WO2022224945A1 - Dispersion colorée - Google Patents

Dispersion colorée Download PDF

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Publication number
WO2022224945A1
WO2022224945A1 PCT/JP2022/018121 JP2022018121W WO2022224945A1 WO 2022224945 A1 WO2022224945 A1 WO 2022224945A1 JP 2022018121 W JP2022018121 W JP 2022018121W WO 2022224945 A1 WO2022224945 A1 WO 2022224945A1
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Prior art keywords
compound represented
examples
water
colored dispersion
manufactured
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PCT/JP2022/018121
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English (en)
Japanese (ja)
Inventor
秋津 花里
由昌 宮沢
悠太 萩原
理生 桐田
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日本化薬株式会社
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Priority to JP2023515467A priority Critical patent/JPWO2022224945A1/ja
Publication of WO2022224945A1 publication Critical patent/WO2022224945A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • 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
    • C09B1/16—Amino-anthraquinones
    • C09B1/20—Preparation from starting materials already containing the anthracene nucleus
    • C09B1/22—Dyes with unsubstituted amino groups
    • 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
    • C09B67/0084—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
    • C09D11/30—Inkjet printing 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
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D17/00—Pigment pastes, e.g. for mixing in paints
    • 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
    • D06P5/30—Ink jet printing

Definitions

  • the present invention relates to a colored dispersion.
  • hydrophobic fibers typified by polyester fibers are generally dyed with a water-insoluble colorant.
  • a water-insoluble colorant is dispersed in water and which has good performance such as dispersion stability.
  • the inkjet textile printing method for hydrophobic fibers is roughly divided into the direct printing method and the sublimation transfer method.
  • the direct printing method is a textile printing method in which ink is directly applied (printed) to hydrophobic fibers, and then the hydrophobic fibers are dyed with the dye in the ink by heat treatment such as high-temperature steaming.
  • the sublimation transfer method ink is applied (printed) to an intermediate recording medium (dedicated transfer paper, etc.), then the ink-applied surface of the intermediate recording medium and hydrophobic fibers are superimposed, and then the dye is transferred to the intermediate by heat. It is a printing method that transfers from a recording medium to a hydrophobic fiber.
  • the sublimation transfer method is mainly used for printing banners, etc., and easily sublimation dyes are used in the ink, which are excellent in transferability to hydrophobic fibers by heat treatment.
  • the processing steps include (1) printing step: applying dye ink to the intermediate recording medium by an inkjet printer, (2) transfer step: transferring and dyeing the dye from the intermediate recording medium to the fibers by heat treatment. It involves two steps, does not require fiber pretreatment due to the wide range of commercially available transfer papers, and omits the washing step.
  • a water-based ink in which a water-insoluble dye is dispersed in water is generally used.
  • a water-soluble organic solvent as a moisturizing agent antioxidant
  • a dye dispersion liquid in which a water-insoluble dye selected from disperse dyes and oil-soluble dyes is dispersed in water with a dispersant.
  • Surfactant as a surface tension adjuster, and other additives are added, and physical properties such as particle size, viscosity, surface tension, pH (physical properties) to prepare aqueous inks.
  • An object of the present invention is to provide a colored dispersion that is excellent in storage stability and filterability after storage.
  • Specific means for solving the above problems include the following embodiments. 1) Containing a coloring agent containing a compound represented by the following formula (1) and a compound represented by the following formula (2), and water, When the coloring agent is analyzed by high performance liquid chromatography (HPLC), the peak area (A) of the compound represented by the following formula (1) and the peak area (B) of the compound represented by the following formula (2) ) satisfies the relationship of ((A)/(B)) ⁇ 0.028.
  • HPLC high performance liquid chromatography
  • C.I is an abbreviation for color index.
  • the colored dispersion liquid according to the present embodiment contains a colorant containing a specific compound represented by formula (1) and a specific compound represented by formula (2), and water.
  • a colorant containing a specific compound represented by formula (1) and a specific compound represented by formula (2) and water.
  • Components contained in the colored dispersion according to the present embodiment will be described in detail below.
  • each component demonstrated below may be used individually by 1 type of them, and may use 2 or more types together.
  • Colorants include compounds represented by the following formula (1) and compounds represented by the following formula (2).
  • the peak area (A) of the compound represented by the above formula (1) and the above formula (2) satisfies the relationship of ((A)/(B)) ⁇ 0.028.
  • the content ratio of the compound represented by the above formula (1) to the compound represented by the above formula (2) satisfies the relationship of ((A) / (B)) ⁇ 0.028, so that the colored dispersion can be obtained. Storage stability and filterability after storage tend to be good.
  • the content ratio of the compound represented by the above formula (1) to the compound represented by the above formula (2) preferably satisfies the relationship of ((A) / (B)) ⁇ 0.027, (( It is more preferable to satisfy the relationship of A)/(B)) ⁇ 0.024, more preferably to satisfy the relationship of 0.001 ⁇ ((A)/(B)) ⁇ 0.024, and 0.004 ⁇ It is particularly preferable to satisfy the relationship ((A)/(B)) ⁇ 0.020, and it is very preferable to satisfy the relationship 0.006 ⁇ ((A)/(B)) ⁇ 0.014.
  • the method for obtaining a colorant in which the content ratio of the compound represented by the above formula (1) and the compound represented by the above formula (2) satisfies the above relationship is not particularly limited. and the compound represented by the above formula (2) can be blended so as to satisfy the above relationship.
  • a compound containing the compound represented by the above formula (1) and the compound represented by the above formula (2) may be purified by a known purification method to adjust the content ratio.
  • the purification method is not particularly limited, and conventional means such as solid-liquid extraction, liquid-liquid extraction, reflux extraction, Soxhlet extraction, immersion, and stirring can be used. These means may be used singly or in combination of two or more. For example, solid-liquid extraction and liquid-liquid extraction may be combined. When combining two or more means, the order between the means can be arbitrarily set according to the purpose such as extraction efficiency.
  • an organic solvent can be used as an extraction solvent.
  • the organic solvent may be a hydrophilic organic solvent or a hydrophobic organic solvent.
  • extraction solvents include monohydric, dihydric, or polyhydric alcohols and aqueous solutions thereof; ketones such as acetone and methyl ethyl ketone; esters such as methyl acetate and ethyl acetate; chain ethers such as diethyl ether; Saturated or unsaturated hydrocarbons such as pentane and hexane; aromatic hydrocarbons such as benzene and toluene; halogenated hydrocarbons such as dichloromethane, chloroform, dichloroethane and carbon tetrachloride; carbon dioxide and supercritical carbon dioxide; edible oils such as rapeseed oil and soybean oil; oils and fats such as diacylglycerol (DAG), medium chain fatty acid oil, squalane and squalene;
  • DAG diacylgly
  • the conditions for solid-liquid extraction are not particularly limited as long as they allow sufficient extraction.
  • the amount of extraction solvent used is preferably 1 to 100 mL per 1 g of the formulation.
  • the extraction time is usually long if the solvent is cold, but may be short if the solvent is hot. Moreover, you may perform extraction operation twice or more.
  • Preferred extraction conditions include, for example, conditions in which extraction is performed twice at 10 to 50° C. for 1 to 2 hours.
  • the method for separating solids in solid-liquid extraction is not particularly limited, and can be separated and recovered, for example, by filtration using a Buchner funnel and filter paper. At that time, by adding an extraction solvent onto the cake in the Buchner funnel, the purification effect can be further enhanced.
  • an operation to remove the solvent may be added.
  • Examples of the method for removing the solvent include an operation of removing the solvent under reduced pressure; an operation of suspending the cake in water and filtering; an operation of adding water to the cake and filtering;
  • the content of the compound represented by the above formula (2) is 0.00% with respect to the total amount of the colored dispersion, from the viewpoint of securing the degree of freedom of composition during preparation of the colored dispersion and the stability of the colored dispersion. It is preferably 1 to 30% by mass, more preferably 0.5 to 25% by mass, even more preferably 1 to 20% by mass.
  • water water containing few impurities such as ion-exchanged water, distilled water, and ultrapure water is preferable.
  • the water content is appropriately selected depending on the application.
  • the content of water is usually 200 to 8500 parts by weight per 100 parts by weight of the colorant.
  • the colored dispersion liquid according to the present embodiment preferably further contains a dispersant.
  • Dispersants include, but are not limited to, styrene-(meth)acrylic copolymers, formalin condensates of aromatic sulfonic acids or salts thereof, polyoxyethylene aryl phenyl ethers, polyoxyethylene aryl phenyl ether sulfates, and polyoxy It preferably contains at least one selected from the group consisting of ethylene naphthyl ether.
  • a 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, ( ⁇ -methyl)styrene-methacrylic acid copolymer.
  • the weight average molecular weight of the styrene-(meth)acrylic copolymer is, for example, preferably 1,000 to 20,000, more preferably 2,000 to 19,000, even more preferably 5,000 to 17,000.
  • the weight average molecular weight of the styrene-(meth)acrylic copolymer can be measured by a GPC (gel permeation chromatography) 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, even more preferably 150 to 250 mgKOH/g. .
  • the acid value of a resin represents the number of mg of KOH required to neutralize 1 g of 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, even more preferably 60 to 110°C.
  • Examples of commercially available styrene-(meth)acrylic copolymers include Joncryl 67, 678, 680, 682, 683, 690, 52J, 57J, 60J, 63J, 70J, JDX-6180, HPD-196, HPD96J, PDX-6137A, 6610, JDX-6500, JDX-6639, PDX-6102B, PDX-6124 (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) 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 preferred.
  • formalin condensates of aromatic sulfonic acids or salts thereof include creosote oil sulfonic acid, cresol sulfonic acid, phenolsulfonic acid, ⁇ -naphthalenesulfonic acid, ⁇ -naphtholsulfonic acid, ⁇ -naphthalenesulfonic acid, and benzenesulfonic acid. Acids, cresolsulfonic acid, 2-naphthol-6-sulfonic acid, formalin condensates such as ligninsulfonic acid, and salts thereof (sodium salt, potassium salt, lithium salt, etc.).
  • formalin condensates of creosote oil sulfonic acid, ⁇ -naphthalene sulfonic acid, lignin sulfonic acid and methylnaphthalene sulfonic acid, and salts thereof are preferred.
  • a formalin condensate of aromatic sulfonic acid is also available as a commercial product.
  • the formalin condensate of ⁇ -naphthalenesulfonic acid includes Demol N (manufactured by Kao Corporation).
  • Examples of the formalin condensate of creosote oil sulfonic acid include Demol C (manufactured by Kao Corporation) and Labelin W series (manufactured by Daiichi Kogyo Seiyaku Co., Ltd.).
  • Examples of formalin condensates of special aromatic sulfonic acids include Demol SN-B (manufactured by Kao Corporation).
  • Examples of the formalin condensate of methylnaphthalenesulfonic acid include Labelin AN series (manufactured by Dai-ichi Kogyo Seiyaku Co., Ltd.). Among these, Demoll N, Labellin AN series, and Labellin W series are preferred, Demoll N and Labellin W series are more preferred, and Labellin W series is even more preferred.
  • Examples of ligninsulfonic acid include Vanilex N, Vanilex RN, Vanilex G, and Pearllex DP (manufactured by Nippon Paper Industries Co., Ltd.). Among these, Vanilex RN, Vanilex N, and Vanilex G are preferred.
  • polyoxyethylene arylphenyl ethers examples include styrylphenol compounds such as polyoxyethylene monostyrylphenyl ether, polyoxyethylene distyrylphenyl ether, polyoxyethylene tristyrylphenyl ether, and polyoxyethylene tetrastyrylphenyl ether; benzylphenol compounds such as ethylene monobenzylphenyl ether, polyoxyethylene dibenzylphenyl ether, polyoxyethylene tribenzylphenyl ether; cumylphenol compounds such as polyoxyethylene cumylphenyl ether; polyoxyethylene naphthylphenyl ether, polyoxy ethylene biphenyl ether, polyoxyethylene phenoxyphenyl ether; and the like.
  • styrylphenol compounds such as polyoxyethylene monostyrylphenyl ether, polyoxyethylene distyrylphenyl ether, polyoxyethylene tristyrylphenyl ether, and polyoxyethylene tetrastyrylphenyl
  • polyoxyethylene distyryl phenyl ether polyoxyethylene tristyryl phenyl ether, polyoxyethylene dibenzyl phenyl ether, polyoxyethylene tribenzyl phenyl ether, and polyoxyethylene cumyl phenyl ether are preferred.
  • the number of repeating polyoxyethylene groups in the polyoxyethylene arylphenyl ether is preferably 1-30, more preferably 15-30.
  • the compatibility with aqueous solvents and the like tends to be excellent.
  • the number of repetitions is 30 or less, the viscosity tends not to become too high.
  • polyoxyethylene arylphenyl ethers include, for example, Noigen EA series (manufactured by Daiichi Kogyo Seiyaku Co., Ltd.); 6512, Takesurf D-6413, DTD-51, Pionin D-6112, Pionin D-6320 (manufactured by Takemoto Oil Co., Ltd.); TS-1500, TS-2000, TS-2600, SM-174N (toho chemical Emulgen A60, Emulgen A90, Emulgen A500 (manufactured by Kao Corporation); Emulgen B-66, Newcol CMP (manufactured by Nippon Emulsifier Co., Ltd.);
  • polyoxyethylene aryl phenyl ether sulfates examples include sulfates of the above-mentioned polyoxyethylene aryl phenyl ethers.
  • polyoxyethylene arylphenyl ether sulfates include, for example, SM-57, SM-130, SM-210 (manufactured by Toho Chemical Co., Ltd.).
  • polyoxyethylene naphthyl ether examples include, for example, Noigen EN series (manufactured by Daiichi Kogyo Seiyaku Co., Ltd.) and Pionin D-7240 (manufactured by Takemoto Yushi Co., Ltd.).
  • anionic dispersants such as aromatic sulfonic acid formalin condensates or salts thereof are preferred, sodium naphthalenesulfonate formalin condensates are more preferred, and creosote oil sulfonic acid formalin condensates are even more preferred.
  • the colored dispersion according to the present embodiment may further contain a conventionally known nonionic dispersant.
  • Nonionic dispersants include, for example, alkylene oxide adducts of phytosterols, alkylene oxide adducts of cholestanols, polyoxyethylene alkyl ethers, polyoxyethylene alkylphenyl ethers, polyoxyethylene fatty acid esters, sorbitan fatty acid esters, polyoxy Examples include ethylene sorbitan fatty acid esters, polyoxyethylene alkylamines, glycerin fatty acid esters, oxyethyleneoxypropylene block polymers, and substituted derivatives thereof.
  • alkylene oxide adducts of phytosterols also referred to as phytosterol compounds
  • alkylene oxide adducts of cholestanols also referred to as cholestanol compounds
  • phytosterol compounds are more preferred.
  • the alkylene oxide adduct of phytosterols is preferably a C2-C4 alkylene oxide adduct of phytosterols, more preferably an ethylene oxide adduct.
  • the term "phytosterols” includes both "phytosterols” and "hydrogenated phytosterols.”
  • ethylene oxide adducts of phytosterols include ethylene oxide adducts of phytosterols and ethylene oxide adducts of hydrogenated phytosterols.
  • the alkylene oxide adducts of cholestanols are preferably C2-C4 alkylene oxide adducts of cholestanols, more preferably ethylene oxide adducts.
  • cholestanols includes both “cholestanol” and “hydrogenated cholestanol”.
  • ethylene oxide adducts of cholestanols include ethylene oxide adducts of cholestanol and ethylene oxide adducts of hydrogenated cholestanol.
  • the added amount of alkylene oxide (preferably C2-C4 alkylene oxide, more preferably ethylene oxide) per 1 mol of phytosterols or cholestanols is preferably about 10 to 50 mol, and HLB is preferably about 13 to 20.
  • Examples of commercially available alkylene oxide adducts of phytosterols include NIKKOL BPS-20 and NIKKOL BPS-30 (both manufactured by Nikko Chemicals Co., Ltd., ethylene oxide adducts of phytosterols), NIKKOL BPSH-25 (same, hydrogenated phytosterol ethylene oxide adduct) and the like.
  • Examples of commercially available alkylene oxide adducts of cholestanols include NIKKOL DHC-30 (ethylene oxide adduct of cholestanol, manufactured by Nikko Chemicals Co., Ltd.).
  • the content is preferably 1 to 300 parts by mass, and 5 to 120 parts by mass, for 100 parts by mass of the colorant. is more preferable.
  • the colored dispersion according to the present embodiment may contain additives other than those described above.
  • Additives include, for example, water-soluble organic solvents, preservatives, surfactants, pH adjusters, chelating reagents, rust inhibitors, water-soluble ultraviolet absorbers, water-soluble polymer compounds, viscosity adjusters, pigment solubilizers, Examples include antioxidants, resin emulsions, and the like.
  • the colored dispersion according to the present embodiment preferably contains at least one selected from the group consisting of water-soluble organic solvents, preservatives, surfactants, and pH adjusters.
  • the content of the water-soluble organic solvent is preferably 0 to 90% by mass, more preferably 0.01 to 85% by mass, relative to the total amount of the colored dispersion. Also, the total content of other additives is preferably 0 to 50% by mass, more preferably 0.01 to 10% by mass, relative to the total amount of the colored dispersion.
  • Examples of water-soluble organic solvents include glycol-based solvents, polyhydric alcohols, and pyrrolidones.
  • glycol-based solvents include glycerin, polyglycerin (#310, #750, #800), diglycerin, triglycerin, tetraglycerin, pentaglycerin, hexaglycerin, heptaglycerin, octaglycerin, nonaglycerin, decaglycerin, undecaglycerin, dodecaglycerin, tridecaglycerin, tetradecaglycerin and the like.
  • Polyhydric alcohols include, for example, C2-C6 polyhydric alcohols 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 can be mentioned.
  • Specific examples thereof include ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol, polyethylene glycol, polypropylene glycol, 1,3-propanediol, 1,2-butanediol, thiodiglycol, 1,3-butanediol, 1,4-butanediol, 2,3-butanediol, 3-methyl-1,3-butanediol, 1,2-pentanediol, 1,5-pentanediol, 2-methyl-2,4-pentanediol, 3-methyl-1,5-pentanediol, 1,2-hexanediol, 1,6-hexanediol, glycerin, trimethylolpropane, 1,3-pentanediol, 1,5-pentanediol and the like.
  • pyrrolidones examples include 2-pyrrolidone, N-methyl-2-pyrrolidone and the like.
  • water-soluble organic solvents also include compounds that dissolve in water and act as wetting agents. Such compounds include, for example, urea, ethylene urea, sugars and the like.
  • the water-soluble organic solvent (B) is preferably a solvent in which the water-insoluble dye has a low solubility.
  • polyhydric alcohol is preferably used in combination.
  • antiseptics examples include organic sulfur, organic nitrogen sulfur, organic halogen, haloallyl sulfone, iodopropargyl, N-haloalkylthio, nitrile, pyridine, 8-oxyquinoline, and benzothiazole. type, isothiazoline type, dithiol type, pyridine oxide type, nitropropane type, organic tin type, phenol type, quaternary ammonium salt type, triazine type, thiazine type, anilide type, adamantane type, dithiocarbamate type, brominated indanone type, Compounds such as benzyl bromoacetate-based compounds and inorganic salt-based compounds are included.
  • organic halogen compounds include sodium pentachlorophenol.
  • pyridine oxide compounds include sodium 2-pyridinethiol-1-oxide.
  • isothiazolin compounds include 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, etc. is mentioned.
  • Specific examples of other antiseptic and antifungal agents include anhydrous sodium acetate, sodium sorbate, sodium benzoate, trade names Proxel GXL (S) and Proxel XL-2 (S) manufactured by Lonza.
  • surfactants include known surfactants such as anionic, cationic, amphoteric, nonionic, silicone, and fluorine-based surfactants.
  • 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 Sulfate polyoxyalkyl ether sulfate, alkyl sulfate polyoxyethylene alkyl ether phosphate, rosin acid soap, castor oil sulfate, lauryl alcohol sulfate, alkylphenol type phosphate, alkyl type phosphate, alkyl arylsulfonates, diethylsulfosuccinates, diethylhexylsulfosuccinates, dioctylsulfosuccinates and the like.
  • Commercially available products include, for example, Hitenol LA-10, LA-12, LA-16, Neohitenol ECL-30S and ECL-45, all
  • cationic surfactants examples include 2-vinylpyridine derivatives and poly-4-vinylpyridine derivatives.
  • amphoteric surfactants include betaine lauryldimethylaminoacetate, 2-alkyl-N-carboxymethyl-N-hydroxyethylimidazolinium betaine, betaine coconut fatty acid amidopropyldimethylaminoacetate, polyoctylpolyaminoethylglycine, and imidazoline. derivatives and the like.
  • nonionic surfactants 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 oleate, polyoxyethylene distearate, sorbitan laurate, sorbitan monostearate, sorbitan monooleate, sorbitan sesquioleate, polyoxyethylene monooleate, polyoxyethylene stearate system; 2,4,7,9-tetramethyl-5-decyne-4,7-diol, 3,6-dimethyl-4-octyne-3,6-diol, 3,5-dimethyl-1-hexyne-3 -Acetylene glycol (alcohol)-based such as all; Surfynol 104, 105, 82, 465 manufactured by Air Products Japan Co., Ltd., Olphine STG, etc.; Polyglycol ether-based (for example, Tergitol 15-S- manufactured by SIGMA-ALDRICH) 7 etc.);
  • silicone-based surfactants include polyether-modified siloxane and polyether-modified polydimethylsiloxane.
  • examples of commercially available products include BYK-347 (polyether-modified siloxane); BYK-345 and BYK-348 (polyether-modified polydimethylsiloxane), all of which are manufactured by BYK-Chemie.
  • fluorine-based surfactants include perfluoroalkylsulfonic acid compounds, perfluoroalkylcarboxylic acid compounds, perfluoroalkylphosphoric acid ester compounds, perfluoroalkylethylene oxide adducts, and perfluoroalkyl ether groups in side chains.
  • polyoxyalkylene ether polymer compounds having 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 (manufactured by Omnova); and the like.
  • any substance can be used as the pH adjuster as long as it can control the pH of the colored dispersion in the range of 5.0 to 11.0 without adversely affecting the prepared colored dispersion.
  • Specific examples thereof include 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 reagents include, for example, sodium ethylenediaminetetraacetate, sodium nitrilotriacetate, sodium hydroxyethylethylenediaminetriacetate, sodium diethylenetriaminepentaacetate, and sodium uracil diacetate.
  • rust preventives include acidic sulfites, sodium thiosulfate, ammonium thioglycolate, diisopropylammonium nitrite, pentaerythritol tetranitrate, and dicyclohexylammonium nitrite.
  • water-soluble UV absorbers examples include sulfonated benzophenone-based compounds, benzotriazole-based compounds, salicylic acid-based compounds, cinnamic acid-based compounds, and triazine-based compounds.
  • water-soluble polymer compounds examples include polyvinyl alcohol, cellulose derivatives, polyamines, and polyimines.
  • Viscosity modifiers include, in addition to water-soluble organic solvents, water-soluble polymer compounds such as polyvinyl alcohol, cellulose derivatives, polyamines, and polyimines.
  • pigment-dissolving agents examples include urea, ⁇ -caprolactam, and ethylene carbonate.
  • organic anti-fading agents include hydroquinones, alkoxyphenols, dialkoxyphenols, phenols, anilines, amines, indanes, chromans, alkoxyanilines, and heterocycles.
  • metal complex-based anti-fading agents include nickel complexes and zinc complexes.
  • resin emulsions examples include acrylic resins, epoxy resins, urethane resins, polyether resins, polyamide resins, unsaturated polyester resins, phenol resins, silicone resins, fluorine resins, polyvinyl resins (vinyl chloride, vinyl acetate, polyvinyl alcohol, etc.). , alkyd resins, polyester resins, amino materials (melanin resins, urea resins, urea resins, melanin-formaldehyde resins, etc.) and the like.
  • the resin emulsion may contain two or more resins. Also, two or more resins may form a core/shell structure. Among resin emulsions, urethane resin emulsions are preferred.
  • Urethane resin emulsions are commercially available, and most of them are emulsions with a solid concentration of 30 to 60% by mass.
  • Commercially available urethane resin emulsions include, for example, Permalin UA-150, 200, 310, 368, 3945, Yukote UX-320 (manufactured by Sanyo Kasei Co., Ltd.); Hydran WLS-201, 210, HW-312B latex.
  • polycarbonate-based urethane resins examples include Permaline UA-310, 3945; Ukote UX-320; and the like.
  • polyether-based urethane resins examples include Permalin UA-150 and 200; Ukote 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 . More preferably, it is up to 11 (cal/cm 3 ) 1/2 .
  • the SP value of urethane resin is calculated by the Fedors method. When the urethane resin has an acidic group and the emulsion is prepared by neutralizing the acidic group, the SP value of the urethane resin before neutralization is used.
  • the acidic group may be alkali chlorided.
  • 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, whereby the acidic group is alkali chlorided. can do.
  • alkaline compounds include hydroxides of alkali metals such as lithium hydroxide, sodium hydroxide and potassium hydroxide; water of alkaline earth metals such as beryllium hydroxide, magnesium hydroxide, calcium hydroxide and strontium hydroxide. oxide; and the like. Alkaline compounds may be used alone or in combination of two or more.
  • Method for preparing colored dispersion for example, an aqueous dispersion containing a coloring agent, a dispersant, and water is prepared, and if necessary, an additive such as a water-soluble organic solvent is further added. method.
  • 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 aqueous dispersion.
  • a sand mill a sand mill
  • a roll mill a ball mill
  • a paint shaker an ultrasonic disperser
  • a high-pressure emulsifier a high-pressure emulsifier, or the like
  • the beads glass beads, zirconia beads, etc. having a particle size of 0.01 to 1 mm can be used.
  • the amount of beads to be used is preferably 2 to 6 parts by mass per 1 part by mass of the object to be dispersed.
  • Dispersion treatment conditions are preferably about 1000 to 2000 rpm for 1 to 20 hours.
  • the beads are removed by filtration or the like to obtain an aqueous dispersion.
  • the prepared colored dispersion may be subjected to precision filtration using a membrane filter or the like.
  • a membrane filter or the like In particular, when the colored dispersion is used as ink for inkjet textile printing, it is preferable to carry out microfiltration for the purpose of preventing clogging of nozzles.
  • the pore size of the filter used for microfiltration is usually 0.1-1 ⁇ m, preferably 0.1-0.8 ⁇ m.
  • the viscosity at 25° C. of the colored dispersion according to the present embodiment is preferably about 1 to 20 mPa ⁇ s when measured with an E-type viscometer in terms of high-speed ejection responsiveness.
  • the surface tension of the colored dispersion according to the present embodiment at 25° C. is preferably about 20 to 55 mN/m when measured by a plate method.
  • the physical properties are adjusted to appropriate values in consideration of the ejection volume, response speed, ink droplet flight characteristics, etc. of the ink jet printer to be used.
  • the colored dispersion according to the present embodiment can be used in various fields, and is suitable for water-based writing ink, water-based printing ink, information recording ink, textile printing, and the like. It is particularly preferable to use the colored dispersion liquid according to the present embodiment as an ink for inkjet textile printing.
  • the colored dispersion according to the present embodiment deterioration of filterability of the colored dispersion during storage can be effectively suppressed. That is, according to the colored dispersion according to the present embodiment, the dispersed state of the particles in the colored dispersion can be stably maintained.
  • the colored dispersion liquid according to the present embodiment has good initial filling properties into an inkjet printer head, and also has good continuous printing stability. Further, it is possible to obtain a clear image without blurring of the image on the paper after printing.
  • the colored dispersion set according to this embodiment includes the colored dispersion according to this embodiment and at least one other colored dispersion different from the colored dispersion.
  • the other colored dispersion preferably has a hue different from that of the colored dispersion according to the present embodiment, and examples thereof include colored dispersions having hues such as yellow, magenta, and cyan.
  • the recording medium according to the present embodiment has the colored dispersion liquid according to the present embodiment or each colored dispersion liquid included in the colored dispersion liquid set according to the present embodiment attached.
  • Examples of recording media include fibers and paper (plain paper, inkjet paper, etc.).
  • the recording medium according to this embodiment is preferably made of hydrophobic fibers.
  • hydrophobic fibers examples include polyester fibers, nylon fibers, triacetate fibers, diacetate fibers, polyamide fibers, and blended fibers using two or more of these fibers.
  • blended fibers of these hydrophobic fibers with regenerated fibers such as rayon, and natural fibers such as cotton, silk and wool are also included in the hydrophobic fibers in this specification.
  • Some of these fibers are known to have an ink-receiving layer (anti-bleeding layer), and such fibers are also included in hydrophobic fibers.
  • the method for forming the ink-receiving layer is a known technique, and fibers having an ink-receiving layer are also commercially available.
  • the material, structure, etc. of the ink-receiving layer are not particularly limited, and can be used appropriately according to the purpose.
  • the method for printing hydrophobic fibers according to the present embodiment is a method of printing hydrophobic fibers using the colored dispersion liquid according to the present embodiment or the colored dispersion liquid set according to the present embodiment.
  • Printing methods for hydrophobic fibers are roughly classified into direct printing methods and sublimation transfer methods.
  • droplets of a colored dispersion are attached to a hydrophobic fiber by an inkjet printer, and a printing process to obtain a recorded image such as letters and patterns, and a coloring attached to the hydrophobic fiber in the printing process. It includes a fixing step of fixing the dye in the dispersion to the hydrophobic fibers by heat, and a washing step of washing the unfixed dye remaining in the hydrophobic fibers.
  • the fixing process is generally performed by known steaming or baking.
  • steaming for example, the hydrophobic fiber is treated with a high temperature steamer at 170 to 180° C. for about 10 minutes, or with a high pressure steamer at 120 to 130° C. for about 20 minutes.
  • a method of dyeing also referred to as wet heat fixation
  • the baking for example, a method of dyeing the hydrophobic fiber with a dye (also called dry heat fixing) by treating the hydrophobic fiber at 190 to 210° C. for about 6 to 120 seconds is available. mentioned.
  • the washing step is a step of washing the obtained fibers with warm water and, if necessary, water.
  • 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.
  • droplets of a colored dispersion are attached to an intermediate recording medium by an inkjet printer, thereby obtaining a recorded image such as characters and patterns. and a transfer step of transferring the recorded image to the hydrophobic fiber by bringing the hydrophobic fiber into contact with and heat-treating.
  • the attached dye in the colored dispersion does not aggregate on its surface 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 paper having an ink-receiving layer formed on the surface thereof with inorganic fine particles such as silica, and special paper for inkjet can be used.
  • the printing method for hydrophobic fibers according to the present embodiment may further include a pretreatment step for the hydrophobic fibers for the purpose of preventing bleeding and the like.
  • the pretreatment step include a step of applying an aqueous solution (pretreatment liquid) containing a sizing agent, an alkaline substance, an anti-reducing agent, and a hydrotropic agent to the hydrophobic fibers before the colored dispersion is adhered. .
  • sizing agents include natural gums such as guar and locust bean; starches; seaweeds such as sodium alginate and funori; plant skins such as pectic acid; processed starch such as carboxymethyl starch; synthetic glue such as polyvinyl alcohol and polyacrylic acid ester; and the like, and sodium alginate is preferred.
  • alkaline substances include alkali metal salts of inorganic acids or organic acids; salts of alkaline earth metals; compounds that release alkali when heated; and the like, and alkali metal hydroxides and alkali metal salts are preferred.
  • alkali metal hydroxides such as sodium hydroxide and calcium hydroxide
  • inorganic compounds such as sodium carbonate, sodium hydrogen carbonate, potassium carbonate, sodium dihydrogen phosphate, disodium hydrogen phosphate and sodium phosphate alkali metal salts of compounds
  • alkali metal salts of organic compounds such as sodium formate and sodium trichloroacetate; and the like, with sodium hydrogen carbonate being preferred.
  • the anti-reduction agent sodium meta-nitrobenzenesulfonate is preferred.
  • the hydrotropic agent includes ureas such as urea and dimethylurea, and urea is preferred.
  • the adhesive, alkaline substance, anti-reducing agent, and hydrotropic agent may be used singly or in combination of two or more.
  • the mixing ratio of each component in the pretreatment liquid is, for example, 0.5 to 5% by mass of paste, 0.5 to 5% by mass of sodium hydrogen carbonate, 0 to 5% by mass of sodium metanitrobenzenesulfonate, and 0 to 5% by mass of urea. is 1 to 20% by mass, and the balance is water.
  • the padding reduction rate is preferably about 40 to 90%, more preferably about 60 to 80%.
  • the content of the compound represented by the above formula (1) (peak area (A) in HPLC analysis) and the content of the compound represented by the above formula (2) (peak area in HPLC analysis ( B)) was measured by the following procedure. First, 20 g of acetonitrile was added to 10 mg of the colorant, and ultrasonic waves were applied for 3 minutes. This mixed solution was filtered through a syringe filter with a pore size of 0.45 ⁇ m (manufactured by ADVANTECH), and then analyzed using an HPLC device. HPLC measurement conditions are as follows.
  • Colorant 1 was a compound containing the compound represented by the above formula (1) and the compound represented by the above formula (2) at a content ratio of 2.62:93.79.
  • Colorant 2 was a compound containing the compound represented by the above formula (1) and the compound represented by the above formula (2) at a content ratio of 8.06:87.59.
  • colorants 3 to 8 were prepared according to the methods described in Preparation Examples 1 to 6 below.
  • Colorant 2 and Colorant 3 are added so that the content ratio ((A)/(B)) of the compound represented by the above formula (1) and the compound represented by the above formula (2) is 0.027. was blended with. The resulting blend is referred to as Colorant 7.
  • Colorant 2 and Colorant 3 are added so that the content ratio ((A)/(B)) of the compound represented by the above formula (1) and the compound represented by the above formula (2) is 0.028. was blended with. The resulting blend is referred to as colorant 8.
  • Example 1 to 5 Preparation of aqueous dispersions 1 to 5> Glass beads with a diameter of 0.2 mm were added to each component shown in Table 3 below, and the mixture was dispersed in a sand mill under water cooling for about 15 hours. The resulting liquid was filtered through glass fiber filter paper GC-50 (manufactured by ADVANTEC, filter pore size: 0.5 ⁇ m) to obtain aqueous dispersions 1 to 5 each having a colorant content of 15%.
  • GC-50 manufactured by ADVANTEC, filter pore size: 0.5 ⁇ m
  • ⁇ Comparative Examples 1 to 3 Preparation of aqueous dispersions 6 to 8> Glass beads with a diameter of 0.2 mm were added to each component shown in Table 4 below, and dispersed in a sand mill under water cooling for about 15 hours. The resulting liquid was filtered through glass fiber filter paper GC-50 (manufactured by ADVANTEC, filter pore size: 0.5 ⁇ m) to obtain aqueous dispersions 6 to 8 each having a colorant content of 15%.
  • GC-50 manufactured by ADVANTEC, filter pore size: 0.5 ⁇ m
  • Examples 6 to 10 Preparation of violet inks 1 to 5> Aqueous dispersions 1 to 5 obtained in Examples 1 to 5 and each component shown in Table 5 below are mixed, stirred for 30 minutes, and then filtered through a filter with a pore size of 5.0 ⁇ m (manufactured by Sartorius). Violet inks 1-5 were prepared by
  • each of the inks of Examples 6-10 was superior to each of the inks of Comparative Examples 4-6 in storage stability and filterability after storage.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Dispersion Chemistry (AREA)
  • Textile Engineering (AREA)
  • Pigments, Carbon Blacks, Or Wood Stains (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)

Abstract

L'invention concerne une dispersion colorée qui comprend de l'eau et un colorant comprenant un composé représenté par la formule (1) et un composé représenté par la formule (2), le colorant, en analyse par chromatographie liquide à haute performance, satisfaisant la relation ((A)/(B))<0.028, où (A) est la zone d'un pic attribuable au composé représenté par la formule (1) et (B) est la zone d'un pic attribuable au composé représenté par la formule (2).
PCT/JP2022/018121 2021-04-19 2022-04-19 Dispersion colorée WO2022224945A1 (fr)

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Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB271023A (en) * 1926-01-11 1927-05-11 British Dyestuffs Corp Ltd The manufacture and production of anthraquinone intermediates
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
JP2014080539A (ja) * 2012-10-18 2014-05-08 Seiko Epson Corp 昇華転写用インク、染色物の製造方法および染色物
CN105693530A (zh) * 2014-11-27 2016-06-22 江苏华尔化工有限公司 一种合成1,4-二氨基-2,3-二氯蒽醌的方法
CN107011701A (zh) * 2017-05-24 2017-08-04 上海贝通色彩科技有限公司 一种耐碱性分散染料组合物
CN108864729A (zh) * 2018-07-20 2018-11-23 江苏华尔化工有限公司 一种制备分散染料28号紫的工艺
CN108947875A (zh) * 2018-07-05 2018-12-07 南通沃兰化工有限公司 一种2,4-二苯砜基苯酚的合成方法

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB271023A (en) * 1926-01-11 1927-05-11 British Dyestuffs Corp Ltd The manufacture and production of anthraquinone intermediates
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
JP2014080539A (ja) * 2012-10-18 2014-05-08 Seiko Epson Corp 昇華転写用インク、染色物の製造方法および染色物
CN105693530A (zh) * 2014-11-27 2016-06-22 江苏华尔化工有限公司 一种合成1,4-二氨基-2,3-二氯蒽醌的方法
CN107011701A (zh) * 2017-05-24 2017-08-04 上海贝通色彩科技有限公司 一种耐碱性分散染料组合物
CN108947875A (zh) * 2018-07-05 2018-12-07 南通沃兰化工有限公司 一种2,4-二苯砜基苯酚的合成方法
CN108864729A (zh) * 2018-07-20 2018-11-23 江苏华尔化工有限公司 一种制备分散染料28号紫的工艺

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