WO2017073068A1 - Composition d'émulsion d'encre et encre aqueuse - Google Patents

Composition d'émulsion d'encre et encre aqueuse Download PDF

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Publication number
WO2017073068A1
WO2017073068A1 PCT/JP2016/004737 JP2016004737W WO2017073068A1 WO 2017073068 A1 WO2017073068 A1 WO 2017073068A1 JP 2016004737 W JP2016004737 W JP 2016004737W WO 2017073068 A1 WO2017073068 A1 WO 2017073068A1
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Prior art keywords
ink
component
emulsion composition
composition according
group
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PCT/JP2016/004737
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English (en)
Japanese (ja)
Inventor
桂丈 佐々木
慎介 清水
俊太 三澤
順哉 柵木
比呂子 樋口
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日本化薬株式会社
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Priority to JP2017547626A priority Critical patent/JP6954838B2/ja
Publication of WO2017073068A1 publication Critical patent/WO2017073068A1/fr

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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
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D11/00—Inks
    • C09D11/02—Printing inks
    • C09D11/023—Emulsion 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
    • C09D11/32—Inkjet printing inks characterised by colouring agents

Definitions

  • the present invention relates to a novel ink emulsion composition having very high storage stability and a water-based ink composition using the same.
  • Inkjet printing is widely used as a printer for office and home use as information is digitized, but in recent years, many applications have been developed for commercial printing and textile printing.
  • the colorants used in ink vary from conventional water-soluble dyes such as acid dyes or direct dyes to water-insoluble color materials such as disperse dyes and pigments. Color materials have come to be used.
  • disperse dyes are widely used for industrial dyeing of hydrophobic fibers such as polyester, and water-insoluble dyes are dispersed in a dye bath or color paste and used for dyeing.
  • the dye penetrates and diffuses in a dispersed state inside the fiber under high temperature conditions, and is dyed by hydrogen bonds between fiber dyes or intermolecular forces. If the dispersibility of the dye, particularly the dispersibility at high temperature, is inferior, the agglomeration of the dye occurs in the high-temperature dyeing bath, and specs on the fiber (dyes that are poorly dispersed at the time of dyeing adhere to the fiber in the form of dots. Phenomenon that causes stains).
  • dispersants having excellent high-temperature dispersibility such as formaldehyde condensates of lignin sulfonic acid, formaldehyde condensates of alkylnaphthalene sulfonic acid, formaldehyde condensate of creosote oil sulfonic acid, etc.
  • System dispersants have been mainly used.
  • Non-patent Document 1 Inkjet printing of polyester fibers using disperse dyes has also been carried out (Non-patent Document 1, Non-patent Document 2).
  • dye ink is applied (printed) mainly to the fiber, the dye is applied by heat treatment such as steaming.
  • a direct printing method for dyeing and a thermal transfer printing method in which dye ink is applied (printed) to a dedicated transfer paper and then sublimated and transferred from the transfer paper side to the fiber side by heat are put into practical use.
  • anionic dispersants conventionally used for industrial dyeing are used (Patent Documents 1 and 2).
  • Patent Document 3 uses the dispersant represented by Formula 1 and has good ejection stability, but it has been found that there is still a problem in sedimentation stability (storage stability).
  • the ink composition used for ink jet recording and the colored bodies colored thereby are highly colored and have various fastnesses such as light resistance and water resistance. There is a need to be good. Further, ink compositions used for ink jet recording are strongly required to be stable as ink for a long period of time and to be dissolved or dispersed again in water when dried.
  • disperse dyes are required to be stable for a long time.
  • a dye that exists in a dispersed state as particles instead of molecules in an ink undergoes a sedimentation phenomenon over time due to aggregation of the dye particles.
  • a density gradient occurs in the ink, and the initial printing characteristics cannot be obtained, or in the worst case, the aggregated particles are clogged in the nozzle and cannot be ejected.
  • Patent Document 6 An ink composition in which a dispersion is prepared using a polymer dispersant.
  • Patent Document 5 discloses an ink composition using a self-dispersing pigment.
  • Patent Document 8 discloses a production method thereof.
  • none of the ink compositions has yet provided a product that sufficiently satisfies the market demand.
  • the present invention solves the above-mentioned problems in the prior art, and the storage stability of the dispersion is good. Even when used as an ink composition, the stability is good, and even when stored for a long time, the physical properties of the ink change. It aims at providing the emulsion composition for inks which does not produce.
  • the present inventors are an emulsion liquid containing a colorant having a core-shell structure using a styrene-acrylic copolymer, wherein the core layer of the component (A) is: It has been found that by preparing an aqueous ink composition which is a dye and / or pigment and whose shell layer is a styrene-acrylic copolymer, the storage stability of the dispersion is remarkably improved.
  • Dispersion of water-insoluble colorants with an anionic dispersant prevents pigment particles from re-aggregating due to the electrostatic repulsion of the pigment surface caused mainly by adsorption of the ionic active agent, resulting in a stable dispersion state. It is believed that According to the estimations of the present inventors, it is considered that conventional anionic dispersants have poor dispersion stability over time and with heat because the adsorptive power to colorants is weak. In the specific dispersant of the present invention, the styrene-acrylic copolymer becomes a shell layer and encloses the insoluble dye, so that the aggregation of the dyes is eliminated and the stability may be improved.
  • the present invention relates to the following 1) to 20).
  • the core layer of the component (A) is C.I. I. Disperse Yellow 54, C.I. I. Disperse Orange 25, C.I. I. Disperse thread 60, C.I. I. Disperse Blue 72, 359, 360, C.I. I. Disperse Brown 26, 27 and C.I. I.
  • n 1 to n 3 represent an integer of 1 to 30.
  • m 1 and m 2 represent an integer of 1 to 43.
  • R represents the alkylene group, alkylidene group, and arylene group which may have a substituent.
  • an ink emulsion composition having excellent storage stability is obtained, and by using this, an aqueous dispersion of a water-insoluble colorant and an ink composition can be realized.
  • the ink emulsion composition of the present invention comprises (A) a colorant having a core-shell structure, the core layer being a dye and / or pigment, and the shell layer being a styrene- (meth) acrylic copolymer. To do.
  • the emulsion composition of the present invention is a mixture produced when two types of liquids that do not dissolve each other are vigorously stirred.
  • oil is emulsified in water or water is emulsified in oil.
  • the core layer of the component (A) included in the emulsion composition for ink of the present invention is a dye and / or a pigment.
  • the above dyes are organic dyes that are dyed on fibers by an appropriate dyeing method.
  • direct dyes vat dyes, sulfur dyes, disperse dyes, basic dyes, naphthol dyes, acid dyes, acid mordant dyes, mordants And dyes, oil-soluble dyes, reactive dyes, soluble vat dyes, sulfur vat dyes, and oxidation dyes.
  • Disperse Yellow 3, 4, 5, 7, 8, 9, 13, 23, 24, 30, 33, 34, 39, 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, 149, 160, 162, 163, 164, 165, 179, 180, 182, 183, 186, 192, 198, 199, 200, 202, 204, 210, 211, 215, 216 218, 224, 237 and the like.
  • C.I. I. Disperse Orange is as follows: 1, 1: 1, 3, 5, 7, 11, 13, 17, 20, 21, 23, 24, 25, 25: 1, 29, 30, 31, 32, 33, 37, 38 , 42, 43, 44, 45, 47, 48, 49, 50, 53, 54, 55, 56, 57, 58, 59, 61, 66, 71, 73, 76, 78, 80, 86, 89, 90 91, 93, 96, 97, 118, 119, 127, 130, 139, 142, and the like.
  • C.I. I. Disperse Red is 1, 4, 5, 7, 11, 12, 13, 15, 17, 27, 43, 44, 50, 52, 53, 54, 55, 55: 1, 56, 58, 59, 60.
  • C.I. I. Disperse violet 1, 4, 8, 11, 17, 23, 26, 27, 28, 29, 31, 33, 35, 36, 38, 40, 43, 46, 48, 49, 50, 51, 52, 56 57, 59, 61, 63, 69, 77, 97, C.I. I. Disperse Green 9, C.I. I. Disperse brown 1, 2, 4, 9, 13, 19, 26, 27, C.I. I.
  • the pigment is a white or colored powder insoluble in water, an organic solvent, or the like, and includes an organic pigment and an inorganic pigment.
  • an organic pigment or an inorganic pigment may be used, but an organic pigment is preferred.
  • a dye is more preferable, and at least one dye selected from a disperse dye, an oil-soluble dye, and a vat dye is even more preferable.
  • examples of the dye suitable for thermal transfer include C.I. I. Disperse yellow 51, 54, 60, 71, 82, 211, C.I. I. Disperse orange 5, 7, 20, 23, 24, 25, 25: 1, C.I. I. Disperse thread 4, 11, 50, 53, 59, 60, 239, 240, 364, C.I. I. Disperse violet 8, 11, 17, 26, 27, 28, 36, C.I. I.
  • Disperse Blue 3, 5, 26, 35, 55, 56, 72, 81, 91, 108, 334, 359, 360, 366, C.I. I. Disperse Brown 26, 27, C.I. I. Solvent Yellow 114, C.I. I. Solvent Orange 60, 67, C.I. I. Solvent Red 146, C.I. I. Solvent Blue 36, 63, 83, 105, 111 etc. can be mentioned, More preferably, C.I. I. Disperse Yellow 54, C.I. I. Disperse Orange 25, C.I. I. Disperse thread 60, C.I. I. Disperse blue 72,359,360, C.I. I. Disperse Brown 26, 27, C.I. I. Solvent Orange 60 and the like, particularly preferably C.I. I. Disperse Yellow 54, C.I. I. Disperse Orange 25, C.I. I. This is a disperse thread 60.
  • color materials may be powdery or lump dry color materials, wet cakes or slurries, and contain a small amount of a dispersant such as a surfactant for the purpose of suppressing aggregation of the color material particles during or after the color material synthesis. It may be a thing.
  • a dispersant such as a surfactant for the purpose of suppressing aggregation of the color material particles during or after the color material synthesis. It may be a thing.
  • These commercially available color materials include industrial dyeing grades, resin coloring grades, ink grades, toner grades, and inkjet grades, which differ in production method, purity, pigment particle size, and the like.
  • the colorant preferably has smaller particles, and preferably has as few impurities as possible in view of the influence on dispersion stability and ink ejection accuracy.
  • the dye can be used as a color material for black by blending an orange dye and a red dye mainly with a blue dye. Further, a small amount of other water-insoluble colorant may be
  • the above dyes may be blended.
  • an orange dye and a red dye mainly composed of a blue dye are appropriately blended to adjust the color to a black color, and this can be used as a black dye.
  • a plurality of dyes may be blended for the purpose of finely adjusting a color tone such as blue, orange, red, violet, or black to a color tone that is more preferred.
  • the shell layer of component (A) contained in the ink emulsion composition of the present invention is a styrene- (meth) acrylic copolymer, which is a copolymer of a styrene monomer and a (meth) acrylic monomer.
  • (meth) acryl means “acryl” and / or “methacryl”.
  • Specific examples of these copolymers include ( ⁇ -methyl) styrene-acrylic acid copolymer, ( ⁇ -methyl) styrene-acrylic acid-acrylic acid ester copolymer, ( ⁇ -methyl) styrene-methacrylic acid.
  • the compound containing an aromatic hydrocarbon group is preferably styrene-methacrylic acid-acrylic acid ester copolymer, ( ⁇ -methyl) styrene- (anhydrous) maleic acid copolymer, acrylic acid ester- (anhydrous) maleic acid copolymer, ( ⁇ -methyl) styrene-acrylic acid ester- (anhydrous) maleic acid copolymer, acrylic acid ester-allylsulfonic acid ester copolymer, acrylic acid ester-styrenesulfonic acid copolymer, ( ⁇ -methyl) styrene- Methacrylsulfonic acid copolymer, polyester-acrylic acid copolymer, polyester-acrylic acid-acrylic acid ester copolymer, Riesuteru - methacrylic acid copolymer, polyester - methacrylic acid - acrylic acid copolymer ester; and the like.
  • the compound containing an aromatic hydrocarbon group is preferably st
  • styrene- (meth) acrylic copolymer used as the shell layer of the component (A) in the present invention include Joncryl RTM 52J, 57J, 60J, 63J, 70J, JDX-6180, HPD-196, HPD96J, Examples thereof include, but are not limited to, PDX-6137A, 6610, JDX-6500, JDX-6663, PDX-6102B, PDX-6124 (manufactured by BASF).
  • the superscript RTM means a registered trademark.
  • the styrene- (meth) acrylic copolymer used as the shell layer of component (A) in the present invention preferably has a weight average molecular weight of 1000 to 20000, more preferably 2000 to 19000, and more preferably 4000 to 17000. Particularly preferred. If the weight average molecular weight is too small, the dispersion stabilizing ability with respect to the sublimable dye is lowered, and if it is too large, the ability to disperse the sublimable dye is lowered, and the viscosity of the ink may be too high. .
  • the weight average molecular weight of the styrene-acrylic acid copolymer is measured by GPC (gel permeation chromatograph) method.
  • the glass transition temperature of the styrene- (meth) acrylic copolymer used as the shell layer of component (A) is preferably 45 ° C to 135 ° C, more preferably 55 ° C to 120 ° C, and 60 ° C to 110 ° C. Is particularly preferred.
  • the acid value of the styrene- (meth) acrylic copolymer used as the shell layer of component (A) is preferably 50 to 250 mgKOH / g, more preferably 100 to 250 mgKOH / g, and 150 to 250 mgKOH / g. Is particularly preferred.
  • the acid value of the resin represents the number of mg of KOH required to neutralize 1 g of the resin, and is measured according to JIS-K3054.
  • styrene- (meth) acrylic copolymer used as the shell layer of the component (A) in the present invention those having a skeleton represented by the above formula (1) and / or (2) in the molecule are preferable.
  • n 1 to n 3 represent an integer of 1 to 30.
  • m 1 and m 2 represent an integer of 1 to 43.
  • the emulsion composition for ink of the present invention is preferably produced, for example, by the following method.
  • the styrene-acrylic copolymer is put into a water-soluble organic solvent, and the temperature is raised to 90-120 ° C. to prepare a styrene-acrylic copolymer solution.
  • a neutralizing agent and water are added thereto, the temperature is lowered to obtain an emulsion (emulsion or microemulsion) liquid, and the emulsion liquid thus prepared and the dye and / or pigment are mixed and dispersed, thereby the dye.
  • emulsion emulsion or microemulsion
  • examples of the water-soluble organic solvent include glycerin (boiling point: 290 ° C), ethylene glycol, propylene glycol (boiling point: 188 ° C), dipropylene glycol (boiling point: 230 ° C), butyl carbitol (boiling point: 231 ° C).
  • Methyl triglycol triethylene glycol, butyl triglycol, butyl carbitol acetate (boiling point: 247 ° C.), diethylene glycol, 1,5 pentadiol, 1,6 hexanediol, 1,2-hexanediol, methyldiglycol, Tripropylene glycol, methanol (boiling point: 64 ° C), ethanol (boiling point: 78 ° C), 1-propanol (boiling point: 97 ° C), 2-propanol (boiling point: 82 ° C), 1,2-methoxyethane (boiling point: 93 ° C), tetrahydrofuran (boiling point: 66 ° C), p-dioxane (boiling point: 101 ° C), etc. It is. These water-soluble organic solvents may be used alone or in combination.
  • the ink emulsion composition before being mixed with the dye and / or pigment is neutralized with a neutralizing agent and then mixed with water, it is necessary to use a neutralizing agent.
  • the neutralizing agent include alkali metal hydroxides, alkaline earth metal hydroxides, aliphatic amine compounds, and alcohol amine compounds.
  • alkali metal hydroxide examples include lithium hydroxide, sodium hydroxide, and potassium hydroxide.
  • alkaline earth metal hydroxide examples include beryllium hydroxide, magnesium hydroxide, calcium hydroxide, and strontium hydroxide.
  • the neutralizing agent is preferably an alkali metal hydroxide, more preferably lithium hydroxide, sodium hydroxide or potassium hydroxide, and still more preferably potassium hydroxide.
  • Examples of the alcohol amine compound include monoethanolamine, diethanolamine, triethanolamine, monopropanolamine, dipropanolamine, tripropanolamine, methylethanolamine, dimethylethanolamine and N-methyldiethanolamine, preferably tertiary amine. More preferably, it is triethanolamine.
  • Examples of the aliphatic amine compound include ammonia, monomethylamine, dimethylamine, trimethylamine, monoethylamine, diethylamine and triethylamine, preferably ammonia or triethylamine.
  • neutralizers may be used alone or in combination.
  • the amount of the emulsion liquid to be used is preferably 10% to 300%, more preferably 10% to 250%, and particularly preferably 20% to 200%, based on mass with respect to the dye and / or pigment.
  • examples of the dispersion method include a method using a sand mill (bead mill), a roll mill, a ball mill, a paint shaker, an ultrasonic disperser, a microfluidizer, and the like.
  • a sand mill (bead mill) is preferable.
  • the pulverization of the coloring material in the sand mill it is preferable to use beads having a small diameter, and to perform the treatment under a condition in which the pulverization efficiency is increased by increasing the filling rate of the beads. It is preferable to remove elementary particles by centrifugation or the like.
  • ink emulsion compositions have foaming properties, it is preferable to use pulverization conditions that suppress foaming at the time of pulverization as much as possible in order to improve pulverization efficiency.
  • An antifoaming agent or the like may be added in an extremely small amount during pigment grinding.
  • some antifoaming agents inhibit dispersion and micronization, and it is necessary to use those that do not affect the stability after micronization or dispersion.
  • the dispersion can be diluted with a small amount of water and adjusted to a desired colorant concentration.
  • the ink emulsion composition of the present invention preferably has a number average particle size of component (A) of 10 to 500 nm.
  • the number average particle size of the component (A) is 10 to 500 nm, the storage stability and sedimentation property of the composition are excellent.
  • the number average particle diameter is measured according to a dynamic light scattering particle size distribution measuring apparatus or a small angle X-ray scattering method.
  • the content of the coloring matter (dye, pigment) in the component (A) is preferably in the range of 0.1 to 30% by mass, and more preferably in the range of 5 to 20% by mass.
  • dye in the emulsion composition for inks exists in the said range, the storage stability and sedimentation property of a composition are excellent.
  • the mass ratio of the dye and / or pigment of the core layer to the styrene- (meth) acrylic copolymer of the shell layer is 90:10 to 25:75.
  • the range of 70:30 to 50:50 is more preferable.
  • the mass ratio of the core layer to the shell layer is within the above range, the storage stability and sedimentation of the composition are excellent.
  • Component (B) of the present invention is a compound having both amino group and sulfo group substituents in the molecule. It is considered that this compound is ionically bonded to the carboxy group of component (A) and behaves as having a terminal sulfo group, thereby improving stability.
  • component (B) a compound represented by the above formula (3) is preferable.
  • R in the above formula (3) represents an alkylene group which may have a substituent, an alkylidene group which may have a substituent, or an arylene group which may have a substituent.
  • the alkylene group which may have a substituent is a saturated or unsaturated, linear or cyclic (preferably C1-C20) alkylene group, and may have a hetero atom.
  • a methylene group, an ethylene group, a propylene group, a butylene group, a cyclopentylene group, a cyclohexylene group, a norbornylene group, an adamantylene group, and the like can be given, preferably a (C1-C10) alkylene group, A (C1-C5) alkylene group is preferred, and a methylene group, ethylene group, and propylene group are particularly preferred.
  • examples of the substituent that may be included include a halogen atom; a cyano group; a hydroxy group; a carboxy group; a sulfo group; a sulfamoyl group; a (C1-C4) alkoxy group; a hydroxy group, a (C1-C4) alkoxy group, A (C1-C4) alkoxy group substituted with at least one group selected from the group consisting of a sulfo group and a carboxy group; an N-alkylaminosulfonyl group; an N-phenylaminosulfonyl group; a phospho group; a nitro group; (C1-C6) substituted with at least one group selected from the group consisting of acyl group; ureido group; acylamino group, (C1-C4) alkoxy group, sulfo group and carboxy group An alkyl group etc.
  • the alkylidene group which may have a substituent is a saturated or unsaturated, linear or cyclic (preferably C1-C20) alkylidene group, and may have a hetero atom.
  • a substituent preferably C1-C20 alkylidene group
  • an ethylidene group, a propylidene group, a butylidene group, a cyclopentylidene group, a cyclohexylidene group, a norbornylidene group, an adamantylidene group, and the like can be given, and a (C1-C10) alkylidene group is preferable, and more preferable.
  • the arylene group which may have a substituent is a (preferably C1-C20) arylene group, which may have a hetero atom.
  • it represents a phenylene group, a thienylene group, a pyrrolylene group, etc., but two or more ring structures may be condensed, such as a naphthylene group, an anthranylene group, a phenanthrylene group, or a quinolylene group.
  • R may have an ester structure (—COO—), an ether structure (—O—), or a keto structure (— (C ⁇ O) —).
  • Specific examples of the compound represented by the above formula (3) include taurine, 4-amino-1-naphthalenesulfonic acid, hydroxylaminosulfonic acid, 5-amino-1-naphthalenesulfonic acid, hydroxylaminosulfonic acid, 6 -Amino-1-naphthalenesulfonic acid, hydroxylaminosulfonic acid, 3-amino-2,7-naphthalenedisulfonic acid, 2-amino-1,4-benzenesulfonic acid, 4-aminobenzenesulfonic acid and the like.
  • the content of component (B) is preferably in the range of 0.1 to 40% by mass, and more preferably in the range of 1 to 20% by mass.
  • the stability of the ink emulsion composition is improved by solvation due to the influence of the sulfo group.
  • the ink emulsion composition of the present invention may further contain (C) a water-soluble organic solvent.
  • the water-soluble organic solvent include (C1-C4) alcohols such as methanol, ethanol, propanol, isopropanol, butanol, isobutanol, sec-butanol and tert-butanol; N, N-dimethylformamide, N, Carboxylic acid amides such as N-dimethylacetamide; Lactams such as 2-pyrrolidone, hydroxyethyl-2-pyrrolidone, N-methyl-2-pyrrolidone, N-methylpyrrolidin-2-one; 1,3-dimethylimidazolidine-2 -Cyclic ureas such as 1,3-dimethylhexahydropyrimido-2-one; ketones or ketoalcohols such as acetone, methyl ethyl ketone, 2-methyl
  • Component (C) is preferably a water-soluble organic solvent having one or more hydroxy groups in the molecule.
  • the content of component (C) is preferably in the range of 1 to 60% by mass, and more preferably in the range of 10 to 30% by mass.
  • An ink dispersion composition in which (D) an antifoaming agent is further added to the above-described ink emulsion composition may be provided.
  • An antifoaming agent is a substance having an action of eliminating bubbles in a solution or suppressing foaming, and examples thereof include oily substances (such as higher alcohols) having low volatility and high diffusibility, and nonionic surfactants.
  • Nonionic surfactants include ethers such as polyoxyethylene nonylphenyl ether, polyoxyethylene octylphenyl ether, polyoxyethylene dodecylphenyl ether, polyoxyethylene oleyl ether, polyoxyethylene lauryl ether, polyoxyethylene alkyl ether; Ester systems such as polyoxyethylene oleate, polyoxyethylene distearate, sorbitan laurate, sorbitan monostearate, sorbitan monooleate, sorbitan sesquioleate, polyoxyethylene monooleate, polyoxyethylene stearate; 2,4,7,9-tetramethyl-5-decyne-4,7-diol, 3,6-dimethyl-4-octyne-3,6-diol, 3,5-dimethyl Acetylene glycol (alcohol) type such as lu-1-hexyn-3-ol; trade name Surfynol 104, 105, 82, 465
  • the content of component (D) is preferably in the range of 0.01 to 0.5% by mass, more preferably in the range of 0.05 to 0.3% by mass.
  • Component (E) Preservative It can also be set as the ink dispersion composition which added the (E) antiseptic
  • preservatives include organic sulfur, organic nitrogen sulfur, organic halogen, haloaryl sulfone, iodopropargyl, haloalkylthio, nitrile, pyridine, 8-oxyquinoline, benzothiazole , Isothiazoline, dithiol, pyridine oxide, nitropropane, organotin, phenol, quaternary ammonium salt, triazine, thiazine, anilide, adamantane, dithiocarbamate, brominated indanone, benzyl Examples thereof include bromoacetate-based or inorganic salt-based compounds.
  • organic halogen compounds include, for example, pentachlorophenol sodium
  • specific examples of pyridine oxide compounds include, for example, 2-pyridinethiol-1-oxide sodium
  • isothiazoline compounds include, for example, 1,2-benzisothiazolin-3-one, 2-n-octyl-4-isothiazolin-3-one, 5-chloro-2-methyl-4-isothiazolin-3-one, 5-chloro-2-methyl-4 -Isothiazolin-3-one magnesium chloride, 5-chloro-2-methyl-4-isothiazolin-3-one calcium chloride, 2-methyl-4-isothiazolin-3-one calcium chloride and the like.
  • the other preservatives include anhydrous sodium acetate, sodium sorbate or sodium benzoate, trade names Proxel RTM GXL (S), Proxel RTM XL-2 (S), etc.
  • the content of component (E) is preferably in the range of 0.01 to 0.5% by mass, and more preferably in the range of 0.1 to 0.3% by mass.
  • the content of the component (E) in the ink dispersion composition is within the above range, it has a fungicidal action and can suppress thickening and the like.
  • the emulsion composition for ink of the present invention has an antifungal agent, a pH adjuster, a chelating reagent, an antirust agent, and a water-soluble agent.
  • Antidepressant examples include sodium dehydroacetate, sodium benzoate, sodium pyridinethione-1-oxide, p-hydroxybenzoic acid ethyl ester, 1,2-benzisothiazolin-3-one and salts thereof.
  • an antifungal agent it is preferable to use 0.02 to 1.00% by mass in the emulsion composition.
  • any substance can be used as long as it can control the pH of the ink within a range of about 5 to 11 without adversely affecting the prepared ink.
  • specific examples thereof include, for example, alkanolamines such as diethanolamine, triethanolamine and N-methyldiethanolamine; hydroxides of alkali metals such as lithium hydroxide, sodium hydroxide and potassium hydroxide; ammonium hydroxide (ammonia water) Alkali metal carbonates such as lithium carbonate, sodium carbonate, sodium hydrogen carbonate and potassium carbonate; alkali metal salts of organic acids such as potassium acetate; inorganic bases such as sodium silicate and disodium phosphate.
  • chelating reagent examples include sodium ethylenediaminetetraacetate, sodium nitrilotriacetate, sodium hydroxyethylethylenediaminetriacetate, sodium diethylenetriaminepentaacetate, sodium uracil diacetate and the like.
  • anti-rust examples include acidic sulfite, sodium thiosulfate, ammonium thioglycolate, diisopropylammonium nitrite, pentaerythritol tetranitrate, dicyclohexylammonium nitrite, and the like.
  • Water-soluble UV absorber examples include sulfonated benzophenone compounds, benzotriazole compounds, salicylic acid compounds, cinnamic acid compounds, and triazine compounds.
  • Water-soluble polymer compound examples include polyvinyl alcohol, cellulose derivatives, polyamines and polyimines.
  • antioxidant for example, various organic and metal complex antifading agents can be used.
  • organic anti-fading agent include hydroquinones, alkoxyphenols, dialkoxyphenols, phenols, anilines, amines, indanes, chromans, alkoxyanilines, heterocycles, and the like.
  • surfactant examples include known surfactants such as anionic, cationic, nonionic, silicone surfactant, and fluorine surfactant.
  • Anionic surfactants include alkyl sulfonates, alkyl carboxylates, ⁇ -olefin sulfonates, polyoxyethylene alkyl ether acetates, N-acyl amino acids and their salts, N-acyl methyl taurates, alkyl sulfates Polyoxyalkyl ether sulfate, alkyl sulfate polyoxyethylene alkyl ether phosphate, rosin acid soap, castor oil sulfate ester, lauryl alcohol sulfate ester, alkylphenol type phosphate ester, alkyl type phosphate ester, alkylaryl sulfonate, Examples thereof include diethylsulfosuccinate, diethylhexylsylsulfosuccinate, and dio
  • an anionic surfactant is particularly preferable, and specifically, diethylsulfosuccinate, diethylhexylsylsulfosuccinate, dioctylsulfosuccinate, and the like.
  • Examples of the cationic surfactant include 2-vinylpyridine derivatives and poly-4-vinylpyridine derivatives.
  • Amphoteric surfactants include lauryldimethylaminoacetic acid betaine, 2-alkyl-N-carboxymethyl-N-hydroxyethylimidazolinium betaine, coconut oil fatty acid amidopropyldimethylaminoacetic acid betaine, polyoctylpolyaminoethylglycine, imidazoline derivatives, etc. Is mentioned.
  • Nonionic surfactants include ethers such as polyoxyethylene nonylphenyl ether, polyoxyethylene octylphenyl ether, polyoxyethylene dodecylphenyl ether, polyoxyethylene oleyl ether, polyoxyethylene lauryl ether, polyoxyethylene alkyl ether; Ester systems such as polyoxyethylene oleate, polyoxyethylene distearate, sorbitan laurate, sorbitan monostearate, sorbitan monooleate, sorbitan sesquioleate, polyoxyethylene monooleate, polyoxyethylene stearate; 2,4,7,9-tetramethyl-5-decyne-4,7-diol, 3,6-dimethyl-4-octyne-3,6-diol, 3,5-di Acetylene glycol (alcohol) type such as til-1-hexyn-3-ol; trade name Surfynol 104, 105, 82, 465,
  • silicone surfactant examples include polyether-modified siloxane and polyether-modified polydimethylsiloxane.
  • Specific examples of commercially available products include BYK-347 (polyether-modified siloxane); BYK-345 and BYK-348 (polyether-modified polydimethylsiloxane), all manufactured by BYK Chemie. .
  • fluorosurfactant examples include perfluoroalkyl sulfonic acid compounds, perfluoroalkyl carboxylic acid compounds, perfluoroalkyl phosphate compounds, perfluoroalkyl ethylene oxide adducts, and perfluoroalkyl ether groups.
  • examples include polyoxyalkylene ether polymer compounds having a chain.
  • Specific examples of commercially available products include, for example, Zonyl TBS, FSP, FSA, FSN-100, FSN, FSO-100, FSO, FS-300, Capstone FS-30, FS-31 (manufactured by DuPont); PF-151N, PF-154N (Omnova); The above ink preparation agents are used alone or in combination.
  • the ink emulsion liquid of the present invention has a diameter of the inscribed circle of 5 nm or more and less than 300 nm, and the concentric circumscribed circle. It is preferable that the emulsion composition contains a majority of particles having a roundness defined by the difference between the inscribed circle radius and the inscribed circle radius of 20 nm or less.
  • the ink emulsion composition of the present invention is extremely excellent in storage stability. Therefore, excellent discharge stability can be realized by using a water-based ink, particularly an inkjet water-based ink.
  • a water-based ink the dye and / or pigment is preferably contained in the water-based ink in a range of 0.3 to 10% by mass as a pure color material.
  • the above preservatives, antifungal agents, pH adjusters, chelating reagents, rust preventives, water-soluble UV absorbers, water-soluble polymer compounds, dye-dissolving agents, antioxidants, surfactants, and the like are added to form aqueous Ink may be used.
  • the pH of the aqueous ink of the present invention is preferably pH 5 to 11 and more preferably pH 7 to 10 for the purpose of improving storage stability.
  • the pH and surface tension of the ink composition of the present invention can be appropriately adjusted with a pH adjusting agent and a surfactant as described later.
  • the water-based ink of the present invention may further contain (F) a compound represented by the above formula (4).
  • s is an average degree of polymerization and represents 1 to 5. This average degree of polymerization is described as a numerical value rounded off to the first decimal place.
  • Specific examples of the compound represented by the formula (4) include compounds such as glycerin, diglycerin, triglycerin, tetraglycerin, pentaglycerin, hexaglycerin, heptaglycerin, and mixtures thereof.
  • the degree of polymerization of hexaglycerin and heptaglycerin is 6 and 7, respectively.
  • the average degree of polymerization of the mixture is in the above range.
  • the aqueous ink of the present invention may contain the mixture.
  • the mixture is 50% glycerin and 50% triglycerin
  • the average degree of polymerization s is 2, but if the content of glycerin is large, smoke or the like is generated during sublimation transfer, and work in transfer dyeing Problems such as deterioration of the visual field of the environment occur.
  • the content of glycerin in the compound represented by the formula (4) is usually 10% or less, preferably 8% or less on the basis of gas chromatographic method standard (peak area ratio).
  • the detection limit that is, 0%.
  • the content of the component (F) is preferably in the range of 5 to 60% by mass, and more preferably in the range of 10 to 40% by mass. When the content of the component (F) in the water-based ink is within the above range, the storage stability of the ink is excellent, and the generation of smoke during sublimation transfer is small.
  • the water-based ink of the present invention can be used in various fields, but is suitable for water-based ink for writing, water-based printing ink, information recording ink, textile printing, etc., and particularly preferably used as ink for ink-jet recording.
  • the mixture was filtered with glass fiber filter paper GC-50 (manufactured by Toyo Roshi Kaisha, Ltd., filter pore size 0.5 ⁇ m) to obtain Joncryl 690 emulsion 3 from which components having a large particle size were removed.
  • GC-50 manufactured by Toyo Roshi Kaisha, Ltd., filter pore size 0.5 ⁇ m
  • Examples 1 to 26, Comparative Examples 1 to 6 Preparation of Ink Dispersion Composition 0.2 mm diameter glass beads were added to the mixture of each component described in Tables 1 to 6 below, and the mixture was cooled with a sand mill under water cooling. The dispersion process was performed for 15 hours. Ion exchange water was added to the obtained liquid to prepare a dye content of 15% in the total mass of the liquid. The obtained liquid was filtered through glass fiber filter paper GC-50 (manufactured by ADVANTEC) to obtain ink dispersion compositions of Examples and Comparative Examples.
  • GC-50 manufactured by ADVANTEC
  • the core layer is a dye and the shell layer is a styrene- (meth) acrylic copolymer. While the core-shell colorant was confirmed, the core-shell colorant was not confirmed in the comparative ink dispersion composition.
  • Diglycerin S a compound represented by the formula (4), in which s is 2, manufactured by Sakamoto Pharmaceutical Co., Ltd., glycerin content 0.5%
  • Surfynol 420 Surfactant, manufactured by Nissin Chemical Industry Co., Ltd.
  • the ink emulsion composition and water-based ink composition of the present invention have high storage stability, and are particularly useful as a water-based ink for inkjet.

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)

Abstract

La présente invention concerne une composition d'émulsion d'encre qui a une bonne stabilité au stockage, qui fournit une concentration élevée de colorant et a une bonne redispersibilité après séchage, même lorsqu'elle est utilisée comme composition d'encre, et, en outre, qui n'entraîne pas de changements des propriétés physiques de l'encre lors d'un stockage à long terme. La composition d'émulsion d'encre est une émulsion liquide (A) contenant un colorant ayant une structure cœur-enveloppe, la couche de cœur du composant (A) étant un colorant et/ou un pigment, et la couche d'enveloppe étant un copolymère styrène-(méth)acrylique.
PCT/JP2016/004737 2015-10-30 2016-10-28 Composition d'émulsion d'encre et encre aqueuse WO2017073068A1 (fr)

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CN107629551A (zh) * 2017-10-25 2018-01-26 杭州海维特化工科技有限公司 一种纺织品用微胶囊包覆型颜料喷绘水墨及其制备方法
WO2019054215A1 (fr) * 2017-09-13 2019-03-21 日本化薬株式会社 Composition de dispersion pour encre et encre à base d'eau
JP2019065076A (ja) * 2017-09-28 2019-04-25 セイコーエプソン株式会社 インクセット及び記録方法
JP2020537026A (ja) * 2017-10-17 2020-12-17 ファルベンプンクト，アイエヌシー 分散したナノ色素ミセルを含むインク及びそれから得られる印刷織物
WO2021002851A1 (fr) * 2019-07-02 2021-01-07 Hewlett-Packard Development Company, L.P. Encres comprenant une résine dans une phase dispersée
JPWO2021075272A1 (ja) * 2019-10-17 2021-11-25 Dic株式会社 インク

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JP2005298802A (ja) * 2003-12-03 2005-10-27 Sakura Color Prod Corp 水性顔料インキ組成物
JP2008255241A (ja) * 2007-04-05 2008-10-23 Ricoh Co Ltd 記録用インク組成物、インクジェット記録方法、記録物、記録液カートリッジ、インクジェット記録装置および記録インク組成物の製造方法
JP2011021133A (ja) * 2009-07-17 2011-02-03 Nippon Kayaku Co Ltd 昇華転写用インクジェットインク、それを用いる染色方法及び染色物
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Publication number Priority date Publication date Assignee Title
WO2019054215A1 (fr) * 2017-09-13 2019-03-21 日本化薬株式会社 Composition de dispersion pour encre et encre à base d'eau
JPWO2019054215A1 (ja) * 2017-09-13 2020-08-27 日本化薬株式会社 インク用分散液組成物及び水性インク
EP3683279A4 (fr) * 2017-09-13 2021-06-09 Nippon Kayaku Kabushiki Kaisha Composition de dispersion pour encre et encre à base d'eau
JP2019065076A (ja) * 2017-09-28 2019-04-25 セイコーエプソン株式会社 インクセット及び記録方法
JP7017052B2 (ja) 2017-09-28 2022-02-08 セイコーエプソン株式会社 インクセット及び記録方法
JP2020537026A (ja) * 2017-10-17 2020-12-17 ファルベンプンクト，アイエヌシー 分散したナノ色素ミセルを含むインク及びそれから得られる印刷織物
JP7138704B2 (ja) 2017-10-17 2022-09-16 ファルベンプンクト，アイエヌシー 分散したナノ色素ミセルを含むインク及びそれから得られる印刷織物
CN107629551A (zh) * 2017-10-25 2018-01-26 杭州海维特化工科技有限公司 一种纺织品用微胶囊包覆型颜料喷绘水墨及其制备方法
WO2021002851A1 (fr) * 2019-07-02 2021-01-07 Hewlett-Packard Development Company, L.P. Encres comprenant une résine dans une phase dispersée
JPWO2021075272A1 (ja) * 2019-10-17 2021-11-25 Dic株式会社 インク

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