US20080258118A1 - Colored composite microparticles, process for producing the colored composite microparticles, colorant, color filter and ink for ink-jet printing - Google Patents

Colored composite microparticles, process for producing the colored composite microparticles, colorant, color filter and ink for ink-jet printing Download PDF

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Publication number
US20080258118A1
US20080258118A1 US12/073,465 US7346508A US2008258118A1 US 20080258118 A1 US20080258118 A1 US 20080258118A1 US 7346508 A US7346508 A US 7346508A US 2008258118 A1 US2008258118 A1 US 2008258118A1
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Prior art keywords
color filters
ink
particles
colorant
coloring composition
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US12/073,465
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Inventor
Shinji Horie
Hiroko Morii
Hirofumi Nishikawa
Kazuyuki Hayashi
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Toda Kogyo Corp
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Toda Kogyo Corp
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Priority claimed from JP2006172462A external-priority patent/JP5093442B2/ja
Priority claimed from JP2006194645A external-priority patent/JP2008019399A/ja
Application filed by Toda Kogyo Corp filed Critical Toda Kogyo Corp
Assigned to TODA KOGYO CORPORATION reassignment TODA KOGYO CORPORATION ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: HAYASHI, KAZUYUKI, HORIE, SHINJI, MORII, HIROKO, NISHIKAWA, HIROFUMI
Publication of US20080258118A1 publication Critical patent/US20080258118A1/en
Priority to US12/926,485 priority Critical patent/US8303861B2/en
Abandoned legal-status Critical Current

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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
    • C09C—TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK  ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
    • C09C1/00—Treatment of specific inorganic materials other than fibrous fillers; Preparation of carbon black
    • C09C1/28—Compounds of silicon
    • C09C1/30—Silicic acid
    • C09C1/309—Combinations of treatments provided for in groups C09C1/3009 - C09C1/3081
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09C—TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK  ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
    • C09C1/00—Treatment of specific inorganic materials other than fibrous fillers; Preparation of carbon black
    • C09C1/28—Compounds of silicon
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B82—NANOTECHNOLOGY
    • B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
    • B82Y30/00—Nanotechnology for materials or surface science, e.g. nanocomposites
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09C—TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK  ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
    • C09C1/00—Treatment of specific inorganic materials other than fibrous fillers; Preparation of carbon black
    • C09C1/0081—Composite particulate pigments or fillers, i.e. containing at least two solid phases, except those consisting of coated particles of one compound
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09C—TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK  ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
    • C09C1/00—Treatment of specific inorganic materials other than fibrous fillers; Preparation of carbon black
    • C09C1/28—Compounds of silicon
    • C09C1/30—Silicic acid
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09C—TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK  ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
    • C09C1/00—Treatment of specific inorganic materials other than fibrous fillers; Preparation of carbon black
    • C09C1/28—Compounds of silicon
    • C09C1/30—Silicic acid
    • C09C1/3063—Treatment with low-molecular organic compounds
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09C—TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK  ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
    • C09C1/00—Treatment of specific inorganic materials other than fibrous fillers; Preparation of carbon black
    • C09C1/28—Compounds of silicon
    • C09C1/30—Silicic acid
    • C09C1/3081—Treatment with organo-silicon compounds
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09C—TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK  ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
    • C09C3/00—Treatment in general of inorganic materials, other than fibrous fillers, to enhance their pigmenting or filling properties
    • C09C3/08—Treatment with low-molecular-weight non-polymer organic compounds
    • 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
    • C09D11/00—Inks
    • C09D11/30—Inkjet printing inks
    • C09D11/32—Inkjet printing inks characterised by colouring agents
    • C09D11/322—Pigment inks
    • 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
    • C09D17/00—Pigment pastes, e.g. for mixing in paints
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • G02B5/201—Filters in the form of arrays
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
    • C01P2004/00—Particle morphology
    • C01P2004/60—Particles characterised by their size
    • C01P2004/64—Nanometer sized, i.e. from 1-100 nanometer
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
    • C01P2006/00—Physical properties of inorganic compounds
    • C01P2006/12—Surface area
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
    • C01P2006/00—Physical properties of inorganic compounds
    • C01P2006/22—Rheological behaviour as dispersion, e.g. viscosity, sedimentation stability
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
    • C01P2006/00—Physical properties of inorganic compounds
    • C01P2006/60—Optical properties, e.g. expressed in CIELAB-values
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
    • C01P2006/00—Physical properties of inorganic compounds
    • C01P2006/60—Optical properties, e.g. expressed in CIELAB-values
    • C01P2006/62—L* (lightness axis)
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
    • C01P2006/00—Physical properties of inorganic compounds
    • C01P2006/60—Optical properties, e.g. expressed in CIELAB-values
    • C01P2006/64—Optical properties, e.g. expressed in CIELAB-values b* (yellow-blue axis)
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
    • C01P2006/00—Physical properties of inorganic compounds
    • C01P2006/60—Optical properties, e.g. expressed in CIELAB-values
    • C01P2006/65—Chroma (C*)

Definitions

  • the present invention relates to colored composite microparticles, a dispersion containing the colored composite microparticles, a process for producing the colored composite microparticles, a colorant for color filters, a coloring composition for color filters containing the colorant, a color filter, a colorant for inks for ink-jet printing, and an ink for ink-jet printing.
  • the present invention relates to colored composite microparticles having a fine primary particle diameter, and exhibiting a high tinting strength, an excellent dispersibility and an excellent light fastness; a dispersion containing the colored composite microparticles which exhibits an excellent dispersibility; a process for producing the colored composite microparticles; a colorant for color filters, which has a fine primary particle diameter, exhibits a high tinting strength, and is excellent in dispersibility in vehicles, light fastness and heat resistance; a coloring composition for color filters and a color filter which are excellent in light fastness and heat resistance as well as transparency; a colorant for inks for ink-jet printing, which has a fine primary particle diameter and a uniform particle size distribution, exhibits a high tinting strength, and is excellent in dispersibility and light fastness; and an ink for ink-jet printing, which contains the colorant for inks for ink-jet printing, and is excellent in dispersibility, dispersion stability and light fastness.
  • Organic pigments have been extensively used as colorants in various applications such as paints, resins, printing inks, inks for ink-jet printing, toners and color filters.
  • the pigments have been required to have a high tinting strength. For this reason, it has been required to provide much finer pigments.
  • the organic pigments are, in general, present in the form of fine primary particles having a particle size of about 20 nm to 100 nm, which are formed from pigments in a molecular state obtained by chemical reaction, etc.
  • the organic pigments in the form of fine primary particles tend to be agglomerated together because of a very high surface energy on the particles.
  • the organic pigments are usually present in the form of secondary particles having a very large particle size and a high cohesive force. Therefore, it has been required to develop techniques for obtaining very finely divided organic pigments.
  • a wet-pulverization method such as typically a solvent/salt milling method in which pigment particles are mechanically pulverized together with a high-viscous water-soluble organic solvent such as polyethyleneglycol using an abrasive such as a common salt, a dry-pulverization method of pulverizing the pigment particles under a dried condition using a pulverizer such as a ball mill, an attritor and a vibration mill, and a method of forming fine pigment particles by solubilizing pigments to prepare a solution thereof and then precipitating the pigments from the solution under specific conditions.
  • a wet-pulverization method such as typically a solvent/salt milling method in which pigment particles are mechanically pulverized together with a high-viscous water-soluble organic solvent such as polyethyleneglycol using an abrasive such as a common salt
  • a dry-pulverization method of pulverizing the pigment particles under a dried condition using a pulverizer such as a ball mill
  • the finer the particle size of the pigments the stronger the coagulation force between the pigments particles.
  • the coagulation between the particles after drying becomes remarkable, so that it may be extremely difficult to maintain a shape of the primary particles.
  • the pigment particles are present in the form of secondary agglomerated particles as an aggregate having a very strong coagulation force, so that it may be further difficult to disperse the pigment particles in a solvent.
  • color filters have been extensively used in the application fields of monitors for televisions, personal computers, portable telephones, etc., or in the application fields of CCD and CMOS for digital cameras.
  • the color filters of a pigment-dispersion type are predominately used from the standpoints of a light fastness and a heat resistance.
  • the color filters have been required to exhibit a still higher pixel reproducibility as well as a high contrast.
  • organic pigments used in the color filters are provided in the form of fine particles which can be stably dispersed in a nano level.
  • the color filters are required to show a good light fastness for preventing the color fading thereof even when irradiated with a backlight, and further required to have a good heat resistance for heat-treating the filters at a temperature of about 250° C. upon hardening of patterns formed thereon or vapor deposition of ITO film thereon.
  • the pigments in the form of very fine particles generally tend to be deteriorated in light fastness and heat resistance. For this reason, it has been strongly required to provide a colorant for color filters, which has a particle size in a nano level, can be stably dispersed in vehicles, and is excellent in light fastness and heat resistance.
  • the resultant printed images have a high image density and an excellent light fastness as compared to those obtained by using the dyes as the colorant.
  • the inks for ink-jet printing generally contain water in an amount of 80% by weight of whole constituting components thereof, the pigments, in particular, organic pigments composed of organic compounds, tend to be hardly dispersed therein.
  • the pigments tend to be insoluble in a solvent such as water unlike the dyes.
  • the organic pigments in a molecular state which are obtained by chemical reactions, etc., and the organic pigments composed of fine primary particles having a particle size of about 20 nm to 100 nm, tend to be agglomerated together because of a very high surface energy on the particles, so that it may be difficult to obtain particles having a uniform particle size distribution, thereby failing to produce a clear image without fogging.
  • the clogging of the head portion may be prevented by finely reducing a particle size of the colorant.
  • colorant in the form of fine particles having an excellent transparency there have been proposed colored fine particles which are produced by completely dissolving and removing core particles from composite particles obtained by allowing an organic pigment to adhere onto the surface of white inorganic particles as the core particles through a gluing agent such as an alkoxysilane, by using a theoretical amount or more of an acid or an alkali capable of dissolving a whole amount of the white inorganic particles as the core particles (Japanese Patent Application Laid-open (KOKAI) No. 2003-246941).
  • a gluing agent such as an alkoxysilane
  • a colorant for inks for ink-jet printing which is composed of composite particles having an average particle diameter of 0.001 to 0.15 ⁇ m which are obtained by uniformly adhering an organic pigment onto the surface of extender pigment particles through a gluing agent (Japanese Patent Application Laid-open (KOKAI) Nos. 2003-55591, 2003-268278, 2003-327880 and 2006-111875).
  • the resultant colored fine particles tend to have a ⁇ potential close to zero, and therefore, hardly exhibit a good electrostatic repulsion effect in vehicles, so that it may be difficult to attain a good dispersibility and a good dispersion stability thereof in vehicles.
  • the transparent coloring composition as described in Japanese Patent Application Laid-open (KOKAI) No. 2004-307853 in which an organic and inorganic composite pigment having an average particle diameter of 1 to 100 nm which is composed of primary particles obtained by adhering an organic pigment onto the surface of white inorganic particles directly or through a surface modifying agent, is dispersed in a solvent, as described in Comparative Examples below, since the obtained composition is a transparent coloring composition containing the organic and inorganic composite pigment obtained using the white inorganic particles such as silica particles as core particles, it may be difficult to obtain such a coloring composition for color filters having a high tinting strength identical to or higher than that of the raw organic pigment adhered thereto.
  • a transparent coloring composition as described in Japanese Patent Application Laid-open (KOKAI) No. 2004-307853 in which an organic and inorganic composite pigment having an average particle diameter of 1 to 100 nm which is composed of primary particles obtained by adhering an organic pigment onto the surface of white inorganic particles directly or through a surface
  • An object of the present invention is to provide colored composite microparticles having a fine primary particle diameter and exhibiting a high tinting strength, an excellent dispersibility and an excellent light fastness, a process for producing the colored composite microparticles and a dispersion prepared by dispersing the colored composite microparticles in a solvent.
  • a further object of the present invention is to provide a colorant for color filters which has a fine primary particle diameter, exhibits a high tinting strength, and is excellent in light fastness, heat resistance and dispersibility in vehicles, as well as a coloring composition for color filters and a color filter.
  • a still further object of the present invention is to provide a colorant for inks for ink-jet printing which has a fine primary particle diameter and a uniform particle size distribution, and exhibits a high tinting strength and an excellent light fastness, as well as an ink for ink-jet printing.
  • the above problems can be solved by eluting out a part of silica particle and at least a part of a surface modifying agent, which are contained in composite particles obtained by coating the surface of the silica particles with an organic pigment through the surface modifying agent.
  • the present invention suitable for organic pigments provides the following three aspects 1 to 3.
  • colored composite microparticles comprising silica and an organic pigment, wherein the silica is enclosed in the organic pigment and contained in an amount of 0.001 to 9% by weight, calculated as Si, based on a weight of the colored composite microparticles.
  • the colored composite microparticles as defined in the first aspect which comprise silica and an organic pigment wherein the silica is enclosed in the organic pigment and contained in an amount of 0.001 to 9% by weight, calculated as Si, based on a weight of the colored composite microparticles.
  • the present invention suitable for colorants for color filters as well as color filters provides the following seven aspects 4 to 10.
  • a colorant for color filters which comprises colored composite microparticles comprising silica and an organic pigment wherein the silica is enclosed in the organic pigment and contained in an amount of 0.001 to 9% by weight, calculated as Si, based on a weight of the colored composite microparticles.
  • a coloring composition (a) for color filters produced by dispersing in a solvent the colorant for color filters as defined in the fourth aspect which comprises colored composite microparticles comprising silica and an organic pigment wherein the silica is enclosed in the organic pigment and contained in an amount of 0.001 to 9% by weight, calculated as Si, based on a weight of the colored composite microparticles.
  • a coloring composition (b) for color filters produced by dispersing the coloring composition (a) for color filters as defined in the fifth aspect which is obtained by dispersing in a solvent, the colorant for color filters which comprises colored composite microparticles comprising silica and an organic pigment wherein the silica is enclosed in the organic pigment and contained in an amount of 0.001 to 9% by weight, calculated as Si, based on a weight of the colored composite microparticles, in a solution of a transparent resin containing an acid group and/or a latent acid group.
  • a coloring composition (C) for color filters comprising the coloring composition (b) for color filters as defined in the sixth aspect which composition (b) is produced by dispersing the coloring composition (a) for color filters which is obtained by dispersing in a solvent, the colorant for color filters which comprises colored composite microparticles comprising silica and an organic pigment wherein the silica is enclosed in the organic pigment and contained in an amount of 0.001 to 9% by weight, calculated as Si, based on a weight of the colored composite microparticles, in a solution of a transparent resin containing an acid group and/or a latent acid group; a polyfunctional monomer containing two or more ethylenically unsaturated double bonds; and a photo-radical polymerization initiator.
  • a coloring composition (D) for color filters comprising the coloring composition (b) for color filters as defined in the sixth aspect which composition (b) is produced by dispersing the coloring composition (a) for color filters which is obtained by dispersing in a solvent, the colorant for color filters which comprises colored composite microparticles comprising silica and an organic pigment wherein the silica is enclosed in the organic pigment and contained in an amount of 0.001 to 9% by weight, calculated as Si, based on a weight of the colored composite microparticles, in a solution of a transparent resin containing an acid group and/or a latent acid group; and a photo-acid generator.
  • a color filter comprising a film-shaped product formed from the coloring composition (b) for color filters as defined in the sixth aspect which composition (b) is produced by dispersing the coloring composition (a) for color filters which is obtained by dispersing in a solvent, the colorant for color filters which comprises colored composite microparticles comprising silica and an organic pigment wherein the silica is enclosed in the organic pigment and contained in an amount of 0.001 to 9% by weight, calculated as Si, based on a weight of the colored composite microparticles, in a solution of a transparent resin containing an acid group and/or a latent acid group.
  • a color filter comprising a film-shaped product formed from the coloring composition (C) for color filters as defined in the seventh aspect or the coloring composition (D) for color filters as defined in the eighth aspect.
  • the present invention suitable for colorants for inks for ink-jet printing as well as inks for ink-jet printing provides the following two aspects 11 and 12.
  • a colorant for inks for ink-jet printing comprising colored composite microparticles comprising silica and an organic pigment wherein the silica is enclosed in the organic pigment and contained in an amount of 0.001 to 9% by weight, calculated as Si, based on a weight of the colored composite microparticles.
  • an ink for ink-jet printing comprising the colorant for inks for ink-jet printing as defined in the eleventh aspect which comprises colored composite microparticles comprising silica and an organic pigment wherein the silica is enclosed in the organic pigment and contained in an amount of 0.001 to 9% by weight, calculated as Si, based on a weight of the colored composite microparticles.
  • the colored composite microparticles according to the first aspect of the present invention are in the form of composite particles comprising silica and an organic pigment wherein the silica is enclosed in the organic pigment, and the content of the silica is 0.001 to 9% by weight (calculated as Si) based on the weight of the composite particles.
  • the content of the silica in the colored composite microparticles is usually 0.001 to 9% by weight, preferably 0.005 to 7.0% by weight and more preferably 0.01 to 5.0% by weight (calculated as Si) based on the weight of the colored composite microparticles.
  • the content of the silica is less than 0.001% by weight (calculated as Si) based on a weight of the colored composite microparticles, since the amount of the silica enclosed in the colored composite microparticles is too small, the ⁇ potential of the colored composite microparticles tends to be substantially zero, thereby failing to attain a good electrostatic repulsion effect thereof. As a result, the obtained composite particles tend to be deteriorated in dispersibility in vehicles.
  • the obtained composite particles may fail to exhibit sufficient light fastness and heat resistance.
  • the content of the silica in the colored composite microparticles is more than 9.0% by weight, since the amount of the silica enclosed in the colored composite microparticles is too large, it may be difficult to obtain colored composite microparticles exhibiting a sufficient tinting strength.
  • organic pigment there may be used various alkali-resisting organic pigments usable as colorants for paints, resins, printing inks, inks for ink-jet printing, toners, color filters, etc., such as organic red-based pigments, organic blue-based pigments, organic yellow-based pigments, organic green-based pigments, organic orange-based pigments, organic brown-based pigments, organic violet-based pigments and organic black-based pigments.
  • organic red-based pigments may include azo-based pigments such as brilliant carmine, permanent red and condensed azo red; condensed polycyclic-based pigments such as diaminoanthraquinolyl red, quinacridone red, thioindigo red, perylene red, perinone red and diketopyrrolopyrrole red; or the like.
  • organic blue-based pigments may include phthalocyanine-based pigments such as metal-free phthalocyanine blue, phthalocyanine blue and fast sky blue; condensed polycyclic-based pigments such as indanthron blue and indigo blue; or the like.
  • organic yellow-based pigments may include azo-based pigments such as Hanza yellow, benzidine yellow, permanent yellow and condensed azo yellow; condensed polycyclic-based pigments such as isoindolinone yellow, anthrapyrimidine yellow and quinophthalone yellow; or the like.
  • organic green-based pigments may include phthalocyanine-based pigments such as phthalocyanine green; or the like.
  • organic orange-based pigments may include azo-based pigments such as permanent orange, lithol fast orange, pyrazolone orange and vulcan fast orange; condensed polycyclic-based pigments such as quinacridone, perylene orange and diketopyrrolopyrrole orange; or the like.
  • organic brown-based pigments may include azo-based pigments such as permanent brown, para-brown and benzoimidazolone brown; condensed polycyclic-based pigments such as thioindigo brown; or the like.
  • organic violet-based pigments may include azo-based pigments such as fast violet; condensed polycyclic-based pigments such as unsubstituted quinacridone, dioxazine violet and perylene violet; or the like.
  • organic black-based pigments may include condensed polycyclic-based pigments such as perylene black; aniline black; or the like.
  • the colored composite microparticles of the present invention have an average primary particle diameter of usually 1 to 50 nm, preferably 1 to 40 nm and more preferably 1 to 30 nm.
  • the colored composite microparticles of the present invention have a number-average particle diameter of usually not more than 200 nm, preferably 1 to 150 nm, more preferably 1 to 100 nm and still more preferably 1 to 50 nm.
  • the number-average particle diameter of the colored composite microparticles is more than 200 nm, the resultant particles tend to be deteriorated in optical properties because of too large particle size thereof, thereby failing to achieve the objects of the present invention.
  • the colored composite microparticles of the present invention have a volume-average particle diameter of usually not more than 200 nm, preferably 1 to 150 nm and more preferably 1 to 100 nm.
  • the volume-average particle diameter of the colored composite microparticles is more than 200 nm, the resultant particles tend to be deteriorated in optical properties because of too large particle size thereof, thereby failing to achieve the objects of the present invention.
  • the colored composite microparticles of the present invention have a BET specific surface area value of usually 20 to 500 m 2 /g, preferably 25 to 400 m 2 /g and more preferably 30 to 300 m 2 /g.
  • the colored composite microparticles of the present invention have a tinting strength of usually not less than 102%, preferably not less than 103% and more preferably not less than 104% as measured by the below-mentioned evaluation method.
  • the ⁇ potential of the colored composite microparticles of the present invention when measured in an aqueous system is usually not more than ⁇ 5 mV, preferably not more than ⁇ 8 mV and more preferably not more than ⁇ 10 mV.
  • ⁇ potential of the colored composite microparticles as measured in an aqueous system is more than ⁇ 5 mV and close to zero, it may be difficult to attain a good electrostatic repulsion effect thereof, thereby failing to show a good dispersibility and a good dispersion stability.
  • the ⁇ potential of the colored composite microparticles of the present invention when measured in a solvent system is usually not more than ⁇ 2 mV, preferably not more than ⁇ 3 mV and more preferably not more than ⁇ 5 mV.
  • ⁇ potential of the colored composite microparticles as measured in a solvent system is more than ⁇ 2 mV and close to zero, it may be difficult to attain a good electrostatic repulsion effect thereof, thereby failing to show a good dispersibility.
  • the surface modifying agent may still remain on the surface of the silica particles enclosed in the colored composite microparticles.
  • the dispersion according to the second aspect of the present invention is formed by dispersing in a solvent, the colored composite microparticles as defined in the first aspect which comprise silica and an organic pigment wherein the silica is enclosed in the organic pigment and contained in an amount of 0.001 to 9% by weight, calculated as Si, based on the weight of the colored composite microparticles.
  • the amount of the colored composite microparticles contained in the dispersion is usually 3 to 300 parts by weight, preferably 4 to 150 parts by weight, more preferably 5 to 100 parts by weight, still more preferably 5 to 75 parts by weight and most preferably 5 to 50 parts by weight based on 100 parts by weight of a dispersion base material.
  • the dispersion base material comprises water and/or a water-soluble organic solvent, or an organic solvent, and may also contain, if required, resins, a defoaming agent, an extender pigment, a drying accelerator, a surfactant, a hardening accelerator, other assistants, etc.
  • the amounts of the resins, defoaming agent, extender pigment, drying accelerator, surfactant, hardening accelerator, other assistants, etc., contained in the dispersion base material may be appropriately determined depending upon use and applications of the dispersion, and are usually not more than 95% by weight.
  • Examples of the solvent used in a water-based dispersion may include mixed solvents of water and a water-soluble solvent ordinarily used for water-based paints, etc.
  • Specific examples of the water-soluble solvent may include alcohol-based solvents such as ethyl alcohol, propyl alcohol and butyl alcohol; glycol ether-based solvents such as methyl cellosolve, ethyl cellosolve, propyl cellosolve and butyl cellosolve; oxyethylene or oxypropylene addition polymers such as diethyleneglycol, triethyleneglycol, polyethyleneglycol, dipropyleneglycol, tripropyleneglycol and polypropyleneglycol; alkyleneglycols such as ethyleneglycol, propyleneglycol and 1,2,6-hexanetriol; glycerol; 2-pyrrolidone; or the like.
  • Examples of the solvent used in a solvent-based dispersion may include aromatic hydrocarbons such as toluene and xylene; ketones such as methyl ethyl ketone and cyclohexanone; amides such as N,N-dimethylformamide, N,N-dimethylacetamide and N-methylpyrrolidone; ether alcohols such as ethyleneglycol monomethyl ether, ethyleneglycol monoethyl ether, diethyleneglycol monomethyl ether, propyleneglycol monomethyl ether and propyleneglycol monoethyl ether; ether acetates such as ethyleneglycol monomethyl ether acetate, ethyleneglycol monoethyl ether acetate, propyleneglycol monomethyl ether acetate and propyleneglycol monoethyl ether acetate; acetic acid esters such as ethyl acetate, butyl acetate and isobutyl a
  • the resultant dispersion can exhibit a good electrostatic repulsion effect.
  • organic solvents having a high polarity such as typically alcohols, ether alcohols and ether acetates
  • the resultant dispersion can exhibit a good electrostatic repulsion effect.
  • These solvents may be used in the form of a mixture of any two or more thereof.
  • the dispersion of the present invention have a number-average dispersed particle diameter of usually 1 to 200 nm, preferably 1 to 150 nm, more preferably 1 to 100 nm and still more preferably 1 to 50 nm.
  • the number-average dispersed particle diameter of the dispersion is more than 200 nm, it may be difficult to achieve the objects of the present invention owing to a too large particle size of the particles dispersed therein.
  • the dispersion of the present invention have a volume-average dispersed particle diameter of usually 1 to 200 nm, preferably 1 to 150 nm and more preferably 1 to 100 nm.
  • a volume-average dispersed particle diameter of the dispersion is more than 200 nm, it may be difficult to achieve the objects of the present invention owing to a too large particle size of the particles dispersed therein.
  • the degree of precipitation is usually Rank 3, 4 or 5 and preferably Rank 4 or 5.
  • a rate of change (percentage of change) in viscosity of the dispersion is usually not more than 20% and preferably not more than 10%.
  • the specific absorption coefficient ⁇ w (on the weight basis) representing a tinting strength of the dispersion of the present invention is usually not less than 1.20, preferably 1.40 to 5.00 and more preferably 1.50 to 5.00 as measured by the below-mentioned evaluation method.
  • the process or producing the colored composite microparticles according to the third aspect of the present invention includes the steps of (1) adding a surface modifying agent to silica particles; (2) mixing the surface modifying agent and the silica particles under stirring to coat the surface of the silica particles with the surface modifying agent; (3) then adding an organic pigment to the silica particles coated with the surface modifying agent; (4) mixing the organic pigment and the coated silica particles under stirring to adhere the organic pigment onto the surface of the coated silica particles, thereby obtaining composite particles; and (5) dissolving out a part of the silica particles and at least a part of the surface modifying agent which are contained in the resultant composite particles, with an alkali solution.
  • silica particles, the surface modifying agent and the organic pigment used in the present invention are explained.
  • the silica particles used in the present invention have an average primary particle diameter of usually 1 to 100 nm, preferably 1 to 50 nm and more preferably 1 to 30 nm.
  • the silica particles used in the present invention have a BET specific surface area value of usually 10 to 1000 m 2 /g and preferably 15 to 500 m 2 /g.
  • the surface modifying agent used in the present invention is not particularly limited as long as the organic pigment can be adhered onto the surface of the silica particles through the surface modifying agent.
  • the surface modifying agent may include organosilicon compounds such as alkoxysilanes, silane-based coupling agents and organopolysiloxanes; coupling agents such as titanate-based coupling agents, aluminate-based coupling agents and zirconium-based coupling agents; low-molecular weight or high-molecular weight surfactants; or the like.
  • organosilicon compounds such as alkoxysilanes, silane-based coupling agents and organopolysiloxanes.
  • organosilicon compounds may include alkoxysilanes such as methyltriethoxysilane, dimethyldiethoxysilane, phenyltriethoxysilane, diphenyldiethoxysilane, methyltrimethoxysilane, dimethyldimethoxysilane, phenyltrimethoxysilane, diphenyldimethoxysilane, ethyltriethoxysilane, propyltriethoxysilane, butyltriethoxysilane, isobutyltrimethoxysilane, hexyltriethoxysilane, octyltriethoxysilane and decyltriethoxysilane; silane-based coupling agents such as vinyltrimethoxysilane, vinyltriethoxysilane, ⁇ -aminopropyltriethoxysilane, ⁇ -glycidoxypropyltriethoxysilane,
  • titanate-based coupling agents may include isopropyltristearoyl titanate, isopropyltris(dioctylpyrophosphate)titanate, isopropyltri(N-aminoethyl-aminoethyl)titanate, tetraoctylbis(ditridecylphosphate)titanate, tetra(2,2-diallyloxymethyl-1-butyl)bis(ditridecyl)phosphate titanate, bis(dioctylpyrophosphate)oxyacetate titanate, bis(dioctylpyrophosphate)ethylene titanate, or the like.
  • aluminate-based coupling agents may include acetoalkoxyaluminum diisopropylate, aluminum diisopropoxymonoethylacetoacetate, aluminum trisethylacetoacetate, aluminum trisacetylacetonate or the like.
  • zirconate-based coupling agents may include zirconium tetrakisacetylacetonate, zirconium dibutoxybisacetylacetonate, zirconium tetrakisethylacetoacetate, zirconium tributoxymonoethylacetoacetate, zirconium tributoxyacecylacetonate, or the like.
  • low-molecular weight surfactants may include alkylbenzenesulfonic acid salts, dioctylsulfonesuccinic acid salts, alkylamineacetic acid salts, alkyl fatty acid salts or the like.
  • high-molecular weight surfactants may include polyvinyl alcohol, polyacrylic acid salts, carboxymethyl cellulose, acrylic acid-maleic acid salt copolymers, olefin-maleic acid salt copolymers or the like.
  • the surface modifying agent is coated in an amount of usually 0.05 to 15.0% by weight, preferably 0.1 to 12.0% by weight and more preferably 0.15 to 10.0% by weight (calculated as C) based on the weight of the silica particles as core particles.
  • the coating amount of the surface modifying agent lies within 0.05 to 15.0% by weight, the organic pigment can be adhered onto the surface of the silica particles in an amount of usually 10 to 500 parts by weight based on 100 parts by weight of the silica particles.
  • organic pigment to be adhered there may be used various organic pigments such as the organic red-based pigments, the organic blue-based pigments, the organic yellow-based pigments, the organic green-based pigments, the organic orange-based pigments, the organic brown-based pigments, the organic violet-based pigments and the organic black-based pigments as described previously.
  • the organic pigments having a low alkali resistance such as alkali blue and isoindoline-based organic pigments, because if these organic pigments are contained in the composite particles, the pigments tend to be dissolved out therefrom when subjecting the composite particles to the below-mentioned treatment for dissolving the silica particles with an alkali.
  • the amount of the organic pigment added is usually 10 to 500 parts by weight, preferably 30 to 400 parts by weight and more preferably 50 to 300 parts by weight based on 100 parts by weight of the silica particles as core particles.
  • the composite particles used in the present invention can be produced, as described above, by (1) adding the surface modifying agent to the silica particles; (2) mixing the surface modifying agent and the silica particles under stirring to coat the surface of the silica particles with the surface modifying agent; (3) adding the organic pigment to the obtained silica particles coated with the surface modifying agent; and (4) mixing the organic pigment and the coated silica particles under stirring to adhere the organic pigment onto the surface of the silica particles coated with the surface modifying agent. Meanwhile, a substantially whole amount of the surface modifying agent added can be coated onto the surface of the silica particles.
  • the mixing and stirring of the silica particles and the surface modifying agent, or the mixing and stirring of the organic pigment and the silica particles whose surface is coated with the surface modifying agent, may be preferably carried out using an apparatus capable of applying a shear force to the particles, especially such an apparatus capable of simultaneously effecting shear action, spatula stroking and compression.
  • the apparatus may include wheel-type kneaders, ball-type kneaders, blade-type kneaders, roll-type kneaders or the like. Among these apparatuses, the wheel-type kneaders are preferred to effectively practice the present invention.
  • wheel-type kneaders may include edge runners (similar in meaning to mix muller, Simpson mill and sand mill), multimill, Stotz mill, wet pan mill, corner mill, ring muller or the like.
  • the preferred kneaders are edge runners, multimill, Stotz mill, wet pan mill and ring muller, and the more preferred kneaders are edge runners.
  • Specific examples of the ball-type kneaders may include vibration mill or the like.
  • blade-type kneaders may include Henschel mixer, planetary mixer, Nauter mixer or the like.
  • Specific examples of the roll-type kneaders may include extruders or the like.
  • the conditions of mixing and stirring of the silica particles and the surface modifying agent may be selected so as to uniformly coat the surface of the silica particles with the surface modifying agent.
  • the mixing and stirring conditions may be appropriately controlled such that the linear load is usually 19.6 to 1,960 N/cm (2 to 200 kg/cm), preferably 98 to 1,470 N/cm (10 to 150 kg/cm), more preferably 147 to 980 N/cm (15 to 100 kg/cm); the treating time is usually 5 min to 24 hr, preferably 10 min to 20 hr; and the stirring speed is usually 2 to 2,000 rpm, preferably 5 to 1,000 rpm and more preferably 10 to 800 rpm.
  • the organic pigment may be added slowly and little by little for a period of usually about 5 min to 24 hr and preferably about 5 min to 20 hr. Alternatively, 5 to 25 parts by weight of the organic pigment may be added several times to 100 parts by weight of the silica particles until the amount of the organic pigment added reaches the desired amount.
  • the conditions of mixing and stirring of the silica particles whose surface is coated with the surface modifying agent, and the organic pigment may be appropriately selected so as to uniformly adhere the organic pigment on the coated silica particles.
  • the mixing and stirring may be controlled such that the linear load is usually 19.6 to 1,960 N/cm (2 to 200 kg/cm), preferably 98 to 1,470 N/cm (10 to 150 kg/cm) and more preferably 147 to 980 N/cm (15 to 100 kg/cm); the treating time is usually 5 min to 24 hr and preferably 10 min to 20 hr; and the stirring speed is usually 2 to 2,000 rpm, preferably 5 to 1,000 rpm and more preferably 10 to 800 rpm.
  • the resultant particles may be subjected to drying or heating treatment, if required.
  • the heating temperature used in the drying or heating treatment is usually 40 to 150° C. and preferably 60 to 120° C.
  • the heating time is usually 10 min to 12 hr and preferably 30 min to 3 hr.
  • the thus obtained composite particles have an average primary particle diameter of usually 1 to 100 nm, preferably 1 to 50 nm and more preferably 1 to 30 nm.
  • the composite particles have a BET specific surface area value of usually 10 to 500 m 2 /g, preferably 15 to 400 m 2 /g and more preferably 20 to 300 m 2 /g.
  • the colored composite microparticles of the present invention can be produced by (5) treating the above composite particles with an alkali solution to dissolve out a part of the silica particles and at least a part of the surface modifying agent from the composite particles, so as to allow a part of the silica component or a part of the silica component and the surface modifying agent to remain in the composite particles.
  • the concentration of the composite particles contained in the dissolution solution to be subjected to the dissolution treatment is usually 1.0 to 30.0 parts by weight, preferably 2.5 to 25.0 parts by weight and more preferably 5.0 to 20.0 parts by weight based on 100 mL of water.
  • the amount of the alkali contained in the treating solution to be subjected to the dissolution treatment is usually 0.01 to 0.95 time, preferably 0.02 to 0.90 time and more preferably 0.05 to 0.85 time the amount of alkali required to dissolve whole amounts of the silica particles and the surface modifying agent.
  • the amount of the alkali contained in the treating solution is more than 0.95 time, the silica particles and the surface modifying agent tend to be completely dissolved from the composite particles, thereby failing to obtain the colored composite microparticles as aimed by the present invention.
  • the amount of the alkali contained in the treating solution is less than 0.01 time, it tends to take a very long time until the silica particles or both the silica particles and the surface modifying agent are dissolved out such that the content thereof in the colored composite microparticles reaches 9% by weight or less, resulting in industrially disadvantageous process.
  • the pH value of the treating solution to be subjected to the dissolution treatment is usually 10.0 to 13.8, preferably 11.0 to 13.6 and more preferably 11.5 to 13.4.
  • the pH value of the treating solution is more than 13.8, the organic pigment tends to be considerably damaged by the alkali, so that it may be difficult to obtain the colored composite microparticles having a good light fastness and a good heat resistance.
  • the pH value of the treating solution is less than 10.0, it tends to take a very long time until the silica particles or both the silica particles and the surface modifying agent are dissolved out such that the content thereof in the colored composite microparticles reaches 9% by weight or less, resulting in industrially disadvantageous process.
  • the dissolution treatment temperature is usually 40 to 100° C., preferably 45 to 90° C. and more preferably 50 to 80° C.
  • the dissolution treatment temperature is less than 40° C.
  • the dissolution treatment tends to require a prolonged time such as more than 50 hr, resulting in industrially disadvantageous process.
  • the dissolution treatment temperature is more than 100° C., it may be difficult to obtain the colored composite microparticles having a good light fastness and a good heat resistance because of severe damage to the organic pigment, and the use of a special apparatus such as an autoclave tends to be required, resulting in industrially disadvantageous process.
  • the dissolution treatment time is usually 5 min to 50 hr, preferably 10 min to 30 hr and more preferably 20 min to 10 hr.
  • the dissolution treatment time as long as more than 50 hr tends to result in industrially disadvantageous process.
  • a solid component is separated from the dissolution solution by filtration, and then subjected to washing and then ordinary drying or freeze-drying, thereby obtaining the colored composite microparticles.
  • the thus obtained colored composite microparticles of the present invention can be readily dispersed owing to a good electrostatic repulsion effect of the silica or both the silica and the surface modifying agent contained therein even when merely dried by an ordinary drying method.
  • the water-based dispersion of the present invention may be produced by re-dispersing the thus obtained composite microparticles in water or a mixture of water and a water-soluble organic solvent, or by subjecting the composite particles to dissolution treatment, separating a solid component from the dissolution solution by filtration, washing the thus separated solid component with water, and then dispersing the solid component recovered without drying in water or the water-soluble organic solvent.
  • Additives such as resins, a dispersant, a defoaming agent and a surfactant may be added to the dispersion, if required.
  • the solvent-based dispersion of the present invention may be produced by re-dispersing the above obtained composite microparticles in an organic solvent or an oil vehicle, or by subjecting the composite particles to dissolution treatment, separating a solid component from the dissolution solution by filtration, washing the thus separated solid component with water, flashing the solid component with an organic solvent or an oil vehicle, and then dispersing the thus treated solid component in the organic solvent or the oil vehicle.
  • Additives such as resins, a dispersant, a defoaming agent, an extender pigment, a drying accelerator, a surfactant, an hardening accelerator and other assistants may be added to the dispersion, if required.
  • the mixing and dispersing of the colored composite microparticles and the solvent may be conducted using a ball mill, a beads mill, a sand mill, an edge runner, an ultrasonic dispersing apparatus, a twin or triple roll mill, an extruder, a high-speed impact mill, or the like.
  • a grinding medium for grinding-type mills such as the ball mill and beads mill, there may be used steel beads, glass beads, ceramic beads, etc., according to the kind of material of the mill used.
  • the size of the grinding medium is usually 0.01 to 10 mm and preferably 0.03 to 3 mm.
  • the grinding temperature is not particularly limited, and may be controlled, for example, to the range of from room temperature to a boiling point of the solvent used.
  • the colorant for color filters according to the fourth aspect of the present invention comprises colored composite microparticles comprising silica and an organic pigment wherein the silica is enclosed in the organic pigment and contained in an amount of 0.001 to 9% by weight, calculated as Si, based on the weight of the colored composite microparticles.
  • the ⁇ E* value thereof is usually not more than 5.0, preferably not more than 4.5 and more preferably not more than 4.0 as measured by the below-mentioned evaluation method.
  • the colorant for color filters according to the present invention has the substantially same silica content, average primary particle diameter, number-average particle diameter, volume-average particle diameter, BET specific surface area value, tinting strength, light fastness, ⁇ potential in a water-based system and ⁇ potential in a solvent-based system as those of the colored composite microparticles according to the first aspect of the present invention.
  • the coloring composition (a) for color filters according to the fifth aspect of the present invention comprises the colorant for color filters which comprises colored composite microparticles comprising silica and an organic pigment wherein the silica is enclosed in the organic pigment and contained in an amount of 0.001 to 9% by weight, calculated as Si, based on the weight of the colored composite microparticles, and a coloring composition base material.
  • the coloring composition base material comprises a solvent and may also optionally contain additives such as a dispersant, a pigment derivative, a defoaming agent and a surfactant according to the requirements.
  • the content of the colorant for color filters in the coloring composition for color filters is usually 3 to 300 parts by weight, preferably 4 to 200 parts by weight and more preferably 5 to 150 parts by weight based on 100 parts by weight of the coloring composition base material.
  • the content of the additives in the coloring composition base material is usually not more than 60% by weight.
  • any solvent may be appropriately used in the coloring composition of the present invention as long as it is capable of suitably dissolving or dispersing the colorant for color filters, the transparent resin, the polyfunctional monomer containing two or more ethylenically unsaturated double bonds, the photo-polymerization initiator and the photo-acid generator therein, and being volatilized and removed from the composition after coating.
  • the solvent may include water; aromatic hydrocarbons such as toluene and xylene; ketones such as methyl ethyl ketone and cyclohexanone; amides such as N,N-dimethylformamide, N,N-dimethylacetamide and N-methyl pyrrolidone; ether alcohols such as ethyleneglycol monomethyl ether, ethyleneglycol monoethyl ether, diethyleneglycol monomethyl ether, propyleneglycol monomethyl ether and propyleneglycol monoethyl ether; ether acetates such as ethyleneglycol monomethyl ether acetate, ethyleneglycol monoethyl ether acetate, propyleneglycol monomethyl ether acetate and propyleneglycol monoethyl ether acetate; acetic acid esters such as ethyl acetate, butyl acetate and isobutyl acetate; lactic acid esters such as
  • Examples of the dispersant usable in the present invention may include anionic surfactants such as ammonium laurylsulfate and polyoxyethylene alkylethersulfates; cationic surfactants such as stearylamine acetate and lauryltrimethyl ammonium chloride; amphoteric surfactants such as lauryldimethylamine oxide and laurylcarboxymethylhydroxyethyl imidazolium betaine; nonionic surfactants such as polyoxyethylene lauryl ether, polyoxyethylene stearyl ether and sorbitan monostearate; or the like. These dispersants may be used in the form of a mixture of any two or more thereof.
  • the preferred dispersants are anionic surfactants, nonionic surfactants, cationic surfactants, sodium naphthalenesulfonate formalin condensates and acetylene glycol-based dispersants.
  • the number-average dispersed particle diameter of the coloring composition (a) for color filters is usually 1 to 200 nm, preferably 1 to 150 nm, more preferably 1 to 100 nm and still more preferably 1 to 50 nm.
  • the resultant composition tends to be deteriorated in optical properties owing to a too large particle size of the particles dispersed therein, thereby failing to achieve the objects of the present invention.
  • the volume-average dispersed particle diameter of the coloring composition (a) for color filters is usually 1 to 200 nm, preferably 1 to 150 nm and more preferably 1 to 100 nm.
  • the resultant composition tends to be deteriorated in optical properties owing to a too large particle size of the particles dispersed therein, thereby failing to achieve the objects of the present invention.
  • the rate of change in viscosity thereof is usually not more than 20% and preferably not more than 10% as measured by the below-mentioned evaluation method.
  • the rate of change in viscosity of the coloring composition is more than 20%, the resultant composition may fail to maintain a good dispersibility under a stable dispersing condition for a long period of time.
  • the light transmittance at 530 nm of the coloring composition (a) is usually not less than 65%, preferably not less than 70% and more preferably not less than 75%.
  • the specific absorption coefficient at 650 nm (on the weight basis) of the coloring composition (a) is usually 1.05 to 5.00, preferably 1.10 to 5.00 and more preferably 1.20 to 5.00 as measured by the below-mentioned evaluation method.
  • the light transmittance at 460 nm of the coloring composition (a) is usually not less than 65%, preferably not less than 70% and more preferably not less than 75%.
  • the specific absorption coefficient at 610 nm (on the weight basis) of the coloring composition (a) is usually 1.05 to 5.00, preferably 1.10 to 5.00 and more preferably 1.20 to 5.00 as measured by the below-mentioned evaluation method.
  • the light transmittance at 620 nm of the coloring composition (a) is usually not less than 65%, preferably not less than 70% and more preferably not less than 75%.
  • the specific absorption coefficient at 550 nm (on the weight basis) of the coloring composition (a) is usually 1.05 to 5.00, preferably 1.10 to 5.00 and more preferably 1.20 to 5.00 as measured by the below-mentioned evaluation method.
  • the light transmittance at 550 nm of the coloring composition (a) is usually not less than 65%, preferably not less than 70% and more preferably not less than 75%.
  • the specific absorption coefficient at 400 nm (on the weight basis) of the coloring composition (a) is usually 1.05 to 5.00, preferably 1.10 to 5.00 and more preferably 1.20 to 5.00 as measured by the below-mentioned evaluation method.
  • the coloring composition (b) for color filters according to the sixth aspect of the present invention comprises the coloring composition (a) for color filters which comprises the colorant for color filters which comprises colored composite microparticles comprising silica and an organic pigment wherein the silica is enclosed in the organic pigment, and contained in an amount of 0.001 to 9% by weight, calculated as Si, based on the weight of the colored composite microparticles, and the coloring composition base material; and a transparent resin containing an acid group and/or a latent acid group.
  • the transparent resin used in the present invention is not particularly restricted as long as the resin is soluble in an alkali developing solution, has no absorption band in a visible wavelength range, and exhibits a good film-forming property.
  • the transparent resin may include polymers substituted with at least one acid group, or polymers having at least one latent acid group capable of being converted into an acid group by deblocking reaction due to the effect of an acid.
  • the acid group usable in the present invention may include a phenolic hydroxyl group, a carboxyl group or the like.
  • the amount of the acid group and/or latent acid group introduced is not particularly limited, and may be appropriately adjusted so as to attain a suitable solubility of the transparent resin in an aqueous alkali solution.
  • Examples of the transparent resin having a phenolic hydroxyl group may include novolak resins, homopolymers or copolymers of 4-hydroxystyrene, or the like.
  • Examples of the transparent resin having a carboxyl group may include vinyl-based copolymers of an ethylenically unsaturated monomer containing a carboxyl group with the other copolymerizable unsaturated monomer.
  • Examples of the ethylenically unsaturated monomer having a carboxyl group may include acrylic acid, methacrylic acid, 2-acryloyloxyethyl phthalate, 2-acryloyloxypropyl phthalate, maleic acid, maleic anhydride, itaconic acid, itaconic anhydride, or the like.
  • the molar ratio of the carboxyl-containing ethylenically unsaturated monomer to the transparent resin is usually 0.005 to 0.5, preferably 0.05 to 0.4.
  • the resultant copolymer tends to be deteriorated in solubility in the aqueous alkali solution, resulting in occurrence of fouling or scumming upon patterning.
  • a coating film obtained from the resultant photosensitive composition tends to be undesirably swelled at insolubilized exposed portions thereof upon the alkali development after exposure to light, resulting in deterioration in definition or resolution as well as surface smoothness of the obtained coating film.
  • the carboxyl-containing transparent resin there may be used polyamic acids obtained by polyaddition reaction of tetracarboxylic dianhydride and diamine.
  • the tetracarboxylic dianhydride may include 1,2,3,4-cyclobutanetetracarboxylic dianhydride, 1,2,3,4-cyclopentanetetracarboxylic dianhydride, 1,2,3,5-cyclopentanetetracarboxylic dianhydride, 1,2,4,5-bicyclohexenetetracarboxylic dianhydride, 3,3′,4,4′-benzophenonetetracarboxylic dianhydride, pyromellitic dianhydride, 3,3′,4,4′-diphenylsulfonetetracarboxylic dianhydride, 3,3′,4,4′-biphenyltetracarboxylic dianhydride or the like.
  • these tetracarboxylic dianhydrides may be used in the form of a mixture of any two or more thereof.
  • Examples of the diamines reacted with these tetracarboxylic dianhydrides may include ethylenediamine, 1,3-diaminocyclohexane, 1,4-diaminocyclohexane, 4,4′-diaminodiphenyl ether, 3,4′-diaminodiphenyl ether, 4,4′-diaminodiphenyl methane, 3,3′-diaminodiphenyl methane, 4,4′-diaminodiphenyl sulfone, 3,3′-diaminodiphenyl sulfone, m-phenylenediamine, p-phenylenediamine, 2,4-diaminotolene, 2,5-diaminotolene or the like.
  • the polyamic acids may be synthesized in a polar organic solvent by known methods.
  • the polymerization degree of the polyamic acids may be controlled by varying the mixing molar ratio of the tetracarboxylic dianhydride to the diamine.
  • Examples of the latent acid group-containing transparent resin may include polymers containing a substituent group capable of producing a carboxyl group or a phenolic hydroxyl group by a catalytic action of an acid generated from the photo-acid generator, and base polymers used in alkali-developable chemically amplified photoresists.
  • latent acid group-containing transparent resin may include copolymers of cyclohexyl(meth)acrylate, tert-butyl(meth)acrylate, tert-amyl(meth)acrylate, 1,1-dimethylbenzyl(meth)acrylate, 1-ethoxyethyl(meth)acrylate, etc., with other acrylate monomers containing (meth)acrylic acid, homopolymers of 4-(tert-butoxycarbonyloxy)styrene, 4-(1-methoxyethoxy)styrene, 4-(1-ethoxyethoxy)styrene, etc., or copolymers of these monomers with 4-hydroxystyrene, or the like.
  • These transparent resins have a weight-average molecular weight of usually 2000 to 500000 and preferably 3000 to 300000.
  • These transparent resins substituted with an acid group and/or a latent acid group may be used in an amount of usually 5 to 500 parts by weight and preferably 7 to 300 parts by weight based on 100 parts by weight of the colorant for color filters.
  • the amount of the transparent resin used is less than 5 parts by weight, the resultant composition tends to be deteriorated in film-forming property and alkali developability.
  • the amount of the transparent resin used is more than 500 parts by weight, since the concentration of the pigment is relatively lowered, the thickness of the coating film must be increased to ensure a color concentration required for the color filter. As a result, it may be difficult to obtain a film having a uniform thickness, and the resultant color filter tends to be deteriorated in optical properties.
  • the volume-average dispersed particle diameter of the coloring composition (b) for color filters is usually 1 to 200 nm, preferably 1 to 150 nm and more preferably 1 to 100 nm.
  • the resultant composition tends to be deteriorated in optical properties owing to a too large particle size of the particles dispersed therein, thereby failing to achieve the objects of the present invention.
  • the coloring composition (b) for color filters has a viscosity of usually 0.5 to 1,000 mPa ⁇ s.
  • a viscosity of the coloring composition (b) is more than 1,000 mPa ⁇ s, it may difficult to obtain a uniform coating film.
  • the viscosity of the coloring composition (b) is less than 0.5 mPa ⁇ s, the thickness of the obtained coating film tends to be too small, thereby failing to achieve the objects of the present invention.
  • a rate of change (percentage of change) in viscosity thereof is usually not more than 20% and preferably not more than 10% as measured by the below-mentioned evaluation method.
  • the rate of change in viscosity of the coloring composition is more than 20%, the resultant composition may fail to maintain a good dispersibility under a stable dispersing condition for a long period of time.
  • the specific absorption coefficient at 650 nm (on the weight basis) of the coloring composition (b) for color filters is usually not less than 1.05, preferably 1.10 to 5.00 and more preferably 1.20 to 5.00 as measured by the below-mentioned evaluation method.
  • the specific absorption coefficient at 610 nm (on the weight basis) of the coloring composition (b) for color filters is usually not less than 1.05, preferably 1.10 to 5.00 and more preferably 1.20 to 5.00 as measured by the below-mentioned evaluation method.
  • the specific absorption coefficient at 550 nm (on the weight basis) of the coloring composition (b) for color filters is usually not less than 1.05, preferably 1.10 to 5.00 and more preferably 1.20 to 5.00 as measured by the below-mentioned evaluation method.
  • the specific absorption coefficient at 400 nm (on the weight basis) of the coloring composition (b) for color filters is usually not less than 1.05, preferably 1.10 to 5.00 and more preferably 1.20 to 5.00 as measured by the below-mentioned evaluation method.
  • the ⁇ E* value thereof is usually not more than 5.0, preferably not more than 4.5 and more preferably not more than 4.0 as measured by the below-mentioned evaluation method.
  • the heat resistance ( ⁇ E* value) is more than 5.0, the colored transparent film tends to be deteriorated in optical properties when subjected to heat treatments upon forming a color filter therefrom or vapor-depositing a ITO film thereon, thereby failing to achieve the objects of the present invention.
  • the light transmittance at 620 nm of the colored transparent film for color filters is usually not less than 80%, preferably not less than 85% and more preferably not less than 90%.
  • the light transmittance at 550 nm of the colored transparent film for color filters is usually not less than 80%, preferably not less than 85% and more preferably not less than 90%.
  • the specific absorption coefficient (on the weight basis) of the colored transparent film for color filters obtained from the coloring composition (b) for color filters is measured by the below-mentioned evaluation method.
  • the specific absorption coefficient at 650 nm (on the weight basis) of the colored transparent film for color filters is usually not less than 1.05, preferably 1.10 to 5.00 and more preferably 1.20 to 5.00.
  • the specific absorption coefficient at 610 nm (on the weight basis) of the colored transparent film for color filters is usually not less than 1.05, preferably 1.10 to 5.00 and more preferably 1.20 to 5.00.
  • the specific absorption coefficient at 550 nm (on the weight basis) of the colored transparent film for color filters is usually not less than 1.05, preferably 1.10 to 5.00 and more preferably 1.20 to 5.00.
  • the specific absorption coefficient at 400 nm (on the weight basis) of the colored transparent film for color filters is usually not less than 1.05, preferably 1.10 to 5.00 and more preferably 1.20 to 5.00.
  • the coloring composition (C) for color filters according to the seventh aspect of the present invention comprises the coloring composition (b) for color filters as defined in the sixth aspect which is produced by dispersing the coloring composition (a) for color filters which is obtained by dispersing, in a solvent, the colorant for color filters which comprises colored composite microparticles comprising silica and an organic pigment wherein the silica is enclosed in the organic pigment and contained in an amount of 0.001 to 9% by weight, calculated as Si, based on a weight of the colored composite microparticles, in a solution of a transparent resin containing an acid group and/or a latent acid group; a polyfunctional monomer containing two or more ethylenically unsaturated double bonds; and a photo-radical polymerization initiator.
  • polyfunctional monomer having two or more ethylenically unsaturated double bonds may include polyfunctional monomers such as ethyleneglycol di(meth)acrylate, diethyleneglycol di(meth)acrylate, trimethyleneglycol di(meth)acrylate, tetramethyleneglycol di(meth)acrylate, pentamethyleneglycol di(meth)acrylate, hexamethyleneglycol di(meth)acrylate, neopentylglycol di(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, stearic acid-modified pentaerythritol(meth)acrylate, trimethylolpropane tri(meth)acrylate, tris(acryloyloxyethyl)isocyanurate, dipentaerythritol hexaacrylate and dipentaerythrito
  • These polyfunctional monomers having two or more ethylenically unsaturated double bonds may be used in the form of a mixture with monofunctional monomers.
  • the monofunctional monomers may include methoxytriethyleneglycol(meth)acrylate, 2-hydroxy-3-phenoxypropyl(meth)acrylate, 2-acryloyloxyethyl succinate, 2-acryloyloxyethyl phthalate, 2-acryloyloxypropyl phthalate or the like.
  • These monofunctional monomers may be used in an amount of usually 0 to 80 parts by weight and preferably 0 to 40 parts by weight based on 100 parts by weight of the polyfunctional monomer. When the amount of the monofunctional monomers used is more than 80 parts by weight, the coating film obtained from the composition tends to be partially peeled off or deteriorated in definition or resolution upon the alkali development after exposure to light.
  • the photopolymerization initiator is a substance capable of efficiently generating radical species by irradiation with light, and serves for initiating polymerization of the polyfunctional monomer to form a crosslinked structure and reduce the alkali solubility of the acid group-containing transparent resin, thereby producing negative images.
  • the photopolymerization initiator may include keto-based compounds, triazine-based compounds containing a trichloromethyl group, electron transfer-type initiators or the like. Among them, preferred are such polymerization initiators capable of generating radical species by irradiation with ultraviolet light having a wavelength in the range of 200 to 450 nm.
  • the amount of the photopolymerization initiator used is not particularly limited as long as it is capable of initiating polymerization of the polyfunctional monomer having two or more ethylenically unsaturated double bonds, and the photopolymerization initiator may be used in an ordinary amount.
  • keto-based photopolymerization initiators usable in the present invention may include 2-hydroxy-2-methyl-1-phenylpropan-1-one, 1-hydroxy-1-benzoylcyclohexane, 2-morpholino-2-methyl-1-phenylpropan-1-one, 2-morpholino-2-methyl-1-(4-methoxyphenyl)propan-1-one, 2-morpholino-2-methyl-1-(4-methylthiophenyl)propan-1-one, 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)butan-1-one, 2-phenyl-2,2-dimethoxy-1-(4-methylthiophenyl)ethan-1-one, diphenylmesitylenephosphine oxide, phenacyltetramethylenesulfonium hexafluorophosphate or the like.
  • Examples of the sensitizing agent may include 9,10-dimethyl anthracene, 9,10-diphenyl anthracene, 9,10-bis(phenylethenyl)anthracene, 1,8-dimethyl-9,10-bis(phenylethenyl)anthracene, 9,10-dimethoxyanthracene, 9,10-diethoxyanthracene, 9,10-dipropoxyanthracene, 9,10-dibutoxyanthracene, thioxanthone, isopropylthioxanthone, 4,4′-bis(diethylamino)benzophenone or the like.
  • photopolymerization initiators composed of an electron donating compound and a sensitizing agent.
  • the suitable electron donating compound may include p-dimethylaminobenzoic acid esters, diethanolamine or the like.
  • the suitable sensitizing agent may include thioxanthone derivatives or the like.
  • One or more kinds of sensitizing agents may be used in combination with the above electron accepting compound or electron donating compound.
  • the photo-acid generator usable in the coloring composition (D) for color filters according to the present invention may be compounds applied to chemically amplified type photoresists or photo-cationic polymerization which have an absorption band in a wavelength range of 200 to 430 nm.
  • Examples of the photo-acid generator may include onium cationic compounds, halogen-containing compounds capable of generating a halogen acid, and sulfonated compounds capable of generating sulfonic acid.
  • halogen-containing compounds capable of generating a halogen acid may include 1-(3,4-dimethoxyphenyl)-3,5-bis(trichloromethyl)-s-triazine, 1-(4-methoxynaphthyl-1)-3,5-bis(trichloromethyl)-s-triazine, 1- ⁇ 2-(4-methoxyphenyl)ethenyl ⁇ -3,5-bis(trichloromethyl)-s-triazine, 1- ⁇ 2-(2-methoxyphenyl)ethenyl ⁇ -3,5-bis(trichloromethyl)-s-triazine, 1- ⁇ 2-(3,4-dimethoxyphenyl)ethenyl ⁇ -3,5-bis(trichloromethyl)-s-triazine, 1- ⁇ 2-(3-chloro-4-methoxyphenyl)ethenyl ⁇ -3,5-bis(trichloromethyl)-s-triazine, 1-(b)
  • the amount of the photo-acid generator used is usually 0.1 to 20 parts by weight and preferably 0.5 to 10 parts by weight based on 100 parts by weight of the transparent resin.
  • the number-average dispersed particle diameter of the respective coloring compositions (C) and (D) for color filters according to the present invention is usually 1 to 200 nm, preferably 1 to 150 nm, more preferably 1 to 100 nm and still more preferably 1 to 50 nm.
  • the resultant compositions tend to be deteriorated in optical properties owing to a too large particle size of the particles dispersed therein, thereby failing to achieve the objects of the present invention.
  • the coloring compositions (C) and (D) for color filters according to the present invention respectively have a viscosity of usually 0.5 to 1,000 mPa ⁇ s.
  • a viscosity of the respective coloring compositions (C) and (D) is more than 1,000 mPa ⁇ s, it may difficult to obtain a uniform coating film.
  • the viscosity of the respective coloring compositions (C) and (D) is less than 0.5 mPa ⁇ s, the thickness of the obtained coating film tends to be too small, thereby failing to achieve the objects of the present invention.
  • the rate of change in viscosity thereof is usually not more than 20% and preferably not more than 10% as measured by the below-mentioned evaluation method.
  • the rate of change in viscosity of the respective coloring compositions is more than 20%, the resultant compositions may fail to stably maintain a good dispersibility for a long period of time.
  • the specific absorption coefficient at 650 nm (on the weight basis) of the respective coloring compositions (C) and (D) for color filters according to the present invention is usually not less than 1.05, preferably 1.10 to 5.00 and more preferably 1.20 to 5.00 as measured by the below-mentioned evaluation method.
  • the specific absorption coefficient at 610 nm (on the weight basis) of the respective coloring compositions (C) and (D) for color filters is usually not less than 1.05, preferably 1.10 to 5.00 and more preferably 1.20 to 5.00 as measured by the below-mentioned evaluation method.
  • the specific absorption coefficient at 550 nm (on the weight basis) of the respective coloring compositions (C) and (D) for color filters is usually not less than 1.05, preferably 1.10 to 5.00 and more preferably 1.20 to 5.00 as measured by the below-mentioned evaluation method.
  • the specific absorption coefficient at 400 nm (on the weight basis) of the respective coloring compositions (C) and (D) for color filters is usually not less than 1.05, preferably 1.10 to 5.00 and more preferably 1.20 to 5.00 as measured by the below-mentioned evaluation method.
  • the ⁇ E* value thereof is usually not more than 5.0, preferably not more than 4.5 and more preferably not more than 4.0 as measured by the below-mentioned evaluation method.
  • the light fastness ( ⁇ E* value) is more than 5.0, the resultant color filter tends to be deteriorated in optical properties owing to irradiation with a backlight, etc., thereby failing to achieve the objects of the present invention.
  • the ⁇ E* value thereof is usually not more than 5.0, preferably not more than 4.5 and more preferably not more than 4.0 as measured by the below-mentioned evaluation method.
  • the heat resistance ( ⁇ E* value) is more than 5.0, the colored transparent film tends to be deteriorated in optical properties when subjected to heat treatments upon forming a color filter therefrom or vapor-depositing a ITO film thereon, thereby failing to achieve the objects of the present invention.
  • the specific absorption coefficient at 650 nm (on the weight basis) of a colored transparent film obtained from the respective coloring compositions (C) and (D) for color filters according to the present invention is usually not less than 1.20, preferably 1.40 to 5.00 and more preferably 1.50 to 5.00 as measured by the below-mentioned evaluation method.
  • the specific absorption coefficient at 610 nm (on the weight basis) of the colored transparent film is usually not less than 1.20, preferably 1.40 to 5.00 and more preferably 1.50 to 5.00 as measured by the below-mentioned evaluation method.
  • the specific absorption coefficient at 550 nm (on the weight basis) of the colored transparent film is usually not less than 1.20, preferably 1.40 to 5.00 and more preferably 1.50 to 5.00 as measured by the below-mentioned evaluation method.
  • the specific absorption coefficient at 400 nm (on the weight basis) of the colored transparent film is usually not less than 1.20, preferably 1.40 to 5.00 and more preferably 1.50 to 5.00 as measured by the below-mentioned evaluation method.
  • the color filter according to the ninth aspect of the present invention is constituted of a film-shaped product formed from the coloring composition (b) for color filters as defined in the sixth aspect which is produced by dispersing the coloring composition (a) for color filters which is obtained by dispersing in a solvent, the colorant for color filters which comprises colored composite microparticles comprising silica and an organic pigment wherein the silica is enclosed in the organic pigment and contained in an amount of 0.001 to 9% by weight, calculated as Si, based on the weight of the colored composite microparticles, in a solution of a transparent resin containing an acid group and/or a latent acid group.
  • the color filter according to the tenth aspect of the present invention is constituted of (I) a film-shaped product formed from the coloring composition (C) for color filters comprising the coloring composition (b) for color filters as defined in the sixth aspect which is produced by dispersing the coloring composition (a) for color filters which is obtained by dispersing in a solvent, the colorant for color filters which comprises colored composite microparticles comprising silica and an organic pigment wherein the silica is enclosed in the organic pigment and contained in an amount of 0.001 to 9% by weight, calculated as Si, based on a weight of the colored composite microparticles, in a solution of a transparent resin containing an acid group and/or a latent acid group; a polyfunctional monomer containing two or more ethylenically unsaturated double bonds; and a photo-radical polymerization initiator, or (II) a film-shaped product formed from the coloring composition (D) for color filters comprising the coloring composition (b) for color filters as defined in the sixth aspect which
  • the respective color filters have a light transmittance in each color transmission range of usually not less than 75%, preferably not less than 80% and more preferably not less than 85%; and a contrast of usually not less than 800, preferably not less than 1000 and more preferably not less than 1200.
  • the coloring composition (a) for color filters according to the present invention may be produced by re-dispersing the colorant for color filters according to the present invention in an organic solvent or an oil vehicle, or by subjecting the composite particles to dissolution treatment, separating a solid component from the dissolution solution by filtration, washing the thus separated solid component with water, flashing a wet cake of the solid component with an organic solvent or an oil vehicle, and then dispersing the thus treated solid component in the organic solvent or the oil vehicle.
  • the dispersing treatment may be conducted using a ball mill, a beads mill, a sand mill, an edge runner, a twin or triple roll mill, an extruder, a high-speed impact mill, or the like.
  • a grinding medium for grinding-type mills such as the ball mill and beads mill
  • steel beads, glass beads, ceramic beads, etc. according to the kind of material of the mill used.
  • the size of the grinding medium is usually 0.01 to 10 mm and preferably 0.03 to 3 mm.
  • the grinding temperature is not particularly limited, and may be controlled, for example, to the range of from room temperature to a boiling point of the solvent used.
  • Additives such as a dispersant, a pigment derivative, a defoaming agent and a surfactant may be added to the composition, if required.
  • the coloring composition (b) for color filters according to the present invention may be produced by dissolving the coloring composition (a) for color filters in a transparent resin containing an acid group or a transparent resin containing a latent acid group; or by mixing and dispersing the colorant for color filters in a solvent into which the transparent resin containing an acid group or the transparent resin containing a latent acid group is previously dissolved.
  • the photosensitivity-imparted coloring composition (C) for color filters according to the present invention may be produced by adding the photopolymerization initiator and the polyfunctional monomer having two or more ethylenically unsaturated double bonds to the coloring composition (b) containing the transparent resin containing an acid group, and then mixing these components with each other.
  • a solvent may be added to the composition, if required, to suitably adjust the pigment concentration, viscosity, etc.
  • a polymerization inhibitor, a curing accelerator such as 2-mercaptobenzoimidazole, etc. may be added to the composition.
  • the photosensitivity-imparted coloring composition (D) for color filters according to the present invention may be produced by adding a photo-acid generator to the coloring composition (b) containing the transparent resin containing a latent acid group, and then mixing these components with each other.
  • the coloring composition for color filters according to the present invention is applied onto a transparent substrate on which black matrix patterns are formed, and then pre-baked to fully evaporate and remove the solvent therefrom, thereby obtaining a colored coating film.
  • an alkali-developable positive photoresist layer is formed on the colored coating film, thereby obtaining a coating film with a two-layer structure.
  • the alkali-developable positive photoresist there may be suitably used quinonediazide-based photoresists.
  • the thus obtained colored coating film is irradiated with light through a photo mask, and then developed with an aqueous alkali solution. Since the light-exposed portion of the positive photoresist-coated film becomes alkali-soluble, the underlying colored layer exposed by the alkali development is also etched by the alkali solution, thereby obtaining a colored positive image. Then, the photoresist layer is selectively removed by a solvent to obtain a colored pattern.
  • the coating film formed from the photosensitive coloring composition (C) for color filters is directly usable as a colored photosensitive layer.
  • the coating film may be exposed to light through a photo mask, and then alkali-developed to insolubilize the exposed portion, thereby obtaining a negative colored pattern.
  • the developing treatment may be conducted by dipping method, spraying method, paddle method, shower method, etc. After the alkali development, the resultant film is washed with water and then dried.
  • the transparent substrate there may be used such substrates made of silica glass as well as polycarbonates, polyesters, polyamides, polyimides, polyamide imides, etc. Also, in order to produce a solid image pickup device, there may be used a silicon substrate.
  • the coloring composition for color filters may be applied onto the transparent substrate by an appropriate method such as rotary coating, cast coating, roll coating, screen printing and ink-jet printing.
  • the thickness of the coating film varies depending upon concentration of the colorant for color filters used, and is usually 0.1 to 10 ⁇ m and preferably 0.2 to 5.0 ⁇ m.
  • the colorant for inks for ink-jet printing according to the eleventh aspect of the present invention comprises the colored composite microparticles as defined, in the first aspect which comprise silica and an organic pigment wherein the silica is enclosed in the organic pigment and contained in an amount of 0.001 to 9% by weight, calculated as Si, based on the weight of the colored composite microparticles.
  • the number-average particle diameter of the colorant for inks for ink-jet printing is usually not more than 150 nm, preferably 1 to 100 nm, more preferably 1 to 50 nm and still more preferably 1 to 40 nm.
  • the resultant ink for ink-jet printing tends to cause clogging of a head portion of an ink-jet printer used owing to a too large particle size thereof.
  • the ⁇ E* value thereof is usually not more than 5.0, preferably not more than 4.5 and more preferably not more than 4.0 as measured by the below-mentioned evaluation method.
  • the light fastness ( ⁇ E* value) of the colorant for inks for ink-jet printing is more than 5.0, printed matters printed with the resultant ink for ink-jet printing may fail to exhibit a sufficient light fastness.
  • the specific absorption coefficient ⁇ w (on the weight basis) representing a tinting strength of the ink for ink-jet printing is usually not less than 1.20, preferably 1.40 to 5.00 and more preferably 1.50 to 5.00 as measured by the below-mentioned evaluation method.
  • the amount of the colorant contained in the ink for ink-jet printing is usually 1 to 20% by weight based on the weight of the ink base solution.
  • the ink base solution as a constitutional component of the ink for ink-jet printing according to the present invention contains a solvent and a dispersant and may also optionally contain a water-soluble resin, a penetrant, a humectant, a water-soluble solvent, a pH modifier and/or an antiseptic agent, if required.
  • the content of the optional components such as the water-soluble resin, penetrant, humectant, water-soluble solvent, pH modifier, and/or antiseptic agent in the ink base solution is usually not more than 50% by weight.
  • anionic surfactants may include fatty acid salts, salts of sulfuric esters, sulfonic acid salts, salts of phosphoric esters, or the like.
  • anionic surfactants preferred are salts of sulfuric esters and sulfonic acid salts.
  • nonionic surfactants may include polyethyleneglycol-type nonionic surfactants such as polyoxyethylene alkyl ethers and polyoxyethylene aryl ethers; and polyhydric alcohol-type nonionic surfactants such as sorbitan fatty esters.
  • polyethyleneglycol-type nonionic surfactants such as polyoxyethylene alkyl ethers and polyoxyethylene aryl ethers
  • polyhydric alcohol-type nonionic surfactants such as sorbitan fatty esters.
  • cationic surfactants may include amine salt-type cationic surfactants, quaternary ammonium salt-type cationic surfactants, or the like. Among these cationic surfactants, preferred are the quaternary ammonium salt-type cationic surfactants.
  • high-molecular dispersants may include alkali-soluble resins such as styrene-acrylic acid copolymers, styrene-maleic acid copolymers and polyacrylic acid derivatives.
  • the solvent for the ink for ink-jet printing is composed of water and, if required, a water-soluble organic solvent.
  • the content of the water-soluble organic solvent in the ink for ink-jet printing is usually not more than 50% by weight, preferably 1 to 50% by weight, more preferably 1 to 40% by weight and still more preferably 1 to 30% by weight based on the weight of the ink base solution.
  • water-soluble organic solvent may include monohydric alcohols such as methanol, ethanol, n-propanol, isopropanol and butanol; dihydric alcohols such as ethyleneglycol, diethyleneglycol, triethyleneglycol, tetraethyleneglycol, propyleneglycol and dipropyleneglycol; trihydric alcohols such as glycerol; polyalkyleneglycols such as polyethyleneglycol and polypropyleneglycol; and lower alkyl ethers of polyhydric alcohols such as diethyleneglycol monobutyl ether, ethyleneglycol monobutyl ether, triethyleneglycol monobutyl ether and ethyleneglycol monoethyl ether. These water-soluble organic solvents may be used in combination of any two or more thereof.
  • monohydric alcohols such as methanol, ethanol, n-propanol, isopropanol and butanol
  • dihydric alcohols such
  • the dispersing apparatus there may be used a ball mill, a sand mill, an attritor, a roll mill, a beads mill, a colloid mill, a twin or triple roll mill, an ultrasonic homogenizer, a high-pressure homogenizer, etc.
  • the reason why the colored composite microparticles of the present invention can exhibit a high tinting strength and an excellent dispersibility is considered by the present inventors as follows.
  • merely finely divided organic pigment tends to suffer from agglomeration because of a very high surface energy of the particles, so that it may be difficult to allow the organic pigment to maintain the fine particle condition in vehicles.
  • silica since silica is enclosed in the organic pigment, an absolute value of a ⁇ potential of the resultant particles is increased, resulting in a good electrostatic repulsion effect thereof in the vehicles.
  • the obtained colored composite microparticles can be dispersed in the vehicles in a finely divided condition, thereby attaining a high tinting strength.
  • the colorant for color filters according to the present invention comprises fine primary particles, exhibits a high tinting strength and an excellent dispersibility in vehicles, and are further excellent in light fastness and heat resistance.
  • the colorant for color filters according to the present invention can exhibit a high tinting strength and an excellent dispersibility and are further excellent in light fastness and heat resistance. That is, the colorant for color filters according to the present invention is composed of the above colored composite microparticles. Also, since the silica having a high heat resistance and a high light fastness is enclosed in the organic pigment, the resultant composite particles can maintain a high heat resistance and a high light fastness or can be improved in these properties even when the organic pigment is finely divided.
  • the color filter using the film-shaped product comprising the coloring composition for color filters according to the present invention is excellent in optical properties, light fastness and heat resistance, is considered by the present inventors as follows. That is, in the color filter, there is used the colorant for color filters according to the present invention which are not only in the form of fine particles but also excellent dispersibility, light fastness and heat resistance.
  • the colorant used in the ink for ink-jet printing according to the present invention has a fine primary particle diameter and a uniform particle size distribution, exhibits a high tinting strength and an excellent dispersibility, and is further excellent in light fastness.
  • the colorant used in the ink for ink-jet printing can exhibit a high tinting strength and excellent dispersibility and light fastness. That is, the colorant used in the ink for ink-jet printing comprises the above colored composite microparticles.
  • the reason why the ink for ink-jet printing according to the present invention can exhibit an excellent dispersion stability is considered by the present inventors as follows. That is, owing to the use of the colorant for inks for ink-jet printing according to the present invention, since the silica is enclosed in the organic pigment, an absolute value of the ⁇ potential of the resultant colorant is increased and a good electrostatic repulsion effect thereof in vehicles can be attained, so that the colorant can be dispersed in a finely divided condition even in the vehicles, thereby enabling the colorant to maintain an excellent dispersibility in the ink for ink-jet printing.
  • the colored composite microparticles according to the first aspect of the present invention exhibit a high tinting strength and is excellent in dispersibility and light fastness, and therefore, can be suitably used as a colorant in various applications.
  • the dispersion according to the second aspect of the present invention contains the colored composite microparticles having the above properties as a colorant, and therefore, can be suitably used as a dispersion in various applications.
  • the colored composite microparticles and the dispersion according to the present invention can be used as a colorant in various applications such as ordinarily used paints and printing inks irrespective of a water-based system or a solvent-based system.
  • the colorant for color filters according to the fourth aspect of the present invention not only has a fine primary particle diameter, but also exhibits a high tinting strength and an excellent dispersibility in vehicles, and is further excellent in light fastness and heat resistance, and therefore, can be suitably used as a colorant for color filters.
  • the coloring compositions for color filters according to the fifth to eighth aspects of the present invention are excellent in dispersibility, dispersion stability, light fastness and heat resistance owing to the use of the colorant for color filters having the above properties, and therefore, can be suitably used as a coloring composition for color filters which can also exhibit an excellent transparency.
  • the color filters according to the ninth and tenth aspects of the present invention are excellent in spectral properties, light fastness and heat resistance owing to the use of the coloring composition for color filters which comprises the colorant for color filters having the above properties, and therefore, can be suitably used as a color filter.
  • the colorant for inks for ink-jet printing according to the eleventh aspect of the present invention has a fine primary particle diameter and a uniform particle size distribution, exhibits a high tinting strength and an excellent dispersibility, and is further excellent in light fastness, and therefore, can be suitably used as a colorant for inks for ink-jet printing.
  • the ink for ink-jet printing according to the present invention can be suitably used as an ink for ink-jet printing which is excellent in dispersibility, dispersion stability and light fastness, owing to use of the colorant for inks for ink-jet printing as defined in eleventh aspect.
  • the colored composite microparticles according to the first aspect of the present invention exhibit a high tinting strength, and are excellent in dispersibility and light fastness, and therefore, can be suitably used in various applications such as ordinarily used paints, printing inks, etc., irrespective of an aqueous system or a solvent system.
  • the colored composite microparticles exhibiting a high tinting strength and excellent dispersibility and light fastness are used as a colorant. Therefore, the dispersion can be suitably used in various applications.
  • the colorant according to the fourth aspect of the present invention not only has a fine primary particle diameter but also exhibits a high tinting strength and an excellent dispersibility in vehicles, and are excellent in light fastness and heat resistance, and therefore, can be suitably used as a colorant for color filters.
  • the coloring compositions according to the fifth to eighth aspects of the present invention there is used the colorant for color filters having a high tinting strength and excellent dispersibility, light fastness and heat resistance.
  • the coloring compositions are excellent in not only dispersibility, dispersion stability, light fastness and heat resistance, but also transparency, and therefore, can be suitably used as a coloring composition for color filters.
  • the colorant according to the eleventh aspect of the present invention has a fine primary particle diameter and a uniform particle size distribution, and exhibits a high tinting strength, an excellent dispersibility and an excellent light fastness. Therefore, the colorant can be suitably used as a colorant for inks for ink-jet printing.
  • the colorant for inks for ink-jet printing which is in the form of fine particles having a uniform particle size, has a high tinting strength, and is excellent in dispersibility and light fastness. Therefore, the ink for ink-jet printing is excellent in dispersibility, dispersion stability and light fastness.
  • the average particle diameter of primary particles of the respective particles was expressed by an average value of particle diameters of 350 particles observed on a micrograph.
  • the particle size distribution of primary particles of the respective particles was expressed by the geometrical standard deviation value obtained by the following method. That is, the particle sizes were measured from the above magnified micrograph. The actual particle sizes and the number of the particles were obtained from the calculation on the basis of the measured values. On a logarithmic normal probability paper, the particle sizes were plotted at regular intervals on the abscissa-axis and the accumulative number of particles (under integration sieve) belonging to each interval of the particle sizes were plotted by percentage on the ordinate-axis by a statistical technique. The particle sizes corresponding to the number of particles of 50% and 84.13%, respectively, were read from the graph, and the geometrical standard deviation was obtained from the following formula:
  • Geometrical standard deviation ⁇ particle size corresponding to 84.13% under integration sieve ⁇ / ⁇ particle size (geometrical average diameter) corresponding to 50% under integration sieve ⁇
  • the number-average particle diameter and the volume-average particle diameter of the respective particles were determined by the following method.
  • An aqueous solution prepared by mixing the particles to be measured with water was dispersed for 1 min using an ultrasonic dispersing apparatus, and then the respective average particle diameters of the particles dispersed therein were measured by a dynamic light scattering method using a concentrated particle size analyzer “FPAR-1000” manufactured by Otsuka Denshi Co., Ltd.
  • the specific surface area was expressed by the value measured by a BET method.
  • the amount of the surface modifying agent coated on the surface of the silica particles, and the amount of the organic pigment adhered onto the composite particles, were respectively determined by measuring the carbon contents using “Horiba Metal, Carbon and Sulfur Analyzer EMIA-2200 Model” (manufactured by Horiba Seisakusho Co., Ltd.).
  • the ⁇ potentials of the organic pigment, the composite particles, the colored composite microparticles, the colorant for color filters and the colorant for inks for ink-jet printing were respectively determined as follows.
  • the organic pigment, the composite particles, the colored composite microparticles, the colorant for color filters and the colorant for inks for ink-jet printing were respectively added to ion-exchanged water in the case of a water-based system or PGMEA (propyleneglycol monomethyl ether acetate) in the case of a solvent system to prepare a dispersion having a concentration of 0.5 g/L, and the resultant dispersion was dispersed for 3 min using an ultrasonic dispersing apparatus to measure the ⁇ potential thereof by electrophoresis using “Model 501” manufactured by PEN KEN Inc.
  • a primary color enamel and a vehicle enamel prepared by the below-mentioned methods were respectively applied on a cast-coated paper by using a 150 ⁇ m (6 mil) applicator to produce coating film pieces.
  • the L* values of the thus obtained coating film pieces were measured by a spectrophotometric colorimeter “CM-3610d” (manufactured by MINOLTA CO., LTD.). The difference between the obtained L* values was represented by a ⁇ L* value.
  • the same procedure as defined above was conducted to prepare an primary color enamel and a vehicle enamel, form respective coating film pieces and then measure L* values thereof.
  • the difference between the L* values was represented by a ⁇ Ls* value.
  • the tinting strength (%) was calculated according to the following formula:
  • Tinting strength (%) 100+ ⁇ ( ⁇ Ls* ⁇ L *) ⁇ 10 ⁇
  • the primary color enamel prepared above for measuring the tinting strength was applied onto a cold rolled steel plate (0.8 mm ⁇ 70 mm ⁇ 150 mm) and dried to form a coating film having a thickness of 150 ⁇ m.
  • One half of the thus prepared coating film piece was covered with a metal foil, and an ultraviolet light was continuously irradiated over the coating film piece at an intensity of 100 mW/cm 2 for 6 hr using “EYE SUPER UV TESTER SUV-W13” (manufactured by IWASAKI DENKI CO., LTD.).
  • the hue values (L*, a* and b* values) of the metal foil-covered UV-unirradiated portion and the UV-irradiated portion of the coating film piece were respectively measured.
  • the light fastness was expressed by the ⁇ E* value calculated according to the following formula:
  • ⁇ L* represents the difference between L* values of the UV-unirradiated and UV-irradiated portions
  • ⁇ a* represents the difference between a* values of the UV-unirradiated and UV-irradiated portions
  • ⁇ b* represents the difference between b* values of the UV-unirradiated and UV-irradiated portions.
  • the degree of desorption of the adhered organic pigment from the composite particles was evaluated by the following method, and the results were classified into the following four ranks.
  • the Rank 4 represents that the amount of the organic pigment desorbed from the surface of the composite particles was small.
  • the primary color enamel prepared above for measuring the tinting strength was applied onto a glass plate (0.8 mm ⁇ 70 mm ⁇ 150 mm) and dried to form a coating film having a thickness of 150 ⁇ m.
  • the thus formed coating film was allowed to stand in a Geer oven at 240° C. for 1 hr to measure the hue values (L*, a* and b* values) of the coating film before and after being subjected to the heat treatment test.
  • the heat resistance was expressed by the ⁇ E* value calculated according to the following formula:
  • ⁇ L* represents the difference between L* values of the sample between before and after being subjected to the heat treatment test
  • ⁇ a* represents the difference between a* values of the sample between before and after being subjected to the heat treatment test
  • ⁇ b* represents the difference between b* values of the sample between before and after being subjected to the heat treatment test.
  • the number-average dispersed particle diameter and the volume-average dispersed particle diameter of the dispersion containing the colored composite microparticles, the coloring composition for color filters and the ink for ink-jet printing were measured by a dynamic light scattering method using a concentrated particle size analyzer “FPAR-1000” manufactured by Otsuka Denshi Co., Ltd.
  • the dispersion stability of the dispersion and the ink for ink-jet printing was determined by the following method. That is, 25 mL of dispersion to be measured was filled in a 50 mL color comparison tube and allowed to stand at 60° C. for one week, and then visually observed to evaluate a degree of precipitation of the particles dispersed therein. The evaluation results are classified into the following five ranks.
  • the rate of change (percentage of change) in viscosity of the dispersion containing the colored composite microparticles and the coloring composition for color filters were determined by the following method. That is, after the obtained dispersion was allowed to stand at 60° C. for one week, the viscosity of the dispersion was measured at 25° C. and a shear rate (D) of 383 sec ⁇ 1 using “E-type Viscometer EMD-R” (manufactured by Tokyo Keiki Co., Ltd.). The rate of change in viscosity of the dispersion was expressed by the percentage obtained by dividing the difference between the viscosity values measured before and after the standing test by the viscosity value measured before the standing test.
  • the tinting strengths of the dispersion containing the colored composite microparticles and the coloring composition for color filters were respectively determined by the following method. That is, in the case of a water-based dispersion, an aqueous solution prepared by adjusting the concentration of each of the colored composite microparticles and the colorant for color filters to 0.08% by weight was filled in a quartz cell, whereas in the case of a solvent-based dispersion, a PGMEA solution prepared by adjusting the concentration of each of the colored composite microparticles and the colorant for color filters to 0.08% by weight was filled in a quartz cell.
  • the absorption coefficient of the respective dispersions at a wavelength at which light absorption was largest was measured using a self-recording photoelectric spectrophotometer “UV-2100” (manufactured by SHIMADZU SEISAKUSHO CO., LTD.).
  • the tinting strengths of the respective materials were expressed by a specific absorption coefficient ⁇ w calculated according to the following formula:
  • ⁇ w represents a specific absorption coefficient
  • ⁇ h represents an absorption coefficient per unit weight of each of the colored composite microparticles and the colorant for color filters
  • ⁇ 0 represents an absorption coefficient per unit weight of the organic pigment used as a raw material for each of the colored composite microparticles and the colorant for color filters.
  • the viscosity of the coloring composition for color filters was expressed by the value obtained by measuring the viscosity of the resultant composition at 25° C. and a shear rate (D) of 383 sec ⁇ 1 using “E-type Viscometer EMD-R” (manufactured by Tokyo Keiki Co., Ltd.).
  • the light transmittance of the coloring composition for color filters was determined by the following method. That is, the coloring composition for color filters was diluted such that the concentration of the organic pigment therein was 0.008% by weight, and the resultant diluted solution of the composition was filled in a quartz cell.
  • the chromaticity of the colored transparent film obtained from the coloring composition for color filters was determined by the following method. That is, the coloring composition for color filters prepared by the below-mentioned method was applied onto a clear base film to form a coating film having a thickness of 150 ⁇ m, and then dried to obtain a coating film piece. The chromaticity of the thus obtained coating film piece was measured using a spectrophotometric calorimeter “CM-3610d” (manufactured by MINOLTA CO., LTD.), and expressed according to XY chromaticity diagram prescribed by CIE (Commission Internationale de I'Eclairage).
  • CM-3610d manufactured by MINOLTA CO., LTD.
  • the light fastness of the colored transparent film for color filters obtained from the coloring composition for color filters was determined by the following method. That is, the coloring composition for color filters was applied onto a glass plate (0.8 mm ⁇ 70 mm ⁇ 150 mm) to form a coating film having a thickness of 150 ⁇ m and then dried, thereby obtaining a coating film piece. A part of the thus prepared coating film piece was covered with a metal foil, and an ultraviolet light was continuously irradiated over the coating film piece at an intensity of 100 mW/cm 2 for 6 hr using “EYE SUPER UV TESTER SUV-W13” (manufactured by IWASAKI DENKI CO., LTD.).
  • the hue values (L*, a* and b* values) of the metal foil-covered UV-unirradiated portion and the UV-irradiated portion of the coating film piece were respectively measured using a spectrophotometric colorimeter “CM-3610d” (manufactured by MINOLTA CO., LTD.).
  • CM-3610d manufactured by MINOLTA CO., LTD.
  • the light fastness was expressed by the ⁇ E* value calculated according to the following formula:
  • ⁇ L* represents the difference between L* values of the UV-unirradiated and UV-irradiated portions of the sample
  • ⁇ a* represents the difference between a* values of the UV-unirradiated and UV-irradiated portions of the sample
  • ⁇ b* represents the difference between b* values of the UV-unirradiated and UV-irradiated portions of the sample.
  • the heat resistance of the colored transparent film for color filters obtained from the coloring composition for color filters was determined by the following method. That is, the above coloring composition for color filters was applied onto a glass plate (0.8 mm ⁇ 70 mm ⁇ 150 mm) and dried to form a coating film having a thickness of 150 ⁇ m. The thus formed coating film piece was allowed to stand in a Geer oven at 240° C. for 1 hr to measure the hue values (L*, a* and b* values) of the coating film piece before and after being subjected to the heat treatment test. The heat resistance was expressed by the ⁇ E* value calculated according to the following formula:
  • ⁇ L* represents the difference between L* values of the sample between before and after being subjected to the heat treatment test
  • ⁇ a* represents the difference between a* values of the sample between before and after being subjected to the heat treatment test
  • ⁇ b* represents the difference between b* values of the sample between before and after being subjected to the heat treatment test.
  • the light transmittance of the colored transparent film for color filters obtained from the coloring composition for color filters was determined by the following method. That is, using the coating film piece used for measuring the chromaticity of the colored transparent film for color filters, the light transmittance at a wavelength of 530 nm in the case of the green-based colored transparent film for color filters, the light transmittance at a wavelength of 460 nm in the case of the blue-based colored transparent film for color filters, the light transmittance at a wavelength of 620 nm in the case of the red-based colored transparent film for color filters, and the light transmittance at a wavelength of 550 nm in the case of the yellow-based colored transparent film for color filters, were respectively measured using a self-recording photoelectric spectrophotometer “UV-2100” (manufactured by SHIMADZU SEISAKUSHO CO., LTD.).
  • the light transmittance of the color filter was determined by the following method. That is, using the color filter produced by the below-mentioned method, the light transmittances thereof at respective wavelengths of 530 nm, 460 nm and 620 nm were measured using a self-recording photoelectric spectrophotometer “UV-2100” (manufactured by SHIMADZU SEISAKUSHO CO., LTD.).
  • the contrast of the color filter was determined by the following method. That is, the color filter prepared by the below-mentioned method was interposed between two polarizing plates on a back light, and the brightness (A) when arranging the two polarizing plates in parallel with each other and the brightness (B) when arranging the two polarizing plates perpendicularly to each other were respectively measured. The contrast was expressed by a ratio of (A) to (B) ((A)/(B)).
  • the tinting strength of the ink for ink-jet printing was determined by the following method. That is, an aqueous solution prepared by adjusting the concentration of the colorant for inks for ink-jet printing to 0.08% by weight was filled in a quartz cell. The absorption coefficient of the solution at a wavelength at which light absorption was largest was measured using a self-recording photoelectric spectrophotometer “UV-2100” (manufactured by SHIMADZU SEISAKUSHO CO., LTD.). The tinting strength of the ink for ink-jet printing was expressed by a specific absorption coefficient ⁇ w calculated according to the following formula:
  • ⁇ w represents a specific absorption coefficient
  • ⁇ h represents an absorption coefficient per unit weight of each colorant for inks for ink-jet printing
  • ⁇ 0 represents an absorption coefficient per unit weight of the organic pigment used as a raw material for each colorant for inks for ink-jet printing.
  • the average particle diameter (Dd 50 ), the particle diameter (Dd 84 ) and the maximum particle diameter (Dd 99 ) of the particles dispersed in the ink for ink-jet printing were measured by a dynamic light scattering method using a concentrated particle size analyzer “FPAR-1000” (manufactured by Otsuka Denshi Co., Ltd.). Meanwhile, the geometrical standard deviation (Dd 84 /Dd 50 ) was expressed by the value calculated according to the following formula:
  • Geometrical standard deviation ( Dd 84 /Dd 50 ) ⁇ particle size ( Dd 84 ) corresponding to 84.13% under integration sieve ⁇ / ⁇ particle size ( Dd 50 ) corresponding to 50% under integration sieve ⁇
  • the rate of change (percentage of change) in number-average dispersed particle diameter of the ink for ink-jet printing was determined by the following method. That is, after the ink was allowed to stand at 60° C. for one month, the number-average dispersed particle diameter was measured by a dynamic light scattering method using a concentrated particle size analyzer “FPAR-1000” (manufactured by Otsuka Denshi Co., Ltd.). The rate of change in number-average dispersed particle diameter of the ink for ink-jet printing was expressed by the percentage obtained by dividing the difference between the number-average dispersed particle diameters measured before and after the standing test by the number-average dispersed particle diameter measured before the standing test.
  • the hue and chroma of the ink for ink-jet printing were determined by the following method. That is, hue values of printed images recorded on a plain paper “KB” (produced by KOKUYO Co., Ltd.) were measured using a multi-spectro-colour-meter “MSC-IS-2D” (manufactured by SUGA SHIKENKI CO., LTD.) to determine color specification values (L*, a* and b* values) thereof according to JIS Z 8729 as well as the C* value thereof.
  • MSC-IS-2D multi-spectro-colour-meter
  • a plain paper “KB” (produced by KOKUYO Co., Ltd.) was printed with the ink for ink-jet printing, and a half of the thus printed paper was covered with a metal foil, and an ultraviolet light was continuously irradiated over the printed paper at an intensity of 100 mW/cm 2 for 6 hr using “EYE SUPER UV TESTER SUV-W13” (manufactured by IWASAKI DENKI CO., LTD.).
  • the hue values (L*, a* and b* values) of the metal foil-covered UV-unirradiated portion and the UV-irradiated portion of the printed paper were respectively measured using a multi-spectro-colour-meter “MSC-IS-2D” (manufactured by SUGA SHIKENKI CO., LTD.).
  • MSC-IS-2D multi-spectro-colour-meter
  • ⁇ L* represents the difference between L* values of the UV-unirradiated and UV-irradiated portions of the sample
  • ⁇ a* represents the difference between a* values of the UV-unirradiated and UV-irradiated portions of the sample
  • ⁇ b* represents the difference between b* values of the UV-unirradiated and UV-irradiated portions of the sample.
  • the anti-clogging property of the ink for ink-jet printing was determined by the following method. That is, the ink was filled in a cartridge of an ink-jet printer “Deskjet 970Cxi” manufactured by HEWLETT PACKARD Corp., and a plain paper “KB” (produced by KOKUYO Co., Ltd.) was printed therewith at room temperature to visually observe and evaluate defects and lacks of the obtained printed images as well as the degree of non-ejection of the ink. The evaluation results are classified into the following five ranks.
  • Examples 1 to 3 concerning the colored composite microparticles and the dispersion thereof according to the first to third aspects of the present invention as well as the corresponding Comparative Examples (Comparative Examples 1 to 3) are described.
  • methylhydrogenpolysiloxane (tradename: “TSF484”, produced by GE TOSHIBA SILICONE CO., LTD.) was added to 7.0 kg of silica 1 (average particle diameter of primary particles: 16 nm; BET specific surface area value: 204.3 m 2 /g; light fastness ⁇ E*: 5.36) while operating an edge runner, and the resultant mixture was mixed and stirred for 30 min under a linear load of 588 N/cm (60 Kg/cm) at a stirring speed of 22 rpm.
  • the organic pigment G (kind: phthalocyanine-based pigment; average particle diameter: 100 nm; BET specific surface area value: 67.3 m 2 /g; L* value: 29.77; a* value: ⁇ 15.30; b* value: ⁇ 1.12; C* value: 15.34; light fastness ⁇ E*: 8.06; ⁇ potential in a water-based system: ⁇ 3.6 mV; ⁇ potential in a solvent-based system: ⁇ 1.5 mV) was added to the above-obtained mixture for 30 min while operating the edge runner, and the resultant mixture was mixed and stirred for 100 min under a linear load of 392 N/cm (40 Kg/cm) at a stirring speed of 22 rpm, thereby allowing the organic pigment G to adhere onto the methylhydrogenpolysiloxane coating layer formed on the respective silica particles. Then, the obtained particles were dried at 80° C. for 60 min using a dryer, thereby obtaining composite
  • the thus obtained composite particles 1 had an average primary particle diameter of 20 nm, a BET specific surface area value of 78.6 m 2 /g, an L* value of 30.22, an a* value of ⁇ 14.92, a b* value of ⁇ 1.10, a C* value of 14.96 and a degree of desorption of organic pigment of Rank 4.
  • the composite particles 1 had a tinting strength of 93%, a light fastness ⁇ E* of 2.12, a ⁇ potential in a water-based system of ⁇ 22.7 mV, a potential in a solvent-based system of ⁇ 6.6 mV, and a coating amount of methylhydrogenpolysiloxane of 0.53% by weight (calculated as C), and that the amount of the organic pigment G adhered was 18.15% by weight (calculated as C; corresponding to 100 parts by weight based on 100 parts by weight of the silica particles).
  • a 3-L beaker was charged with 200 g of the above-obtained composite particles (composite particles 1) and 2 L of a 0.65 mol/L sodium hydroxide aqueous solution (0.2 time a theoretical amount thereof capable of dissolving the silica particles as core particles and the surface-modifying agent) to prepare a solution having a pH value of 13.1.
  • the resultant solution was stirred at 60° C. for 30 min and then subjected to filtration to separate a solid therefrom. The thus separated solid was washed with water and then dried, thereby obtaining colored composite microparticles.
  • the thus obtained colored composite microparticles had an average primary particle diameter of 15 nm, a number-average particle diameter of 22 nm, a volume-average particle diameter of 78 nm, and a BET specific surface area value of 83.6 m 2 /g. Also, the amount of silica enclosed in the colored composite microparticles was 1.06% by weight (calculated as Si).
  • the hue values of the colored composite microparticles the L* value thereof was 31.33; the a* value thereof was ⁇ 14.29; the b* value thereof was ⁇ 1.10; and the C* value thereof was 14.33.
  • the colored composite microparticles had a tinting strength of 105%, a light fastness ⁇ E* of 3.56, a ⁇ potential in a water-based system of ⁇ 13.8 mV, and a ⁇ potential in a solvent-based system of ⁇ 6.4 mV.
  • Example 1-1 15 parts by weight of the colored composite microparticles obtained in Example 1-1 and 100 parts by weight of water were added together with 100 g of 0.35 mm ⁇ glass beads into a 140-mL glass bottle, and then dispersed for 2 hr by a paint shaker, thereby obtaining a water-based dispersion.
  • the resultant water-based dispersion containing the colored composite microparticles had a number-average dispersed particle diameter of 19 nm, a volume-average dispersed particle diameter of 42 nm, a dispersion stability of Rank 5, a rate of change in viscosity of 4.8% and a specific absorption coefficient ⁇ w of 2.46.
  • Example 1-1 15 parts by weight of the colored composite microparticles obtained in Example 1-1 and 100 parts by weight of PGMEA were added together with 100 g of 0.35 mm ⁇ glass beads into a 140-mL glass bottle, and then dispersed for 2 hr by a paint shaker, thereby obtaining a solvent-based dispersion.
  • the resultant solvent-based dispersion containing the colored composite microparticles had a number-average dispersed particle diameter of 19 nm, a volume-average dispersed particle diameter of 48 nm, a dispersion stability of Rank 5, a rate of change in viscosity of 4.7% and a specific absorption coefficient ⁇ w of 2.44.
  • the composite particles, the colored composite microparticles, the water-based dispersion and the solvent-based dispersion were produced.
  • the essential production conditions as well as various properties of the obtained composite particles, colored composite microparticles, water-based dispersion and solvent-based dispersion are shown below.
  • silica particles 1 to 4 having properties shown in Table 1 below were prepared.
  • organic pigments having properties shown in Table 2 below were prepared.
  • Example 1-1 The same procedure as defined in Example 1-1 was conducted except that kinds of composite particles, pH values of dissolution solutions used upon alkali dissolution, ratio of actual amount of alkali added to theoretical amount thereof, and treating temperature and time of the alkali dissolution, were changed variously, thereby obtaining colored composite microparticles. Meanwhile, the concentration (g/100 mL) of the composite particles means a weight (g) of the composite particles based on 100 mL of the dissolution solution. Also, in Example 1-2, freeze-drying was conducted as the drying step. The essential production conditions are shown in Table 5, and various properties of the obtained colored composite microparticles are shown in Table 6.
  • the organic pigment Y (kind: quinophthalone-based pigment; average primary particle diameter: 252 nm; BET specific surface area value: 27.9 m 2 /g; L* value: 84.21; a* value: 3.00; b* value: 91.31; C* value: 91.36; light fastness ⁇ E*: 7.22; ⁇ potential in a water-based system: ⁇ 3.1 mV; ⁇ potential in a solvent-based system: ⁇ 1.4 mV) was charged together with 6 g of xylene and 2 kg of 8 mm ⁇ steel beads into a dry-type attritor, and the attritor was operated at 80° C. for 2 hr at a rotating speed of 300 rpm, thereby obtaining a quinophthalone pigment.
  • Table 6 properties of the thus obtained quinophthalone pigment are shown in Table 6.
  • Example 2-1 The same procedure as defined in Example 2-1 was conducted except that kinds and amounts of colored composite microparticles blended were changed variously, thereby obtaining water-based dispersions.
  • the essential production conditions and various properties of the obtained water-based dispersions are shown in Table 7.
  • Example 3-1 The same procedure as defined in Example 3-1 was conducted except that kinds and amounts of colored composite microparticles blended were changed variously, thereby obtaining solvent-based dispersions.
  • the essential production conditions and various properties of the obtained solvent-based dispersions are shown in Table 8.
  • methylhydrogenpolysiloxane (tradename: “TSF484”, produced by GE TOSHIBA SILICONE CO., LTD.) was added to 3.5 kg of silica 1 (average particle diameter of primary particles: 16 nm; BET specific surface area value: 204.3 m 2 /g; light fastness ⁇ E*: 5.36; heat resistance ⁇ E*: 3.46) while operating an edge runner, and the resultant mixture was mixed and stirred for 30 minutes under a linear load of 588 N/cm (60 Kg/cm) at a stirring speed of 22 rpm.
  • the thus obtained composite particles 6 had an average primary particle diameter of 23 nm, a BET specific surface area value of 76.9 m 2 /g, an L* value of 30.36, an a* value of ⁇ 14.79, a b* value of ⁇ 1.12, a C* value of 14.83 and a degree of desorption of organic pigment of Rank 4.
  • the composite particles 6 had a tinting strength of 96%, a light fastness ⁇ E* of 2.28, a heat resistance ⁇ E* of 2.49, a ⁇ potential in a water-based system of ⁇ 23.0 mV, a ⁇ potential in a solvent-based system of ⁇ 6.6 mV, and a coating amount of methylhydrogenpolysiloxane of 0.53% by weight (calculated as C).
  • the amount of the organic pigment G adhered onto the composite particles 6 was 24.06% by weight (calculated as C; corresponding to 200 parts by weight based on 100 parts by weight of the silica particles).
  • organic pigment B kind: phthalocyanine-based pigment; average primary particle diameter: 80 nm; BET specific surface area value: 87.9 m 2 /g; L* value: 23.04; a* value: 5.99; b* value: ⁇ 13.16; C* value: 14.46; light fastness ⁇ E*: 8.83; heat resistance ⁇ E*: 9.04; ⁇ potential in a water-based system: ⁇ 2.9 mV; ⁇ potential in a solvent-based system: ⁇ 1.3 mV) was used, thereby producing composite particles 7.
  • organic pigment B kind: phthalocyanine-based pigment; average primary particle diameter: 80 nm; BET specific surface area value: 87.9 m 2 /g; L* value: 23.04; a* value: 5.99; b* value: ⁇ 13.16; C* value: 14.46; light fastness ⁇ E*: 8.83; heat resistance ⁇ E*: 9.04; ⁇ potential in a water-based system: ⁇
  • the composite particles 7 had a tinting strength of 96%, a light fastness ⁇ E* of 2.64, a heat resistance ⁇ E* of 2.75, a ⁇ potential in a water-based system of ⁇ 22.2 mV, a ⁇ potential in a solvent-based system of ⁇ 6.0 mV, and a coating amount of methylhydrogenpolysiloxane of 0.54% by weight (calculated as C).
  • the amount of the organic pigment B adhered onto the composite particles 7 was 44.68% by weight (calculated as C; corresponding to 200 parts by weight based on 100 parts by weight of the silica particles).
  • organic pigment R kind: diketopyrrolopyrrole-based pigment; average primary particle diameter: 130 nm; BET specific surface area value: 82.4 m 2 /g; L* value: 38.42; a* value: 43.20; b* value: 23.36; C* value: 49.11; light fastness ⁇ E*: 7.92; heat resistance ⁇ E*: 7.28; ⁇ potential in a water-based system: ⁇ 2.9 mV; ⁇ potential in a solvent-based system: ⁇ 1.2 mV) was used, thereby producing composite particles 8.
  • the organic pigment R kind: diketopyrrolopyrrole-based pigment; average primary particle diameter: 130 nm; BET specific surface area value: 82.4 m 2 /g; L* value: 38.42; a* value: 43.20; b* value: 23.36; C* value: 49.11; light fastness ⁇ E*: 7.92; heat resistance ⁇ E*: 7.28; ⁇ potential in a
  • the thus obtained composite particles 8 had an average primary particle diameter of 24 nm, a BET specific surface area value of 85.6 m 2 /g, an L* value of 48.46, an a* value of 48.10, a b* value of 22.39, a C* value of 53.06 and a degree of desorption of organic pigment of Rank 4.
  • the composite particles 8 had a tinting strength of 96%, a light fastness ⁇ E* of 2.48, a heat resistance ⁇ E* of 2.26, a ⁇ potential in a water-based system of ⁇ 20.5 mV, a ⁇ potential in a solvent-based system of ⁇ 6.3 mV, and a coating amount of methylhydrogenpolysiloxane of 0.53% by weight (calculated as C).
  • the amount of the organic pigment R adhered onto the composite particles 8 was 40.38% by weight (calculated as C; corresponding to 200 parts by weight based on 100 parts by weight of the silica particles).
  • a 3-L beaker was charged with 200 g of the above-obtained composite particles (composite particles 6) and 2 L of a 0.44 mol/L sodium hydroxide aqueous solution (0.2 time a theoretical amount thereof capable of dissolving the silica particles as core particles and the surface-modifying agent) to prepare a solution having a pH value of 13.2.
  • the resultant solution was stirred at 60° C. for 30 min and then subjected to filtration to separate a solid therefrom. The thus separated solid was washed with water and then dried, thereby obtaining a colorant (G) for color filters.
  • the thus obtained colorant (G) for color filters had an average primary particle diameter of 16 nm, a number-average particle diameter of 23 nm, a volume-average particle diameter of 74 nm, a BET specific surface area value of 84.7 m 2 /g. Also, the amount of silica enclosed in the colorant (G) for color filters was 1.09% by weight (calculated as Si). As to the hue values of the colorant (G) for color filters, the L* value thereof was 31.38; the a* value thereof was ⁇ 14.29; the b* value thereof was ⁇ 1.11; and the C* value thereof was 14.33.
  • the colorant (G) for color filters had a tinting strength of 106%, a light fastness ⁇ E* of 3.50, a heat resistance ⁇ E* of 3.69, a ⁇ potential in a water-based system of ⁇ 13.9 mV, and a ⁇ potential in a solvent-based system of ⁇ 6.5 mV.
  • the thus obtained colorant (B) for color filters had an average primary particle diameter of 16 nm, a number-average particle diameter of 27 nm, a volume-average particle diameter of 78 nm, a BET specific surface area value of 95.2 m 2 /g. Also, the amount of silica enclosed in the colorant (B) for color filters was 0.96% by weight (calculated as Si). As to the hue values of the colorant (B) for color filters, the L* value thereof was 26.49; the a* value thereof was 5.83; the b* value thereof was ⁇ 12.88; and the C* value thereof was 14.14.
  • the colorant (B) for color filters had a tinting strength of 106%, a light fastness ⁇ E* of 3.62, a heat resistance ⁇ E* of 3.94, a ⁇ potential in a water-based system of ⁇ 12.9 mV, and a ⁇ potential in a solvent-based system of ⁇ 6.1 mV.
  • the thus obtained colorant (R) for color filters had an average primary particle diameter of 17 nm, a number-average particle diameter of 31 nm, a volume-average particle diameter of 84 nm, a BET specific surface area value of 88.6 m 2 /g. Also, the amount of silica enclosed in the colorant (R) for color filters was 1.14% by weight (calculated as Si). As to the hue values of the colorant (R) for color filters, the L* value thereof was 40.19; the a* value thereof was 43.26; the b* value thereof was 23.51; and the C* value thereof was 49.24.
  • the colorant (R) for color filters had a tinting strength of 105%, a light fastness ⁇ E* of 3.24, a heat resistance ⁇ E* of 3.42, a ⁇ potential in a water-based system of ⁇ 14.0 mV, and a ⁇ potential in a solvent-based system of ⁇ 6.6 mV.
  • the thus obtained coloring composition (I-G) for color filters had a number-average dispersed particle diameter of 18 nm, a volume-average dispersed particle diameter of 42 nm, a rate of change in viscosity of 4.0%, a light transmittance at a wavelength of 530 nm of 84.6% and a specific absorption coefficient ⁇ w (on the weight basis) at a wavelength of 650 nm of 2.45.
  • Example 5-1 The same procedure as defined in Example 5-1 was conducted except that the colorant (B) for color filters was used as a colorant, thereby obtaining a coloring composition (I-B) for color filters.
  • the thus obtained coloring composition (I-B) for color filters had a number-average dispersed particle diameter of 22 nm, a volume-average dispersed particle diameter of 37 nm, a rate of change in viscosity of 4.7%, a light transmittance at a wavelength of 460 nm of 82.8% and a specific absorption coefficient ⁇ w (on the weight basis) at a wavelength of 610 nm of 2.35.
  • Example 5-1 The same procedure as defined in Example 5-1 was conducted except that the colorant (R) for color filters was used as a colorant, thereby obtaining a coloring composition (I-R) for color filters.
  • the thus obtained coloring composition (I-R) for color filters had a number-average dispersed particle diameter of 28 nm, a volume-average dispersed particle diameter of 45 nm, a rate of change in viscosity of 4.9%, a light transmittance at a wavelength of 620 nm of 89.6% and a specific absorption coefficient ⁇ w (on the weight basis) at a wavelength of 550 nm of 1.94.
  • the thus obtained coloring composition (II-G) for color filters had a number-average dispersed particle diameter of 19 nm, a volume-average dispersed particle diameter of 44 nm, a viscosity of 16.6 mPa ⁇ s, a rate of change in viscosity of 3.9%, and a specific absorption coefficient ⁇ w (on the weight basis) at a wavelength of 650 nm of 2.56.
  • the obtained coloring composition (II-G) for color filters was applied onto a clear base film to form a coating layer having a thickness of 150 ⁇ m (6 mil), and then dried, thereby obtaining a colored transparent film (II-G) for color filters.
  • the resultant colored transparent film (II-G) for color filters exhibited a chromaticity represented by a x value of 0.2754, a y value of 0.3878 and a Y value of 70.21, and had a light fastness ⁇ E* of 3.32 and a heat resistance ⁇ E* of 3.51, as well as a light transmittance at a wavelength of 530 nm of 92.6% and a specific absorption coefficient ⁇ w (on the weight basis) at a wavelength of 650 nm of 2.47.
  • the thus obtained coloring composition (II-B) for color filters had a number-average dispersed particle diameter of 23 nm, a volume-average dispersed particle diameter of 38 nm, a viscosity of 17.9 mPa ⁇ s, a rate of change in viscosity of 4.6%, and a specific absorption coefficient ⁇ w (on the weight basis) at a wavelength of 610 nm of 2.47.
  • the obtained coloring composition (II-B) for color filters was applied onto a clear base film to form a coating layer having a thickness of 150 ⁇ m (6 mil), and then dried, thereby obtaining a colored transparent film (II-B) for color filters.
  • the resultant colored transparent film (II-B) for color filters exhibited a chromaticity represented by a x value of 0.1475, a y value of 0.2182 and a Y value of 29.33, and had a light fastness ⁇ E* of 3.42 and a heat resistance ⁇ E* of 3.74, as well as a light transmittance at a wavelength of 460 nm of 91.8% and a specific absorption coefficient ⁇ w (on the weight basis) at a wavelength of 610 nm of 2.36.
  • Example 6-1 The same procedure as defined in Example 6-1 was conducted except that the coloring composition (I-R) for color filters was used as a coloring composition, thereby obtaining a coloring composition (II-R) for color filters.
  • the thus obtained coloring composition (II-R) for color filters had a number-average dispersed particle diameter of 30 nm, a volume-average dispersed particle diameter of 55 nm, a viscosity of 19.4 mPa ⁇ s; a rate of change in viscosity of 4.7%, and a specific absorption coefficient ⁇ w (on the weight basis) at a wavelength of 550 nm of 2.01.
  • the obtained coloring composition (II-R) for color filters was applied onto a clear base film to form a coating layer having a thickness of 150 ⁇ m (6 mil), and then dried, thereby obtaining a colored transparent film (II-R) for color filters.
  • the resultant colored transparent film (II-R) for color filters exhibited a chromaticity represented by a x value of 0.5846, a y value of 0.3398 and a Y value of 23.24, and had a light fastness ⁇ E* of 3.18 and a heat resistance ⁇ E* of 3.36, as well as a light transmittance at a wavelength of 620 nm of 96.6% and a specific absorption coefficient ⁇ w (on the weight basis) at a wavelength of 550 nm of 1.95.
  • the coloring composition (II-G) for color filters 500.0 parts by weight of the coloring composition (II-G) for color filters (obtained in Example 6-1), 100.0 parts by weight of dipentaerythritol pentaacrylate and 5.0 parts by weight of 2-(4-methoxy- ⁇ -styryl)-bis(4,6-trichloromethyl)-s-triazine were mixed and dispersed together for 2 hr using a beads mill. The resultant kneaded material was filtered through a 1 ⁇ m glass filter, thereby obtaining a coloring composition (III-G) for color filters.
  • the thus obtained coloring composition (III-G) for color filters had a number-average dispersed particle diameter of 17 nm, a volume-average dispersed particle diameter of 40 nm, a viscosity of 16.8 mPa ⁇ s, a rate of change in viscosity of 3.9%, and a specific absorption coefficient ⁇ w (on the weight basis) at a wavelength of 650 nm of 2.55.
  • the obtained coloring composition (III-G) for color filters was applied onto a clear base film to form a coating layer having a thickness of 150 ⁇ m (6 mil), and then dried, thereby obtaining a colored transparent film (III-G) for color filters.
  • the resultant colored transparent film (III-G) for color filters exhibited a chromaticity represented by a x value of 0.2755, a y value of 0.3877 and a Y value of 70.36, and had a light fastness ⁇ E* of 3.30 and a heat resistance ⁇ E* of 3.49, as well as a light transmittance at a wavelength of 530 nm of 93.1% and a specific absorption coefficient ⁇ w (on the weight basis) at a wavelength of 650 nm of 2.49.
  • Example 7-1 The same procedure as defined in Example 7-1 was conducted except that the coloring composition (II-B) for color filters was used as a coloring composition, thereby obtaining a coloring composition (III-B) for color filters.
  • the thus obtained coloring composition (III-B) for color filters had a number-average dispersed particle diameter of 21 nm, a volume-average dispersed particle diameter of 35 nm, a viscosity of 17.8 mPa ⁇ s, a rate of change in viscosity of 4.6%, and a specific absorption coefficient ⁇ w (on the weight basis) at a wavelength of 610 nm of 2.45.
  • the obtained coloring composition (III-B) for color filters was applied onto a clear base film to form a coating layer having a thickness of 150 ⁇ m (6 mil), and then dried, thereby obtaining a colored transparent film (III-B) for color filters.
  • the resultant colored transparent film (III-B) for color filters exhibited a chromaticity represented by a x value of 0.1476, a y value of 0.2181 and a Y value of 29.42, and had a light fastness ⁇ E* of 3.41 and a heat resistance ⁇ E* of 3.71, as well as a light transmittance at a wavelength of 460 nm of 92.4% and a specific absorption coefficient ⁇ w (on the weight basis) at a wavelength of 610 nm of 2.38.
  • Example 7-1 The same procedure as defined in Example 7-1 was conducted except that the coloring composition (II-R) for color filters was used as a coloring composition, thereby obtaining a coloring composition (III-R) for color filters.
  • the thus obtained coloring composition (III-R) for color filters had a number-average dispersed particle diameter of 26 nm, a volume-average dispersed particle diameter of 51 nm, a viscosity of 19.6 mPa ⁇ s, a rate of change in viscosity of 4.8%, and a specific absorption coefficient ⁇ w (on the weight basis) at a wavelength of 550 nm of 2.00.
  • the obtained coloring composition (III-R) for color filters was applied onto a clear base film to form a coating layer having a thickness of 150 ⁇ m (6 mil), and then dried, thereby obtaining a colored transparent film (III-R) for color filters.
  • the resultant colored transparent film (III-R) for color filters exhibited a chromaticity represented by a x value of 0.5848, a y value of 0.3399 and a Y value of 23.29, and had a light fastness ⁇ E* of 3.14 and a heat resistance ⁇ E* of 3.35, as well as a light transmittance at a wavelength of 620 nm of 97.1% and a specific absorption coefficient ⁇ w (on the weight basis) at a wavelength of 550 nm of 1.97.
  • the thus obtained coloring composition (IV-G) for color filters had a number-average dispersed particle diameter of 18 nm, a volume-average dispersed particle diameter of 41 nm, a viscosity of 17.2 mPa ⁇ s, a rate of change in viscosity of 4.0%, and a specific absorption coefficient ⁇ w (on the weight basis) at a wavelength of 650 nm of 2.53.
  • the obtained coloring composition (IV-G) for color filters was applied onto a clear base film to form a coating layer having a thickness of 150 ⁇ m (6 mil), and then dried, thereby obtaining a colored transparent film (IV-G) for color filters.
  • the resultant colored transparent film (IV-G) for color filters exhibited a chromaticity represented by a x value of 0.2752, a y value of 0.3877 and a Y value of 70.41, and had a light fastness ⁇ E* of 3.28 and a heat resistance ⁇ E* of 3.45, as well as a light transmittance at a wavelength of 530 nm of 93.2% and a specific absorption coefficient ⁇ w (on the weight basis) at a wavelength of 650 nm of 2.48.
  • Example 8-1 The same procedure as defined in Example 8-1 was conducted except that the coloring composition (II-B) for color filters was used as a coloring composition, thereby obtaining a coloring composition (IV-B) for color filters.
  • the thus obtained coloring composition (IV-B) for color filters had a number-average dispersed particle diameter of 21 nm, a volume-average dispersed particle diameter of 36 nm, a viscosity of 18.1 mPa ⁇ s, a rate of change in viscosity of 4.6%, and a specific absorption coefficient ⁇ w (on the weight basis) at a wavelength of 610 nm of 2.44.
  • the obtained coloring composition (IV-B) for color filters was applied onto a clear base film to form a coating layer having a thickness of 150 ⁇ m (6 mil), and then dried, thereby obtaining a colored transparent film (IV-B) for color filters.
  • the resultant colored transparent film (IV-B) for color filters exhibited a chromaticity represented by a x value of 0.1475, a y value of 0.2179 and a Y value of 29.44, and had a light fastness ⁇ E* of 3.38 and a heat resistance ⁇ E* of 3.66, as well as a light transmittance at a wavelength of 460 nm of 92.5% and a specific absorption coefficient ⁇ w (on the weight basis) at a wavelength of 610 nm of 2.38.
  • Example 8-1 The same procedure as defined in Example 8-1 was conducted except that the coloring composition (II-R) for color filters was used as a coloring composition, thereby obtaining a coloring composition (IV-R) for color filters.
  • the thus obtained coloring composition (IV-R) for color filters had a number-average dispersed particle diameter of 27 nm, a volume-average dispersed particle diameter of 52 nm, a viscosity of 20.1 mPa ⁇ s, a rate of change in viscosity of 4.9%, and a specific absorption coefficient ⁇ w (on the weight basis) at a wavelength of 550 nm of 2.01.
  • the obtained coloring composition (IV-R) for color filters was applied onto a clear base film to form a coating layer having a thickness of 150 ⁇ m (6 mil), and then dried, thereby obtaining a colored transparent film (IV-R) for color filters.
  • the resultant colored transparent film (IV-R) for color filters exhibited a chromaticity represented by a x value of 0.5846, a y value of 0.3402 and a Y value of 23.29, and had a light fastness ⁇ E* of 3.15 and a heat resistance ⁇ E* of 3.34, as well as a light transmittance at a wavelength of 620 nm of 97.3% and a specific absorption coefficient ⁇ w (on the weight basis) at a wavelength of 550 nm of 1.96.
  • the coloring composition (II-G) for color filters (obtained in Example 6-1) was spin-coated onto a non-alkali glass plate having a thickness of 0.7 mm on which a black matrix resin pattern layer having a thickness of 1.0 ⁇ m was formed, and then pre-baked at 90° C. for 4 min using a hot plate. Then, a positive-type photoresist was applied onto the resultant coating layer of the coloring composition and then dried under heating at 80° C. for 20 min to form a resist film thereon.
  • the obtained laminate was exposed to light with a luminous intensity of 400 mJ/cm 2 using a 2.50 kW ultrahigh-pressure mercury lamp, and then developed with an aqueous sodium carbonate solution, followed by removing the unnecessary photoresist layer therefrom with methyl cellosolve acetate. Further, the resultant colored film was heat-treated at 250° C. for 30 min in a nitrogen atmosphere to obtain a patterned green-colored film.
  • the resultant color filter (I) had a light transmittance at 530 nm of 92.0%, a light transmittance at 460 nm of 91.4%, a light transmittance at 620 nm of 96.2%, and a contrast of 1700.
  • the coloring composition (III-G) for color filters (obtained in Example 7-1) was spin-coated onto a non-alkali glass plate having a thickness of 0.7 mm on which a black matrix resin pattern layer having a thickness of 1.0 ⁇ m was formed, and then pre-baked at 90° C. for 4 min using a hot plate. After forming a photoresist layer on the resultant coating layer, the obtained laminate was exposed to pattern light with a luminous intensity of 400 mJ/cm 2 using a 2.50 kW ultrahigh-pressure mercury lamp, and then developed with an aqueous sodium carbonate solution, followed by removing the unnecessary photoresist layer therefrom. Further, the resultant colored film was heat-treated at 250° C. for 30 min in a nitrogen atmosphere to obtain a patterned green-colored film.
  • the resultant color filter (II) had a light transmittance at 530 nm of 92.4%, a light transmittance at 460 nm of 91.6%, a light transmittance at 620 nm of 96.4%, and a contrast of 1720.
  • the resultant color filter (III) had a light transmittance at 530 nm of 92.6%, a light transmittance at 460 nm of 91.7%, a light transmittance at 620 nm of 96.6%, and a contrast of 1730.
  • the composite particles, the colorant for color filters, the coloring composition for color filters and the color filter were produced.
  • the essential production conditions as well as various properties of the obtained composite particles, colorant for color filters, coloring composition for color filters and color filter are shown below.
  • silica particles 1 to 4 having properties shown in Table 1 were prepared.
  • organic pigments having properties shown in Table 2 were prepared.
  • Example 4-1 The same procedure as defined in Example 4-1 was conducted except that kinds of composite particles, pH values of dissolution solutions used upon alkali dissolution, ratio of actual amount of alkali added to theoretical amount thereof, and treating temperature and time of the alkali dissolution, were changed variously, thereby obtaining colorants for color filters.
  • concentration mL) of the composite particles means a weight (g) of the composite particles based on 100 mL of the dissolution solution.
  • freeze-drying was conducted as the drying step.
  • the essential production conditions are shown in Table 11, and various properties of the obtained colorants for color filters are shown in Table 12.
  • a dioxazine violet pigment in the form of an acicular crystal produced by an acid slurry treatment 36 parts of the organic pigment B (kind: phthalocyanine-based pigment; average primary particle diameter: 80 nm; BET specific surface area value: 87.9 m 2 /g; L* value: 23.04; a* value: 5.99; b* value: ⁇ 13.16; C* value: 14.46; light fastness ⁇ E*: 8.83; heat resistance ⁇ E*: 9.04; ⁇ potential in a water-based system: ⁇ 2.9 mV; ⁇ potential in a solvent-based system: ⁇ 1.3 mV), 400 parts of pulverized sodium chloride, and 80 parts of diethyleneglycol, were charged into a double arm-type kneader, and then kneaded together at a temperature of 100 to 110° C.
  • the organic pigment B kind: phthalocyanine-based pigment; average primary particle diameter: 80 nm; BET specific surface area value
  • the obtained kneaded material was taken out and added into 100 parts of a 1% hydrochloric acid aqueous solution maintained at 80° C., and after stirring for 1 hr, the obtained mixture was subjected to filtration, washing with hot water, drying and pulverization, thereby obtaining a phthalocyanine blue pigment.
  • the organic pigment G (kind: phthalocyanine-based pigment; average primary particle diameter: 100 nm; BET specific surface area value: 67.3 m 2 /g; L* value: 29.77; a* value: ⁇ 15.30; b* value: ⁇ 1.12; C* value: 15.34; light fastness ⁇ E*: 8.06; heat resistance ⁇ E*: 7.46; ⁇ potential in a water-based system: ⁇ 3.6 mV; ⁇ potential in a solvent-based system: ⁇ 1.5 mV), 400 parts of pulverized sodium chloride, and 80 parts of diethyleneglycol, were charged into a double arm-type kneader, and then kneaded together at a temperature of 100 to 110° C.
  • the organic pigment G kind: phthalocyanine-based pigment; average primary particle diameter: 100 nm; BET specific surface area value: 67.3 m 2 /g; L* value: 29.77; a* value: ⁇ 15.30;
  • the obtained kneaded material was taken out and added into 100 parts of a 1% hydrochloric acid aqueous solution maintained at 80° C., and after stirring for 1 hr, the obtained mixture was subjected to filtration, washing with hot water, drying and pulverization, thereby obtaining a phthalocyanine green pigment.
  • the obtained kneaded material was taken out and added into 100 parts of a 1% hydrochloric acid aqueous solution maintained at 80° C., and after stirring for 1 hr, the obtained mixture was subjected to filtration, washing with hot water, drying and pulverization, thereby obtaining a diketopyrrolopyrrole pigment.
  • Example 5-1 The same procedure as defined in Example 5-1 was conducted except that kinds of colorants for color filters, kinds and amounts of dispersants blended, and amounts of solvents blended, were changed variously, thereby obtaining coloring compositions (I) for color filters.
  • the essential production conditions are shown in Tables 13 and 14, and various properties of the obtained coloring compositions (I) for color filters are shown in Tables 15 and 16.
  • Example 5-1 Modified 30.0 PGMEA 270.0 acrylic block copolymer
  • Example 5-2 Modified 30.0 PGMEA 270.0 acrylic block copolymer
  • Example 5-3 Modified 30.0 PGMEA 270.0 acrylic block copolymer
  • Example 5-4 Modified 30.0 PGMEA 270.0 acrylic block copolymer
  • Example 5-5 Modified 30.0 PGMEA 270.0 acrylic block copolymer
  • Example 5-6 Basic comb- 20.0 PGMEA 280.0 shaped polymer
  • Example 5-8 Phenol ether- 25.0 PGMEA 275.0 based nonionic surfactant
  • Example 5-9 Modified 20.0 PGMEA 100.0 acrylic block copolymer
  • Example 6-1 The same procedure as defined in Example 6-1 was conducted except that kinds of coloring compositions (I) for color filters and amounts of resins blended therein were changed variously, thereby obtaining coloring compositions (II) for color filters.
  • the essential production conditions are shown in Table 17, various properties of the obtained coloring compositions (II) for color filters are shown in Tables 18 and 19, and various properties of the colored transparent films (II) for color filters obtained by coating the coloring compositions (II) for color filters are shown in Tables 20 and 21.
  • Coloring composition for color filters
  • Coloring composition (I) Resin Amount Amount blended blended (wt (wt Kind part) kind part)
  • Example 6-1 Example 400.0 MMA/MA 100.0 5-1 copolymer*
  • Example 6-2 Example 400.0 MMA/MA 100.0 5-2 copolymer*
  • Example 6-3 Example 400.0 MMA/MA 100.0 5-3 copolymer*
  • Example 6-4 Example 400.0 MMA/MA 100.0 5-4 copolymer*
  • Example 6-5 Example 400.0 MMA/MA 100.0 5-5 copolymer*
  • Example 6-6 Example 400.0 MMA/MA 90.0 5-6 copolymer*
  • Example 6-8 Example 400.0 MMA/MA 70.0 5-8 copolymer*
  • Example 220.0 MMA/MA 100.0 5-9 copolymer* Comparative Examples Comparative Comparative 400.0 MMA/MA 100.0 Example 6-1 Example 5-1 copolymer* Comparative Comparative 400.0 MMA/MA 100.0 Example 6-2 Example 5-2
  • Example 7-1 The same procedure as defined in Example 7-1 was conducted except that kinds of coloring compositions (II) for color filters and amounts of polymerization initiators blended therein were changed variously, thereby obtaining coloring compositions (III) for color filters.
  • the essential production conditions are shown in Table 22, various properties of the obtained coloring compositions (III) for color filters are shown in Tables 23 and 24, and various properties of the colored transparent films (III) for color filters obtained by coating the coloring compositions (III) for color filters are shown in Tables 25 and 26.
  • Coloring composition (II) Polyfunctional monomer Amount Amount blended blended (wt. (wt. Examples kind part) kind part)
  • Example 7-1 Example 500.0 Dipentaerythritol 100.0 6-1 pentaacrylate
  • Example 7-2 Example 500.0 Dipentaerythritol 100.0 6-2 pentaacrylate
  • Example 7-3 Example 500.0 Dipentaerythritol 100.0 6-3 pentaacrylate
  • Example 7-5 Example 500.0 Dipentaerythritol 100.0 6-5 pentaacrylate
  • Example 7-6 Example 490.0 Dipentaerythritol 100.0 6-6 pentaacrylate
  • Example 7-7 Example 480.0 Dipentaerythritol 100.0 6-7 pentaacrylate
  • Example 7-8 Example 470.0 Dipentaerythritol 100.0 6-8 pentaacrylate
  • Example 7-9 Example 320.0 Dipentaerythri
  • Example 7-1 2-(4-methoxy- ⁇ -styryl)-bis(4,6- 5.0 trichloromethyl)-s-triazine
  • Example 7-2 2-(4-methoxy- ⁇ -styryl)-bis(4,6- 5.0 trichloromethyl)-s-triazine
  • Example 7-3 2-(4-methoxy- ⁇ -styryl)-bis(4,6- 5.0 trichloromethyl)-s-triazine
  • Example 7-4 2-(4-methoxy- ⁇ -styryl)-bis(4,6- 5.0 trichloromethyl)-s-triazine
  • Example 7-5 2-(4-methoxy- ⁇ -styryl)-bis(4,6- 5.0 trichloromethyl)-s-triazine
  • Example 7-6 2-(4-methoxy- ⁇ -styryl)-bis(4,6- 4.5 trichloromethyl)-s-triazine
  • Example 9-1 The same procedure as defined in Example 9-1 was conducted except that kinds of coloring compositions for color filters were changed variously, thereby obtaining color filters (I).
  • the essential production conditions and various properties of the obtained color filters are shown in Tables 32 and 33.
  • Example 9-13 The same procedure as defined in Example 9-13 was conducted except that kinds of coloring compositions for color filters were changed variously, thereby obtaining color filters (III).
  • the essential production conditions and various properties of the obtained color filters are shown in Tables 32 and 33.
  • the organic pigment B (kind: phthalocyanine-based pigment; average particle diameter: 80 nm; BET specific surface area value: 87.9 m 2 /g; geometrical standard deviation value: 2.15; L* value: 23.04; a* value: 5.99; b* value: ⁇ 13.16; C* value: 14.46; light fastness ⁇ E*: 8.83; ⁇ potential: ⁇ 2.9 mV) was added to the above-obtained mixture for 30 min while operating the edge runner, and the resultant mixture was mixed and stirred for 120 min under a linear load of 392 N/cm at a stirring speed of 22 rpm to allow the organic pigment B to adhere onto the methylhydrogenpolysiloxane coating layer formed on the respective silica particles, thereby obtaining composite particles 13.
  • the organic pigment B kind: phthalocyanine-based pigment; average particle diameter: 80 nm; BET specific surface area value: 87.9 m 2 /g; geometrical standard deviation value: 2.15
  • the composite particles 13 exhibited a degree of desorption of organic pigment of Rank 4, a tinting strength of 93%, a light fastness ⁇ E* of 2.15, a ⁇ potential of ⁇ 22.8 mV, and a coating amount of methylhydrogenpolysiloxane of 0.53% by weight (calculated as C).
  • the amount of the organic pigment B adhered onto the composite particles 13 was 33.19% by weight (calculated as C; corresponding to about 100 parts by weight based on 100 parts by weight of the silica particles).
  • the amount of silica enclosed in the thus obtained colorant for inks for ink-jet printing was 1.04% by weight (calculated as Si), and the colorant for inks for ink-jet-printing had an average primary particle diameter of 15 nm, a BET specific surface area value of 82.4 m 2 /g, a number-average particle diameter of 21 nm, a volume-average particle diameter of 75 nm and a geometrical standard deviation value of 1.31.
  • the hue values of the colorant for inks for ink-jet-printing the L* value thereof was 25.39; the a* value thereof was ⁇ 5.90; the b* value thereof was ⁇ 12.95, and the C* value thereof was 14.23.
  • the colorant for inks for ink-jet printing had a tinting strength of 105%, a light fastness ⁇ E* of 3.54, and a ⁇ potential of ⁇ 13.6 mV.
  • the resultant ink for ink-jet printing had a number-average dispersed particle diameter of 18 nm, a volume-average dispersed particle diameter of 51 nm, a dispersion stability (as visual evaluation) of Rank 5, and a rate of change in number-average dispersed particle diameter of 6.8%.
  • the hue values of the ink for ink-jet printing the L* value thereof was 27.68; the a* value thereof was 5.42; the b* value thereof was ⁇ 13.04; and the C* value thereof was 14.12.
  • the ink for ink-jet printing had a specific absorption coefficient ⁇ w of 2.28, a light fastness ⁇ E* of 1.73, an anti-clogging property of Rank 5.
  • the composite particles, the colorants for inks for ink-jet printing, and the inks for ink-jet printing were respectively produced.
  • the essential production conditions as well as various properties of the obtained composite particles, colorants for inks for ink-jet printing, and inks for ink-jet printing, are shown below.
  • the silica particles 1 and 2 having properties shown in Table 1 were prepared.
  • Example 10-1 The same procedure as defined in Example 10-1 was conducted except that kinds of composite particles, pH values of dissolution solutions used upon alkali dissolution, ratio of actual amount of alkali added to theoretical amount thereof and treating temperature and time, were changed variously, thereby obtaining colorants for inks for ink-jet printing. Meanwhile, the concentration (g/100 mL) of the composite particles means a weight (g) of the composite particles based on 100 mL of the dissolution solution. Also, in Example 10-2, freeze-drying was conducted as the drying step. The essential production conditions are shown in Table 36, and various properties of the obtained colorants for inks for ink-jet printing are shown in Table 37.
  • Example 10-1 Composite particles 10.0 13
  • Example 10-2 Composite particles 10.0 13
  • Example 10-3 Composite particles 10.0 13
  • Example 10-4 Composite particles 10.0 13
  • Example 10-5 Composite particles 10.0 14
  • Example 10-6 Composite particles 10.0 15
  • Example 10-7 Composite particles 10.0 16 Comparative Composite particles 10.0
  • Example 10-3 13 Production of colorant for inks for ink- jet printing Dissolution solution Ratio to Examples and theoretical Comparative pH amount Examples
  • Example 10-1 Sodium hydroxide 13.1 0.20
  • Example 10-2 Sodium hydroxide 13.1 0.20
  • Example 10-3 Sodium hydroxide 13.1 0.20
  • Example 10-4 Sodium hydroxide 13.7 0.89
  • Example 10-5 Sodium hydroxide 13.2 0.40
  • Example 10-6 Sodium hydroxide 13.4 0.70
  • Example 10-7 Potassium hydroxide 13.0 0.10 Comparative Sodium hydroxide 13.9 1.50
  • Example 10-1 Composite particles 10.0 13
  • Example 10-1 Properties of colorant for inks for ink-jet printing Average BET primary specific Examples and particle surface Comparative Si content diameter area value Examples (wt %) (nm) (m 2 /g) Example 10-1 1.04 15 82.4 Example 10-2 1.04 14 84.7 Example 10-3 0.90 16 81.5 Example 10-4 0.09 13 88.0 Example 10-5 1.01 17 74.3 Example 10-6 0.20 17 67.1 Example 10-7 2.15 20 62.9 Comparative 0.00 12 89.2 Example 10-1 Comparative 27.36 20 57.8 Example 10-2 Comparative 30.22 19 60.6
  • Example 10-3 Properties of colorant for inks for ink-jet printing Number- Volume- Geometrical average average standard Examples and particle particle deviation Comparative diameter diameter value Examples (nm) (nm) (—) Example 10-1 21 75 1.31 Example 10-2 20 66 1.29 Example 10-3 23 83 1.32 Example 10-4 40 115 1.35 Example 10-5 22 80 1.33 Example 10-6 28 92 1.34 Example 10-7 21 79 1.46 Comparative 48 158 1.42 Example 10-1
  • Example 11-1 The same procedure as defined in Example 11-1 was conducted except that kinds of colorants for inks for ink-jet printing were changed variously, thereby obtaining inks for ink-jet printing.
  • the essential production conditions are shown in Table 38, and various properties of the obtained inks for ink-jet printing are shown in Tables 39 and 40.

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JP2006172462A JP5093442B2 (ja) 2006-06-22 2006-06-22 カラーフィルター用着色材及び該カラーフィルター用着色材を含有するカラーフィルター用着色組成物並びにカラーフィルター
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TWI553351B (zh) * 2012-07-25 2016-10-11 Ｌｇ化學股份有限公司 使用相變化油墨之撓性濾光片基板及其製造方法
CN114231146A (zh) * 2021-12-22 2022-03-25 广东溢达纺织有限公司 浸胶浆料、浸胶绳头及其制备方法
US11680175B2 (en) * 2018-12-03 2023-06-20 Viavi Solutions Inc. Composition including a color shifting pigment and a color filter

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JP5239143B2 (ja) * 2006-09-29 2013-07-17 大日本印刷株式会社 カラーフィルターの製造方法、並びに液晶表示装置の製造方法
CN109844035A (zh) * 2016-10-07 2019-06-04 M技术株式会社 有机颜料组合物的制造方法、涂膜的制造方法及涂膜的亮度的评价方法
KR20190040465A (ko) * 2017-10-10 2019-04-18 도다 고교 가부시끼가이샤 아닐린 블랙 그리고 해당 아닐린 블랙을 사용한 수지 조성물 및 분산체
CN109762374B (zh) * 2019-01-03 2021-05-25 深圳市绚图新材科技有限公司 一种可直接用于注塑的彩色铝颜料及其制备方法

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TWI553351B (zh) * 2012-07-25 2016-10-11 Ｌｇ化學股份有限公司 使用相變化油墨之撓性濾光片基板及其製造方法
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CN114231146A (zh) * 2021-12-22 2022-03-25 广东溢达纺织有限公司 浸胶浆料、浸胶绳头及其制备方法

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EP1930380A1 (en) 2008-06-11
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WO2007029694A1 (ja) 2007-03-15
KR101274297B1 (ko) 2013-06-13

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