WO2007060790A1 - Composition de resine colorante, encre pour impression jet d’encre et substrat de filtre colore - Google Patents

Composition de resine colorante, encre pour impression jet d’encre et substrat de filtre colore Download PDF

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Publication number
WO2007060790A1
WO2007060790A1 PCT/JP2006/320059 JP2006320059W WO2007060790A1 WO 2007060790 A1 WO2007060790 A1 WO 2007060790A1 JP 2006320059 W JP2006320059 W JP 2006320059W WO 2007060790 A1 WO2007060790 A1 WO 2007060790A1
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WIPO (PCT)
Prior art keywords
pigment
parts
group
ink
compound
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PCT/JP2006/320059
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English (en)
Japanese (ja)
Inventor
Tomonori Ikegami
Naohiro Tanaka
Dai Inagaki
Takayuki Nogami
Yoshikazu Tanaka
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Toyo Ink Manufacturing Co., Ltd.
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Application filed by Toyo Ink Manufacturing Co., Ltd. filed Critical Toyo Ink Manufacturing Co., Ltd.
Publication of WO2007060790A1 publication Critical patent/WO2007060790A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L101/00—Compositions of unspecified macromolecular compounds
    • C08L101/02—Compositions of unspecified macromolecular compounds characterised by the presence of specified groups, e.g. terminal or pendant functional groups
    • 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
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
    • B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
    • B41M3/00—Printing processes to produce particular kinds of printed work, e.g. patterns
    • B41M3/003—Printing processes to produce particular kinds of printed work, e.g. patterns on optical devices, e.g. lens elements; for the production of optical devices
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • C08L33/04—Homopolymers or copolymers of esters
    • C08L33/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, which oxygen atoms are present only as part of the carboxyl radical
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L43/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing boron, silicon, phosphorus, selenium, tellurium or a metal; Compositions of derivatives of such polymers
    • C08L43/02—Homopolymers or copolymers of monomers containing phosphorus
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D17/00—Pigment pastes, e.g. for mixing in paints

Definitions

  • Colored resin composition inkjet ink, and color filter substrate
  • the present invention is, for example, for printing by a color filter substrate, a knocker, an outdoor signboard, a colored resin composition used in paints or inks used in the manufacture of cardboard, and an ink jet method used in the above-mentioned application. Related to the inks.
  • Coatings or inks used in the manufacture of knockouts, outdoor signboards, cardboards, or color filters should be made to have a higher pigment content or higher solid content while maintaining the required resistance from the production efficiency. Is required.
  • color filters can be manufactured easily by reducing the size of the manufacturing equipment and increasing productivity by repeating the process of applying, drying, exposing, developing, and curing a conventional photoresist solution with pigment dispersed on a transparent substrate.
  • a method for producing a color filter by an ink jet method is attracting attention (see, for example, Patent Documents 1 and 2). Inks need to have a high pigment content and a high solid content, and various proposals have been made so far (for example, see Patent Document 7). It is required to maintain various resistances beyond the filter.
  • Patent Document 1 JP-A-1-217302
  • Patent Document 2 JP-A-7-174915
  • Patent Document 3 Japanese Patent Laid-Open No. 3-112992
  • Patent Document 4 Japanese Patent Laid-Open No. 9-169821
  • Patent Document 5 Japanese Patent Laid-Open No. 4-301802
  • Patent Document 6 JP-A-8-248217
  • Patent Document 7 Japanese Unexamined Patent Application Publication No. 2004-2815
  • a dispersed resin having high dispersibility In order to achieve a high pigment concentration or a high solid content of a paint or ink, it is preferable to use a dispersed resin having high dispersibility. The film or printed matter with sufficient filling cannot be obtained.
  • more cross-linking agent is used to increase resistance (for example, chemical resistance)
  • the viscosity of the paint or ink increases, and the viscosity stability over time decreases significantly. Therefore, in order to achieve high pigment concentration or high solid content in paints or inks while maintaining various resistances, a dispersed resin that maintains high dispersibility and dispersion stability and that cures efficiently with a small addition amount.
  • -A combination of crosslinking agents is required.
  • the functional group of the dispersion resin expresses the catalytic action of the crosslinking reaction of the crosslinking agent and the crosslinkability can be increased, a high pigment concentration or a high solid content can be achieved.
  • the invention is represented by a pigment, a pigment derivative, a melamine compound or a benzoguanamine compound, and one or more types of resin having a phosphate group or the following general formula (1)
  • the present invention relates to a colored resin composition containing a resin containing a monomer as a polymerization component.
  • the present invention also relates to an inkjet ink using the colored resin composition of the present invention.
  • the present invention also relates to a color filter substrate carrying a print layer made of the ink jet ink.
  • R 1 represents hydrogen or a methyl group.
  • R 2 represents an alkylene group.
  • m represents an integer of 1 to 20.
  • the melamine compound or benzoguanamine compound is preferably an alkoxyalkyl group-containing melamine compound or an alkoxyalkyl group-containing benzoguanamine compound.
  • a carboxyl group, a hydroxyl group, and Z or an aromatic ring are further contained in the rosin.
  • the pigment derivative preferably contains a triazine ring or an anthraquinone group.
  • a pigment derivative and a coating layer of the resin are preferably formed on the pigment surface. Further, it preferably contains one or more compounds selected from among epoxy compounds, phenol compounds, blocked isocyanate compounds, acrylate monomers, and silane coupling agents. Further, it preferably contains an organic solvent.
  • melamine compound and benzoguanamine compound strength pigment 6 to 2 per 100 parts by weight of pigment
  • the weight ratio of the pigment to the resin having a phosphate group is preferably from 3: 7 to 8: 2.
  • the colored resin composition of the present invention is used as a paint or ink, the cross-linking is effectively promoted, so that the chemical resistance is good.
  • the pigment concentration is high by optimizing the structure of the resin having phosphoric acid groups used in the colored resin composition of the present invention and optimizing the composition of the colored resin composition. Nevertheless, when used as a paint or ink, it has a low viscosity and good viscosity stability over time, and when used as an inkjet ink, it has low viscosity and discharge stability while maintaining its durability. Good ink can be obtained.
  • the inkjet ink of the present invention it is possible to produce a high-performance color filter substrate, no cage, outdoor signboard, etc. more efficiently than the conventional method.
  • the pigment constituting the colored rosin composition is colored to a desired hue, heat resistance, It is preferable to be excellent in chemical resistance, liquid crystal resistance and light resistance.
  • an organic pigment for example, an organic pigment, an inorganic pigment, or carbon black (for example, acetylene black, channel black, furnace black, etc.) can be used, and two or more kinds of pigments can be used in combination.
  • carbon black for example, acetylene black, channel black, furnace black, etc.
  • organic pigments include diketopyrrolopyrrole pigments, azo pigments (eg, azo, disazo, polyazo, etc.), phthalocyanine pigments (eg, copper phthalocyanine, halogenated copper phthalocyanine, metal free) Phthalocyanines, etc.), anthraquinone pigments (for example, amino anthraquinones, diaminodianthraquinones, anthrapyrimidines, flavantrons, anthanthrones, indantrons, pyrantrons, violanthrones), quinacridone pigments, dioxazine pigments, perinone pigments, perylenes Examples thereof include pigments, thioindigo pigments, isoindoline pigments, isoindolinone pigments, quinophthalone pigments, selenium pigments, and metal complex pigments.
  • azo pigments eg, azo, disazo, polyazo, etc.
  • phthalocyanine pigments eg,
  • inorganic pigments include titanium oxide, zinc white, zinc sulfide, lead white, calcium carbonate, precipitated barium sulfate, white carbon, alumina white, kaolin clay, talc, bentonite, black iron oxide, and cadmium red.
  • pigments that can be used in the colored resin composition of the present invention are indicated by color index (C.I.) numbers.
  • red coloring composition can be used in combination with a yellow pigment and an orange pigment.
  • Yellow coloring compositions include, for example, CI pigment yellow 1, 2, 3, 4, 5, 6, 1 0, 12, 13, 14, 15, 16, 17, 18, 20, 24, 31, 32, 34, 35, 35: 1, 36, 36: 1, 3 7, 37: 1, 40, 42, 43, 53, 55, 60, 61, 62, 63, 65, 73, 74, 77 81, 83, 86, 93, 94, 95, 97, 98, 100, 101, 104, 106, 108, 109, 110, 113, 114, 115, 116, 117, 118, 119, 120, 123, 125 , 126, 127, 128, 129, 137, 138, 139, 147, 148, 150, 151, 152, 153, 154, 155, 156, 161, 162, 164, 166, 16 7, 168, 169, 170, 171, 172, 173, 174, 175, 176, 177, 179, 180, 181, 182, 185, 187
  • CI pigment orange 36, 43, 51, 55, 59, 61 or the like can be used as the orange colored yarn.
  • green pigments such as CI Pigment Green 7, 10, 36, 37 can be used, for example.
  • a yellow pigment can be used in combination with the green coloring composition.
  • blue coloring composition for example, CI pigment blue 15, 15: 1, 15: 2, 15: 3, 15: 4, 15: 6, 16, 22, 60, 64, etc. should be used. Can do. Blue-colored composition Purple pigments such as C. I. Pigment Noilet 1, 19, 23, 27, 29, 30, 32, 37, 40, 42, and 50 can be used in combination.
  • These pigments can be used in combination of two or more.
  • the particle diameter of the pigment is preferably sufficiently small with respect to the wavelength of visible light from the viewpoint of the absorption coefficient of visible light (spectrum suitability) and transparency.
  • the pigment should have an average primary particle size of SO. 01 ⁇ m or more and 0.3 ⁇ m or less, particularly 0.01 ⁇ m or more and 0.1 ⁇ m or less.
  • the primary particle diameter means the diameter of the smallest unit pigment particle, and is measured with an electron microscope.
  • the primary particle diameter of the pigment can be controlled within an appropriate range using a known dispersing device such as a sand mill, an ader, or a two-roll roller.
  • P-Fn (3) (In the formula, P represents a pigment residue, F represents a basic, acidic, or neutral substituent shown below, and n represents an integer of 1 to 4)
  • Examples of the basic substituent include substituents represented by the following general formula (4), general formula (5), general formula (6), or general formula (7).
  • X represents —SO—, —CO—, —CH NHCOCH—, —CH—, or a direct bond.
  • n represents an integer of l to 10.
  • R 3 and R 4 each independently an optionally substituted alkyl group, an optionally substituted alkenyl group, an optionally substituted phenyl group, or R 3 and R 4 together Represents an optionally substituted heterocycle containing additional nitrogen, oxygen, or sulfur atoms.
  • the alkyl group and alkenyl group preferably have 1 to 10 carbon atoms! /.
  • R 5 and R 6 each independently an optionally substituted alkyl group, an optionally substituted alkenyl group, an optionally substituted phenyl group, or R 5 and R 6 together Represents an optionally substituted heterocycle containing additional nitrogen, oxygen, or sulfur atoms.
  • the alkyl group and alkenyl group preferably have 1 to 10 carbon atoms! /.
  • X represents —SO—, —CO—, —CH NHCOCH—, —CH—, or a direct bond.
  • R 7 represents an optionally substituted alkyl group, an optionally substituted alkenyl group, or a substituted! /, May! /, Or a phenyl group.
  • carbon number of an alkyl group and an alkenyl group 1-10 are preferable.
  • R 8 , R 9 , R 10 , R 11 each independently a hydrogen atom, an optionally substituted alkyl group, a substituted, an alkyl group, or a substituted! ! / Represents a phenol group.
  • carbon number of an alkyl group and an alkenyl group 1-5 are preferable.
  • X represents —SO—, —CO—, —CH NHCOCH—, —CH—, or a direct bond.
  • R 12 and R 13 each independently represents a hydrogen atom, an alkyl group that may be substituted, an alkyl group that may be substituted, or a phenyl group that may be substituted.
  • the alkyl group and the alkyl group preferably have 1 to 5 carbon atoms.
  • Z represents an alkylene group which may be substituted, an alkylene group which may be substituted, or a phenylene group which may be substituted.
  • the alkyl group and the alkyl group preferably have 1 to 8 carbon atoms.
  • P represents a substituent represented by the following general formula (8) or a substituent represented by the following general formula (9)
  • Q A hydroxyl group, an alkoxyl group, a substituent represented by the general formula (5), or a substituent represented by the general formula (6).
  • n represents an integer of l to 10.
  • R 14 and R 15 each independently an optionally substituted alkyl group, an optionally substituted alkenyl group, an optionally substituted phenyl group, or R 14 and R 15 together Represents an optionally substituted heterocycle containing additional nitrogen, oxygen, or sulfur atoms.
  • the alkyl group and alkenyl group preferably have 1 to 10 carbon atoms! /.
  • R 16 represents an optionally substituted alkyl group, an optionally substituted alkenyl group, or a substituted! /, May! /, Or a phenyl group.
  • carbon number of an alkyl group and an alkenyl group 1-10 are preferable.
  • R 17 , R 18 , R 19 , R 2 ° each independently a hydrogen atom, an optionally substituted alkyl group, a substituted, an alkenyl group, or a substituted! Yo! / Represents a phenolic group.
  • carbon number of an alkyl group and an alkenyl group 1-5 are preferable.
  • the acidic or neutral substituent include a substituent represented by the following general formula (10), general formula (11), or general formula (12).
  • M represents a hydrogen atom, a calcium atom, a barium atom, a strontium atom, a manganese atom, or an aluminum atom.
  • R 21 , R 22 , R 23 , R 24 a hydrogen atom or a carbon number] represents an alkyl group of '30 (except when all are hydrogen atoms).
  • A represents a hydrogen atom, a halogen atom, -NO, -NH, or SO H.
  • k represents an integer of 1 to 4.
  • Examples of the dye residue include diketopyrrolopyrrole dye residues, azo dye residues (eg, azo, disazo, polyazo, etc.), phthalocyanine dye residues, anthraquinone dye residues (For example, diaminodianthraquinone, anthrapyrimidine, flavantron, anthrone, indanthrone, pyranthrone, violanthrone, etc.), quinacridone dye residue, diio Xazine dye residue, perinone dye residue, perylene dye residue, thioindigo dye residue, isoindoline dye residue, isoindolinone dye residue, quinophthalone dye residue, selenium dye residue Group, metal complex dye residue, anthraquinone residue, or triazine residue.
  • diketopyrrolopyrrole dye residues eg, azo, disazo, polyazo, etc.
  • phthalocyanine dye residues eg., diamin
  • anthraquinone derivative the anthraquinone having the above basic, acidic, or neutral substituent can be used.
  • triazine derivatives include alkyl groups (eg, methyl group, ethyl group, etc.), amino groups, alkylamino groups (eg, dimethylamino group, jetylamino group, dibutylamino group, etc.), nitro groups, hydroxyl groups, alkoxy groups.
  • a group eg, methoxy group, ethoxy group, butoxy group, etc.
  • halogen eg, chlorine, etc.
  • a phenyl group optionally substituted with a methyl group, methoxy group, amino group, dimethylamino group, hydroxyl group, etc .; or It may have a substituent such as a phenylamino group which may be substituted with a methyl group, an ethyl group, a methoxy group, an ethoxy group, an amino group, a dimethylamino group, a jetylamino group, a nitro group or a hydroxyl group.
  • Derivatives in which the basic, acidic or neutral substituents are introduced into 1, 3, 5-triazine can be used. That.
  • a pigment derivative containing a triazine ring or an anthraquinone group is more preferable.
  • a pigment derivative having a triazine ring or an anthraquinone group structure exhibits a higher adsorptivity to the pigment, provides a high dispersibility, and at the same time, more effectively cures a melamine compound or a benzoguanamine compound. Can be expected to further increase resistance
  • Examples of the melamine compound or benzoguanamine compound include those having an imino group, a methylol group, or an alkoxymethyl group. Among them, a melamine compound containing an alkoxyalkyl group or a benzoguanamine compound is preferred. When a melamine compound or benzoguanamine compound containing an alkoxyalkyl group is used, the storage stability of the paint or ink containing the colored resin composition of the present invention is remarkably improved.
  • alkoxyalkyl group-containing melamine compound examples include, but are not necessarily limited to, for example, hexamethymethylol melamine or hexasuboxymethylol melamine.
  • Cymel 30 0, 301, 303, 350, 370, 325, 327, 703, 712, 01, 285, 232, 235, 236, 23 8, 211, 254, 204, 202, 207, Mycoe 506, 508, Powered by 212, 715, etc.
  • alkamine alkyl group-containing melamine compounds manufactured by Sanwa Chemical Co., Ltd.-Power Rack MW—30M, MW—30, MW—22, MS—21, MX—45, MX—500 MX-520, MX-43, MX-302, Cymel 300, 301, 303, 350, 285, 232, 235, 236, 238, and Miko 506, 508 manufactured by Nippon Cytex Industries.
  • benzoguanamine compounds include, for example, Sanwa Chemical Co., Ltd.-Power Rack BX-4000, SB-401, BX-37, SB-355, SB-303, SB301, BL ⁇ 60 SB-255, SB-203, SB-201, Cymel 1 123 manufactured by Nippon Cytex Industries, Inc., Myco Corporation 105, 106, 1128, etc.
  • alkoxyalkyl group-containing benzoguanamine compounds Sanwa Chemical Co., Ltd.-Power Rack BX-4000, SB-401, and Nihon Cytex Industry Co., Ltd. Cymel 1123 are preferable.
  • the melamine compound and the Z or benzoguanamine compound are preferably contained in an amount of 6 to 240 parts by weight based on 100 parts by weight of the pigment of the present invention. If the content is insufficient, the heat resistance and chemical resistance may be inferior. Further, when the content increases, the viscosity may increase and the storage stability may decrease.
  • the colored coffin composition of the present invention contains a coffin having a phosphate group.
  • the phosphate group is, for example, an alkali metal (eg, sodium, potassium, lithium, etc.), a polyvalent metal (eg, calcium, magnesium, aluminum, zinc, etc.), ammonia, or an organic amine ( For example, ethylamine, dibutylamine, triethanolamine, ethylamine, propylamine, butylamine, pentylamine, hexylamine, octylamine, dodecylamine, stearylamine, oleylamine, distearylamine and the like may be formed.
  • an alkali metal eg, sodium, potassium, lithium, etc.
  • a polyvalent metal eg, calcium, magnesium, aluminum, zinc, etc.
  • ammonia ethylamine, dibutylamine, triethanolamine, ethylamine, propylamine, butylamine, pentylamine, hexylamine, octylamine, dodecylamine,
  • the phosphate group contained in the coconut resin having a phosphate group can be, for example, a monovalent phosphate group represented by the formula (13) or a divalent group represented by the formula (14). It can also be a phosphate group.
  • Examples of the resin having a phosphoric acid group include monomers represented by the following general formula (1) (for example, ethylene glycol-nometamethacrylate phosphate, propylene glycolenomethacrylate phosphate, ethylene glycol acrylate). Examples thereof include vinyl polymers containing a rate phosphate or propylene glycol acrylate (phosphate) as a polymerization component.
  • monomers represented by the following general formula (1) for example, ethylene glycol-nometamethacrylate phosphate, propylene glycolenomethacrylate phosphate, ethylene glycol acrylate.
  • Examples thereof include vinyl polymers containing a rate phosphate or propylene glycol acrylate (phosphate) as a polymerization component.
  • R 1 represents hydrogen or a methyl group.
  • R 2 represents an alkylene group.
  • n represents an integer of 1 to 20.
  • These monomers having a phosphoric acid group can be produced, for example, by the methods described in JP-B-50-22536 and JP-A-58-128393.
  • Commercially available products include, for example, Phosmer M, Phosmer CL, Phosmer PE, Phosmer MH (above, manufactured by Yu-Chemical Co., Ltd.), Light Ester p-1M (Kyoeisha Co., Ltd.), JAMP-514 (Johoku Chemical Industry) KAYAMER PM-2, KAYAMERPM-21 (Nippon Kayaku Co., Ltd.) and the like.
  • these monomers having a phosphate group can be used alone or in combination of two or more.
  • the copolymerization ratio of the monomer having a phosphate group in the copolymer is preferably 0.1 to 30 parts by weight or less with respect to 100 parts by weight of all monomers, and 0.1 to 5 parts by weight or less. More preferably it is.
  • the resin further contains a hydroxyl group and a carboxyl group. Since the hydroxyl group and the carboxyl group cause a crosslinking reaction with the melamine compound, which can be easily crosslinked by the esterich reaction, the resistance is remarkably improved.
  • a method for obtaining a resin having a hydroxyl group or a carboxyl group include a method obtained by copolymerizing a monomer having a hydroxyl group or a monomer having a strong hydroxyl group with another acrylic monomer. Not limited.
  • Examples of the monomer having a hydroxyl group include 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 3-hydroxypropyl (meth) acrylate, 2-hydroxybutyl (meth).
  • Examples of the monomer having a carboxyl group include acrylic acid, methacrylic acid, crotonic acid, maleic acid, fumaric acid, itaconic acid, citraconic acid, 2-carboxyethyl acrylate, ⁇ -carboxy monopoly Examples thereof include strong prolatatone monoacrylate, monohydroxyethyl phthalate phthalate, daltaconic acid, and tetrahydrophthalic acid.
  • the resin further contains an aromatic ring.
  • Examples of the monomer having an aromatic ring include benzyl (meth) acrylate, styrene, a-methyl styrene, butyltoluene, bisphenol F ethylene oxide modified diacrylate, nourphenoxypolyethylene glycol monoacrylate, and nour.
  • R and R represent a hydrogen atom or a methyl group
  • R and R represent an alkylene group having 1 to 4 carbon atoms
  • n represents an integer of 1 to L00.
  • Examples of the monomer represented by the general formula (16) or the general formula (17) include, for example, paracumyl phenol ethylene oxide-modified acrylate, ethylene oxide-modified bisphenol A dimetatalylate, ethylene oxide-modified bisphenol A diaphthalate, Propylene oxide modified bisphenol A dimethacrylate, propylene oxide modified bisphenol A diatalate, ethylene oxide Propylene oxide modified bisphenol A dimethatalylate, ethylene oxide Propylene oxide modified bisphenol A ditalylate, propylene oxide ethylene oxide (block type) modified Bisphenol A dimethatalylate, propylene oxide tetramethylene oxide modified bisphenol A dimethata Examples thereof include relate and propylene oxide tetramethylene oxide modified bisphenol A diatalylate.
  • Monomers other than the above-mentioned monomers containing a hydroxyl group, a carboxyl group, and Z or an aromatic ring include, for example, (meth) acrylic acid alkyl esters [for example, methoxypolyethylene glycol monometatalylate, methoxypolyethylene glycol monoester] Atalylate, Otoxypolyethylene glycol monoatallylate, Otoxypolyethylene glycol polypropyleneene monomethallate, Otoxypolyethylene glycol polypropylene Glycol monotalarate, Lauroxypolyethylene glycol monoatarylate, Lau mouth Xyloxypolyethylene glycol monoacrylate, stearoxypolyethylene glycol monomethacrylate, stearoxypolyethyleneglycol polypropylene glycol monoacrylate, allyloxypolyethylene glycol polypropylene glycol monomethacrylate, allyloxypolyethylene glycol polypropylene glycol monoacrylate, ethyl Lengly
  • a monomer that is generally used for synthesizing acrylic resin such as alkyl (meth) acrylate, in which part or all of the hydrogen atoms of the alkyl group are substituted with a heterocyclic ring or a halogen atom, can also be used.
  • the weight average molecular weight (Mw) of the coffin having phosphoric acid groups is preferably 1000 to 50000, and more preferably ⁇ 2000 to 30000.
  • the polymerization initiator include organic peroxides (for example, benzoyl peroxide, tamen hydroperoxide, t-butyl hydroperoxide, diisopropyl peroxycarbonate, di-t-butyl peroxide, t butyl peroxybenzoate), or azo compounds (for example, 2, 2′-azobisisobutyrate-tolyl). It is.
  • the polymerization initiator is preferably used in an amount of 1 to 20 parts by weight with respect to 100 parts by weight of the monomer.
  • examples of the solvent used in the synthesis of rosin include, for example, acetate ester solvents (for example, ethyl cellosolve acetate, propylene glycol monomethyl ether acetate), ketone solvents (for example, cyclohexane). Xanone, methyl isobutyl ketone, etc.), xylene, or ethylbenzene.
  • acetate ester solvents for example, ethyl cellosolve acetate, propylene glycol monomethyl ether acetate
  • ketone solvents for example, cyclohexane
  • xylene or ethylbenzene.
  • resin having a phosphate group can also be used as the resin having a phosphate group.
  • examples of commercially available rosin include DISK BYK110, 111, 180 manufactured by BYK Chemi Co., Ltd., and SOLSPERS E 26000, 36600 manufactured by Avicia.
  • the present invention is used in the entire wavelength region of 400 to 700 nm in the visible light region. It is more preferable that the transmittance of the resin constituting the colored resin composition of the invention is 80% or more, more preferably 95% or more.
  • the pigment content is preferably 4 to 84% by weight based on the colored resin composition.
  • a colored resin composition having a pigment content of less than 4% by weight is used in a paint or ink to form a coating film, it may be difficult to form a coating film having a sufficient concentration. If the pigment content exceeds 84% by weight, a paint or ink having low viscosity and high dispersibility cannot be obtained when used in paints and inks, and the adhesion of the coating film cannot be secured! / I have a habit.
  • the weight ratio of pigment to resin is preferably from 3: 7 to 8: 2.
  • the content of the resin is larger than the above range, the viscosity of the paint or ink may increase because the concentration of the resin in the paint or ink using the colored resin composition of the present invention is high.
  • the content of rosin is less than the above range, the adhesion of the coating film may not be ensured.
  • the pigment preferably has a coating layer containing the pigment derivative and the resin on the surface of the pigment particles.
  • Pigments with a small primary particle size tend to cause aggregation and flocculation due to the interaction between pigments with high surface energy.
  • the pigments can interact with each other. Action is suppressed, pigment Aggregation and flow rate are reduced, and the paint or ink using the colored resin composition of the present invention has a low viscosity.
  • the coating treatment of the pigment can be performed by previously mixing the pigment, the resin, the pigment derivative, and the like so as to be uniform, and then kneading using a disperser. Additional organic solvent can be added to spread and adsorb the resin evenly on the pigment surface. It is preferable to adjust the solvent content according to the mechanical properties of the mixture.
  • Examples of the disperser used for the coating treatment of the pigment include an ader, a roll mill, a ball mill, a Banbury mixer, a roller mill, a stone mill, etc.
  • a two-roll mill is preferable because it can be mixed and kneaded in one apparatus. .
  • the solvent is not particularly limited as long as it dissolves rosin.
  • an aromatic, ester, ketone, hydrocarbon, alcohol, glycol, or other organic solvent can be used. Since the organic solvent is volatilized during the pigment coating process, the boiling point is preferably 200 ° C or lower.
  • the amount of the raw material used for coating the pigment is in the range of 1 to 30 parts by weight of the pigment derivative, 20 to 60 parts by weight of the resin, and 4 to 200 parts by weight of the solvent with respect to 100 parts by weight of the pigment. It is preferable that When the blending amount of the pigment derivative is less than 1 part by weight, the anchor effect is small, so the effect of reducing the viscosity of the paint or ink using the colored resin composition of the present invention is small. The pigment derivative becomes excessive and the unadsorbed pigment derivative aggregates, which may increase the viscosity of the paint or ink. In addition, when the blending amount of the resin is less than 20 parts by weight, the pigment surface cannot be sufficiently coated, and the dispersion stability of the pigment is lowered.
  • the free resin not adsorbed on the pigment May increase the viscosity of the paint or ink.
  • the amount of the solvent is less than 4 parts by weight, the initial coating of the pigment derivative and the resin with respect to the pigment is insufficient and the pigment is not sufficiently covered, so the viscosity of the paint or ink may not be stable. If it exceeds 200 parts by weight, it may be difficult to coat the pigment.
  • the coating treatment of the pigment is performed by, for example, the following two-stage process.
  • the first step is a tipping process in which wetting and adsorption of the resin to the pigment proceed by passing the composition containing the pigment, resin, solvent, etc. about 20 times through two rolls. In this process, About 80% by weight of the solvent is evaporated.
  • the second step is a coating treatment step in which the kneaded product in which the resin is adsorbed to the pigment by chip formation is continuously heated and kneaded to form a coating layer on the surface of the pigment particles. If the kneaded product cannot be kneaded on a machine with a high viscosity, add an appropriate amount of solvent to aid kneading.
  • the resin has a functional group capable of cross-linking
  • the resin is cross-linked in the coating treatment step, and a part of the resin is also cut.
  • This reaction is a mechanochemical reaction resulting from excessive mechanical pressurization and grinding, as well as the result of caloric heat, and the cross-linking reaction of rosin hardly occurs with only pigment and rosin.
  • the pigment derivative is used when kneading the pigment and the resin, the pigment derivative and the resin are strongly adsorbed on the surface of the pigment, and further, the crosslinking of the resin occurs by heating and pressure kneading. Presumed.
  • the heating temperature is preferably in the range of 80 ° C to 120 ° C. If the temperature is less than 80 ° C, the resin may not be sufficiently crosslinked, and if the temperature exceeds 120 ° C, the resin may be deteriorated.
  • the colored resin composition of the present invention is further added to an epoxy compound, a phenol compound, a blocked isocyanate compound, a silane coupling agent, and an acrylate monomer.
  • an epoxy compound e.g., a phenol compound, a blocked isocyanate compound, a silane coupling agent, and an acrylate monomer.
  • Examples of the epoxy compound include glycidyl ether of polyol (for example, bis ether, bisphenoxyethanol fluorenediglycidyl ether, neopentyl glycol diglycidyl ether, 1,6-hexanediol diglycidyl ether, glycerol poly).
  • polyol for example, bis ether, bisphenoxyethanol fluorenediglycidyl ether, neopentyl glycol diglycidyl ether, 1,6-hexanediol diglycidyl ether, glycerol poly.
  • Glycidyl ether trimethylolpropane polyglycidyl ether, pentaerythritol polyglycidyl ether, diglycerol polyglycidyl ether, sorbitol polyglycidyl ether, diglycidyl terephthalate, diglycidyl o-phthalate, ethylene glycol diglycidyl ether, diethylene glycol diglycidyl ether, polyethylene glycol Diglycidyl ether or polypropylene glycol monoglycidyl ether Or polyglycidyl isocyanurate, but is not necessarily limited thereto.
  • Examples of the phenolic compound include phenols and aldehydes in an acidic catalyst. Either a reacted novolak-type phenol compound or a resole-type phenol compound reacted in the presence of a basic catalyst can be used.
  • examples of phenols include ortho-cresol, para-cresol, para-phenol, para-anol, 2,3-xylenol, phenol, methacresol, 3,5-xylenol, resorcinol, catechol, hydroquinone, bisphenol A, bis-phenol.
  • Examples of aldehydes include formaldehyde and acetoaldehyde. Phenolics and aldehydes can be used alone or in combination of two or more.
  • Blocked isocyanate compounds include, for example, diisocyanates [for example, hexamethylenediocyanate, isophorone diisocyanate, toluidine isocyanate, diphenemethane 4,4'-diisocyanate, Diphenylmethane 2,4'-diisocyanate, bis (4-isocyanatecyclohexyl) methane, tetramethylxylylene diisocyanate, etc.], isocyanurates of these diisocyanates, trimethylolpropane adduct type, biuret Examples thereof include, but are not necessarily limited to, a prepolymer having an isocyanate residue (a low polymer obtained from a diisocyanate and a polyol), or uretdione having an isocyanate residue.
  • diisocyanates for example, hexamethylenediocyanate, isophorone diisocyanate, toluidine isocyanate, diphenem
  • Examples of the blocking agent include phenol (dissociation temperature of 180 ° C or higher), ⁇ -force prolactam (dissociation temperature of 160 to 180 ° C), oxime (dissociation temperature of 130 to 160 ° C), active methylene (100 ⁇ 120 ° C.) and the like, but is not necessarily limited thereto.
  • phenol dissociation temperature of 180 ° C or higher
  • ⁇ -force prolactam dissociation temperature of 160 to 180 ° C
  • oxime dissociation temperature of 130 to 160 ° C
  • active methylene 100 ⁇ 120 ° C.
  • acrylate monomer examples include various acrylic acid esters or methacrylic acid esters [for example, methyl (meth) acrylate, ethyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, 2-hydroxy Propyl (meth) acrylate, cyclohexyl (meth) acrylate, ⁇ carboxyethyl (meth) acrylate, polyethylene glycol di (meth) acrylate, 1, 6 hexanediol di (meth) acrylate, glycerol di (Meth) acrylate, triethylene glycol di (meth) acrylate, tripropylene glycol di (meth) acrylate, trimethylolpropane tri (meth) acrylate, pentaerythritol tri (meth) acrylate, 1, 6 hexane Diol diglycidyl ether di T) Atarirate, Bi Sufenol A diglycidyl ether di T
  • a polymerization initiator can be used for the purpose of further improving curability.
  • a thermal polymerization initiator can be used for the purpose of improving curability during heating, and for the purpose of improving curability by irradiation with active energy, a radical photopolymerization initiator or photopower thione polymerization is used.
  • An initiator or the like can be used.
  • thermal polymerization initiator examples include organic peroxide initiators and azo initiators.
  • photo radical polymerization initiator examples include benzophenone initiators, acetophenone initiators, thixanthone initiators, phosphine oxide initiators, and the like.
  • light-power thione polymerization initiator examples include onium salt-based initiators (eg, iodine salt, sulfur salt, etc.) and the like.
  • Examples of the silane coupling agent include bursilanes [for example, butyruris (/ 3-methoxyethoxy) silane, butylethoxysilane, butyltrimethoxysilane, etc.], (meth) acrylic silanes (for example, ⁇ —Methacryloxypropyltrimethoxysilane, etc.), epoxy silanes [eg ⁇ - (3,4-epoxycyclohexyl) ethyltrimethoxysilane, ⁇ - (3,4 epoxy cyclohexylene) methinoretrimethoxysilane J8 (3,4-epoxycyclohexyl) ethyltriethoxysilane, j8 (3,4-epoxycyclohexyl) methyltriethoxysilane, ⁇ -glycidoxypropyltrimethoxysilane, ⁇ -glycidoxypropinole Triethoxysilane, etc.
  • the epoxy compound, phenol compound, blocked isocyanate compound, acrylate monomer and the like should be contained in an amount of 6 to 240 parts by weight based on 100 parts by weight of the pigment of the present invention. Is preferred.
  • the silane coupling agent is preferably contained in an amount of 0.2 to 240 parts by weight based on 100 parts by weight of the pigment of the present invention. If the content is insufficient, the heat resistance and chemical resistance may be inferior. On the other hand, if the content exceeds 240 parts by weight, viscosity may increase and storage stability may decrease.
  • the colored resin composition may contain an organic solvent for the purpose of promoting adsorption with the pigment, the pigment derivative, and the resin, and reducing the viscosity of the composition.
  • organic solvent for example, aromatic hydrocarbons, alcohols, esters, ethers, ketons, glycol ethers, alicyclic hydrocarbons, aliphatic hydrocarbons, etc. may be used. I'll do it.
  • the colored rosin composition of the present invention In the production of the colored rosin composition of the present invention, a pigment, rosin, and, if necessary, a solvent, a pigment dispersing agent, and the like are introduced into an ordinary disperser, and a desired average particle diameter becomes a particle size distribution. To be distributed.
  • the raw materials of the colored resin composition of the present invention can be mixed and dispersed all at once, or can be mixed and dispersed separately in consideration of the characteristics and economics of each raw material.
  • the disperser for example, a sand mill, a bead mill, an agitator mill, a dyno mill, a bol mill, a kneader, a two-roll mill and the like are suitable. If each disperser has a viscosity range suitable for pigment dispersion, adjust the viscosity by changing the ratio of rosin and pigment.
  • a rosin type or surfactant type pigment dispersant can be used in order to improve the dispersibility of the pigment.
  • a rosin-type pigment dispersant has a pigment-affinity part having the property of adsorbing to a pigment and a part compatible with the dye carrier, and adsorbs to the pigment to disperse the pigment to the dye carrier. It also works to stabilize It is.
  • oleaginous pigment dispersants include, for example, polyurethanes, polycarboxylic acid esters (for example, polyatarylates), unsaturated polyamides, polycarboxylic acids, polystrength carboxylic acid (partial) amine salts, and polycarboxylic acids.
  • Ammonium salt polycarboxylic acid alkylamine salt, polysiloxane, long-chain polyaminoamide phosphate, hydroxyl group-containing polycarboxylic acid ester and their modified products, poly (lower alkylene imine) and free carboxyl group
  • Oil-based dispersants such as amides and their salts formed by reaction with polyester, (meth) acrylic acid styrene copolymer, (meth) acrylic acid (meth) acrylic acid ester copolymer, styrene maleic acid copolymer
  • Water-soluble resin such as coalesce, polybulal alcohol, polybulurpyrrolidone, water-soluble polymer compounds Polyester, modified poly Atari rate system, ethylene oxide z propylene oxide adduct I ⁇ thereof, phosphoric ester or the like is found using, they can be used alone or in combination of two or more.
  • the weight average molecular weight of the rosin type pigment dispersant is preferably about 1000 to 30000.
  • surfactant type pigment dispersant for example, naphthalene sulfonic acid formalin condensate salt, aromatic sulfonic acid formalin condensate, polyoxyethylene alkyl phosphate ester, polyoxyethylene norphenol ether, And stearylamine acetate.
  • the amount of the pigment dispersant used is preferably in the range of 1 to 30% by weight based on the colored resin composition. If the amount of the pigment dispersant used is less than 1% by weight, the effect of dispersing the pigment is not clear. If the amount exceeds 30% by weight, the film properties such as heat resistance and chemical resistance are likely to be inferior.
  • the colored resin composition of the present invention has good heat resistance and chemical resistance and is very dispersible, it is used at a high pigment concentration when used in paints or inks. Therefore, it is possible to improve the productivity and quality of a coated product or a printed product in which a high print density is desired including a color filter.
  • the colored resin composition of the present invention The product is suitable for producing a color filter that requires high productivity and quality.
  • the pigment content is preferably 2 to 40 wt% based on the ink.
  • the pigment content is less than 2% by weight, it may be difficult to form a coating film or printed matter having a sufficient concentration.
  • the pigment content exceeds 40% by weight, paints and inks with low viscosity and high dispersibility cannot be obtained when used in paints and inks, and coatings, coatings, and printed matter adhere to each other. May not be secure.
  • the solvent constituting the ink-jet ink has high solubility with respect to the resin, and when the ink is ejected by the ink-jet device, the viscosity of the solvent has a small swelling action on the device member in contact with the ink. Is preferably as low as possible.
  • the solvent is selected from the viewpoints of solubility in resin, swelling action on apparatus members, viscosity, and drying properties of the ink in the nozzle.
  • One kind can be used alone, or two or more kinds can be mixed and used.
  • alcohol solvent examples include hexanol, heptanol, octanol, nonanol, decanol, unde force nor, cyclohexanol, benzyl alcohol, and amyl alcohol.
  • glycol solvent examples include ethylene glycol monomethyl ether, ethylene glycol monoethyl enoate ethere, ethylene glycol mono monopropino ree noate, ethylene glycol mono butino enoate, ethylene glycol monomono.
  • Examples include etherate, 1-butoxyethoxypropanol, and 1-
  • ester solvent examples include ethyl acetate, lactate propane, and butyl lactate.
  • ketone solvent examples include cyclohexanone, ethyl acetate, diacetone alcohol, diisobutyl ketone, isophorone, methylcyclohexanone, and acetophenone.
  • the viscosity of the inkjet ink is preferably 2 mPa's or more and 40 mPa's or less, more preferably 3 mPa's or more and 30 mPa's or less. If the viscosity is too large, stable discharge may not be possible when discharging continuously.
  • the average dispersed particle size of the inkjet ink is preferably 5 nm or more and 200 nm or less, more preferably lOnm or more and 150 nm or less. If the average dispersed particle size is too large, the head may be clogged or stable ejection may not be possible immediately. On the other hand, if the average dispersed particle size is too small, reaggregation is likely to occur, and stability over time may deteriorate.
  • the surface tension of the inkjet ink is preferably 20 mNZm or more and 40 mNZm or less, more preferably 24 mNZm or more and 35 mNZm or less. If the surface tension is too high, the ink cannot be stably ejected from the head. Conversely, if the surface tension is too low, the ink may not be able to form droplets after ejection from the head.
  • the inkjet ink of the present invention has a high pigment concentration and a low viscosity, it has excellent ejection stability, and since the pigment content is larger than that of a normal inkjet ink, the ejection amount can be reduced. It can improve the productivity and quality of printed materials that require high print density, including those for color filter substrates.
  • the ink jet ink of the present invention is suitable for production of a color filter substrate that requires high productivity and quality.
  • the ink-jet ink of the present invention is a paper in which the ink composition penetrates in the depth direction, a blast that spreads in the lateral direction, glass, and metal. Also, the print density can be increased. Furthermore, since the discharge amount can be suppressed, it is possible to avoid the ink from flowing out and being mixed because it exceeds the ink receiving amount of the receiving layer, or the force that the dot shape becomes a perfect circle. Limited in traditional inkjet printing It can also be used for applications.
  • a color filter substrate can be produced by the inkjet method using the inkjet ink of the present invention.
  • the color filter substrate can be used, for example, in a liquid crystal display panel used in a thin television.
  • the color filter substrate is provided with a filter segment having a desired hue.
  • the filter segment is an inkjet ink for a color filter by an inkjet method in a region divided by the black matrix of the substrate on which the black matrix is formed. It is formed by discharging.
  • a glass plate or a resin plate such as polycarbonate, polymethyl methacrylate, or polyethylene terephthalate can be used.
  • the black matrix is, for example, a photolithography method in which a radical polymerization type black resist is applied, exposed, developed, and patterned, a printing method in which black ink is printed, or a vapor deposition method in which metal is deposited and then etched. Can be formed on the substrate.
  • Red pigment C.I. Pigment Red 254 ("Ilgafo RED B-CFJ" manufactured by Ciba Specialty Chemicals)
  • Green pigment C.I. Pigment Green 36 (Rionol Green 6YKJ manufactured by Toyo Ink Co., Ltd.)
  • Magenta pigment C.I. Pigment Red 122 (“Rionogen Magenta 5750” manufactured by Toyo Ink Co., Ltd.)
  • Cyan Pigment C.I.Vigment Blue 15: 3 (Toyo Ink Manufacture "Rionol Blue FG-7351J")
  • Black pigment C.I. Pigment Black 7 (Degussa “Printex 55”)
  • Pigment derivative (2) (for green, blue, cyan, black)
  • BuCBAc Diethylene glycol monobutyl ether acetate
  • a raw material was prepared in the same manner except that the raw materials were changed to the following in R1 to obtain a solution of acrylic resin having a weight average molecular weight (Mw) of 18,000 (solid content: 50%).
  • Example 1 the same procedure except that 40 parts of benzoguanamine compound (SB-401) was used instead of 40 parts of melamine compound (MX-43). I got the ink.
  • the kneaded product was formed into a sheet, cooled to room temperature, and coarsely pulverized with force to obtain 167 parts of a coated pigment.
  • Coating treatment 167 parts of pigment and 476 parts of solvent (CBAc) are placed in a sand mill and dispersed for 4 hours.
  • 40 parts of melamine compound (MX-43) and 66 parts of solvent (CBAc) are placed in a mixer and mixed. Filtration under pressure gave an ink jet ink with a pigment concentration (PC) of 13%.
  • Example 1 instead of 40 parts of melamine compound (MX-43), melamine compound (MX-417) ) An ink jet ink having a pigment concentration of 13% was obtained in the same manner except that 40 parts were added.
  • An inkjet ink having a pigment concentration (PC) of 13% was obtained in the same manner as in Example 1, except that 133 parts of the resin (R3) was added instead of 133 parts of the resin (R1).
  • An inkjet ink having a pigment concentration of 20% was obtained in the same manner as in Example 6 except that 100 parts of the resin (R1) was dispersed instead of 100 parts of the resin (R2).
  • 150 parts of the coated pigment and 250 parts of the solvent (CBAc) are mixed in a mixer, further dispersed in a sand mill, and further 40 parts of a melamine compound (MX-43), an isocyanate compound compound dessert manufactured by Bayer. 20 parts of module (BL4265) and 46 parts of solvent (CBAc) were added and mixed. The coarse particles were filtered through a filter to obtain an inkjet ink having a pigment concentration of 20%.
  • Comparative Example 2 An inkjet ink having a pigment concentration of 20% was obtained in the same manner as in Example 6 except that 100 parts of the resin (Rl) was replaced with 100 parts of the resin (R4) and dispersed.
  • An inkjet ink having a pigment concentration of 19% was obtained in the same manner as in Example 9, except that 133 parts of the resin (R1) was replaced with 133 parts of the resin (R3).
  • An inkjet ink having a pigment concentration of 12% was obtained in the same manner as in Example 10, except that 40 parts of the benzoguanamine compound (BL-60) were used instead of 40 parts of the benzoguanamine compound (SB-401).
  • An inkjet ink having a pigment concentration of 12% was obtained in the same manner as in Example 10, except that 133 parts of the resin (R1) was replaced with 133 parts of the resin (R4).
  • An inkjet ink having a pigment concentration of 15% was obtained in the same manner as in Example 13 except that 133 parts of the resin (R1) was replaced with 133 parts of the resin (R3).
  • magenta pigment 10 parts of pigment derivative (4), 133 parts of rosin (R1) and (BuCBAc) 245 Part is placed in a sand mill and dispersed for 4 hours. Furthermore, 40 parts of melamine compound (MX-43), 2 parts of silane coupling agent (KBE-403) manufactured by Shin-Etsu Chemical Co., Ltd., solvent (BuCBAc) 6 8 Part is mixed in a mixer, pressure filtered with a membrane filter, and pigment concentration (PC)
  • An inkjet ink having a pigment concentration of 17% was obtained in the same manner as in Example 14, except that 133 parts of the resin (R1) was replaced with 133 parts of the resin (R4).
  • Example 16 Same as Example 16 except that 86 parts of the resin (R1) are replaced with 86 parts of the resin (R4). Thus, an inkjet ink having a pigment concentration of 15% was obtained.
  • the ink obtained in Examples 1 to 18 and Comparative Examples 1 to 7 was ejected and dried at a predetermined position on the glass substrate using the ink jet printer, followed by heat curing at 180 ° C. for 20 minutes. A coating film was formed, and coating film reliability was evaluated by the following method. The results are shown in Tables 1 to 3.
  • the ink obtained in Examples 1 to 18 and Comparative Examples 1 to 7 was discharged onto a cardboard using the inkjet printer and dried, followed by drying at room temperature to form a coating film. It was evaluated with. The results are shown in Tables 1 to 3.
  • the viscosity (r?: MPa's) at the shear rate lOO (lZs) was measured with a dynamic viscoelasticity measuring device.
  • the dynamic viscoelasticity measuring apparatus the viscosity of the shear rate 10 (lZs) (r a: ? MPa and 'S) was measured, the viscosity of the shear rate 100 measured earlier (lZs) (r ?: mPa' s) The ratio rj aZ r? The liquidity was evaluated based on the following criteria.
  • Viscosity was measured after heating in a 45 ° C oven for 7 days.
  • ⁇ Thickening rate 10% or more and 30% or less compared to the viscosity before heating
  • the glass substrate on which the coating film was formed was immersed in N-methylpyrrolidone, and the color change ⁇ of the coating film before and after immersion was measured.
  • the printing state was visually observed, and the ejection stability was evaluated according to the following criteria.
  • ⁇ Nozzle missing after 5 minutes intermittent is 5% or less.
  • ⁇ Nozzle missing after 10 minutes intermittent is 10% or less.
  • the ink using the composition of the present invention can give good physical properties while maintaining high chemical resistance (2.0 or less). Industrial applicability
  • the colored resin composition of the present invention can be applied to, for example, paints or inks used in the production of color filter substrates, knockers, outdoor signboards, or cardboard.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Manufacturing & Machinery (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)
  • Optical Filters (AREA)

Abstract

L’invention concerne une composition de résine colorante comprenant au moins un pigment, un dérivé de pigment, un composé de mélamine ou un composé de benzoguanamine, et une résine comportant un ou plusieurs types de groupements phosphate ou une résine comprenant des unités d’un monomère représenté par une formule structurale spécifique. La composition présente une résistance chimique satisfaisante. L’optimisation de la structure de la résine et de la fabrication de la composition de résine colorante permet à la composition de présenter une faible viscosité et une viscosité stable à long terme lors d’une utilisation en tant que matériau de revêtement ou encre présentant une concentration élevée en pigment, et permet à la composition de présenter une faible viscosité et une stabilité de délivrance satisfaisante, tout en conservant sa résistance, lors d'une utilisation en tant qu'encre pour impression jet d'encre. Cette encre pour impression jet d’encre permet d’obtenir des substrats de filtre coloré, des emballages, des panneaux extérieurs, entres autres, de grande performance, de manière beaucoup plus efficace en comparaison des procédés traditionnels.
PCT/JP2006/320059 2005-11-25 2006-10-06 Composition de resine colorante, encre pour impression jet d’encre et substrat de filtre colore WO2007060790A1 (fr)

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007119836A1 (fr) * 2006-04-13 2007-10-25 Toyo Ink Mfg. Co., Ltd. Composition de résine colorée et encre pour jet d'encre comprenant celle-ci
CN102134374A (zh) * 2009-11-20 2011-07-27 新日铁化学株式会社 滤色片用组成物、硬化物及滤色片

Citations (6)

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Publication number Priority date Publication date Assignee Title
JPH0853644A (ja) * 1994-08-10 1996-02-27 Nippon Paint Co Ltd 水性コーティング組成物
JP2000239569A (ja) * 1999-02-18 2000-09-05 Kansai Paint Co Ltd 水性塗料組成物及びこの組成物を塗装した塗装物品
JP2001089696A (ja) * 1999-09-27 2001-04-03 Kansai Paint Co Ltd 塗料組成物
JP2002201378A (ja) * 2000-12-28 2002-07-19 Toyo Ink Mfg Co Ltd 顔料組成物および顔料分散体
JP2003253078A (ja) * 2002-03-04 2003-09-10 Toyo Ink Mfg Co Ltd 顔料組成物および顔料分散体
JP2004002815A (ja) * 2002-04-16 2004-01-08 Toyo Ink Mfg Co Ltd インクジェットインキおよびカラーフィルタ

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0853644A (ja) * 1994-08-10 1996-02-27 Nippon Paint Co Ltd 水性コーティング組成物
JP2000239569A (ja) * 1999-02-18 2000-09-05 Kansai Paint Co Ltd 水性塗料組成物及びこの組成物を塗装した塗装物品
JP2001089696A (ja) * 1999-09-27 2001-04-03 Kansai Paint Co Ltd 塗料組成物
JP2002201378A (ja) * 2000-12-28 2002-07-19 Toyo Ink Mfg Co Ltd 顔料組成物および顔料分散体
JP2003253078A (ja) * 2002-03-04 2003-09-10 Toyo Ink Mfg Co Ltd 顔料組成物および顔料分散体
JP2004002815A (ja) * 2002-04-16 2004-01-08 Toyo Ink Mfg Co Ltd インクジェットインキおよびカラーフィルタ

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007119836A1 (fr) * 2006-04-13 2007-10-25 Toyo Ink Mfg. Co., Ltd. Composition de résine colorée et encre pour jet d'encre comprenant celle-ci
CN102134374A (zh) * 2009-11-20 2011-07-27 新日铁化学株式会社 滤色片用组成物、硬化物及滤色片

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TW200730591A (en) 2007-08-16

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