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WO2012060343A1 - Composition d'encre à colorant azoïque et ensemble encre d'impression à jet d'encre l'utilisant - Google Patents

Composition d'encre à colorant azoïque et ensemble encre d'impression à jet d'encre l'utilisant Download PDF

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Publication number
WO2012060343A1
WO2012060343A1 PCT/JP2011/075116 JP2011075116W WO2012060343A1 WO 2012060343 A1 WO2012060343 A1 WO 2012060343A1 JP 2011075116 W JP2011075116 W JP 2011075116W WO 2012060343 A1 WO2012060343 A1 WO 2012060343A1
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Prior art keywords
ink composition
group
ink
water
mass
Prior art date
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Ceased
Application number
PCT/JP2011/075116
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English (en)
Japanese (ja)
Inventor
あさ子 近藤
秀洋 新井
梅田　真理子
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Nippon Kayaku Co Ltd
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Nippon Kayaku Co Ltd
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Priority to JP2012541860A priority Critical patent/JPWO2012060343A1/ja
Publication of WO2012060343A1 publication Critical patent/WO2012060343A1/fr
Anticipated expiration legal-status Critical
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • 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
    • 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
    • C09B29/00—Monoazo dyes prepared by diazotising and coupling
    • C09B29/34—Monoazo dyes prepared by diazotising and coupling from other coupling components
    • C09B29/36—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds
    • C09B29/3604—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom
    • C09B29/3617—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom
    • 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
    • D06P1/0032—Determining dye recipes and dyeing parameters; Colour matching or monitoring
    • 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
    • D06P1/02—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 azo dyes
    • D06P1/04—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 azo dyes not containing metal
    • 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
    • D06P1/44—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 insoluble pigments or auxiliary substances, e.g. binders
    • D06P1/60—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 insoluble pigments or auxiliary substances, e.g. binders using compositions containing polyethers
    • D06P1/613—Polyethers without nitrogen
    • D06P1/6131—Addition products of hydroxyl groups-containing compounds with oxiranes
    • D06P1/6133—Addition products of hydroxyl groups-containing compounds with oxiranes from araliphatic or aliphatic alcohols
    • 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 an ink composition containing a monoazo dye, in particular, an aqueous dispersion for ink jet printing, a disperse dye ink set including the same, and an ink jet printing method for polyester fibers using the same. It is characterized by excellent color reproducibility in a wide color reproduction range, particularly in the hue range from red to violet to blue to cyan, and good light fastness.
  • Ink-jet textile printing using an ink-jet printer requires no plate-making process and shortens the process compared with conventional printing methods such as screen printing, roller printing, rotary printing, etc .; There are many merits such as being able to print as it is; being able to produce a wide variety of products even in small quantities; drastically reducing waste of dye color paste; On the other hand, there are problems such as slow printing processing speed and difficulty in reproducing dark colors, which are often used in the range of sample production and small-scale production.
  • Ink for ink-jet printing using disperse dyes is required to give a sufficient density for color development, to have a wide range of color reproduction, and to be able to provide high-fastness printed matter.
  • Various ink sets have been proposed for these requirements.
  • the ink set using conventional dyes cannot completely reproduce the hue range obtained by the screen printing method, and uses an azo dye that has a narrow color reproduction range and provides high color density to give a sufficient density.
  • the conventional azo dye has a problem that the light fastness is insufficient. An ink set satisfying these points has not yet been provided.
  • the present inventors have developed a specific monoazo dye that can increase color reproducibility particularly in the hue range of red, violet, blue, and cyan, and can also obtain high light fastness.
  • the present invention has been completed by finding a red ink composition to be contained and a disperse dye ink set comprising the red ink composition and a cyan ink composition and / or a yellow ink composition.
  • the present invention relates to the following 1) to 8).
  • R 1 and R 2 are each independently a hydrogen atom, an optionally substituted phenyl group, an optionally substituted alkyl group having 1 to 6 carbon atoms, or aralkyl.
  • R 3 represents a hydrogen atom, a halogen atom, a nitro group, a cyano group, an amino group, or an alkyl group having 1 to 4 carbon atoms, and when a plurality of R 3 are present, they may be the same (N may be an integer of 1 to 5.)
  • the above 3) containing 10 to 25% by mass of the monoazo dye, 3 to 25% by mass of a dispersant, and 0.9 to 11.25% by mass of an ethylene oxide adduct of phytosterols and an ethylene oxide adduct of cholestanols.
  • An ink set for use in ink jet textile printing comprising the ink composition according to any one of 1) to 4) as a red ink composition.
  • a method for inkjet printing of hydrophobic fibers comprising using the ink set described in 5) or 6) above, printing a colorant on hydrophobic fibers by an inkjet method, and performing a steaming or baking treatment.
  • the ink composition and ink set of the present invention have excellent color reproducibility in ink-jet printing, particularly in the hue range of red, violet, blue, and cyan, and also have good light fastness. Therefore, according to the printing method using the same, a dyed product having excellent characteristics can be obtained.
  • the ink composition of the present invention contains a monoazo dye represented by the general formula (1), water, a dispersant, and a water-soluble organic solvent.
  • R 1 to R 3 in the general formula (1) are each an independent substituent.
  • R 1 and R 2 each independently represents a hydrogen atom, a phenyl group which may have a substituent, an alkyl group having 1 to 6 carbon atoms which may have a substituent, or an aralkyl group.
  • Examples of the substituent of the phenyl group which may have a substituent in R 1 and R 2 include an optionally substituted alkyl group having 1 to 4 carbon atoms, a hydroxy group, and an alkoxy having 1 to 4 carbon atoms.
  • the substitution position of each substituent is not particularly limited as long as substitution is possible.
  • Examples of the substituent of the alkyl group having 1 to 6 carbon atoms that may have a substituent in R 1 and R 2 include a hydroxy group, an alkoxy group having 1 to 4 carbon atoms, a hydroxy (C1-C4) alkoxy group, A phenoxy group etc. are mentioned.
  • alkyl group having 1 to 6 carbon atoms which may have a substituent include a methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, t-butyl group, n -Hexyl group, cyclohexyl group, hydroxymethyl group, 2-hydroxyethyl group, 2-hydroxypropyl group, 4-hydroxybutyl group, 3-hydroxybutyl group, 2-hydroxybutyl group, hydroxyethoxymethyl group, 2-hydroxyethoxy Ethyl group, 3-hydroxyethoxypropyl group, 3-hydroxyethoxybutyl group, 2-hydroxyethoxybutyl group, methoxymethyl group, methoxyethyl group, methoxypropyl group, ethoxymethyl group, ethoxyethyl group, ethoxypropyl group, propyloxy Methyl group, propyloxyethyl group, propyloxypro Group, phen
  • Examples of the aralkyl group in R 1 and R 2 include a lower alkyl group having 1 to 4 carbon atoms substituted with an aryl group, such as a benzyl group, a phenethyl group, a phenylpropyl group, a naphthylmethyl group, a naphthylethyl group. Etc.
  • a phenyl group, an alkoxyphenyl group having 1 to 4 carbon atoms, and a hydroxy (C1-C4) alkoxy (C1-C4) alkyl group are preferable, and a phenyl group and a hydroxyethoxyethyl group are particularly preferable.
  • R 3 represents a hydrogen atom, a halogen atom, a nitro group, a cyano group, an amino group, or an alkyl group having 1 to 4 carbon atoms.
  • Examples of the alkyl group having 1 to 4 carbon atoms in R 3 include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an s-butyl group, a t-butyl group, and an isobutyl group. It is done.
  • Examples of the halogen atom for R 3 include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
  • R 3 a chlorine atom, a bromine atom, a nitro group and a cyano group are preferable, and a nitro group and a cyano group are particularly preferable.
  • the substitution position of R 3 is not particularly limited as long as it can be substituted. When a plurality of R 3 are present, they may be the same or different.
  • the monoazo dye represented by the above general formula (1) contained in the ink composition of the present invention can be produced by the method described in Patent Document 1 (Japanese Patent Publication No. 61-39347) or an application thereof. .
  • a mixture of compounds in which R 1 and R 2 are different substituents can be obtained by mixing two or more types of dyes having a single structure. It can also be obtained by ring reaction.
  • compounds represented by the above formulas (2) and (3) are preferable, and a compound represented by the above formula (2) or the above formula (3) is preferable.
  • a single compound or a mixture of both compounds may be used.
  • the dispersant contained in the ink composition of the present invention is not particularly limited, but those usually used for ink jet inks and the like are preferable.
  • high molecular sulfonic acid preferably aromatic sulfonic acid formalin
  • aromatic sulfonic acid formalin examples include condensates and formalin condensates of lignin sulfonic acid.
  • aromatic sulfonic acid etc. in this invention when it describes as "sulfonic acid", it is used by the meaning containing the salt.
  • formalin condensate of aromatic sulfonic acid examples include formalin condensate of creosote oil sulfonic acid, formalin condensate of cresol sulfonic acid, formalin condensate of phenol sulfonic acid, formalin condensate of naphthalene sulfonic acid, ⁇ - Formalin condensate of naphthol sulfonic acid, formalin condensate of ⁇ -naphthalene sulfonic acid and ⁇ -naphthol sulfonic acid, formalin condensate of cresol sulfonic acid and 2-naphthol-6-sulfonic acid, and the like.
  • any of these condensates may be a salt such as a sodium salt.
  • the dispersant contained in the ink composition of the present invention is particularly preferably a formalin condensate of creosote oil sulfonic acid, a formalin condensate of naphthalene sulfonic acid, a formalin condensate of lignin sulfonic acid, or the like.
  • the aromatic sulfonic acid formalin condensate examples include, for example, Demol TRMN (trade name, manufactured by Kao Corporation), Demol TRMC (trade name, manufactured by Kao Corporation), and Demol TRM which is a special aromatic sulfonic acid formalin condensate. SNB (trade name, manufactured by Kao Corporation) and the like can be mentioned.
  • the water-soluble organic solvent contained in the ink composition of the present invention is not particularly limited as long as it has a wetting effect for the purpose of preventing clogging at the nozzle, and examples thereof include polyhydric alcohols and pyrrolidones.
  • examples of the polyhydric alcohols include polyhydric alcohols having 2 to 3 carbon atoms having 2 to 3 alcoholic hydroxyl groups, di- or trialkylene (2 or 3 carbon atoms) glycols, 4 or more repeating units, and a molecular weight.
  • Examples include polyalkylene (carbon number 2 or 3) glycol of about 20,000 or less, preferably liquid polyalkylene glycol.
  • water-soluble organic solvent examples include ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol, polyethylene glycol, polypropylene glycol, glycerin, trimethylolpropane, 1,3-pentanediol, 1,5-pentanediol, and the like. And monohydric alcohols, 2-pyrrolidone, N-methyl-2-pyrrolidone and the like.
  • a compound that dissolves in water and serves as a wetting agent is also included in the water-soluble organic solvent in the present invention, and examples thereof include urea, ethylene urea, and saccharides.
  • a solvent having a low solubility of the monoazo dye is preferable, and among these, a mixed solvent of glycerin and other solvents, preferably a mixed solvent of glycerin and other liquid polyhydric alcohols.
  • the content of the water-soluble organic solvent is preferably 5 to 40% by mass, and preferably 10 to 30% by mass, in the ink composition.
  • the ink composition of the present invention may contain an alkylene oxide adduct of phytosterols and / or an alkylene oxide adduct of cholestanols.
  • an alkylene oxide adduct having 2 to 4 carbon atoms of phytosterols is preferable, and an ethylene oxide (EO) adduct is particularly preferable.
  • the phytosterols include both phytosterols and hydrogenated phytosterols.
  • Examples of ethylene oxide adducts of phytosterols include ethylene oxide adducts of phytosterols and ethylene oxide adducts of hydrogenated phytosterols.
  • the alkylene oxide adduct of cholestanols is preferably an alkylene oxide adduct having 2 to 4 carbon atoms of cholestanols, and particularly preferably an ethylene oxide (EO) adduct.
  • EO ethylene oxide
  • alkylene oxide preferably alkylene oxide having 2 to 4 carbon atoms, more preferably ethylene oxide per mole of phytosterols or cholestanols is preferably about 10 to 50 mol and HLB is about 13 to 20.
  • the phytosterols ethylene oxide adducts include, for example, NIKKOLRTM BPS-20, NIKKOLRTM BPS-30 (all manufactured by Nikko Chemicals Co., Ltd., EO adduct of phytosterol), NIKKOLRTM BPSH-25 (manufactured by Nikko Chemicals Co., Ltd., hydrogenated phytosterol) EO adduct) and the like can be obtained from the market.
  • the ethylene oxide adduct of cholestanols can be obtained from the market as, for example, NIKKOLRTM DHC-30 (manufactured by Nikko Chemicals Co., Ltd., EO adduct of cholestanol).
  • water-insoluble monoazo dye is finely divided or finely divided, and then mixed with water, a dispersant, and an alkylene oxide adduct of phytosterols and / or an alkylene oxide adduct of cholestanols as appropriate. Then, a slurry in which the dye is dispersed is obtained, and if necessary, the concentration is adjusted by filtration and water dilution to obtain an aqueous dispersion.
  • the above stirring and mixing is preferably performed while making the water-insoluble monoazo dye fine.
  • the water-soluble organic solvent may be mixed together at the time of the above mixing, but it is preferable to add the water-soluble organic solvent to an aqueous dispersion not containing them to obtain an ink composition.
  • the concentration of the monoazo dye in the dispersed slurry is usually 15 to 35% by mass, and the concentration of the dispersing agent is 5 to 35% by mass.
  • the alkylene oxide adduct of phytosterols and / or the alkylene oxide adduct of cholestanols is usually used in an amount of 3 to 45% by mass with respect to the dispersant, and in total with the dispersant, 30 to 150% by mass with respect to the monoazo dye, The amount is preferably about 30 to 120% by mass, more preferably about 30 to 100% by mass.
  • the balance is water.
  • the concentration of the monoazo dye in the aqueous dispersion after the dispersed slurry, which is the ink composition of the present invention, is diluted with water as necessary, is usually 0.3 to 35% by mass, preferably 1 to 30% by mass, More preferably, it is 3 to 10%, and the concentration of the dispersant is usually 1 to 35% by mass, preferably 2 to 30% by mass, and more preferably 3 to 25% by mass.
  • the concentration of the alkylene oxide adduct of phytosterols and / or the alkylene oxide adduct of cholestanols is usually 0.1 to 15% by mass, and particularly preferred embodiments are ethylene oxide adducts of phytosterols and / or cholestanols. This is a case where 0.9 to 11.25% by mass of the ethylene oxide adduct is contained.
  • the balance is water and a water-soluble organic solvent.
  • a method of mixing the above monoazo dye with other components while making fine particles a method known per se is used for stirring and mixing using a sand mill (bead mill), roll mill, ball mill, paint shaker, ultrasonic disperser, microfluidizer, etc. Etc.
  • a sand mill (bead mill) is preferable.
  • dispersants have foaming properties
  • silicone-based, acetylene alcohol-based, etc. A very small amount of a foaming agent or the like may be added during grinding.
  • some antifoaming agents inhibit dispersion and micronization, and it is preferable to use those that do not affect the stability after micronization or dispersion.
  • the particle diameter of the monoazo dye in the ink composition of the present invention thus obtained is preferably about 50 to 150 nm as a volume average median diameter measured by a particle size distribution meter.
  • the ink composition of the present invention may contain additives as necessary depending on the purpose of use.
  • the ink additive that is added as necessary may coexist and be mixed together when mixing the above-mentioned monoazo dye and the other components. It is preferable to prepare an ink composition by adding an additive or the like.
  • the additive examples include antiseptic / antifungal agents and pH adjusters.
  • the antiseptic / antifungal agent include sodium dehydroacetate, sodium benzoate, sodium pyridinethione-1-oxide, zinc pyridinethione-1-oxide, 1,2-benzisothiazolin-3-one, 1-benz And an amine salt of isothiazolin-3-one.
  • the pH adjuster include alkali hydroxides such as sodium hydroxide, potassium hydroxide and lithium hydroxide, and tertiary amines such as triethanolamine, diethanolamine, dimethylethanolamine and diethylethanolamine. .
  • the total content of these additives is about 0 to 10%, preferably about 0.05 to 5%, based on the entire ink composition.
  • the ink composition of the present invention can be prepared by dispersing or mixing each component in water by a method known per se such as stirring and mixing using a homogenizer.
  • the ink composition of the present invention is usually 2 to 10 mPa ⁇ s when the viscosity at 25 ° C. is measured with an E-type viscometer and the surface tension is measured by a plate method from the viewpoint of high-speed ejection response. Usually, it is preferably in the range of 20 to 40 mN / m. Specifically, it may be adjusted to an appropriate physical property value in consideration of the discharge amount, response speed, ink droplet flight characteristics, etc. of the printer to be used. It is preferable to adjust the viscosity with the amount of a dispersant or a water-soluble organic solvent, and the surface tension with a silicone-based or acetylene alcohol-based antifoaming agent.
  • the present invention includes an ink set for ink jet textile printing comprising an ink composition containing the above monoazo dye.
  • the ink set is an ink set used for inkjet printing of a fabric polyester made of polyester fiber or the like, and may include a cyan ink composition and / or a yellow ink composition, or a black ink composition. Also good.
  • the cyan ink composition C.I. I. Examples thereof include an ink composition containing 0.1 to 20% by mass, preferably 0.5 to 7% by mass of Disperse Blue 60.
  • the yellow ink composition includes C.I. I. Examples thereof include an ink composition containing Disperse Yellow 114 in an amount of 0.1 to 20% by mass, preferably 0.5 to 7% by mass.
  • the cyan ink composition may contain other colorants for the purpose of adjusting the color tone.
  • the colorant include C.I. I. Disperse Blue 27, 54, 73, 77, 79, 79: 1, 87, 143, 165, 165: 1, 165: 2, 181, 185, 197, 225, 257, 266, 267, 281, 341, 353, Blue dyes such as 354, 358, 364, 365, and 368 are listed. Further, other disperse dyes may be included.
  • the red ink composition may contain other colorants of the dyes of the above formulas (2) and (3) for the purpose of adjusting the color tone.
  • the colorant include C.I. I. Disperse Red 73, 88, 91, 92, 111, 127, 131, 143, 145, 146, 152, 153, 154, 179, 191, 192, 206, 221, 258, 283, 302, 323, 328, 359, etc. Red dyes.
  • other reactive dyes may be included.
  • the yellow ink composition may contain other colorants for the purpose of adjusting the color tone.
  • the colorant include C.I. I.
  • Examples include yellow dyes such as Disperse Yellow 42, 49, 76, 83, 88, 93, 99, 119, 126, 160, 163, 165, 180, 183, 186, 198, 199, 200, 224, and 237.
  • other reactive dyes may be included.
  • colorants that may be added for the purpose of adjusting the color tone may be in a powdery or lump dry state, or in a wet cake or slurry state.
  • a dispersion agent such as a surfactant may be added for the purpose of suppressing particle aggregation during or after the synthesis of the colorant.
  • These commercially available colorants include grades for industrial dyeing, resin coloring, ink, toner, inkjet, etc., and the production method, purity, particle size, and the like are different. In order to suppress agglomeration after pulverization, those having smaller particles are preferable.
  • inorganic impurities In the production of the ink composition, it is preferable to use a material having as few impurities as possible in order to reduce the adverse effects on dispersion stability and ink ejection accuracy.
  • water that is not subjected to purification operations may contain metal ions such as calcium ions and magnesium ions, and when such water is used during the preparation of the ink composition, the ions and the like are mixed in a trace amount. To do.
  • inorganic salts and metal ions for convenience, they are described as “inorganic impurities”. Inorganic impurities not only significantly reduce the solubility and storage stability of the ink composition, but also cause corrosion and wear of the inkjet printer head.
  • the inorganic impurities contained in the ink composition In order to remove these inorganic impurities, it is desirable to remove as much as possible the inorganic impurities contained in the ink composition by using a known method such as an ultrafiltration method, a reverse osmosis method or an ion exchange method.
  • the amount of inorganic impurities contained in the total amount of the ink composition is usually 1% by mass or less, preferably 0.5% by mass or less, and particularly preferably 0.1% by mass or less.
  • the inkjet printing method of the present invention is a printing method in which a coloring agent is printed on a hydrophobic fiber, for example, a polyester fiber, and then steamed or baked by a known method to dye the dye in the ink into the hydrophobic fiber. It is. Steaming can be carried out with a high-temperature steamer, usually at 170 to 180 ° C., usually for about 10 minutes, and with a high-pressure steamer, usually at 120-130 ° C., usually for about 20 minutes (wet heat fixation). In baking (thermosol), it can be dyed by a treatment of usually 190 ° C. to 210 ° C., usually 60 to 120 seconds (dry heat fixation).
  • any method after dyeing, it is preferable from the standpoint of fiber fastness to wash away undyed dye on the fiber surface by a method known per se, for example, alkali reduction washing or soaping treatment.
  • staining method of this invention is also contained in this invention.
  • hydrophobic fibers examples include polyester fibers, nylon fibers, triacetate fibers, diacetate fibers, polyamide fibers, and blended products using two or more of these fibers. Further, it may be a blended product of these and recycled fibers such as rayon or natural fibers such as cotton, silk and wool.
  • These hydrophobic fibers are preferably provided with an ink receiving layer (bleeding prevention layer).
  • the method for forming the ink receiving layer is a generally known technique.
  • the ink receiving layer can be provided on the hydrophobic fiber by applying this technique, and the fiber having the ink receiving layer is commercially available. .
  • the ink receiving layer is not particularly limited as long as it has the function.
  • an ink composition for inkjet printing of a monoazo dye having a wide color reproducibility in a hue range of red, violet, blue, and cyan and excellent in light fastness and storage stability can be obtained.
  • the composition is also excellent in ejection stability.
  • the viscosity is R-115 type viscometer (E type) manufactured by Toki Sangyo Co., Ltd.
  • the surface tension is CBVP-Z type surface tension meter (plate method) manufactured by Kyowa Interface Science Co., Ltd.
  • the average particle size is 0.5% of the colorant concentration.
  • the volume average median diameter was measured using a Nikkiso particle size distribution analyzer Nanotrac UPA-EX150.
  • the hue was measured for ⁇ E * and the like by measuring the color of the dyed cloth using a colorimeter manufactured by GRETAG-MACBETH, trade name: SpectroEye.
  • the diazonium salt solution can be obtained by adding 50 parts of 90% concentrated sulfuric acid to 16 parts of 2-cyano-4-nitroaniline, cooling to 0-5 ° C., and then adding 31 parts of 40% nitrosylsulfuric acid solution little by little. It was. After stirring for 2 hours, excess nitrosylsulfuric acid was quenched by a conventional method. After the diazonium salt solution was dropped, caustic soda was gradually added so that the pH of the reaction solution was 2 to 3. After completion of the coupling reaction, the mixture is heated to 70 to 80 ° C., filtered, washed with water, and dried to obtain 43 parts of the desired mixture of compounds represented by the above formulas (2) and (3). Obtained.
  • Example 1 Aqueous dispersion Each component having the composition ratio shown in Table 1 is subjected to a dispersion treatment for about 15 hours under water cooling using 0.2 mm diameter glass beads in a sand mill. After the dispersion treatment is completed, 150 parts of ion-exchanged water is added. In addition, each aqueous dispersion having a dye concentration of 15% was prepared. Subsequently, the dispersion was filtered with glass fiber filter paper GC-50 (manufactured by Toyo Filter Paper Co., Ltd.) to remove coarse particles.
  • GC-50 manufactured by Toyo Filter Paper Co., Ltd.
  • Each aqueous dispersion obtained had a dye concentration of about 15%, an average particle size of 120 nm, and a viscosity of 5.5 mPa ⁇ s.
  • Labelin WRTM is a formalin condensate powder of creosote oil sulfonic acid manufactured by Dai-ichi Kogyo Seiyaku Co., Ltd. (15 parts of the condensate powder is mixed with 40% aqueous solution with ion-exchanged water), and NIKKOLRTM BPS-30. Is an EO (30) adduct of phytosterol manufactured by Nikko Chemicals Co., Ltd. 10% Surfynol RTM104PG is a 10-fold dilution of acetylene alcohol-based antifoaming agent manufactured by Air Products with propylene glycol. .
  • Ink composition A red ink composition was prepared by mixing with the formulation shown in Table 2, and pressure filtered through a 0.8 micron filter (DISMIC 25CS080AN) to obtain an ink composition for printing.
  • the viscosity was 3.5 mPa ⁇ s
  • the average particle size was 120 nm
  • the surface tension was 37.9 mN / m.
  • a cyan ink composition having the formulation shown in Table 4 was prepared in the same manner as in Example 1 to obtain an ink composition for textile printing.
  • the viscosity was 3.6 mPa ⁇ s
  • the average particle size was 70 nm
  • the surface tension was 36.8 mN / m.
  • the obtained ink composition was dyed in the same manner as in Example 1 to obtain a dyed fabric.
  • a yellow ink composition having the formulation shown in Table 6 was prepared in the same manner as in Example 1 to obtain an ink composition for textile printing.
  • the viscosity was 3.3 mPa ⁇ s
  • the average particle size was 100 nm
  • the surface tension was 36.2 mN / m.
  • the obtained ink composition was dyed in the same manner as in Example 1 to obtain a dyed fabric.
  • Example 2 The red ink composition of Example 1: the cyan ink composition of Reference Example 1 was printed on a polyester fiber provided with an ink receiving layer with a commercially available printer (PM-740C manufactured by Seiko Epson Corporation) at a ratio of 3: 1. A dyed fabric was obtained in the same manner as in Example 1.
  • C.I. I. Disperse Red 152 and 154 were used, respectively, to prepare red inks of comparative examples.
  • C.I. I. Disperse Red 152 is made by Nippon Kayaku Co., Ltd. as Kayalon Polyester Light Red BS 200
  • C.I. I. Disperse Red 154 can be obtained as Kayalon Polyester Red BR-S manufactured by Nippon Kayaku Co., Ltd.
  • Example 1 An aqueous dispersion was obtained in the same manner as in Example 1 with the formulation shown in Table 7.
  • the aqueous dispersion had a dye concentration of 15%, an average particle size of 90 nm, and a viscosity of 4.5 mPa ⁇ s.
  • a red ink composition having the formulation shown in Table 8 was prepared in the same manner as in Example 1 to obtain an ink composition for textile printing.
  • the viscosity was 4.0 mPa ⁇ s
  • the average particle size was 90 nm
  • the surface tension was 38.3 mN / m.
  • the obtained ink composition was dyed in the same manner as in Example 1 to obtain a dyed fabric.
  • Example 2 An aqueous dispersion was obtained in the same manner as in Example 1 with the formulation shown in Table 9. The dye concentration of the aqueous dispersion was 15%, the average particle size was 100 nm, and the viscosity was 5.0 mPa ⁇ s.
  • a red ink composition having the formulation shown in Table 10 was prepared in the same manner as in Example 1 to obtain an ink composition for textile printing.
  • the viscosity was 4.0 mPa ⁇ s
  • the average particle size was 90 nm
  • the surface tension was 37.6 mN / m.
  • the obtained ink composition was dyed in the same manner as in Example 1 to obtain a dyed fabric.
  • Comparative Example 3 The red ink composition of Comparative Example 1: The cyan ink composition of Reference Example 1 was printed on polyester fibers provided with an ink receiving layer with a commercially available printer (PM-740C manufactured by Seiko Epson Corporation) at a ratio of 3: 1. A dyed fabric was obtained in the same manner as in Example 1.
  • the dyed fabric printed with the ink set for inkjet printing of the present invention has a wide color reproduction range in the hue range of red to violet to blue to cyan as compared with the comparative examples. It is clear that this is a high-quality dyed cloth with excellent light fastness.

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

Abstract

La présente invention concerne une composition d'encre qui contient le colorant monoazoïque représenté par la formule générale (1), de l'eau, un agent dispersant et un solvant organique soluble dans l'eau, en tant que composition d'encre rouge convenant à un ensemble encre ayant une large plage de reproduction de couleurs pour l'impression à jet d'encre ; la composition présente notamment une large reproductibilité des couleurs dans la plage de teintes des rouge-violet-bleu-cyan et une solidité à la lumière favorable. L'invention concerne également : un ensemble encre doté de la composition d'encre ; un procédé d'impression à jet d'encre qui l'utilise ; et un article coloré, obtenu au moyen du procédé. Dans la formule, R1 et R2 désignent chacun indépendamment un atome d'hydrogène, un groupe phényle qui peut avoir un substituant, un groupe alkyle ayant de 1 à 6 atomes de carbone et qui peut avoir un substituant ou un groupe aralkyle. R3 désigne un atome d'hydrogène, un atome d'halogène, un groupe nitro, un groupe cyano, un groupe amino ou un groupe alkyle ayant de 1 à 4 atomes de carbone ; R3 peut être identique ou différent lorsqu'il en existe une pluralité ; et n désigne un entier, compris entre 1 et 5.
PCT/JP2011/075116 2010-11-04 2011-10-31 Composition d'encre à colorant azoïque et ensemble encre d'impression à jet d'encre l'utilisant Ceased WO2012060343A1 (fr)

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2018154790A (ja) * 2017-03-21 2018-10-04 セイコーエプソン株式会社 分散剤及び捺染インク組成物
WO2022025034A1 (fr) * 2020-07-31 2022-02-03 日本化薬株式会社 Liquide colorant, ensemble d'encres, support d'enregistrement, et procédé d'impression sur textile pour fibres hydrophobes
CN119528808A (zh) * 2024-11-25 2025-02-28 浙江闰土股份有限公司 高日晒红色染料中间体及其制备方法

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6139347B2 (fr) * 1972-03-10 1986-09-03 Basf Ag
JP2004059687A (ja) * 2002-07-26 2004-02-26 Fuji Photo Film Co Ltd 着色組成物、インクジェット記録用インク、インクジェット記録方法、感熱記録材料、カラートナー、およびカラーフィルター
JP2007238687A (ja) * 2006-03-06 2007-09-20 Nippon Kayaku Co Ltd インクジェット捺染方法

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6139347B2 (fr) * 1972-03-10 1986-09-03 Basf Ag
JP2004059687A (ja) * 2002-07-26 2004-02-26 Fuji Photo Film Co Ltd 着色組成物、インクジェット記録用インク、インクジェット記録方法、感熱記録材料、カラートナー、およびカラーフィルター
JP2007238687A (ja) * 2006-03-06 2007-09-20 Nippon Kayaku Co Ltd インクジェット捺染方法

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2018154790A (ja) * 2017-03-21 2018-10-04 セイコーエプソン株式会社 分散剤及び捺染インク組成物
CN108624146A (zh) * 2017-03-21 2018-10-09 精工爱普生株式会社 分散剂及印染油墨组合物
WO2022025034A1 (fr) * 2020-07-31 2022-02-03 日本化薬株式会社 Liquide colorant, ensemble d'encres, support d'enregistrement, et procédé d'impression sur textile pour fibres hydrophobes
CN119528808A (zh) * 2024-11-25 2025-02-28 浙江闰土股份有限公司 高日晒红色染料中间体及其制备方法

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