultraviolet irradiation.
R F N = NR F (1)
(In the formula, R F represents a perfluoroalkyl group.)
The method for producing carbon nanotubes according to claim 9, wherein 0.5 ml to 3 ml of a perfluoroalkane solvent is used per 1 mg of perfluoroazoalkane.
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| WO2010074000A1 (en) * | 2008-12-24 | 2010-07-01 | 国立大学法人東北大学 | Dispersion of carbon material and process for producing same |
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