CN110418766B - Multilayered carbon nanotube, method for producing multilayered carbon nanotube, dispersion liquid, resin composition, and coating film - Google Patents
Multilayered carbon nanotube, method for producing multilayered carbon nanotube, dispersion liquid, resin composition, and coating film Download PDFInfo
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- CN110418766B CN110418766B CN201880017332.7A CN201880017332A CN110418766B CN 110418766 B CN110418766 B CN 110418766B CN 201880017332 A CN201880017332 A CN 201880017332A CN 110418766 B CN110418766 B CN 110418766B
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- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
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Abstract
The invention provides a multilayered carbon nanotube capable of obtaining a resin composition with high jet-blackness, a method for producing the multilayered carbon nanotube, a dispersion liquid, a resin composition and a coating film. A multilayered carbon nanotube satisfying the following conditions (1) and (2). (1) The average outer diameter of the multilayered carbon nanotube is 10nm or less (2) the standard deviation of the outer diameter of the multilayered carbon nanotube is 4nm or less.
Description
The present application claims priority based on japanese patent application No. 2017-49759 filed on 3/15 of 2017 and japanese patent application No. 2017-243686 filed on 12/20 of 2017, the entire disclosures of which are incorporated herein by reference.
Technical Field
The present invention relates to a multilayered carbon nanotube and a method for producing a multilayered carbon nanotube. More specifically, the present invention relates to a multilayered carbon nanotube, a resin composition containing a multilayered carbon nanotube and a resin, a dispersion liquid thereof, and a coating film having excellent jet-black properties, which is coated with the dispersion liquid.
Background
The carbon nanotube is a cylindrical carbon material having an outer diameter of several nanometers to several tens of nanometers. Carbon nanotubes have high electrical conductivity and mechanical strength. Therefore, carbon nanotubes are expected to be used as functional materials in a wide range of fields including electronic engineering and energy engineering. Examples of the functional material include a fuel cell, an electrode, an electromagnetic wave shielding material, a conductive resin, a member for Field Emission Display (FED), and an absorbing material for various gases including hydrogen.
On the other hand, as a development example of the functional material, there are few examples of using carbon nanotubes as a color material. The color material uses carbon black instead of carbon nanotubes. For example, as shown in patent documents 1 and 2, carbon black is used for obtaining resin coatings, films, and molded articles having a jet-black property. Carbon black is uniformly dispersed in the resin solution or the solid resin.
However, color materials containing carbon black tend to have high brightness (L) (i.e., gray and white). Further, the chromaticity (a, b) is the positive direction (+ a: red, + b: yellow). Here, L, a, and b represent the values of L a b color system specified in Japanese Industrial Standards (JIS) Z8781-4. Therefore, it is difficult for carbon black to exhibit a blackness property such as so-called "piano black" or "wet feathering of crow.
Further, the color tone of a molded article using carbon black tends to vary depending on the primary particle diameter of carbon black. Specifically, when carbon black having a small primary particle diameter is used, blue color is developed, while the degree of blackness is reduced. As described above, in the conventional black color material, the blackness and the blue color are in a trade-off relationship. Therefore, it is difficult to reproduce a color tone having blue and high blackness, that is, a jet black color tone.
In addition, a method of adding an organic pigment such as phthalocyanine blue to carbon black is also known. With the method, the color material may appear blue in addition to black. However, the degree of blackness decreases with the addition of an organic pigment in the color material. Therefore, when the molded body including the color material is observed under direct sunlight, the molded body is observed to float red. The problem is recognized as the occurrence of the so-called bronze phenomenon.
In order to solve these problems, patent documents 6 and 7 have studied a laminate of carbon nanotubes. However, layer formation is required in these methods to obtain gloss of the resin composition containing carbon nanotubes. In addition, patent document 8 also studies carbon nanotubes as a jet-black pigment, but the outer diameter is large and jet-black property is insufficient when a coating film is formed. Further, although development of a single-walled carbon nanotube or a double-walled carbon nanotube having a small outer diameter has been advanced, dispersion is difficult, and it is difficult to produce a sufficient black-and-white feeling.
In addition, in patent document 9, the catalyst is made fine to suppress entanglement during the synthesis of the carbon nanotubes, thereby enlarging the voids in the carbon nanotube aggregate structure and producing the carbon nanotubes having excellent dispersibility in the resin. However, carbon nanotubes having a small outer diameter cannot be efficiently obtained.
Documents of the prior art
Patent literature
Patent document 1: japanese patent laid-open No. 2001-179176
Patent document 2: japanese patent laid-open No. 2004-098033
Patent document 3: japanese patent laid-open publication No. Hei 6-122834
Patent document 4: japanese patent laid-open publication No. 6-136287
Patent document 5: japanese patent laid-open No. 2008-285632
Patent document 6: japanese patent laid-open No. 2016-13680
Patent document 7: japanese patent laid-open No. 2016-22664
Patent document 8: japanese patent laid-open No. 2015-229706
Patent document 9: japanese patent laid-open No. 2008-173608
Disclosure of Invention
Problems to be solved by the invention
The present invention has been made to solve the above-mentioned conventional problems, and an object of the present invention is to provide a multilayered carbon nanotube capable of obtaining a resin composition having high jet-blackness, and a method for synthesizing the multilayered carbon nanotube.
Means for solving the problems
The present inventors have made extensive studies and found that the above problems can be solved by a specific multilayered carbon nanotube.
That is, the present invention relates to a multilayered carbon nanotube satisfying the following conditions (1) and (2):
(1) The average outer diameter of the multi-layer carbon nanotube is 10nm or less
(2) The standard deviation of the outer diameter of the multi-layer carbon nanotube is 4nm or less
In one embodiment of the multilayered carbon nanotube, a peak exists at a diffraction angle 2 θ =25 ° ± 2 ° in a powder X-ray diffraction analysis, and a half-value width of the peak is 3 ° or more and 5 ° or less.
In another embodiment of the multilayered carbon nanotube, in a powder X-ray diffraction analysis, a peak having a half-value width of more than 5 ° and 5.5 ° or less exists at a diffraction angle 2 θ =25 ° ± 2 °.
In one embodiment of the multilayered carbon nanotube, X + -2 sigma satisfies 2.5nm + -2 sigma-15.5 nm when X is an average outer diameter of the multilayered carbon nanotube and sigma is a standard deviation of the outer diameter of the multilayered carbon nanotube.
In one embodiment of the multilayered carbon nanotube, 1560cm is used in Raman spectroscopy -1 ~1600cm -1 G, 1310cm, or -1 ~1350cm -1 The G/D ratio is 2.0 or less, preferably 1.0 or less, where D is the maximum peak intensity in the range of (1).
The method for producing a multilayered carbon nanotube of the present invention includes the following steps.
(1) Mixing and/or pulverizing an active component containing one or more selected from cobalt, nickel and iron with a catalyst support containing one or more selected from magnesium, aluminum and silicon, and calcining the mixture to obtain a catalyst
(2) A step of contacting the catalyst with a carbon source containing at least one selected from the group consisting of hydrocarbons and alcohols under heating to obtain a multilayered carbon nanotube
In one embodiment of the method for producing a multilayered carbon nanotube, in the step (2), the carbon source contains a hydrocarbon, and the amount of the catalyst and/or the flow rate of the hydrocarbon are adjusted so that Y/Z (g/min) satisfies 1.5. Ltoreq. Y/Z. Ltoreq.2.7, where Y (g) is an amount of the multilayered carbon nanotube produced per 1g of the catalyst for carbon nanotube synthesis, and Z (min) is a contact reaction time of the catalyst for carbon nanotube synthesis and the hydrocarbon.
In one embodiment of the method for producing a multilayered carbon nanotube, the hydrocarbon is ethylene.
The dispersion of the present invention contains: the multilayered carbon nanotube of the present invention and a dispersant.
The resin composition of the present invention contains: the multilayered carbon nanotube of the present invention and a resin.
The coating film of the present invention is formed from the resin composition of the present invention.
ADVANTAGEOUS EFFECTS OF INVENTION
By using the multilayered carbon nanotube of the present invention, a resin composition having excellent jet-black properties can be obtained. Therefore, the multilayered carbon nanotube and the method for producing the multilayered carbon nanotube of the present invention can be used in various applications requiring high blackening properties.
Drawings
Fig. 1 is a graph showing the relationship between the outer diameter and the number of the carbon nanotubes obtained in example 1, when any of 300 carbon nanotubes was observed using a transmission electron microscope.
Fig. 2 is a graph showing the relationship between the outer diameter and the number of the carbon nanotubes obtained in example 4, when any of 300 carbon nanotubes are observed by a transmission electron microscope.
Fig. 3 is a graph showing the relationship between the outer diameter and the number of the carbon nanotubes obtained in comparative example 1, when any 300 carbon nanotubes are observed by a transmission electron microscope.
Fig. 4 is a graph showing the relationship between the outer diameter and the number of the carbon nanotubes obtained in comparative example 2, when any of 300 carbon nanotubes was observed by a transmission electron microscope.
Fig. 5 is a graph showing the relationship between the outer diameter and the number of the carbon nanotubes obtained in comparative example 3, when any of 300 carbon nanotubes was observed by a transmission electron microscope.
Fig. 6 is a graph showing the relationship between the outer diameter and the number of the carbon nanotubes obtained in comparative example 4, when any of 300 carbon nanotubes was observed by a transmission electron microscope.
Fig. 7 is a graph showing the relationship between the outer diameter and the number of carbon nanotubes in the case of observing 300 arbitrary carbon nanotubes with a transmission electron microscope for the carbon nanotubes obtained in example 12.
Fig. 8 is a graph showing the relationship between the outer diameter and the number of carbon nanotubes in the case of observing 300 arbitrary carbon nanotubes with a transmission electron microscope for the carbon nanotubes obtained in example 13.
Detailed Description
The multilayered carbon nanotube, the dispersion liquid, the resin composition and the coating film thereof of the present invention will be described in detail below.
(1) Multilayer carbon nanotube (A)
The multilayered carbon nanotube (a) has a cylindrical shape obtained by winding planar graphite. The multi-walled carbon nanotube (A) may have a single-walled carbon nanotube mixed therein. The single-walled carbon nanotube has a structure in which a layer of graphite is wound. The multilayered carbon nanotube (a) has a structure in which two or more layers of graphite are wound. In addition, the sidewall of the multilayered carbon nanotube (a) may not have a graphite structure. For example, a carbon nanotube having a sidewall with an amorphous structure may be used as the multilayered carbon nanotube (a).
The shape of the multilayered carbon nanotube (a) is not limited. The shape may be a needle shape, a cylindrical tube shape, a fishbone shape (fishbone or cup-like), a poker shape (sheet), or a coil shape. In the present embodiment, among them, the shape of the multilayered carbon nanotube (a) is preferably a needle shape or a cylindrical tube shape. The multilayered carbon nanotube (a) may be in a single shape or a combination of two or more shapes.
Examples of the form of the multilayered carbon nanotube (a) include: graphite whiskers, fine carbon, graphite fibers, ultra-fine carbon tubes, carbon fibrils, carbon nanotubes, and carbon nanofibers, but are not limited thereto. The multilayered carbon nanotube (a) may have a single morphology of these or a morphology of two or more kinds combined.
The multilayered carbon nanotube (a) of the present embodiment has an average outer diameter of 10nm or less and a standard deviation of the outer diameter of 4nm or less. By providing the multilayered carbon nanotube (a) with the specific outer diameter, a resin composition having high jet-black properties can be obtained.
The average outer diameter of the multilayered carbon nanotube (a) is preferably 3nm to 10nm, more preferably 4nm to 10nm, and still more preferably 4nm to 8nm, among others, from the viewpoint of ease of dispersion and hue.
The standard deviation of the outer diameter of the multilayered carbon nanotube (a) may be 4nm or less, but is preferably 3nm or less, more preferably 2.5nm or less, among them, from the viewpoint of ease of dispersion and color. The standard deviation of the outer diameter is preferably 0.7nm or more, and more preferably 1.4nm or more.
When the average outer diameter of the carbon nanotubes is X [ nm ] and the standard deviation of the outer diameters of the carbon nanotubes is σ [ nm ], X. + -. σ [ nm ] is preferably 5.0nm or more and X. + -. σ [ nm ] or less and 14.0nm or less, from the viewpoint of obtaining a resin composition having high jet-black property.
In addition, from the viewpoint of obtaining a resin composition having high jet-black properties, X + -2 σ [ nm ] is preferably 2.0nm or more and X + -2 σ or less and 17.0nm, more preferably 2.5nm or more and X + -2 σ or less and 15.5nm, and still more preferably 3.0nm or more and X + -2 σ or less and 12.0nm.
The outer diameter and the average outer diameter of the multilayered carbon nanotube (a) are determined as follows. First, an image was taken while observing the multilayered carbon nanotube (a) with a transmission electron microscope. Next, in the observation photograph, an arbitrary 300 carbon nanotubes (a) were selected and the outer diameters thereof were measured. Next, the average outer diameter (nm) of the multilayered carbon nanotube (a) was calculated as the number average of the outer diameters.
The length of the fiber of the multilayered carbon nanotube (a) of the present embodiment is preferably 0.1 to 150 μm, and more preferably 1 to 10 μm, from the viewpoint of ease of dispersion and hue.
The carbon purity of the multilayered carbon nanotube (a) is represented by the content (mass%) of carbon atoms in the multilayered carbon nanotube (a). The carbon purity is preferably 85 mass% or more, more preferably 90 mass% or more, and still more preferably 95 mass% or more, based on 100 mass% of the multilayered carbon nanotube (a).
In the present embodiment, the multilayered carbon nanotube (a) is generally present as a secondary particle. The shape of the secondary particles may be, for example, a state in which the multi-layered carbon nanotubes (a) which are general primary particles are complexly entangled. The multilayered carbon nanotube (a) may be an aggregate of linear carbon nanotubes. The secondary particles, which are an aggregate of the linear multi-walled carbon nanotubes (a), are more likely to be loosened than the intertwined ones. In addition, the linear form has better dispersibility than the twisted form, and thus can be suitably used as the multilayered carbon nanotube (a).
The multilayered carbon nanotube (a) may be a surface-treated carbon nanotube. The multilayered carbon nanotube (a) may be a carbon nanotube derivative to which a functional group represented by a carboxyl group is added. Further, a multilayered carbon nanotube (a) containing a substance typified by an organic compound, a metal atom, or a fullerene may be used.
The multilayered carbon nanotube (a) of the present embodiment is preferably a carbon nanotube having a small number of layers. In particular, when powder X-ray diffraction analysis is performed, a peak having a half-value width of preferably 3 ° or more and 5.5 ° or less, more preferably more than 5 ° and 5.5 ° or less exists at a diffraction angle 2 θ =25 ° ± 2 °. By using the multilayered carbon nanotube (A) having a small number of layers, the brightness is low and the specular gloss is improved, so that a coating film having high jet-blackness can be obtained.
The layer structure of the multilayered carbon nanotube (a) can be analyzed by powder X-ray diffraction analysis by the following method.
The half-value width of the multilayered carbon nanotube (a) can be determined as follows. First, a predetermined sample holder was filled with a multilayered carbon nanotube (a) so that the surface thereof was flat, and the sample holder was set in a powder X-ray diffraction analyzer, and the irradiation angle of an X-ray source was changed from 5 ° to 80 ° to measure the multilayer carbon nanotube (a). As the X-ray source, cuK α rays are used, for example. The step was 0.010 ° and the measurement time was 1.0 second. The multilayer carbon nanotube (a) can be evaluated by reading the diffraction angle 2 θ at which the peak appears. It is known that graphite generally has a peak detected at around 26 ° 2 θ, and this is a peak generated by interlayer diffraction. Since the multilayered carbon nanotube (a) also has a graphite structure, a peak due to diffraction between graphite layers is detected in the vicinity thereof. However, since the carbon nanotube has a cylindrical structure, its value is different from that of graphite. By the occurrence of a peak at a position whose value 2 θ is 25 ° ± 2 °, it can be judged that the composition comprising not a single layer but a multilayer structure is included. The peak appearing at the position is a peak generated by diffraction between layers of the multilayer structure, and therefore the number of layers of the multilayer carbon nanotube (a) can be judged. Since the number of layers of the single-walled carbon nanotube is only 1, only the single-walled carbon nanotube does not have a peak at a position of 25 ° ± 2 °. However, even a single-walled carbon nanotube is not called a 100% single-walled carbon nanotube, and when a multi-walled carbon nanotube is mixed, a peak may appear at a position where 2 θ is 25 ° ± 2 °.
The multilayered carbon nanotube (a) exhibited a peak at a position of 25 ° ± 2 ° 2 θ. Further, the layer structure can be analyzed from the half width of the peak at 25 ° ± 2 ° detected by powder X-ray diffraction analysis. That is, it is considered that the smaller the half-value width of the peak value is, the larger the number of layers of the multilayered carbon nanotube (a) becomes. Conversely, it is considered that the larger the half-value width of the peak value is, the smaller the number of carbon nanotube layers is.
The multilayer carbon nanotube (A) of the present embodiment has a Raman spectrum of 1560cm -1 ~1600cm -1 G, 1310cm, or -1 ~1350cm -1 When the maximum peak intensity in the range of (3) is D, the G/D ratio is preferably 4.9 to 0.3, more preferably 2.0 to 0.3, and still more preferably 1.0 to 0.5. The G/D ratio of the multilayered carbon nanotube (A) was determined by Raman spectroscopy.
There are various laser wavelengths used in Raman spectroscopy, and 532nm and 632nm are used here. In Raman spectroscopy, it will be at 1590cm -1 The near visible Raman shift, called the G-band from graphite, will be at 1350cm -1 The nearby visible raman shift is called the D-band originating from defects in amorphous carbon or graphite. The higher the G/D ratio, the higher the degree of graphitization.
In addition, 150cm of Raman spectrum -1 ~350cm -1 Referred to as Radial Breathing Mode (RBM), the peaks observed in the region have a correlation with the outer diameter of the carbon nanotube as follows, and the outer diameter of the carbon nanotube can be estimated. Let d (nm) be the outer diameter of the carbon nanotube, and v (cm) be the Raman shift -1 ) Then d =248/v holds. From this consideration, raman spectroscopic analysis at a wavelength of 532nm is carried out at 140cm -1 、160cm -1 、180cm -1 、210cm -1 、270cm -1 、320cm -1 The peaks were observed, i.e., indicating the presence of carbon nanotubes having outer diameters of 1.77nm, 1.55nm, 1.38nm, 1.18nm, 0.92nm, 0.78 nm.
Since the wave number of raman spectroscopy may vary depending on the measurement conditions, the wave number defined here is defined as the wave number ± 10cm -1 And (4) specifying.
[ method for producing multilayered carbon nanotube (A) ]
In the present embodiment, the multilayered carbon nanotube (a) is not particularly limited as long as the average outer diameter of the multilayered carbon nanotube is 10nm or less and the standard deviation of the outer diameter is 4nm or less, and may be a carbon nanotube produced by any method. The multilayered carbon nanotube (a) can be generally produced by a laser ablation method, an arc discharge method, a thermal Chemical Vapor Deposition (CVD) method, a plasma CVD method, and a combustion method. The multilayered carbon nanotube (a) can be produced, for example, by reacting a carbon source with a catalyst in contact at 500 to 1000 ℃ in an atmosphere having an oxygen concentration of 1 vol% or less.
In the present embodiment, the method for producing the multilayered carbon nanotube (a) preferably includes the following steps.
(1) A step of mixing and/or pulverizing a metal salt containing cobalt and magnesium, and then calcining the mixture to obtain a catalyst for synthesizing carbon nanotubes
(2) Contacting the carbon nanotube synthesis catalyst with a carbon source containing at least one selected from the group consisting of hydrocarbons and alcohols under heating to obtain a multi-layered carbon nanotube
As the raw material gas for the carbon source, any conventionally known gas can be used. Examples thereof include hydrocarbons, carbon monoxide, alcohols and the like, and one kind thereof may be used alone or two or more kinds thereof may be used in combination. In the present embodiment, the carbon source preferably contains one or more selected from hydrocarbons and alcohols, and more preferably contains a hydrocarbon. Examples of the hydrocarbon include methane, propane, butane, and acetylene, and among them, ethylene is preferable.
When ethylene is used as the carbon source, the carbon source is preferably reacted with the catalyst at 600 to 800 ℃ in an atmosphere having an oxygen concentration of 1 vol% or less to produce the multilayered carbon nanotube (a), and more preferably, the carbon source is reacted with the catalyst at 650 to 750 ℃ to produce the multilayered carbon nanotube (a).
The amount of hydrocarbon may be appropriately changed depending on the size of the reaction vessel or the amount of catalyst in the reaction vessel, but it is preferable to adjust the amount of catalyst and/or the flow rate of hydrocarbon so that Y/Z (g/min) satisfies 1.5. Ltoreq. Y/Z. Ltoreq.2.7, where Y (g) is the amount of carbon nanotubes produced per 1g of catalyst and Z (min) is the contact reaction time between the catalyst and the hydrocarbon.
Preferably, the catalyst is activated in a reducing gas atmosphere if necessary, and then the raw material gas and the catalyst are brought into contact with each other to react in an atmosphere having an oxygen concentration of 1 vol% or less. Alternatively, the raw material gas may be brought into contact with the catalyst together with the reducing gas to react therewith. The atmosphere having an oxygen concentration of 1 vol% or less is not particularly limited, but is preferably an atmosphere of a rare gas such as argon or an inert gas typified by nitrogen. As the reducing gas used for activating the catalyst, hydrogen or ammonia may be used, but the reducing gas is not limited to these. Hydrogen is particularly preferable as the reducing gas.
As the catalyst, various metals known in the art can be used. Specifically, the metal oxide is obtained by mixing and/or pulverizing an active ingredient represented by cobalt, nickel or iron with a catalyst support represented by magnesium, aluminum or silicon. Particularly preferred are metal oxides obtained by mixing and/or pulverizing metals containing cobalt as an active ingredient and magnesium as a catalyst support. By using cobalt as an active component and magnesium as a catalyst support, a multilayered carbon nanotube having an average outer diameter of 10nm or less and a standard deviation of the outer diameter of 4nm or less can be easily obtained.
As the active ingredients, specifically, there may be mentioned: ammonium iron (III) citrate, iron (II) ammonium sulfate hexahydrate, iron (III) chloride hexahydrate, iron (II) chloride tetrahydrate, iron (III) citrate n-hydrate, iron (III) nitrate nonahydrate, iron (II) oxalate dihydrate, iron (III) oxide, cobalt hydroxide, cobalt (II) acetate tetrahydrate, basic cobalt (II) carbonate, cobalt (II) chloride hexahydrate, cobalt (II) nitrate hexahydrate, cobalt (II) oxide, cobalt (II, III) oxide, cobalt (II) stearate, cobalt (II) sulfate heptahydrate, cobalt (II) sulfide, cobalt (II) acetate, nickel (II) sulfate ammonium hexahydrate, nickel (II) acetate tetrahydrate, nickel (II) chloride hexahydrate, nickel (II) hydroxide, nickel (II) nitrate hexahydrate, nickel (II) oxide, nickel (II) sulfate hexahydrate, and the like. Cobalt hydroxide, cobalt (II) acetate tetrahydrate, iron (III) citrate n hydrate, and iron (III) nitrate nonahydrate are particularly preferable. These active ingredients may be combined in two or more.
The catalyst support is preferably a support containing magnesium, exhibiting adsorption or catalytic activity, and capable of supporting a catalyst metal on the surface of the catalyst support, and may be an organic or inorganic material.
As the magnesium as the catalyst carrier, a conventionally known magnesium compound can be used. Examples are magnesium, magnesium chloride, magnesium hydroxide, magnesium oxide, magnesium sulfate, magnesium acetate tetrahydrate, basic magnesium carbonate, magnesium chloride hexahydrate. Particularly preferably, magnesium acetate tetrahydrate, magnesium hydroxide or magnesium oxide is used.
The catalyst support preferably contains, for example, silica, aluminum, basic aluminum acetate, aluminum bromide, aluminum chloride, aluminum hydroxide, aluminum lactate, alumina, zeolite, titanium oxide, zirconium, calcium oxide, and the like in addition to magnesium. By combining two raw materials having different melting points, fusion of particles with each other can be prevented in the production of a catalyst. For example, by combining an organic substance such as magnesium acetate or aluminum acetate with an inorganic substance such as silica, alumina, zeolite, titanium oxide, zirconium, or magnesium oxide, the catalyst activity can be improved. In particular, when magnesium acetate tetrahydrate is used as a catalyst carrier, silica, zeolite, and alumina are preferably used in combination. Particularly preferred is silica or zeolite.
Examples of the silica, zeolite and alumina used as the catalyst carrier include preferred are eriol (registered trademark) 50, eriol (registered trademark) 130, eriol (registered trademark) 200, eriol (registered trademark) 300, eriol (registered trademark) 380, eriol (registered trademark) AluC, eriol (registered trademark) TiO2P25, alumina C10W, C20, C40, C50, C500, and huta (Beta) zeolite 940HOA, 980HOA, zeolite (mordenlite) 640 a, HSA 320HOA, 350 HOA, HOA 360 a, and HUA 390 manufactured by japan light metal corporation, all of Evonik. Among them, preferred is Aerosil (registered trademark).
When the magnesium content is 100 mol%, the content of silica or aluminum in the catalyst support is preferably 1 mol% to 50 mol%, and more preferably 1 mol% to 25 mol%.
The bulk density of the silica or alumina in the catalyst support is preferably in the range of 0.04g/mL to 0.5g/mL. When silica is used, it is more preferably 0.04 g/mL-0.1 g/mL.
The bulk density is a bulk density before a volume reduction treatment such as deaeration or granulation, and is a value measured in accordance with JIS-K-5101.
The silica or alumina of the catalyst support preferably has a Brunauer Emmett Tellern (BET) specific surface area of 50m 2 /g~1000m 2 Per g, more preferably 150m 2 /g~350m 2 /g。
The catalyst support preferably contains a co-catalyst having an action of enhancing the catalytic action of the catalyst. For example, manganese, molybdenum, and tungsten are preferably contained. Particularly preferred is manganese or molybdenum. By including these promoters in the catalyst support, the catalyst activity or catalyst life can be increased. These cocatalysts may be monomeric or may contain a plurality of them.
When the magnesium content is 100 mol%, the content of the co-catalyst in the catalyst support is preferably 5 mol% to 100 mol%, and more preferably 5 mol% to 30 mol%.
As the manganese salt or molybdenum salt used for the catalyst support, various salts known in the art can be used. Examples thereof include: manganese (II) acetate tetrahydrate, manganese (II) carbonate n hydrate, manganese (II) chloride tetrahydrate, manganese (II) nitrate hexahydrate, manganese (IV) oxide, manganese (II) sulfate pentahydrate, ammonium molybdate, molybdenum, potassium molybdate, hexaammonium heptamolybdate tetrahydrate, molybdenum (V) chloride, molybdenum (VI) oxide, molybdenum (IV) sulfide, ammonium tungstate para-pentahydrate, potassium tungstate, sodium tungsten (VI) dihydrate, tungsten (VI) oxide, and the like. Manganese (II) acetate tetrahydrate, manganese (II) carbonate n hydrate, ammonium molybdate and molybdenum (VI) oxide are particularly preferred.
The raw materials of the catalyst support are preferably homogeneously mixed. The mixing may be wet or dry, but when a salt insoluble in water is used, dry mixing is preferable. When the raw materials are mixed in a wet manner, they are preferably mixed after being dried in the range of 100 to 200 ℃.
The catalyst carrier preferably has a low moisture content. The water content is preferably 5% by mass or less, and more preferably 3% by mass or less, when the catalyst carrier is 100% by mass. The amount of water in the catalyst carrier can be measured, for example, by using a heat drying type moisture meter (MS-70, A & D Co., ltd.).
The particle size of the catalyst support is preferably small. Specifically, the particle size distribution is preferably 1.0 to 10.0 μm, more preferably 1.0 to 5.0 μm in D50 (μm). The D90 (. Mu.m) is preferably 5.0 to 70.0. Mu.m, more preferably 5.0 to 20.0. Mu.m.
The particle size distributions D50 (. Mu.m) and D90 (. Mu.m) of the catalyst carrier were determined as follows. First, the particle size distribution of the catalyst carrier was measured by a laser diffraction dry particle size distribution measuring apparatus. The particle diameter at 50vol% of the cumulative distribution in the measurement results can be calculated as D50 (. Mu.m), and the particle diameter at 90vol% of the cumulative distribution can be calculated as D90 (. Mu.m).
As a method for reducing the particle diameter of the catalyst carrier, various conventionally known methods can be used. Among them, a pulverizer which can apply a compressive force, an impact force, a shearing force or a frictional force to the catalyst carrier is preferably used.
The pulverizer is a device that applies a force such as a compressive force, an impact force, a shearing force, or a frictional force to a sample to pulverize the sample. As the device for carrying out the micronization, there may be used a pulverizer such as a mortar, pin mill, hammer mill, pulverizer (pulverizer), attritor, jet mill, cutter, ball mill, bead mill, colloid mill, conical mill, disk mill, crusher, vander mill (Wonder), vibration mill, ultrasonic homogenizer, etc. Preferably, the catalyst particles are easily compounded, mechanically alloyed and amorphized by an attritor, pin mill, hammer mill, jet mill, cutter, ball mill, bead mill, wander mill or vibration mill. Particularly preferred are an attritor, a ball mill, a bead mill, and a vibration mill using beads as a pulverization medium.
As the beads as the pulverization medium, various beads known in the art can be used. Such as steel beads, zirconia beads, alumina beads, glass beads. Among them, steel balls having a large specific gravity or zirconia beads having a high hardness are preferably used.
As the diameter of the beads, various conventionally known beads can be used, but from the viewpoint of workability, it is preferable to use beads having a diameter of 1mm to 10 mm. More preferably, beads of 2mm to 5mm are used.
The catalyst is preferably prepared by uniformly mixing and/or pulverizing the active ingredient, the catalyst support and the co-catalyst ingredient. As the method of mixing and/or pulverizing, various conventionally known methods can be used. As the device for mixing and/or pulverizing, the same device as the above-mentioned pulverizer can be cited.
The catalyst is preferably an oxide obtained by mixing and pulverizing an active component, a catalyst support and a metal salt as a promoter component, and then calcining the mixture in air.
The calcination temperature varies depending on the oxygen concentration during calcination, but is preferably 300 to 900 ℃, more preferably 300 to 750 ℃ in the presence of oxygen.
The catalyst is preferably calcined and the solid material is ground to a particle size D50 of 50 μm or less, more preferably less than 20 μm. By pulverizing the solid matter to make the particle size uniform, a homogeneous catalyst can be obtained.
(2) Resin composition (B)
The resin composition (B) of the present embodiment contains at least the multilayered carbon nanotube (a) and the resin (C). The resin composition of the present embodiment can be suitably used for forming a coating film having high jet-blackness by containing the multilayered carbon nanotube (a) of the present invention.
In order to obtain the resin composition (B) of the present embodiment, it is preferable to perform a treatment of dispersing the multilayered carbon nanotubes (a) and the resin (C) in a solvent. The equipment used for the treatment is not particularly limited. Examples of the equipment include: paint conditioner ("dynamics-MILL"), manufactured by Redmond, inc.), ball MILL, sand MILL ("Dyno-Mill"), manufactured by shinmar EnterPRISES, inc., attritor, pearl MILL ("DCP Mill"), manufactured by Airlicho (EIRICH), ultrasonic homogenizer ("advanced digital silicon) (registered trademark), MODEL (MODEL) 450DA, manufactured by Bentoni (BRANSON), korea ball MILL (Co-ball MILL), basket ball MILL (ball MILL), homomixer (" Cruby "), homogenizer (" Millimix "), manufactured by M Technique, inc., wet jet MILL (" Jenius) PY, "manufactured by Jennius (Jennius), nano MILL (" nano MILL, "manufactured by Nanommizer), and roller MILL (" horse MILL "(horse), manufactured by Nanommizer, inc.).
In addition, in order to obtain the resin composition (B), a high-speed stirrer may be used. Examples of the high-speed mixer include, but are not limited to, HOMO DISPER (HOMO DISPER) (manufactured by primpex corporation), filmix (filmix) (manufactured by primpex corporation), dissolver (dissolver) (manufactured by uphole manufacturing company), and seapu (Hyper) HS (nozawa fine science (Ashizawa Finetech)).
Resin (C)
The resin (C) is selected from natural resins and synthetic resins. The resin (C) may be a separate resin. The resin (C) may be two or more selected from natural resins and synthetic resins. Two or more kinds of resins may be used in combination.
Examples of natural resins include: natural rubber, gelatin, rosin, shellac, polysaccharides, and natural asphalt, but are not limited thereto. Examples of the synthetic resin include, but are not limited to, phenol resins, alkyd resins, petroleum resins, vinyl resins, olefin resins, synthetic rubbers, polyester resins, polyamide resins, acrylic resins, styrene resins, epoxy resins, melamine resins, polyurethane resins, amino resins, amide resins, imide resins, fluorine resins, vinylidene fluoride resins, vinyl chloride resins, acrylonitrile-Butadiene-Styrene (ABS) resins, polycarbonates, silicone resins, nitrocellulose, rosin-modified phenol resins, and rosin-modified polyamide resins.
From the viewpoint of light resistance, it is preferable that these resins contain at least one of an acrylic resin and a polyester resin. In this case, it is also preferable that the base paint contains at least one of an acrylic resin and a polyester resin.
The water-soluble resin used in the resin composition (B) of the present embodiment is preferably a water-soluble resin having an acid value of 20mgKOH/g to 70mgKOH/g and a hydroxyl value of 20mgKOH/g to 160 mgKOH/g. Specifically, polyester resins, acrylic resins, and polyurethane resins are particularly suitable for use as the water-soluble resin.
The polyester resin is a resin used with a polyhydric alcohol and a polybasic acid as raw materials. The acid value of the polyester resin is 20mgKOH/g to 70mgKOH/g, preferably 25mgKOH/g to 60mgKOH/g, and particularly preferably 30mgKOH/g to 55mgKOH/g. The hydroxyl value of the polyester resin is 20mgKOH/g to 160mgKOH/g, preferably 80mgKOH/g to 130mgKOH/g.
In the present embodiment, the acid value means the mass (mg) of potassium hydroxide required for neutralizing 1g of the resin. The hydroxyl value means the mass (mg) of potassium hydroxide required for reacting the hydroxyl group of a resin with phthalic anhydride to neutralize 1g of the resin with an acid required for the reaction.
In the present embodiment, the acid value and the hydroxyl value of the resin can be measured by a method in accordance with JIS K0070.
The water-soluble polyester resin can be easily obtained by a known esterification reaction. The water-soluble polyester resin is produced from a polyhydric alcohol and a polybasic acid as raw materials. The raw material may be a compound constituting a general polyester resin. Oils and fats may be added to the water-soluble polyester resin as needed.
Examples of the polyol include: ethylene glycol, 1, 2-propylene glycol, 1, 3-butylene glycol, 1, 4-butylene glycol, 1, 6-hexanediol, diethylene glycol, dipropylene glycol, neopentyl glycol, triethylene glycol, hydrogenated bisphenol A, glycerin, trimethylolethane, trimethylolpropane, pentaerythritol, and dipentaerythritol, but not limited thereto. These polyols may be used alone or in combination of two or more.
Examples of the polybasic acid include: phthalic anhydride, isophthalic acid, terephthalic acid, succinic anhydride, adipic acid, azelaic acid, sebacic acid, maleic anhydride, fumaric acid, itaconic acid, and trimellitic anhydride, but are not limited thereto. These polybasic acids may be used alone or in combination of two or more.
Examples of the oils and fats include, but are not limited to, soybean oil, coconut oil, safflower oil, bran oil, castor oil, tung oil, linseed oil, tall oil, and fatty acids obtained from these oils and fats.
The acrylic resin is a resin using a vinyl monomer as a raw material. The acid value of the acrylic resin is 20mgKOH/g to 70mgKOH/g, preferably 22mgKOH/g to 50mgKOH/g, and particularly preferably 23mgKOH/g to 40mgKOH/g. The hydroxyl value of the acrylic resin is 20mgKOH/g to 160mgKOH/g, preferably 80mgKOH/g to 150 mgKOH/g.
The water-soluble acrylic resin can be easily obtained by a known solution polymerization method or other methods. The water-soluble acrylic resin is produced from a vinyl monomer as a raw material. The raw material may be a compound constituting a general acrylic resin. In addition, in the method, an organic peroxide may be used as an initiator for polymerization.
Examples of the vinyl monomer include: ethylenically unsaturated carboxylic acids represented by acrylic acid, methacrylic acid, itaconic acid, maleic acid, fumaric acid, and crotonic acid; alkyl esters of acrylic acid or methacrylic acid represented by methyl, ethyl, propyl, butyl, isobutyl, tert-butyl, 2-ethylhexyl, lauryl, cyclohexyl and stearyl; hydroxyalkyl esters of acrylic acid or methacrylic acid represented by 2-hydroxyethyl, 2-hydroxypropyl, 3-hydroxypropyl, polyethylene glycol having a molecular weight of 1000 or less; amides of acrylic acid or methacrylic acid; or alkyl ethers thereof, but not limited thereto. Examples thereof include: acrylamide, methacrylamide, N-methylolacrylamide, diacetone acrylamide, diacetone methacrylamide, N-methoxymethyl methacrylamide and N-butoxymethyl acrylamide, but are not limited thereto.
Further, glycidyl (meth) acrylate having an epoxy group is exemplified. Further, monomers containing a tertiary amino group are also included. Examples thereof include, but are not limited to, N-dimethylaminoethyl (meth) acrylate and N, N-diethylaminoethyl (meth) acrylate. Further, there may be mentioned: aromatic monomers represented by styrene, α -methylstyrene, vinyltoluene and vinylpyridine; acrylonitrile; methacrylonitrile; vinyl acetate; and monoalkyl esters or dialkyl esters of maleic acid or fumaric acid, but are not limited thereto. Examples of the organic peroxide include: acyl peroxides (e.g., benzoyl peroxide), alkyl hydroperoxides (e.g., t-butyl hydroperoxide and p-methane hydroperoxide), and dialkyl peroxides (e.g., di-t-butyl peroxide), but are not limited thereto.
The polyurethane resin is a resin using a polyol and a polyisocyanate as raw materials. The acid value of the polyurethane resin is 20mgKOH/g to 70mgKOH/g, preferably 22mgKOH/g to 50mgKOH/g, and particularly preferably 23mgKOH/g to 35mgKOH/g. The hydroxyl value of the polyurethane resin is 20mgKOH/g to 160mgKOH/g, preferably 25mgKOH/g to 50mgKOH/g.
The water-soluble polyurethane resin can be easily obtained by addition polymerization of a polyol and a polyisocyanate. The raw materials may be a polyol and a polyisocyanate constituting a general polyurethane resin.
As the polyhydric alcohol, there may be mentioned: polyester polyols, polyether polyols and acrylic polyols, but are not limited thereto. Further, as the polyisocyanate, there may be mentioned: benzene diisocyanate, toluene diisocyanate, xylylene diisocyanate, bis-phenylene diisocyanate, naphthalene diisocyanate, diphenylmethane diisocyanate, isophorone diisocyanate, cyclopentylene diisocyanate, cyclohexylene diisocyanate, methylcyclohexylene diisocyanate, dicyclohexylmethane diisocyanate, trimethylene diisocyanate, tetramethylene diisocyanate, pentamethylene diisocyanate, hexamethylene diisocyanate, propylene diisocyanate, ethyl ethylene diisocyanate, and trimethylhexane diisocyanate, but is not limited thereto.
The water-soluble polyester resin, acrylic resin, and polyurethane resin are rendered water-soluble by neutralization with a basic substance. In this case, it is preferable to use a basic substance in an amount capable of neutralizing 40 mol% or more of the acidic groups contained in the water-soluble resin. Examples of the basic substance include: ammonia, dimethylamine, trimethylamine, diethylamine, triethylamine, propylamine, triethanolamine, N-methylethanolamine, N-aminoethylethanolamine, N-methyldiethanolamine, morpholine, monoisopropanolamine, diisopropanolamine and dimethylethanolamine, but not limited thereto.
The number average molecular weight of the water-soluble resin is not particularly limited. The number average molecular weight is preferably 500 to 50,000, more preferably 800 to 25,000, and particularly preferably 1,000 to 12,000.
In addition, the resin (C) is classified into a type having curability and a paint type. In the present embodiment, a type of resin having curability is suitably used. The curable resin (C) is used together with an amino resin represented by a melamine resin or a crosslinking agent represented by a (block) polyisocyanate compound, an amine compound, a polyamide compound, and a polycarboxylic acid. After the resin (C) and the bridging agent are mixed, the mixture is heated or left at room temperature to undergo a curing reaction. Further, a resin of a type not having curability may be used as the resin for forming the coating film, or may be used in combination with a resin of a type having curability.
The resin composition (B) of the present embodiment may contain at least the multilayered carbon nanotube (a) and the resin (C), and may further contain other components as needed.
Examples of the other components include a dispersant and a solvent.
As the dispersant, a surfactant, a resin type dispersant, or an organic pigment derivative can be used. Surfactants are mainly classified into anionic, cationic, nonionic and amphoteric. Depending on the properties required for the dispersion of the multilayered carbon nanotube (a), an appropriate kind of dispersant can be used in an appropriate blending amount. The dispersant is preferably a resin type dispersant.
When the anionic surfactant is selected, the kind thereof is not particularly limited. Specifically, the following are listed: fatty acid salts, polysulfonic acid salts, polycarboxylates, alkylsulfuric acid ester salts, alkylarylsulfonic acid salts, alkylnaphthalenesulfonic acid salts, dialkylsulfonic acid salts, dialkylsulfosuccinic acid salts, alkylphosphoric acid salts, polyoxyethylene alkyl ether sulfates, polyoxyethylene alkylaryl ether sulfates, naphthalenesulfonic acid formaldehyde condensates, polyoxyethylene alkylphosphoric acid sulfonates, glycerol borate fatty acid esters, and polyoxyethylene glycerol fatty acid esters, but are not limited thereto. Further, specific examples thereof include: sodium dodecylbenzenesulfonate, sodium laurylsulfate, sodium polyoxyethylene lauryl ether sulfate, polyoxyethylene nonylphenyl ether sulfate, and sodium salt of a β -naphthalenesulfonic acid formaldehyde condensate, but are not limited thereto.
Further, as the cationic surfactant, there are alkylamine salts and quaternary ammonium salts. Specifically, there may be mentioned: stearyl amine acetate, trimethyl coco ammonium chloride, trimethyl tallow ammonium chloride, dimethyl dioleyl ammonium chloride, methyl oleyl diethanol chloride, tetramethyl ammonium chloride, lauryl pyridine bromide, lauryl pyridine disulfide, cetyl pyridine bromide, 4-alkylmercapto pyridine, poly (vinylpyridine) -dodecyl bromide, and dodecylbenzyl triethyl ammonium chloride, but is not limited thereto. The amphoteric surfactant may be, for example, an aminocarboxylate, but is not limited thereto.
Further, examples of the nonionic surfactant include: polyoxyethylene alkyl ethers, polyoxyalkylene derivatives, polyoxyethylene phenyl ethers, sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters, and alkylallyl ethers, but are not limited thereto. Specific examples thereof include: polyoxyethylene lauryl ether, sorbitan fatty acid ester, and polyoxyethylene octylphenyl ether, but are not limited thereto.
The surfactant selected is not limited to a single surfactant. Therefore, two or more surfactants may be used in combination. For example, a combination of an anionic surfactant and a nonionic surfactant, or a combination of a cationic surfactant and a nonionic surfactant can be used. The amount of the surfactant component to be blended in this case is preferably an appropriate amount for each surfactant component. The combination is preferably a combination of an anionic surfactant and a nonionic surfactant. The anionic surfactant is preferably a polycarboxylate. The nonionic surfactant is preferably polyoxyethylene phenyl ether.
As the resin type dispersant, specifically, polyurethane; a polycarboxylate of a polyacrylate; unsaturated polyamides, polycarboxylic acids, polycarboxylic acid (partial) amine salts, polycarboxylic acid ammonium salts, polycarboxylic acid alkylamine salts, polysiloxanes, long-chain polyaminoamide phosphates, and hydroxyl group-containing polycarboxylates, and modifications thereof; an oily dispersant of an amide or a salt thereof formed by the reaction of a polymer of a lower alkyleneimine and a polyester having a free carboxyl group; a (meth) acrylic acid-styrene copolymer, a (meth) acrylic acid- (meth) acrylic acid ester copolymer, a styrene-maleic acid copolymer, a water-soluble resin or a water-soluble polymer compound represented by polyvinyl alcohol and polyvinylpyrrolidone; a polyester resin; a modified polyacrylate resin; ethylene oxide/propylene oxide addition compounds; and phosphate ester resins, but are not limited thereto. These may be used alone or in combination of two or more, but are not necessarily limited thereto.
Among the dispersants, a resin type dispersant having an acidic functional group such as a polycarboxylic acid is preferable. This is because the resin-type dispersant reduces the viscosity of the dispersion composition with a small addition amount and improves the spectral transmittance of the dispersion composition. The resin type dispersant is preferably used in an amount of about 3 to 300% by mass based on the multilayered carbon nanotube (a). From the viewpoint of film formability, the amount of the organic solvent is more preferably about 5 to 100 mass%.
Examples of commercially available resin-type dispersants include: andthe respective portions of the first and second images may be selected from the group consisting of orange-red (ANTI-tera) (registered trademark) -U/U100, orange-red (ANTI-tera) (registered trademark) -204, orange-red (ANTI-tera) (registered trademark) -250, dikedbick (DISPERBYK) (registered trademark) -102, dikedbick (DISPERBYK) (registered trademark) -103, dikedbick (DISPERBYK) (registered trademark) -106, dikedbick (DISPERBYK) (registered trademark) -108, dikedbick (DISPERBYK) (registered trademark) -109, dikedbick (DISPERBYK) (registered trademark) -110/111, dikedbick (DISPERBYK) (registered trademark) -145, dikedbck (seperbyk) (registered trademark) -142, dikedbybek (rbydbydbyk) (registered trademark) -168, dikedbyking (DISPERBYK) (registered trademark) -118, dikedbyk (sepyk) (registered trademark) -167, rbybeck) (registered trademark) -142, rbybekedbyk (rbyk) (registered trademark) -142, rbydbybeck) (registered trademark) -168, rbybeck (rbyk) (registered trademark) -142, rbydbydbyk) (registered trademark) -140, rbydbyk) (registered trademark) -142, rbydbydbybeck) (registered trademark) -140, rbybeck (rbyk) (registered trademark) -140, rbydbyk) (registered trademark) -140, rbydbybeck) (registered trademark) -142, rbybeck (rbydbydbydbydbydbydbyk) (registered trademark) -108, rbybeck (diskeb) (registered trademark) -108, diskedbybeck) (registered trademark), or, DISPERBYK (DISPERBYK) (registered trademark) -170/171, DISPERBYK (DISPERBYK) (registered trademark) -174, DISPERBYK (DISPERBYK) (registered trademark) -180, DISPERBYK (DISPERBYK) (registered trademark) -182, DISPERBYK (DISPERBYK) (registered trademark) -184, DISPERBYK (DISPERBYK) (registered trademark) -185, DISPERBYK (DISPERBYK) (registered trademark) -187, DISPERBYK (DISPERBYK) (registered trademark) -190, DISPERBYK (DISPERBYK) (registered trademark) -191, DISPERBYK (DISPERBYK) (registered trademark) -193, DISPERBYK (DISPERBYK) (registered trademark) -192, DISPERBYK (DISPERBYK) (registered trademark) -193, and the like DISPERBYK (DISPERBYK) (registered trademark) -194N, DISPERBYK (DISPERBYK) (registered trademark) -198, DISPERBYK (DISPERBYK) (registered trademark) -199, DISPERBYK (DISPERBYK) (registered trademark) -2000, DISPERBYK (DISPERBYK) (registered trademark) -2001, DISPERBYK (DISPERBYK) (registered trademark) -2008, DISPERBYK (DISPERBYK) (registered trademark) -2009, DISPERBYK (DISPERBYK) (registered trademark) -2010, DISPERBYK (DISPERBYK) (registered trademark) -2013, DISPERBYK (DISPERBYK) (registered trademark) -2015, DISPERBYK (DISPERBYK) (registered trademark) -2022, DISPERBYK (DISPERBYK) (registered trademark) -2025, DISPERBYK (DISPERBYK) (registered trademark) -2050, DISPERBYK (DISPERBYK) (registered trademark) -2096, DISPERBYK (DISPERBYK) (registered trademark) -2150, DISPERBYK (DISPERBYK) (registered trademark) -2152, DISPERBYK (DISPERBYK) (registered trademark) -2155, DISPERBYK (DISPERBYK) (registered trademark) -2163, DISPERBYK (DISPERBYK) (registered trademark) -2164, DISPERBYK (DISPERBYK) (registered trademark) -2200, DISPERBYK (BYK) (registered trademark) -104/104S 104 BYK (registered trademark) -P105, BYK (registered trademark) -9076, BYK (registered trademark) -9077, BYK (registered trademark) -220S, solipesse (solspere) -3000, 5000, 9000, 11200, 12000, 13240, 13650, 13940, 16000, 17000, 18000, 20000, 21000, 24000GR, 26000, 27000, 28000, 32000, 32500, 32550, 32600, 33000, 34750, 35100, 35200, 36000, 36600, 37500, 38500, 39000, 41000, 41090, 43000, 44000, 46000, 47000, 53095, 55000, 56000, 71000 and 76500, dispere (disx) (registered trademark) manufactured by BASF ) PA4550, dispex (registered trademark) eut (Ultra) PA4560, dispex (registered trademark) potter (Ultra) PX4575, dispex (registered trademark) potter (Ultra) PX4585, efka (registered trademark) FA4608, efka (Efka) (registered trademark) FA4620, efka (Efka) (registered trademark) FA4644, efka (Efka) (registered trademark) FA4654, efka (Efka) (registered trademark) FA4663, efka (Efka) (registered trademark) FA4665, efka (Efka) (registered trademark) FA4666, efka (Efka) (registered trademark) FA4672, efka (registered trademark) FA4672, and edika (Efka) (registered trademark) PX4575 an Efka (Efka) (registered trademark) FA4673, an Efka (Efka) (registered trademark) PA4400, an Efka (Efka) (registered trademark) PA4401, an Efka (Efka) (registered trademark) PA4403, an Efka (Efka) (registered trademark) PA4450, an Efka (Efka) (registered trademark) PU4063, an Efka (Efka) (registered trademark) PX4300, an Efka (Efka) (registered trademark) PX4310, an Efka (Efka) (registered trademark) PX4320, an Efka (Efka) (registered trademark) PX4330, an Efka (Efka) (registered trademark) PX4340, an Efka (Efka) (registered trademark) PX4700, a PX 60, and a, averme card (Efka) (registered trademark) PX4701, averme card (Efka) (registered trademark) PX4731, averme card (Efka) (registered trademark) PX4732, averme card (Efka) (registered trademark) PA4560, averme card (Efka) (registered trademark) PX4575, averme card (Efka) (registered trademark) PX4585, efka (Efka) (registered trademark) FA4600, efka (Efka) (registered trademark) FA4601, floren (Flowten) DOPA-15B, floren (Flowten) DOPA-15BHFS, flowten (Flowten) DOPA-17HF 4601, manufactured by Kyoho chemical Co., ltd Flowen (Flowen) DOPA-22, flowen (Flowen) DOPA-35, flowen (Flowen) G-700, flowen (Flowen) G-820XF, flowen (Flowen) GW-1500, flowen (Flowen) G-100SF, flowen (Flowen) AF-1000, flowen (Flowen) AF-1005, flowen (Flowen) KDG-2400, flowen (Flowen) D-90, and Ajispa (Ajisper) PA111, PN411, PB821, PB822, PB824, PB881 manufactured by Ajisoto Fine-Techno, however, the present invention is not limited to these examples.
Examples of the organic pigment derivative include an organic pigment derivative having an acidic functional group represented by the following general formula (2) and a triazine derivative having an acidic functional group represented by the following general formula (1).
[ solution 1]
General formula (1)
The symbols in the formula represent the following meanings.
Q 1 : an organic pigment residue, orAnthraquinone residue, or heterocyclic ring which may have substituent(s), or aromatic ring which may have substituent(s)
R 1 :-O-R 2 、-NH-R 2 Halogen radical, -X 1 -R 2 、-X 2 -Y 1 -Z 1 (R 2 Represents a hydrogen atom or an alkyl or alkenyl group which may have a substituent(s)
X 1 :-NH-、-O-、-CONH-、-SO 2 NH-、-CH 2 NH-、-CH 2 NHCOCH 2 NH-or-X 3 -Y 1 -X 4 -(X 3 And X 4 Each independently represents-NH-or-O-)
X 2 :-CONH-、-SO 2 NH-、-CH 2 NH-, -NHCO-or-NHSO 2 -
Y 1 : an alkylene group which may have a substituent consisting of 1 to 20 carbon atoms, an alkenylene group which may have a substituent, or an arylene group which may have a substituent
Z 1 :-SO 3 M and COOM (M represents 1 equivalent of a cation having a valence of 1 to 3)
Q as said general formula (1) 1 The organic pigment residue in (1) includes: pigments or dyes such as phthalocyanine-based pigments, azo-based pigments, quinacridone-based pigments, dioxazine-based pigments, anthrapyrimidine-based pigments, anthanthrone-based pigments, indanthrone-based pigments, flavone-based pigments, and triphenylmethane-based pigments.
Q as said general formula (1) 1 Examples of the heterocyclic ring or aromatic ring in (1) include: thiophene, furan, pyridine, pyrazole, pyrrole, imidazole, isoindoline, isoindolinone, benzimidazolone, benzothiazole, benzotriazole, indole, quinoline, carbazole, acridine, benzene, naphthalene, anthracene, fluorene, phenanthrene and the like.
General formula (2)
Q 2 -(-X 5 -Z 2 ) n
The symbols in the formula represent the following meanings.
Q 2 : organic pigment residues or anthraquinone residues
X 5 : direct bond, -NH-, -O-, -CONH-、-SO 2 NH-、-CH 2 NH-、-CH 2 NHCOCH 2 NH-or-X 6 -Y 2 -X 7 -(X 6 And X 7 Each independently represents-NH-or-O-, Y 2 Represents an alkylene group or an arylene group which may have a substituent
Z 2 :-SO 3 M and-COOM (M represents 1 equivalent of a cation having a valence of 1 to 3)
n: an integer of 1 to 4
Examples of the organic dye residue in Q2 of the general formula (2) include: pigments or dyes such as phthalocyanine-based pigments, azo-based pigments, quinacridone-based pigments, dioxazine-based pigments, anthrapyrimidine-based pigments, anthanthrone-based pigments, indanthrone-based pigments, xanthone-based pigments, perylene-based pigments, perinone-based pigments, thioindigo-based pigments, isoindolinone-based pigments, and triphenylmethane-based pigments.
The resin composition (B) may contain a solvent. As the solvent, an aqueous solvent and an organic solvent may be used.
The aqueous solvent is water or a solvent containing water. As the aqueous solvent, an aqueous liquid can be used. Specific examples of the water-soluble liquid include water-soluble pyrophoric liquids typified by acetaldehyde, propylene oxide, acetone, pyridine, methyl alcohol, ethyl alcohol, n-propyl alcohol, isopropyl alcohol, acetic acid, propionic acid, acrylic acid, ethylene glycol, and glycerin.
Among the organic solvents, organic solvents having a boiling point of 50 to 250 ℃ can be easily used. The organic solvent is excellent in workability at the time of coating and drying properties before and after curing. Specific examples of the solvent include: alcohol solvents represented by methanol, ethanol and isopropyl alcohol; ketone solvents represented by acetone, butyl diglycol acetate and Methyl Ethyl Ketone (MEK); ester solvents represented by ethyl acetate and butyl acetate; ether solvents represented by dibutyl ether, ethylene glycol, and monobutyl ether; and bipolar aprotic solvents typified by N-methyl-2-pyrrolidone, but the solvent is not limited thereto. These solvents may be used alone or in combination of two or more.
Aromatic hydrocarbon solvents represented by toluene, xylene, sobesol (SOLVESSO) #100 (manufactured by eastern fuel general-purpose company) and sobesol (SOLVESSO) #150 (manufactured by eastern fuel general-purpose company) may also be used; aliphatic hydrocarbon solvents represented by hexane, heptane, octane and decane; or amide solvents represented by cellosolve acetate, ethyl cellosolve, and butyl cellosolve. These solvents may be used alone or in combination of two or more.
If necessary, additives may be appropriately added to the solvent within a range not to impair the object of the present embodiment. Examples of additives include: pigments, wetting and penetrating agents, anti-skinning agents, ultraviolet absorbers, antioxidants, crosslinking agents, preservatives, mildewproofing agents, viscosity modifiers, pH modifiers, leveling agents, and antifoaming agents, but are not limited thereto.
(3) Film (D)
The coating film of the present embodiment is a coating film formed from the resin composition (B) of the present embodiment, and includes a plurality of layers of carbon nanotubes (a) and a resin (C). The substrate (E) is disposed below the coating film (D), but the substrate may be removed after the coating film (D) is formed.
The coating film (D) of the present embodiment has high jet-black properties by containing the multilayered carbon nanotube (a).
The coating film (D) of the present embodiment can be formed by applying the resin composition (B) by a general technique. Specific examples of the technique include a wet coating method including casting, spin coating, dip coating, bar coating, spraying, blade coating, slot die coating, gravure coating, reverse coating, screen printing, stencil coating, print transfer, and spraying, but are not limited thereto. By applying the resin composition (B) to the substrate (E) by the above-mentioned technique, a coating film can be formed.
The addition rate of the multilayered carbon nanotube (a) in the coating film (D) may be selected as appropriate depending on the application. The addition rate is preferably in the range of 0.1 to 30% by mass, more preferably 1 to 25% by mass, and still more preferably 2 to 15% by mass. Particularly, when the addition rate is in the above range, a coating film having excellent jet-black property can be obtained.
Carbon black may be added to the coating film (D) in addition to the multilayered carbon nanotube (a) as long as the object of the present invention is not hindered. Specific examples of the carbon black include ketjen black, acetylene black, furnace black and channel black. Carbon black may be a by-product in the production of a synthesis gas containing hydrogen and carbon monoxide by partially oxidizing a hydrocarbon represented by naphtha in the presence of hydrogen and oxygen. In addition, carbon black may also oxidize or reduce the by-products. The above does not limit the carbon black of the present invention. These carbon blacks may be used alone or in combination of two or more. From the viewpoint of improving the degree of blackness, it is preferable to use carbon black having an average particle diameter of 20nm or less and a dibutyl phthalate (DBP) oil absorption of 80mL/100g or less. In the present embodiment, the DBP oil absorption means an amount (mL) of dibutyl phthalate (DBP) that can be contained in 100g of carbon black. The DBP oil absorption is a measure for quantifying the structure of carbon black. The structure is a complex, agglomerated morphology resulting from chemical or physical bonding between the carbon black particles.
The average particle diameter of carbon black was determined in the same manner as the outer diameter of the multilayered carbon nanotube (A). Specifically, the carbon black was observed by a transmission electron microscope and photographed. Then, in the observation photograph, arbitrary 300 carbon blacks were selected and the particle diameters of the carbon blacks were measured. Next, the average particle diameter (nm) of the carbon black was calculated as the number average of the particle diameters.
The amount of carbon black used is preferably 1 to 25 parts by mass, more preferably 1 to 10 parts by mass, and still more preferably 1 to 5 parts by mass, per 100 parts by mass of the multilayered carbon nanotube (a).
The film thickness of the coating film (D) is preferably 5 μm or more, more preferably 10 μm or more.
As for the coating film (D), a transparent layer may be further formed on the coating film (D). By forming the transparent layer, a coating film (D) having gloss, light resistance and jet-black property can be obtained.
The brightness (L) exhibited by the coating film (D) is preferably 5.7 or less, more preferably 5.5 or less, further preferably 5.3 or less, and particularly preferably 5.2 or less. The luminance (L) can be obtained by measurement using a colorimeter. The measurement was performed on the surface of the coating film (D) from the side of the surface on which the coating film (D) was formed. As the color difference meter, a spectrocolorimeter (spectrocolorimeter) SE6000 manufactured by nippon electrochrome (nipponshoku) corporation may also be used.
The 60 ° specular gloss of the coating film (D) is preferably 60 or more, more preferably 80 or more, and further preferably 85 or more. As the gloss meter, a gloss meter GM-26D (manufactured by color research institute in village) was also used.
Substrate (E)
The base material (E) for forming the coating film (D) in the present embodiment is not particularly limited. Examples of the material of the substrate (E) include: metals represented by iron, aluminum, copper, or alloys thereof; inorganic materials typified by glass, cement, and concrete; resins typified by polyethylene resin, polypropylene resin, ethylene-vinyl acetate copolymer resin, polyamide resin, acrylic resin, vinylidene chloride resin, polycarbonate resin, polyurethane resin, and epoxy resin; plastic materials typified by various Fiber reinforced plastics (FPC); wood; and natural materials or synthetic materials typified by fibrous materials (including paper and cloth), but are not limited thereto.
Among the above materials, metals represented by iron, aluminum, copper, or alloys thereof are preferable. Further, a resin containing a pigment represented by carbon black and carbon nanotubes is also preferable.
The shape of the substrate (E) may be a plate, a film, a sheet or a molded body. Examples of the method for producing the molded article include injection molding methods represented by insert injection molding, in-mold molding, two-shot (over mold) molding, two-shot injection molding, core-back (back) injection molding, and sandwich injection molding; extrusion molding methods typified by a T-die lamination method, a multilayer inflation method, a coextrusion method, and an extrusion coating method; and other molding methods typified by multilayer blow molding, multilayer calender molding, multilayer press molding, slush molding (slush) molding, and melt casting.
(4) Multi-layered Carbon Nanotube (CNT) dispersion (F)
The method for producing the resin composition (B) of the present embodiment is not particularly limited, and one method includes a method of preparing the CNT dispersion liquid (F) and adding a resin to the CNT dispersion liquid (F). The CNT dispersion liquid (F) contains at least the multilayered carbon nanotube (a) and a dispersant, and usually further contains a solvent. Further, the dispersion (F) does not contain the resin (C).
In order to obtain the CNT dispersion liquid (F), it is preferable to perform a treatment of dispersing the multilayered carbon nanotube (a) in a solvent. The equipment used for the treatment is not particularly limited. Examples of the equipment include: paint conditioners ("DYNO-MILL") manufactured by devil corporation), ball MILLs, sand MILLs ("donuo-MILL") manufactured by shin maruenterprises corporation, attritors ("DCP MILLs") manufactured by pearl MILLs ("EIRICH"), ultrasonic homogenizers ("advanced digital sonier" (registered trademark), MODEL (MODEL) 450DA, manufactured by BRANSON corporation), kohm ball MILLs ("Co-ballmill"), basket sand MILLs ("basketmill"), homomixers ("clemix") manufactured by homogenizer ("M Technique"), and "hookahs (jennius) PY" manufactured by wet jet MILLs ("Jenius"), nano MILLs ("nano MILLs," manufactured by nano MILLs), and extruders manufactured by sanohler, without limitation.
As the dispersant contained in the CNT dispersion liquid (F), a surfactant, a resin-type dispersant, or an organic pigment derivative can be used. Surfactants are mainly classified into anionic, cationic, nonionic and amphoteric. The dispersant is preferably a resin type dispersant. Specific examples of the dispersant are the same as those described for the resin composition (B), and therefore, description thereof is omitted here.
The solvent contained in the CNT dispersion liquid (F) is the same as the solvent described in the resin composition (B), and therefore, the description thereof is omitted here.
It is known that the resin composition (B) and the coating film (D) using the multilayered carbon nanotube (a) have good blackness.
The reason why the jet-blackness is good is considered to be: the multilayered carbon nanotube (a) having a small and uniform outer diameter has stronger interaction with the carbon nanotubes than the general carbon nanotubes, and firmly forms and holds a bundle. Therefore, the specific surface area is reduced, and the wettability to the solvent or dispersant is improved. In addition, the orientation of the carbon nanotubes is easily maintained in the resin composition (B) or the coating film (D) after dispersion, and the photoblocking effect is large.
Examples
The present invention will be described in more detail with reference to examples. The present invention is not limited to the following examples as long as the gist of the present invention is not exceeded. In the examples, "part" means "part by mass" and "%" means "% by mass" unless otherwise specified. In addition, "carbon nanotubes" may be abbreviated as "CNTs" and "carbon black" may be abbreviated as "CB".
< methods for measuring physical Properties >
The properties of CNTs or CNT coating films used in the examples and comparative examples described below were measured by the following methods.
< Raman spectroscopic analysis of CNT >
CNT was placed on a Raman microscope (manufactured by Epilora and horiba, ltd.) and measured with a laser wavelength of 532 nm. The measurement conditions were 60 seconds for acquisition time, 2 times for integration, 10% for a light-reducing filter, 20 times for magnification of an objective lens, 1200 lines per minute for a diffraction grating, 500 confocal apertures, and 100 μm in slit width. The CNTs for measurement were separated from the glass slide and flattened with a spatula. Among the peaks obtained, it will be 1560cm in the spectrum -1 ~1600cm -1 The maximum peak intensity is G, and is to be 1310cm -1 ~1350cm -1 D represents the maximum peak intensity in the range of (1), and the G/D ratio is the G/D ratio of CNT.
< powder X-ray diffraction analysis of CNT >
The analysis was performed by placing CNTs in an X-ray diffraction apparatus (eutima (Ultima) 2100, manufactured by science ltd) and operating from 1.5 ° to 80 °. The X-ray source is CuK α rays. The step size was 0.01 °, and the measurement time was 1.0 second. The curves showing the diffraction angles 2 θ =25 ° ± 2 ° obtained at this time were subjected to 11-point simple moving average, and the half width of the peak thereof was defined as the half width of CNT.
< preparation of CNT Dispersion >
In a 450mL SM sample bottle (manufactured by mitsui corporation), 0.2g of carbon nanotubes and 0.2g of polyvinylpyrrolidone (manufactured by tokyo chemical industries, ltd.) as a resin type dispersant were weighed, 200mL of isopropyl alcohol was added, and dispersion treatment was performed for 5 minutes in ice-cold with an amplitude of 50% using an ultrasonic homogenizer (advanced digital sonier (registered trademark), MODEL (MODEL) 450DA, and must be trusted (nson)), to prepare a CNT dispersion.
< Transmission Electron microscope analysis of CNT >
The CNT dispersion was diluted as appropriate, and a few. Mu.L of the dispersion was dropped on collodion film (COLLODIONMEMBRANE), dried at room temperature, and observed with a direct transmission electron microscope (H-7650, manufactured by Hitachi, ltd.). The observation was performed by taking photographs of 10 or more CNTs in a plurality of visual fields at a magnification of 5 ten thousand times, measuring the outer diameters of 300 CNTs arbitrarily extracted, and determining the average value thereof as the average outer diameter (nm) of the CNTs. The standard deviation was calculated by using the measured outer diameters of 300 CNTs as a parent cluster.
For reference, fig. 1 to 8 show graphs showing the relationship between the outer diameter and the number of the multi-walled carbon nanotubes in example 1, example 4, example 12 to example 13, and comparative example 1 to comparative example 4, which will be described later.
< method for measuring Brightness (L) of CNT coating film >
The CNT coating film was measured for brightness (L) from the surface coated with the CNT resin composition using a color difference meter (spectrocolorimeter SE6000, manufactured by NIPONDENSHOKU corporation).
< measurement of gloss of CNT coating film >
The CNT coating film was measured for 60 ° specular gloss from the surface coated with the CNT resin composition by a gloss meter GM-26D (manufactured by mura color research institute, inc.) based on JIS Z8741.
[ group of first embodiment ]
< example of production of CNT Synthesis catalyst >
The catalyst for CNT synthesis used in each of the examples and comparative examples described below was prepared by the following method.
CNT Synthesis catalyst (A)
CNT Synthesis catalyst (B)
60 parts of cobalt hydroxide, 138 parts of magnesium acetate tetrahydrate, and 8.1 parts of manganese carbonate were weighed out into a heat-resistant container, dried at 170 ± 5 ℃ for 1 hour using an electric oven to evaporate water, and then pulverized for 1 hour using a pulverizer (vance mill WC-3, manufactured by osaka chemical corporation) with a speed dial adjusted to 3. Then, each pulverized powder was mixed for 30 seconds by using a pulverizer (manufactured by wande mill WC-3, osaka chemical corporation) with a speed dial adjusted to 2, thereby producing a CNT synthesis catalyst precursor (B). The CNT synthesis catalyst precursor (B) was transferred to a heat-resistant container, calcined in a muffle furnace (FO 510, manufactured by yokoku corporation) under an air atmosphere at 450 ± 5 ℃ for 30 minutes, and then pulverized in a mortar to obtain the CNT synthesis catalyst (B).
CNT Synthesis catalyst (C)
CNT Synthesis catalyst (D)
CNT Synthesis catalyst (E)
CNT Synthesis catalyst (F)
Example 1 preparation of CNT (A)
A quartz glass heat-resistant vessel having an internal volume of 10L, which can be pressurized and heated by an external heater, was placed in the center of the horizontal reaction tube, and 2.0g of the CNT synthesis catalyst (A) was dispersed therein. The atmosphere in the horizontal reaction tube was adjusted to an oxygen concentration of 1 vol% or less by replacing the air in the reaction tube with nitrogen gas while injecting nitrogen gas and exhausting the gas. Then, the reaction mixture was heated by an external heater until the center temperature in the horizontal reaction tube became 680 ℃. After reaching 680 ℃, propane gas was introduced into the reaction tube as a carbon source at a flow rate of 2L/min, and a contact reaction was performed for 1 hour. After the reaction, the gas in the reaction tube was replaced with nitrogen, and the reaction tube was cooled to 100 ℃ or lower and taken out to obtain CNT (a).
Examples 2 to 5 preparation of CNTs (B) to (E)
CNTs (B) to (E) were obtained in the same manner as in example 1, except that the CNT synthesis catalysts (B) to (E) were used instead of the CNT synthesis catalyst (a).
Comparative example 1 production of CNT (F)
CNT (F) was obtained in the same manner as in example 1, except that the catalyst (F) for CNT synthesis was used instead of the catalyst (a) for CNT synthesis.
Comparative example 2 production of CNT (G)
A quartz glass heat-resistant vessel having an internal volume of 10L and capable of being pressurized and heated by an external heater was placed at the center of the horizontal reaction tube, and 2.0g of the CNT synthesis catalyst (F) was dispersed therein. The atmosphere in the horizontal reaction tube was adjusted to an oxygen concentration of 1 vol% or less by replacing the air in the reaction tube with nitrogen gas while injecting nitrogen gas and exhausting the gas. Then, the reaction mixture was heated by an external heater until the center temperature in the horizontal reaction tube became 680 ℃. After reaching 680 ℃, ethylene gas was introduced into the reaction tube as a carbon source at a flow rate of 2L/min, and a contact reaction was performed for 1 hour. After the reaction, the gas in the reaction tube was replaced with nitrogen, and the reaction tube was cooled to 100 ℃ or lower and taken out to obtain CNT (G).
Comparative examples 3 to 4 CNT (H) to (I)
The multilayered carbon nanotube (NC 7000, manufactured by nano-tillery) is referred to as CNT (H), and the multilayered carbon nanotube (parabi (Flotube) 9000, manufactured by sina (Cnano)) is referred to as CNT (I).
The evaluation results of CNTs (a) to (I) are shown in table 1. The mean outer diameter of the CNTs was expressed as X and the standard deviation of the outer diameter of the CNTs was expressed as σ.
[ Table 1]
TABLE 1
Example 6 preparation of CNT resin composition and coating film
CNT (A) was stirred at 1500rpm for 5 minutes using a high-speed stirrer (T.K. homodisperse (T.K. HOMODISISPER) MODEL (MODEL) 2.5, manufactured by PRIMIX, inc.) and 11.2g of a resin type dispersant (DISPERBYK (registered trademark) -111, manufactured by BYK-Chemie, inc., 100% of nonvolatile content), sorbso (SOLVESO) 150 (manufactured by Tokyo general Petroleum Co., ltd.) as a solvent, 48.8g of toluene, 73.5g of xylene, and 48.8g of butyl acetate, added to a plastic container (DESCEPT 1L, manufactured by Tokyo Nitri instruments, inc.) as a dispersant, and stirred at 1500 rpm. Then, a dispersion treatment was performed for 5 minutes at 5000rpm using a high-speed stirrer (t.k. homomixer mark II (t.k. hommizermarkii) MODEL (MODEL) 2.5, manufactured by Primicks (PRIMIX) corporation) to obtain a CNT crude dispersion (a). 100 parts of the CNT crude dispersion (A) and 175 parts of zirconia beads (bead diameter: 1.0 mm. Phi.) were charged in a 200mL SM sample bottle (manufactured by Sanmerck Co., ltd.) and subjected to a dispersion treatment for 3 hours using a paint conditioner manufactured by RedDevil, inc. to obtain a CNT dispersion (A). Then, 92.6 parts of an acrylic resin (manufactured by DIC corporation, aridi (acrylic) 47-712, 50% of nonvolatile content) was added thereto, and the mixture was stirred at 1500rpm for 5 minutes by using a high-speed stirrer (t.k. Homo disper) MODEL (MODEL) 2.5, manufactured by primimix (primimix) corporation). Then, 19.3 parts of melamine resin (SUPER beckmine) L-117-60, 60% of nonvolatile matter) was added to the CNT dispersion liquid (a), and the mixture was dispersed for 30 minutes using a paint conditioner manufactured by Red Devil, to obtain a CNT resin composition (a). Then, a CNT resin composition (a) was spray-coated on one surface of a Polyethylene Terephthalate (PET) film (lumiror 100, T60, manufactured by toray) so that the film thickness after drying became 20 μm. Spray coating was carried out using an air gun (W-61-2G manufactured by Anitet (anest) Seika). The coated PET film was left at room temperature for 30 minutes and then dried at 140 ± 5 ℃ for 30 minutes to prepare a CNT coating film (a).
(examples 7 to 10), (comparative examples 5 to 8)
CNT resin compositions (B) to (I), CNT dispersions (B) to (I), and CNT coating films (B) to (I) were obtained in the same manner as in example 6, except that the CNTs described in table 2 were changed.
[ Table 2]
TABLE 2
Table 3 shows the evaluation results of the CNT coating films produced in examples 6 to 10 and comparative examples 5 to 8. The evaluation criteria for the blackening resistance are as follows. The brightness (L) of the coating film is 5.5 or less and the 60 ° specular gloss is 80 or more (excellent), the brightness (L) of the coating film is 5.7 or less and the 60 ° specular gloss is 80 or more (excellent), and the brightness (L) of the coating film is more than 5.7 or the 60 ° specular gloss is less than 80 (poor).
[ Table 3]
TABLE 3
Comparative example 9
A CB resin composition (a), a CB dispersion liquid (a), and a CB coating film (a) were obtained in the same manner as in example 6, except that carbon black (COLORBlack) FW-200 manufactured by Degussa corporation was used instead of CNT.
Table 4 shows the evaluation results of the CB coating film produced in comparative example 9. The evaluation criteria for the jet-blackness are as follows. The brightness (L) of the coating film is 5.5 or less and the 60 ° specular gloss is 80 or more (excellent), the brightness (L) of the coating film is 5.7 or less and the 60 ° specular gloss is 80 or more (excellent), and the brightness (L) of the coating film is more than 5.7 or the 60 ° specular gloss is less than 80 (poor).
[ Table 4]
TABLE 4
From the results of the first group of examples, it was found that the coating films of examples 6 to 10 using the multi-walled carbon nanotubes of examples 1 to 5 having an average outer diameter of 10nm or less and a standard deviation of the outer diameter of 4nm or less have particularly low brightness and excellent jet-black property, compared with the coating films of comparative examples 5 to 8 using the multi-walled carbon nanotubes having a large outer diameter or the coating films of comparative example 9 using carbon nano black.
[ group of second embodiment ]
< example of production of CNT Synthesis catalyst >
The catalyst carrier for CNT synthesis, the cobalt composition, and the catalyst for CNT synthesis used in the examples and comparative examples described below were prepared by the following methods.
< preparation of catalyst support for CNT Synthesis >
1000 parts of magnesium acetate tetrahydrate was weighed into a heat-resistant container, dried at an atmospheric temperature of 170. + -. 5 ℃ for 6 hours using an electric oven, and then pulverized using a pulverizer (a sample grinder KIIW-I, manufactured by Dalton, inc.) with a 1mm wire net installed, to obtain a dried pulverized product of magnesium acetate. Magnesium acetate dry-crushed product 45.8 parts, manganese carbonate 8.1 parts, silicon oxide (SiO) 2 Manufactured by the company erlotin (AEROSIL): arocil (AEROSIL) (registered trademark) 200) 1.0 part and a steel ball (bead diameter: 2.0 mm. Phi.) 200 parts were charged in an SM sample bottle (manufactured by Sanmerck Co., ltd.), and subjected to pulverization and mixing treatment for 30 minutes using a paint conditioner manufactured by RedDevil. Then, the pulverized and mixed powder was separated from steel balls (bead diameter 2.0 mm. Phi.) by using a stainless steel sieve, to obtain a catalyst carrier for CNT synthesis.
< preparation of catalyst for CNT Synthesis >
30 parts of cobalt (II) hydroxide are weighed into a heat-resistant container at 17Drying at 0 + -5 deg.C for 2 hr to obtain a product containing CoHO 2 The cobalt composition of (1). Then, 54.9 parts of the catalyst carrier for CNT synthesis and 29 parts of the cobalt composition were charged into a pulverizer (vance mill WC-3, manufactured by osaka chemical corporation), a standard lid was attached, the dial of the speed was adjusted to 2, and the catalyst carrier for CNT synthesis was pulverized and mixed for 30 seconds to obtain a catalyst precursor for CNT synthesis. The CNT synthesis catalyst precursor was transferred to a heat-resistant container, calcined in a muffle furnace (FO 510, manufactured by yokoku corporation) under an air atmosphere at 450 ± 5 ℃ for 30 minutes, and then pulverized in a mortar to obtain a CNT synthesis catalyst.
Example 11 production of CNT (K)
A quartz glass heat-resistant vessel in which 1g of the CNT synthesis catalyst was dispersed was placed in the center of a 10L horizontal reaction tube which was capable of being pressurized and heated by an external heater. While nitrogen gas was injected, the reaction tube was evacuated, and the atmosphere in the reaction tube was replaced with nitrogen gas, and the reaction tube was heated until the atmospheric temperature in the horizontal reaction tube became 710 ℃. After reaching 710 ℃, ethylene gas was introduced into the reaction tube as a hydrocarbon at a flow rate of 2L/min, and a contact reaction was carried out for 7 minutes. After the reaction, the gas in the reaction tube was replaced with nitrogen, and the reaction tube was cooled to 100 ℃ or lower and taken out, thereby obtaining CNT (K).
(example 12 to example 16)
CNTs (L) to (P) were obtained in the same manner as in example 11, except that the amount of catalyst, temperature, and reaction time were changed as shown in table 5.
[ Table 5]
TABLE 5
(example 17 to example 19)
CNTs (Q) to (S) were obtained in the same manner as in example 11, except that the temperature and reaction time described in table 6 were changed.
[ Table 6]
TABLE 6
(examples 20 to 21)
CNTs (T) and (U) were obtained in the same manner as in example 11, except that the amount of catalyst, temperature, reaction time, and hydrocarbon were changed as shown in table 7.
[ Table 7]
TABLE 7
Table 8 shows the evaluation results of CNTs produced in examples 11 to 21.
[ Table 8]
TABLE 8
Example 22 preparation of CNT resin composition and coating film
CNT (K) 5.6g, a resin type dispersant (DISPERBYK (registered trade name) -111, BYK chemical (BYK-Chemie) Co., ltd., nonvolatile content 100%) 11.2g as a dispersant, sorbesso (SOLVESO) 150 (Tokyo general Petroleum Co., ltd.) as a solvent 48.8g, toluene 73.5g, xylene 73.5g, and butyl acetate 48.8g were added to a plastic container (Deska 1L, tokyo Nippon instruments Co., ltd.), and the mixture was stirred at a rotation speed of 1500rpm for 5 minutes by using a high speed stirrer (T.K. homogenizing Dispersion machine (T.K. HOMODISPER) MODEL (MODEL) 2.5, and Primox (PRIMIX). Then, a dispersion treatment was performed for 5 minutes at 5000rpm using a high-speed stirrer (t.k. homomixer mark II (t.k. hommizermarkii) MODEL (MODEL) 2.5, manufactured by Primicks (PRIMIX) corporation) to obtain a CNT crude dispersion (K). 100 parts of the CNT crude dispersion (K) and 175 parts of zirconia beads (bead diameter: 1.0 mm. Phi.) were filled in a 200mL SM sample bottle (manufactured by Sanmerck Co., ltd.) and dispersion treatment was performed for 3 hours using a paint conditioner manufactured by RedDevil (R.RTM.) to obtain a CNT dispersion A. Then, 92.6 parts of an acrylic resin (manufactured by DIC corporation, ayndi (ACRYDIC) 47 to 712, 50% of nonvolatile content) was added thereto, and the mixture was stirred at 1500rpm for 5 minutes using a high-speed stirrer (t.k. Homo disperser (t.k. Homo saper) MODEL (mode) 2.5, manufactured by Prim (PRIMIX) gmbh). Then, 19.3 parts of melamine resin (SUPER beckmine) L-117-60, 60% of nonvolatile matter) was added to the CNT dispersion (K), and the mixture was dispersed for 30 minutes using a paint conditioner manufactured by Red Devil, to obtain a CNT resin composition (K). Then, the CNT resin composition (K) was spray-coated on one surface of a PET (polyethylene terephthalate) film (lumiror 100, T60, manufactured by dongli corporation) as a substrate so that the film thickness after drying became 20 μm. Spray coating was carried out using an air gun (W-61-2G manufactured by Anitet (anest) Seika). The coated PET film was left at room temperature for 30 minutes, and then dried at 140 ± 5 ℃ for 30 minutes to prepare a CNT coating film (K).
(example 23 to example 32)
CNT resin compositions (L) to (U), CNT dispersions (L) to (U), and CNT coating films (L) to (U) were obtained in the same manner as in example 22, except that the CNTs described in table 9 were changed.
[ Table 9]
TABLE 9
Table 10 shows the evaluation results of the CNT coating films produced in examples 22 to 32. In the assessment of the jet-black property, the brightness (L) of the coating film was 5.2 or less and the 60 ° specular gloss was 80 or more (excellent), the brightness (L) of the coating film was 5.3 or less and the 60 ° specular gloss was 80 or more (excellent), the brightness (L) of the coating film was 5.5 or less and the 60 ° specular gloss was 80 or more (good), the brightness (L) of the coating film was 5.7 or less and the 60 ° specular gloss was 80 or more (acceptable), and the brightness (L) of the coating film was more than 5.7 or the 60 ° specular gloss was less than 80 (poor).
[ Table 10]
CNT coating film | Brightness of light | 60 degree mirror surface gloss | Evaluation of blackening Property | |
Example 22 | K | 5.15 | 101 | ++++ |
Example 23 | L | 5.12 | 96 | ++++ |
Example 24 | M | 5.15 | 102 | ++++ |
Example 25 | N | 5.19 | 99 | ++++ |
Example 26 | O | 5.25 | 101 | +++ |
Example 27 | P | 5.28 | 101 | +++ |
Example 28 | Q | 5.35 | 101 | ++ |
Example 29 | R | 5.37 | 103 | ++ |
Example 30 | S | 5.35 | 99 | ++ |
Example 31 | T | 5.31 | 95 | ++ |
Example 32 | U | 5.33 | 96 | ++ |
From the results of the second example group, it is clear that the coating films of examples 22 to 27 using the multi-walled carbon nanotubes of examples 11 to 16 have excellent jet-black property, and the multi-walled carbon nanotubes of examples 11 to 16 have an average outer diameter of 10nm or less, a standard deviation of the outer diameter of 4nm or less, and a half-value width of a peak at a diffraction angle 2 θ =25 ° ± 2 ° in powder X-ray diffraction analysis of 5 ° to 5.5 °.
The present invention has been described above with reference to the embodiments, but the present invention is not limited thereto. The present invention may be modified in various ways within the scope of the invention, as will be understood by those skilled in the art.
Claims (9)
1. A multilayered carbon nanotube satisfying the following conditions 1 and 2:
condition 1: the average outer diameter of the multilayered carbon nanotube is 10nm or less
Condition 2: the standard deviation of the outer diameter of the multi-layered carbon nanotube is 4nm or less,
wherein, in powder X-ray diffraction analysis, a peak exists at a diffraction angle 2 theta =25 DEG + -2 DEG, and a half-value width of the peak is 3 DEG or more and 5.5 DEG or less.
2. The carbon nanotube according to claim 1, wherein X ± 2 σ satisfies 2.5nm ≦ X ± 2 σ ≦ 15.5nm, where X is an average outer diameter of the carbon nanotube and σ is a standard deviation of the outer diameter of the carbon nanotube.
3. The carbon nanotube of claim 1, wherein the Raman spectrum is 1560cm -1 ~1600cm -1 The maximum peak intensity in the range of (1) is G, and 1310cm -1 ~1350cm -1 The ratio G/D is 2.0 or less, where D is the maximum peak intensity in the range of (1).
4. The carbon nanotube of claim 1, wherein the Raman spectrum is 1560cm -1 ~1600cm -1 G, 1310cm, or -1 ~1350cm -1 The ratio G/D is 1.0 or less, where D is the maximum peak intensity in the range of (1).
5. A method for producing the multilayered carbon nanotube according to any one of claims 1 to 4, comprising the steps of:
step 1: mixing and/or pulverizing an active component containing one or more selected from cobalt, nickel and iron with a catalyst support containing one or more selected from magnesium, aluminum and silicon, and calcining the mixture to obtain a catalyst
Step 2: a step of contacting the catalyst with a carbon source containing one or more selected from the group consisting of hydrocarbons and alcohols under heating to obtain a multilayered carbon nanotube,
wherein in the step 2, the carbon source contains a hydrocarbon, and the amount of the catalyst and/or the flow rate of the hydrocarbon are adjusted so that Y/Z satisfies 1.5 ≦ Y/Z ≦ 2.7, where Y is a production amount of the multilayered carbon nanotube per 1g of the catalyst and g is a unit, Z is a contact reaction time of the catalyst and the hydrocarbon, and min is a unit.
6. The method for producing multilayered carbon nanotubes according to claim 5, wherein the hydrocarbon is ethylene.
7. A dispersion comprising: the multilayered carbon nanotube of any one of claims 1 to 3, and a dispersant.
8. A resin composition comprising: the multilayered carbon nanotube according to any one of claims 1 to 3, and a resin.
9. A coating film formed from the resin composition according to claim 8.
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