WO2012091083A1 - Pigment azoïque noir et procédé de production de celui-ci, composition colorée, procédé de coloration et articles colorés - Google Patents

Pigment azoïque noir et procédé de production de celui-ci, composition colorée, procédé de coloration et articles colorés Download PDF

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Publication number
WO2012091083A1
WO2012091083A1 PCT/JP2011/080370 JP2011080370W WO2012091083A1 WO 2012091083 A1 WO2012091083 A1 WO 2012091083A1 JP 2011080370 W JP2011080370 W JP 2011080370W WO 2012091083 A1 WO2012091083 A1 WO 2012091083A1
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Prior art keywords
pigment
black
hydroxy
azo
hbc
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PCT/JP2011/080370
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English (en)
Japanese (ja)
Inventor
中村　道衛
士郎 山宮
坂本　茂
岡本　久男
悟 松崎
伊藤　秀樹
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大日精化工業株式会社
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Application filed by 大日精化工業株式会社 filed Critical 大日精化工業株式会社
Priority to JP2012551035A priority Critical patent/JP5866299B2/ja
Priority to CN201180063596.4A priority patent/CN103282443B/zh
Priority to KR1020137019523A priority patent/KR101638669B1/ko
Publication of WO2012091083A1 publication Critical patent/WO2012091083A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
    • C09B35/02—Disazo dyes
    • C09B35/021—Disazo dyes characterised by two coupling components of the same type
    • C09B35/033—Disazo dyes characterised by two coupling components of the same type in which the coupling component is an arylamide of an o-hydroxy-carboxylic acid or of a beta-keto-carboxylic acid
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
    • C09B35/02—Disazo dyes
    • C09B35/021—Disazo dyes characterised by two coupling components of the same type
    • C09B35/03—Disazo dyes characterised by two coupling components of the same type in which the coupling component is a heterocyclic compound
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
    • C09B35/02—Disazo dyes
    • C09B35/037—Disazo dyes characterised by two coupling components of different types
    • C—CHEMISTRY; METALLURGY
    • 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
    • C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
    • C09D7/40—Additives
    • C09D7/41—Organic pigments; Organic dyes

Definitions

  • the present invention relates to a black azo dye, a production method thereof, a coloring composition, a coloring method, and colored articles. More specifically, it has a specific structure that exhibits optical characteristics useful for applications that use absorption in the visible light region, and that is transparent in the infrared region and that uses infrared rays.
  • the present invention relates to a black polyazo dye, and further relates to a production method, a colored composition, a coloring method using the same, and colored articles.
  • Carbon black pigments and iron oxide black pigments are common as black pigments used in colorants for paints, printing inks and plastics. These black pigments exhibit black color by absorbing light in all wavelength regions of light.
  • Sunlight is an electromagnetic wave, and light in the region of about 380 nm to 780 nm is regarded as visible light, and light in the region of 0.7 ⁇ m to 2.5 ⁇ m having a longer wavelength than the visible light is near infrared. Black can be shown by absorbing light in the visible light wavelength range, but as a result, the carbon black pigment absorbs not only visible light but also light in the near infrared region.
  • an infrared remote control transmitter and its main receiver can be used for electric appliances, lighting fixtures, warm toilet seats, cameras, automobile door locks, engine starters, opening / closing garages, infrared security cameras and infrared surveillance around streets and buildings. Widely used in daily life, such as cameras.
  • transmits infrared rays are equipped.
  • a night vision device for vehicles is proposed.
  • As a pigment used in these infrared transmitters, infrared filters of receivers, infrared filters of infrared cameras, etc. it shows optical properties that transmit light in the infrared region and completely block light in the visible region, There is a demand for a dye having a function with excellent durability such as heat resistance, light resistance, and solvent resistance.
  • a photovoltaic power generation module constituting a photovoltaic power generation system is attached to a place that is directly irradiated with sunlight, particularly an outdoor open space, a rooftop of an outdoor building, a roof, and the like.
  • irradiation with sunlight and absorption of light brings about a rise in temperature of the photovoltaic power generation module and a reduction in the output of the power generation cell.
  • it is sometimes colored black, dark chromatic, or dark chromatic from the aesthetic point of view. In some cases, this causes a significant temperature increase. ing. Therefore, even if it is colored black in a solar power generation system, a coloring system that suppresses temperature rise as much as possible is expected.
  • a solar cell backsheet comprising a perylene pigment has been proposed (Patent Document 2).
  • thermal barrier coating by reflection of sunlight has been demanded from the viewpoint of improvement of living environment, comfort, and energy saving
  • development of heat ray reflective materials for this purpose has been demanded in various applications.
  • roofs and walls of houses and buildings such as houses, offices, warehouses, buildings, road paving, automobile exteriors and interiors, ships, etc. Materials and the like are demanded, and heat dissipation materials such as electronic parts are also demanded.
  • LCD liquid crystal displays
  • Information display devices such as information devices, monitors, car navigation systems, mobile phones, display screens for electronic computers and electronic dictionaries, information bulletin boards, information bulletin boards, function display boards, signboard displays, digital camera and video camera shooting screens, etc. It is used widely.
  • improvement of display quality and cost reduction of display are demanded, and quality of color filters (hereinafter sometimes abbreviated as “CF”) are improved and costs are reduced.
  • CFs mounted on LCDs are also required to have superior quality in terms of color characteristics and optical characteristics of image performance such as definition, color density, light transmission, and contrast.
  • R (red), G (green), and B (blue) pixels are arranged in stripes, mosaics, triangles, etc., and illuminated from the back with a backlight. Colors are generated by additive color mixing of transmitted light to produce an image.
  • a black matrix (hereinafter sometimes abbreviated as “BM”) is formed around each pixel in a lattice shape to shield unnecessary light and prevent color mixing.
  • BM black matrix
  • red pigments, green pigments, blue pigments, yellow pigments, purple pigments, and the like are used, but each has been improved.
  • BM uses a black pigment from a metallic chromium film as a light-shielding material for completely shielding the visible light region of the backlight due to problems such as an increase in substrate size and the environmental impact of chromium compounds. It has shifted to resin BM.
  • the backlight has been replaced with a light emitting diode (LED) instead of a cold cathode fluorescent tube, leading to an improvement in color purity and an expansion of the color reproduction range.
  • the light emitted from the red region was sharp light of about 600 to 620 nm in the backlight of the cold cathode fluorescent tube, but in the LED backlight, the maximum emission wavelength is around 640 nm as the light from the red light emitting part. It has been proposed to use broad light having a range of approximately 540 nm to 800 nm (Patent Document 3). Therefore, it is a necessary condition for the BM to be able to sufficiently shield light on the long wavelength side of visible light.
  • IPS, BOA, and COA methods described above are methods for forming a BM on an active element such as a TFT.
  • the BM is not electrically insulating, the TFT malfunctions. There is a fear.
  • Carbon black pigments generally used as light-shielding black pigments are inherently low in electrical resistance, are not suitable as light-shielding black pigments used in these systems, and are light-shielding materials with high electrical insulation. It is desirable.
  • Patent Document 6 a proposal for a carbon black pigment in which a carbon black pigment defined by an oxygen amount is coated with a highly insulating resin film to improve electrical insulation
  • Insulating BM is formed using an insulating carbon black pigment or a carbon black pigment that has been coated with a resin and improved in electrical insulation, and applied to a COA system (Patent Document 7).
  • carbon black pigments are inherently conductive materials, and it is difficult to achieve complete insulation even with resin coating as in the prior art described above.
  • the use of BM is proposed to prevent color mixing of adjacent light from the light emitting element and to improve the sharpness of the light emitting screen. (Patent Document 8).
  • the object of the present invention is not only to exhibit excellent physical properties and fastness as a pigment, but also to optical properties of both visible light shielding properties and infrared transmittance properties applicable to various applications as described above.
  • the present invention provides a black pigment, a method for producing the pigment, a coloring composition containing the pigment, a coloring method using the pigment, and colored articles.
  • black polyazo pigments having a specific structure have a visible light wavelength range. Absorbs light with a wavelength of approximately 400 to 750 nm in almost the entire optical region at a high level, and further exhibits high transmittance on the long wavelength side of the infrared region of approximately 900 to 1500 nm, and further has an average particle diameter of 10 nm. It has been found that a black pigment that has been refined and pigmented to have a thickness of ⁇ 200 nm is suitable for the various uses mentioned above, and has solved the above-mentioned problems and completed the present invention.
  • the present invention is a black azo pigment exhibiting both optical properties of both visible light shielding properties and infrared ray transparency, and at least one 2 introduced from a coupling component and two or more azo bonds in the molecule.
  • a black polyazo pigment having a structure having a hydroxy-11H-benzo [a] -carbazole-3-carboxylic acid amide residue and having an average particle diameter of 10 nm to 200 nm
  • An azo pigment is provided.
  • the visible light shielding property is that a black colored film containing a black azo pigment on a transparent substrate exhibits a spectral transmittance of about 5% or less in a wavelength range of about 400 to 750 nm in the visible light range.
  • the external transmittance is a black azo pigment in which the black colored film exhibits a transmittance of about 30% or more in the wavelength range of 900 to 1500 nm in the infrared region.
  • a diazonium salt obtained by diazotizing a compound having two or more amino groups (representative formula: H 2 N—Ar—NH 2 ) is used as a diazo component, and 2-hydroxy as a coupling component is used as the coupling component.
  • HBC-HBC 2-hydroxy-11H-benzo [a] -carbazole-3-carboxamide residues
  • HBC- 2-hydroxy-11H-benzo [a] -carbazole-3-carboxamide residue
  • Cp- other coupling component residues
  • “Ar” typically represents a residue of an aromatic compound or a heterocyclic compound, and when there are two or more in the formula, they may be the same or different.
  • “Ar—N ⁇ N—” and “—N ⁇ N—Ar—N ⁇ N—” in the formula mean an “arylazo residue” coupled with a diazonium salt of a diazo component. The same applies to the following.
  • the present invention is a production method for obtaining the above-described black azo pigment of the present invention, comprising a step of synthesizing a black polyazo pigment and a step of refining the pigment as necessary.
  • a method for producing (I) a method for synthesizing a black polyazo pigment is any one of the following four types, and the polyazo pigment synthesized by these methods is coarse, which will be described later.
  • a method for producing a black azo pigment which comprises a step of refining the average particle size of the pigment to 10 nm to 200 nm by any known method.
  • the present invention includes a pigment component containing the black azo pigment of the present invention described above or the black azo pigment obtained by the above production method in a liquid dispersion medium or a solid dispersion medium.
  • a coloring composition is provided.
  • a coloring method for an article wherein the coloring composition is used when the article is colored black or dark by coloring the surface of the article or coloring the article itself. I will provide a.
  • the present invention provides, as another embodiment, a colored article characterized by being subjected to the above-described method for coloring an article.
  • the present invention is a back sheet of a photovoltaic module in which a black or dark infrared transmissive layer is laminated on a light reflective sheet, and the infrared transmissive layer includes:
  • the molecule has two or more azo bonds and at least one 2-hydroxy-11H-benzo [a] -carbazole-3-carboxylic acid amide residue (abbreviated as HBC-) introduced from a coupling component.
  • HBC- 2-hydroxy-11H-benzo [a] -carbazole-3-carboxylic acid amide residue
  • the present invention uses a light-reflective sheet that is light-reflective on the substrate itself, or a substrate provided with a pre-formed light-reflective substrate as a light-reflective sheet. And at least one 2-hydroxy-11H-benzo [a]-introduced from the coupling component and two or more azo bonds in the molecule on the surface of the substrate or the light-reflective substrate.
  • HBC- carbazole-3-carboxylic acid amide residue
  • Others provide a back sheet manufacturing method of the photovoltaic module, characterized in that the multilayer infrared permeable layer of dark color.
  • a black matrix (BM) formed on a color filter (CF) substrate or an organic EL light-emitting substrate is introduced from two or more azo bonds and a coupling component in the molecule.
  • Black polyazo pigment having a structure having at least one 2-hydroxy-11H-benzo [a] -carbazole-3-carboxylic acid amide residue (abbreviated as HBC-) and an average particle diameter of 10 nm to 200 nm
  • HBC- 2-hydroxy-11H-benzo [a] -carbazole-3-carboxylic acid amide residue
  • the present invention provides a color display panel characterized by containing.
  • the black colored film containing the black azo pigment shows almost complete absorption in the wavelength range of about 400 to 750 nm covering the visible light range on the transparent substrate.
  • the black azo pigment of the present invention is effectively used as an infrared filter for an infrared remote controller and a main body receiver.
  • the black azo pigment of the present invention can be used as an infrared filter of an infrared sensing device that detects and identifies roadside obstacles such as automobiles that are being put into practical use.
  • the black azo pigment of the present invention covers the visible light region and exhibits optical characteristics that absorb almost completely even on the long wavelength side, as a light-shielding black material for CF BM, for example, it supports red pixels.
  • the wavelength range of the light from the red light emitting part of the LED backlight is sufficiently absorbed and can be blocked, and the color of the LCD is not only black but also other chromatic colors are vividly developed.
  • various CF improvement methods for forming a BM on an active element such as a TFT for example, a BM that maintains the thickness of a liquid crystal layer in place of a spacer, a CF for an IPS method, a COA method, etc.
  • a light-shielding black pigment for forming the BM It is also suitable as a light-shielding black pigment for forming the BM.
  • a light-shielding black pigment for an IPS liquid crystal panel or the like employing an LED backlight and also in an organic EL display.
  • the black azo pigment which characterizes the present invention, absorbs the entire visible light region as an optical property, exhibits almost complete absorption even in the wavelength range on the long wavelength side, and has a high transmittance in the near infrared region. Indicates. Specifically, the spectral transmittance of the black colored thin film on the transparent substrate is about 5% or less in the wavelength range of 400 to 750 nm in the visible light range, and in the infrared wavelength range of about 900 nm to 1500 nm. About 30% or more. Moreover, as an electrical property, very high electrical insulation is shown.
  • the present inventors have found that particularly easy synthesis. Therefore, a black polyazo pigment having a specific chemical structure having two or more azo bonds in the molecule was developed. Furthermore, since high transmittance in the infrared region is particularly required, the black polyazo pigment is preferably a pigment having a fine particle size, and the average particle size of the pigment needs to be about 10 nm to 200 nm. .
  • an ultrafine black polyazo pigment having an average particle diameter of about 10 nm to 50 nm, or a black azo pigment having a disperse dye-like property that causes molecular dispersion in a medium in a coloring process.
  • the polyazo pigment means a disazo pigment or a trisazo pigment having two or more azo bonds in the molecule as described above.
  • the present inventors have reported that at least one 2-hydroxy-11H-benzo [a] having two or more azo bonds in the molecule and introduced from the coupling component thereof.
  • a chemical structure having a carbazole-3-carboxamide residue was found.
  • an azo cup using a diazo component having two or more amino groups that change to a diazonium group as a diazo component is used.
  • Examples thereof include a ring method and a azo coupling method using a coupling component having a coupling component having two or more coupling positions. This point will be described in detail.
  • the black polyazo pigment of the present invention preferably has any of the following structures (1) to (4).
  • black polyazo pigments having the structure (1) represented by the above [HBC-N ⁇ N—Ar—N ⁇ N—HBC] include benzidine or phenylenediamine having two or more amino groups in the diazo component as follows. An example of the structure when used is given.
  • HBC-N A black polyazo pigment having a structure represented by N—Ar—N ⁇ N—Cp].
  • black polyazo pigment having the structure (2) represented by the above [HBC-N ⁇ N—Ar—N ⁇ N—Cp] examples include benzidine or phenylenediamine having two or more amino groups in the diazo component as follows.
  • An example of the structure when 2-hydroxy-3-naphthoic acid arylamide is used as another coupling component will be given.
  • HBC-HBC 2-hydroxy-11H-benzo [a] -carbazole-3-carboxamide residues
  • HBC- 2-hydroxy-11H-benzo [a] -carbazole-3-carboxamide residues
  • Examples of the black polyazo pigment having the structure (3) represented by the above [Ar—N ⁇ N—HBC—HBC—N ⁇ N—Ar] are as follows: 2-hydroxy-11H-benzoate via phenylene or biphenylene Example of structure obtained by diazotization using aniline having one amino group as diazo component in HBC-HBC as a coupling component in which two [a] -carbazole-3-carboxamide residues are bonded Give up.
  • black polyazo pigment having the structure (4) represented by [Ar—N ⁇ N—HBC—Cp—N ⁇ N—Ar], 2-hydroxy-11H-benzo [ a] -carbazole-3-carboxamide residue and HBC-Cp of the coupling component to which the residue of 2-hydroxy-3-naphthoic acid arylamide, which is another coupling component other than the compound, is bonded
  • Examples of structures obtained by diazotization using aniline having one amino group as the diazo component will be given.
  • the black azo pigment of the present invention is a black color of the present invention having a synthesis step of a polyazo pigment having the structure as described above, and a step of adjusting the particle size of pigment particles for refining the pigment as necessary. It can be easily obtained by a method for producing an azo pigment. Hereinafter, the manufacturing method of the black azo pigment of this invention is demonstrated.
  • the method for synthesizing the black polyazo pigment constituting the method for producing the black azo pigment of the present invention is selected from the following methods (1) to (4).
  • a diazonium salt formed by diazotizing a compound having two or more amino groups (representative formula: H 2 N—Ar—NH 2 ) is converted into 2-hydroxy-11H-benzo [a] -carbazole-
  • 3-carboxylic acid arylamide (abbreviated as HBC) is azo-coupled.
  • a diazonium salt obtained by diazotizing a compound having two or more amino groups (representative formula: H 2 N—Ar—NH 2 ) is converted to 2-hydroxy-11H-benzo [a] -carbazole-
  • a diazonium salt obtained by diazotizing a compound (representative formula: H 2 N—Ar—NH 2 ) is azo-coupled with an equimolar or less coupling component (Cp), and if necessary, two or more The coupling component (Cp) of the polyazo pigment was separated and removed, and then the coupling component (HB) was added to the uncoupled diazonium group.
  • the method (3) is the following method (3-1) or (3-2).
  • the black polyazo pigments obtained by the synthesis methods (3-1) and (3-2) have the structure represented by [Ar—N ⁇ N—HBC—HBC—N ⁇ N—Ar] described above. It will have.
  • a coupling component (denoted as HBC-HBC) having two or more 2-hydroxy-11H-benzo [a] -carbazole-3-carboxamide residues (abbreviated as HBC-) in the molecule
  • HBC- 2-hydroxy-11H-benzo [a] -carbazole-3-carboxamide residues
  • a diazonium salt obtained by diazotizing a 2-hydroxy-11H-benzo [a] -carbazole-3-carboxylic acid with a compound having one amino group (indicated as Ar—NH 2 ) is an azo cup.
  • the carboxylic acid of the azo dye is condensed with an aryl polyamine to form a polycarboxamide.
  • the method (4) is the following method (4-1) or (4-2).
  • the black polyazo pigments obtained by the synthesis methods (4-1) and (4-2) have the structure represented by [Ar—N ⁇ N—HBC—Cp—N ⁇ N—Ar] described above. It will have.
  • HBC-Cp 2-hydroxy-11H-benzo [a] -carbazole-3-carboxamide residue in one molecule and other coupling component residues (Cp- And a diazonium salt obtained by diazotizing a compound having one amino group (indicated as Ar—NH 2 ) to a coupling component (indicated as HBC-Cp).
  • the diazo component and the coupling component that can be used in each of the synthesis methods listed above will be described.
  • the coupling component is specifically exemplified.
  • Examples of the coupling component (HBC) include 2-hydroxy-11H-benzo [a] -carbazole-3-anilide, 2-hydroxy-11H-benzo [a] -carbazole-3-naphthylamide, and the like. Their derivatives.
  • substituent of the derivative examples include an alkyl (carbon number: 1 to 10) group, an alkoxy (carbon number: 1 to 10) group, a trifluoromethyl group, a halogen group, an alkyloxycarbonyl group, a cyclic iminodioxy group, and an alkylsulfonyl.
  • a coupling component in which one or more groups, aminocarbonyl group, benzamide group, alkylaminocarbonyl group, anilinocarbonyl group, cyclic ureylene group, carboxyl group, alkylimino group and the like are introduced.
  • Examples of the coupling component (HBC-HBC) include phenylene-bis (2-hydroxy-11H-benzo [a] -carbazole-3-carboxamide), biphenylene-bis (2-hydroxy-11H-benzo [ a] -carbazole-3-carboxamide), naphthalene-bis (2-hydroxy-11H-benzo [a] -carbazole-3-carboxamide) and the like and their derivatives.
  • a substituent of the derivative a known substituent such as an alkyl (carbon number: 1 to 10) group, an alkoxy (carbon number: 1 to 10) group, a trifluoromethyl group, a halogen group, etc.
  • Examples of the coupling component (Cp) include 2-hydroxy-3-naphthoic acid arylamide, 2-hydroxy-6-naphthoic acid arylamide, 2-hydroxy-3-anthracenecarboxylic acid arylamide, 2 -Hydroxy-3-dibenzofurancarboxylic acid arylamide, 2-hydroxy-1-carbazolecarboxylic acid arylamide and the like and their derivatives.
  • the diazo component is specifically exemplified.
  • Examples of the compound having two or more amino groups of the diazo component include, for example, phenylenediamine, diaminobiphenyl, diaminonaphthalene, diaminoanthraquinone, diamino-benzophenone, diamino Pyridine and the like and derivatives thereof.
  • a substituent of the derivative a known substituent such as an alkyl (carbon number: 1 to 10) group, an alkoxy (carbon number: 1 to 10) group, a trifluoromethyl group, a halogen group, etc.
  • Examples of the compound having one amino group of the diazo component include aniline, naphthylamine, aminoanthraquinone, phenoxyaniline, phenyliminoaniline, and derivatives thereof.
  • a substituent of the derivative a known substituent for the aryl group, for example, an alkyl (carbon number: 1 to 10) group, an alkoxy (carbon number; 1 to 10) group, a halogen group, a nitro group, a phenyl ether group, A diazo component having one or more phenylimino group, benzoylamide group, anilinocarbonyl group, cyclic ureylene group, etc. introduced therein.
  • C.I. I. Azoic diazo components 5, 8, 9, 10, 32, 33, 34, 35, 36, 37, 41, 42, 43, 47 and the like.
  • the black azo pigment of the present invention is obtained by the following method (1) or (2) when the particle size of the polyazo pigment obtained by the synthesis method as described above is coarse. It can be obtained by reducing the average particle diameter of the pigment to about 10 nm to 200 nm. That is, in order to improve the infrared transmittance of the coating film using the polyazo pigment obtained by the synthesis method listed above, the particle diameter of the dispersed pigment is smaller than the wavelength of light, Specifically, the average particle size needs to be about 10 nm to 200 nm.
  • the black azo pigment of the present invention is a known pigment as described below in order to adjust the average particle size of the pigment to the required particle size when the pigment synthesized by the above method is coarse. It is necessary to carry out a refinement process and produce a refined pigment.
  • Pigment polishing selected from the group consisting of a ball mill, sand mill, attritor, horizontal continuous media disperser, kneader, continuous uniaxial kneader, continuous biaxial kneader, triple roll, open roll continuous kneader Miniaturization method using a crusher or pigment disperser,
  • a pigment refining step selected from known methods such as a solvent salt milling method of kneading and grinding with a water-soluble salt and, if necessary, a water-soluble organic solvent in a kneader, and an average particle size of about 10 nm.
  • a solvent salt milling method of kneading and grinding with a water-soluble salt and, if necessary, a water-soluble organic solvent in a kneader and an average particle size of about 10 nm.
  • an ultrafine pigment having an average particle diameter of about 10 nm to 50 nm.
  • the particle diameter of the pigment is adjusted according to the intended use.
  • the adjustment of the particle size is controlled mainly by the ratio of the salt to the pigment and the kneading time.
  • the pigment particles be smaller.
  • the dispersion state of fine pigment particles of 10 nm to 50 nm, and further ultra fine pigment particles of 10 nm to 30 nm is preferable.
  • a dissolved state in which molecules are finally dispersed in a carrier for dispersion for example, a plastic medium is desirable.
  • the base is preferably reflective, but the pigment particles may be relatively large and may be used at 100 nm to 200 nm.
  • water-soluble inorganic salts are added to the pigment as a grinding aid, several times the amount of the pigment to be ground depending on the desired pigment particle size, specifically 3 to 20 times the amount. Further, a viscous water-soluble organic solvent such as ethylene glycol, diethylene glycol, polyethylene glycol or the like is added and kneaded and ground.
  • a viscous water-soluble organic solvent such as ethylene glycol, diethylene glycol, polyethylene glycol or the like is added and kneaded and ground.
  • sodium chloride, sodium sulfate and the like are used. After grinding, it is added to dilute sulfuric acid, water, etc. to dissolve the grinding aid, filtered and washed with water to obtain a pigment filtration paste (press cake).
  • the press cake is directly processed by a wet disperser, processed into an oily colorant by a flushing method, dried with hot air, and then pulverized into a powder pigment by a dry pulverizer.
  • various colorants are processed, such as being dispersed by a wet disperser or a kneader. It is also preferable to treat the resin in water to make an easily dispersible processed pigment or processed pigment.
  • an anionic or cationic pigment derivative to the black azo pigment, particularly in a liquid pigment dispersion.
  • a method for adding these pigment derivatives a method of introducing an accessory coupling method using a diazo component or a coupling component having an ionic group at the time of synthesis of the above-mentioned pigment, or a separately synthesized ionic group is used. It is carried out by a known method such as a method in which the pigment derivative is added at the time of the fine particle production process or when preparing the pigment dispersion.
  • chromatic pigment derivatives such as yellow, blue, and red, as well as black, are appropriately used including adjustment of color tone.
  • the spectral transmittance of the coating film is slightly different in numerical values depending on the black pigment content and coating film thickness contained in the coating film, but in relation to the wavelength, it is Has also been shown to exhibit a tendency to absorb, and to exhibit a tendency to transmit at the transmitted wavelength.
  • Tables 1 and 2 the black disazo pigment ("Black Pigment-1") obtained in Production Example 1 of the present invention described later is used, and the coating film containing Black Pigment-1 prepared in Example 1 described later is used.
  • the spectral transmittance (%) in the visible region and the infrared region is shown.
  • the coating film containing Black Pigment-1 has a transmittance of 0% over the entire wavelength region of visible light of 400 to 750 nm, and does not exhibit transparency in the visible region. confirmed.
  • Table 2 there is a 34% transmission at 900 nm in the infrared region, and the transmittance gradually increases on the longer wavelength side, and the transmittance is increased even at higher wavelengths. It is assumed that
  • the volume resistivity value of the coating film containing the black pigment-1 is 10 14 as shown in Example 1 described later. It was ⁇ ⁇ cm, and it was confirmed that good electrical insulation was exhibited.
  • the black pigment-1 which is the black azo pigment of the present invention is a dye having an optical function of transmitting light in the infrared region and completely shielding light in the visible light region as described above, It has been found that it is useful for applications of infrared filters for electronic devices that use BF and for CF BM. For example, when the black azo pigment of the present invention is applied to CF BM, light in the visible light region of the backlight can be completely shielded, and excellent electrical insulation is exhibited.
  • the black azo pigment of the present invention is a coloring composition that, when used, has a dark chromatic color, an achromatic dark color, or a black color, and includes a black azo pigment depending on the purpose, application, usage, etc. It can be used in various forms as a liquid coloring composition containing the components in a liquid dispersion medium or a solid coloring composition containing the components in a solid dispersion medium.
  • the black azo pigment of the present invention has a chromatic color pigment, a white pigment, another black pigment, and an extender pigment as a pigment component, as a pigment component, alone or as one of a plurality of pigment components. In combination, one type or two or more types can be selected and used in combination.
  • the mixing ratio of the chromatic color pigment, white pigment, other black pigment or extender pigment used in combination with the black azo pigment of the present invention to correct the color of the black azo pigment is not particularly limited, but a computer color matching system is used. It is also a preferred form to be determined by the method to be used and optimized.
  • a known pigment can be used and is not particularly limited.
  • Organic pigments such as dioxazine pigments, quinophthalone pigments, nickel azo pigments, metal complex pigments, insoluble azo pigments, soluble azo pigments, high molecular weight azo pigments, azomethine azo black pigments, aniline black pigments, and carbon black pigments
  • At least one pigment selected from inorganic pigments such as composite oxide pigments, iron oxide pigments, titanium oxide pigments, a mixture of two or more pigments, and mixed crystal pigments can be used.
  • Organic pigments include, for example, yellow pigments and C.I. I. Pigment Yellow (abbreviated as PY) -74, 83, 93, 94, 95, 97, 109, 110, 120, 128, 138, 139, 147, 150, 151, 154, 155, 166, 175, 180, 181 , 185, 191 and the like are C.I. I. Pigment Orange (abbreviated as PO) -61, 64, 71, 73, etc. are red pigments such as C.I. I.
  • Pigment Red (abbreviated as PR) -4, 5, 23, 48: 2, 48: 4, 57: 1, 112, 122, 144, 146, 147, 150, 166, 170, 177, 184, 185, 202 , 207, 214, 220, 221, 242, 254, 255, 264, 272, and the like.
  • C.I. I. Pigment Blue (abbreviated as PB)-15: 1, 15: 2, 15: 3, 15: 4, 15: 5, 15: 6, 16, 17: 1, 60, 80, aluminum phthalocyanine blue, etc. are green
  • C.I. I. Pigment Green (abbreviated as PG) -7, 36, 58, poly (13-16) bromophthalocyanine, etc.
  • I. Pigment Violet (abbreviated as PV) -19, PV-23, PV-37, etc. are black pigments such as aniline black pigments, carbon black pigments, titanium oxide black pigments, and particularly for CF BM.
  • a carbon black pigment, a titanium oxide black pigment or the like whose surface is treated to improve insulation is preferable.
  • the black azo pigment of the present invention is used in combination with an infrared reflective pigment such as a white pigment
  • the methods proposed in Japanese Patent No. 4097926 and Japanese Patent Application Laid-Open No. 2005-330466 can also be used. That is, it is also preferable to apply a method of substantially improving the infrared reflection efficiency by substantially covering the infrared reflective pigment such as a white pigment with the infrared transmissive black azo pigment of the present invention.
  • the liquid coloring composition comprising the black azo pigment of the present invention is mainly used as a coloring agent for coating, impregnating, drawing, printing, etc. on the surface of an article, and it is used as a paint, coating agent, plastic coloring, fiber coloring. , Printing ink, stationery, image recording, and image display.
  • a reactive polymer having a reactive group or a non-reactive polymer, an oligomer having a reactive group, or a non-reactive polymer is used as a film-forming material (or film-forming material).
  • It may contain at least one selected from a reactive oligomer, a monomer having a reactive group, a non-reactive monomer having no reactive group, and the like, and may itself be a liquid, or further It may contain a solvent and / or water.
  • the pigment to be used is prepared in advance as a high-concentration pigment processed product in which the pigment to be used is finely dispersed in a dispersion medium, it is used for coloring.
  • the preparation of the agent can be facilitated.
  • the liquid high-concentration pigment dispersion is called “base color” or “base ink” and is used.
  • the above-described solid coloring composition containing the black azo pigment of the present invention is a colorant mainly used for internal coloring of plastics and synthetic fibers, and is, for example, a high-concentration pigment dispersion. It is used in known product shapes such as master powder, master batch, etc., and colored pellets colored throughout.
  • the solid dispersion medium at least one selected from thermoplastic resins, thermosetting resins, waxes, fatty acid amides, fatty acid metal soaps, and the like can be used.
  • the black azo pigment of the present invention when used, particularly in the wavelength range of about 400 to 750 nm in the visible light region, high absorptivity and visible light shielding properties are exhibited, and a high wavelength of about 900 nm to 1500 nm and further higher. In the infrared region, it can be colored highly transmissive.
  • the material constituting the article itself is light-reflective or a pre-formed light-reflective substrate is used. Furthermore, it can achieve by apply
  • the coloring method in this case is a known method, for example, painting, painting, undiluted solution printing, textile printing, dip dyeing, printing, writing, drawing, ink jet printing, electrophotographic printing, electrostatic printing, etc. Can exhibit high absorbency, and in the near-infrared region can be colored highly reflective.
  • the spectral reflectance of the black pigment-1 was measured, and the results are shown in Table 3.
  • the measured sample is a coated paper (hereinafter referred to as black developed paper) coated on a white developed paper using an applicator.
  • the coating film containing the above black pigment-1 absorbs from the visible region to about 750 nm and exhibits a reflectance of about 5%, but the reflectance rapidly increases from about 800 nm to 900 nm. It is assumed that the reflectance of about 80% is maintained in the near-infrared region on the longer wavelength side, and that the reflectance is also high in the infrared region of higher wavelength. . This indicates that the light that has passed through the black coating is reflected by the white paper of the base, and the surface of the black pigment can be obtained by using a highly reflective base or a reflective material such as a white pigment or extender. In addition to the above, the transmitted light is re-reflected to show an efficient high reflectance.
  • Resin binder that functions as a film-forming material (film-forming material) used in the present invention is a non-reactive, room-temperature drying type or reaction that does not have a reactive group.
  • a baking-type resin binder having a functional group and a photosensitive resin binder can be preferably used.
  • the room temperature drying type or baking type resin binder include printing agents, paints, coating agents, or resin binders used for printing inks, stationery, inkjet printing, electrophotographic printing, electrostatic printing, and other image recording materials. Is mentioned.
  • the photosensitive resin binder include photosensitive resin binders used in various ultraviolet curable or electron beam curable paints, coating agents, printing inks, inkjet inks, photolithography, and the like.
  • room temperature drying type or baking type resin binders that can be used in the present invention include, for example, synthetic rubber resins, acrylic resins, styrene (co) polymers, vinyl resins such as polyvinyl butyral resins, and polyester resins.
  • Amino resin-modified polyester resins polyurethane resins, acrylic polyol urethane resins, soluble polyamide resins, soluble polyimide resins, soluble polyamideimide resins, soluble polyesterimide resins, alkyd resins, aminoalkyd resins, epoxy resins Resin, chlorinated rubber resin, silicone resin, fluororesin, cellulose acetate resin, nitrocellulose resin, hydroxyethyl cellulose, water-soluble salt of styrene-maleic acid ester copolymer, (meth) acrylic acid ester (co) heavy Body water-soluble salts of water-soluble amino alkyd resin, and water-soluble amino polyester resin and a water-soluble polyamide resin and the like, which are used in combination or alone or in combination.
  • Examples of the reactive group possessed by the reactive film forming material include a methylol group, an alkylmethylol group, an isocyanate group, a masked isocyanate group, and an epoxy group.
  • oligomers and monomers are used depending on applications, and a cross-linking agent such as methylol melamine type, isocyanate type, and epoxy type cross-linking agent is also used in combination.
  • energy ray curable coating film forming materials such as ultraviolet curable resin systems and electron beam curable resin systems
  • energy ray curable coating film forming materials include, for example, photosensitive cyclized rubber resins, photosensitive phenol resins, Photosensitive polyacrylate resins, photosensitive polyamide resins, photosensitive polyimide resins, etc., and unsaturated polyester resins, polyester acrylate resins, polyepoxy acrylate resins, polyurethane acrylate resins, polyether acrylate resins, polyols
  • binders such as acrylate resins, and binders in which monomers are further added as reactive diluents.
  • plastic to be colored with the colorant for plastics which is the coloring composition of the present invention examples include conventionally known thermoplastics such as polyolefins such as polyethylene, ethylene copolymer, and polypropylene, polystyrene, ABS, AS, and styrene. Copolymers, vinyl chloride resins, methacrylic resins, polycarbonates, polyamides, polyacetals, thermoplastic polyesters, cellulosic plastics, phenylene oxide resins, fluororesins, thermoplastic elastomers, etc. Also, as thermosetting plastics, unsaturated polyester resins, Examples thereof include an epoxy resin, a silicone resin, a polyurethane resin, a melamine resin, and a phenol resin.
  • thermoplastics such as polyolefins such as polyethylene, ethylene copolymer, and polypropylene, polystyrene, ABS, AS, and styrene. Copolymers, vinyl chloride resins, methacryl
  • the content of the black azo pigment of the present invention contained in the black colorant which is the coloring composition of the present invention varies depending on the use and purpose of use, and is not generally determined.
  • the content of black pigment contained in the colorant is as follows: It is about 3% to 80%, preferably about 5% to 60%.
  • the pigment when used as a light-shielding black material for CF BM, since the film thickness is particularly thin and complete light-shielding properties are required, the pigment is stably dispersed, the viscosity suitable for coating is maintained, and uniform
  • the limit pigment concentration to form a simple colored film is tried, and is preferably about 30% to 60%.
  • the entire material to be colored is internally colored, such as plastic coloring or spinning stock solution coloring, it depends on the thickness of the colored product, but it is approximately 0.05% to 20%, preferably approximately 0%. About 1% to 10%.
  • the coloring composition for image recording containing the black azo pigment of the present invention is used as a coloring composition for BM formation of CF
  • the coloring composition is used to transfer directly or onto the CF substrate. It is formed by one or two or more forming methods selected from a photolithography method, a laser ablation method, an ink jet printing method, a printing method, a transfer method, a pasting method, etc. with a plastic film for pasting interposed.
  • the film thickness of BM is 0.5 ⁇ m to 3 ⁇ m, and usually 1 ⁇ m to 2 ⁇ m.
  • the optical density (OD) value is 2.0 or more, preferably 3.0 or more.
  • OD optical density
  • chromatic color pixels can be formed on the CF substrate on which the BM is formed by a known pixel forming method using a known chromatic color pixel forming colorant.
  • a CF substrate or an organic EL light emitting substrate on which a BM that absorbs a wavelength range in the visible region is formed in particular, a BM is further substantially electrically insulating, and a CF substrate that is formed by overlapping the BM and an electrode.
  • An organic EL light emitting substrate and a color display panel including them are exemplified.
  • An organic EL color display device equipped with a light emitting substrate may be mentioned.
  • seat formed by multilayering the dark-colored infrared rays transparent layer and a solar power generation module using the same are mentioned.
  • the obtained ground product was stirred for 1 hour in 3,000 parts of warm water heated to 80 ° C. and then filtered, and the resulting filtrate was washed with water to remove sodium chloride and diethylene glycol. As a result, a miniaturized black azo pigment press cake was obtained.
  • the particle diameter of the pigment obtained above was measured by the following method. A transmission electron micrograph (60,000 times) of the obtained black pigment was taken, and the particle size distribution was measured using “image analysis type particle size distribution software Mac-View” (manufactured by Mountec). As a result, the average particle size was 50 nm. Also in other production examples, the average particle diameter of the pigment was measured by the same method as described above.
  • black pigment-1 A finely divided powder pigment of black pigment having the structure of (carbazole-3-carboxy-p-anisidide) was obtained. Hereinafter, it is referred to as “black pigment-1”.
  • the obtained crude pigment was refined.
  • the method was refined according to Production Example 1 (2) except that the amount of sodium chloride used in (2) described in Production Example 1 was 8 times the amount of the pigment. .
  • dissolving salt etc. with acidic water it filtered, and the obtained filtrate was washed with water, and the press cake of the black azo pigment was obtained.
  • the average particle diameter of the obtained pigment was 25 nm.
  • miniaturization process was performed according to (2) described in manufacture example 1 except having used the usage-amount of sodium chloride used in (2) described in manufacture example 1 10 times with respect to a pigment. And after melt
  • the press cake obtained above was dried and then pulverized to obtain a finely divided powder pigment of black pigment. Hereinafter, this is referred to as “black pigment-3”.
  • the obtained crude pigment was refined.
  • Refinement treatment was carried out according to (2) described in Production Example 1, and after salt and the like were dissolved in acidic water and filtered, the obtained filtrate was washed with water to obtain a black azo pigment press cake.
  • the average particle diameter of the obtained pigment was 50 nm.
  • the press cake obtained above was dried and then pulverized to obtain a finely divided powder pigment of black pigment.
  • black pigment-4 this is referred to as “black pigment-4”.
  • black azo pigment crude pigment obtained above was pulverized with a dry pulverizer to obtain a finely divided powder pigment of black pigment.
  • the average particle diameter of the obtained pigment was 110 nm.
  • black pigment-6 this is referred to as “black pigment-6”.
  • Black Pigment-7 The black pigment-1 press cake obtained in (1) described in Production Example 1 and the black pigment derivative-1 press cake obtained in (1) above have a pigment solid content ratio of 10: 1. And mixed well so as to be uniform. And the crude pigment of the black pigment containing a pigment derivative was obtained by drying the said mixture. Next, the pigment was refined in accordance with (2) described in Production Example 1, and then the salt and the like were dissolved with acidic water, and this was filtered. A pigment presscake was obtained. The average particle diameter of the obtained pigment was 50 nm. The press cake was dried and pulverized to obtain a fine powder pigment of a black pigment containing an anionic pigment derivative. Hereinafter, this is referred to as “black pigment-7”.
  • the press cake of the obtained cationic pigment derivative and the press cake of black pigment-1 obtained in Production Example 1 (1) were blended so that the solid content ratio was 85:15. These were mixed sufficiently to be uniform and then dried to obtain a black pigment crude pigment containing a cationic pigment derivative.
  • the obtained crude pigment is subjected to a fine treatment according to the method of (2) described in Production Example 1, and then filtered by dissolving a salt and the like with water and washing the filtrate with water.
  • An azo pigment presscake was obtained.
  • the average particle diameter of the obtained pigment was 50 nm.
  • the obtained press cake was dried and then pulverized to obtain a finely divided powder pigment of a black pigment containing a cationic yellow pigment derivative.
  • black pigment-8 this is referred to as “black pigment-8”.
  • Example 1 Evaluation of optical properties of coating film containing black pigment-1 of Production Example 1
  • a black coating solution was prepared.
  • a 50% xylene-butanol mixed solvent solution of an acrylic resin having a carboxyl group (acid value is 10 mg KOH / g) and a 50% xylene-butanol mixed solvent solution of a butylated methylol melamine resin are in a ratio of 80:20.
  • a varnish As a varnish to be used, a 50% xylene-butanol mixed solvent solution of an acrylic resin having a carboxyl group (acid value is 10 mg KOH / g) and a 50% xylene-butanol mixed solvent solution of a butylated methylol melamine resin are in a ratio of 80:20.
  • a diluting solvent a mixed solvent of xylene-butanol (4: 1) was used. (Hereinafter, this is referred to as “diluting solvent”.)
  • the coating film containing Black Pigment-1 has a spectral transmittance of 0% over the entire wavelength region of 400 to 750 nm in the visible light region. It was confirmed that almost no transmission occurred (see Table 4). On the other hand, in the infrared region, the transmittance at 900 nm was approximately 34%, and it was confirmed that the transmittance gradually increased on the longer wavelength side (see Table 5).
  • Example 2 Evaluation of light reflection characteristics of coating film containing black pigment-1 of Production Example 1
  • the black coating solution prepared in (1) described in Example 1 was used with a 6 mil applicator. After coating on white color paper, it was dried and cured to obtain a black color paper (hereinafter referred to as black color paper) formed by forming a coating film.
  • the measured value of the dry film thickness of the black coating film formed on the black color developed paper was approximately 35 to 40 nm on the color developed paper.
  • the black color paper produced using the black pigment-1 shows only a reflectance of 5 to 6% up to about 750 nm, but the reflectance increases rapidly from 800 nm to 900 nm. Further, it was confirmed that the reflectance of approximately 70% to 80% or more was maintained in the near infrared region on the longer wavelength side. For these reasons, the light reflectance of the black color developed paper is high because the reflected light is reflected by the base white paper together with the reflection from the pigment surface, and the resulting light is added to become reflected light. It is considered a thing. Therefore, it is shown that near infrared rays can be efficiently reflected by increasing the light transmittance of the black pigment and using a highly reflective base. In Table 6 above, the reflectance is not 0% up to about 750 nm but a value of 5% because of the relationship with the measuring apparatus.
  • Example 3 (1) In the same manner as in Example 1, black pigments 2 to 6 obtained in Production Examples 2 to 6 were respectively used to prepare black coating films. The spectral transmittance of the outer region was measured. Tables 7 and 8 show the results.
  • Example 2 In the same manner as in Example 2, a black coating film was formed using each of the black pigments 2 to 6 obtained in Production Examples 2 to 6, and black colored paper was prepared. The dry film thickness of the black coating film was about 35 to 40 nm on the black color developed paper. The spectral reflectance was measured in the same manner as in Example 2. As a result, as shown in Table 9, the spectral reflectance showed the same tendency as that of the black coated color developed paper obtained using the black pigment-1.
  • Example 4 Polycarbonate resin molded plate After 20 parts of black pigment-2 prepared in Production Example 2 and 80 parts of polycarbonate resin powder were sufficiently mixed with a Henschel mixer (powder high speed mixer), they were further mixed and kneaded with a twin screw extruder, A polycarbonate resin black masterbatch containing 20% of black pigment-2 was prepared. 2 parts of the obtained black masterbatch was mixed with 100 parts of polycarbonate resin pellets made of the same resin powder as described above, mixed with a Henschel mixer, then mixed and kneaded with a twin screw extruder to obtain black resin pellets. .
  • the obtained black resin pellet was molded by an in-line screw injection molding machine to obtain a black polycarbonate resin plate excellent in pigment dispersibility. Since this black resin plate absorbs light in the visible light region and can sufficiently transmit near infrared rays, it can be used for applications such as an infrared transmission filter.
  • Example 5 (Acrylic resin molding plate)
  • 20 parts of the black pigment-3 prepared in Production Example 3 and 80 parts of acrylic resin (polymethyl methacrylate) powder were sufficiently mixed with a Henschel mixer, and then further biaxial extrusion kneading.
  • an acrylic resin black masterbatch containing 20% of black pigment-3 was prepared.
  • the mixture was further mixed with a Henschel mixer, and further mixed and kneaded with a twin-screw extrusion kneader. It was.
  • the obtained black resin pellet was molded by an in-line screw injection molding machine to obtain a black acrylic resin plate excellent in pigment dispersibility. Since this black resin plate absorbs light in the visible light region and can sufficiently transmit near infrared rays, it can be used as an infrared transmission filter.
  • Example 6 Polyurethane coating agent 15 parts of black pigment-4 prepared in Production Example 4, 10 parts of polycarbonate non-yellowing polyurethane resin, and 75 parts of dimethylformamide (hereinafter referred to as “DMF”) are mixed with black pigment and non-yellowing polycarbonate. A modified polyurethane resin solution, DMF, is prepared. This prepared liquid was sufficiently dispersed with a horizontal continuous medium disperser to obtain a black pigment high-concentration dispersion.
  • DMF dimethylformamide
  • the black coating solution prepared above was applied to a release paper DNTP-155T-FLAT (trade name, manufactured by Dai Nippon Printing Co., Ltd.) so as to have a film thickness of 50 ⁇ m, and then 100 ° C./10 minutes. It was dried under conditions to form a skin layer.
  • DNTP-155T-FLAT trade name, manufactured by Dai Nippon Printing Co., Ltd.
  • 10 parts of toluene as a diluting solvent 20 parts of MEK
  • MEK methyl ethyl ketone
  • a mixture of 20 parts of DMF, 10 parts of a modified polyisocyanate crosslinking agent (solid content 75%, ethyl acetate solvent) and 0.15 part of an amine crosslinking catalyst solid content 0.5% MEK solvent was prepared. .
  • this adhesive agent in the sheet form so that it might become a film thickness of 75 micrometers on the surface of a skin layer (surface on the opposite side to the surface which is in contact with release paper), it was dried on condition of 80 degreeC / 5 minutes.
  • the obtained sheet having the adhesive layer and the skin layer is laminated on the base material (woven fabric) on the adhesive layer side to obtain a laminate having a total thickness of 1,100 ⁇ m, and the obtained laminate is heated to 100 ° C.
  • the laminate roll was pressed and adhered with a gap of 500 ⁇ m.
  • the product was peeled from the release paper to obtain a synthetic artificial leather.
  • the obtained synthetic artificial leather is excellent in durability such as heat deterioration resistance, hydrolysis deterioration resistance, light deterioration resistance, oleic acid resistance, etc. in addition to reduction (reduction) of heat storage, and is suitable for vehicle use etc. It was a thing.
  • the adhesive used above is colored white by containing a white pigment, thereby giving the adhesive layer light reflectivity and exhibiting both visible light shielding properties and infrared transmittance optical properties.
  • a polyurethane synthetic leather capable of reflecting heat rays was obtained. This synthetic leather is particularly suitable for applications such as automobile interiors.
  • Example 7 (Stock solution colored spinning) 50 parts of black pigment-5 prepared in Production Example 5 and 50 parts of ethylenebisstearic acid amide powder as a pigment dispersant were mixed with a Henschel mixer to obtain a powder colorant (dry color) having a pigment content of 50%. Obtained. Next, 1.0 part of the obtained dry color was blended in 99.0 parts of polypropylene resin pellets, mixed with a Henschel mixer, and further kneaded with a vent type 40 m / m extruder, so that the pigment content was 0. A 5% black resin pellet was prepared.
  • the obtained black resin pellets were spun by a melt spinning machine to obtain a clear black polypropylene stock solution colored yarn having a fineness of 10 denier and excellent pigment dispersibility. Since the woven fabric made using this colored yarn can reflect the heat rays of direct sunlight, the effect of avoiding the temperature rise is expected. Therefore, it is particularly suitable for uses such as parasols and curtains.
  • Example 8 (Resin molding) 5 parts of black pigment-6 prepared in Production Example 6, 20 parts of titanium oxide white pigment, and 75 parts of polyethylene resin powder as a pigment dispersant were mixed with a Henschel mixer to obtain a powder colorant (dry color). It was. Next, 1.0 part of the obtained powder colorant was blended in 100 parts of polybutylene terephthalate (PBT) resin pellets, mixed with a Henschel mixer, and then kneaded with an extruder to obtain black resin pellets. The obtained black pellet was molded with an in-line screw injection molding machine to obtain a black PBT resin molded plate excellent in pigment dispersibility. The obtained resin molded board was able to reflect the heat rays of direct sunlight. For this reason, this resin is suitable for use as a molded resin product in which it is desirable to avoid an increase in temperature.
  • PBT polybutylene terephthalate
  • Example 9 Heat-shielding back sheet for photovoltaic module (1) 15 parts of black pigment-4 prepared in Production Example 5, 15 parts of an acrylic polyol (hydroxyl value: 100) butyl acetate solution (solid content 50%), and 50 parts of butyl acetate were sufficiently premixed and dispersed. A black pigment high-concentration dispersion was prepared by dispersing the pigment using a horizontal continuous medium disperser using glass beads as a medium. Acrylic polyol (hydroxyl value: 100) butyl acetate obtained by copolymerizing 22 parts of an acrylic polyol butyl acetate solution similar to the above, benzotriazole monomer and HALS monomer in 90 parts of the black pigment high-concentration dispersion obtained above.
  • a white pigment high-concentration dispersion was prepared by dispersing the pigment with a medium disperser. To 140 parts of the white pigment high-concentration dispersion obtained above, 44 parts of an acrylic polyol butyl acetate solution was added to obtain a white ink. Then, 18 parts of the same hexamethylene diisocyanate trimer used previously as a curing agent was added to this white ink, and after mixing well, approximately 40 parts of butyl acetate was added to adjust the viscosity. A white coating solution was prepared.
  • the black coating solution prepared in (1) above is applied to the surface of a polyethylene terephthalate (PET) substrate sheet (film thickness: 100 ⁇ m), dried, and a black coating film (dry film thickness: 5 ⁇ m) Formed. Furthermore, the white coating liquid obtained in the above (2) is applied to the back surface of the base material and dried to form a white coating film (dry film thickness: 5 ⁇ m). A black-white multilayer PET sheet obtained by applying a white coating film to the film was obtained.
  • PET polyethylene terephthalate
  • a silica / alumina-deposited polyester film (film) (Thickness: 12 ⁇ m) was laminated, and a PET substrate sheet (film thickness: 100 ⁇ m) was further laminated thereon to produce a PET back sheet for a photovoltaic power generation module.
  • the following adhesives were used for the above lamination.
  • an adhesive composed of 70 parts of the same acrylic polyol solution as used in the above (1), 15 parts of hexamethylene diisocyanate trimer and 15 parts of butyl acetate was used.
  • the PET backsheet coated with the black coating film and the white coating film obtained as described above is excellent in aesthetics because of its black appearance, and the optical characteristics of the black pigment-4 used.
  • the backsheet obtained above is used as a photovoltaic power generation module, it may be used as follows according to a conventional method. That is, the photovoltaic cell is sandwiched and sealed with a sealing material made of ethylene vinyl acetate resin, a surface sealing sheet is pasted on the surface on the light receiving surface side, and the above-described light shielding is used as a protective sheet on the non-light receiving surface side on the back surface.
  • a solar power generation module can be produced by attaching a transparent glass substrate to the light receiving surface after bonding the black surface of the conductive back sheet toward the light receiving side.
  • Example 10 Heat-shielding back sheet for photovoltaic module (1) 40 parts of the black pigment-6 obtained in Production Example 6 and 60 parts of polyester resin powder were mixed with a Henschel mixer to obtain a powdery colorant. Next, 12.5 parts of the obtained powdery colorant was blended in 87.5 parts of PET resin pellets, mixed with a Henschel mixer, then kneaded with a twin screw extruder, and made into black resin pellets with a pelletizer. Subsequently, it was molded by a T-die extruder to prepare a black PET film having a film thickness of 50 ⁇ m.
  • a white PET sheet (film thickness: 180 ⁇ m) kneaded and colored with a titanium oxide pigment was prepared. And by sticking the black PET film obtained by said (1) on the surface using the same acrylic polyol hexamethylene diisocyanate adhesive as described in (9) of Example 9, black PET A white PET sheet laminated with a film was prepared.
  • the back sheet for a photovoltaic power generation module using the sheet obtained by laminating the black film and the white PET sheet obtained above is black in appearance and excellent in aesthetics, and from the optical characteristics of the used black pigment-6, It has the following optical properties. That is, infrared light of sunlight passes through the black film layer on the surface, is reflected by the lower white PET sheet, passes through the black film again, and is emitted to the outside. Therefore, the black-white multi-layer PET sheet is a back sheet for a photovoltaic power generation module that absorbs less sunlight and exhibits excellent heat shielding properties. Particularly preferred.
  • the backsheet obtained above is used as a photovoltaic power generation module, it may be used as follows according to a conventional method. That is, the photovoltaic cell is sandwiched and sealed with a sealing material made of ethylene vinyl acetate resin, a surface sealing sheet is pasted on the surface on the light receiving surface side, and the above-mentioned light shielding as a protective sheet on the non-light receiving surface side on the back surface.
  • a solar power generation module can be produced by attaching a transparent glass substrate to the light receiving surface after bonding the black surface of the conductive back sheet toward the light receiving side.
  • Example 11 Print paste for woven fabric
  • a press cake containing 25 parts of the solid content of the black pigment-1 obtained in Production Example 1
  • the pigment was dispersed with a horizontal continuous medium disperser using glass beads to prepare a black pigment high-concentration dispersion (black color base).
  • Example 12 (gravure printing ink) 11 parts of the black pigment-10 obtained in Production Example 10 and 30 parts of a 40% methyl ethyl ketone-toluene (1: 3) mixed solvent solution of a polyurethane resin in which the isocyanate-terminated polyester was chain-extended with diamine were added.
  • a mixed solvent of methyl ethyl ketone-toluene-isopropyl alcohol 50:30:20
  • the above mixture was finely dispersed with a horizontal continuous medium disperser using glass beads as a dispersion medium to prepare a black gravure printing ink.
  • the resulting black gravure printing ink is printed on a polyamide film, a polyester film, and a polypropylene film by using a gravure printing machine, respectively, and a black polypropylene film that exhibits optical characteristics of shielding visible light and transmitting infrared light.
  • Example 13 (Formation of CF BM) (1) (Preparation of pigment dispersion for BM) (Preparation of black pigment dispersion) 25 parts of the black pigment-9 obtained in Production Example 9 and a 40% solution of benzyl methacrylate-methacrylic acid-2-hydroxyethyl methacrylate copolymer (molar ratio: 60:20:20, weight average molecular weight 30,000). 20 parts, 2 parts of a cationic polymer dispersant and 53 parts of propylene glycol monomethyl ether acetate (PGMA) were sufficiently premixed. Next, the pigment was finely dispersed using a continuous horizontal medium disperser to obtain a black pigment dispersion (hereinafter referred to as “black pigment dispersion-1”).
  • black pigment dispersion-1 a black pigment dispersion
  • photosensitive black resist ink-1 a black resist ink containing black pigment-9 (hereinafter referred to as “photosensitive black resist ink-1”). Called).
  • the BM film forming the BM pattern obtained above exhibits high electrical insulation as described in (3) above, various CF improvement methods for forming a BM on an active element such as a TFT For example, it can be used for the construction of a BM, IPS system, COA system, etc. that retains the thickness of the liquid crystal layer instead of the spacer. Further, since the BM film can sufficiently absorb the visible region up to the long wavelength region, it can also be used as a BM of an LCD panel employing an LED backlight.
  • a red resist ink was prepared by adding 9.2 parts% solution, 3 parts photopolymerizable monomer, 0.3 part photopolymerization initiator, and 54.5 parts solvent.
  • a pigment dispersion containing PG36 and PY138 is blended at a ratio of 5: 5 to give a green resist ink, and 8 pigment dispersions containing PB15: 6 and PV23, respectively.
  • Blue resist inks were prepared by blending at a ratio of 2.
  • a photosensitive black resist ink was prepared in the same manner as described above except that the black pigment-7 obtained in Production Example 7 was used instead of the black pigment-9 used above, and the BM pattern described above was prepared. And RGB pixel pattern was formed, and CF with BM and RGB pixels was obtained.
  • Example 14 (Formation of CF BM) (1) (Preparation of pigment dispersion for BM) (Preparation of black pigment dispersion) As in Example 13 (1), 25 parts of black pigment-8 instead of black pigment-9, 40% of the same benzyl methacrylate-methacrylic acid-2-hydroxyethyl methacrylate copolymer as used previously After sufficiently premixing 25 parts of the solution and 53 parts of propylene glycol monomethyl ether acetate (PGMA), the pigment was dispersed with a continuous horizontal medium disperser to obtain a black pigment dispersion. Hereinafter, this is referred to as “black pigment dispersion-2”.
  • black pigment dispersion-2 this is referred to as “black pigment dispersion-2”.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Optical Filters (AREA)
  • Paints Or Removers (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)
  • Photovoltaic Devices (AREA)
  • Ink Jet (AREA)
  • Pigments, Carbon Blacks, Or Wood Stains (AREA)

Abstract

La présente invention est un pigment azoïque noir qui a à la fois les propriétés optiques d'une propriété de protection contre le rayonnement visible et d'une propriété de transmission des rayons infrarouges, et qui a une structure qui a, dans la molécule de celle-ci, au moins deux liaisons azoïques et au moins un résidu d'amide d'acide 2-hydroxy-11H-benzo[a]-carbazole-3-carboxylique dérivé d'un composant de couplage, où le pigment azoïque noir est caractérisé en ce qu'il a un diamètre de particule moyen de 10-200 nm. La présente invention permet d'obtenir : un pigment noir qui possède d'excellentes propriétés physiques et solidité de couleur en tant que pigment, peut être utilisé dans des applications d'utilisations différentes, et possède à la fois des propriétés optiques de propriété de protection contre le rayonnement visible et de propriété de transmission des rayons infrarouges ; un procédé de production du pigment ; une composition colorée contenant le pigment ; et un procédé de coloration et un article coloré, dans chacun desquels la composition colorée est utilisée.
PCT/JP2011/080370 2010-12-28 2011-12-28 Pigment azoïque noir et procédé de production de celui-ci, composition colorée, procédé de coloration et articles colorés WO2012091083A1 (fr)

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CN201180063596.4A CN103282443B (zh) 2010-12-28 2011-12-28 黑色偶氮色素、制造方法、着色组合物、着色方法及着色物品类
KR1020137019523A KR101638669B1 (ko) 2010-12-28 2011-12-28 흑색 아조 색소, 제조방법, 착색 조성물, 착색방법 및 착색 물품류

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WO2014103628A1 (fr) * 2012-12-27 2014-07-03 富士フイルム株式会社 Composition pour filtre coloré, filtre d'émission infrarouge et procédé de fabrication de filtre d'émission infrarouge et capteur infrarouge
JP2014125588A (ja) * 2012-12-27 2014-07-07 Teijin Ltd ポリエステル組成物およびポリエステル成形品
JP2014130338A (ja) * 2012-11-29 2014-07-10 Fujifilm Corp 組成物、赤外線透過フィルタ及びその製造方法、並びに赤外線センサー
JP2014160202A (ja) * 2013-02-20 2014-09-04 Jsr Corp 硬化性組成物、着色画素及びその形成方法、並びにカラーフィルタ
JP2014534982A (ja) * 2011-06-06 2014-12-25 ピーピージー・インダストリーズ・オハイオ・インコーポレイテッドＰＰＧ Ｉｎｄｕｓｔｒｉｅｓ Ｏｈｉｏ，Ｉｎｃ． 赤外線放射を透過させ色安定性を示すコーティング組成物および関連のコーティング系
WO2015166779A1 (fr) * 2014-05-01 2015-11-05 富士フイルム株式会社 Composition colorante, film, filtre couleur, procédé de formation de motif, procédé de fabrication de filtre couleur, dispositif d'imagerie à semi-conducteur, et capteur infrarouge
WO2016098810A1 (fr) * 2014-12-19 2016-06-23 旭硝子株式会社 Filtre optique et dispositif l'utilisant
JP2016153471A (ja) * 2015-01-20 2016-08-25 東洋紡株式会社 赤外光透過性ポリエステル樹脂組成物
WO2016190162A1 (fr) * 2015-05-22 2016-12-01 富士フイルム株式会社 Composition colorante, film, filtre couleur, procédé de formation d'un motif, procédé de fabrication d'un filtre couleur, dispositif d'imagerie à semi-conducteurs, et capteur infrarouge
JP2017116955A (ja) * 2017-03-03 2017-06-29 富士フイルム株式会社 赤外線透過フィルタ用組成物、赤外線透過フィルタ、赤外線透過フィルタの製造方法、及び、赤外線センサー
JP2018120248A (ja) * 2018-04-19 2018-08-02 富士フイルム株式会社 赤外線透過フィルタ用組成物、赤外線透過フィルタ、赤外線透過フィルタの製造方法、及び、赤外線センサー
JP2019049759A (ja) * 2018-12-26 2019-03-28 富士フイルム株式会社 赤外線透過フィルタ用組成物、赤外線透過組成物層、赤外線透過フィルタ、赤外線透過フィルタの製造方法、及び、赤外線センサー
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TW201241098A (en) 2012-10-16
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KR20130108650A (ko) 2013-10-04
TWI478983B (zh) 2015-04-01
CN103282443A (zh) 2013-09-04
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