WO2003000805A1 - Procede de production d'une dispersion aqueuse de pigment et dispersion aqueuse de pigment obtenue au moyen dudit procede - Google Patents
Procede de production d'une dispersion aqueuse de pigment et dispersion aqueuse de pigment obtenue au moyen dudit procede Download PDFInfo
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- WO2003000805A1 WO2003000805A1 PCT/JP2002/006380 JP0206380W WO03000805A1 WO 2003000805 A1 WO2003000805 A1 WO 2003000805A1 JP 0206380 W JP0206380 W JP 0206380W WO 03000805 A1 WO03000805 A1 WO 03000805A1
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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
- 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
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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
- 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
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01F—MIXING, e.g. DISSOLVING, EMULSIFYING OR DISPERSING
- B01F25/00—Flow mixers; Mixers for falling materials, e.g. solid particles
- B01F25/20—Jet mixers, i.e. mixers using high-speed fluid streams
- B01F25/21—Jet mixers, i.e. mixers using high-speed fluid streams with submerged injectors, e.g. nozzles, for injecting high-pressure jets into a large volume or into mixing chambers
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
- B41F—PRINTING MACHINES OR PRESSES
- B41F17/00—Printing apparatus or machines of special types or for particular purposes, not otherwise provided for
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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
- C09C3/00—Treatment in general of inorganic materials, other than fibrous fillers, to enhance their pigmenting or filling properties
- C09C3/04—Physical treatment, e.g. grinding, treatment with ultrasonic vibrations
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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
- 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
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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
- 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
- C09D11/02—Printing inks
- C09D11/03—Printing inks characterised by features other than the chemical nature of the binder
- C09D11/037—Printing inks characterised by features other than the chemical nature of the binder characterised by the pigment
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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
- 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
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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
- 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
- C09D11/324—Inkjet printing inks characterised by colouring agents containing carbon black
- C09D11/326—Inkjet printing inks characterised by colouring agents containing carbon black characterised by the pigment dispersant
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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
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/41—Organic pigments; Organic dyes
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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
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
- C09K23/017—Mixtures of compounds
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01F—MIXING, e.g. DISSOLVING, EMULSIFYING OR DISPERSING
- B01F2215/00—Auxiliary or complementary information in relation with mixing
- B01F2215/04—Technical information in relation with mixing
- B01F2215/0413—Numerical information
- B01F2215/0418—Geometrical information
- B01F2215/0431—Numerical size values, e.g. diameter of a hole or conduit, area, volume, length, width, or ratios thereof
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01F—MIXING, e.g. DISSOLVING, EMULSIFYING OR DISPERSING
- B01F2215/00—Auxiliary or complementary information in relation with mixing
- B01F2215/04—Technical information in relation with mixing
- B01F2215/0413—Numerical information
- B01F2215/0436—Operational information
- B01F2215/0481—Numerical speed values
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01F—MIXING, e.g. DISSOLVING, EMULSIFYING OR DISPERSING
- B01F23/00—Mixing according to the phases to be mixed, e.g. dispersing or emulsifying
- B01F23/50—Mixing liquids with solids
- B01F23/56—Mixing liquids with solids by introducing solids in liquids, e.g. dispersing or dissolving
Definitions
- the present invention relates to a method for producing an aqueous pigment dispersion and an aqueous pigment dispersion obtained from the method.
- the present invention relates to a method for producing an aqueous pigment dispersion, and can be more suitably used particularly for an ink jet recording liquid or a colorant composition for a color filter, and is also applicable to fields such as printing inks.
- the present invention relates to a method for producing a pigment dispersion in which a pigment is dispersed to a finer particle diameter and which has extremely high dispersion stability over time.
- Aqueous pigment dispersions have long been used as base compositions for colorants in the fields of paints and printing inks. Recently, however, aqueous pigment dispersions have recently been used in extremely new applications such as inkjet recording liquids and colorant compositions for color filters. Applications are beginning to expand to fields where clear images are required.
- the required level of coloring is so high that it is incomparable to printing inks.
- the ink jet recording system has a mechanism to eject ink from fine nozzles, and color filters require highly uniform film thickness with high precision.
- the composition is required to have flow properties very close to Newtonian flow.
- mill-type dispersers that use collisions between media, collisions between pigment dispersions and walls of dispersing devices (liquid-to-wall collisions), collisions between pigment dispersions (A method of dispersing a pigment exclusively by an impact force using a high-pressure emulsifier using liquid-liquid collision) has been used.
- Japanese Patent Application Laid-Open No. 5-271600 discloses a technique using a mill-type dispersing machine such as a pole mill and a bead mill.
- 10—3 6 7 3 8 discloses a technique using a high-pressure emulsifier such as an Almizer (Sugino Machine Co., Ltd., one-liquid collision between ultrahigh-speed fluids by improving the high-pressure emulsifier described above). ing.
- a high-pressure emulsifier such as an Almizer (Sugino Machine Co., Ltd., one-liquid collision between ultrahigh-speed fluids by improving the high-pressure emulsifier described above).
- An object of the present invention is to provide a method for producing a pigment dispersion in which the pigment is dispersed to a finer particle diameter and which has extremely high pigment dispersion stability over time, which is applicable to the field.
- pigment dispersers currently in use cannot disperse pigment particles stably enough to be used in inkjet recording liquids and colorant compositions for color filters. Have to be used.
- the present invention provides: (1) a mixture comprising a pigment, at least one selected from the group consisting of a polymer emulsifier having an HLB of 5 or more and a surfactant having an HLB of 5 or more, and an aqueous medium. After passing through an orifice having no curved portion and no bent portion under pressure, the mixture is further discharged into a previously outflowing mixture that is retained in a hollow member having a larger diameter than the orifice. And a method for producing an aqueous pigment dispersion in which a pigment is dispersed in an aqueous medium. The present invention also relates to (2) the method for producing an aqueous pigment dispersion according to (1), wherein the polymer emulsifier has a weight average molecular weight of 100 to 100,000.
- the present invention also provides (3) a polymer emulsifier having a hydrophobic portion and a hydrophilic portion in the molecule as the polymer emulsifier, wherein the hydrophobic portion is a saturated cyclic hydrocarbon group. And at least one selected from the group consisting of an unsaturated cyclic hydrocarbon group and an alkyl group having 4 or more carbon atoms, and the hydrophilic portion is selected from the group consisting of a carboxyl group, a sulfonic group and a phosphate group.
- the present invention relates to a method for producing at least one aqueous pigment dispersion according to the above (1) or (2).
- the present invention also provides (4) a hydrophobic group-containing radical polymerizable monomer and a hydrophilic group-containing radical polymerizable monomer as the polymer emulsifier, in an amount satisfying the following conditions A and B: Using a copolymer obtained by copolymerizing with the above, or using a hydrophobic polymerizable monomer containing a hydrophobic group, a radical polymerizable monomer containing a hydrophilic group, and another radical polymerizable monomer.
- Condition A The total amount of the hydrophobic group-containing radically polymerizable monomer is 1 0-70 mole 0/0 relative to the total radical polymerizable monomers.
- Condition B The total amount of the radical-polymerizable monomer containing a hydrophilic group is determined so that the acid value of the copolymer obtained by copolymerizing all the radical-polymerizable monomers is 50 to 25 Omg KOH / g. You.
- the present invention also provides (5) a method comprising using, as the polymer emulsifier, a copolymer obtained by polymerizing a radical-polymerizable monomer containing a hydrophobic group and a radical-polymerizable monomer containing a hydrophilic group. Or a copolymer obtained by polymerizing a radical-polymerizable monomer containing a hydrophobic group, a radical-polymerizable monomer containing a hydrophilic group, and another radical-polymerizable monomer.
- the radical-polymerizable monomer having a functional group has styrene, a styrene derivative, an aromatic (meth) acrylic monomer, an alicyclic (meth) acrylic monomer, and an alkyl group having 4 or more carbon atoms ( At least one member selected from the group of (meth) acrylic monomers, and the above-mentioned hydrophilic group-containing radical polymerizable monomer includes (meth) acrylic acid, itaconic acid, crotonic acid and ( Anhydrous) selected from the group of maleic acid
- the present invention relates to a method for producing an aqueous pigment dispersion according to any one of the above (1) to (4), which is at least one kind.
- the present invention also provides (6) the aqueous pigment dispersion of (1) or (2), wherein at least one polymer emulsifier selected from the group of polyurethane compounds and polyester compounds is used as the polymer emulsifier. And a method for producing the same.
- the present invention provides (7) a surfactant having a saturated cyclic hydrocarbon group or unsaturated cyclic hydrocarbon group and a hydrophilic portion in the molecule thereof as the surfactant.
- the present invention relates to a method for producing an aqueous pigment dispersion.
- the present invention also provides (8) the aqueous pigment according to any one of the above (1) to (7), wherein the aqueous medium contains the polymer emulsifier and Z or a surfactant in an amount equal to or more than a micelle critical concentration.
- the present invention relates to a method for producing a dispersion.
- the present invention also relates to (9) the method for producing an aqueous pigment dispersion according to any one of the above (1) to (8), wherein a surface-treated pigment is used as the pigment.
- the present invention provides (10) the aqueous pigment dispersion according to any one of the above (1) to (9), wherein the mixture is passed through an orifice at a speed of 100 to LOOO mZ sec. And a method for producing the same.
- the present invention also relates to (11) the method for producing an aqueous pigment dispersion according to any one of (1) to (10), wherein an orifice having a diameter of 0.01 to 1.5 mm is used as the orifice.
- the present invention also provides (12) a pigment, which has previously passed through the orifice and stayed in the hollow member, and at least one selected from the group consisting of the polymer emulsifier and the surfactant, The flow toward the outlet of the mixture including the medium and the pigment that passes through the orifice later, at least one selected from the group of the polymer emulsifier and the surfactant, and the discharge of the mixture including the aqueous medium
- the present invention relates to the method for producing an aqueous pigment dispersion according to any one of the above (1) to (11), wherein the pigment is dispersed in such a manner as to make a countercurrent flow in the hollow member with respect to the flow in the direction.
- the present invention provides (13) the production of the aqueous pigment dispersion according to any one of (1) to (12) above, wherein the mixture is premixed with a non-media type mixing apparatus and then passed through the orifice. About the method.
- the present invention also relates to (14) an aqueous pigment dispersion obtained by the method for producing an aqueous pigment dispersion according to any one of the above (1) to (13).
- At least one selected from the group consisting of a, b, c, and d means “a, b, b, and 3 (c + d). And at least one selected from the group consisting of a, b, c, and d means “1 (a + b + at least one selected from the group of c + d).
- a mixture comprising a pigment, at least one selected from the group of a polymer emulsifier having an HLB of 5 or more and a surfactant having an HLB of 5 or more, and an aqueous medium It means "a mixture comprising (1) a pigment, (2) at least one selected from the group of (polymer emulsifier having an HLB of 5 or more + surfactant having an HLB of 5 or more), and (3) an aqueous medium.”
- the hydrophobic portion is at least one selected from the group consisting of a saturated cyclic hydrocarbon group, an unsaturated cyclic hydrocarbon group, and an alkyl group having 4 or more carbon atoms.
- the above-mentioned hydrophobic part is (1) (saturated cyclic hydrocarbon group + unsaturated cyclic Hydrocarbon group + alkyl group having 4 or more carbon atoms).
- Pigments are formed in the form of fine primary particles during production, but form aggregates during processes such as drying, so in order to obtain a clear hue and fluidity, they must be dispersed again in fine particles. No.
- the dispersion is performed under a gentle condition over a long period of time with a force slightly larger than the force (cohesion force) for forming the aggregates of the pigment, the pigment will be evenly reduced to near the primary particle diameter. It is possible to disperse.
- the force is smaller than the cohesive force, the undispersed particles (coarse particles) remain without being able to disperse to the next particle.
- the primary particles are further crushed and excessively crushed. Particles (finer particles) will be generated. Such coarse particles and fine particles cause the following problems.
- the reason why the pigment having a higher specific gravity than the dispersion medium does not settle and can maintain the dispersed state in the dispersion medium is due to the collision energy (energy causing Brownian motion) of the dispersion medium molecules on the pigment surface. It is. However, coarse particles have a small ratio of surface area to weight (specific surface area), so that the ratio of energy against gravity is small, and sedimentation is likely to occur.
- a media-collision-type mill-liquid-wall collision or liquid-liquid collision-type high-pressure emulsifying machine or the like which collides a spherical media.
- a media collision type mill since the collision between media occurs at a point, the pigment existing near the collision point receives a strong impact, and the pigment existing far from the collision point has a weak impact. Will receive.
- a liquid-wall (liquid) collision type high-pressure emulsifier it is impossible to make the pigment uniformly collide with the wall of the device or with the pigments.
- the pigment that has received a weak dispersing force remains undispersed and remains as coarse particles, while the pigment that has received a strong dispersing force is excessively pulverized into fine particles, and a mixture of coarse particles and fine particles has a particle size of It is considered to be a pigment dispersion having a nonuniform particle size with a wide distribution.
- the pigment is dispersed by causing a mixture of the pigment, the specific polymer emulsifier and / or the surfactant and the aqueous medium to pass through the orifice at a high speed, and further ejecting the mixture into the hollow member. It is characterized by the following.
- the pigment dispersing method of the present invention provides the optimal dispersing force according to the specific strength. (Cohesion between primary particles ⁇ dispersion power and crushing strength of primary particles) can be uniformly applied to the pigment. With such characteristics, the pigment dispersion method of the present invention enables the pigment to be uniformly dispersed to the primary particles without generating excessively pulverized particles or undispersed particles.
- a function of adsorbing on the hydrophobic surface of the pigment (hydrophobic portion) and an aqueous medium and hydration A compound having an HLB of 5 or more, which has a function (hydrophilic portion), as a dispersant.
- the pigment dispersing apparatus used in the present invention was originally developed as an emulsifier, the ability of the HLB to form micelles of compounds having 5 or more compounds is extremely high. It is believed that stable micelles are formed in the aqueous medium.
- pigment particles finely dispersed by an ordinary media-type disperser for example, particles having an average particle diameter of 100 nm or less (0.1 ⁇ m) are newly added by the dispersion of the pigment.
- the resulting hydrophobic surface causes agglomeration and the dispersion stability is reduced.
- the pigment particles finely dispersed by the pigment dispersing apparatus used in the present invention are immediately contained in the micelle, It is considered that by covering the surface, a pigment dispersion having excellent dispersion stability can be obtained without causing aggregation over time.
- thermodynamic stabilizing effect is further enhanced, and the dispersion stability of the pigment is also improved. It will be expensive. As described above, it is extremely difficult to produce a pigment dispersion capable of stably maintaining a fine and uniform particle size distribution of pigment particles, which is indispensable for obtaining a clear hue and good fluidity, in an aqueous system.
- the aim was to make the force applied to the pigment uniform and, at the same time, to use the micelle formation of the polymer emulsifier and surfactant.
- the present invention has established a production method thereof. -The present invention will be described more specifically.
- the pigments that can be used in the present invention are various inorganic pigments and organic pigments generally used in printing ink paints.
- the inorganic pigments include titanium oxide, red iron oxide, antimony red, cadmium yellow, kono noreto blue, and navy blue.
- pigments such as ultramarine, ultramarine, carbon black, and graphite; and extenders such as calcium carbonate, kaolin, clay, barium sulfate, aluminum hydroxide, and talc.
- examples of the organic pigment include a soluble azo pigment, an insoluble azo pigment, an azo lake pigment, a condensed azo pigment, a copper phthalocyanine pigment, and a condensed polycyclic pigment.
- these pigments have been previously subjected to a salt milling treatment or various surface treatments using a resin, a surfactant or a pigment derivative, and further mixed with a resin material to form a color chip. May be used.
- the content of these pigments is preferably about 0.5 to 50% by mass based on the total amount of the pigment dispersion.
- HLB is selected from a group of a polymer emulsifier having a hydrophilic portion and a hydrophobic portion in the molecule and having a HLB of 5 or more and a surfactant having an HLB power of 5 or more. At least one compound is used.
- HLB represents the balance (hydrophi 1 e-1 ipophi 1 eba 1 ance) between the hydrophilic part and the lipophilic part of the molecule, which is used in the field of surfactants. It can be said that the larger the value, the higher the hydrophilicity.
- a compound having an HLB of 5 or more means that the HLB calculated by the experimental method described below is 5 or more, in addition to the compound having an HLB of 5 or more when the following Griffin formula is applied. Means the equivalent. [Darifin formula]
- HLB (100/5)
- X weight of hydrophilic group Z (weight of hydrophilic group + weight of hydrophobic group)
- the hydrophilic group include acid groups such as carboxyl group, sulfonic acid group and phosphoric acid group, and amino group ammonium salt.
- a basic group such as a metal complex, a hydroxyl group, an ethylene oxide group, and the like, and a portion other than the hydrophilic group is a hydrophobic group.
- the alkylene oxide group having 3 or more carbon atoms becomes a hydrophobic group.
- the calculated value obtained from the Griffin equation based on the weight of the »group and the weight of the hydrophobic group can be directly applied as an HLB value.
- the hydrophilicity of the hydrophilic group is generally much larger than that of the non-ionic surfactant, and the hydrophilicity per unit weight varies depending on the type of the hydrophilic group. Therefore, it is said that there is no way to calculate HLB (for example, "Introduction to New Surfactants” (Takehiko Fujimoto, published by Sanyo Chemical Industries, Ltd.)).
- HLB for ionic surfactants in which the hydrophilicity of the hydrophilic group is much greater than that of the nonionic, at least one that has a numerical value greater than 5 when applied to the above-mentioned HLB equation of griffin is at least It can be said that HLB is 5 or more.
- the surfactant required in the present invention is the emulsifying property of a surfactant having an HLB of 5 or more
- the emulsifying property corresponding to an HLB of 5 or more can be obtained by this method of experimentally determining HLB. It is also possible to use ionic surfactants that have been found to have.
- HLB is used for surfactants that can disperse at least in the form of milk, in addition to transparently dissolving, translucent or transparent dispersion. Is 5 or more, and can be used in the present invention.
- the polymer emulsifier usable in the present invention includes a hydrophobic part and a hydrophilic part in the molecule. Based on the above-mentioned relationship, Griffin's formula or HLB obtained experimentally is used. Any of the above polymer compounds can be used without limitation.
- Either ionic or nonionic polymeric emulsifiers can be used.
- a saturated cyclic hydrocarbon group, an unsaturated cyclic hydrocarbon group, or an alkyl group having 4 or more carbon atoms can be used. It is preferable that at least one selected from the group is contained in the molecule, and the hydrophilic portion includes a carboxyl group, a sulfonic acid group, a phosphoric acid group (these are preferred acid groups), an amino group and It is preferably an ionic polymer emulsifier containing at least one selected from the group of ammonium salts (these are preferred basic groups) in the molecule.
- polymer emulsifier having these preferred embodiments include, for example, a radical polymerizable monomer having a hydrophobic portion in the molecule, a radical polymerizable monomer having the hydrophilic portion in the molecule, A polyurethane compound synthesized from the above-described reaction component having a hydrophobic portion in the molecule and the reaction component having the hydrophilic portion in the molecule, a polyester compound, Examples thereof include polyamide compounds.
- Suitable radically polymerizable monomers having the above-mentioned hydrophobic moiety in the molecule to be used for obtaining the above-mentioned copolymer compound include cyclohexyl (meth) phthalate and derivatives thereof.
- Alicyclic (meta) acrylates bulcyclohexa Radical polymerizable monomers having a saturated cyclic hydrocarbon group such as butane and its derivatives, a-Phenylacrylic acid and its derivatives, j3-Phenylacrylic acid and its derivatives, Benzyl (meth) acrylate and its derivatives
- Aromatic acrylic monomers such as naphthyl (meth) acrylate and its derivatives, aromatic radical polymerizable monomers such as styrene and its derivatives, vinyl naphthalene and its derivatives, and butyl (meth) phthalate, Hexyl (meth) acrylate, octyl (meth) acrylate, nonyl (meth) acrylate, decyl (meth) acrylate, dodecyl (meth) acrylate, lauryl (meth) acrylate, stearyl (meth) acrylate, etc.
- preferred radically polymerizable monomers having a hydrophilic portion in the molecule include: (meth) acrylic acid, crotonic acid, anhydrous maleic acid, and the like.
- Carboxyl group-containing unsaturated monomers such as maleic acid and its monoalkyl ester compound, itaconic acid and its monoalkyl ester compound, citraconic acid and its monoalkyl ester compound, 2-acrylamide 2-methyl-1- Propanesulfonic acid, 2-methacrylamide 2-methyl-11-propanesulfonic acid, sulfonic acid-containing unsaturated monomers such as styrenesulfonic acid, acid phosphonyl (meth) acrylate, acid phospho-ruethyl (meth) acrylate, etc. And a phosphoric acid group-containing unsaturated monomer.
- unsaturated monomers containing a basic group include ⁇ -alkylaminoalkyl (meth) acrylate, ⁇ -alkylaminoalkyl (meth) acrylamide, ⁇ , ⁇ -dialkylaminoalkyl (meth) acrylate , , ⁇ -dialkylaminoalkyl (meth) acrylamide and other amino group-containing unsaturated monomers, ⁇ , ⁇ , ⁇ N- (2-Acryloyloxy) ethylammonium chloride, N, N, N-triethyl-N— (2-Acryloyloxy) ethylammonium chloride, N, N, N— Tolytyl-N— (2-Atari mouth inoleoxy) ethylammonium chloride, N, N, N—Trimethyl-1-N— (3-Atariloyloxy) propylammonium chloride, N, N, N—Trietyl-1-
- copolymerizable radical polymerizable monomers can also be used, such as ethylene, propylene, (meth) acrylic acid alkyl ester having an alkyl group having 3 or less carbon atoms, and (meth) acrylic acid. Hydroxyalkyl ester, (meth) atarylamide, acrylonitrile, ketone compound having a vinyl group and an alkyl group having 3 or less carbon atoms, ether compound having a butyl group and an alkyl group having 3 or less carbon atoms Objects and the like.
- a polymer emulsifier obtained by copolymerizing such a material is an anion-based emulsifier containing at least one kind of an acidic group selected from the group consisting of a hydroxyl group, a sulfonic acid group and a phosphoric acid group as a hydrophilic group.
- the HLB is calculated by the Griffin formula directly. Anything above can be used.
- a milky dispersion, a translucent to transparent dispersion, or a transparent dispersion in water in the presence of a basic compound or an acidic compound described later. What can be dissolved can be used as those of 5 or more HLB. If the obtained copolymer has an acid value of approximately 50 to 25 Omg KOH / g or an amine value of approximately 10 to 10 Omg KOH / g, the copolymer has the above-mentioned state in water, and has a polymer emulsifier. It can be used as
- preferred hydrophobic group-containing radical polymerizable monomers in the present invention include alicyclic acrylic monomers and aromatic acrylic monomers. Monomer, styrene and its derivatives, and (meth) acrylic monomers having an alkyl group having 4 or more carbon atoms.
- preferred radically polymerizable monomers containing a hydrophilic biogroup are unsaturated monomers containing an acid group. Monomer, especially a carboxyl group-containing unsaturated monomer.
- an urethane prepolymer is synthesized by reacting an organic diisocyanate compound and a polymer diol compound, and then a chain extender and a reaction stop.
- Polyurethane resin obtained by reacting an agent, for example, a material having a hydrophobic portion in a molecule includes toluylene dicysinate, xylylene diisocyanate, diphenylmethane diisocyanate, and tetramethylxylylene.
- Aromatic diisocyanate compounds such as diisocyanate, alicyclic diisocyanate compounds such as isophorone diisocyanate and cyclohexenediisocyanate, and high molecular polyesters obtained by reacting phthalic acid with glycol Diol compounds, aromatic chain extenders such as bisphenol, An alicyclic chain extender such as isophorone diamine can be used.
- Examples of the material having a hydrophilic portion in the molecule include a lipoxyl group-containing high molecular weight polyester diol compound obtained by reacting a lipoxyl group-containing diol such as dimethyl alcohol propionic acid with a dibasic acid, and polyalkylene dalicol.
- polyester / resin having a hydrophobic part and a hydrophilic part in a molecule
- a polycarboxylic acid and a polyhydric alcohol are reacted under an excess condition of a carboxyl group.
- the obtained carboxyl group-containing polyester resin using an aromatic or alicyclic compound is used as one of the polycarboxylic acids and the polyhydric alcohols. Can be mentioned.
- examples of the polyvalent carboxylic acids include aromatic compounds such as terephthalic acid, isophthalic acid, orthophthalic acid, 1,5-naphthalenedicarboxylic acid, 2,6-naphthalenedicarboxylic acid, diphenic acid and p-phenic acid.
- polyvalent alcohols include alicyclic compounds such as aromatic compounds such as para-xylene glycol, meta-xylene glycol, and onolexylene glycol, and 1,4-phenylene glycol.
- Aliphatic compounds such as cyclohexanediol, 1,4-cyclohexanedimethanole, spiroglyconolle, hydrogenated bisphenanol A, tricyclodecane, tricyclodecanedimethanol, etc., ethylene glycolone, propylene glycolone, and butylene glycol
- dialcohols such as cornole and polyethylene glycol
- trihydric or higher polyhydric alcohols such as trimethylolonethane, glycerin, and pentaerythritol.
- dicarboxylic acids and dialcohols are first reacted in excess of hydroxyl groups, and then reacted with trivalent or higher polycarboxylic acids such as trimellitic acid, trimesic acid, and pyromellitic acid at the molecular terminals.
- trivalent or higher polycarboxylic acids such as trimellitic acid, trimesic acid, and pyromellitic acid at the molecular terminals.
- a polyester resin having an appropriate acid value can also be obtained.
- sulfone group-containing polyester resin examples include sulfoterephthalic acid, 5-snolephoisophthalic acid, 4-snolefophthalic acid, 4-snolefonaphthalene_2,7_dicarboxylic acid, and 5 [4-sulfophenoxy] isophthalic acid And the like, and sulfonate-containing polyester resins obtained using a sulfonate-containing dicarboxylic acid or a metal salt or an ammonium salt thereof, and a polyhydric alcohol.
- the phosphoric acid group-containing polyester resin can be obtained by using at least one of phosphoric acid, pyrophosphoric acid, polyphosphoric acid and phosphoric acid in the reaction process of the above polyhydric alcohol compound and polycarboxylic acid compound.
- Polyurethane resin and polyester resin obtained by synthesizing these materials are Anionic polymer emulsifier containing at least one acidic group of carboxyl group, sulfonic acid group, and phosphoric acid group as a hydrophilic group in the polymer.First, an HLB of 5 or more is calculated directly by the Griffin formula. Is available.
- the acid value of the above polyurethane resin or polyester resin is approximately 10 to 100 mgKOH / g, it has the above-mentioned state in water and can be used as a polymer emulsifier.
- a water-soluble polymer compound having a hydroxyl group or a nonionic nitrogen-containing group in the molecule can be used.
- a water-soluble polymer compound having a hydroxyl group or a nonionic nitrogen-containing group in the molecule can be used.
- polyvinyl alcohol, polyvinyl pyrrolidone, polyacrylamide And water-soluble cellulose and the like as a nonionic polymer emulsifier.
- the weight average molecular weight of the above-mentioned polymer emulsifier is about 1000 to 1,000,000, preferably about 5,000 to 100,000.
- the weight average molecular weight of the polymer emulsifier is smaller than the above range, the effect of stably dispersing the fine particles of the pigment is reduced.
- the weight average molecular weight is larger, it is difficult to keep the viscosity of the aqueous pigment dispersion stable for a long time. Becomes
- polymeric emulsifiers are generally capable of forming a pigment-containing micelle by including a pigment in a micelle composed of one to several molecules.
- Such pigment-containing micelles are expected to form a thick adsorption layer of the polymer emulsifier on the surface of the pigment by the interaction between the pigment and the polymer emulsifier, and to expect a high effect by stabilizing the dispersion of the pigment in an aqueous medium. is there.
- a surfactant having an HLB of 5 or more can be used alone or in combination with the above-mentioned polymer emulsifier.
- Various aionic surfactants that form salts with metals such as metal salts of sulfates of higher alcohols such as 40), and various cationic interfaces such as compounds that contain amino groups, compounds that contain ammonium salts, and compounds that form metal complexes. Activators are available.
- nonionic or ionic surfactants having a saturated cyclic hydrocarbon group or an unsaturated cyclic hydrocarbon group and a hydrophilic portion in the molecule are preferred in terms of dispersion stability of the pigment. Can be suitably used.
- polymer emulsifiers and Z or surfactant are preferably contained in the aqueous medium in an amount equal to or higher than the critical micelle concentration, and more preferably as the pigment content increases, The content is preferably 0.1 to 40.0% by mass based on the total amount of the pigment dispersion (mixture), and about 5 to 100% by mass based on the pigment.
- the aqueous medium used in the present invention may be water alone, but may be a basic compound necessary for emulsifying the anionic polymer emulsifier, or a basic compound necessary for emulsifying the cationic polymer emulsifier. It may contain an acidic compound and, if necessary, a water-miscible organic solvent.
- the basic compounds usable in the present invention include: inorganic basic compounds such as ammonium hydroxide, organic basic compounds such as triethylamine, monoethanolamine, and triethanolamine; and acidic compounds. Hydrochloric acid, sulfuric acid, acetic acid and the like can be mentioned. Form may be in a range to stabilize, but is usually in the 8 0-1 2 0 mole 0/0 about neutralization of polymeric emulsifiers suitable amount.
- organic solvent to be added as needed examples include lower alcohols such as methanol, ethanol, and propanol; (poly) alkylene glycols such as (poly) ethylene glycol and (poly) propylene daricol; and alkyl ethers thereof.
- aqueous pigment dispersion of the present invention various additives such as a pigment dispersing aid, a viscosity modifier, and an antifoaming agent can be added as needed.
- Such a method is an example of a preferred embodiment of the present invention, and the present invention is not limited to this.
- the pigment dispersing machine used in the present invention is an ultrahigh-speed emulsifying apparatus in which a fluid pressurizing section 1, an orifice 2, and a hollow member 3 are configured in parallel as shown in the schematic diagram of FIG.
- a fluid such as a solid-liquid mixture or a liquid-liquid mixture is introduced into the pressurizing section 1 from a hopper (not shown) using a pressurizing pump (not shown).
- the fluid is pressurized to 5 ⁇ 10 3 to 3.2 ⁇ 10 5 kPa so that the fluid has an orifice having a diameter of 0.01 to 1.5 mm without a curved portion and a curved portion.
- the velocity at which the fluid is passed is preferably 100 to 100 Om / sec, more preferably 300 to 700 m // sec, and is uniform and fine solid.
- the diameter of the orifice and the speed of passing through the orifice in order to obtain a one-part liquid mixture or a one-part liquid mixture, it is possible to generate an optimal stress applied to the fluid in the orifice.
- the high-speed jet flow of the fluid generated by the orifice 2 is jetted into the hollow member 3, and the fluid is jetted first and the fluid is caused by the shear stress generated by the speed difference with the fluid staying in the hollow member 3. It is emulsified or dispersed. Therefore, the hollow member is preferably cylindrical.
- the ratio of the orifice to the pipe diameter of the hollow member is set to 1: (2 to 50), more preferably 1: (5 to 1), so that an appropriate speed difference for the shear stress to act between the fluids is generated. 0), and it is desirable to have a sufficient volume so that the high-speed jet stream does not collide with the facing surface of the hollow member with a strong force.
- this pigment disperser a method of discharging the obtained emulsion or dispersion of the fluid from an outlet 4 provided on a wall facing the orifice of the hollow member, and as shown in the schematic diagram of FIG.
- the fluid After the fluid passes through the orifice 6 3 ⁇ 4r at high speed from the pressurizing section 5, the fluid further reciprocates between the orifice side of the hollow member 7 and the wall facing the orifice, and flows out of the discharge port 8 provided near the orifice side.
- Both methods are available. Among them, in the method of making one round trip between the orifice side and the wall facing the air (Fig. 2), the flow of the mixture that has passed through the orifice P ⁇ toward the discharge port 8 retained in the hollow member first (return path), and The flow in the discharge direction of the mixture passing from the orifice to the orifice (outgoing path) forms a countercurrent flow, which can generate a higher shear force. Further, it is possible to control the flow rate of the mixture in the hollow member by applying a back pressure from the outlet 4 or 8.
- the above-mentioned pigment, the surfactant such as a polymer emulsifier, and the aqueous medium are mixed with a high-speed mixer or a high-pressure homogenizer. Premix processing is performed using a pre-dispersing machine that does not use media.
- the premixed mixture flows into the pressurizing section by the pressurizing pump of the dispersing machine, and preferably, the speed of the mixture passing through the orifice is 400 to 100 Om / sec.
- the pigment is finely dispersed by the stress applied when the pigment flows out into the hollow member, and at the same time, the micelle of the polymer emulsifier is formed, and the pigment fine particles are contained in the micelle.
- the viscosity is preferably less than 1 Pasec, more preferably less than 0.5 Pa'sec, and more preferably less than 0.5 Pa'sec.
- the premix mixture was adjusted to 0.2 less than P a ⁇ S ec, 8 X 1 0 4 ⁇ 2 X 1 0 5 k P a degree pressurized, 4 the orifice 0 0 ⁇ 8 0 Om / It is passed at a flow rate of sec to apply shear stress and stress due to pressure change to the pigment.
- the pressure applied to the premitttus mixture is adjusted so that the stress applied to the pigment is between the cohesion between the primary particles of the pigment and the crushing strength of the primary particles.
- the jet stream of the premix mixture passed through the orifice is discharged into the premix mixture retained in the hollow member and discharged earlier. If it is controlled so that the speed of collision with the wall facing the orifice is substantially zero, a shear force is generated according to the speed difference, and the pigment is further subjected to dispersion.
- 3 ⁇ 4 and stays in the hollow member, and the premix mixture that later passes through the orifice form countercurrent. In this case, the stress applied in the hollow member becomes higher, which is advantageous for dispersing a pigment having a stronger cohesive force of primary particles.
- the pigment dispersion obtained by dispersing the pigment by such a method coarse particles may be further removed by a post-treatment such as a centrifugal separation treatment and a filter treatment of the pigment dispersion.
- a post-treatment such as a centrifugal separation treatment and a filter treatment of the pigment dispersion.
- the pigment is dispersed by a uniform and controlled stress, and the pigment is formed into fine primary particles or fine primary particles without generating excessively pulverized particles or undispersed particles.
- finely dispersed pigment particles do not cause aggregation over time, and an aqueous pigment dispersion with extremely excellent dispersion stability can be obtained.
- aqueous pigment dispersion thus obtained by the method for producing an aqueous pigment dispersion of the present invention is also one of the present invention.
- FIG. 1 is a schematic diagram of a pigment disperser used in the present invention.
- FIG. 2 is a schematic diagram of a pigment disperser used in the present invention. Explanation of reference numerals
- aqueous medium D solid content: 30%
- a polyurethane type polymer emulsifier having an acid value of 32 mgKOHZg and a weight average molecular weight of 26,000, having a saturated hydrocarbon ring as a hydrophobic part and a lipoxyl group as a hydrophilic part, was obtained.
- the polyurethane polymer emulsifier showed a transparent dispersion state in an aqueous medium.
- a bead mill (capacity 1. 4 L, Wiley, A, Bacco one phen Co.) filling ratio 60 capacity steel beads of particle child size lmm to 0 /.
- the above mixtures E to H, K and L were dispersed at a peripheral speed of the stirring plate of 14 mZsec, and then diluted twice (by weight) with water to obtain Comparative Examples 1 to 6.
- Comparative Examples 7 to 12 were obtained using the above mixtures A to D, I, and J under a pressure of 5 ⁇ 10 4 kPa with a pass number of 5 times. .
- the materials used this time are as follows.
- Pigment Cyanine pigment with lid opening (Riono Blue 7330, manufactured by Toyo Ink Manufacturing Co., Ltd.)
- KM 70 manufactured by Shin-Etsu Chemical Co., Ltd.
- the average particle diameter is 0.10 m or less.
- the average particle diameter exceeds 0.15 win and 0.20 im or less.
- the particle size distributions of the pigments of Examples 1 to 6 and Comparative Examples 1 to 12 were measured by the above measuring device. The larger the ratio (%) of the pigment having a particle diameter of 0.5 to 1.5 times the average particle diameter to the total weight of the pigment, the narrower the particle size distribution was.
- Examples 1 to 6 and Comparative Examples 1 to 12 were collected in a glass bottle and sealed. Storage stability was evaluated based on the presence or absence of sediment when stored at C for 10 days.
- Chromogenicity Examples 1 to 6 and Comparative Examples 1 to 12 were painted on a high-quality paper with a meyer bar, and the degree of dullness and gloss was visually judged. It was judged that a color with less dullness and high gloss was better. .
- the aqueous pigment dispersion obtained by the production method of the present invention has a higher pigment dispersion than that produced by using an ordinary pigment dispersing apparatus. Is an aqueous pigment dispersion having a finer particle diameter, excellent dispersion stability, and extremely good coloring properties.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Dispersion Chemistry (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Pigments, Carbon Blacks, Or Wood Stains (AREA)
- Ink Jet (AREA)
Description
Claims
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP02741313A EP1418210A4 (en) | 2001-06-26 | 2002-06-26 | PROCESS FOR PREPARING AN AQUEOUS PIGMENT DISPERSION AND AQUEOUS PIGMENT DISPERSION MADE THEREOF |
KR10-2003-7002745A KR20030027079A (ko) | 2001-06-26 | 2002-06-26 | 수성안료 분산체의 제조방법 및 그 방법으로부터 얻어지는수성안료 분산체 |
US10/480,832 US20040232262A1 (en) | 2001-06-26 | 2002-06-26 | Process for producing aqueous pigment dispersion and aqueous pigment dispersion obtained by the process |
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2001193754 | 2001-06-26 | ||
JP2001-193754 | 2001-06-26 | ||
JP2002-19056 | 2002-01-28 | ||
JP2002019056A JP3935363B2 (ja) | 2001-06-26 | 2002-01-28 | 水性顔料分散体の製造方法およびその方法から得られる水性顔料分散体 |
Publications (1)
Publication Number | Publication Date |
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WO2003000805A1 true WO2003000805A1 (fr) | 2003-01-03 |
Family
ID=26617607
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/JP2002/006380 WO2003000805A1 (fr) | 2001-06-26 | 2002-06-26 | Procede de production d'une dispersion aqueuse de pigment et dispersion aqueuse de pigment obtenue au moyen dudit procede |
Country Status (6)
Country | Link |
---|---|
US (1) | US20040232262A1 (ja) |
EP (1) | EP1418210A4 (ja) |
JP (1) | JP3935363B2 (ja) |
KR (1) | KR20030027079A (ja) |
TW (1) | TW583284B (ja) |
WO (1) | WO2003000805A1 (ja) |
Cited By (3)
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WO2018162439A1 (en) | 2017-03-08 | 2018-09-13 | Onxeo | New predictive biomarker for the sensitivity to a treatment of cancer with a dbait molecule |
EP3594343A1 (en) | 2015-07-23 | 2020-01-15 | Institut Curie | Use of a combination of dbait molecule and parp inhibitors to treat cancer |
US10799501B2 (en) | 2015-11-05 | 2020-10-13 | King's College Hospital Nhs Foundation Trust | Combination of an inhibitor of PARP with an inhibitor of GSK-3 or DOT1L |
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JP4581319B2 (ja) * | 2002-09-11 | 2010-11-17 | 富士ゼロックス株式会社 | 水性インク組成物、その製造方法、及び水性インク組成物を用いる画像形成方法 |
TW553767B (en) * | 2002-12-30 | 2003-09-21 | Ind Tech Res Inst | Method for producing ultra-fine dispersion solution |
JP4470012B2 (ja) * | 2003-11-19 | 2010-06-02 | 山陽色素株式会社 | インクジェットインク用顔料分散体及びその製造方法 |
JP4539104B2 (ja) * | 2004-02-10 | 2010-09-08 | コニカミノルタエムジー株式会社 | 活性光線硬化型インクを用いた画像形成方法及びインクジェット記録装置 |
US7666255B2 (en) * | 2005-03-09 | 2010-02-23 | Hewlett-Packard Development Company, L.P. | Ink-jet inks having surfactants below the critical micelle concentration and associated methods |
JP4972332B2 (ja) * | 2005-03-31 | 2012-07-11 | 富士フイルム株式会社 | インクジェット用水性顔料記録液及びインクセット |
US20070043144A1 (en) * | 2005-08-18 | 2007-02-22 | Eastman Kodak Company | Pigment ink jet ink composition |
US7655708B2 (en) | 2005-08-18 | 2010-02-02 | Eastman Kodak Company | Polymeric black pigment dispersions and ink jet ink compositions |
JP5224699B2 (ja) | 2007-03-01 | 2013-07-03 | 富士フイルム株式会社 | インク組成物、インクジェット記録方法、印刷物、平版印刷版の製造方法、及び平版印刷版 |
WO2009009018A1 (en) * | 2007-07-12 | 2009-01-15 | Cabot Corporation | Inkjet ink compositions comprising polymer modified pigments and methods of preparing the same |
JP5278647B2 (ja) * | 2007-12-06 | 2013-09-04 | 凸版印刷株式会社 | 情報記録体 |
WO2010018311A1 (fr) * | 2008-08-13 | 2010-02-18 | LONG LASTING INNOVATION - L2I (Société à responsabilité limitée) | Procede pour la fixation de molecules actives sur un support, element actif obtenu par ce procede et composition chimique pour la mise en œuvre de ce procede |
JP5616083B2 (ja) * | 2010-03-08 | 2014-10-29 | 富士フイルム株式会社 | インクジェット顔料インクとこれを用いたインクジェット記録方法 |
JP5582829B2 (ja) * | 2010-03-08 | 2014-09-03 | 富士フイルム株式会社 | インクジェット顔料インクを用いたインクジェット記録方法、印刷物およびインクジェット記録装置 |
JP5757215B2 (ja) | 2011-10-14 | 2015-07-29 | 株式会社リコー | インクジェット用インク、インクジェット記録方法、及びインクジェット記録装置 |
JP2014024975A (ja) * | 2012-07-27 | 2014-02-06 | Dic Corp | インク及びインクジェット印刷用インク |
JP7077710B2 (ja) * | 2018-03-28 | 2022-05-31 | セイコーエプソン株式会社 | 水性インクジェット用組成物 |
JP7081260B2 (ja) * | 2018-03-28 | 2022-06-07 | セイコーエプソン株式会社 | 水性インクジェット用組成物 |
CN110317496B (zh) | 2018-03-28 | 2022-10-21 | 精工爱普生株式会社 | 水性喷墨用组合物 |
JP7077709B2 (ja) * | 2018-03-28 | 2022-05-31 | セイコーエプソン株式会社 | 水性インクジェット用組成物 |
JP7104541B2 (ja) * | 2018-03-30 | 2022-07-21 | 出光興産株式会社 | 脆性材料加工液組成物 |
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- 2002-06-26 WO PCT/JP2002/006380 patent/WO2003000805A1/ja active Application Filing
- 2002-06-26 TW TW91113985A patent/TW583284B/zh not_active IP Right Cessation
- 2002-06-26 KR KR10-2003-7002745A patent/KR20030027079A/ko not_active Application Discontinuation
- 2002-06-26 EP EP02741313A patent/EP1418210A4/en not_active Withdrawn
- 2002-06-26 US US10/480,832 patent/US20040232262A1/en not_active Abandoned
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Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP3594343A1 (en) | 2015-07-23 | 2020-01-15 | Institut Curie | Use of a combination of dbait molecule and parp inhibitors to treat cancer |
US10799501B2 (en) | 2015-11-05 | 2020-10-13 | King's College Hospital Nhs Foundation Trust | Combination of an inhibitor of PARP with an inhibitor of GSK-3 or DOT1L |
WO2018162439A1 (en) | 2017-03-08 | 2018-09-13 | Onxeo | New predictive biomarker for the sensitivity to a treatment of cancer with a dbait molecule |
Also Published As
Publication number | Publication date |
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KR20030027079A (ko) | 2003-04-03 |
US20040232262A1 (en) | 2004-11-25 |
TW583284B (en) | 2004-04-11 |
EP1418210A4 (en) | 2006-12-27 |
JP3935363B2 (ja) | 2007-06-20 |
EP1418210A1 (en) | 2004-05-12 |
JP2003082269A (ja) | 2003-03-19 |
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