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WO2007013599A1 - Procede de production de particules organiques, procede de production de compositions sous forme de dispersion de particules organiques, et encres pour imprimantes a jet d'encre contenant des compositions sous forme de dispersion de particules organiques obtenues par ledit procede - Google Patents

Procede de production de particules organiques, procede de production de compositions sous forme de dispersion de particules organiques, et encres pour imprimantes a jet d'encre contenant des compositions sous forme de dispersion de particules organiques obtenues par ledit procede Download PDF

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Publication number
WO2007013599A1
WO2007013599A1 PCT/JP2006/315005 JP2006315005W WO2007013599A1 WO 2007013599 A1 WO2007013599 A1 WO 2007013599A1 JP 2006315005 W JP2006315005 W JP 2006315005W WO 2007013599 A1 WO2007013599 A1 WO 2007013599A1
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WIPO (PCT)
Prior art keywords
group
organic
pigment
solvent
meth
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PCT/JP2006/315005
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English (en)
Japanese (ja)
Inventor
Naoya Shibata
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Fujifilm Corporation
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Priority to JP2007526915A priority Critical patent/JPWO2007013599A1/ja
Publication of WO2007013599A1 publication Critical patent/WO2007013599A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0001—Post-treatment of organic pigments or dyes
    • C09B67/0004—Coated particulate pigments or dyes
    • C09B67/0005—Coated particulate pigments or dyes the pigments being nanoparticles
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/006—Preparation of organic pigments
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J13/00—Colloid chemistry, e.g. the production of colloidal materials or their solutions, not otherwise provided for; Making microcapsules or microballoons
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J19/0053—Details of the reactor
    • B01J19/0066—Stirrers
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J19/18—Stationary reactors having moving elements inside
    • B01J19/1806—Stationary reactors having moving elements inside resulting in a turbulent flow of the reactants, such as in centrifugal-type reactors, or having a high Reynolds-number
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
    • B41J—TYPEWRITERS; SELECTIVE PRINTING MECHANISMS, i.e. MECHANISMS PRINTING OTHERWISE THAN FROM A FORME; CORRECTION OF TYPOGRAPHICAL ERRORS
    • B41J2/00—Typewriters or selective printing mechanisms characterised by the printing or marking process for which they are designed
    • B41J2/005—Typewriters or selective printing mechanisms characterised by the printing or marking process for which they are designed characterised by bringing liquid or particles selectively into contact with a printing material
    • B41J2/01—Ink jet
    • 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
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
    • C09B67/0084—Dispersions of dyes
    • C09B67/0091—Process features in the making of dispersions, e.g. ultrasonics
    • 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

Definitions

  • Ink for inkjet recording comprising organic particle production method, organic particle dispersion composition production method, and organic particle dispersion composition obtained thereby
  • the present invention relates to a method for producing organic particles in which organic particles are produced in the presence of a polymer dispersant.
  • the present invention also relates to a method for producing an organic particle dispersion composition obtained by concentrating the organic particle liquid.
  • the present invention relates to a method for producing redispersible organic particles, and a method for producing an organic particle dispersion composition.
  • the present invention also relates to an ink jet recording ink using the organic particle dispersion composition obtained by the above production method.
  • organic nanoparticles composed of organic compounds have a high potential as functional materials because the organic compounds themselves are diverse.
  • polyimide is used in many fields because it is a chemically and mechanically stable material such as heat resistance, solvent resistance, and mechanical properties, and has excellent electrical insulation.
  • Polyimide fine particles New uses for materials are expanding due to the combination of the characteristics and shape of polyimide. For example, as a proposed technique for using finely divided polyimide, it has been proposed to use an additive for powder toner for image formation (Patent Document 1).
  • organic pigments can be cited as applications such as paints, printing inks, electrophotographic toners, ink-jet inks, and color filters. It is an important material that cannot be lacked. Among them, high performance is required, and pigments for inkjet inks and color filter pigments are particularly important for practical use.
  • a gas phase method (a method in which a sample is sublimated in an inert gas atmosphere and particles are collected on a substrate), a liquid phase method (for example, a sample dissolved in a good solvent is stirred) (Reprecipitation method to obtain fine particles by injecting into a poor solvent with controlled conditions and temperature), laser ablation method (a method to make particles fine by irradiating a sample dispersed in a solution with a laser) Etc. are being studied.
  • laser ablation method a method to make particles fine by irradiating a sample dispersed in a solution with a laser
  • the reprecipitation method is a method for producing organic particles excellent in simplicity and productivity, but is not yet sufficient as a method for producing particles with high industrial utilization.
  • prepared by reprecipitation method There has not been enough research on how to separate and recover organic particles.
  • the prepared organic particles are obtained dispersed in a dilute solvent. Even if the desired organic particles can be prepared in the dispersion, the particle size changes in the concentration and separation / recovery process, and the monodispersity of the particles deteriorates. It cannot be put to practical use because of the cost.
  • Patent Document 5 it is described that pigment particles are made finer and prevent re-aggregation by containing a dispersing agent in the V or poor solvent.
  • this method also relates to the formation of pigment particles and cannot be said to be industrially practical when focusing on concentration and separation.
  • Patent Document 1 Japanese Patent Application Laid-Open No. 11 237760
  • Patent Document 2 Japanese Translation of Special Publication 2002-092700
  • Patent Document 3 Japanese Patent Laid-Open No. 6-79168
  • Patent Document 4 Japanese Patent Application Laid-Open No. 2004-91560
  • Patent Document 5 JP 2003-26972 A
  • An object of the present invention is to provide a method for producing monodispersed organic particles having a fine particle size.
  • a method for producing organic particles that can simplify the concentration process, suppress changes in particle size and monodispersity when concentrated, and can be easily redispersed when aggregated by concentration, and It is an object of the present invention to provide a method for producing an organic particle dispersion composition obtained by concentrating the composition. Another object of the present invention is to provide organic particles excellent in monodispersibility and sufficiently fine and highly industrially usable, a concentrated organic particle dispersion composition containing the same, and ink jet recording ink using the same.
  • At least 3 of a solution of an organic material dissolved in a good solvent, a solvent that is compatible with the good solvent and that is a poor solvent for the organic material, and a solution containing a polymer dispersant A method for producing organic particles, comprising mixing seeds and generating the organic material as particles in the mixed solution.
  • a method for producing an organic particle dispersion composition comprising producing an organic particle dispersion by the production method according to any one of (1) to (6) and concentrating it to a predetermined concentration. .
  • An ink for inkjet recording comprising an organic particle dispersion composition produced by the production method according to (7).
  • FIG. 1-1 is a cross-sectional view schematically showing a preferred embodiment of a production apparatus used in the method for producing organic particles of the present invention.
  • FIG. 12 is an enlarged partial cross-sectional view schematically showing a mixing chamber in a partial cross section as one embodiment of the manufacturing apparatus of FIG.
  • FIG. 13 is an enlarged partial cross-sectional view schematically showing a mixing chamber in a partial cross-section as another embodiment of the manufacturing apparatus of FIG.
  • FIG. 2 is a cross-sectional view schematically showing another preferred embodiment of the production apparatus used in the method for producing organic particles of the present invention.
  • FIG. 3 shows a further view of a production apparatus used in the method for producing organic particles of the present invention.
  • FIG. 6 is a cross-sectional view schematically illustrating another preferred embodiment.
  • FIG. 4 is an explanatory view showing a configuration example of an ultrafiltration device used in the method for producing organic particles of the present invention.
  • the organic material is not particularly limited as long as it can be precipitated and formed as organic particles.
  • organic materials include organic pigments, organic pigments, fullerenes, polydiacetylenes, polyimides, and other high molecular compounds, aromatic hydrocarbons or aliphatic hydrocarbons (for example, aromatic hydrocarbons or fatty acids having orientation).
  • Powerful particles such as aromatic hydrocarbons or aliphatic hydrocarbons having sublimability
  • organic pigments, organic dyes, and organic pigments that are preferred are polymer compounds. A combination of these may also be used.
  • the organic pigment that can be used in the method for producing organic particles of the present invention is not limited in hue.
  • perylene pigments such as CI Pigment Red 190 (CI No. 71140), CI Pigment Red 224 (CI No. 71127), CI Pigment Noorette 29 (CI No. 711 29), CI Pigment Orange 43 (CI No. 71105), or perinone pigments such as CI Pigment® Red 194 (CI No. 71100), CI Pigment® Noorette 19 (CI No. 73900), CI Pigment Nooret 42, CI Pigment Red 122 (CI number 73915), CI Pigment Red 192, CI Pigment Red 202 ( CI No. 73907), CI Pigment Red 207 (CI No.
  • CI Pigment Red 209 CI No. 73905
  • CI Pigment Red 206 CI No. 73900, 73920
  • Quinacridone quinone pigments such as CI Big Men Men Orange 48 (CI number 73900,73920) or CI Big Men Men Orange 49 (CI number 73900,73920), and anthraquinones such as C. I.
  • Pigment Yellow 147 (CI Number 60645) CI pigments, CI pigment red 168 (CI number 59300), etc.Anthotron pigments, CI pigment brown 25 (CI number 12510), CI pigment biolet 32 (CI number 12517), CI pigment yellow 180 (CI number) 21290), CI Big Men Yellow 181 (CI Number 11777), CI Big Men Orange 62 (CI Number 11775), or. I.
  • Pigment Red 185 (CI number 12516) and other benzimidazole pigments, CI Pigment Yellow 93 (CI number 20710), CI Pigment Yellow 94 (CI number 20038), CI Pigment Yellow 95 (CI number 20034) CI Big Men Yellow 128 (CI Number 20037), CI Big Men Yellow 166 (CI Number 20035), CI Big Men Orange 34 (CI Number 21115), CI Big Men Orange 13 (CI Number 21110), CI Big Men Men Orange 31 (CI No. 20050), C.I. Big Men ⁇ Red 144 (CI No. 20735), CI Big Men ⁇ Red 166 (CI No. 20 730), CI Big Men ⁇ Red 220 (CI No.
  • CI Big Men Men Red 255 (CI No. 561050), CI Big Men Men Red 264, CI pigment red 272 (CI number 5611 50), CI pigment orange 71, or diketopyrrolopyrrole pigments such as CI pigment orange 73, thioindigo pigments such as CI pigment red 88 (CI number 73312), C pigment Isoindoline pigments such as yellow 139 (CI number 56298), CI pigment orange 66 (CI number 48210), CI pigment yellow 109 (CI number 56284), or the like.
  • I. Pigment Orange 61 (CI No. 11295) and other isoindolinone pigments, CI Pigment Orange 40 (CI No. 59700), or And I. bigumen red 216 (CI number 59710) and other isopyrantron pigments such as CI pigment violet 31 (60010).
  • Two or more kinds of organic pigments or solid solutions of organic pigments can be used in combination in the method for producing organic particles of the present invention.
  • organic dyes include azo dyes, cyanine dyes, merocyanine dyes, and coumarin dyes.
  • polymer compound examples include polydiacetylene and polyimide.
  • the organic particles of the present invention contain an organic material solution in which an organic material is dissolved in a good solvent, a poor solvent for the organic material (hereinafter also simply referred to as “poor solvent for organic particles”), and a polymer dispersant.
  • a good solvent a poor solvent for the organic material
  • a polymer dispersant a polymer dispersant to obtain organic particles.
  • the good solvent is not particularly limited as long as it can dissolve the organic material to be used and is compatible with or uniformly mixed with the poor solvent used in the preparation of the organic particles.
  • the solubility of the organic material in a good solvent is preferably 0.2% by mass or more, more preferably 0.5% by mass or more. This solubility may be the solubility when dissolved in the presence of an acid or alkali.
  • the compatibility of the poor solvent and the good solvent or the preferable mixing property is preferably within a range of 30% by mass or more, and more preferably 50% by mass or more.
  • the good solvent examples include an aqueous solvent (for example, water or hydrochloric acid, sodium hydroxide aqueous solution), alcohol solvent, amide solvent, ketone solvent, ether solvent, aromatic solvent, carbon disulfide. , Aliphatic solvents, nitrile solvents, sulfoxide solvents, halogen solvents, ester solvents, ionic liquids, mixed solvents thereof, and the like, aqueous solvents, alcohol solvents, ester solvents, sulfoxide solvents.
  • a water-based solvent in which a solvent or an amide solvent is preferred, a sulfoxide solvent or an amide solvent in which a sulfoxide solvent or an amide solvent is more preferred is particularly preferred.
  • amide solvents include N, N dimethylformamide, 1-methyl-2-pyrrolidone, 2 pyrrolidinone, 1,3 dimethyl-2-imidazolidinone, 2 pyrrolidinone, ⁇ -force prolatatum, formamide, ⁇ -methylformamide, and acetateamide. , ⁇ -methylacetamide, ⁇ , ⁇ ⁇ ⁇ ⁇ dimethylacetamide, ⁇ ⁇ ⁇ methylpropanamide, hexamethylphosphoric triamide and the like.
  • the concentration of the organic material solution in which the organic material is dissolved in the good solvent depends on the organic material that is desired to be in the range of the saturated concentration of the organic material to the good solvent in the dissolution conditions or about 1 to 100 of this. For example, when a higher yield than that expected for an industrial production scale in which 0.5 to 12% by mass is preferred is desired, it is preferably 2 to 12% by mass.
  • the conditions for preparing the organic material solution can be selected from a range of normal pressure to subcritical and supercritical conditions, with no particular restrictions on the conditions for preparing the organic material solution.
  • the temperature at normal pressure is preferably 10 to 150 ° C Mashi—5 to 130 ° C. is more preferred. 0 to 100 ° C. is particularly preferred.
  • the organic material is preferably dissolved in a good solvent uniformly or acidic.
  • pigments with alkaline and dissociable groups in the molecule are alkaline, but when there are no alkaline and dissociable groups and protons are attached to the molecule, the acidity is used. It is done.
  • quinatalidone, diketopyrrolopyrrole, and disazo condensation pigments are alkaline, and phthalocyanine pigments are acidic.
  • the base used for the alkaline dissolution is an inorganic base such as lithium hydroxide, sodium hydroxide, potassium hydroxide, calcium hydroxide, or barium hydroxide, or trialkylamine.
  • Power which is an organic base such as diazabicycloundecene (DBU) and metal alkoxide, preferably an inorganic base.
  • DBU diazabicycloundecene
  • metal alkoxide preferably an inorganic base.
  • the amount of the base used is not particularly limited as long as the pigment can be uniformly dissolved, but in the case of an inorganic base, it is preferably 1.0 to 30 molar equivalents relative to the organic material, and more Preferably, it is 1.0 to 25 molar equivalents, and more preferably 1.0 to 20 molar equivalents.
  • an organic base it is preferably 1.0 to: LOO molar equivalent, more preferably 5.0 to 100 molar equivalent, and further preferably 20 to 100 molar equivalent with respect to the organic material.
  • the acid used in the case of acidic dissolution is preferably an inorganic acid such as sulfuric acid, hydrochloric acid, or phosphoric acid, or an organic acid such as acetic acid, trifluoroacetic acid, oxalic acid, methanesulfonic acid, or trifluoromethanesulfonic acid.
  • an inorganic acid such as sulfuric acid, hydrochloric acid, or phosphoric acid
  • an organic acid such as acetic acid, trifluoroacetic acid, oxalic acid, methanesulfonic acid, or trifluoromethanesulfonic acid.
  • sulfuric acid is preferably sulfuric acid.
  • the amount of the acid used is not particularly limited as long as it is an amount capable of uniformly dissolving the organic material, and an excess amount is often used as compared with a strong base. Regardless of the inorganic acid or organic acid, it is preferably 3 to 500 molar equivalents, more preferably 10 to 500 molar equivalents, still more preferably 30 to 200 molar equivalents relative to the organic material.
  • an alkali or acid When an alkali or acid is mixed with an organic solvent and used as a good solvent for the organic material, the alkali or acid is completely dissolved, so that it is higher than some alkali or acid such as water or lower alcohol. Solvents with solubility can be added to the organic solvent.
  • the amount of water and lower alcohol is preferably 50% by mass or less based on the total amount of the organic material solution. The mass% or less is more preferable. Specifically, water, methanol, ethanol, n-propanol, isopropanol, butyl alcohol and the like can be used.
  • the poor solvent for the organic material is a poor solvent for the organic material, and is not particularly limited as long as it is compatible with or uniformly mixed with a good solvent that dissolves the organic material.
  • the poor solvent when the poor solvent is compatible with the good solvent of the organic material solution in this way, it affects the solubility of the organic material molecules in the liquid, and the organic material is precipitated.
  • the solubility of the organic material is preferably 0.02% by mass or less, more preferably 0.01% by mass or less. This solubility may be the solubility when dissolved in the presence of acid or alkali.
  • the compatibility or homogenous compatibility between the good solvent and the poor solvent is as described in the section of the good solvent.
  • the poor solvent examples include aqueous solvents (for example, water or hydrochloric acid, sodium hydroxide aqueous solution), alcohol solvents, ketone solvents, ether solvents, aromatic solvents, carbon dioxide, fatty acids Group solvents, nitrile solvents, halogen solvents, ester solvents, ionic liquids, mixed solvents thereof and the like, and aqueous solvents, alcohol solvents, and ester solvents are preferred.
  • an aqueous solvent is very preferable.
  • the alcohol solvent include methanol, ethanol, isopropyl alcohol, n-propyl alcohol, 1-methoxy 2-propanol and the like.
  • ketonic solvents include acetone, methyl ethyl ketone, methyl isobutyl ketone, and cyclohexanone.
  • ether solvent include dimethyl ether, jetyl ether, and tetrahydrofuran.
  • aromatic solvent include benzene and toluene.
  • aliphatic solvent include hexane.
  • nitrile solvent include acetonitrile.
  • halogen solvent include dichloromethane, trichloroethylene, and the like.
  • ester solvent include ethyl acetate, ethyl lactate, 2- (1-methoxy) propyl pyracetate, and the like.
  • ionic liquids include 1-butyl-3 -Methyl imidazolium and PF salt.
  • the polymer dispersant is mixed as a third solution separately from the organic material solution and the poor solvent for the organic material.
  • the molecular weight of the polymer dispersant can be used without limitation as long as it can be uniformly dissolved as a solution, but preferably has a molecular weight of 1,000 to 2,000,000, and 5,000 to 1,000,000. 000 force is more preferable 10,000-500,000 force is more preferable ⁇ 10, 000-100,000 force is particularly preferable!
  • molecular weight is The mass average molecular weight means that the polymer compound is a polydisperse system and does not necessarily have the same molecular weight or particle weight, so when the molecular weight is measured, the value obtained is the average molecular weight averaged in some form.
  • the solvent for dissolving the polymer dispersant is not particularly limited as long as the polymer dispersant can be dissolved at a desired concentration.
  • Aqueous solvent for example, water, hydrochloric acid, sodium hydroxide aqueous solution
  • alcohol solvent ketone solvent, monotel solvent, aromatic solvent, carbon disulfide, aliphatic solvent, nitrile solvent , Halogen-based solvents, ester-based solvents, ionic liquids, mixed solvents thereof, and the like, and water-based solvents, alcohol-based solvents, and ester-based solvents are preferable.
  • the concentration of the polymer dispersant in the solution is determined by the solubility of the polymer dispersant, etc.
  • the amount of the polymer dispersant (the total amount when used in combination with other dispersants) is the total amount of the solution. It is preferably 1 to 90% by mass, more preferably 10 to 80% by mass, and particularly preferably 30 to 80% by mass.
  • polymer dispersing agent examples include, for example, polybulurpyrrolidone, polybutyl alcohol, polybutyl methyl ether, polyethylene oxide, polyethylene glycol, polypropylene glycol, polyacrylamide, polyethyleneimine, butyl alcohol, acetic acid.
  • natural polymers such as alginate, gelatin, albumin, casein, gum arabic, tonganto gum and lignosulfonate can also be used.
  • polybutylpyrrolidone, polyacrylamide, and polyethyleneimine are preferable.
  • These polymer dispersants can be used alone or in combination of two or more.
  • a polymer compound represented by the following general formula (1) can be used as the polymer dispersant or in combination therewith.
  • a 1 is an acidic group, a group having a basic nitrogen atom, a urea group, a urea group, a group having a coordinating oxygen atom, or a hydrocarbon group having 4 or more carbon atoms.
  • n A 1 may be the same or different.
  • a 1 is not particularly limited, and examples of the “monovalent organic group having an acidic group” include a carboxylic acid group, a sulfonic acid group, a monosulfate group, and a phosphoric acid group. And monovalent organic groups having a monophosphate group and a boric acid group.
  • the “monovalent organic group having a group having a basic nitrogen atom” for example, a monovalent organic group having an amino group (one NH 3), a substituted imino group (one NHR 8 , —NR 9 R 1G Monovalent organic group having (Here, R 8 , R 9 and R 1G each independently represent an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, and an aralkyl group having 7 to 30 carbon atoms.
  • a monovalent organic group having a guanidyl group represented by the following general formula (al) (in the general formula (al), R al and R a2 are each independently an alkyl group having 1 to 20 carbon atoms, An aryl group having 6 to 20 carbon atoms and an aralkyl group having 7 to 30 carbon atoms.
  • a monovalent organic group having an amidinyl group represented by the following general formula (a2) [in the general formula (a2), R a3 and R a4 are each independently an alkyl group having 1 to 20 carbon atoms, carbon It represents an aryl group having 6 to 20 carbon atoms and an aralkyl group having 7 to 30 carbon atoms. And the like.
  • Rea monovalent organic group having a group for example, - NHCONHR 15 (wherein, R 1 5 is or a hydrogen atom, an alkyl group having up to 20 carbon atoms, 6 or more carbon atoms 20 And the following aryl groups and aralkyl groups having 7 to 30 carbon atoms).
  • Examples of the “monovalent organic group having a urethane group” include: —NHCOOR 16 , —OCO NHR 17 (wherein R 16 and R 17 are each independently an alkyl group having 1 to 20 carbon atoms, carbon number) Represents an aryl group having 6 to 20 carbon atoms, and an aralkyl group having 7 to 30 carbon atoms.).
  • Examples of the “group having a group having a coordinating oxygen atom” include a group having an acetylethylacetonate group and a group having a crown ether.
  • Examples of the “group having a hydrocarbon group having 4 or more carbon atoms” include an alkyl group having 4 or more carbon atoms (for example, octyl group, dodecyl group, etc.), an aryl group having 6 or more carbon atoms (for example, a phenyl group, Naphthyl group) and aralkyl groups having 7 or more carbon atoms (for example, benzyl group). At this time, there is no upper limit to the number of carbon atoms, but it is preferably 30 or less.
  • Examples of the “group having an alkoxysilyl group” include groups having a trimethoxysilyl group, a triethoxysilyl group, and the like.
  • Examples of the “group having an epoxy group” include a group having a glycidyl group. I can get lost.
  • Examples of the “group having an isocyanate group” include a 3-isocyanatopropyl group.
  • Examples of the “group having a hydroxyl group” include a 3-hydroxypropyl group.
  • a 1 a monovalent organic group having an acidic group, a group having a basic nitrogen atom, a urea group, and a hydrocarbon group having 4 or more carbon atoms, a group selected. Preferably it is.
  • the organic dye structure or heterocyclic ring is not particularly limited, and more specifically, examples of the organic dye structure include phthalocyanine compounds, insoluble azo compounds, azo lake compounds, anthraquinones. Compounds, quinacridone compounds, dioxazine compounds, diketopyrrolopyrrole compounds, anthrapyridine compounds, ansanthrone compounds, indanthrone compounds, flavanthrone compounds, perinone compounds, perylene compounds, thioindigo compounds, etc. It is done.
  • heterocyclic ring examples include thiophene, furan, xanthene, pyrrole, pyrroline, pyrrolidine, dioxolane, pyrazole, pyrazoline, vilazolidin, imidazole, oxazole, thiazole, oxazidazole, triazole, thiadiazole, pyran, pyridine, piperidine.
  • the organic dye structure or heterocyclic ring may have a substituent.
  • substituents include an alkyl group having 1 to 20 carbon atoms such as a methyl group and an ethyl group. , Phenyl groups, naphthyl groups and the like having 6 to 16 carbon atoms such as aryl groups, hydroxyl groups, amino groups, carboxyl groups, sulfonamido groups, N-sulfolamide groups, and acetoxy groups.
  • the A 1 is preferably a monovalent organic group represented by the following general formula (4).
  • B 1 is an acidic group, a group having a basic nitrogen atom, a urea group, a urethane group, a group having a coordinating oxygen atom, a hydrocarbon group having 4 or more carbon atoms, A group selected from an alkoxy silyl group, an epoxy group, an isocyanate group, and a hydroxyl group, or an organic dye structure or a heterocyclic ring which may have a substituent.
  • R 18 represents a single bond or an alvalent organic or inorganic group. Represents a linking group. al represents 1 to 5, and al B 1 may be the same or different.
  • B 1 has the same meaning as A 1 in formula (4), and the preferred embodiment is also similar.
  • the organic dye structure or heterocyclic ring include phthalocyanine compounds and insoluble azo compounds.
  • Organic dye structures such as thioindigo compounds such as thiophene, furan, xanthene, pyrrole, pyrroline, pyrrolidine, dioxolane, pyrazole, pyrazoline, virazolidine, imidazole, oxazole, thiazole, oxadiazole, triazole, thiadiazole, pyran, pyridine
  • the organic dye structure or heterocyclic ring may have a substituent.
  • substituents include an alkyl group having 1 to 20 carbon atoms such as a methyl group and an ethyl group. , Phenyl groups, naphthyl groups and the like having 6 to 16 carbon atoms such as aryl groups, hydroxyl groups, amino groups, carboxyl groups, sulfonamido groups, N-sulfolamide groups, and acetoxy groups.
  • alkoxy group having 1 to 6 carbon atoms such as methoxy group and ethoxy group
  • salt Halogen atoms such as silicon and bromine, methoxycarbon groups, ethoxycarbon groups, cyclohexyl groups, etc., alkoxycarbon groups having 2 to 7 carbon atoms, cyan groups, t And carbonic acid ester groups such as H-til carbonate.
  • R 18 represents a single bond or an al + monovalent linking group, and al represents 1 to 5.
  • the linking group R 18 includes 1 to 1006 HH carbon atoms, 0 to 10 nitrogen atoms, 0 to 50 oxygen atoms, 1 to 200 hydrogen atoms, and Groups comprising from 0 to 20 sulfur atoms are included and may be unsubstituted or further substituted.
  • R 18 is preferably an organic linking group.
  • R 18 include the following structural units or groups formed by combining the structural units.
  • R 18 has a substituent
  • substituents include an alkyl group having 1 to 20 carbon atoms such as a methyl group and an ethyl group, a phenyl group and a naphthyl group having 6 to 6 carbon atoms.
  • aryl groups Up to 16 aryl groups, hydroxyl groups, amino groups, carboxyl groups, sulfonamido groups, N-sulfo-lumamide groups, acetoxy groups, etc., acyloxy groups having 1 to 6 carbon atoms, methoxy groups, ethoxy groups Alkoxy groups having 1 to 6 carbon atoms, such as halogen atoms such as chlorine and bromine, alkoxy groups having 2 to 7 carbon atoms such as methoxycarbonyl groups, ethoxycarbonyl groups, and cyclohexylcarbonyl groups. Examples thereof include a carbon group, a cyan group, and a carbonic ester group such as t-butyl carbonate.
  • R 1 represents an (m + n) -valent linking group. m + n satisfies 3 ⁇ : L0.
  • Examples of the (m + n) -valent linking group represented by R 1 include: 1 to: L00 carbon atoms, 0 to 10 nitrogen atoms, 0 to 50 oxygen atoms, 1 From 1 to 200 hydrogen atoms, and from 0 to 20 sulfur atomic groups are included, which may be unsubstituted or further substituted.
  • R 1 is preferably an organic linking group.
  • R 1 include the structural units (t-1) to (t-34) or a group composed of a combination of the structural units (which may form a ring structure). ⁇ .
  • R 1 has a substituent
  • substituents include an alkyl group having 1 to 20 carbon atoms such as a methyl group and an ethyl group, a phenyl group and a naphthyl group having 6 to 6 carbon atoms.
  • Carbon number up to 16 carbon atoms such as aryl group, hydroxyl group, amino group, carboxyl group, sulfonamido group, N-sulfol amide group, acetooxy group, etc.
  • alkoxy groups such as halogen atoms such as chlorine and bromine, methoxy carbo yl groups, ethoxy carbo yl groups, cyclohexyl carboxy groups, etc.
  • carbonic acid ester groups such as t-butyl carbonate.
  • R 2 represents a single bond or a divalent linking group.
  • R 2 includes: 1 to: up to L00 carbon atoms, 0 to 10 nitrogen atoms, 0 to 50 oxygen atoms, 1 to 200 hydrogen atoms, and 0 to Up to 20 sulfur nuclear power groups are included, which may be unsubstituted or further substituted.
  • R 2 is preferably an organic linking group.
  • R 2 include the structural units of the above t-3, 4, 7-18, 22-26, 32, 34, or groups configured by combining the structural units.
  • R 2 has a substituent
  • substituents include an alkyl group having 1 to 20 carbon atoms such as a methyl group and an ethyl group, a phenyl group and a naphthyl group having 6 to 6 carbon atoms.
  • aryl groups Up to 16 aryl groups, hydroxyl groups, amino groups, carboxyl groups, sulfonamido groups, N-sulfol amides 1 to 6 carbon atoms such as alkenyl groups and acetoxy groups, alkoxy groups up to 1 to 6 carbon atoms such as methoxy groups and ethoxy groups, halogen atoms such as chlorine and bromine, methoxycarbon groups and ethoxycarbo Examples thereof include an alkoxy carbo group having 2 to 7 carbon atoms such as a thiol group and a cyclohexyl oxy carboxy group, a carbonate group such as a cyano group and t-butyl carbonate, and the like.
  • m represents 1 to 8. As m, 1-5 is preferable, 1-3 is more preferable, and 1-2 is particularly preferable.
  • N represents 2-9.
  • n is preferably 2 to 8 forces S, more preferably 3 to 6 with 2 to 7 being more preferable.
  • P 1 represents a polymer skeleton and can be selected from ordinary polymers according to the purpose and the like.
  • the polymer skeleton is composed of a polymer or copolymer of a bull monomer, an ester polymer, an ether polymer, a urethane polymer, an amide polymer, an epoxy polymer, a silicone polymer, and these.
  • a modified product or a copolymer for example, a copolymer of a polyether Z polyurethane copolymer, a polymer of polyether Z butyl monomer, etc. (any of a random copolymer, a block copolymer, a graft copolymer) May be present).
  • a polymer or copolymer of a bulle monomer Selected from the group consisting of a polymer or copolymer of a bulle monomer, an ester polymer, an ether polymer, a urethane polymer, and a modified product or a copolymer thereof.
  • Particularly preferred are polymers or copolymers of vinyl monomers, at least one of which is more preferred.
  • the polymer is preferably soluble in an organic solvent. If the affinity with the organic solvent is low, for example, when used as a pigment dispersant, the affinity with the dispersion medium is weakened, and it may not be possible to secure a sufficient adsorption layer for dispersion stability.
  • a high molecular compound represented by the following general formula (2) is more preferable.
  • a 2 has the same meaning as A 1 in the general formula (1), and the specific preferred embodiment thereof is also the same, but as a specific example of the organic dye structure, Heterocycles such as phthalocyanine compound, azo lake compound, anthraquinone compound, dioxazin compound, diketo pyropyro compound are preferred as imidazole, triazole, pyridine, piperidine Monoreforin, triazine, isoindoline, isoindolinone, benzimidazolone, benzothiazole, succinimide, phthalimide, naphthalimide, hydantoin, indole, quinoline, carbazole, atalidine, attaridone and anthraquinone are more preferred.
  • Heterocycles such as phthalocyanine compound, azo lake compound, anthraquinone compound, dioxazin compound, diketo pyropyro compound are preferred as imidazole, triazo
  • the substituent which may have a substituent as in A 1 is the same as that in A 1 , and the preferred embodiment is also the same.
  • the monovalent organic group represented by the general formula (4) is preferred, and details and specific examples, preferred and embodiments of the organic group are the same.
  • R 3 represents a (x + y) -valent linking group. Represented by R 3 (x
  • + y) valent linking groups include 1 to 60 carbon atoms, 0 to 10 nitrogen atoms, 0 to 50 oxygen atoms, 1 to 100 hydrogen atoms, and Groups comprising 0 to 20 sulfur atoms are included and may be unsubstituted or further substituted.
  • the linking group of the represented by R 3 (x + y) value has the same meaning as the linking group of (m + n) valent in the R 1, it is the same a preferred embodiment thereof. Further, specific examples include the same structural unit as described above or a group constituted by combining the structural units.
  • the linking group represented by R 3 is preferably an organic linking group. Preferred specific examples of the organic linking group are shown below. However, the present invention is not limited to these.
  • R 3 has a substituent
  • substituents include carbon such as an alkyl group having 1 to 20 carbon atoms such as a methyl group and an ethyl group, a phenyl group, and a naphthyl group. Number 6 to 16 aryl groups, hydroxyl groups, amino groups, carboxyl groups, sulfonamido groups, N-sulfolamide groups, acetoxy groups, etc.
  • acyl groups having 1 to 6 carbon atoms such as acyl groups having 1 to 6 carbon atoms, methoxy groups, ethoxy groups, etc. C1-C6 alkoxy groups, halogen atoms such as chlorine and bromine, methoxycarbol groups, ethoxycarbon groups, cyclohexylcarboxy groups, etc.
  • -Carbonate group such as -l group, cyano group and t-butyl carbonate.
  • R 4 and R 5 each independently represents a single bond or a divalent linking group.
  • Preferred examples include SO or a divalent group in which two or more of these groups are combined.
  • R 19 and R 2G each independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.
  • 0 is preferably an organic linking group.
  • R 4 a linear or branched alkylene group, an aralkylene group, OC (
  • the divalent group combined above is particularly preferred.
  • R 5 a single bond, a linear or branched alkylene group, Ararukiren group, -O
  • a divalent group in which two or more of these groups are combined is particularly preferred.
  • R 5 has a substituent
  • substituents include carbon such as an alkyl group having 1 to 20 carbon atoms such as a methyl group and an ethyl group, a phenyl group, and a naphthyl group.
  • Number 6 Up to 16 carbon atoms such as aryl group, hydroxyl group, amino group, carboxyl group, sulfonamido group, N-sulfolamide group, acetoxy group, etc. carbon number up to 1-6, such as acyloxy group, methoxy group, ethoxy group, etc.
  • alkoxy groups such as halogen atoms such as chlorine and bromine, methoxy carbo yl groups, ethoxy carbo yl groups, cyclohexyl carboxy groups, etc.
  • y represents 1 to 8, 1 to 5 is preferable, and 1 to 3 is more preferable, and 1 to 2 is particularly preferable.
  • X represents 2-9, 2-8 are preferred, 2-7 are more preferred, and 3-6 are particularly preferred.
  • P 2 in the general formula (2) represents a polymer skeleton and can be selected from ordinary polymers according to the purpose and the like.
  • the preferred embodiment of the polymer is the same as P 1 in the general formula (1), and the preferred embodiment is also the same.
  • R 21 represents a hydrogen atom or a methyl group
  • 1 represents 1 or 2.
  • the mass average molecular weight of the polymer represented by the general formula (1) is 1000-500,000 force S preferred ⁇ , 3000 to 100,000 times preferred ⁇ , 5000 to 80000 forces S more preferred. ⁇ , 7000-60000 is particularly preferred.
  • the weight average molecular weight is within the above range, the effects of the multiple functional groups introduced at the ends of the polymer are sufficiently exerted, and the performance of adsorbing to a solid surface, micelle forming ability, and surface activity is excellent. To do.
  • a polymer compound is used as a pigment dispersant, good dispersibility and dispersion stability can be achieved.
  • the polymer compound represented by the general formula (1) (including the polymer compound represented by the general formula (2)) is not particularly limited, but can be synthesized by the following method. Of the following synthesis methods, the following synthesis methods such as 3, 4, 5, etc. are particularly preferred because of the ease of synthesis, and the following synthesis methods such as 2, 3, 4, 5 are more preferred.
  • the polymer compound (preferably the polymer compound represented by the general formula (2)) used in the production method of the present invention is, for example, any one of the above 2, 3, 4, and 5 Although it can be synthesized by a method, it is more preferred to synthesize by the above method 5 because of ease of synthesis.
  • radical polymerization using a compound represented by the following general formula (3) as a chain transfer agent.
  • R 6 , R 7 , A 3 , g, and h are each R 3 in the general formula ( 2 ), It is synonymous with x and y, The preferable aspect is also the same.
  • the bull monomer is not particularly limited !, but, for example, (meth) acrylic acid esters, crotonic acid esters, buresters, maleic acid diesters, fumaric acid diesters, itaconic acid diesters , (Meth) acrylamides, butyl ethers, esters of butyl alcohol, styrenes, (meth) acrylonitrile and the like are preferable. Examples of such include the following compounds.
  • Examples of the (meth) acrylic acid esters include methyl (meth) acrylate, ethyl (meth) acrylate, n-propyl (meth) acrylate, isopropyl (meth) acrylate, (meth) N-butyl acrylate, isobutyl (meth) acrylate, t-butyl (meth) acrylate, n-hexyl (meth) acrylate, cyclohexyl (meth) acrylate, (meth) acrylic acid t- Butyl cyclohexyl, 2-ethylhexyl (meth) acrylate, t-octyl (meth) acrylate, dodecyl (meth) acrylate, octadecyl (meth) acrylate, acetooxyethyl (meth) acrylate, (meth) Acrylic acid phenyl, (meth) acrylic acid 2-hydroxye
  • crotonic acid esters examples include butyl crotonic acid and hexyl crotonic acid.
  • vinyl esters examples include butyl acetate, vinyl propionate, vinyl butyrate, vinyl methoxyacetate, vinyl benzoate, and the like.
  • maleic diesters examples include dimethyl maleate, diethyl maleate, and dibutyl maleate.
  • Examples of the fumaric acid diesters include dimethyl fumarate, jetyl fumarate, dibutyl fumarate, and the like.
  • Examples of the itaconic acid diesters include dimethyl itaconate, jetyl itaconate, and dibutyl itaconate.
  • Examples of the (meth) acrylamides include (meth) acrylamide, N-methyl (meth) acrylamide, N-ethyl (meth) acrylamide, N-propyl (meth) acrylamide, N-isopropyl (meth) ) Acrylamide, N—n-butylacrylic (meth) amide, N—t-butyl (meth) acrylamide, N cyclohexyl (meth) acrylamide, N— (2-methoxyethyl) (meth) acrylamide, N, N dimethyl ( Examples include (meth) acrylamide, N, N jetyl (meth) acrylamide, N-fell (meth) acrylamide, N-benzyl (meth) acrylamide, (meth) ataryloylmorpholine, and diacetone acrylamide.
  • styrenes examples include styrene, methyl styrene, dimethyl styrene, trimethyl styrene, ethyl styrene, isopropylino styrene, butyl styrene, hydroxy styrene, methoxy styrene, butoxy styrene, acetoxy styrene, chloro styrene, dichloro styrene.
  • Examples thereof include low styrene, promostyrene, chloromethyl styrene, hydroxystyrene protected with a group that can be deprotected by an acidic substance (for example, t-Boc, etc.), methyl vinylbenzoate, and a-methylstyrene.
  • butyl ethers examples include methyl vinyl ether, butyl vinyl ether, hexyl vinyl ether, and methoxyethyl vinyl ether.
  • (meth) acrylonitrile, heterocyclic groups substituted with vinyl groups for example, bullpyridine, bull pyrrolidone, bull force rubazole, etc.
  • N-buluformamide, N-bulacetoamide N-Buylimidazole, bull force prolatatone, etc. can be used.
  • butyl monomers having a functional group such as a urethane group, a urea group, a sulfonamide group, a phenol group, and an imide group can also be used.
  • a monomer having a urethane group or urea group can be appropriately synthesized by utilizing, for example, an addition reaction between an isocyanate group and a hydroxyl group or an amino group.
  • an addition reaction between an isocyanate group-containing monomer and a compound containing one hydroxyl group or a compound containing one primary or secondary amino group, or a hydroxyl group-containing monomer or primary or secondary amino group It can be appropriately synthesized by an addition reaction between a group-containing monomer and a monoisocyanate.
  • the above-mentioned radical monomers which may be polymerized by only one kind, or may be used in combination of two or more kinds, may be the usual bulle monomers. It can be obtained by polymerization according to a conventional method.
  • suitable solvents used in the solution polymerization method include monomers used and products produced It can be arbitrarily selected according to the solubility of the copolymer.
  • solvents used in the solution polymerization method.
  • the radical polymerization initiator may be an azo such as 2,2'-azobis (isobutyoxy-tolyl) (AIBN) or 2,2, -azobis- (2,4, -dimethylbare-tolyl).
  • AIBN 2,2'-azobis (isobutyoxy-tolyl)
  • 2,2, -azobis- (2,4, -dimethylbare-tolyl) Compounds, peracids such as benzoyl peroxide, and persulfates such as potassium persulfate and ammonium persulfate can be used.
  • the compound represented by the general formula (3) can be synthesized by the following method or the like, but the following method 7 is more preferable because of ease of synthesis.
  • a method of converting a halide compound having a plurality of functional groups (A 1 or A 2 in the above general formula) into a mercabtan compound (a method of reacting with thiourea and hydrolyzing, a method of directly reacting with NaSH, Examples include a method of reacting with CH COSNa and hydrolyzing.
  • Preferred examples of the "functional group capable of reacting with a mercapto group" in Method 7 include an acid halide, an alkyl halide, an isocyanate, a carbon-carbon double bond, and the like.
  • the “functional group capable of reacting with a mercapto group” is a carbon-carbon double bond, and the addition reaction is synthesized by a radical addition reaction.
  • Carbon The carbon double bond is more preferably a mono- or di-substituted bur group in terms of reactivity with the mercapto group.
  • the above-mentioned “compound having 3 to 10 mercapto groups in one molecule” and the above “having an acidic group, a group having a basic nitrogen atom, a urea group, a urethane group, and a coordinating oxygen atom” A compound having at least one functional group selected from a group, a hydrocarbon group having 4 or more carbon atoms, an alkoxysilyl group, an epoxy group, an isocyanate group, and a hydroxyl group, and having a carbon-carbon double bond.
  • the radical addition reaction product includes, for example, the above-mentioned “compound having 3 to 10 mercapto groups in one molecule” and “acid group, group having basic nitrogen atom, urea group, urethane group, coordinating oxygen”.
  • Examples of preferable solvents used in the above method include "a compound having 3 to LO mercapto groups in one molecule", "an acidic group, a group having a basic nitrogen atom, a urea group, a Lethane group, group having a coordinating oxygen atom, hydrocarbon group having 4 or more carbon atoms, alkoxysilane A compound having at least one functional group selected from the group consisting of an alkyl group, an epoxy group, an isocyanate group, and a hydroxyl group, and a functional group capable of reacting with a mercapto group (for example, a carbon-carbon double bond), and It can be arbitrarily selected according to the solubility of the radical addition reaction product.
  • methanol, ethanol, propanol, isopropanol, 1 methoxy 2-propanol, 1-methoxy 2-propyl acetate, acetone, methyl ethyl ketone, methyl isobutyl ketone, methoxypropyl acetate, lactate, ethyl acetate, acetonitrile, tetrahydrofuran, dimethylformamide, Kuroguchi Holm and Toluen are listed.
  • These solvents may be used as a mixture of two or more.
  • azo compounds such as 2, 2'-azobis (isobutyorph-tolyl) (AIBN), 2, 2, -azobis- (2, 4, -dimethylbare-tolyl)
  • Peroxides such as benzoyl peroxide, and persulfates such as potassium persulfate and ammonium persulfate can be used.
  • the polymer compound is preferably a polymer compound having an acidic group, and more preferably a polymer compound having a lpoxyl group.
  • A Compound compound having a carboxyl group Particularly preferred are copolymer compounds containing at least one of the repeating units and (B) at least one of the derived repeating units.
  • a repeating unit derived from acrylic acid or methacrylic acid which is preferably a repeating unit represented by the following general formula (I):
  • a repeating unit derived from tacrylate is particularly preferred.
  • R represents a hydrogen atom or an alkyl group having 1 to 5 carbon atoms.
  • R represents a hydrogen atom or an alkyl group having 1 to 5 carbon atoms.
  • R represents the following general formula (III)
  • R is a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, a hydroxy group
  • R and R are hydroxyalkyl groups or an aryl group having 6 to 20 carbon atoms.
  • Each represents a hydrogen atom or an alkyl group having 1 to 5 carbon atoms.
  • i represents a number from 1 to 5.
  • R represents a hydrogen atom or an alkyl group having 1 to 5 carbon atoms.
  • R represents the following general formula (V):
  • R represents an alkyl group having 2 to 5 carbon atoms or an aryl group having 6 to 20 carbon atoms.
  • R 1 and R 2 represent a hydrogen atom or an alkyl group having 1 to 5 carbon atoms.
  • j is a number between 1 and 5
  • the polymerization ratio of (A) a repeating unit derived from a compound having a carboxyl group and a repeating unit derived from the compound (B) having a carboxylic acid ester group is the total of repeating units (A). It is more preferable that the quantity ratio% to the number of repeating units is 3 to 40, and 5 to 35 is more preferable.
  • the molecular weight of the polymer refers to the mass average molecular weight unless otherwise specified.
  • the methods for measuring the molecular weight of the polymer include chromatographic methods, viscosity methods, light scattering methods, sedimentation rates. Law.
  • the mass average molecular weight measured by the chromatographic method is used unless otherwise specified.
  • the polymer compound may be either water-soluble or oil-soluble, water-soluble and oil-soluble.
  • the addition of the polymeric dispersant is not only performed during the formation of organic nanoparticles, for example, during extraction or concentration (or before or after), or when dispersed aggregated organic particles after concentration (or before or after), and these processes are completed. It may be added afterwards, or these yarns may be combined.
  • the high molecular dispersant may be contained in the composition as a binder described later. For example, it is also preferable to add the high molecular dispersant when finely dispersing the aggregated organic particles after concentrating the organic particle precipitate.
  • the amount of the polymer dispersant relative to the organic material is 100 parts by weight of the organic material in order to further improve the uniform dispersion and storage stability of the organic particles.
  • 0.1-: L000 is preferably in the range of 1 part by mass, more preferably in the range of 1-500 parts by mass, particularly preferably in the range of 10-250 parts by mass. If the amount is less than 1 part by mass, the dispersion stability of the organic material particles may not be improved.
  • the amino group includes a primary amino group, a secondary amino group, and a tertiary amino group, and the number of the amino groups may be one or more.
  • NS examples thereof include xylethylenealkyl sulfate salts. Among them, Nashiro N alkyl taurine salt is preferred! As the N-acyl N alkyltaurine salt, those described in JP-A-3-273067 are preferable. These char-on dispersants can be used alone or in combination of two or more.
  • Quaternary ammonium salts alkoxy ⁇ polyamines, aliphatic amine polyglycol ethers, aliphatic amines, aliphatic amines and fatty alcohol powers derived diamines and polyamines, fatty acid-derived imidazolines and their Contains salts of cationic substances.
  • These cationic dispersants can be used alone or in combination of two or more.
  • the anionic dispersant is a dispersant having both an anion group portion in the molecule and a cationic group portion in the molecule of the cationic dispersant in the molecule.
  • Nonionic dispersant (Nonionic surfactant):
  • Polyoxyethylene alkyl ether, polyoxyethylene alkyl aryl ether, polyoxyethylene fatty acid ester, sorbitan fatty acid ester, polyoxyethylene sorbitan fatty acid ester, polyoxyethylene alkylamine, glycerin fatty acid Examples include esters. Of these, polyoxyethylene alkylaryl ether is preferred. These nonionic dispersants can be used alone or in combination of two or more.
  • sugar-containing pigment dispersants for example, sugar-containing pigment dispersants, piperidyl-containing pigment dispersants, naphthalene or perylene-derived pigment dispersants, pigment dispersants with functional groups linked to the pigment parent structure via methylene groups, chemically modified with polymers
  • Pigment parent structure pigment dispersant having a sulfonic acid group, pigment dispersant having a sulfonamide group, a pigment dispersant having an ether group, or a pigment dispersant having a carboxylic acid group, a carboxylic ester group, or a carboxamide group is there.
  • an alkali-soluble polymer dispersant when considering use as a color filter, it is preferable to use an alkali-soluble polymer dispersant.
  • compounds represented by the general formula (I) described in JP-A-2000-239554 are also preferably used.
  • A-N N-X- Y
  • A represents a component capable of forming an azo dye together with X—Y.
  • A can be arbitrarily selected as long as it is a compound capable of forming an azo dye by coupling with a diazo-um compound. Specific examples of A will be shown below, but the present invention is not limited thereto.
  • X represents a single bond or a group selected from divalent linking groups represented by structural formulas of the following formulas (i) to (v).
  • Z represents a lower alkylene group.
  • Z is the force expressed as one (CH) —
  • the b represents an integer of 1 to 5, preferably 2 or 3.
  • NR is
  • —NR represents a lower alkylamino group, it is represented as —N (C H), and r is an integer of 1 to 4.
  • any of the heterocyclic groups represented by the following structural formula is preferred.
  • Z and -NR are each a lower alkyl group or an alcohol.
  • a represents 1 or 2, preferably 2.
  • the compound represented by the general formula (Dl) can be synthesized, for example, by the method described in JP-A-2000-239554.
  • Q is an anthraquinone compound dye, an azo compound compound dye, a phthalocyanine compound dye, a quinatharidon compound compound dye, a dioxazine compound compound dye, an anthrapyrimidine compound compound dye, an anthrone compound compound, an indanthrone compound Represents an organic dye residue selected from a dye, a flavanthrone compound dye, a pyranthrone compound dye, a perinone compound dye, a perylene compound dye, and a thioindigo compound dye. It is more preferred that it is an azo compound pigment. Yes.
  • X is CO—, —CONH-Y one, SO NH-Y one, or CH NHCOCH
  • NH-Y— represents CO— and —CONH-Y—.
  • Y represents an alkylene group or an arylene group which may have a substituent.
  • More preferred is phenylene, toluylene or hexylene.
  • R and R are each independently a substituted or unsubstituted alkyl group or R and R
  • a methyl group, an ethyl group, a propyl group, or a pyrrolidyl group including a nitrogen atom is preferable, and an ethyl group is more preferable!
  • Y represents —NH 2 or —O 2.
  • Z represents a hydroxyl group or a group represented by the general formula (D3a), or when nl is 1, —NH 2 —X Q may be used.
  • ml represents an integer of 1 to 6, preferably 2 to 3.
  • nl represents an integer of 1 to 4, preferably 1 or 2.
  • the compound represented by the general formula (D3) is represented by the following general formula, for example.
  • the compound represented by the general formula (D3) is, for example, an amine compound having R and R and R
  • JP-B-5-72943 can also be referred to.
  • the graft copolymer may have at least an amino group and an ether group, and may contain other monomers as copolymer units.
  • the weight average molecular weight (Mw) of the graft copolymer is preferably 300 to 100,000 particles ⁇ , more preferably 5000 to 50,000 force! / ⁇ . If the mass average molecular weight (Mw) force is less than 3000, the aggregation of pigment nanoparticles cannot be prevented, and the viscosity may increase. When it exceeds 0000, the solubility in an organic solvent is insufficient, and the viscosity may increase.
  • the mass average molecular weight is a polystyrene-reduced mass average molecular weight measured by gel permeation chromatography (carrier: tetrahydrofuran).
  • the graft copolymer includes: (i) a polymerizable oligomer having an ethylenically unsaturated double bond at the terminal; (ii) a monomer having an amino group and an ethylenically unsaturated double bond; iii) It preferably contains at least a polymerizable monomer having an ether group as a copolymer unit, and (iv) optionally contains other monomers as copolymer units.
  • the content of the graft copolymer, (i) the polymerizable oligomer is preferably to be 15 to 98 mass 0/0 device 25 to 90 weight 0 / 0 is it forces Ri preferably fixture (ii) preferably be an amino group-containing monomer is 1 to 40 wt% instrument 5 to 3 0% by weight and is more preferably tool the (iii) the ether group
  • the polymerizable monomer is preferably 1 to 70% by mass, more preferably 5 to 60% by mass.
  • the content of the polymerizable oligomer is less than 15% by mass, a steric repulsion effect as a dispersant may not be obtained, and aggregation of pigment nanoparticles may not be prevented.
  • the ratio of the nitrogen-containing monomer is reduced, the adsorption ability to the pigment particles is lowered, and the dispersibility is not sufficient.
  • the content of the nitrogen-containing monomer is less than 1% by mass, the adsorption capacity for organic particles may be reduced and dispersibility may not be sufficient, and if it exceeds 40% by mass, the proportion of the polymerizable oligomer will decrease.
  • the solid repulsion effect as a dispersant cannot be obtained, and the aggregation of pigment particles may not be sufficiently prevented.
  • the content of the polymerizable monomer having an ether group is less than 1% by mass, the development suitability in the production of a color filter or the like may not be sufficient, and when it exceeds 70% by mass, the dispersant is used as a dispersant. Your ability may decline.
  • the polymerizable oligomer (hereinafter sometimes referred to as “macromonomer”) is an oligomer having a group having an ethylenically unsaturated double bond at the terminal.
  • the oligomer generally includes, for example, alkyl (meth) acrylate, hydroxy.
  • Cialkyl (meth) acrylate, styrene, acrylonitrile, butyl acetate, and butagen force At least one selected monomer force A homopolymer or a copolymer formed, and among them, alkyl (meth) acrylate Preferred are rate homopolymers or copolymers, polystyrene and the like.
  • these oligomers which may be substituted with a substituent are not particularly limited, and examples thereof include a halogen atom.
  • Preferred examples of the group having an ethylenically unsaturated double bond include a (meth) atalyloyl group, a bure group, and the like, and among these, a (meth) atalyloyl group is particularly preferred.
  • oligomers represented by the following general formula (E6) are preferable.
  • R 61 and R 63 represent a hydrogen atom or a methyl group.
  • R 62 represents an alkylene group which may be substituted with an alcoholic hydroxyl group having 1 to 8 carbon atoms, and an alkylene group having 2 to 4 carbon atoms is preferable.
  • Y 6 is a phenyl group, a phenyl group having an alkyl group having 1 to 4 carbon atoms, or —COOR 64 (where R 64 is an alcoholic hydroxyl group having 1 to 6 carbon atoms, halogen, Represents an optionally substituted alkyl group, a phenyl group, or an arylalkyl group having 7 to 10 carbon atoms.), A phenyl group or —COOR 64 (where R 64 is a carbon number of 1). Represents an alkyl group which may be substituted with ⁇ 4 alcoholic hydroxyl groups). q represents 20-200.
  • polymerizable oligomer examples include poly-2-hydroxyethyl (meth) atrelate, polystyrene, polymethyl (meth) acrylate, poly n-butyl (meth) acrylate, poly i butyl.
  • a (meth) acrylate, a copolymer thereof, and a polymer in which a (meth) taliloyl group is bonded to one of the molecular terminals is preferred.
  • the polymerizable oligomer may be a commercially available product or an appropriately synthesized one.
  • Preferable examples of the polymerizable oligomer in the present invention include, as a specific example, a polymer of alkyl (meth) acrylate and a copolymer of alkyl (meth) acrylate and polystyrene. And those having a number average molecular weight of 1000 to 20000 and having a (meth) atallyloyl group at the terminal.
  • Suitable examples of the amino group-containing monomer include at least one selected from compounds represented by the following general formula (E2).
  • R 21 represents a hydrogen atom or a methyl group.
  • R 22 represents an alkylene group having 1 to 8 carbon atoms, and among these, an alkylene group having 1 to 6 carbon atoms is preferable, and an alkylene group having 2 to 3 carbon atoms is particularly preferable.
  • X 2 represents N (R 23 ) (R 24 ), and one R 25 N (R 26 ) (R 27 ).
  • R 23 and R 24 represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or a phenyl group.
  • R 25 represents an alkylene group having 1 to 6 carbon atoms
  • R 26 and R 27 are a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or phenyl. Represents a group.
  • - N (R 23) R 23 and R 24 of (R 24) is a hydrogen atom or 1 to 4 carbon atoms alkyl Le group or Hue - Le group preferably tool -R 25 - R 25 of N (R 26 ) (R 27 ) is preferably an alkylene group having 2 to 6 carbon atoms.
  • R 26 and R 27 are preferably an alkyl group having 1 to 4 carbon atoms.
  • R 31 has the same meaning as R 21 .
  • R 32 is synonymous with R 22 .
  • X 3 is synonymous with X 2 .
  • R 41 has the same meaning as R 21 .
  • X 4 is synonymous with X 2 — N
  • R 43 (R 43 ) (R 44 ) (where R 43 and R 44 are synonymous with R 23 and R 24 ), or -R 45 -N (R 46 ) (R 47 ) (where R 45 , R 46 and R 47 are synonymous with 5 , R 26 and R 27 , respectively.
  • Specific examples of the monomer represented by the general formula (E2) include dimethyl (meth) acrylamide, jetyl (meth) acrylamide, diisopropyl (meth) acrylamide, di-n-butyl (meth) acrylamide, di- — I-butyl (meth) acrylamide, morpholino (meth) acrylamide, piperidino (meth) acrylamide, N-methyl-2-pyrrolidyl (meth) acrylamide and N, N-methylphenol (meth) acrylamide (above ( (Meth) acrylamides); 2— (N, N-dimethylamino) ethyl (meth) acrylamide, 2- (N, N-demethylamino) ethyl (meth) acrylamide, 3 -— (N, N-demethylamino) propyl (meth) acrylamide, 3 -— (N, N-dimethylamino) propyl (meth) acryl
  • Suitable examples of the polymerizable monomer having an ether group include at least one selected from monomers represented by the following general formula ( E 1 ).
  • R 11 represents a hydrogen atom or a methyl group.
  • R 12 represents an alkylene group having 1 to 8 carbon atoms, and among them, an alkylene group having 2 to 3 carbon atoms, more preferably an alkylene group having 1 to 6 carbon atoms, is more preferable.
  • X 1 represents OR 13 or one OCOR 14 .
  • R 13 represents a hydrogen atom, an alkyl group having 1 to 18 carbon atoms, a phenol group, or a phenyl group substituted with an alkyl group having 1 to 18 carbon atoms.
  • R 14 represents an alkyl group having 1 to 18 carbon atoms.
  • m3i represents 2 to 200, 5 ⁇ : L00 force preferred, 10 ⁇ : L00 force ⁇ Especially preferred! / ,.
  • the polymerizable monomer having an ether group can be appropriately selected from the usual intermediate forces without particular limitation as long as it has an ether group and is polymerizable.
  • the commercially available products include methoxypolyethylene glycol metatalylate (trade names: NK ester M-40G, M-90G, M-230G (above, manufactured by Toa Gosei Chemical Co., Ltd.); trade name: BLEMMER PME— 100, PME-200, PME-400, PME-1000, PME—2000, PME—4000 (Enomoto Yushi Co., Ltd.) Polyethylene glycol monometatalylate (trade name: Blemmer PE-90, PE 200, PE-350, manufactured by Nippon Oil & Fats Co., Ltd.), polypropylene glycol monometatalylate (trade name: Blemmer PP-500) , PP-800, PP-1000, manufactured by Nippon Oil & Fats Co., Ltd.), Polyethylene Glycol Polypropylene Glycol Monometatalylate (Brandmer 70 PEP-370B, manufactured by Nippon Oil & Fats Co., Ltd.), polyethylene glycol polytetra M
  • the graft copolymer may further contain the other monomer as a copolymer unit, and the other monomer may be appropriately selected according to the purpose without any particular limitation.
  • Aromatic vinyl compounds eg, styrene, a-methylstyrene and butyltoluene
  • acrylic acid alkyl esters eg, methyl (meth) acrylate, ethyl (meth) acrylate, n-butyl) (Meth) acrylate and i-butyl (meth) acrylate
  • (meth) acrylate alkyl aryl ester eg, benzyl (meth) acrylate
  • glycidyl (meth) acrylate carboxylate butyl ester (eg Butyl acetate and propionate)
  • cyanide butyl eg, (meth) acrylonitrile and chloroformate trityl
  • Fine aliphatic conjugated diene
  • the content of the other monomer in the graft copolymer is, for example, 5 to
  • 70% by mass is preferred. When the content is less than 5% by mass, the physical properties of the coating film may not be controlled. When the content exceeds 70% by mass, the ability as a dispersant may not be sufficiently exhibited.
  • Preferred examples of the graft copolymer include:
  • a range of normal pressure subcritical and supercritical conditions can be selected during the preparation of the organic particles, that is, there are no particular restrictions on the conditions of the poor solvent when the organic particles are deposited and formed.
  • the temperature at normal pressure is
  • the mixing method of the organic material solution (a), the poor solvent (b) of the organic material, and the polymer dispersant solution (c) is not particularly limited, and may be mixed simultaneously or sequentially. Although it is preferable to continuously add the organic material solution (a) and the polymer dispersant solution (c) to a sufficient amount of the poor solvent (b), the organic material solution (a) More preferably, and the polymer dispersant solution (c) are added simultaneously.
  • the poor solvent (b) is preferably in a stirred state.
  • the stirring speed is preferably from 100 to 10,000 rpm, more preferably from 150 to 8000 rpm, and particularly preferably from 200 to 6000 rpm! / ⁇ .
  • a pump or the like may be used, or it may not be used. Further, it may be added in liquid or outside liquid, but it is more preferable to add in liquid.
  • the mixing ratio of the organic material solution (a), the poor solvent (b), and the polymer dispersant solution (c) is preferably 1 ⁇ b / a ⁇ 20 and l ⁇ b / c ⁇ 100 in volume ratio.
  • the concentration of the resulting organic particle deposition liquid is not particularly limited as long as it is within the range where organic particles can be generated, but it is preferable that the organic particles are in the range of 10 to 40,000 mg per 1000 ml of the dispersion solvent, more preferably. It is in the range of 20 to 30000 mg, particularly preferably in the range of 50 to 2500 Omg.
  • the average particle size of organic particles there is a method of expressing the average size of the population by numerical values by measurement methods, but as a common method, the mode diameter indicating the maximum value of distribution, the integral distribution curve Median diameter corresponding to the median value of each, various average diameters (number average, length average, area In the present invention, the number average diameter is used unless otherwise specified.
  • the average particle size of the organic particles is preferably 500 m or less, more preferably 100 m or less, and particularly preferably 10 m or less.
  • the average particle diameter is preferably lnm to: m, more preferably l to 200 nm, and more preferably 2 to LOONm. It is particularly preferably 5 to 80 nm.
  • the formed particles may be crystalline particles, non-crystalline particles, or a mixture thereof.
  • the ratio ( ⁇ ) of the volume average particle size (Mv) and the number average particle size ( ⁇ ) is used as an index representing the monodispersity of the particles unless otherwise specified.
  • the organic particles (primary particles) obtained by the production method of the present invention are preferably monodispersed.
  • ⁇ / ⁇ is preferably 1.0 to 2.0, more preferably 1.0 to 1.8. 1.0 It is particularly preferred that it is ⁇ 1.5.
  • Methods for measuring the particle size of organic particles include microscopy, mass method, light scattering method, light blocking method, electrical resistance method, acoustic method, and dynamic light scattering method. Particularly preferred.
  • Examples of the microscope used for the microscopy include a scanning electron microscope and a transmission electron microscope.
  • Examples of the particle measuring apparatus using the dynamic light scattering method include Nikkiso Co., Ltd. Nanotrac UPA- ⁇ 150 (trade name), Otsuka Electronics' dynamic light scattering photometer DLS-7000 series (trade name), and the like.
  • FIG. 11 is a schematic view of a production apparatus used as an embodiment in the present invention.
  • the organic material solution is continuously supplied into the mixing chamber 13 provided in the container 11 through the supply pipe 14a and the polymer dispersant solution through the supply pipe 14b.
  • the container 11 contains a poor solvent 11a, and the mixing chamber 13 is provided below the liquid surface of the poor solvent. The inside is filled with the poor solvent.
  • the Balta poor solvent in the reaction vessel 11 is constantly convected by the stirring action in the mixing chamber 13 so that the downward force crosses the mixing chamber 13 upward (in the direction of the arrow in the figure). .
  • FIG. 1-2 is an enlarged partial cross-sectional view schematically showing an enlargement of the mixing chamber 13 as one embodiment of the manufacturing apparatus of FIG. 1-1.
  • the organic material solution is supplied into the mixing chamber 13 from the supply pipe 14a, and the polymer dispersant solution is supplied from the supply pipe 14b.
  • the mixing chamber 13 is formed by a casing (mixing chamber) 17 made of a rectangular tube having a constant cross-sectional area.
  • the upper end of the casing 17 is an open end, and a circular hole 18 is provided at the lower end.
  • the poor solvent is linked to the Balta poor solvent.
  • the organic material solution supply pipe 14a and the polymer dispersant solution supply pipe 14b are provided in a wall constituting the lower end of the casing 17, and open toward the circular hole.
  • a stirring blade 12 is provided in the mixer 13, and the stirring blade is attached to a shaft 15 and rotated by a motor (16 in FIG. 1-1). Due to the rotation of the stirring blade 12, the poor solvent is constantly circulated through the circular hole 18 in the mixer 13 downward force upward.
  • the stirring blade 12 provided in the mixing chamber 13 must produce a desired mixing strength in the mixing chamber. This mixing strength is estimated to be an important operating factor for the size of the droplets when the organic material solution and the polymer dispersant solution are mixed.
  • stirring blades 12 can be combined with other organic particles to form larger particles when the organic particles generated in the mixing space remain in the mixing chamber 13, or to the organic material solution supplied to the mixing chamber 13. It is preferable to select one that has the ability to quickly draw out the generated organic particles and quickly discharge them out of the mixing chamber 13 so that they do not become large particles due to exposure. ! /
  • any type can be used as long as the above object is achieved.
  • a turbine type, a fan turbine type or the like can be used.
  • Fig. 13 is an enlarged view of a mixing apparatus in which the mixing blades in the mixing chamber are divided into two sets (mixing blade 19a for mixing and stirring blade 19b for discharge) as another embodiment of the production apparatus of Fig. 11. FIG.
  • mixing blade 19a for mixing and stirring blade 19b for discharge
  • FIG. 11 By providing two sets of stirring blades in this way, the ability to control the mixing strength and the ability to discharge the generated organic particles out of the mixer can be selected independently. It is possible to operate by setting the circulation amount to a desired value independently.
  • FIG. 2 is a cross-sectional view schematically showing another embodiment of a production apparatus that can be used in the method for producing organic particles of the present invention.
  • the organic material solution and the poor solvent are continuously supplied into the stirring tank 21a through the supply pipes 24a and 24b, respectively.
  • the polymer dispersant solution is continuously supplied into the stirring vessel 21a from the other supply pipe 24c.
  • the organic particles generated in the stirring tank 21a remain in the stirring tank 21a, they are combined with other organic particles to become larger particles or exposed to the supplied organic material solution to become large particles.
  • the generated organic particle deposition liquid is quickly drawn out from the discharge pipe 23 so that no giant particles are generated.
  • FIG. 3 is a sectional view schematically showing still another embodiment of an apparatus that can be used in the method for producing organic particles of the present invention.
  • the stirring device 50 includes two liquid supply ports 32 and 33 through which an organic material solution and a poor solvent respectively flow in, a supply port 31 through which a polymer material solution flows in, and the stirring process is completed.
  • a cylindrical agitation tank 38 having a liquid discharge port 36 for discharging the mixed liquid, and agitation for controlling the agitation state of the liquid in the agitation tank 38 by being driven to rotate in the agitation tank 38
  • a pair of stirring blades 4 1 and 42 as means is provided.
  • the agitation tank 38 includes a cylindrical tank body 39 whose central axis is directed in the vertical direction, and a seal plate 40 serving as a tank wall that closes the upper and lower opening ends of the tank body 39. Further, the agitation tank 38 and the tank body 39 are made of a nonmagnetic material having excellent magnetic permeability.
  • the two liquid supply ports 32 and 33 are provided at a position near the lower end of the tank body 39, and the liquid discharge port 36 is provided at a position near the upper end of the tank body 39. [0208] Then, the pair of stirring blades 41, 42 are disposed apart from the opposed upper and lower ends in the stirring tank 38, and are driven to rotate in directions opposite to each other.
  • Each stirring blade 41, 42 constitutes an external magnet 46 and a magnetic coupling C arranged outside the tank wall (seal plate 40) where the stirring blade 41, 42 is close. That is, the stirring blades 41 and 42 are coupled to the respective external magnets 46 by magnetic force, and are rotated in opposite directions by being driven by the independent motors 48 and 49. Operated.
  • the pair of stirring blades 41, 42 arranged opposite to each other in the tank 38 are provided with stirring flows having different directions as indicated by the wavy arrow (X) and the solid arrow (Y) in FIG. Form in tank 38. Since the stirring flows formed by the respective stirring blades 41 and 42 have different flow directions, they collide with each other to generate a high-speed turbulent flow in the tank 38 that promotes stirring in the tank 38, 38 prevents the flow in the steady state and prevents the formation of a cavity around the rotation axis of the stirring blades 41 and 42 even when the stirring blades 41 and 42 are rotated at high speed. It is possible to prevent the inconvenience that a steady flow flowing in the tank 38 along the inner peripheral surface of the stirring tank 38 is formed without being sufficiently affected. Therefore, the processing speed can be easily improved by the high-speed rotation of the stirring blades 41 and 42, and further, the liquid flow in the tank 38 becomes steady and liquid with insufficient stirring and mixing at that time. Can be prevented, and the degradation of the processing quality can be prevented.
  • the stirring blades 41 and 42 in the stirring tank 38 are connected to the motors 48 and 49 disposed outside the stirring tank 38 by the magnetic coupling C, the rotating shaft is connected to the tank wall of the stirring tank 38.
  • the stirring tank 38 can be made into a closed container structure without the insertion part of the rotating shaft, preventing leakage of the stirred and mixed liquid to the outside of the tank, and at the same time, lubricating oil for the rotating shaft. It is possible to prevent deterioration in processing quality due to (sealing liquid) or the like being mixed into the liquid in the tank 38 as an impurity.
  • organic particles can be produced not only by the notch method but also by the continuous flow method, and can also be used for mass production. Further, the generated organic particle deposition liquid is quickly discharged, so that the ratio of the organic material solution and the poor solvent liquid supplied into the stirring tank can be kept constant. For this reason, the solubility of the organic material in the dispersion is limited from the start of manufacture to the end of manufacture. It becomes possible to make it constant, and monodispersed organic particles can be produced stably.
  • the liquid flow in the tank becomes steady and prevents the mixture liquid with insufficient stirring and mixing from being discharged, and the lubricating liquid (seal liquid) for the rotating shaft is added to the liquid in the tank as an impurity.
  • the lubricating liquid for the rotating shaft is added to the liquid in the tank as an impurity.
  • the production method of the present invention it is possible to obtain a suitable ink for ink jet recording by concentrating the organic particle deposition liquid, and therefore it is possible to produce an organic particle dispersion composition on an industrial scale. is there.
  • the concentration method is not particularly limited as long as the organic particle liquid can be concentrated.
  • (Iii) A method of concentrating organic particles by precipitation by centrifugation (iv) A drying method (a method of concentrating by sublimating the solvent by vacuum freeze-drying, a solvent by heating or decompression) Combinations of these, which are preferred to be dried and concentrated, are also preferably used.
  • the concentration of the concentrated organic particle liquid (hereinafter also referred to as “concentrated organic particle liquid”) is appropriately determined according to the application, redispersion conditions, etc., but the concentration of organic particles with respect to the total amount of concentrated organic particle liquid. Is preferably 1 to: LOO% by mass, 5 to: LO is more preferably 0% by mass, and 10 to is particularly preferably LOO% by mass.
  • the organic particles in the concentrated organic particle liquid can be obtained in a dispersed state without agglomeration, and an organic particle dispersion composition can be obtained.
  • an organic particle dispersion composition can be obtained.
  • reaggregation can be suppressed by mixing the polymer dispersant solution in a system different from the organic material solution and the poor solvent for the organic material.
  • thickening the organic material solution is very effective for facilitating the concentration process with an eye to industrial production scales. By coexisting in the solution and thickening, a desirable change in particle size can be suppressed.
  • the change in particle size due to aggregation before and after concentration depends on the organic material used, etc., but if not aggregated, the rate of particle size change (the value obtained by subtracting 1 from the value obtained by dividing the particle size after concentration by the particle size before concentration) ) Is preferably 20% or less, preferably 10% or less. More preferred ,.
  • the ultrafiltration method will be described.
  • the constant volume method in which the solvent is added continuously and the batch method in which the solvent is added intermittently, but the desalting time is relatively short.
  • the constant volume formula is preferred.
  • pure water obtained by ion exchange or distillation is used.
  • a dispersant a poor solvent for the dispersant may be mixed in pure water, or the organic particle dispersion composition may be mixed. It may be added directly.
  • FIG. 4 shows a configuration example of an apparatus for performing ultrafiltration.
  • this apparatus is equipped with a tank 81 for storing the organic particle deposition liquid, a circulation pump 82 for circulating the organic particle deposition liquid in the tank 81, and a dispersion introduced by the circulation pump 82.
  • the ultrafiltration module 83 removes the by-product inorganic salt as permeate.
  • the dispersion from which the permeate has been separated is returned to the tank 81 again, and the same operation is repeated until the predetermined purpose of removing the by-product inorganic salt is achieved.
  • this equipment is equipped with a replenishment pure water meter 84 that is used to replenish a certain amount of solvent lost by permeate as pure water.
  • Permeable water meter 85 used for measurement is installed.
  • a reverse washing pump 86 is installed to introduce water for diluting the permeate.
  • the ultrafiltration membrane flat plate type, spiral type, cylindrical type, hollow fiber type, holo fiber type, etc., which are already incorporated as modules, include Asahi Kasei Co., Ltd., Daicel Chemical Co., Ltd., Toray Co., Ltd. Nitto Denko Co., Ltd. is commercially available, but a spiral type or hollow fiber type is preferred from the viewpoint of the total membrane area and detergency.
  • the threshold value of the component that can permeate the membrane The molecular weight cut off as an index must be determined from the molecular weight of the dispersant used, but it is preferred to have a force S of 5,000 or more and 50,000 or less ⁇ , and a force S of 5,000 or more and 15,000 or less.
  • an extraction solvent is added to and mixed with the organic particle precipitate, and the organic particles are concentrated and extracted into the extraction solvent phase (the organic particle liquid after concentrated extraction is referred to as “concentrated extract”, “organic particle concentrated This is also referred to as “extract”, etc.), and is a method of concentrating the concentrated extract by filtering through a filter or the like as necessary.
  • the extraction solvent to be used is not particularly limited, but does not substantially mix with the dispersion solvent (for example, an aqueous solvent) of the organic particle precipitation liquid (in the present invention, substantially not mixed means that the compatibility is low.
  • the amount of dissolution is preferably 50% by mass or less, more preferably 30% by mass or less), and preferably a solvent that forms an interface when allowed to stand after mixing.
  • this extraction solvent must be a solvent that produces weak aggregation (re-dispersion is possible without applying high shearing force such as milling or high-speed stirring) in which organic particles can be re-dispersed in the extraction solvent. preferable. In such a state, it is possible to easily remove the dispersion solvent such as water by filter filtration while wetting the target organic particles with the extraction solvent without causing strong aggregation that changes the particle size. Is preferable.
  • the extraction solvent is preferably an ester solvent, an alcohol solvent, an aromatic solvent or an aliphatic solvent, more preferably an ester solvent, an aromatic solvent or an aliphatic solvent, and particularly preferably an ester solvent.
  • ester solvent examples include 2- (1-methoxy) propyl acetate, ethyl acetate, and ethyl lactate.
  • alcohol solvent examples include n-butanol and isobutanol.
  • aromatic solvent examples include benzene, toluene, xylene and the like.
  • aliphatic solvent examples include n-hexane and cyclohexane.
  • extraction solvent may be a pure solvent based on the above preferred solvent or a mixed solvent composed of a plurality of solvents.
  • the amount of the extraction solvent is not particularly limited as long as the organic particles can be extracted. Considering that, it is preferable that the amount is smaller than the organic particle deposition liquid. When this is represented by volume ratio, when the organic particle deposition solution is 100, the added extraction solvent is preferably in the range of 1 to: LOO, more preferably in the range of 10 to 90, and 20 to A range of 80 is particularly preferred. If the amount is too large, it takes a long time to concentrate. If the amount is too small, extraction is insufficient and particles remain in the dispersion solvent.
  • the temperature at which the extraction solvent is added and mixed is not particularly limited, but is preferably 1 to 100 ° C, more preferably 5 to 60 ° C. Any device may be used for adding and mixing the extraction solvent as long as each step can be preferably performed. For example, a separation funnel type device can be used.
  • the organic particles can be concentrated efficiently with the organic particle precipitation liquid power.
  • the concentration in the organic particle liquid after concentration can be preferably concentrated to about 100 to about LOOO times, more preferably about 500 to about LOOO times. Furthermore, almost no organic particles remain in the dispersion solvent left after extraction of the organic particles, and a high extraction rate can be achieved.
  • filter filtration apparatus for example, an apparatus such as pressure filtration can be used.
  • Preferred filters include nanofilters and ultrafilters. It is preferable to remove the remaining dispersion solvent by filtering and further concentrate the organic particles in the concentrated extract.
  • the centrifuge used for concentration of the organic particles by centrifugation may be any device as long as it can precipitate the organic particles in the organic particle precipitation liquid (or organic particle concentrated extract).
  • a centrifuge for example, in addition to a general-purpose device, one having a skimming function (a function of sucking the supernatant layer during rotation and discharging it out of the system) or a continuous centrifuge that continuously discharges solid matter. Examples include separators.
  • Centrifugation conditions are centrifugal force (a value representing the force exerted by the centrifugal acceleration of several times the gravitational acceleration) 50: LOOOO force preference ⁇ , 100-8000 force preference ⁇ , 150-6000 Masashi.
  • the temperature at the time of centrifugation is a force depending on the solvent type of the dispersion liquid—preferably 10 to 80 ° C.—preferably 5 to 70 ° C. Particularly preferably 0 to 60 ° C.
  • the apparatus used for concentration of organic particles by drying under reduced pressure is not particularly limited as long as it can evaporate the solvent of the organic particle precipitate (or organic particle concentrated extract).
  • a general-purpose vacuum dryer and rotary pump a device that can be heated and reduced in pressure while stirring the solution, and a device that can be continuously dried by passing the solution through a tube that has been heated and reduced in pressure.
  • Heating vacuum drying temperature is preferably 30-230 ° C 35-200 ° C is more preferred 40-18 0 ° C force S Especially preferred ⁇ .
  • Pressure during decompression ⁇ 100-100,000 Pa force preferred ⁇ , 300-90000 Pa force more preferred, 500-80000 Pa force particularly preferred! / ,.
  • Concentration by the reduced pressure drying method can efficiently concentrate organic particles from the organic particle precipitate, and with regard to the concentration ratio, for example, if the density of organic particles in the organic particle precipitate as a raw material is 1,
  • the density in the concentrated organic particle liquid can be concentrated to preferably about 100 to 3000 times, more preferably about 500 to 2000 times.
  • the freeze-drying method is not particularly limited, and examples thereof include a refrigerant direct expansion method, an overlapping freezing method, a heat medium circulation method, a triple heat exchange method, and an indirect heating freezing method, preferably a refrigerant direct expansion method and indirect heating freezing.
  • the method more preferably, the indirect heating freezing method is used.
  • the pre-freezing conditions are not particularly limited, but the sample strength for lyophilization must be fully frozen.
  • Indirect heating freezing equipment includes small freeze dryer, FTS freeze dryer, LYOVA C freeze dryer, experimental freeze dryer, research freeze dryer, triple heat exchange vacuum freeze dryer , Monocooling freeze dryer, HULL freeze dryer, preferably small freeze dryer, laboratory freeze dryer, research freeze dryer, monocooling freeze dryer, more preferably small freeze dryer It is preferable to use a dryer or a mono-cooling freeze dryer.
  • the temperature for lyophilization is not particularly limited, but is, for example, about ⁇ 190 to ⁇ 4 ° C., preferably about ⁇ 120 to ⁇ 20 ° C., and more preferably about ⁇ 80 to ⁇ 60 ° C.
  • the pressure of lyophilization is not particularly limited, and can be appropriately selected by those skilled in the art.
  • the freeze-drying time is, for example, 2 to 48 hours, preferably 6 to 36 hours, and more preferably about 16 to 26 hours.
  • these conditions can be appropriately selected by those skilled in the art.
  • Formulation Machine Technology Handbook Formulation Machine Technology Study Group, Jinshoshokan, P. 120-129 (September 2000); Vacuum Handbook: Nippon Vacuum Technology Co., Ltd., Ohm, p. 328-331 (199 2 years); Journal of the Research Group on Freezing and Drying: Koji Ito et al., No. 15, p. 82 (1965) can be referred to.
  • the method for producing an organic particle dispersion composition of the present invention it is preferable to use a composition from which unnecessary ions are removed.
  • the ions to be removed are not particularly limited, but it is preferable to remove ions having a small molecular weight such as sodium (Na), potassium (K), calcium (Ca), chlorine (C1) and the like.
  • the total amount of ions after removal is preferably 1% by mass or less, more preferably 0.1% by mass or less, and particularly preferably 0.01% by mass or less, relative to the organic material. Unnecessary ions can be removed using, for example, the aforementioned ultrafiltration device.
  • the concentrated organic particles can be finely dispersed again in a suitable solvent in accordance with the use such as a color filter or an ink jet ink to obtain an organic particle dispersion composition (in the present invention, fine dispersion Is to increase the degree of dispersion by deaggregating particles in the dispersion).
  • the vehicle is a medium in which organic particles are dispersed when the paint is in a liquid state.
  • the portion includes a portion that is liquid and binds to the organic particles to harden the coating film (binder), and a component that dissolves and dilutes the portion (organic solvent).
  • the organic particles may be aggregated together with the concentration in order to enable rapid filter filtration. Also, in the centrifugal separation method or the drying method, the concentrated organic particles may be aggregated in the same manner.
  • agglomerated particles mean particles such as agglomerated particles gathered by secondary force), for example, by ultrasonic waves.
  • a dispersion method or a method of capturing physical energy can be used.
  • the ultrasonic irradiation apparatus used has a function capable of applying ultrasonic waves of 10 kHz or higher.
  • examples thereof include an ultrasonic homogenizer and an ultrasonic cleaner. If the liquid temperature rises during ultrasonic irradiation, thermal aggregation of the particles occurs (see “Latest Pigment Dispersion Technology” Technical Information Association, 1995, pl66, etc.), so the liquid temperature should be 1 to LOO ° C. 5 to 60 ° C is more preferable.
  • the temperature can be controlled by controlling the temperature of the dispersion, controlling the temperature of the temperature adjusting layer that controls the temperature of the dispersion, and the like.
  • dispersing machine used to disperse the concentrated organic particles by applying physical energy.
  • kneaders roll mills, atriders, super mills, dissolvers, homomixers, sand mills, etc.
  • examples include a disperser.
  • dispersant shown in the section of [Dispersant] as the dispersant used for forming the organic particles during redispersion.
  • organic particles after redispersion can be made into finely dispersed particles.
  • it can be 1 to 200 nm, 2 to: LOOnm force S is more preferable, and 5 to 50 nm is particularly preferable.
  • the Mv / Mn of the particles after redispersion is preferably 1.0 to 2.0, more preferably 1.0 to 1.8, and particularly preferably 1.0 to 1.5.
  • the organic particle concentration of the organic particle dispersion composition after re-dispersion is appropriately determined depending on the application, etc., but for example, the amount of organic particles is preferably 0.5 to 50% by mass relative to the total amount of the composition. It is more preferable to be 1-30% by mass! /.
  • the ink for ink jet recording of the present invention it is preferable to heat-treat the organic particle dispersion composition.
  • the temperature of the heat treatment is 40-: LOO ° C is preferred, 40-90 ° C is more preferred, and 50-90 ° C is more preferred.
  • the time for the heat treatment is preferably 10 minutes to 3 days, more preferably 1 hour to 3 days, more preferably 6 hours to 2 days. During this time, the solution may be left standing or carried around.
  • the organic particle dispersion composition may further contain an aqueous solvent and other additives, and can be used as the ink for inkjet recording of the present invention.
  • the organic particles are contained in an amount of 0.2 to: LO parts by mass in 100 parts by mass of the ink jet recording ink of the present invention, more preferably 0.5 to 7.5 parts by mass.
  • the ink for ink-jet recording of the present invention includes a drying inhibitor for preventing clogging due to dry operation at an ink jetting port, a penetration accelerator for allowing the ink to penetrate better into paper, an ultraviolet absorber, and an antioxidant.
  • Viscosity modifiers, surface tension modifiers, dispersants, dispersion stabilizers, antifungal agents, antifungal agents, pH adjusters, antifoaming agents, chelating agents, etc. can be appropriately selected and used in appropriate amounts. .
  • a water-soluble organic solvent having a lower vapor pressure than water is preferred.
  • Specific examples include ethylene glycol, propylene glycol, diethylene glycol, polyethylene glycol, thiodiglycol, dithiodiglycol, 2-methyl-1,3-propanediol, 1,2,6-hexanetriol, Polyhydric alcohols typified by acetylene glycol derivatives, glycerin, trimethylolpropane, etc .; many such as ethylene glycol monomethyl (or ethyl) ether, diethylene glycol monomethyl (or ethyl) ether, triethylene glycol monoethyl (or butyl) ether Lower alkyl ethers of polyhydric alcohols; heterocyclics such as 2-pyrrolidone, N-methyl-2-pyrrolidone, 1,3-dimethyl-2-imidazolidinone, N-ethylmorpholine; sulfolane, di
  • polyhydric alcohols such as glycerin and polyethylene glycol are more preferred.
  • the aqueous solvent described above also acts as an anti-drying agent in ink for ink jet recording.
  • Anti-drying agents can be used alone or in combination of two or more. These drying inhibitors are preferably contained in the ink in an amount of 10 to 50% by mass.
  • Examples of penetration enhancers include ethanol, isopropanol, butanol, alcohols such as di (tri) ethylene glycol monobutyl ether, 1,2-hexanediol, sodium lauryl sulfate, and sodium oleate.
  • An activator or the like can be used. These are effective when contained in an amount of 10 to 30% by mass in the ink, and it is preferable to use them in a range of addition amounts without causing bleeding of the prints or paper loss (print through).
  • Examples of ultraviolet absorbers used to improve image storability include JP-A-58-185677, JP-A-61-190537, JP-A-2-782 and JP-A-5-97075.
  • Organic anti-fading agents include hydroquinones, alkoxyphenols, dialkoxyphenols, phenols, aryls, amines, indans, chromans, alkoxylins, and heterocycles.
  • complex anti-fading agents include nickel complexes and zinc complexes. More specifically, Research Disclosure No. 17643, Section VII, I through J, No. 151 62, No. 18716, left column on page 650, No. 36544, page 527, No. 307105, page 872, and the compounds cited in the patents cited in No. 15162 and JP-A-62. — Compounds represented by general formulas and compound examples of representative compounds described on pages 127 to 137 of 215272 can be used.
  • Antifungal agents include sodium dehydroacetate, sodium benzoate, sodium pyridinethiol-1-oxide, P-hydroxybenzoic acid ethyl ester, 1,2-benzisothiazolin-3-one and its salts. Can be mentioned. They 0. in the ink 02-5. 00 mass 0/0 preferably used. Details of these are described in “Encyclopedia of Antibacterial and Antifungal Agents” (edited by the Japanese Association of Antibacterial and Antifungal Society).
  • antifungal agent examples include acidic sulfites, sodium thiosulfate, ammonium thioglycolate, diisopropyl ammonium nitrite, pentaerythritol tetranitrate, dicyclohexyl ammonium nitrite, benzotriazole, and the like. These are preferably used in the ink in an amount of 0.02 to 5.00% by mass.
  • the pH adjuster can be suitably used in terms of adjusting the pH of the organic particle dispersion composition and imparting dispersion stability, and is preferably added so as to have a pH of 4.5 to 100.0. It is more preferable to add so that the pH is 6 to l 0.0.
  • the pH adjuster include basic organic bases and inorganic alkalis, and acidic ones include organic acids and inorganic acids.
  • Examples of the organic base include triethanolamine, diethanolamine, N-methyljetanolamine, and dimethylethanolamine.
  • Examples of the inorganic alkali include alkali metal hydroxides (eg, sodium hydroxide, lithium hydroxide, potassium hydroxide, etc.), carbonates (eg, sodium carbonate, sodium bicarbonate, etc.), ammonia, etc. Is mentioned.
  • Examples of the organic acid include acetic acid, propionic acid, trifluoroacetic acid, and alkyl sulfonic acid.
  • Examples of the inorganic acid include hydrochloric acid, sulfuric acid, phosphoric acid and the like.
  • Examples of the surface tension adjusting agent include a non-one, a cation, or a key-on surfactant.
  • SURFYNOLS trade name, AirProducts & Chemicals
  • acetylene-based polyoxyethylene oxide surfactant is also preferably used as these surfactants.
  • N N-dimethyl-N-alkylamine oxide
  • An amine oxide type amphoteric surfactant is also preferred.
  • the surfactants described in JP-A-59-157636, pages (37) to (38), Research Disclosure No. 308119 (1989) can also be used.
  • the surface tension of the ink of the present invention is preferably 20 to 60 mNZm with or without these! Further, 25 to 45 mNZm is preferable.
  • the viscosity of the ink for inkjet recording is preferably 30 mPa's or less, and more preferably 20 mPa's or less, and a viscosity modifier may be used for the purpose of adjusting the viscosity.
  • viscosity modifier examples include water-soluble polymer nyan-on surfactants such as celluloses and polybulal alcohol.
  • water-soluble polymer nyan-on surfactants such as celluloses and polybulal alcohol.
  • CMMC Complementary Metal Organic Chemicals
  • the above-mentioned various surfactants such as the above-mentioned cationic, char-on, and non-ionic surfactants are used as a dispersant and a dispersion stabilizer, and a fluorine-based antifoaming agent is used.
  • a silicone compound, a chelating agent typified by EDTA, and the like can be used as necessary.
  • the ink for inkjet recording can be used not only for forming a single-color image but also for forming a full-color image.
  • a magenta color ink, a cyan color ink, and a yellow color ink can be used, and a black color ink may be further used to adjust the color tone.
  • a black color ink may be further used to adjust the color tone. It is preferable that at least one of these inks having various hues is the ink for ink jet recording of the present invention because a full color image having a good hue can be formed. Further, it is more preferable that all of these various hue inks are the ink jet recording ink of the present invention, because a full color image having excellent hue can be formed.
  • Examples of the image receiving material used in the ink jet recording method include plain paper, coated paper, and plastic film. Use of coated paper as the image receiving material is preferable because image quality and image storage durability are improved.
  • plain paper oil-coated paper, for example, JP-A-8-169172, No. 8-27693, No. 2-276670, No. 7-276789, No. 9-323475, No. 62-238783, No. 10-153989, No. 10-217473, 10-235995, 10-337947, 10-217597, 10-337947, inkjet paper, film, glass, metal Ceramics or the like can be used for image formation.
  • Supports for recording paper and recording film are usually made of chemical pulp such as LBKP and NBKP, mechanical pulp such as GP, PGW, RMP, TMP, CTMP, CMP, and CGP, and waste paper pulp such as DIP.
  • Ordinary pigments, noinders, sizing agents, fixing agents, cationic agents, paper strength enhancers, and other additives are mixed and used in various devices such as long net paper machines and circular net paper machines. Is possible.
  • the thickness of the support which may be either synthetic paper or plastic film sheet, is preferably 10 to 250 111, and the basis weight is preferably 10 to 250 gZm 2 .
  • the support may be provided with an ink receiving layer and a back coat layer as it is, and may be used as an image receiving material, or after a size press or an anchor coat layer is provided with starch, polybutyl alcohol or the like, the ink receiving layer and the back coat layer are provided. It may be provided as an image receiving material. Further, the support may be subjected to a flattening treatment by a force render device such as a machine calendar, a TG calendar, or a soft calendar.
  • a force render device such as a machine calendar, a TG calendar, or a soft calendar.
  • paper and plastic films laminated on both sides with polyolefin eg, polyethylene, polystyrene, polyethylene terephthalate, polybutene and copolymers thereof
  • a white pigment for example, titanium oxide, zinc oxide
  • a tinting dye for example, cobalt blue, ultramarine blue, neodymium oxide
  • the ink receiving layer provided on the support contains a pigment and an aqueous binder.
  • white pigments examples include calcium carbonate, kaolin, talc, clay, diatomaceous earth, synthetic amorphous silica, aluminum silicate, magnesium silicate, calcium silicate, aluminum hydroxide, alumina, Examples thereof include inorganic white pigments such as litbon, zeolite, barium sulfate, sulfuric acid, titanium dioxide, zinc sulfide, and zinc carbonate, and organic pigments such as styrene pigment, acrylic pigment, urea resin, and melamine resin.
  • the white pigment contained in the ink-receiving layer is preferably a synthetic amorphous silica having a large pore area, especially a porous inorganic pigment.
  • Synthetic amorphous silica is capable of using either anhydrous silicic acid obtained by a dry production method or hydrous silicic acid obtained by a wet production method. It is particularly preferred to use hydrous silicic acid. Use two or more of these pigments together.
  • Examples of the aqueous binder contained in the ink receiving layer include polybulal alcohol, silanol-modified polybulal alcohol, starch, cationized starch, casein, gelatin, carboxymethylcellulose, hydroxyethylcellulose, polybutylpyrrolidone, Examples thereof include water-soluble polymers such as rearalkylene oxide and polyalkylene oxide derivatives, and water-dispersible polymers such as styrene butadiene latex and acrylic emulsion. These aqueous binders can be used alone or in combination of two or more. In the present invention, among these, polybulal alcohol and silanol-modified polybulal alcohol are particularly preferred in terms of adhesion to the pigment and resistance to peeling of the ink receiving layer.
  • the ink receiving layer may contain a water-resistant agent, a light-resistance improving agent, a surfactant, a hardener, and other additives.
  • the mordant added to the ink receiving layer is preferably immobilized.
  • a polymer mordant is preferably used.
  • the polymer mordant JP-A-48-28325, 54-74430, 54-124726, 55-22766, 55-14 2339, 60-23850, 60-23851, 60-23852, 60-23853, 60-57836, 60-60643, 60-118834, 60-122940, 60-122941, 60-122942, 60 -235134, JP-A-1-161236, U.S.
  • Patents 2484430, 2 describe, 3148061, 3309690, 4115124, 4124386, 4193800, 4327385, 42823 05 and 4450224, which are described in Japanese Patent Application Laid-Open No. 1-1161236, pages 212 to 215.
  • the image receiving material containing the polymer mordant is particularly preferable. When used, an image with excellent image quality can be obtained and the light fastness of the image is improved.
  • the water-resistant agent is effective for making the image water resistant.
  • Nylon resin is desirable.
  • cationic resins include polyamide polyamine epichlorohydrin, polyethyleneimine, polyamine sulfone, dimethyl diallyl ammonium chloride polymer, cationic polyacrylamide, colloidal silica, and the like.
  • the fats polyamide polyamine epichlorohydrin is particularly preferable.
  • the content of these cationic resins is preferably 1 to 15% by mass, particularly 3 to 10% by mass, based on the total solid content of the ink receiving layer.
  • the surfactant functions as a coating aid, a peelability improver, a slippage improver or an antistatic agent.
  • the surfactant is described in JP-A Nos. 62-173463 and 62-183457.
  • An organic fluoro compound may be used in place of the surfactant.
  • the organic fluoro compound is preferably hydrophobic.
  • Examples of the organic fluoro compound include a fluorine-based surfactant, an oily fluorine-based compound (eg, fluorine oil) and a solid fluorine compound resin (eg, tetrafluorinated styrene resin).
  • the organic fluoro compounds are described in JP-B-57-9053 (columns 8 to 17), JP-A-61-20994, and JP-A-62-135826.
  • the materials described on page 222 of JP-A-1-161236 can be used.
  • the ink receiving layer may be one layer or two layers.
  • the recording paper and the recording film may be provided with a knock coat layer.
  • components that can be added to this layer include a white pigment, an aqueous binder (aqueous binder), and other components.
  • white pigment contained in the knock coat layer include light calcium carbonate, heavy calcium carbonate, kaolin, talc, calcium sulfate, barium sulfate, titanium dioxide, zinc oxide, zinc sulfide, zinc carbonate, satin white, and silicic acid.
  • White inorganic pigments, styrene plastic pigments, acrylic plastic pigments, polyethylene, microcapsules, Organic pigments such as urea resin and melamine rosin are listed.
  • Examples of the aqueous binder contained in the knock coat layer include styrene / maleate copolymer, styrene Z acrylate copolymer, polybulu alcohol, silanol-modified polyvinyl alcohol, starch, cationized starch, and casein. And water-soluble polymers such as gelatin, carboxymethyl cellulose, hydroxyethyl cellulose and polybutylpyrrolidone, and water-dispersible polymers such as styrene butadiene latex and acrylic emulsion.
  • examples of other components contained in the backcoat layer include an antifoaming agent, an antifoaming agent, a dye, a fluorescent brightening agent, a preservative, and a water resistant agent.
  • a polymer latex may be added to the constituent layers (including the back layer) of the inkjet recording paper and recording film.
  • Polymer latex is used for the purpose of improving film properties such as dimensional stabilization, curling prevention, adhesion prevention, and film cracking prevention.
  • Polymer latex [described in Japanese Laid-Open Patent Publication Nos. 62-245258, 62-1316648, and 62-110066, Japanese Patent Laid-Open Nos. 62-245258.
  • Adding a polymer latex with a low glass transition temperature (40 ° C or lower) to the layer containing the mordant can prevent cracking and curling of the layer. Further, since the glass transition temperature is high, curling can be prevented even when a polymer latex is added to the back layer.
  • the ink jet recording method for example, a charge control method for ejecting ink using electrostatic attraction, a drop-on method using the vibration pressure of a piezo element Demand method (pressure pulse method), acoustic ink jet method that changes the electrical signal into an acoustic beam, irradiates the ink and ejects the ink using the radiation pressure, and the pressure generated by heating the ink to form bubbles It is used for the thermal ink jet (Bubble Jet (registered trademark)) system, etc.
  • Inkjet recording methods include a method of ejecting many low-density inks called photo inks in a small volume, a method of improving the image quality using a plurality of inks having substantially the same hue and different concentrations, and a colorless transparent ink. V for use.
  • the organic particle dispersion prepared by the organic particle precipitation method can be concentrated while suppressing aggregation of the particles, and is easy even when aggregated by concentration. Can be re-dispersed. Furthermore, according to the method for producing organic particles of the present invention, Even when the concentration of the raw material solution is high, organic particles having the above-described excellent properties can be obtained, and highly efficient organic particles can be produced.
  • an organic particle dispersion composition of the present invention it is possible to obtain a suitable inkjet ink or its raw material fine particles having sufficiently fine organic particles, excellent monodispersibility, and excellent ejection stability.
  • a pigment solution A1 was prepared by dissolving 6 g of pigment (Vigment Red 254) in a 6: 1 mixture of dimethyl sulfoxide and an 8 mol Zl aqueous potassium hydroxide solution to a pigment concentration of 150 mmol, L.
  • Methacrylic acid / benzyl methacrylate copolymer (molar ratio 28/72, weight average molecular weight: 30,000, 40% methoxy-2-propyl acetate solution) 2.
  • pigment dispersant AO. 6g, and dispersant poly 18 g of bull pyrrolidone (manufactured by Wako Pure Chemical Industries, Ltd., K30, molecular weight 40,000) was dissolved in a 1-methoxy-2-propyl acetate solution to prepare 50 ml of a polymer dispersant solution B1. Separately from this, water was prepared as a poor solvent.
  • the temperature of the solution was controlled at 1 ° C, and the pigment solution A1 was added to 1000 ml of poor solvent stirred at 500 rpm with a GK-0222-10 type lamond stirrer manufactured by Fujisawa Pharmaceutical Co., Ltd. — 200 ml was injected at a flow rate of 50 mlZmin using a KX-500 large capacity non-pulsating pump.
  • 100 ml of polymer dispersant solution B1 is injected at a flow rate of 25 mlZmin using NP-KX-500 large capacity non-pulsating flow pump manufactured by Nippon Seimitsu Chemical Co., Ltd. Were mixed to form pigment particles to prepare a pigment particle precipitation solution.
  • the prepared pigment particle deposition liquid (pigment particle concentration of about 0.5% by mass) is used to remove unnecessary ions and organic solvent by using an ultrafilter, and 400 ml of pigment particle dispersion composition (facial particle concentration) About 10.0 mass%).
  • Pigment Red 254 Dissolve 6g of Pigment (Vigment Red 254) in a 6: 1 mixture of dimethyl sulfoxide and 8molZl aqueous potassium hydroxide to prepare Pigment Solution A1 with a pigment concentration of 150mmol, L. did.
  • a pigment dispersant AO. 6 g and a dispersant polyvinyl pyrrolidone (Wako Pure Chemical Industries, Ltd., K30, molecular weight 40,000) 18 g were dissolved in a 1-methoxy-2-propyl phosphate solution to obtain a polymer.
  • 50 ml of dispersant solution B2 was prepared. Separately, water was prepared as a poor solvent.
  • the temperature of the solution was controlled at 1 ° C, and the pigment solution A1 was added to 1000 ml of poor solvent water stirred at 500 rpm by a Fujisawa Pharmaceutical Co., Ltd. GK-0222-10 type Lamond Stirrer. — 200 ml was injected at a flow rate of 50 mlZmin using a KX-500 large capacity non-pulsating flow pump.
  • the polymer dispersant solution B2 was mixed by injecting 100 ml at a flow rate of 25 mlZmin using an NP-KX-500 large capacity non-pulsating flow pump manufactured by Nippon Seimitsu Chemical Co., Ltd. to form pigment particles.
  • a precipitation solution was prepared.
  • the prepared pigment particle precipitation liquid (pigment particle concentration of about 0.5% by mass) is removed by using an ultrafilter to remove unnecessary ions and organic solvent, and concentrated to about 3 times to obtain 400 ml of pigment.
  • a particle dispersion composition (pigment particle concentration of about 10.0% by mass) was obtained.
  • Pigment (Vigment Red 254) 0.6g was dissolved in a 6: 1 mixture of dimethyl sulfoxide and 8molZl potassium hydroxide aqueous solution to adjust the pigment concentration to 150mmolZL, and the pigment dispersant AO. Dissolved to prepare pigment solution A2. Separately, water was prepared as a poor solvent.
  • the temperature of the solution was controlled at 1 ° C, and the pigment solution A2 was added to 1000 ml of poor solvent water stirred at 500 rpm with a GK-0222-10 type ramond stirrer manufactured by Fujisawa Pharmaceutical Co., Ltd. NP-KX- manufactured by Nippon Seimitsu Chemical Co., Ltd.
  • a GK-0222-10 type ramond stirrer manufactured by Fujisawa Pharmaceutical Co., Ltd.
  • NP-KX- manufactured by Nippon Seimitsu Chemical Co., Ltd.
  • the prepared pigment particle precipitation liquid (pigment particle concentration of about 0.05% by mass) is used to remove unnecessary ions and organic solvent by using an ultrafiltration machine, and is concentrated about 3 times to obtain 400 ml of A pigment particle dispersion composition (pigment particle concentration of about 1.0% by mass) was obtained.
  • a pigment solution A4 was prepared by dissolving 0.6 g of pigment (Vigment Red 254) in a 6: 1 mixture of dimethyl sulfoxide and an aqueous 8 mol Zl potassium hydroxide solution to a pigment concentration of 150 mmol ZL. Separately, the pigment dispersant AO. 3 g and the polymer dispersant polypyrrole pyrrolidone (Wako Pure Chemical Industries, Ltd., K30, molecular weight 40,000) 0.6 g dissolved in water are poor. A solvent was prepared.
  • the temperature was controlled at 1 ° C, and the pigment solution A4 was added to 1000 ml of poor solvent stirred at 500 rpm with a GK-0222-10 type Lamond Stirrer manufactured by Fujisawa Pharmaceutical Co., Ltd. NP-KX-500 type manufactured by Nippon Seimitsu Chemical Co., Ltd.
  • a GK-0222-10 type Lamond Stirrer manufactured by Fujisawa Pharmaceutical Co., Ltd.
  • NP-KX-500 type manufactured by Nippon Seimitsu Chemical Co., Ltd.
  • the prepared pigment particle deposition liquid (pigment particle concentration of about 0.05% by mass) is used to remove unnecessary ions and organic solvent by using an ultrafilter, and 400 ml of pigment particle dispersion composition (pigment particle concentration of about 1%). 0% by mass) was obtained.
  • Pigment Red 254 Dissolve 6 g of Pigment (Vigment Red 254) in a 6: 1 mixture of dimethyl sulfoxide and 8 mol Zl aqueous potassium hydroxide so that the pigment concentration is 150 mmol / L. Further, 3 g of pigment dispersant A and 6 g of a dispersant polyvinyl pyrrolidone (manufactured by Wako Pure Chemical Industries, Ltd., K30, molecular weight 40,000) were dissolved to prepare pigment solution 5. Separately, water was prepared as a poor solvent.
  • the temperature of the solution was controlled at 30 ° C, and the pigment solution A5 was added to 1000 ml of poor solvent water stirred at 500 rpm by a Fujisawa Pharmaceutical Co., Ltd. GK-0222-10 type ramond stirrer.
  • 200 ml was injected at a flow rate of 50 ml Zmin to form pigment particles to prepare a pigment particle precipitation solution.
  • the prepared pigment particle precipitation liquid (pigment particle concentration of about 0.5% by mass) is removed by using an ultrafilter to remove unnecessary ions and organic solvent, and concentrated to about 3 times to obtain 400 ml of pigment.
  • a particle dispersion composition (pigment particle concentration of about 10.0% by mass) was obtained.
  • Example 5 By separately adding a polymer dispersant solution as in the present invention (Examples 1, 2, 3, and 4), the effect of the present invention is realized even when the concentration of the pigment solution is high and the ratio of coarse particles is small. (Example 5)
  • Example 1 After the pigment particle dispersion composition obtained in Example 1 was stored at 60 ° C. for 2 weeks, there was no change in the particle size, and no precipitate was observed. Next, an ink for inkjet recording having the following composition was prepared using this pigment particle dispersion composition.
  • An image was recorded on photo glossy paper EX (manufactured by Fuji Photo Film Co., Ltd.) using an ink jet printer PM770C (trade name, manufactured by Seiko Epson Co., Ltd.) using the obtained ink.
  • the obtained image was a vivid red image with no graininess and excellent color development. Also, even after printing for one week at room temperature, nozzle clogging did not occur.
  • organic particles sufficiently fine and excellent in monodispersibility, and concentrated dispersion compositions thereof can be produced, so that they are included in inkjet ink and the like having high industrial applicability. It is used suitably for manufacture of the organic particle dispersion composition.

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  • Chemical Kinetics & Catalysis (AREA)
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  • Nanotechnology (AREA)
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Abstract

L'invention concerne un procédé de production de particules organiques qui consiste à mélanger au moins trois composants, c'est-à-dire une solution de matière organique dans un bon solvant, un solvant compatible avec le bon solvant agissant en tant que solvant médiocre pour la matière organique et une solution contenant un dispersant de poids moléculaire élevé pour former des particules de la matière organique dans la solution mélangée.
PCT/JP2006/315005 2005-07-29 2006-07-28 Procede de production de particules organiques, procede de production de compositions sous forme de dispersion de particules organiques, et encres pour imprimantes a jet d'encre contenant des compositions sous forme de dispersion de particules organiques obtenues par ledit procede WO2007013599A1 (fr)

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