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WO2022025034A1 - Liquide colorant, ensemble d'encres, support d'enregistrement, et procédé d'impression sur textile pour fibres hydrophobes - Google Patents

Liquide colorant, ensemble d'encres, support d'enregistrement, et procédé d'impression sur textile pour fibres hydrophobes Download PDF

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Publication number
WO2022025034A1
WO2022025034A1 PCT/JP2021/027675 JP2021027675W WO2022025034A1 WO 2022025034 A1 WO2022025034 A1 WO 2022025034A1 JP 2021027675 W JP2021027675 W JP 2021027675W WO 2022025034 A1 WO2022025034 A1 WO 2022025034A1
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WIPO (PCT)
Prior art keywords
water
ink
insoluble colorant
aqueous dispersion
maximum absorption
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/JP2021/027675
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English (en)
Japanese (ja)
Inventor
里麻 赤沼
真理子 梅田
諒 寺西
由桂 永塚
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Nippon Kayaku Co Ltd
Original Assignee
Nippon Kayaku Co Ltd
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Filing date
Publication date
Application filed by Nippon Kayaku Co Ltd filed Critical Nippon Kayaku Co Ltd
Priority to JP2022539476A priority Critical patent/JPWO2022025034A1/ja
Publication of WO2022025034A1 publication Critical patent/WO2022025034A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • 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
    • B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
    • B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
    • B41M5/00—Duplicating or marking methods; Sheet materials for use therein
    • 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
    • C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
    • C09B1/50—Amino-hydroxy-anthraquinones; Ethers and esters thereof
    • C09B1/51—N-substituted amino-hydroxy anthraquinone
    • C09B1/514—N-aryl derivatives
    • 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
    • C09B25/00—Quinophthalones
    • 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
    • C09B5/00—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings
    • C09B5/24—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings the heterocyclic rings being only condensed with an anthraquinone nucleus in 1-2 or 2-3 position
    • 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
    • C09B57/00—Other synthetic dyes of known constitution
    • C09B57/02—Coumarine dyes
    • 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
    • C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
    • 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
    • C09B67/008—Preparations of disperse dyes or solvent dyes
    • C09B67/0082—Preparations of disperse dyes or solvent dyes in liquid form
    • 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
    • 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
    • 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
    • C09D11/40—Ink-sets specially adapted for multi-colour inkjet printing
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/16—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using dispersed, e.g. acetate, dyestuffs
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/16—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using dispersed, e.g. acetate, dyestuffs
    • D06P1/20—Anthraquinone dyes
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/82—Textiles which contain different kinds of fibres
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P5/00—Other features in dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form
    • D06P5/003—Transfer printing

Definitions

  • the present invention relates to a coloring liquid, an ink set containing the coloring liquid as ink, a recording medium to which each ink contained in the coloring liquid or the ink set is attached, and a hydrophobic fiber using the coloring liquid or the ink set. Regarding the printing method.
  • hydrophobic fibers typified by polyester fibers are generally dyed with a water-insoluble coloring material. Therefore, as a water-based ink for printing hydrophobic fibers by inkjet printing, it is generally necessary to use a dispersed ink in which a water-insoluble coloring material is dispersed in water and has good performance such as dispersion stability.
  • the inkjet printing method for hydrophobic fibers is roughly divided into a direct printing method and a sublimation transfer method.
  • the direct printing method is a printing method in which an ink is directly applied (printed) to a hydrophobic fiber and then a dye in the ink is dyed on the hydrophobic fiber by a heat treatment such as high temperature steaming.
  • the sublimation transfer method ink is applied (printed) to an intermediate recording medium (dedicated transfer paper, etc.), the ink-applied surface of the intermediate recording medium is superposed on the hydrophobic fiber, and then the dye is intermediated by heat.
  • This is a printing method for transferring from a recording medium to hydrophobic fibers.
  • the sublimation transfer method is mainly used for printing of banners and the like, and an easy sublimation type dye having excellent transfer suitability to hydrophobic fibers by heat treatment is used in the ink.
  • the processing steps include (1) printing step: applying dye ink to the intermediate recording medium by an inkjet printer, and (2) transfer step: transferring and dyeing the dye from the intermediate recording medium to the fiber by heat treatment. Since two steps are included and commercially available transfer paper can be widely used, pretreatment of fibers is not required and the cleaning step is omitted.
  • Patent Document 1 describes a water-soluble organic solvent as a moisturizing agent (anti-drying agent) for a dye dispersion liquid in which a water-insoluble dye selected from a disperse dye and an oil-soluble dye is dispersed in water with a dispersant.
  • Surfactant as a surface tension adjuster, and other additives (pH adjuster, antiseptic dye, defoamer, etc.) are added, and physical properties (physical properties) such as particle size, viscosity, surface tension, pH, etc. It is described that the water-based ink is prepared by optimizing.
  • an inkjet paper having an ink receiving layer formed on the surface by inorganic fine particles such as silica and having a relatively large basis weight and capable of applying a large amount of ink is generally used. It is used.
  • transfer papers having a smaller basis weight and transfer papers having a smaller ink receiving layer have been used, and there is a strong demand for achieving high transfer efficiency and dyeing density (color development) with a small amount of ink.
  • the present invention is a novel coloring liquid suitably used for a sublimation transfer method, an ink set containing the coloring liquid as ink, the coloring liquid or a recording medium to which each ink contained in the ink set is attached, and the coloring liquid or the coloring liquid.
  • An object of the present invention is to provide a method for printing hydrophobic fibers using the ink set.
  • the polarity term of the Hansen solubility parameter is 11 MPa 0.5 or more and less than 12.6 MPa 0.5 ;
  • B) Contains a water-insoluble colorant C different from the water-insoluble colorant B, which has a maximum absorption wavelength in the wavelength range of 410 nm or more and 450 nm or less;
  • C) Contains at least two water-insoluble colorants other than the water-insoluble colorant A;
  • D) Contains a phytosterol compound; A coloring liquid that satisfies at least one of the above conditions.
  • the polar term of the Hansen solubility parameter of the water-insoluble colorant A is 11 MPa 0.5 or more and less than 12.6 MPa 0.5
  • the hydrogen bond term is 7 MPa 0.5 or more and 10 MPa 0.5 or less 1) to 3 ).
  • the coloring liquid according to any one of the items.
  • the water-insoluble colorant F has the following formula (F1): The coloring liquid according to any one of 11) to 13), which comprises the compound represented by.
  • the dispersant comprises a styrene- (meth) acrylic copolymer, a formarin condensate of aromatic sulfonic acid or a salt thereof, polyoxyethylene arylphenyl ether, polyoxyethylene arylphenyl ether sulfate, and polyoxyethylene naphthyl ether.
  • the coloring solution according to 15 which comprises at least one selected from the group.
  • Ink B containing Disperse Yellow 54 and phytosterol compounds (F) The following formula, which has a maximum absorption wavelength in the wavelength range of 380 nm or more and 500 nm or less, and b * represented by the CIE color space when the absorbance at the maximum absorption wavelength is 1 is in the range of 65 to 80.
  • B1 [In the formula, RB represents a hydrogen atom, a cyano group, a nitro group, a halogen atom, an alkyl group having 1 to 8 carbon atoms, a substituted or unsubstituted amino group, an alkoxy group, or an aryloxy group, and X B is Indicates a hydrogen atom or a halogen atom.
  • ink C containing a water-insoluble colorant B represented by;
  • Ink D containing a water-insoluble colorant G having a maximum absorption wavelength in a wavelength range of 560 nm or more and less than 660 nm (provided that CI Disperse Violet 27 or CI Disperse Violet 28 is contained. Includes); An ink set that meets at least one of the conditions.
  • the droplets of the coloring liquid according to any one of 1) to 18) or the droplets of each ink contained in the ink set according to any one of 19) to 28) are attached to the intermediate recording medium.
  • the printing process to obtain the recorded image A transfer step of transferring the recorded image to the hydrophobic fiber by bringing the hydrophobic fiber into contact with the adhering surface of the coloring liquid or the ink in the intermediate recording medium and heat-treating it.
  • Method for printing hydrophobic fibers including.
  • a novel coloring liquid suitably used for a sublimation transfer method, an ink set containing the coloring liquid as ink, a recording medium to which the coloring liquid or each ink contained in the ink set is attached, and the coloring. It is possible to provide a method for printing hydrophobic fibers using a liquid or the ink set.
  • the maximum absorption wavelength and chromaticity of the water-insoluble colorant are set so that the water-insoluble colorant is dissolved or dispersed in dimethylformamide (DMF) so that the absorbance of the maximum absorption wavelength in ultraviolet-visible spectroscopic absorption becomes 1. Measure the concentration-adjusted solution. Further, in the present specification, each component such as a water-insoluble colorant may be used alone or in combination of two or more. In this specification, "CI" is an abbreviation for Color Index.
  • the coloring liquid according to this embodiment includes the following (i) and (ii): (I)
  • the b * represented by the CIE color space is in the range of -30 to -20 when the maximum absorption wavelength is in the wavelength range of more than 640 nm and 700 nm or less and the absorbance at the maximum absorption wavelength is 1.
  • the polarity term of the Hansen solubility parameter is 11 MPa 0.5 or more and less than 12.6 MPa 0.5 ;
  • B) Contains a water-insoluble colorant C different from the water-insoluble colorant B, which has a maximum absorption wavelength in the wavelength range of 410 nm or more and 450 nm or less;
  • C) Contains at least two water-insoluble colorants other than the water-insoluble colorant A;
  • D) Contains a phytosterol compound; At least one of the conditions is satisfied.
  • RB represents a hydrogen atom, a cyano group, a nitro group, a halogen atom, an alkyl group having 1 to 8 carbon atoms, a substituted or unsubstituted amino group, an alkoxy group, or an aryloxy group
  • X B is Indicates a hydrogen atom or a halogen atom.
  • water-insoluble colorant in the present embodiment examples include pigments, disperse dyes, oil-soluble dyes, and the like, and disperse dyes and oil-soluble dyes are preferable.
  • water-insoluble colorant A will be described first, then the conditions (a) to (d) will be described, and then other matters will be described.
  • the water-insoluble colorant A has the following (i) and (ii): (I) The b * represented by the CIE color space is in the range of -30 to -20 when the maximum absorption wavelength is in the wavelength range of more than 640 nm and 700 nm or less and the absorbance at the maximum absorption wavelength is 1. ; (Ii) The polarity term of the Hansen solubility parameter is 11 MPa 0.5 or more and less than 12.6 MPa 0.5 ; At least one of the conditions is satisfied.
  • the water-insoluble colorant A satisfies the above condition (i)
  • the water-insoluble colorant A preferably has a maximum absorption wavelength in the wavelength range of 660 nm or more and 700 nm or less, and has a maximum absorption wavelength in the wavelength range of 660 nm or more and 690 nm or less. It is more preferable to have.
  • the Hansen solubility parameter is a solubility parameter introduced by Hildebrand divided into three components: a dispersion term delta D, a polar term delta P, and a hydrogen bond term delta H.
  • the Hansen solubility parameter can be estimated from the contents and average molecular weights of hydrogen atoms, carbon atoms, oxygen atoms and the like constituting the molecule using Hansen Solubility Parameters in Practice (HSPiP), which is computer software.
  • the hydrogen bond term of the Hansen solubility parameter is preferably 7 MPa 0.5 or more and 10 MPa 0.5 or less.
  • the water-insoluble colorant A is not particularly limited as long as it satisfies at least one (preferably both) of the above conditions (i) and (ii), but one having an anthraquinone structure is preferable, and one having a molecular weight of 340 or more is more preferable. preferable.
  • water-insoluble colorant A satisfying the above conditions (i) and (ii) include, for example, C.I. I. Disperse Blue 60, 87, 143, 181, 334; C.I. I. Solvent blue 67; a compound represented by the following formula (A1); and the like.
  • R 1A to R 3A each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.
  • the alkyl group may have an alkoxy group as a substituent.
  • C.I. I. Disperse blue 60 and compounds represented by the following formulas (A1-1) to (A1-3) are preferable, and compounds represented by the following formulas (A1-1) or (A1-2) are more preferable, and the following compounds are more preferable.
  • the compound represented by the formula (A1-2) is more preferable.
  • the compound represented by the following formula (A1-1) is C.I. I. Also known as Disperse Blue 334.
  • the water-insoluble colorant A and other water-insoluble colorants described below may be powdery or lumpy dry colorants, or may be wet cakes or slurries. .. Further, a dispersant such as a surfactant may be contained in a small amount for the purpose of suppressing the aggregation of the coloring material particles during or after the coloring material synthesis.
  • Commercially available dyes have grades for industrial dyeing, resin coloring, ink, toner, inkjet, etc., and their manufacturing methods, purity, particle size, etc. are different from each other. In order to suppress the cohesiveness after pulverization, a color material having smaller particles is preferable, and a material having as few impurities as possible is preferable from the viewpoint of the influence on the dispersion stability and the ejection accuracy of the ink.
  • the above condition (a) is represented by a CIE color space when the coloring liquid according to the present embodiment has a maximum absorption wavelength in a wavelength range of 380 nm or more and 500 nm or less, and the absorbance at the maximum absorption wavelength is 1.
  • * Contains the water-insoluble colorant B represented by the following formula (B1), which is in the range of 65 to 80.
  • RB represents a hydrogen atom, a cyano group, a nitro group, a halogen atom, an alkyl group having 1 to 8 carbon atoms, a substituted or unsubstituted amino group, an alkoxy group, or an aryloxy group
  • X B is Indicates a hydrogen atom or a halogen atom.
  • examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom, and a chlorine atom is preferable.
  • alkyl group having 1 to 8 carbon atoms examples include a linear alkyl group such as a methyl group, an ethyl group, an n-propyl group, an n-butyl group and an n-octyl group; an isopropyl group, a sec-butyl group and a tert.
  • a linear alkyl group such as a methyl group, an ethyl group, an n-propyl group, an n-butyl group and an n-octyl group
  • -A branched chain alkyl group such as a butyl group
  • a cyclic alkyl group such as a cyclopentyl group or a cyclohexyl group
  • substituted or unsubstituted amino group examples include an amino group, a methylamino group, an ethylamino group, a phenylamino group, a dimethylamino group, a diethylamino group, a diphenylamino group, a methylphenylamino group and the like, which are diethylamino groups. Is preferable.
  • the above-mentioned substituted amino group may further have an arbitrary substituent.
  • alkoxy group examples include a methoxy group, an ethoxy group, a propoxy group, an n-butoxy group, a sec-butoxy group, a tert-butoxy group and the like.
  • the alkoxy group may have any substituent.
  • aryloxy group examples include a phenoxy group and a naphthoxy group.
  • the aryloxy group may have any substituent.
  • water-insoluble colorants B represented by the above formula (B1) those in which RB is a substituted or unsubstituted amino group and X B is a halogen atom are preferable, and are represented by the following formula (B1-1). Compounds are more preferred.
  • the compound represented by the following formula (B1-1) is C.I. I. Disperse Yellow 232, C.I. I. Solvent Yellow 160: 1, C.I. I. Disperse Yellow 184: 1 etc.
  • the compound represented by the above formula (B1) is, for example, Ayyangar N. et al. According to the method of R et al. (Ayyangar N.R. et al., Days and Pigments, 991, 16 (3), 197-204), the compound represented by the following formula (B2) and the compound represented by the following formula (B3) are represented. It can be obtained by subjecting the compound to a condensation reaction.
  • the total content of the water-insoluble colorant under the condition (a) is preferably 0.1 to 40% by mass, preferably 0.5 to 25% by mass, based on the total amount of the coloring liquid according to the present embodiment. It is more preferable to have.
  • the above condition (b) is that the coloring liquid according to the present embodiment contains a water-insoluble coloring agent C different from the water-insoluble coloring agent B, which has a maximum absorption wavelength in the wavelength range of 410 nm or more and 450 nm or less. ..
  • a highly saturated green can be expressed.
  • C.I. I. Disperse Yellow 54, 82, 232 is preferred, and C.I. I. Disperse Yellow 54 is more preferable.
  • the a * value represented by the CIE color space is in the range of -25 to -10 when the absorbance at the maximum absorption wavelength is 1.
  • the content of the water-insoluble colorant C is preferably, for example, 1 to 200 parts by mass, and more preferably 1 to 150 parts by mass, when the content of the water-insoluble colorant A is 100 parts by mass. preferable.
  • the above condition (c) is that the coloring liquid according to the present embodiment contains at least two kinds of water-insoluble coloring agents other than the water-insoluble coloring agent A, and at least three kinds other than the water-insoluble coloring agent A. It preferably contains a water-insoluble colorant.
  • the coloring liquid satisfying the above condition (c) is, for example, a water-insoluble colorant D having a maximum absorption wavelength in a wavelength range of more than 450 nm and 590 nm or less, and a water-insoluble colorant having a maximum absorption wavelength in a wavelength range of more than 590 nm and 640 nm or less.
  • the coloring liquid according to the present embodiment contains the water-insoluble colorants A, D, and E, for example, a printed material having excellent color-developing property can be obtained. Further, by containing the water-insoluble colorants A, C, D, and E in the coloring liquid according to the present embodiment, for example, the hue change due to the influence of the color rendering property is suppressed, and the black color is excellent in color rendering property. You can get the printed material.
  • water-insoluble colorant D examples include, for example, C.I. I. Disperse Orange 21, 25, 42, 44, 45, 56, 72, 76, 80, 88, 96, 145; C.I. I. Disperse Brown 26, 27; C.I. I.
  • C.I. I. Disperse Orange 25; C.I. I. Disperse thread 60; C.I. I. Disperse Brown 27; C.I. I. Disperse Violet 17, 27, 28; C.I. I. Disperse Blue 72; C.I. I. Solvent Violet 13 is preferred, and C.I. I. Disperse brown 27 is more preferable.
  • C.I. I. Disperse Blue 72 is C.I. I. Also called Solvent Violet 13.
  • the water-insoluble colorant D preferably has an a * value in the range of 15 to 35 in the CIE color space when the absorbance at the maximum absorption wavelength is 1.
  • water-insoluble colorant E examples include, for example, C.I. I. Disperse Blue 19, 26, 27, 54, 55, 56, 64, 73, 77, 81, 128, 148, 149, 153, 158, 165, 165: 1, 165: 2, 183, 197, 224, 225 257, 268, 287, 337, 345, 360; C.I. I. Solvent Blue 35, 36, 78, 111, 112; C.I. I. Solvent Violet 13; etc. may be mentioned. Among these, C.I. I. Disperse Blue 360, C.I. I. Solvent Violet 13 is preferred, and C.I. I. Disperse blue 360 is more preferable.
  • the content of the water-insoluble colorant C is when the content of the water-insoluble colorant A is 100 parts by mass.
  • it is preferably 3 to 70 parts by mass, and more preferably 35 to 45 parts by mass.
  • the content of the water-insoluble colorant D is preferably, for example, 150 to 400 parts by mass, preferably 240 to 320 parts by mass, when the content of the water-insoluble colorant A is 100 parts by mass. Is more preferable.
  • the content of the water-insoluble colorant E is preferably, for example, 80 to 350 parts by mass, and 180 to 280 parts by mass, when the content of the water-insoluble colorant A is 100 parts by mass. Is more preferable.
  • the content of the water-insoluble colorant A, C, D, and other water-insoluble colorants other than E is, for example, 500 parts by mass or less when the content of the water-insoluble colorant A is 100 parts by mass. It is preferably 300 parts by mass or less, and more preferably 300 parts by mass or less.
  • the mass-based content of the water-insoluble colorant A is (A) and the mass-based content of the water-insoluble colorants C and E is (C + E), it is calculated by (A) / (C + E).
  • the value is preferably less than 0.8, more preferably 0.03 or more and less than 0.8, further preferably more than 0.03 and 0.75 or less, and 0.05 or more and 0. It is particularly preferably 75 or less, and extremely preferably 0.1 or more and 0.7 or less.
  • the above condition (d) is that the coloring liquid according to the present embodiment contains a phytosterol compound.
  • the coloring liquid satisfying the above condition (d) preferably contains, for example, a water-insoluble colorant F having a maximum absorption wavelength in a wavelength range of 560 nm or more and 600 nm or less, and a phytosterol compound.
  • a cyan-colored printed material having good light fastness, suppression of streaks and unevenness, and excellent color development. Can be obtained.
  • the water-insoluble colorant F is not particularly limited, but one having an anthraquinone structure is preferable, and b * represented by the CIE color space when the absorbance at the maximum absorption wavelength is 1 is within the range of -65 to -55. It is more preferable that the molecular weight is in the range of 300 to 400.
  • the water-insoluble colorant F include a compound represented by the following formula (F1); C.I. I. Disperse Blue 72; C.I. I. Disperse Violet 8, 27, 28, 47, 77, 97, 98; C.I. I. Solvent violet 13, 14, 31, 36; and the like.
  • the compound represented by the following formula (F1) is preferable.
  • the compound represented by the following formula (F1) is C.I. I. Disperse Blue 72, C.I. I. Also called Solvent Violet 13 etc.
  • the content of the water-insoluble colorant F is, for example, 10 to 150 when the content of the water-insoluble colorant A is 100 parts by mass. It is preferably parts by mass, more preferably 20 to 80 parts by mass.
  • phytosterol compound examples include an alkylene oxide adduct of phytosterol or hydrogenated phytosterol (hereinafter, both are collectively referred to as "phytosterols").
  • the phytosterol alkylene oxide adduct As the phytosterol alkylene oxide adduct, the phytosterol C2-C4 alkylene oxide adduct is preferable, and the ethylene oxide adduct is more preferable.
  • the amount of alkylene oxide (preferably C2-C4 alkylene oxide, more preferably ethylene oxide) added per mol of phytosterols is preferably about 10 to 50 mol, and the HLB is preferably about 13 to 20 mol.
  • phytosterol compounds include, for example, NIKKOL BPS-20, NIKKOL BPS-30 (both manufactured by Nikko Chemicals Co., Ltd., phytosterol ethylene oxide adduct), and NIKKOL BPSH-25 (hydrogenated phytosterol ethylene oxide adduct). Things) and the like, and NIKKOL BPS-30 is preferable.
  • the content of the phytosterol compound is preferably 0.001 to 10% by mass, more preferably 0.01 to 7% by mass, and 0.1 to 0.1% by mass, based on the total amount of the coloring liquid according to the present embodiment. It is more preferably to 3% by mass, particularly preferably 0.2 to 1% by mass, and extremely preferably 0.3 to 0.6% by mass.
  • the coloring liquid according to this embodiment preferably further contains a dispersant.
  • Dispersants include, for example, styrene- (meth) acrylic copolymers, formalin condensates of aromatic sulfonic acids or salts thereof, polyoxyethylene arylphenyl ethers, polyoxyethylene arylphenyl ether sulfates, and polyoxyethylene naphthyl ethers. It is preferable to contain at least one selected from the group.
  • the styrene- (meth) acrylic copolymer is a copolymer of a styrene-based monomer and a (meth) acrylic-based monomer.
  • Specific examples of the copolymer include ( ⁇ -methyl) styrene-acrylic acid copolymer, ( ⁇ -methyl) styrene-acrylic acid-acrylic acid ester copolymer, and ( ⁇ -methyl) styrene-methacrylic acid copolymer.
  • ( ⁇ -methyl) styrene-methacrylic acid-acrylic acid ester copolymer ( ⁇ -methyl) styrene-acrylic acid ester- (anhydrous) maleic acid copolymer, acrylic acid ester-styrene sulfonic acid copolymer, Examples thereof include a ( ⁇ -methyl) styrene-methacrylic sulfonic acid copolymer.
  • (meth) acrylic is used as a meaning including “acrylic” and “methacryl”.
  • ( ⁇ -methyl) styrene” is used as a meaning including " ⁇ -methylstyrene” and "styrene”.
  • the mass average molecular weight of the styrene- (meth) acrylic copolymer is, for example, preferably 1000 to 20000, more preferably 2000 to 19000, and even more preferably 5000 to 17000.
  • the mass average molecular weight of the styrene- (meth) acrylic copolymer can be measured by a GPC (gel permeation chromatograph) method.
  • the acid value of the styrene- (meth) acrylic copolymer is, for example, preferably 50 to 250 mgKOH / g, more preferably 100 to 250 mgKOH / g, and even more preferably 150 to 250 mgKOH / g.
  • the acid value of the resin represents the number of mg of KOH required to neutralize 1 g of the resin, and can be measured according to JIS-K3054.
  • the glass transition temperature of the styrene- (meth) acrylic copolymer is, for example, preferably 45 to 135 ° C, more preferably 55 to 120 ° C, still more preferably 60 to 110 ° C.
  • styrene- (meth) acrylic copolymer examples include, for example, Joncryl 67, 678, 680, 682, 683, 690, 52J, 57J, 60J, 63J, 70J, JDX-6180, HPD-196, HPD96J, Examples thereof include PDX-6137A, 6610, JDX-6500, JDX-6369, PDX-6102B, PDX-6124 (all manufactured by BASF) and the like.
  • Joncryl 67 mass average molecular weight: 12500, acid value: 213 mgKOH / g
  • 678 mass average molecular weight: 8500, acid value: 215 mgKOH / g
  • 682 mass average molecular weight: 1700, acid value: 230 mgKOH / g).
  • 683 mass average molecular weight: 4900, acid value: 215 mgKOH / g
  • 690 mass average molecular weight: 16500, acid value: 240 mgKOH / g
  • Joncryl 678 is more preferable.
  • formalin condensate of aromatic sulfonic acid or a salt thereof examples include cleosort oil sulfonic acid, cresol sulfonic acid, phenol sulfonic acid, ⁇ -naphthalene sulfonic acid, ⁇ -naphthol sulfonic acid, ⁇ -naphthalin sulfonic acid, and benzene sulfonic acid.
  • formalin condensates such as acid, cresol sulfonic acid, 2-naphthol-6-sulfonic acid, lignin sulfonic acid, and methylnaphthalene sulfonic acid, or salts thereof (sodium salt, potassium salt, lithium salt, etc.).
  • cleosort oil sulfonic acid ⁇ -naphthalene sulfonic acid, lignin sulfonic acid, methylnaphthalene sulfonic acid formalin condensates or salts thereof are preferable.
  • Examples of the formalin condensate of the special aromatic sulfonic acid or a salt thereof include Demor SN-B (manufactured by Kao Corporation).
  • Examples of the formalin condensate of methylnaphthalene sulfonic acid or a salt thereof include Laberin AN series (manufactured by Dai-ichi Kogyo Seiyaku Co., Ltd.) and the like.
  • Demor N, Laberin AN series, and Labelin W series are preferable, Demor N and Labelin W series are more preferable, and Labelin W series is further preferable.
  • Examples of the lignin sulfonic acid include Vanillex N, Vanillex RN, Vanillex G, Pearllex DP (all manufactured by Nippon Paper Industries, Ltd.) and the like. Of these, Vanillex RN, Vanillex N, and Vanillex G are preferred.
  • polyoxyethylene arylphenyl ether examples include styrylphenol compounds such as polyoxyethylene styrylphenyl ether, polyoxyethylene distyrylphenyl ether, polyoxyethylene tristylylphenyl ether, and polyoxyethylene tetrastyrylphenyl ether; polyoxyethylene.
  • styrylphenol compounds such as polyoxyethylene styrylphenyl ether, polyoxyethylene distyrylphenyl ether, polyoxyethylene tristylylphenyl ether, and polyoxyethylene tetrastyrylphenyl ether; polyoxyethylene.
  • Benzylphenol compounds such as benzylphenyl ether, polyoxyethylene dibenzylphenyl ether, polyoxyethylene tribenzylphenyl ether; cumylphenol compounds such as polyoxyethylene cumylphenyl ether; polyoxyethylene naphthylphenyl ether, polyoxyethylene biphenyl Examples include ether, polyoxyethylene
  • the number of repetitions of the polyoxyethylene group in the polyoxyethylene arylphenyl ether is preferably 1 to 30, more preferably 15 to 30.
  • the number of repetitions is 1 or more, the compatibility with an aqueous solvent or the like tends to be excellent. Further, when the number of repetitions is 30 or less, the viscosity tends not to be too high.
  • polyoxyethylene styrylphenyl ether is preferable.
  • Commercially available products of polyoxyethylene styrylphenyl ether include, for example, Pionin D-6112, Pionin D-6115, Pionin D-6120, Pionin D-6131, Pionin D-6512, Takesurf D-6413, DTD-51, Pionin D.
  • polyoxyethylene aryl phenyl ether sulfate examples include the above-mentioned sulfate of polyoxyethylene aryl phenyl ether.
  • polyoxyethylene styrylphenyl ether sulfate is preferable.
  • examples of commercially available products of polyoxyethylene styrylphenyl ether sulfate include SM-57 and SM-210 (all manufactured by Toho Chemical Industry Co., Ltd.).
  • Examples of commercially available products of polyoxyethylene naphthyl ether include Neugen EN series (manufactured by Dai-ichi Kogyo Seiyaku Co., Ltd.) and Pionin D-7240 (manufactured by Takemoto Oil & Fat Co., Ltd.).
  • the alkylene oxide adduct of cholestanols As the alkylene oxide adduct of cholestanols, the C2-C4 alkylene oxide adduct of cholestanols is preferable, and the ethylene oxide adduct is more preferable.
  • the amount of alkylene oxide (preferably C2-C4 alkylene oxide, more preferably ethylene oxide) added per mol of cholestanols is preferably about 10 to 50 mol, and the HLB is preferably about 13 to 20 mol.
  • the coloring liquid according to this embodiment preferably further contains a surfactant.
  • the surfactant include known surfactants such as anion, cation, amphoteric, nonionic, silicone-based, and fluorine-based.
  • anionic surfactant examples include an alkyl sulfonate, an alkyl carboxylate, an ⁇ -olefin sulfonate, a polyoxyethylene alkyl ether acetate, an N-acyl amino acid and a salt thereof, an N-acylmethyl taurine salt, and an alkyl.
  • Examples of the cationic surfactant include 2-vinylpyridine derivatives, poly4-vinylpyridine derivatives and the like.
  • amphoteric surfactant examples include lauryldimethylaminoacetic acid betaine, 2-alkyl-N-carboxymethyl-N-hydroxyethylimidazolinium betaine, coconut oil fatty acid amide propyldimethylaminoacetic acid betaine, polyoctylpolyaminoethylglycine, and imidazoline. Examples include derivatives.
  • nonionic surfactant examples include ethers such as polyoxyethylene nonylphenyl ether, polyoxyethylene octylphenyl ether, polyoxyethylene dodecylphenyl ether, polyoxyethylene oleyl ether, polyoxyethylene lauryl ether, and polyoxyethylene alkyl ether.
  • Esters such as polyoxyethylene oleic acid ester, polyoxyethylene distearate, sorbitan laurate, sorbitan monostearate, sorbitan monooleate, sorbitan sesquioleate, polyoxyethylene monooleate, polyoxyethylene stearate, etc.
  • non-ethylene oxide-modified acetylene-based nonionic surfactants such as Surfinol 104 and 105 and ethylene oxide-modified acetylene-based nonionic surfactants such as Surfinol 465 are preferable, and ethylene oxide-modified acetylene-based nonionic compounds such as Surfinol 465 are preferable. It is more preferably a surfactant, and even more preferably Surfinol 465.
  • silicone-based surfactant examples include polyether-modified siloxane, polyether-modified polydimethylsiloxane, and the like.
  • examples of commercially available products include BYK-347 (polyether-modified siloxane); BYK-345, BYK-348 (polyether-modified polydimethylsiloxane), all manufactured by Big Chemie.
  • fluorine-based surfactant examples include a perfluoroalkyl sulfonic acid compound, a perfluoroalkyl carboxylic acid compound, a perfluoroalkyl phosphate ester compound, a perfluoroalkyl ethylene oxide adduct, and a perfluoroalkyl ether group as side chains.
  • fluorine-based surfactant examples include polyoxyalkylene ether polymer compounds having.
  • Examples of commercially available products include Zonyl TBS, FSP, FSA, FSN-100, FSN, FSO-100, FSO, FS-300, Capstone FS-30, FS-31 (all manufactured by DuPont); PF-151N, PF-154N (all manufactured by Omniova Co., Ltd.); and the like.
  • the coloring liquid according to the present embodiment contains a surfactant
  • the content thereof is preferably 0.01 to 10% by mass, preferably 0.03, based on the total amount of the coloring liquid according to the present embodiment. More preferably, it is ⁇ 5% by mass.
  • the coloring liquid according to this embodiment preferably further contains water.
  • water water having few impurities such as ion-exchanged water and distilled water is preferable.
  • the content thereof is preferably 0.1 to 90% by mass, preferably 10 to 80% by mass, based on the total amount of the coloring liquid according to the present embodiment. Is more preferable.
  • the coloring liquid according to this embodiment may contain additives other than the above.
  • Additives include, for example, water-soluble organic solvents, preservatives, pH regulators, chelating reagents, rust inhibitors, water-soluble UV absorbers, water-soluble polymer compounds, viscosity regulators, dye solubilizers, antioxidants, etc. Examples include resin emulsions.
  • the coloring liquid according to the present embodiment preferably contains at least one selected from the group consisting of a water-soluble organic solvent, a preservative, and a pH adjuster.
  • water-soluble organic solvent examples include glycol-based solvents, polyhydric alcohols, pyrrolidones and the like.
  • glycol-based solvent examples include glycerin, polyglycerin (# 310, # 750, # 800), diglycerin, triglycerin, tetraglycerin, pentaglycerin, hexaglycerin, heptaglycerin, octaglycerin, nonaglycerin, decaglycerin, and the like. Examples thereof include undecaglycerin, dodecaglycerin, tridecaglycerin, and tetradecaglycerin.
  • polyhydric alcohols include C2-C6 polyhydric alcohol having 2 to 3 alcoholic hydroxyl groups; di or tri-C2-C3 alkylene glycol; poly-C2-C3 having 4 or more repeating units and a molecular weight of about 20000 or less.
  • alkylene glycol preferably liquid polyalkylene glycol and the like. Specific examples thereof include ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol, polyethylene glycol, polypropylene glycol, 1,3-propanediol, 1,2-butanediol, thiodiglycol, and 1,3-butanediol.
  • pyrrolidones include 2-pyrrolidone, N-methyl-2-pyrrolidone and the like.
  • a compound that dissolves in water and acts as a wetting agent is also included in the water-soluble organic solvent for convenience. Examples of such a compound include urea, ethylene urea, saccharides and the like.
  • the water-soluble organic solvent is preferably a solvent having a low solubility of the colorant, and in particular, a solvent other than glycerin and glycerin (preferably a polyhydric alcohol other than glycerin). ) And is preferable.
  • the coloring liquid according to the present embodiment contains a water-soluble organic solvent
  • the content thereof is preferably 5 to 50% by mass, preferably 10 to 40% by mass, based on the total amount of the coloring liquid according to the present embodiment. % Is more preferable.
  • preservative examples include organic sulfur-based, organic nitrogen-sulfur-based, organic halogen-based, haloallyl sulfone-based, iodopropagil-based, N-haloalkylthio-based, nitrile-based, pyridine-based, 8-oxyquinolin-based, and benzothiazole.
  • Isothiazolin system Dithiol system, Pyridine oxide system, Nitropropane system, Organic tin system, Phenol system, Tetraammonium salt system, Triazine system, Thiadine system, Anilide system, Adamantine system, Dithiocarbamate system, Brominated indanone system, Examples thereof include benzyl bromacetate-based compounds and inorganic salt-based compounds.
  • organic halogen-based compound include sodium pentachlorophenol and the like.
  • Specific examples of the pyridine oxide-based compound include 2-pyridinethiol-1-oxide sodium.
  • isothiazolinone compound examples include 1,2-benzisothiazolin-3-one, 2-n-octyl-4-isothiazolin-3-one, 5-chloro-2-methyl-4-isothiazolin-3-one, and the like.
  • antiseptic and antifungal agents include anhydrous sodium acetate, sodium sorbate, sodium benzoate, trade names Proxel GXL (S) and Proxel XL-2 (S) manufactured by Ronza.
  • any substance can be used as long as the pH of the coloring liquid can be controlled in the range of approximately 5 to 11 without adversely affecting the prepared coloring liquid.
  • alkanolamines such as diethanolamine, triethanolamine and N-methyldiethanolamine
  • alkali metal hydroxides such as lithium hydroxide, sodium hydroxide and potassium hydroxide
  • ammonium hydroxide ammonia water
  • Alkali metal carbonates such as lithium carbonate, sodium carbonate, sodium hydrogencarbonate and potassium carbonate
  • alkali metal salts of organic acids such as potassium acetate
  • inorganic bases such as sodium silicate and disodium phosphate
  • Triethanolamine is preferred.
  • chelating reagent examples include sodium ethylenediamine tetraacetate, sodium nitrilotriacetate, sodium hydroxyethylethylenediamine triacetate, sodium diethylenetriamine pentaacetate, sodium uracil diacetate and the like.
  • rust preventive examples include acidic sulfite, sodium thiosulfate, ammonium thioglucolate, diisopropylammonium nitrate, pentaerythritol tetranitrate, dicyclohexylammonium nitrate and the like.
  • water-soluble ultraviolet absorber examples include sulfonated benzophenone-based compounds, benzotriazol-based compounds, salicylic acid-based compounds, cinnamic acid-based compounds, and triazine-based compounds.
  • water-soluble polymer compound examples include polyvinyl alcohol, cellulose derivatives, polyamines, polyimines and the like.
  • examples of the viscosity modifier include water-soluble polymer compounds in addition to water-soluble organic solvents, and examples thereof include polyvinyl alcohol, cellulose derivatives, polyamines, and polyimines.
  • dye-dissolving agent examples include urea, ⁇ -caprolactam, ethylene carbonate and the like.
  • organic and metal complex-based anti-fading agents can be used as the antioxidant.
  • organic anti-fading agent include hydroquinones, alkoxyphenols, dialkoxyphenols, phenols, anilines, amines, indans, chromans, alkoxyanilines, heterocycles and the like.
  • metal complex-based anti-fading agent include nickel complexes and zinc complexes.
  • the resin emulsion examples include acrylic resin, epoxy resin, urethane resin, polyether resin, polyamide resin, unsaturated polyester resin, phenol resin, silicone resin, fluororesin, and polyvinyl resin (vinyl chloride, vinyl acetate, polyvinyl alcohol, etc.). , Alkido resin, polyester resin, amino material (melanin resin, urea resin, urea resin, melanin formaldehyde resin, etc.) and the like.
  • the resin emulsion may contain two or more kinds of resins. Further, two or more kinds of resins may form a core / shell structure. Among the resin emulsions, urethane resin emulsions are preferable.
  • Urethane resin emulsions can be obtained as commercial products, and most of them are emulsions having a solid content concentration of 30 to 60% by mass.
  • Commercially available urethane resin emulsions include, for example, Permarin UA-150, 200, 310, 368, 3945, U-Coat UX-320 (all manufactured by Sanyo Chemical Industries, Ltd.); Hydran WLS-201, 210, HW-312B Latex. (The above is manufactured by DIC Corporation); Superflex 150, 170, 470 (above, manufactured by Daiichi Kogyo Seiyaku Co., Ltd.); and the like.
  • examples of the polycarbonate-based urethane resin include Permarin UA-310, 3945; U-coat UX-320; and the like.
  • examples of the polyether urethane resin include permarin UA-150 and 200; U-coat UX-340; and the like.
  • the urethane resin in the urethane resin emulsion preferably has an SP value of 8 to 24 (cal / cm 3 ) 1/2 , more preferably 8 to 17 (cal / cm 3 ) 1/2 , and 8 It is more preferably ⁇ 11 (cal / cm 3 ) 1/2 .
  • the SP value of the urethane resin is calculated by the Fedors method. When the urethane resin has an acidic group and the acidic group is neutralized to prepare an emulsion, the SP value of the urethane resin before neutralization is used.
  • the acidic group may be alkaline chloride.
  • a urethane resin having an acidic group is added to water and stirred to prepare an aqueous solution, and an alkaline compound is added thereto to adjust the pH to 6.0 to 12.0 to make the acidic group alkaline chloride. can do.
  • alkaline compound examples include hydroxides of alkali metals such as lithium hydroxide, sodium hydroxide and potassium hydroxide; and water of alkaline earth metals such as beryllium hydroxide, magnesium hydroxide, calcium hydroxide and strontium hydroxide. Oxides; etc.
  • a sand mill (bead mill), a roll mill, a ball mill, a paint shaker, an ultrasonic disperser, a high-pressure emulsifier, or the like is used to stir and mix each component constituting the coloring liquid.
  • Known methods such as The order in which each component is added is not particularly limited. For example, when using a sand mill, first, each component and beads as a dispersion medium are charged into the sand mill.
  • the beads glass beads having a particle diameter of 0.01 to 1 mm, zirconia beads and the like can be used.
  • the amount of beads used is preferably 2 to 6 parts by mass with respect to 1 part by mass of the dispersion target.
  • the sand mill is operated to perform the distributed processing.
  • the dispersion treatment conditions are preferably about 1000 to 2000 rpm for 1 to 20 hours.
  • the colored liquid is obtained by removing the beads by filtration or the like after the dispersion treatment.
  • the coloring liquid may be prepared by mixing two or more kinds of water-insoluble coloring agents together with other components.
  • each water-insoluble colorant may be dispersed to prepare an aqueous dispersion, and the obtained two or more aqueous dispersions may be mixed with other components to prepare a coloring liquid.
  • the prepared coloring liquid may be microfiltered using a membrane filter or the like.
  • a membrane filter or the like it is preferable to perform microfiltration for the purpose of preventing nozzle clogging and the like.
  • the pore size of the filter used for microfiltration is usually 0.1 to 1 ⁇ m, preferably 0.1 to 0.8 ⁇ m.
  • the viscosity of the coloring liquid according to this embodiment at 25 ° C. is preferably about 3 to 20 mPa ⁇ s as measured by an E-type viscometer from the viewpoint of high-speed discharge response. Further, the surface tension of the coloring liquid according to the present embodiment at 25 ° C. is preferably about 20 to 45 mN / m when measured by the plate method. Actually, it is adjusted so as to have an appropriate physical property value in consideration of the ejection amount, the response speed, the ink droplet flight characteristics, etc. of the inkjet printer to be used.
  • the coloring liquid according to this embodiment can be used in various fields and is suitable for water-based writing ink, water-based printing ink, information recording ink, printing and the like. It is particularly preferable to use the coloring liquid according to the present embodiment as an ink for inkjet printing.
  • the coloring liquid according to the present embodiment has excellent storage stability without solid precipitation, physical characteristic change, color change, etc. after long-term storage. Further, the coloring liquid according to the present embodiment has good initial filling property to the inkjet head, and also has good continuous printing stability and intermittent ejection property. In addition, the printed matter printed using the coloring liquid according to the present embodiment is excellent in light resistance, color development, and sharpness, so that a good image and a printed matter can be obtained.
  • the ink set according to the present embodiment contains the ink A containing the water-insoluble colorant A described above, and the following (e) to (g):
  • Ink A contains a phytosterol compound, and C.I. I. Includes Ink B containing Disperse Yellow 54 and phytosterol compounds;
  • Ink C containing the water-insoluble colorant B described above;
  • Ink D containing a water-insoluble colorant G having a maximum absorption wavelength in a wavelength range of 560 nm or more and less than 660 nm (provided that CI Disperse Violet 27 or CI Disperse Violet 28 is contained. Includes); At least one of the conditions is satisfied.
  • ink A will be described first, then conditions (e) to (g) will be described, and then other matters will be described.
  • the ink A contains the above-mentioned water-insoluble colorant A.
  • the content of the water-insoluble colorant A is preferably 0.1 to 40% by mass, more preferably 0.5 to 25% by mass, based on the total amount of the ink A.
  • Ink A may further contain a phytosterol compound, a dispersant, a surfactant, water, and other additives, similarly to the coloring liquid according to the present embodiment described above.
  • the ink A contains the phytosterol compound
  • the ink set according to the present embodiment is C.I. I. It contains ink B containing Disperse Yellow 54 and a phytosterol compound.
  • the phytosterol compound contained in the inks A and B is the same as the phytosterol compound which may be contained in the coloring liquid according to the present embodiment described above, detailed description thereof will be omitted.
  • the content of Disperse Yellow 54 is preferably 0.1 to 40% by mass, more preferably 0.5 to 25% by mass, based on the total amount of ink B.
  • the inks A and B may further contain a dispersant, a surfactant, water, and other additives, as in the coloring liquid according to the present embodiment described above.
  • the inks A and B preferably contain a formalin condensate of aromatic sulfonic acid or a salt thereof, and water.
  • the above condition (f) is that the ink set according to the present embodiment contains the ink C containing the water-insoluble colorant B described above.
  • the inks A and C in the ink set according to the present embodiment, for example, a high-quality green-colored printed matter having high saturation and excellent leveling property can be obtained.
  • the content of the water-insoluble colorant B in the ink C is preferably 0.5 to 25% by mass, more preferably 0.1 to 40% by mass, based on the total amount of the ink C.
  • the inks A and C may further contain a phytosterol compound, a dispersant, a surfactant, water, and other additives, as in the coloring liquid according to the present embodiment described above.
  • the ink set according to the present embodiment contains an ink D containing a water-insoluble colorant G having a maximum absorption wavelength in a wavelength range of 560 nm or more and less than 660 nm (however, CI Disperse Violet 27). Or, excluding those containing CI Disperse Violet 28).
  • the inks A and D in the ink set according to the present embodiment for example, a high-quality printed matter having a wide range of expression of cyan to blue hue can be obtained.
  • the water-insoluble colorant G is not particularly limited, but one having an anthraquinone structure is preferable, and one having a molecular weight in the range of 250 to 340 is more preferable.
  • water-insoluble colorant G examples include, for example, C.I. I. Disperse Blue 19, 26, 27, 54, 55, 56, 64, 72, 73, 81, 77, 128, 148, 149, 153, 158, 165, 165: 1, 165: 2, 183, 197, 224 , 225, 257, 268, 287, 337, 345, 359, 360; C.I. I. Solvent Blue 35, 36, 78, 111, 112; C.I. I. Solvent Violet 13; etc. may be mentioned.
  • C.I. I. Disperse blue 359 a compound represented by the following formula (G1) is preferable.
  • the compound represented by the following formula (G1) is C.I. I. Disperse Blue 72, C.I. I. Also called Solvent Violet 13 etc.
  • b * represented by the CIE color space is in the range of ⁇ 70 to ⁇ 40 and a * is in the range of ⁇ 20 to 40 when the absorbance at the maximum absorption wavelength is 1.
  • the one inside is preferable.
  • the content of the water-insoluble colorant G in the ink D is preferably 0.1 to 40% by mass, more preferably 0.5 to 25% by mass, based on the total amount of the ink D.
  • the ink set according to the present embodiment may further contain inks other than the above.
  • inks include yellow ink, magenta ink, cyan ink, black ink, orange ink, violet ink, green ink, turquoise ink, blue ink and the like.
  • light yellow ink, light magenta ink, light cyan ink, light black ink and the like in which the total concentration of the colorant in the ink is changed can also be mentioned.
  • Examples of the colorant contained in other inks include water-insoluble colorants such as disperse dyes and oil-soluble dyes.
  • disperse dye examples include, for example, C.I. I. Disperse Yellow 3, 4, 5, 7, 9, 13, 24, 30, 33, 34, 42, 44, 49, 50, 51, 54, 56, 58, 60, 63, 64, 66, 68, 71 , 74, 76, 79, 82, 83, 85, 86, 88, 90, 91, 93, 98, 99, 100, 104, 114, 116, 118, 119, 122, 124, 126, 135, 140, 141.
  • C.I. Disperse Orange 1, 3, 5, 7, 11, 13, 17, 20, 21, 25, 26, 29, 30, 31, 32, 33, 37, 38, 42, 43, 44, 45, 47, 48 , 50, 53, 54, 55, 56, 57, 58, 59, 61, 66, 76, 78, 80, 89, 90, 91, 93, 96, 97, 119, 127, 130, 139, 142, etc.; C. I.
  • oil-soluble dyes include, for example, C.I. I. Solvent Yellow 2, 6, 14, 16, 21, 25, 29, 30, 33, 51, 56, 77, 80, 82, 88, 89, 93, 116, 150, 160: 1, 163, 179, etc .; C .. I. Solvent orange 1, 2, 14, 45, 60, etc .; C.I. I. Solvent Red 1, 3, 7, 8, 9, 18, 19, 23, 24, 25, 27, 49, 100, 109, 121, 122, 125, 127, 130, 132, 135, 218, 225, 230, etc. C. I. Solvent Violet 13, 31, etc .; C.I. I. Solvent green 3rd grade; C.I. I. Solvent brown 3, 5 mag; C.I. I.
  • Solvent Blue 2 11, 14, 24, 25, 35, 36, 38, 48, 55, 59, 63, 67, 68, 70, 73, 83, 105, 111, 132, etc .; I. Solvent black 3, 5, 7, 23, 27, 28, 29, 34, etc .; and the like.
  • the recording medium according to the present embodiment is the one to which the coloring liquid according to the above-mentioned embodiment or the inks contained in the ink set according to the above-mentioned embodiment are attached.
  • the recording medium is not particularly limited as long as it can be recorded with a coloring liquid or ink, and examples thereof include fibers and paper (plain paper, inkjet paper, etc.).
  • the recording medium according to the present embodiment is preferably hydrophobic fibers.
  • hydrophobic fiber examples include polyester fiber, nylon fiber, triacetate fiber, diacetate fiber, polyamide fiber, and blended fiber using two or more of these fibers. Further, a blended fiber of these hydrophobic fibers and a regenerated fiber such as rayon or a natural fiber such as cotton, silk and wool is also included in the hydrophobic fiber in the present specification. Some of these fibers are known to have an ink receiving layer (bleeding prevention layer), and such fibers are also included in the hydrophobic fibers.
  • the method for forming the ink receiving layer is a known technique, and fibers having an ink receiving layer are also available as commercial products.
  • the material, structure, and the like of the ink receiving layer are not particularly limited, and can be appropriately used depending on the purpose and the like.
  • the method for printing hydrophobic fibers according to the present embodiment is a method for printing hydrophobic fibers using the above-mentioned coloring liquid according to the present embodiment or each ink contained in the above-mentioned ink set according to the present embodiment. ..
  • the printing method of hydrophobic fibers is roughly classified into a direct printing method and a sublimation transfer method.
  • a droplet of a coloring liquid or ink is attached to a hydrophobic fiber by an inkjet printer to obtain a recorded image of characters, patterns, etc., and the ink droplet is attached to the hydrophobic fiber in the printing step. It includes a fixing step of fixing the dye in the coloring liquid or the ink to the hydrophobic fiber by heat, and a cleaning step of cleaning the unfixed dye remaining in the hydrophobic fiber.
  • the fixing step is generally performed by known steaming or baking.
  • the steaming includes, for example, treating the hydrophobic fibers with a high-temperature steamer at 170 to 180 ° C. for about 10 minutes, or using a high-pressure steamer at 120 to 130 ° C. for about 20 minutes, respectively, to change the dye into hydrophobic fibers.
  • There is a method of dyeing also called moist heat fixation.
  • As baking (thermosol) for example, a method of dyeing a dye on hydrophobic fibers (also called dry heat sterilization) by treating the hydrophobic fibers at 190 to 210 ° C. for about 6 to 120 seconds is used. Can be mentioned.
  • the washing step is a step of washing the obtained fibers with warm water and, if necessary, water.
  • the warm water or water used for washing may contain a surfactant. It is also preferable to dry the washed hydrophobic fibers at 50 to 120 ° C. for 5 to 30 minutes.
  • a printing step of obtaining a recorded image of characters, patterns, etc. by adhering droplets of a coloring liquid or ink to an intermediate recording medium by an inkjet printer, and a coloring liquid or ink in the intermediate recording medium includes a transfer step of transferring a recorded image to the hydrophobic fiber by bringing the hydrophobic fiber into contact with the adhesion surface and heat-treating it.
  • the intermediate recording medium is preferably one in which the adhered coloring liquid or the dye in the ink does not aggregate on the surface thereof and does not interfere with the sublimation of the dye when the recorded image is transferred to the hydrophobic fiber.
  • An example of such an intermediate recording medium is a paper having an ink receiving layer formed on the surface of inorganic fine particles such as silica, and a special paper for inkjet can be used.
  • Examples of the heat treatment in the transfer step include dry heat treatment at about 190 to 200 ° C.
  • the method for printing hydrophobic fibers according to the present embodiment may further include a pretreatment step for hydrophobic fibers for the purpose of preventing bleeding and the like.
  • this pretreatment step include a step of applying an aqueous solution (pretreatment liquid) containing a glue material, an alkaline substance, an antioxidant, and a hydrotropy agent to the hydrophobic fiber before adhering the coloring liquid or ink. Be done.
  • the adhesive examples include natural gums such as guar and locust beans; starches; seaweeds such as sodium alginate and furinate; plant skins such as pectic acid; methyl fiber, ethyl fiber, hydroxyethyl cellulose and carboxymethyl cellulose. And the like; processed starch such as carboxymethyl starch; synthetic glue such as polyvinyl alcohol and polyacrylic acid ester; and the like, and sodium alginate is preferable.
  • alkaline substance examples include alkali metal salts of inorganic acids or organic acids; salts of alkaline earth metals; compounds that liberate alkali when heated; and the like, and alkali metal hydroxides and alkali metal salts are preferable. .. Specific examples include, for example, alkali metal hydroxides such as sodium hydroxide and calcium hydroxide; inorganic substances such as sodium carbonate, sodium hydrogencarbonate, potassium carbonate, sodium dihydrogen phosphate, disodium hydrogenphosphate, and sodium phosphate. Examples thereof include alkali metal salts of compounds; alkali metal salts of organic compounds such as sodium formate and sodium trichloroacetate; and sodium hydrogencarbonate is preferable.
  • sodium metanitrobenzene sulfonate is preferable.
  • hydrotropy agent examples include ureas such as urea and dimethylurea, and urea is preferable.
  • the mixing ratio of each component in the pretreatment liquid is, for example, 0.5 to 5% by mass of glutinous agent, 0.5 to 5% by mass of sodium hydrogen carbonate, 0 to 5% by mass of sodium metanitrobenzene sulfonate, and urea. Is 1 to 20% by mass, and the balance is water.
  • the padding ratio is preferably about 40 to 90%, more preferably about 60 to 80%.
  • parts means parts by mass and “%” means parts by mass.
  • the inks in each embodiment are included in the coloring liquid.
  • Table 1 shows the results of measuring the solutions of the water-insoluble colorants used in Examples and Comparative Examples, which were dissolved or dispersed in DMF and adjusted in concentration so that the absorbance at the maximum absorption wavelength in ultraviolet-visible spectroscopic absorption was 1.
  • the compounds represented by the formulas (A1-1) to (A1-3), (B1-1), (F1), and (G1) are JP-A-2018-178038 and JP-A No. 40-4222.
  • Ayyangar N. et al. R. Et al. Ayyangar N.R. et al., Days and Pigments, 991, 16 (3), 197-204
  • Joncryl 678 manufactured by BASF (20 parts) was added to a mixture of 25% sodium hydroxide (6 parts), ion-exchanged water (54 parts), and propylene glycol (20 parts), and the temperature was raised to 90 to 120 ° C. Then, the mixture was stirred for 5 hours to obtain an emulsion solution of Joncryl 678.
  • ⁇ Preparation Example 1a Preparation of Aqueous Dispersion Liquid 1a> C.
  • Disperse Blue 60 4.4 parts
  • compound represented by the formula (B1-1) 5.6 parts
  • Laberin W-40 Aqueous solution of sodium sulphonic acid formalinated polycondensate in creosote, Daiichi Kogyo Seiyaku Co., Ltd.
  • NIKKOL BPS-30 15 parts
  • Surfinol 104PG50 Surfinol 104 (acetylene glycol surfactant, manufactured by Air Products Japan Co., Ltd.) diluted to 50% concentration with propylene glycol.
  • 0.2 mm diameter glass beads were added to the mixture consisting of (0.2 parts), Proxel GXL (S) (manufactured by Ronza) (0.1 parts), and ion-exchanged water (73.9 parts).
  • the dispersion treatment was carried out for about 15 hours under cooling with a sand mill.
  • the obtained liquid was filtered through a glass fiber filter paper GC-50 (manufactured by ADVANTEC, filter pore size: 0.5 ⁇ m) to obtain an aqueous dispersion liquid 1a.
  • Preparation Example 2a Preparation of Aqueous Dispersion Liquid 2a> Same as Preparation Example 1a except that the colorant is changed to the compound represented by the formula (A1-1) (5.3 parts) and the compound represented by the formula (B1-1) (4.7 parts). To obtain an aqueous dispersion 2a.
  • ⁇ Preparation Example 3a Preparation of Aqueous Dispersion Liquid 3a> The compound represented by the formula (A1-1) (5.3 parts), the compound represented by the formula (B1-1) (4.7 parts), SM-57 (polyoxyethylene styrylphenyl ether sulfate-based dispersant).
  • Preparation Example 4a Preparation of Aqueous Dispersion Liquid 4a> Same as Preparation Example 1a except that the colorant is changed to the compound represented by the formula (A1-2) (5.6 parts) and the compound represented by the formula (B1-1) (4.4 parts). To obtain an aqueous dispersion 4a.
  • Preparation Example 5a Preparation of Aqueous Dispersion Liquid 5a> Same as Preparation Example 3a except that the colorant is changed to the compound represented by the formula (A1-2) (5.6 parts) and the compound represented by the formula (B1-1) (4.4 parts). To obtain an aqueous dispersion 5a.
  • ⁇ Preparation Example 6a Preparation of Aqueous Dispersion Liquid 6a> The compound represented by the formula (A1-2) (5.6 parts), the compound represented by the formula (B1-1) (4.4 parts), the emulsion solution of Joncryl 678 (30 parts), and the surfactant 104PG50. (Surfinol 104 (acetylene glycol surfactant, manufactured by Air Products Japan Co., Ltd.) diluted to a concentration of 50% with propylene glycol) (0.2 part), Proxel GXL (S) (manufactured by Ronza Co., Ltd.) (0.
  • 0.2 mm diameter glass beads were added to a mixture consisting of 1 part) and ion-exchanged water (59.7 parts), and the mixture was dispersed under cooling with a sand mill for about 15 hours.
  • the obtained liquid was filtered through a glass fiber filter paper GC-50 (manufactured by ADVANTEC, filter pore size: 0.5 ⁇ m) to obtain an aqueous dispersion liquid 6a.
  • ⁇ Preparation Example 8a Preparation of Aqueous Dispersion Liquid 8a> Coloring agent C.I. I.
  • An aqueous dispersion 8a was obtained in the same manner as in Preparation Example 1a except that the mixture was changed to Disperse Blue 359 (6.0 parts) and the compound represented by the formula (B1-1) (4.0 parts). ..
  • ⁇ Preparation Example 9a Preparation of Aqueous Dispersion Liquid 9a> Coloring agent C.I. I.
  • An aqueous dispersion 9a was obtained in the same manner as in Preparation Example 3a except that the mixture was changed to Disperse Blue 359 (6.0 parts) and the compound represented by the formula (B1-1) (4.0 parts). ..
  • ⁇ Preparation Example 10a Preparation of Aqueous Dispersion Liquid 10a> Coloring agent C.I. I.
  • An aqueous dispersion 10a was obtained in the same manner as in Preparation Example 6a except that the mixture was changed to Disperse Blue 359 (6.0 parts) and the compound represented by the formula (B1-1) (4.0 parts). ..
  • ⁇ Preparation Example 11a Preparation of Aqueous Dispersion Liquid 11a> Coloring agent C.I. I.
  • An aqueous dispersion 11a was obtained in the same manner as in Preparation Example 1a except that the mixture was changed to Disperse Blue 72 (4.7 parts) and the compound represented by the formula (B1-1) (5.3 parts). ..
  • Examples 1a to 7a and Comparative Examples 1a to 4a Preparation of ink>
  • the aqueous dispersions 1a to 11a obtained above were mixed with each component shown in Tables 2 and 3 below, and after stirring for 30 minutes, the glass fiber filter paper GC-50 (manufactured by ADVANTEC, filter pore diameter: 0.
  • Each ink of Examples 1a to 7a and Comparative Examples 1a to 4a was prepared by filtering with 5 ⁇ m).
  • the numerical value of each component indicates the number of copies added.
  • ⁇ Preparation Example 1b Preparation of aqueous dispersion 1b> C.
  • Disperse Blue 60 3.3 parts
  • Kayaset Yellow AG manufactured by Nippon Kayaku Co., Ltd.
  • CI Disperse Yellow 54 (6.7 parts)
  • Labelin W-40 Cyleosort Oil Soda Sulfate
  • Formalin polycondensate aqueous solution manufactured by Daiichi Kogyo Seiyaku Co., Ltd.
  • ⁇ Preparation Example 2b Preparation of Aqueous Dispersion Liquid 2b> Colorants were added to the compound represented by the formula (A1-1) (4.2 parts) and Kayaset Yellow AG (manufactured by Nippon Kayaku Co., Ltd., CI Disperse Yellow 54) (5.8 parts). An aqueous dispersion 1b was obtained in the same manner as in Preparation Example 1b except that it was changed.
  • ⁇ Preparation Example 3b Preparation of Aqueous Dispersion Liquid 3b> Compound represented by the formula (A1-1) (4.2 parts), Kayaset Yellow AG (manufactured by Nippon Kayaku Co., Ltd., CI Disperse Yellow 54) (5.8 parts), SM-57 ( Polyoxyethylene styrylphenyl ether sulfate-based dispersant manufactured by Toho Chemical Industry Co., Ltd.
  • ⁇ Preparation Example 4b Preparation of Aqueous Dispersion Liquid 4b> Colorants were added to the compound represented by the formula (A1-2) (4.2 parts) and Kayaset Yellow AG (manufactured by Nippon Kayaku Co., Ltd., CI Disperse Yellow 54) (5.8 parts). An aqueous dispersion 4b was obtained in the same manner as in Preparation Example 1b except that it was changed.
  • ⁇ Preparation Example 5b Preparation of Aqueous Dispersion Liquid 5b> Colorants were added to the compound represented by the formula (A1-2) (4.2 parts) and Kayaset Yellow AG (manufactured by Nippon Kayaku Co., Ltd., CI Disperse Yellow 54) (5.8 parts). An aqueous dispersion 5b was obtained in the same manner as in Preparation Example 3b except for the modification.
  • ⁇ Preparation Example 6b Preparation of Aqueous Dispersion Liquid 6b> The compound represented by the formula (A1-2) (4.2 parts), Kayaset Yellow AG (manufactured by Nippon Kayaku Co., Ltd., CI Disperse Yellow 54) (5.8 parts), Joncryl 678 above.
  • Emulsion solution (30 parts), Surfinol 104PG50 (Surfinol 104 (acetylene glycol surfactant, manufactured by Air Products Japan Co., Ltd.) diluted to 50% concentration with propylene glycol) (0.2 parts), Proxel GXL ( S) 0.2 mm diameter glass beads were added to a mixture consisting of (0.1 part) (manufactured by Ronza) and ion-exchanged water (59.7 parts), and the mixture was dispersed for about 15 hours under cooling with a sand mill. rice field. The obtained liquid was filtered through a glass fiber filter paper GC-50 (manufactured by ADVANTEC, filter pore size: 0.5 ⁇ m) to obtain an aqueous dispersion liquid 6b.
  • GC-50 manufactured by ADVANTEC, filter pore size: 0.5 ⁇ m
  • ⁇ Preparation Example 7b Preparation of Aqueous Dispersion Liquid 7b> Colorants were added to the compound represented by the formula (A1-3) (4.6 parts) and Kayaset Yellow AG (manufactured by Nippon Kayaku Co., Ltd., CI Disperse Yellow 54) (5.4 parts). An aqueous dispersion 7b was obtained in the same manner as in Preparation Example 1b except that it was changed.
  • ⁇ Preparation Example 8b Preparation of Aqueous Dispersion Liquid 8b> Coloring agent C.I. I. Same as Preparation Example 1b except that it is changed to Disperse Blue 359 (5.0 copies) and Kayaset Yellow AG (C.I. Disperse Yellow 54) (5.0 copies) manufactured by Nippon Kayaku Co., Ltd. To obtain an aqueous dispersion 8b.
  • ⁇ Preparation Example 9b Preparation of Aqueous Dispersion Liquid 9b> Coloring agent C.I. I. Same as Preparation Example 3b except that it is changed to Disperse Blue 359 (5.0 copies) and Kayaset Yellow AG (C.I. Disperse Yellow 54) (5.0 copies) manufactured by Nippon Kayaku Co., Ltd. To obtain an aqueous dispersion 9b.
  • ⁇ Preparation Example 10b Preparation of Aqueous Dispersion Liquid 10b> Coloring agent C.I. I. Same as Preparation Example 6b except that it is changed to Disperse Blue 359 (5.0 copies) and Kayaset Yellow AG (C.I. Disperse Yellow 54) (5.0 copies) manufactured by Nippon Kayaku Co., Ltd. To obtain an aqueous dispersion 10b.
  • ⁇ Preparation Example 11b Preparation of Aqueous Dispersion Liquid 11b> Coloring agent C.I. I. Same as Preparation Example 1b except that it is changed to Disperse Blue 72 (5.3 parts) and Kayaset Yellow AG (CI Disperse Yellow 54) (4.7 parts) manufactured by Nippon Kayaku Co., Ltd. To obtain an aqueous dispersion 11b.
  • Examples 1b to 7b and Comparative Examples 1b to 4b Preparation of ink>
  • the aqueous dispersions 1b to 11b obtained above were mixed with each component shown in Tables 5 and 6 below, and after stirring for 30 minutes, the glass fiber filter paper GC-50 (manufactured by ADVANTEC, filter pore diameter: 0.
  • Each ink of Examples 1b to 7b and Comparative Examples 1b to 4b was prepared by filtering with 5 ⁇ m).
  • the numerical value of each component indicates the number of copies added.
  • ⁇ Preparation Example 1c Preparation of Aqueous Dispersion Liquid 1c> Kayaset Yellow AG (manufactured by Nippon Kayaku Co., Ltd., CI Disperse Yellow 54) (10 parts), Laberin W-40 (Aqueous solution of sodium sulphonate polycondensate in creoseto oil, manufactured by Daiichi Kogyo Seiyaku Co., Ltd.) (15 parts), NIKKOL BPS-30 (0.8 parts), Surfinol 104PG50 (Surfinol 104 (acetylene glycol surfactant, manufactured by Air Products Japan Co., Ltd.) diluted to 50% concentration with propylene glycol) Add 0.2 mm diameter glass beads to a mixture consisting of (0.2 part), Proxel GXL (S) (manufactured by Ronza) (0.1 part), and ion-exchanged water (73.9 parts), and use a sand mill.
  • Kayaset Yellow AG manufactured by Nippon Kayaku Co., Ltd
  • the dispersion treatment was carried out for about 15 hours under cooling.
  • the obtained liquid was filtered through a glass fiber filter paper GC-50 (manufactured by ADVANTEC, filter pore size: 0.5 ⁇ m) to obtain an aqueous dispersion liquid 1c.
  • ⁇ Preparation Example 2c Preparation of Aqueous Dispersion Liquid 2c> Coloring agent C.I. I. An aqueous dispersion 2c was obtained in the same manner as in Preparation Example 1c except that it was changed to Disperse Brown 27.
  • ⁇ Preparation Example 3c Preparation of Aqueous Dispersion Liquid 3c> An aqueous dispersion 3c was obtained in the same manner as in Preparation Example 1c except that the colorant was changed to the compound represented by the formula (A1-1).
  • ⁇ Preparation Example 4c Preparation of Aqueous Dispersion Liquid 4c> Coloring agent C.I. I. An aqueous dispersion 4c was obtained in the same manner as in Preparation Example 1c except that the mixture was changed to Disperse Blue 60.
  • ⁇ Preparation Example 5c Preparation of Aqueous Dispersion Liquid 5c> An aqueous dispersion 5c was obtained in the same manner as in Preparation Example 1c except that the colorant was changed to the compound represented by the formula (A1-2).
  • ⁇ Preparation Example 6c Preparation of Aqueous Dispersion Liquid 6c> Coloring agent C.I. I. An aqueous dispersion 6c was obtained in the same manner as in Preparation Example 1c except that the mixture was changed to Disperse Blue 359.
  • ⁇ Preparation Example 8c Preparation of Aqueous Dispersion Liquid 8c> Kayaset Yellow AG (manufactured by Nippon Kayaku Co., Ltd., CI Disperse Yellow 54) (10 parts), Joncryl 678 emulsion (30 parts), Surfinol 104PG50 (Surfinol 104 (acetylene glycol surfactant)) , Air Products Japan Co., Ltd.) diluted to 50% concentration with propylene glycol) (0.2 parts), Proxel GXL (S) (manufactured by Ronza Co., Ltd.) (0.1 parts), and ion-exchanged water (59 parts).
  • Kayaset Yellow AG manufactured by Nippon Kayaku Co., Ltd., CI Disperse Yellow 54
  • Joncryl 678 emulsion 30 parts
  • Surfinol 104PG50 Surfinol 104 (acetylene glycol surfactant)
  • Air Products Japan Co., Ltd. diluted to 50% concentration with propy
  • 0.2 mm diameter glass beads were added to the mixture consisting of (7 parts), and the mixture was subjected to dispersion treatment for about 15 hours under cooling with a sand mill.
  • the obtained liquid was filtered through a glass fiber filter paper GC-50 (manufactured by ADVANTEC, filter pore size: 0.5 ⁇ m) to obtain an aqueous dispersion liquid 8c.
  • ⁇ Preparation Example 9c Preparation of Aqueous Dispersion Liquid 9c> Coloring agent C.I. I.
  • An aqueous dispersion 9c was obtained in the same manner as in Preparation Example 8c except that it was changed to Disperse Brown 27.
  • ⁇ Preparation Example 10c Preparation of Aqueous Dispersion Liquid 10c> An aqueous dispersion 10c was obtained in the same manner as in Preparation Example 8c except that the colorant was changed to the compound represented by the formula (A1-1).
  • ⁇ Preparation Example 11c Preparation of Aqueous Dispersion Liquid 11c> Coloring agent C.I. I. An aqueous dispersion 11c was obtained in the same manner as in Preparation Example 8c except that the mixture was changed to Disperse Blue 360.
  • ⁇ Preparation Example 12c Preparation of Aqueous Dispersion Liquid 12c> Kayaset Yellow AG (manufactured by Nippon Kayaku Co., Ltd., CI Disperse Yellow 54) (10 parts), SM-57 (manufactured by Toho Chemical Industry Co., Ltd., polyoxyethylene styrylphenyl ether sulfate-based dispersant) (10) Part), Surfinol 104PG50 (Surfinol 104 (acetylene glycol surfactant, manufactured by Air Products Japan Co., Ltd.) diluted to 50% concentration with propylene glycol) (0.2 part), Proxel GXL (S) (Lonza) 0.2 mm diameter glass beads were added to a mixture consisting of (0.1 part) and ion-exchanged water (79.7 parts), and the dispersion treatment was carried out for about 15 hours under cooling with a sand mill. The obtained liquid was filtered through a glass fiber filter paper GC-50 (man
  • ⁇ Preparation Example 14c Preparation of Aqueous Dispersion Solution 14c> An aqueous dispersion 14c was obtained in the same manner as in Preparation Example 12c except that the colorant was changed to the compound represented by the formula (A1-1).
  • ⁇ Preparation Example 15c Preparation of Aqueous Dispersion Liquid 15c> Coloring agent C.I. I. An aqueous dispersion 15c was obtained in the same manner as in Preparation Example 12c except that the mixture was changed to Disperse Blue 360.
  • Examples 1c to 14c and Comparative Example 1c Ink preparation> After mixing the aqueous dispersions 1c to 15c obtained above with each component shown in Tables 8 and 9 below and stirring for 30 minutes, the glass fiber filter paper GC-50 (manufactured by ADVANTEC, filter pore diameter: 0. Each ink of Examples 1c to 14c and Comparative Example 1c was prepared by filtering with 5 ⁇ m). In the table, the numerical value of each component indicates the number of copies added.
  • Each of the prepared inks is filled in an inkjet printer (manufactured by EPSON Co., Ltd., trade name PX-504A), and using TRANSJET EcoII 8385 (95 g / m 2 ) as an intermediate recording medium, 100% Duty and 40% Duty single colors. Intermediate recording media on which solid images were printed were obtained. After superimposing the ink-adhered surface of each of the obtained intermediate recording media and the polyester cloth (Teijin Tropical), a desktop automatic flat press machine (AF-65TEN manufactured by Asahi Textile Machinery Co., Ltd.) was used at 200 ° C. for 30 seconds. By heat treatment under the above conditions, the dyed products dyed by the sublimation transfer method were obtained. The following evaluations were performed on each of the obtained dyed products (for the inks of Examples 10c to 14c, only the evaluation of color development was performed). The evaluation results are shown in Tables 10 and 11.
  • Sigma K / S value is 360 or more A: Sigma K / S value is 350 or more and less than 360 B: Sigma K / S value is 340 or more and less than 350 C: Sigma K / S value is 330 or more and less than 340 D: Sigma K / S value is less than 330
  • L * D65 is the L * value in the D65 light source
  • L * A is the L * value in the A light source
  • a * D65 is the a * value in the D65 light source
  • a * A is the a * value in the A light source
  • b * D65 Indicates the b * value in the D65 light source
  • b * A indicates the b * value in the A light source.
  • ⁇ E D65-A [(L * D65 -L * A ) 2 + (a * D65 -a * A ) 2 + (b * D65 -b * A ) 2 ] 0.5 ... (I)
  • the color rendering property was evaluated from the value of ⁇ ED65-A according to the following evaluation criteria.
  • the inks of Examples 1c to 14c were superior in color development to the inks of Comparative Example 1c. Further, the inks of Examples 1c to 9c were also excellent in the performance of suppressing the hue change due to the influence of the color rendering property as compared with the inks of Comparative Example 1c.
  • ⁇ Preparation Example 1d Preparation of aqueous dispersion 1d> Kayaset Yellow AG (manufactured by Nippon Kayaku Co., Ltd., CI Disperse Yellow 54) (10 parts), Laberin W-40 (Aqueous solution of sodium sulphonate polycondensate in creoseto oil, manufactured by Daiichi Kogyo Seiyaku Co., Ltd.) (15 parts), NIKKOL BPS-30 (0.8 parts), Surfinol 104PG50 (Surfinol 104 (acetylene glycol surfactant, manufactured by Air Products Japan Co., Ltd.) diluted to 50% concentration with propylene glycol) Add 0.2 mm diameter glass beads to a mixture consisting of (0.2 part), Proxel GXL (S) (manufactured by Ronza) (0.1 part), and ion-exchanged water (73.9 parts), and use a sand mill.
  • Kayaset Yellow AG manufactured by Nippon Kayaku Co., Ltd.,
  • the dispersion treatment was carried out for about 15 hours under cooling.
  • the obtained liquid was filtered through a glass fiber filter paper GC-50 (manufactured by ADVANTEC, filter pore size: 0.5 ⁇ m) to obtain an aqueous dispersion liquid 1d.
  • ⁇ Preparation Example 2d Preparation of aqueous dispersion 2d> Coloring agent C.I. I. An aqueous dispersion 2d was obtained in the same manner as in Preparation Example 1d except that the mixture was changed to Disperse Brown 27.
  • ⁇ Preparation Example 3d Preparation of Aqueous Dispersion Liquid 3d> An aqueous dispersion 3d was obtained in the same manner as in Preparation Example 1d except that the colorant was changed to the compound represented by the formula (A1-1).
  • ⁇ Preparation Example 4d Preparation of aqueous dispersion 4d> Coloring agent C.I. I. An aqueous dispersion 4d was obtained in the same manner as in Preparation Example 1d except that the mixture was changed to Disperse Blue 60.
  • ⁇ Preparation Example 5d Preparation of Aqueous Dispersion Liquid 5d> An aqueous dispersion 5d was obtained in the same manner as in Preparation Example 1d except that the colorant was changed to the compound represented by the formula (A1-2).
  • ⁇ Preparation Example 6d Preparation of aqueous dispersion 6d> Coloring agent C.I. I. An aqueous dispersion 6d was obtained in the same manner as in Preparation Example 1d except that the mixture was changed to Disperse Blue 359.
  • ⁇ Preparation Example 7d Preparation of aqueous dispersion 7d> Coloring agent C.I. I. An aqueous dispersion 7d was obtained in the same manner as in Preparation Example 1d except that the mixture was changed to Disperse Blue 360.
  • ⁇ Preparation Example 8d Preparation of aqueous dispersion 8d> Kayaset Yellow AG (manufactured by Nippon Kayaku Co., Ltd., CI Disperse Yellow 54) (10 parts), Joncryl 678 emulsion (30 parts), Surfinol 104PG50 (Surfinol 104 (acetylene glycol surfactant)) , Air Products Japan Co., Ltd.) diluted to 50% concentration with propylene glycol) (0.2 parts), Proxel GXL (S) (manufactured by Ronza Co., Ltd.) (0.1 parts), and ion-exchanged water (59 parts).
  • Kayaset Yellow AG manufactured by Nippon Kayaku Co., Ltd., CI Disperse Yellow 54
  • Joncryl 678 emulsion 30 parts
  • Surfinol 104PG50 Surfinol 104 (acetylene glycol surfactant)
  • Air Products Japan Co., Ltd. diluted to 50% concentration with propylene glyco
  • 0.2 mm diameter glass beads were added to the mixture consisting of (7 parts), and the mixture was subjected to dispersion treatment for about 15 hours under cooling with a sand mill.
  • the obtained liquid was filtered through a glass fiber filter paper GC-50 (manufactured by ADVANTEC, filter pore size: 0.5 ⁇ m) to obtain an aqueous dispersion liquid 8d.
  • ⁇ Preparation Example 9d Preparation of aqueous dispersion 9d> Coloring agent C.I. I.
  • An aqueous dispersion 9d was obtained in the same manner as in Preparation Example 8d except that it was changed to Disperse Brown 27.
  • ⁇ Preparation Example 10d Preparation of Aqueous Dispersion Liquid 10d> An aqueous dispersion 10d was obtained in the same manner as in Preparation Example 8d except that the colorant was changed to the compound represented by the formula (A1-1).
  • ⁇ Preparation Example 11d Preparation of Aqueous Dispersion Liquid 11d> Coloring agent C.I. I. An aqueous dispersion 11d was obtained in the same manner as in Preparation Example 8d except that the mixture was changed to Disperse Blue 359.
  • ⁇ Preparation Example 12d Preparation of Aqueous Dispersion Liquid 12d> Coloring agent C.I. I. An aqueous dispersion 12d was obtained in the same manner as in Preparation Example 8d except that the mixture was changed to Disperse Blue 360.
  • ⁇ Preparation Example 13d Preparation of Aqueous Dispersion Liquid 13d> Kayaset Yellow AG (manufactured by Nippon Kayaku Co., Ltd., CI Disperse Yellow 54) (10 parts), SM-57 (manufactured by Toho Chemical Industry Co., Ltd., polyoxyethylene styrylphenyl ether sulfate-based dispersant) (10) Part), Surfinol 104PG50 (Surfinol 104 (acetylene glycol surfactant, manufactured by Air Products Japan Co., Ltd.) diluted to 50% concentration with propylene glycol) (0.2 part), Proxel GXL (S) (Lonza) 0.2 mm diameter glass beads were added to a mixture consisting of (0.1 part) and ion-exchanged water (79.7 parts), and the dispersion treatment was carried out for about 15 hours under cooling with a sand mill. The obtained liquid was filtered through a glass fiber filter paper GC-50 (man
  • ⁇ Preparation Example 14d Preparation of Aqueous Dispersion Liquid 14d> Coloring agent C.I. I. An aqueous dispersion 14d was obtained in the same manner as in Preparation Example 13d except that it was changed to Disperse Brown 27.
  • ⁇ Preparation Example 15d Preparation of Aqueous Dispersion Liquid 15d> An aqueous dispersion 15d was obtained in the same manner as in Preparation Example 13d except that the colorant was changed to the compound represented by the formula (A1-1).
  • ⁇ Preparation Example 16d Preparation of Aqueous Dispersion Liquid 16d> Coloring agent C.I. I. An aqueous dispersion 16d was obtained in the same manner as in Preparation Example 13d except that the mixture was changed to Disperse Blue 359.
  • ⁇ Preparation Example 17d Preparation of Aqueous Dispersion Liquid 17d> Coloring agent C.I. I. An aqueous dispersion 17d was obtained in the same manner as in Preparation Example 13d except that the mixture was changed to Disperse Blue 360.
  • Examples 1d to 10d and Comparative Example 1d Preparation of ink> After mixing the aqueous dispersions 1d to 17d obtained above with each component shown in Table 12 below and stirring for 30 minutes, the glass fiber filter paper GC-50 (manufactured by ADVANTEC, filter pore size: 0.5 ⁇ m). Each ink of Examples 1d to 10d and Comparative Example 1d was prepared by filtering with. In the table, the numerical value of each component indicates the number of copies added.
  • Sigma K / S value is 350 or more
  • B Sigma K / S value is 340 or more and less than 350
  • C Sigma K / S value is 330 or more and less than 340
  • D Sigma K / S value is less than 330
  • L * D65 is the L * value in the D65 light source
  • L * A is the L * value in the A light source
  • a * D65 is the a * value in the D65 light source
  • a * A is the a * value in the A light source
  • b * D65 Indicates the b * value in the D65 light source
  • b * A indicates the b * value in the A light source.
  • ⁇ E D65-A [(L * D65 -L * A ) 2 + (a * D65 -a * A ) 2 + (b * D65 -b * A ) 2 ] 0.5 ... (I)
  • the color rendering property was evaluated from the value of ⁇ ED65-A according to the following evaluation criteria.
  • ⁇ Preparation Example 2e Preparation of Aqueous Dispersion Liquid 2e> An aqueous dispersion 2e was obtained in the same manner as in Preparation Example 1e except that the colorant was changed to the compound represented by the formula (A1-1).
  • ⁇ Preparation Example 3e Preparation of Aqueous Dispersion Liquid 3e> An aqueous dispersion 3e was obtained in the same manner as in Preparation Example 1e except that the colorant was changed to the compound represented by the formula (A1-2).
  • ⁇ Preparation Example 4e Preparation of Aqueous Dispersion Liquid 4e> An aqueous dispersion 4e was obtained in the same manner as in Preparation Example 1e except that the colorant was changed to the compound represented by the formula (A1-3).
  • ⁇ Preparation Example 5e Preparation of Aqueous Dispersion Liquid 5e> An aqueous dispersion 5e was obtained in the same manner as in Preparation Example 1e except that the colorant was changed to the compound represented by the formula (F1).
  • ⁇ Preparation Example 6e Preparation of Aqueous Dispersion Liquid 6e> Coloring agent C.I. I. An aqueous dispersion 6e was obtained in the same manner as in Preparation Example 1e except that the mixture was changed to Disperse Blue 359.
  • ⁇ Preparation Example 7e Preparation of Aqueous Dispersion Liquid 7e> C.
  • Disperse Blue 60 (10 parts), Laberin W-40 (Aqueous solution of sodium sulfonate formalin polycondensate of cleosort oil, manufactured by Daiichi Kogyo Seiyaku Co., Ltd.) (15 parts), Surfinol 104PG50 (Surfinol 104 (acetylene glycol surfactant)) Activator, manufactured by Air Products Japan Co., Ltd. diluted to a concentration of 50% with propylene glycol) (0.2 parts), Proxel GXL (S) (manufactured by Ronza Co., Ltd.) (0.1 parts), and ion-exchanged water.
  • Laberin W-40 Aqueous solution of sodium sulfonate formalin polycondensate of cleosort oil, manufactured by Daiichi Kogyo Seiyaku Co., Ltd.
  • Surfinol 104PG50 Surf
  • 0.2 mm diameter glass beads were added to the mixture consisting of (74.7 parts), and the mixture was subjected to dispersion treatment under cooling with a sand mill for about 15 hours.
  • the obtained liquid was filtered through a glass fiber filter paper GC-50 (manufactured by ADVANTEC, filter pore size: 0.5 ⁇ m) to obtain an aqueous dispersion 7e.
  • ⁇ Preparation Example 8e Preparation of Aqueous Dispersion Liquid 8e> An aqueous dispersion 8e was obtained in the same manner as in Preparation Example 7e except that the colorant was changed to the compound represented by the formula (A1-1).
  • ⁇ Preparation Example 9e Preparation of Aqueous Dispersion Liquid 9e> An aqueous dispersion 9e was obtained in the same manner as in Preparation Example 7e except that the colorant was changed to the compound represented by the formula (F1).
  • ⁇ Preparation Example 10e Preparation of Aqueous Dispersion Liquid 10e> The compound represented by the formula (A1-1) (10 parts), the emulsion solution of Joncryl 678 (30 parts), NIKKOL BPS-30 (0.8 parts), Surfinol 104PG50 (Surfinol 104 (acetylene glycol surfactant surface activity)). Agent, manufactured by Air Products Japan Co., Ltd. diluted to 50% concentration with propylene glycol) (0.2 parts), Proxel GXL (S) (manufactured by Ronza Co., Ltd.) (0.1 parts), and ion-exchanged water (0.1 parts).
  • A1-1 The compound represented by the formula (A1-1) (10 parts), the emulsion solution of Joncryl 678 (30 parts), NIKKOL BPS-30 (0.8 parts), Surfinol 104PG50 (Surfinol 104 (acetylene glycol surfactant surface activity)). Agent, manufactured by Air Products Japan Co., Ltd.
  • aqueous dispersion liquid 10e 0.2 mm diameter glass beads were added to the mixture consisting of 58.9 parts), and the mixture was dispersed under cooling with a sand mill for about 15 hours.
  • the obtained liquid was filtered through a glass fiber filter paper GC-50 (manufactured by ADVANTEC, filter pore size: 0.5 ⁇ m) to obtain an aqueous dispersion liquid 10e.
  • ⁇ Preparation Example 11e Preparation of Aqueous Dispersion Liquid 11e> An aqueous dispersion 11e was obtained in the same manner as in Preparation Example 10e except that the colorant was changed to the compound represented by the formula (F1).
  • ⁇ Preparation Example 12e Preparation of Aqueous Dispersion Liquid 12e> Compound represented by the formula (A1-1) (10 parts), SM-57 (polyoxyethylene styrylphenyl ether sulfate-based dispersant manufactured by Toho Chemical Industry Co., Ltd.) (10 parts), NIKKOL BPS-30 (0.
  • ⁇ Preparation Example 13e Preparation of Aqueous Dispersion Liquid 13e> An aqueous dispersion 13e was obtained in the same manner as in Preparation Example 12e except that the colorant was changed to the compound represented by the formula (F1).
  • Examples 1e to 22e and Comparative Examples 1e to 3e Preparation of ink>
  • the aqueous dispersions 1e to 13e obtained above were mixed with each component shown in Tables 14 and 15 below, and after stirring for 30 minutes, the glass fiber filter paper GC-50 (manufactured by ADVANTEC, filter pore diameter: 0.
  • Each ink of Examples 1e to 22e and Comparative Examples 1e to 3e was prepared by filtering with 5 ⁇ m).
  • the numerical value of each component indicates the number of copies added.
  • Sigma K / S value is 120 or more
  • Sigma K / S value is 90 or more and less than 120
  • C Sigma K / S value is 60 or more and less than 90
  • D Sigma K / S value is less than 60
  • H * is 285 or more and less than 295
  • H * is 282 or more and less than 285, or 295 or more and less than 298
  • H * is 280 or more and less than 282, or 298 or more and less than 300
  • H * is 300 or more or less than 280
  • the light robustness test was performed according to the JIS L0843A method. That is, under the conditions of black panel temperature: 63 ° C, tank temperature: 38 ° C, relative humidity: 50%, irradiance: 50 W / m 2 (wavelength 300 to 400 nm), inner filter: quartz, outer filter: soda lime glass. , Xenon Weather Meter SUGA NX75 (manufactured by Suga Test Instruments Co., Ltd.) was used to irradiate each dyed product of 100% Duty obtained with a light source Xenon arc for 39.4 hours.
  • ⁇ Preparation Example 1f Preparation of aqueous dispersion 1f> C.
  • Disperse Blue 60 (10 parts), Laberin W-40 (Aqueous solution of sodium sulfonic acid sulfonic acid polycondensate, manufactured by Daiichi Kogyo Seiyaku Co., Ltd.) (15 parts), NIKKOL BPS-30 (0.8 parts), Surfinol 104PG50 (Surfinol 104 (acetylene glycol surfactant, manufactured by Air Products Japan Co., Ltd.) diluted to 50% concentration with propylene glycol) (0.2 part), Proxel GXL (S) (manufactured by Ronza) 0.2 mm diameter glass beads were added to a mixture consisting of (0.1 part) and ion-exchanged water (73.9 parts), and the mixture was subjected to dispersion treatment under cooling with a sand mill for about 15 hours.
  • the obtained liquid was filtered through a glass fiber filter paper GC-50 (manufacture
  • aqueous dispersion 2f Preparation of aqueous dispersion 2f> An aqueous dispersion 2f was obtained in the same manner as in Preparation Example 1f except that the colorant was changed to the compound represented by the formula (A1-1).
  • ⁇ Preparation Example 3f Preparation of Aqueous Dispersion Liquid 3f> An aqueous dispersion 3f was obtained in the same manner as in Preparation Example 1f except that the colorant was changed to the compound represented by the formula (A1-2).
  • aqueous dispersion 4f Preparation of aqueous dispersion 4f> An aqueous dispersion 4f was obtained in the same manner as in Preparation Example 1f except that the colorant was changed to the compound represented by the formula (A1-3).
  • ⁇ Preparation Example 5f Preparation of Aqueous Dispersion Liquid 5f> Compound represented by the formula (A1-1) (10 parts), Laberin W-40 (Aqueous solution of sodium sulfonic acid sulfonic acid polycondensate, manufactured by Daiichi Kogyo Seiyaku Co., Ltd.) (15 parts), Surfinol 104PG50 ( Surfinol 104 (acetylene glycol surfactant, manufactured by Air Products Japan Co., Ltd.) diluted with propylene glycol to a concentration of 50% (0.2 part), Proxel GXL (S) (manufactured by Ronza) (0.1) 0.2 mm diameter glass beads were added to the mixture consisting of ion-exchanged water (73.9 parts), and the mixture was subjected to dispersion treatment under cooling with a sand mill for about 15 hours. The obtained liquid was filtered through a glass fiber filter paper GC-50 (manufactured by ADVANTEC, filter pore size:
  • aqueous dispersion 6f Preparation of aqueous dispersion 6f> An aqueous dispersion 6f was obtained in the same manner as in Preparation Example 5f except that the colorant was changed to the compound represented by the formula (A1-2).
  • ⁇ Preparation Example 7f Preparation of aqueous dispersion 7f> Coloring agent C.I. I.
  • An aqueous dispersion 7f was obtained in the same manner as in Preparation Example 1f except that the mixture was changed to Disperse Blue 359 (10 parts).
  • aqueous dispersion 9f Preparation of aqueous dispersion 9f> An aqueous dispersion 9f was obtained in the same manner as in Preparation Example 5f except that the colorant was changed to Kayaset Yellow AG (CI Disperse Yellow 54, manufactured by Nippon Kayaku Co., Ltd.) (10 parts).
  • Kayaset Yellow AG CI Disperse Yellow 54, manufactured by Nippon Kayaku Co., Ltd.
  • Examples 1f to 4f and Comparative Examples 1f to 5f Preparation of ink set>
  • the inks obtained above were combined as shown in Table 19 below and filled into a cyan ink cartridge and a yellow ink cartridge, respectively, to obtain ink sets of Examples 1f to 4f and Comparative Examples 1f to 5f.
  • Example 1f in Table 19 the cyan ink cartridge was filled with ink 1f, and the yellow ink cartridge was filled with ink 8f.
  • a cyan ink cartridge and a yellow ink cartridge are loaded into an inkjet printer (manufactured by EPSON Co., Ltd., trade name PX-504A), and using TRANSJET EcoII 8385 (95 g / m 2 ) as an intermediate recording medium, 10 levels of each ink are used. Intermediate recording media on which a total of 100 patches were printed were obtained so as to form a matrix in which the key (print density) patterns were combined. More specifically, the printing Duties of the two types of inks constituting the ink set (cyan ink printing Duty / yellow ink printing Duty) are 100% / 10 to 100% and 90% / 10 to 100%, respectively.
  • C * is 70 or more
  • B C * is 65 or more and less than 70
  • C * is 60 or more and less than 65
  • D C * is less than 60-Evaluation criteria (when the hue angle is 165 ° to 170 °)-
  • Dc value is 1.25 or more
  • ⁇ Preparation Example 1 g Preparation of 1 g of aqueous dispersion> C.
  • Disperse Blue 60 (10 parts), Laberin W-40 (Aqueous solution of sodium sulfonic acid sulfonic acid polycondensate, manufactured by Daiichi Kogyo Seiyaku Co., Ltd.) (15 parts), NIKKOL BPS-30 (0.8 parts), Surfinol 104PG50 (Surfinol 104 (acetylene glycol surfactant, manufactured by Air Products Japan Co., Ltd.) diluted to 50% concentration with propylene glycol) (0.2 part), Proxel GXL (S) (manufactured by Ronza) 0.2 mm diameter glass beads were added to a mixture consisting of (0.1 part) and ion-exchanged water (73.9 parts), and the mixture was subjected to dispersion treatment under cooling with a sand mill for about 15 hours. The obtained liquid was filtered through a glass fiber filter paper GC-50 (manufact
  • ⁇ Preparation Example 2g Preparation of aqueous dispersion 2g> An aqueous dispersion (2 g) was obtained in the same manner as in Preparation Example 1 g except that the colorant was changed to the compound represented by the formula (A1-1).
  • ⁇ Preparation Example 3 g Preparation of aqueous dispersion 3 g> An aqueous dispersion (3 g) was obtained in the same manner as in Preparation Example 1 g except that the colorant was changed to the compound represented by the formula (A1-2).
  • ⁇ Preparation Example 4 g Preparation of aqueous dispersion 4 g> An aqueous dispersion (4 g) was obtained in the same manner as in Preparation Example 1 g except that the colorant was changed to the compound represented by the formula (A1-3).
  • ⁇ Preparation Example 5 g Preparation of aqueous dispersion 5 g> Compound represented by the formula (A1-1) (10 parts), SM-57 (polyoxyethylene styrylphenyl ether sulfate-based dispersant manufactured by Toho Chemical Industry Co., Ltd.) (10 parts), Surfinol 104PG50 (Surfinol 104).
  • Preparation Example 6 g Preparation of 6 g of aqueous dispersion> An aqueous dispersion (6 g) was obtained in the same manner as in Preparation Example 5 g except that the colorant was changed to the compound represented by the formula (A1-2).
  • ⁇ Preparation Example 7 g Preparation of 7 g of aqueous dispersion>
  • the compound represented by the formula (A1-1) (10 parts), the emulsion solution of Joncryl 678 (30 parts), and Surfinol 104PG50 (Surfinol 104 (acetylene glycol surfactant, manufactured by Air Products Japan Co., Ltd.) are propylene. 0.
  • glycol diluted to a concentration of 50%
  • Proxylene GXL (S) manufactured by Ronza
  • ion-exchanged water 59.7 parts).
  • ⁇ Preparation Example 9 g Preparation of aqueous dispersion 9 g> Coloring agent C.I. I.
  • An aqueous dispersion (9 g) was obtained in the same manner as in Preparation Example 1 g except that the mixture was changed to Disperse Blue 359.
  • ⁇ Preparation Example 10 g Preparation of 10 g of aqueous dispersion> Coloring agent C.I. I.
  • An aqueous dispersion (10 g) was obtained in the same manner as in Preparation Example 5 g except that the mixture was changed to Disperse Blue 359.
  • ⁇ Preparation Example 11 g Preparation of aqueous dispersion 11 g> Coloring agent C.I. I. 11 g of the aqueous dispersion was obtained in the same manner as in Preparation Example 7 g except that the mixture was changed to Disperse Blue 359.
  • ⁇ Preparation Example 12 g Preparation of aqueous dispersion 12 g> An aqueous dispersion (12 g) was obtained in the same manner as in Preparation Example 1 g except that the colorant was changed to the compound represented by the formula (B1-1).
  • ⁇ Preparation Example 13 g Preparation of aqueous dispersion 13 g> An aqueous dispersion (13 g) was obtained in the same manner as in Preparation Example 5 g except that the colorant was changed to the compound represented by the formula (B1-1).
  • ⁇ Preparation Example 14 g Preparation of aqueous dispersion 14 g> An aqueous dispersion (14 g) was obtained in the same manner as in Preparation Example 7 g except that the colorant was changed to the compound represented by the formula (B1-1).
  • Examples 1 g to 14 g and Comparative Examples 1 g to 3 g Preparation of ink set> The inks obtained above were combined as shown in Tables 23 and 24 below and filled into a cyan ink cartridge and a yellow ink cartridge, respectively, to obtain ink sets of Examples 1 g to 14 g and Comparative Examples 1 g to 3 g.
  • the cyan ink cartridge was filled with 1 g of ink
  • the yellow ink cartridge was filled with 12 g of ink.
  • a cyan ink cartridge and a yellow ink cartridge are loaded into an inkjet printer (manufactured by EPSON Co., Ltd., trade name PX-504A), and using TRANSJET EcoII 8385 (95 g / m 2 ) as an intermediate recording medium, 10 levels of each ink are used. Intermediate recording media on which a total of 100 patches were printed were obtained so as to form a matrix in which the key (print density) patterns were combined. More specifically, the printing Duties of the two types of inks constituting the ink set (cyan ink printing Duty / yellow ink printing Duty) are 100% / 10 to 100%, 90% / 10 to 100%, respectively.
  • ⁇ Preparation Example 1h Preparation of aqueous dispersion 1h> Kayaset Yellow AG (manufactured by Nippon Kayaku Co., Ltd., CI Disperse Yellow 54) (10 parts), Laberin W-40 (Aqueous solution of sodium sulphonate polycondensate in creoseto oil, manufactured by Daiichi Kogyo Seiyaku Co., Ltd.) (15 parts), NIKKOL BPS-30 (0.8 parts), Surfinol 104PG50 (Surfinol 104 (acetylene glycol surfactant, manufactured by Air Products Japan Co., Ltd.) diluted to 50% concentration with propylene glycol) Add 0.2 mm diameter glass beads to a mixture consisting of (0.2 part), Proxel GXL (S) (manufactured by Ronza) (0.1 part), and ion-exchanged water (73.9 parts), and use a sand mill.
  • Kayaset Yellow AG manufactured by Nippon Kayaku Co., Ltd.,
  • the dispersion treatment was carried out for about 15 hours under cooling.
  • the obtained liquid was filtered through a glass fiber filter paper GC-50 (manufactured by ADVANTEC, filter pore size: 0.5 ⁇ m) to obtain an aqueous dispersion liquid 1h.
  • ⁇ Preparation Example 2h Preparation of Aqueous Dispersion Liquid 2h> Coloring agent C.I. I.
  • An aqueous dispersion 2h was obtained in the same manner as in Preparation Example 1h except that the mixture was changed to Disperse Blue 359.
  • ⁇ Preparation Example 3h Preparation of Aqueous Dispersion Liquid 3h> An aqueous dispersion 3h was obtained in the same manner as in Preparation Example 1h except that the colorant was changed to the compound represented by the formula (G1).
  • ⁇ Preparation Example 4h Preparation of Aqueous Dispersion Liquid 4h> An aqueous dispersion 4h was obtained in the same manner as in Preparation Example 1h except that the colorant was changed to the compound represented by the formula (A1-1).
  • ⁇ Preparation Example 5h Preparation of Aqueous Dispersion Liquid 5h> An aqueous dispersion 5h was obtained in the same manner as in Preparation Example 1h except that the colorant was changed to the compound represented by the formula (A1-2).
  • ⁇ Preparation Example 6h Preparation of Aqueous Dispersion Liquid 6h> C.
  • 0.2 mm diameter glass beads were added to the mixture consisting of (0.2 parts), Propylene GXL (S) (manufactured by Ronza) (0.1 parts), and ion-exchanged water (59.7 parts).
  • the dispersion treatment was carried out for about 15 hours under cooling with a sand mill.
  • the obtained liquid was filtered through a glass fiber filter paper GC-50 (manufactured by ADVANTEC, filter pore size: 0.5 ⁇ m) to obtain an aqueous dispersion liquid 6h.
  • ⁇ Preparation Example 7h Preparation of Aqueous Dispersion Liquid 7h> An aqueous dispersion 7 was obtained in the same manner as in Preparation Example 6h except that the colorant was changed to the compound represented by the formula (A1-1).
  • ⁇ Preparation Example 8h Preparation of Aqueous Dispersion Liquid 8h> C.
  • 0.2 mm diameter glass beads were added to the mixture consisting of 7 parts), and the mixture was subjected to dispersion treatment for about 15 hours under cooling with a sand mill.
  • the obtained liquid was filtered through a glass fiber filter paper GC-50 (manufactured by ADVANTEC, filter pore size: 0.5 ⁇ m) to obtain an aqueous dispersion liquid 8h.
  • ⁇ Preparation Example 9h Preparation of Aqueous Dispersion Liquid 9h> An aqueous dispersion 9h was obtained in the same manner as in Preparation Example 8h except that the colorant was changed to the compound represented by the formula (A1-1).
  • Examples 1h to 9h and Comparative Example 1h Preparation of ink set>
  • the inks obtained above were combined as shown in Table 28 below and filled into a magenta ink cartridge and a cyan ink cartridge, respectively, to obtain ink sets of Examples 1h to 9h and Comparative Example 1h, respectively.
  • the magenta ink cartridge was filled with ink 2h
  • the cyan ink cartridge was filled with ink 4h.
  • a magenta ink cartridge and a cyan ink cartridge are loaded into an inkjet printer (manufactured by EPSON Co., Ltd., trade name PX-504A), and using TRANSJET EcoII 8385 (95 g / m 2 ) as an intermediate recording medium, 10 levels of each ink are used. Intermediate recording media on which a total of 100 patches were printed were obtained so as to form a matrix in which the key (print density) patterns were combined. More specifically, the printing Duties of the two types of inks constituting the ink set (magenta ink printing Duty / cyan ink printing Duty) are 100% / 10 to 100% and 90% / 10 to 100%, respectively.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Dispersion Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Ink Jet Recording Methods And Recording Media Thereof (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)

Abstract

L'invention fournit un liquide colorant qui comprend un agent colorant non soluble dans l'eau présentant une longueur d'onde d'absorption maximale dans une plage de longueur d'onde supérieure à 640nm et inférieure ou égale à 700nm, et dans lequel ｂ＊ représenté par l'espace colorimétrique CIE se trouve à l'intérieur d'une plage de －３０ à －２０ lorsque l'absorbance dans la longueur d'onde d'absorption maximale vaut 1, et qui comprend un agent colorant non soluble dans l'eau, ou similaire, présentant une longueur d'onde d'absorption maximale dans une plage de longueur d'onde supérieure ou égale à 410nm et inférieure ou égale à 450nm. L'invention fournit également un ensemble d'encres contenant ce liquide colorant en tant qu'encre. En outre, l'invention fournit un support d'enregistrement sur lequel se trouve en adhésion ledit liquide colorant ou chaque encre contenue dans ledit ensemble d'encre, et un procédé d'impression sur textile pour fibres hydrophobes mettant en œuvre ledit liquide colorant ou ledit ensemble d'encre.
PCT/JP2021/027675 2020-07-31 2021-07-27 Liquide colorant, ensemble d'encres, support d'enregistrement, et procédé d'impression sur textile pour fibres hydrophobes Ceased WO2022025034A1 (fr)

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Citations (8)

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Publication number Priority date Publication date Assignee Title
JPS53134982A (en) * 1977-04-25 1978-11-25 Ici Ltd Transfer printing of synthetic fiber material
JP2006502313A (ja) * 2002-06-05 2006-01-19 クラリアント インターナショナル リミティド ポリエステル生地材料の染色
JP2007238687A (ja) * 2006-03-06 2007-09-20 Nippon Kayaku Co Ltd インクジェット捺染方法
WO2012060343A1 (fr) * 2010-11-04 2012-05-10 日本化薬株式会社 Composition d'encre à colorant azoïque et ensemble encre d'impression à jet d'encre l'utilisant
JP5039022B2 (ja) * 2006-03-06 2012-10-03 日本化薬株式会社 インクジェット捺染用インク及びそれを用いるインクジェット捺染方法
JP2013053234A (ja) * 2011-09-03 2013-03-21 Nippon Kayaku Co Ltd 分散染料混合物、それを含有する染料組成物及びそれを用いた染色法
WO2013129523A1 (fr) * 2012-02-28 2013-09-06 日本化薬株式会社 Encre pour jet d'encre à base d'eau permettant la détection de falsification de document, procédé d'impression à jet d'encre l'utilisant et les documents imprimés par ce procédé
WO2018178890A1 (fr) * 2017-03-29 2018-10-04 Jk Group S.P.A. Nouvelle encre noire

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS57199881A (en) * 1981-06-01 1982-12-07 Du Pont Level dyeing of fiber material by heat transfer
WO2020017432A1 (fr) * 2018-07-19 2020-01-23 日本化薬株式会社 Composition d'encre noire pour impression à jet d'encre et procédé d'impression sur fibres hydrophobes
JP7347189B2 (ja) * 2019-12-16 2023-09-20 セイコーエプソン株式会社 昇華転写インクジェットインク組成物及び印刷物の製造方法

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS53134982A (en) * 1977-04-25 1978-11-25 Ici Ltd Transfer printing of synthetic fiber material
JP2006502313A (ja) * 2002-06-05 2006-01-19 クラリアント インターナショナル リミティド ポリエステル生地材料の染色
JP2007238687A (ja) * 2006-03-06 2007-09-20 Nippon Kayaku Co Ltd インクジェット捺染方法
JP5039022B2 (ja) * 2006-03-06 2012-10-03 日本化薬株式会社 インクジェット捺染用インク及びそれを用いるインクジェット捺染方法
WO2012060343A1 (fr) * 2010-11-04 2012-05-10 日本化薬株式会社 Composition d'encre à colorant azoïque et ensemble encre d'impression à jet d'encre l'utilisant
JP2013053234A (ja) * 2011-09-03 2013-03-21 Nippon Kayaku Co Ltd 分散染料混合物、それを含有する染料組成物及びそれを用いた染色法
WO2013129523A1 (fr) * 2012-02-28 2013-09-06 日本化薬株式会社 Encre pour jet d'encre à base d'eau permettant la détection de falsification de document, procédé d'impression à jet d'encre l'utilisant et les documents imprimés par ce procédé
WO2018178890A1 (fr) * 2017-03-29 2018-10-04 Jk Group S.P.A. Nouvelle encre noire

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