WO2018163966A1 - Encre, procédé d'impression sur tissu par jet d'encre, cartouche d'encre, imprimante à jet d'encre, et tissu coloré - Google Patents

Encre, procédé d'impression sur tissu par jet d'encre, cartouche d'encre, imprimante à jet d'encre, et tissu coloré Download PDF

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Publication number
WO2018163966A1
WO2018163966A1 PCT/JP2018/007846 JP2018007846W WO2018163966A1 WO 2018163966 A1 WO2018163966 A1 WO 2018163966A1 JP 2018007846 W JP2018007846 W JP 2018007846W WO 2018163966 A1 WO2018163966 A1 WO 2018163966A1
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Prior art keywords
ink
dye
polymer
pigment
structure derived
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PCT/JP2018/007846
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English (en)
Japanese (ja)
Inventor
藤江　賀彦
誠 大元
小林　博美
未奈子 原
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富士フイルム株式会社
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Publication of WO2018163966A1 publication Critical patent/WO2018163966A1/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
    • C09B69/00—Dyes not provided for by a single group of this subclass
    • C09B69/10—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds
    • C09B69/109—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds containing other specific dyes
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
    • B41J—TYPEWRITERS; SELECTIVE PRINTING MECHANISMS, i.e. MECHANISMS PRINTING OTHERWISE THAN FROM A FORME; CORRECTION OF TYPOGRAPHICAL ERRORS
    • B41J2/00—Typewriters or selective printing mechanisms characterised by the printing or marking process for which they are designed
    • B41J2/005—Typewriters or selective printing mechanisms characterised by the printing or marking process for which they are designed characterised by bringing liquid or particles selectively into contact with a printing material
    • B41J2/01—Ink jet
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
    • B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
    • B41M5/00—Duplicating or marking methods; Sheet materials for use therein
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • 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
    • C09B67/0085—Non common dispersing agents
    • C09B67/009—Non common dispersing agents polymeric dispersing agent
    • 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
    • C09B69/00—Dyes not provided for by a single group of this subclass
    • C09B69/10—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds
    • C09B69/103—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds containing a diaryl- or triarylmethane dye
    • 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
    • C09B69/00—Dyes not provided for by a single group of this subclass
    • C09B69/10—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds
    • C09B69/106—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds containing an azo dye
    • 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
    • C09D11/322—Pigment 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
    • C09D11/328—Inkjet printing inks characterised by colouring agents characterised by dyes
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06B—TREATING TEXTILE MATERIALS USING LIQUIDS, GASES OR VAPOURS
    • D06B1/00—Applying liquids, gases or vapours onto textile materials to effect treatment, e.g. washing, dyeing, bleaching, sizing or impregnating
    • 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
    • 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
    • D06P7/00—Dyeing or printing processes combined with mechanical treatment

Definitions

  • the present invention relates to an ink, an ink jet textile printing method, an ink cartridge, an ink jet printer, and a colored cloth.
  • Ink-jet printing does not require the production of a plate, can quickly form an image with excellent gradation, and uses only a necessary amount of ink as a formed image, so it has environmental advantages such as less waste liquid. It can be said that this is an excellent printing method.
  • Patent Document 1 describes an ink jet textile printing method using a pigment.
  • a pigment and a surfactant as a dispersant are mixed in water and then finely dispersed with an attritor or a mill machine together with glass beads, zirconia beads, titania beads, or stainless steel balls, etc., are used as a colorant. It has been. Then, this colorant is diluted with a reducer containing an emulsion resin for fixing the pigment, a pigment ink is prepared, adhered to the fiber by an ink jet method, and the resin is fused by a heating roller to fix the pigment.
  • Patent Documents 2 and 3 describe ink-jet inks containing a polymer linked with a dye.
  • Patent Document 1 the ink jet textile printing using the ink containing the pigment described in Patent Document 1 cannot be said to be excellent in image sharpness and wet friction fastness. Further, Patent Documents 2 and 3 do not specifically disclose textile printing, and do not describe any of the above problems.
  • An object of the present invention is to provide an ink capable of providing a colored cloth excellent in image sharpness and fastness to wet friction, an ink jet printing method using the ink, an ink cartridge and an ink jet printer having the ink, and the colored cloth. Is to provide.
  • An ink comprising an aqueous dispersion of a polymer having a structure derived from a dye, and a pigment.
  • the ink according to ⁇ 1> which is for inkjet textile printing.
  • the pigment is Carbon black, Aniline black, C. I. Pigment Yellow 3, 12, 53, 55, 74, 81, 83, 93, 94, 95, 97, 98, 100, 101, 104, 108, 109, 110, 117, 120, 128, 138, 153, 155, 180, 185, C. I.
  • the ink according to ⁇ 1> or ⁇ 2> which is at least one selected from the group consisting of: ⁇ 4>
  • the structure derived from the dye is a structure derived from any dye selected from an azo compound, stilbene, triarylmethane, xanthene, indoaniline, indophenol, nigrosine, anthraquinone, quinophthalone, dicyanostyryl compound, and phthalocyanine.
  • ⁇ 5> The ink according to any one of ⁇ 1> to ⁇ 4>, wherein the polymer having a structure derived from the dye is polyurethane.
  • ⁇ 6> The ink according to any one of ⁇ 1> to ⁇ 5>, wherein the polymer having a structure derived from the dye is a polymer having a crosslinked structure.
  • the polymer having a structure derived from the dye melts at 200 ° C.
  • the ink further comprises an aqueous dispersion of a water-insoluble polymer having no structure derived from a dye.
  • An inkjet printing method comprising a step of directly printing the ink according to any one of ⁇ 8> on a fabric by an inkjet method.
  • An aqueous pretreatment liquid containing an aggregating agent is applied to a fabric to obtain a pretreated fabric, and the ink according to any one of ⁇ 1> to ⁇ 8> is used in an ink jet method.
  • An inkjet printing method comprising a step of printing on a pretreated fabric.
  • ⁇ 12> The inkjet printing method according to ⁇ 11>, wherein the polymer having a structure derived from the dye is melted in the heat treatment step.
  • ⁇ 13> An ink cartridge having the ink according to any one of ⁇ 1> to ⁇ 8>.
  • ⁇ 14> ⁇ 1> to ⁇ 8>
  • ⁇ 15> A colored fabric comprising a fabric, a polymer having a structure derived from a dye, and a pigment.
  • an ink that can provide a colored cloth excellent in image sharpness and fastness to wet friction, an ink jet printing method using the ink, an ink cartridge and an ink jet printer having the ink, and the colored cloth Can be provided.
  • a numerical range expressed using “to” means a range including numerical values described before and after “to” as a lower limit value and an upper limit value.
  • substituent selected from substituent group A refers to substituents described in [0012] to [0051] of International Publication No. 2015/199135.
  • substituent group A1 includes the following substituents.
  • Substituent group A1 A halogen atom, an alkyl group (preferably 1 to 30 carbon atoms), a cycloalkyl group (preferably 3 to 30 carbon atoms), an aryl group (preferably 6 to 30 carbon atoms), a heterocyclic group (preferably 3 to 3 carbon atoms) 30), acyl groups (preferably having 2 to 30 carbon atoms), hydroxyl groups, carboxyl groups, sulfo groups, cyano groups, nitro groups, alkoxy groups (preferably having 1 to 30 carbon atoms), aryloxy groups (preferably having carbon numbers) 6-30), an acyloxy group (preferably having 2 to 30 carbon atoms), an alkoxycarbonyl group (preferably having 2 to 30 carbon atoms), an aryloxycarbonyl group (preferably having 7 to 30 carbon atoms), a carbamoyl group, a sulfamoyl group, Alkylsulfonyl group (preferably having 1 to 30 carbon atoms), aryls
  • the ionic group such as a sulfo group or a carboxyl group may be in a state containing a cation or an anion (also referred to as a “salt state”).
  • the carboxyl group, the phosphate group, and the sulfo group may be in a state containing a cation.
  • the cation that forms a salt state include an ammonium ion, an alkali metal ion (eg, lithium ion, sodium ion). Potassium ions) and organic cations (eg, tetramethylammonium ions, tetramethylguanidinium ions, tetramethylphosphonium).
  • the ink of the present invention includes at least a polymer aqueous dispersion having a structure derived from a dye and a pigment.
  • the ink of the present invention is preferably used for inkjet printing.
  • each component will be described.
  • the structure derived from a dye means one or more arbitrary hydrogen atoms from an organic compound used as a dye.
  • the dye polymer is a pigment multimer including a structure derived from a dye, and may be a linear polymer or a network polymer. In the case of a linear polymer, the structure derived from the dye may be included in the main chain of the polymer, or may be included in the side chain.
  • the dye polymer is preferably a polymer having a repeating unit containing a structure derived from a dye.
  • the method for obtaining the dye polymer is arbitrary, but a method for obtaining a dye polymer by polymerizing or copolymerizing a monomer containing a structure derived from a dye, or a polymer that does not have a structure derived from a dye in advance. Is prepared, and then a structure derived from a dye is introduced by a polymer reaction or the like to obtain a dye polymer.
  • the method for producing the dye polymer or the polymer having no structure derived from the dye is not particularly limited, but those synthesized by radical polymerization, addition polymerization or condensation polymerization are preferably used.
  • CI color index
  • Examples of structures derived from dyes include azo compounds (monoazo compounds, disazo compounds, trisazo compounds, polyazo compounds), stilbenes, carotenoids, diarylmethanes, triarylmethanes, xanthenes, acridines, quinolines, methines (monomethine, polymethine), A structure derived from any dye selected from azomethine, aniline, indoaniline, indamine, indophenol, azine, oxazine, thiazine, anthraquinone, indigo, quinophthalone, digrosine, porphyrin, dicyanostyryl compound, cyanine, and phthalocyanine Including.
  • the structure derived from the dye is azo compound, stilbene, diarylmethane, triarylmethane, xanthene, acridine, quinoline, polymethine, monomethine, azomethine, indoaniline, indophenol, nigrosine, oxazine, thiazine, anthraquinone, indigo, quinophthalone, porphyrin
  • an azo compound, stilbene, triarylmethane, xanthene, indoaniline, indophenol, nigrosine, anthraquinone, quinophthalone is preferable. More preferably, it includes a structure derived from any one of dyes selected from phthalocyanines, dicyanostyryl compounds, and phthalocyanines.
  • the dye may be a water-soluble dye or a water-insoluble dye, but it may be a water-insoluble dye from the viewpoint of water resistance and washing resistance of the dye polymer. preferable. Moreover, it is preferable that it is a dye which does not have ionic groups, such as a carboxyl group, a sulfo group, a phosphoric acid group, these salts, and an ammonium group. Such a dye is not particularly limited, and for example, a water-insoluble dye such as a disperse dye may be used, or a water-soluble dye obtained by removing an ionic group may be used.
  • the dye polymer a polymer containing a structure derived from a dye in the main chain or side chain is preferably used.
  • the polymer constituting the main chain in the polymer containing a structure derived from a dye in the main chain or side chain is not particularly limited, but an acrylic polymer, urethane polymer (polyurethane), urea polymer (polyurea) or styrene polymer is preferably used.
  • an acrylic polymer or a urethane polymer is preferable, and a urethane polymer is most preferable.
  • the acrylic polymer in the present invention is a polymer having at least one type of repeating unit from the group consisting of repeating units derived from (meth) acrylic acid and repeating units derived from (meth) acrylic acid esters.
  • (meth) acrylic acid represents at least one of acrylic acid and methacrylic acid
  • (meth) acrylic acid ester represents at least one of acrylic acid ester and methacrylic acid ester.
  • the urethane polymer in the present invention is a polymer having a urethane bond in the main chain, and includes a compound having two or more hydroxyl groups (polyol compound) and a compound having two or more isocyanate groups (polyisocyanate compound). Formed by reaction.
  • the urethane polymer may be referred to as polyurethane.
  • the urethane polymer in the present invention may further be a polymer having a urea bond.
  • a polymer having a urethane bond and a urea bond is also referred to as “polyurethane / urea”.
  • polyurethane / urea As one type of preferred form of the dye polymer in the present invention, there is a polyurethane / urea in which a structure derived from a dye and a first partial structure including a urethane bond and a second partial structure including a urethane bond are bonded by a urea bond. Can be mentioned.
  • the urea polymer in the present invention is a polymer having a urea bond in the main chain, and is formed by a reaction between a compound having two or more amino groups (polyamine compound) and a polyisocyanate compound.
  • the urea polymer is sometimes referred to as polyurea.
  • the styrene polymer in this invention means the polymer which has a repeating unit derived from styrene.
  • the dye polymer is polyurethane from the viewpoint of improving color developability. When the dye polymer is polyurethane, since the structure derived from the dye is not introduced into the side chain of the polymer but introduced into the main chain, the structure derived from the dye is less likely to aggregate and the color developability is improved. I guess.
  • the structure derived from the dye in the dye polymer is not limited as long as the effect of the present invention is achieved, but an arbitrary hydrogen atom from the dye represented by any one of the following general formulas (M1) to (M9) is 1
  • the dye residue is preferably one or more (preferably one or two) removed, and is represented by any one of the following general formulas (M1) to (M3), (M5), (M7) to (M9). More preferably, it is a dye residue obtained by removing one or more (preferably one or two) arbitrary hydrogen atoms from the dye.
  • general formula (M2) and (M3) shall also include each resonance structure.
  • R 101 to R 110 each independently represents a hydrogen atom or a substituent.
  • R 201 to R 215 each independently represent a hydrogen atom or a substituent, X 201 represents a monovalent anion, and n201 represents 0 or 1.
  • R 301 to R 317 each independently represent a hydrogen atom or a substituent, X 301 represents a monovalent anion, and n301 represents 0 or 1.
  • R 402 to R 407 each independently represent a hydrogen atom or a substituent
  • Ar 401 represents a phenyl group, a naphthyl group, or a heterocyclic group, and the phenyl group, the naphthyl group, or The heterocyclic group may further have a substituent.
  • R 501 to R 508 each independently represent a hydrogen atom or a substituent.
  • R 601 to R 602 each independently represents a hydrogen atom or a substituent
  • R 603 represents a hydrogen atom or a substituent
  • Ar 601 represents a phenyl group, a naphthyl group, or a heterocyclic group.
  • R 701 to R 706 each independently represent a hydrogen atom or a substituent.
  • R 811 to R 818 and R 821 to R 828 each independently represent a hydrogen atom or a substituent.
  • R 1 to R 18 each independently represents a hydrogen atom or a substituent.
  • R 19 and R 20 each independently represents an alkyl group or a hydroxyalkyl group.
  • X 201 in the general formula (M2) and X 301 in the general formula (M3) are preferably chlorine ion, acetate ion, triflate ion, tetrafluoroborate ion, tetrakis (pentafluorophenyl) borate ion, perchlorate ion, or Bis (trifluoromethanesulfonyl) imide anion is preferred.
  • Some of the dyes represented by the general formulas (M1) to (M9) are classified by color index, and can be synthesized by a conventionally known method (for example, Japanese Patent Publication No. 7-49583, patent) No. 5715380, International Publication No. 2010/110199, Japanese Translation of PCT International Publication No. 2002-509957, etc.).
  • the weight average molecular weight (Mw) of the dye polymer is preferably 3,000 to 2,000,000, more preferably 3,000 to 1,000,000, and 3,000 to 200,000 is particularly preferred.
  • the weight average molecular weight of the dye polymer can be measured by gel permeation chromatography (GPC).
  • the dye polymer may have a structure derived from a dye as an essential structure, but it is preferable to introduce a dispersing group from the viewpoint of dispersibility in water.
  • the dispersing group may be ionic or nonionic. At least one of a hydrophobic group (an electrically neutral non-polar group having low affinity with water) and an ionic group (an electrically ionic polar group having high affinity with water) Repeating units containing may be introduced.
  • the molecular structure of the dye polymer may be linear or branched, may be random, alternating, periodic, or block, and may be a graft polymer designed with a trunk and branch structure.
  • the dye polymer may have a structure having an ionic group as a dispersing group.
  • the introduction amount of the structure having an ionic group in the dye polymer is preferably such that the acid value or amine value of the dye polymer is 1 to 60 mgKOH / g, and is preferably 1 to 30 mgKOH / g. More preferably. Within the above range, the dispersion stability and wash fastness of the aqueous dispersion of the dye polymer are excellent.
  • the acid value or amine value can be determined by a neutralization titration method such as JIS (Japanese Industrial Standard) K 0070.
  • the dye polymer may have a structure having a nonionic group as a dispersing group.
  • the introduction amount of the structure (monomer unit) having a nonionic group as a dispersing group is preferably 1 to 40% by mass, and more preferably 5 to 30% by mass. Within the above range, the dispersion stability and wash fastness of the aqueous dispersion of the dye polymer are excellent.
  • the dye polymer preferably has an anionic group.
  • the anionic group is preferably an acid group.
  • the dye polymer preferably has a crosslinked structure.
  • the crosslinked structure represents a structure obtained by using a compound having a total of three or more hydroxyl groups and isocyanate groups in the molecule as at least one monomer. Examples of the compound having three or more hydroxyl groups in the molecule include glycerin, polyglycerin, trimethylolpropane, pentaerythritol and the like.
  • Examples of the compound having three or more isocyanate groups in the molecule include polymeric MDI (manufactured by Wako Pure Chemical Industries, Aldrich or Tosoh Corporation), duranate (manufactured by Asahi Kasei Corporation, trade name), and the like.
  • polymeric MDI manufactured by Wako Pure Chemical Industries, Aldrich or Tosoh Corporation
  • duranate manufactured by Asahi Kasei Corporation, trade name
  • a polymer having a crosslinked structure is hardly soluble in an organic solvent
  • DMSO dimethyl sulfoxide
  • NMP N-methylpyrrolidone
  • THF tetrahydrofuran
  • the dye polymer is melt-dyed, the dye polymer is preferably melted at a heat treatment temperature or lower. Since the heat treatment step is preferably performed at 100 to 200 ° C., the dye polymer is preferably melted at 200 ° C. or less, and more preferably at 180 ° C. or less.
  • the Tg (glass transition temperature) of the dye polymer is preferably 200 ° C. or lower, more preferably 180 ° C. or lower, and even more preferably 150 ° C. or lower.
  • the Tg of the dye polymer can be measured by DSC (differential scanning calorimetry).
  • the dye polymer has a higher Tg by having a structure derived from a dye as compared with a polymer not having a structure derived from a dye.
  • the acrylic polymer in which the structure derived from the dye is introduced into the side chain of the (meth) acrylate ester it may not melt at 200 ° C. depending on the structure or composition, but the main chain is polyurethane, and the main chain or side chain A polymer having a structure derived from a dye often melts at 200 ° C. or lower.
  • the aqueous dispersion of dye polymer contains at least water and the dye polymer, and may further contain an aqueous organic solvent. Further, depending on the method for producing the aqueous dispersion of the dye polymer, either a low molecular surfactant or a high molecular dispersant may be used together or not (so-called self-dispersing).
  • the dye polymer can be used alone or in admixture of two or more.
  • the above-described dye polymer is used not in a state dissolved in water but in a state dispersed in water (water dispersion).
  • the polymer In the state where the dye polymer is dispersed in water, unlike the state in which the dye polymer is dissolved in water, the polymer is substantially insoluble in water, and thus is excellent in terms of water resistance such as washing resistance and sweat resistance.
  • the dye polymer In the ink-jet printing method of the present invention, a step of washing with water after printing is unnecessary, and therefore the dye polymer is a polymer that is substantially insoluble in water.
  • the dye polymer that is insoluble in water is dispersed as particles, and the average particle diameter is preferably 50 to 500 nm.
  • the dye polymer is not present as particles in water. It is preferable to use ultrapure water as water.
  • the dye polymer When dispersed in water, the dye polymer is easily compatible with water (easy to get wet) and electrostatic repulsion (repulsive force) as a property of the dye polymer itself or by adsorption with the low molecular surfactant or polymer dispersant used in combination. ) Or steric repulsion prevents re-aggregation of the fine particles of the dye polymer, and has a function of suppressing sedimentation.
  • the dye polymer is particulate in the aqueous dispersion.
  • the average particle diameter of the particulate dye polymer in the aqueous dispersion of the dye polymer is preferably 50 to 500 nm, more preferably 50 to 300 nm, and particularly preferably 50 to 200 nm. Within this range, the fabric can be printed by the ink jet method.
  • the average particle size in the present specification the value of the volume average size (MV) measured using a particle size distribution measuring device (Nanotrack UPA EX150, trade name, manufactured by Nikkiso Co., Ltd.) was used.
  • the content of the dye polymer in the dye polymer aqueous dispersion is preferably 0.1 to 40% by mass, more preferably 1 to 30% by mass, and particularly preferably 3 to 25% by mass. Within this range, a high-density colored cloth can be obtained in printing while ensuring storage stability as an inkjet ink.
  • the water content in the dye polymer aqueous dispersion is preferably 50 to 95% by mass, more preferably 55 to 90% by mass, and particularly preferably 60 to 90% by mass. This range is preferable because the stability of the aqueous dispersion and the ejection stability as an inkjet ink can be imparted. The stability of the aqueous dispersion indicates that precipitation or the like hardly occurs.
  • the low molecular surfactant or the high molecular dispersant is preferably a low molecular surfactant or a high molecular dispersant having a hydrophobic group and an ionic group, and is added when the dye polymer is dispersed.
  • the low molecular surfactant or polymer dispersant adsorbs to the surface of the dye polymer and blends (wet) it with water, and the dye polymer fine particles ground by mechanical action are electrostatically repulsive (repulsive) or steric repulsive. This prevents the re-aggregation of fine particles and has a function of suppressing sedimentation.
  • the content of the low molecular surfactant is preferably in the range of 0.001% by mass to 5.0% by mass with respect to the total mass of the dye polymer aqueous dispersion, and the surface tension of the aqueous dispersion is within this range. Is preferably adjusted arbitrarily.
  • the content of the polymeric dispersant is preferably in the range of 0.001% by mass to 50% by mass with respect to the total mass of the dye polymer aqueous dispersion, and the surface tension of the aqueous dispersion can be arbitrarily set within this range. It is preferable to adjust to.
  • the method for producing an aqueous dispersion of a dye polymer is as follows: (I) After mixing a dye polymer powder or paste and, if necessary, a low molecular surfactant or a high molecular dispersant in water or an aqueous organic solvent, glass beads, zirconia beads, titania beads, Or a method of finely dispersing with an attritor or a mill with stainless steel balls, (Ii) a method of obtaining an aqueous dispersion of a dye polymer by synthesizing a dye polymer in an organic solvent and then adding water, optionally a surfactant or a solvent, and removing a solvent other than water; (Iii) An organic solvent, a compound having a structure derived from a dye and having a group that reacts with a polyisocyanate compound, a polyisocyanate compound, and other monomers and a polymerization initiator as necessary are added.
  • a compound having a structure derived from a dye in an organic solvent and having a group that reacts with a polyisocyanate compound is polymerized, and water, optionally a neutralizer, an emulsifier (surfactant), and a chain extender are added.
  • Emulsifying and chain-extending the polymer and then appropriately removing the organic solvent to obtain an aqueous dispersion of the dye polymer
  • An organic solvent solution of a first prepolymer having an isocyanate group at the terminal obtained by reacting a compound having a structure derived from a dye and having a group that reacts with a polyisocyanate compound and the polyisocyanate compound
  • An organic solvent solution of a second prepolymer having a dispersible structure and having an isocyanate group at the terminal optionally mixed with an emulsifier (surfactant) and an organic solvent, water, optionally an emulsifier (surfactant) And the like, and an organic solvent is appropriately removed to obtain an aqueous dispersion of a dye polymer.
  • the ink of the present invention contains a pigment.
  • the pigment is not particularly limited, Carbon black, Aniline black, C. I. Pigment Yellow 3, 12, 53, 55, 74, 81, 83, 93, 94, 95, 97, 98, 100, 101, 104, 108, 109, 110, 117, 120, 128, 138, 153, 155, 180, 185, C. I. Pigment Red 112, 114, 122, 123, 146, 149, 166, 168, 170, 172, 177, 178, 179, 185, 190, 193, 202, 206, 209, 219, C. I. Pigment violet 19, 23, C. I. Pigment orange 36, 43, 64, C. I. Pigment Blue 15, 15: 1, 15: 2, 15: 3, 15: 4, 15: 6, 16, 17: 1, 56, 60, 63, C. I. Pigment Green 36 It is preferably at least one selected from
  • an aqueous pigment dispersion (also referred to as a “pigment aqueous dispersion”) in which a pigment is dispersed in water using a dispersant may be used in preparing the ink.
  • the pigment aqueous dispersion the pigment dispersion described in JP2012-7148A can be used.
  • a self-dispersing pigment can also be used.
  • Self-dispersing pigments that can be used include self-dispersing carbon black CAB-O-JET 200, 300 (above, manufactured by Cabot), BONJET CW-1 (500 ⁇ mol / g as a carboxy group), CW-2 ( Commercially available products such as carboxy group (470 ⁇ mol / g) (manufactured by Orient Chemical Co., Ltd.), Tokai Carbon Co., Ltd. Aqua-Black 162 (carboxyl group: about 800 ⁇ mol / g), and the like.
  • a pigment can be used individually or in mixture of 2 or more types in arbitrary ratios.
  • the dye polymer can also be used as a dispersant for dispersing the pigment in water.
  • the dye polymer present as a dispersant around the pigment is not the “aqueous dispersion of dye polymer” in the present invention. That is, the “dye polymer aqueous dispersion” in the present invention does not contain a pigment.
  • the ink of the present invention includes a pigment dispersion containing a pigment and a dye polymer that exists as a dispersant around the pigment, even when a dye polymer is used as the pigment dispersant. And an aqueous dispersion of the polymer.
  • An ink containing a pigment dispersion that does not contain an aqueous dispersion of a dye polymer but includes a pigment and a dye polymer that exists as a dispersant around the pigment is a heat treatment step in inkjet printing, and the dye polymer is converted into a pigment by melting the dye polymer. May peel off and the pigment may bleed out.
  • the aqueous organic solvent preferably has a water solubility of 10 g / 100 g-H 2 O or more at 25 ° C., more preferably 20 g / 100 g-H 2 O or more, and is miscible with water at an arbitrary ratio. Is particularly preferred.
  • the aqueous organic solvent include alcohol solvents, amide solvents, and nitrile solvents.
  • the content of the aqueous organic solvent in the dye polymer aqueous dispersion is preferably 5 to 50% by mass, more preferably 5 to 40% by mass, and particularly preferably 10 to 30% by mass. This range is preferable because the stability of the aqueous dispersion and the ejection stability as an inkjet ink can be imparted.
  • the ink of the present invention may contain a cross-linking agent for the purpose of improving the friction resistance or washing fastness of the colored fabric.
  • a cross-linking agent for the purpose of improving the friction resistance or washing fastness of the colored fabric.
  • the crosslinking agent include blocked isocyanate crosslinking agents (for example, Meikanate CX, TP-10, DM-35HC, SU-268A, etc., all manufactured by Meisei Kogyo Co., Ltd., trade names), and polyfunctional epoxy crosslinking agents (for example, , Denacor EX-313, 314, 322, 411, etc., all manufactured by Nagase ChemteX Corporation, trade names).
  • the ink of the present invention contains at least a water dispersion of a dye polymer and a pigment. That is, the ink of the present invention is a dispersion in which a dye polymer and a pigment are dispersed in a liquid containing water.
  • the dye polymer is in the form of particles in the ink of the present invention, and the preferred average particle size of the particulate dye polymer is the same as described above.
  • the content of the dye polymer in the ink of the present invention is preferably from 0.1 to 20% by mass, more preferably from 1 to 15% by mass, and even more preferably from 3 to 12% by mass.
  • the pigment content in the ink of the present invention is preferably 0.5 to 30% by mass, more preferably 1.0 to 15% by mass.
  • the printing density is preferably increased, and if it is 30% by mass or less, the viscosity of the ink is increased or the structural property is hardly generated in the viscosity characteristic. This is preferable because of excellent discharge stability.
  • the water content in the ink for ink jet textile printing of the present invention is preferably 20 to 95% by mass, and more preferably 50 to 90% by mass.
  • the method for preparing the ink of the present invention is not particularly limited.
  • the ink can be prepared by mixing an aqueous dispersion of a dye polymer, an aqueous dispersion of a pigment, and, if necessary, water or other components. .
  • the ink of the present invention can use a pH adjusting agent for the purpose of adjusting the pH.
  • a pH adjuster neutralizers, such as an organic base and an inorganic alkali, can be used, for example.
  • the storage stability of the ink can be improved by adjusting the pH of the ink.
  • the pH adjusting agent is preferably added so that the pH of the ink is 5 to 12, and more preferably added so that the pH is 5 to 9.
  • the ink of the present invention may further contain an aqueous dispersion of a water-insoluble polymer having no structure derived from a dye, in addition to the aqueous dispersion of a polymer having a structure derived from the dye and the pigment.
  • an aqueous dispersion of a water-insoluble polymer that does not have a structure derived from a dye in the ink of the present invention the dye polymer and / or the pigment can be firmly fixed to the fabric in inkjet printing.
  • the water-insoluble polymer is a polymer that is dispersed as particles in water at 25 ° C.
  • the average particle size (MV) of the water dispersion of the water-insoluble polymer is preferably 50 to 500 nm, preferably 20 to 500 nm, and more preferably 30 to 300 nm. If the polymer is dissolved in water, the polymer is not present as particles in water.
  • the water-insoluble polymer that does not have a structure derived from a dye is a polymer that does not have a structure derived from a dye in the molecule, and the “structure derived from a dye” is as described above.
  • the water-insoluble polymer having no structure derived from a dye is preferably a colorless polymer.
  • An aqueous dispersion of a water-insoluble polymer not having a structure derived from a dye contains at least water and a water-insoluble polymer not having a structure derived from a dye, and water having no structure derived from a dye.
  • the insoluble polymer is dispersed in water.
  • the water-insoluble polymer which does not have the structure derived from a dye is a component different from the polymer dispersing agent which can be used as a dispersing agent.
  • a water-insoluble polymer that does not have a structure derived from a dye exists by being dispersed alone in the ink, while a polymer dispersant is dispersed in a mixture with an aqueous dispersion of a dye polymer in the ink.
  • the water-insoluble polymer having no structure derived from a dye is preferably polyurethane, polyester, acrylic polymer, styrene-butadiene copolymer, or polyvinyl chloride.
  • the water-insoluble polymer having no structure derived from the dye may be used alone or in combination of two or more.
  • a water-insoluble polymer having no structure derived from a dye may be synthesized by a known method, or a commercially available product may be used.
  • polyurethane that can be used as a water-insoluble polymer that does not have a structure derived from a dye
  • polyurethane that can be used as a water-insoluble polymer that does not have a structure derived from a dye
  • the WBR series, Meisei Chemical Industry Co., Ltd. pass call, Enomoto Kasei Co., Ltd. Neorez series, etc. are mentioned.
  • Specific examples of the polyester that can be used as a water-insoluble polymer that does not have a structure derived from a dye include Toyobo Co., Ltd. vylonal, Takamatsu Yushi Co., Ltd. pesresin, and the like.
  • acrylic polymer that can be used as a water-insoluble polymer that does not have a structure derived from a dye
  • examples of the acrylic polymer that can be used as a water-insoluble polymer that does not have a structure derived from a dye include styrene / acrylic resin from Nippon Synthetic Chemical Co., Ltd., Movinyl series, and Lovene series from Mallard Creek Polymers. Styrene / acrylic resin, acrylic resin, and urethane / acrylic resin.
  • examples of the styrene-butadiene copolymer that can be used as a water-insoluble polymer having no structure derived from a dye include the Loveven series manufactured by Mallard Creek Polymers, and Nipol Lx421 manufactured by Nippon Zeon Co., Ltd.
  • Specific examples of polyvinyl chloride that can be used as a water-insoluble polymer that does not have a structure derived from a dye include vinibran manufactured by Nissin Chemical Industry Co.,
  • the water-insoluble polymer that does not have a structure derived from a dye is preferably melted at a heat treatment temperature or lower as in the above-described dye polymer.
  • a water dispersion of a water-insoluble polymer having no structure derived from a dye melts at a temperature lower than the heat treatment temperature, whereby the dye polymer and / or the pigment can be firmly fixed on the fabric. Since the heat treatment step is preferably performed at 100 to 200 ° C., the water-insoluble polymer having no structure derived from the dye is preferably melted at 200 ° C.
  • the Tg (glass transition temperature) of the water-insoluble polymer having no structure derived from the dye is preferably 200 ° C. or less, more preferably 180 ° C. or less, and further preferably 150 ° C. or less.
  • the Tg of a water-insoluble polymer having no structure derived from a dye can be measured by DSC (differential scanning calorimetry). From the reason of maintaining a good texture of the colored fabric when the ink of the present invention is used for inkjet printing, it is even more preferable that the Tg of the water-insoluble polymer having no structure derived from the dye is 150 ° C. or less. It is particularly preferably 120 ° C. or less, and most preferably less than 100 ° C. The lower the Tg of the water-insoluble polymer that does not have a structure derived from a dye, the softer the resulting film, the better the texture of the colored cloth.
  • the content of the water-insoluble polymer having no structure derived from the dye in the aqueous dispersion of the water-insoluble polymer having no structure derived from the dye is preferably 0.1 to 40% by mass, more preferably The content is 1 to 30% by mass, and particularly preferably 1 to 25% by mass.
  • the water content in the aqueous dispersion of the water-insoluble polymer having no structure derived from the dye is preferably 40 to 95% by mass, more preferably 50 to 90% by mass.
  • the ink of the present invention contains an aqueous dispersion of a water-insoluble polymer that does not have a structure derived from a dye
  • the aqueous dispersion of a water-insoluble polymer that does not have a structure derived from a dye in the ink of the present invention is preferably from 0.01 to 20% by weight, more preferably from 0.1 to 15% by weight.
  • the water-insoluble polymer and dye having no structure derived from the dye except that the structure derived from the dye does not have a preferable range of Tg is the above range.
  • the detailed description of the aqueous dispersion of the water-insoluble polymer having no derived structure is the same as that described above for the dye polymer and the aqueous dispersion of the dye polymer.
  • the ink of the present invention may contain other components other than those described above.
  • Other components include, for example, colorants other than the above dye polymers and pigments, organic solvents, surfactants, fluorescent brighteners, surface tension modifiers, antifoaming agents, drying inhibitors, lubricants, thickeners, Examples include ultraviolet absorbers, anti-fading agents, antistatic agents, matting agents, antioxidants, specific resistance adjusting agents, rust inhibitors, inorganic pigments, anti-reducing agents, antiseptics, antifungal agents, and chelating agents.
  • the surface tension of the ink is preferably adjusted to 20 mN / m to 70 mN / m, and more preferably adjusted to 25 mN / m to 60 mN / m. preferable.
  • the viscosity of the ink is preferably adjusted to 40 mPa ⁇ s or less, more preferably adjusted to 30 mPa ⁇ s or less, and adjusted to 20 mPa ⁇ s or less. It is particularly preferred. Viscosity is measured using an E-type rotational viscometer, controlled at 25 ° C.
  • Surface tension and viscosity are various additives such as viscosity modifiers, surface tension modifiers, specific resistance modifiers, film modifiers, UV absorbers, antioxidants, antifading agents, antifungal agents, and rust inhibitors. It can be adjusted by adding a dispersant, a surfactant and the like.
  • the color of the ink of the present invention is not particularly limited. For example, yellow ink, cyan ink, magenta ink, and black ink are preferable.
  • the ink of the present invention is a black ink, it is preferable because it is excellent in the effect of tightening other colors.
  • high density black ink has been demanded in the textile industry. Dark black is in demand because it has the effect of producing a high-class feeling and the effect of tightening other colors.
  • printing unlike printing on paper, which is a substrate that does not transmit light, it is difficult to print at a high density because the object to be printed is a fabric (particularly a woven fabric) that is a substrate that transmits light.
  • the density can be improved by devising an image receiving layer such as coated paper.
  • an image receiving layer such as coated paper.
  • it can be dyed to dark black by sufficiently dyeing it using a large amount of colored glue, but in ink jet printing, the amount of droplet ejection is limited, and it is difficult to express dark black. There's a problem.
  • the ink jet textile printing method of the present invention is an ink jet textile printing method having a step of printing the ink of the present invention on a fabric by an ink jet method, and there are the following two preferred embodiments.
  • 1st aspect The inkjet printing method which has the process of printing the ink of this invention directly on a fabric by an inkjet system.
  • Second aspect A pretreatment step in which an aqueous pretreatment liquid containing a flocculant is applied to a fabric to obtain a pretreated fabric, and the ink of the present invention is directly printed on the fabric pretreated by an inkjet method.
  • An ink jet textile printing method comprising the step of:
  • “direct printing” on a fabric by an ink jet method does not require a transfer step, and does not require a step of directly printing ink on a fabric and applying a printing paste. Is both directly printed on the fabric.
  • the ink-jet textile printing method of the present invention produces an effect of simple workability without producing waste materials such as waste water and transfer paper.
  • the pretreatment step in the second aspect is a step of obtaining a pretreated fabric by applying an aqueous pretreatment liquid containing a flocculant to the fabric.
  • the method for applying the aqueous pretreatment liquid to the fabric is not particularly limited, and examples thereof include a coating method, a padding method, an ink jet method, a spray method, and a screen printing method.
  • the flocculant contained in the aqueous pretreatment liquid is not particularly limited as long as it has an action of aggregating the dye polymer, but is at least one selected from organic acids, polyvalent metal salts, and cationic compounds. It is preferable.
  • the flocculant is a cationic compound or a polyvalent metal salt and the dye polymer has an anionic group (preferably an acid group)
  • the dye polymer has an anionic group (preferably an acid group)
  • a high-concentration colored cloth is obtained by printing with the ink jet printing method. be able to.
  • the pre-treated cationic compound or polyvalent metal salt stays on the fabric surface as a result of agglomeration at the moment of contact with the ink containing the dye polymer having an anionic group, resulting in the surface. It is thought that the amount of the dye polymer present increases and the concentration can be increased.
  • the flocculant is a cationic compound.
  • the polyvalent metal salt is a compound composed of a divalent or higher valent metal ion and an anion. Specifically, calcium chloride, calcium nitrate, calcium sulfate, calcium acetate, calcium hydroxide, calcium carbonate, magnesium chloride, magnesium acetate, magnesium sulfate, magnesium carbonate, barium sulfate, barium chloride, zinc sulfide, zinc carbonate, copper nitrate Etc.
  • the cationic compound is not particularly limited, and may be a low molecular compound or a high molecular compound.
  • the low molecular weight cationic compound include (2-hydroxyethyl) trimethylammonium chloride, benzoylcholine chloride, benzyltriethylammonium chloride, trimethylacetohydrazide ammonium chloride, 1-butyl-1-methylpyrrolidinium chloride, 3- Examples thereof include hydroxy-4- (trimethylammonio) butyrate hydrochloride, glycidyltrimethylammonium chloride, L-carnitine hydrochloride and the like.
  • high molecular weight cationic compound examples include water-soluble and positively active compounds such as polyallylamine or derivatives thereof, amine-epihalohydrin copolymers, or other quaternary ammonium salt type cationic polymers. Examples include charged cationic polymers. In some cases, a water-dispersible cationic polymer can be used.
  • a flocculant may be used individually by 1 type and may be used together 2 or more types.
  • the aqueous pretreatment liquid may contain, for example, a surfactant, a resin and the like in addition to water and an aqueous organic solvent.
  • the ink jet textile printing method of the present invention is further integrated with the fiber by further adding a heat treatment step, so that the dye polymer is fused to the fiber of the fabric, and further imparts friction resistance and the like.
  • the ink jet textile printing method of the present invention preferably further includes a heat treatment step.
  • a heat treatment step by performing a heat treatment step after printing on the fabric, the dye polymer particles can be melted (or softened) and the adhesion to the fibers can be improved (that is, heat-treated for melt dyeing). Can do).
  • the colored fabric is preferably dried and then heat treated for the purpose of melt dyeing, usually at 100 to 250 ° C., more preferably at 100 ° C. to 200 ° C., particularly preferably at 120 ° C. to 200 ° C.
  • the heat treatment time is preferably 30 seconds to 3 minutes.
  • a reactive group for example, a blocked isocyanate group
  • a crosslinking agent for example, a blocked isocyanate crosslinking agent or a polyfunctional epoxy crosslinking agent
  • a crosslinking reaction using a reactive group introduced into the polymer (for example, a blocked isocyanate group) or a crosslinking agent used in combination as an additive (for example, a blocked isocyanate crosslinking agent or a polyfunctional epoxy crosslinking agent).
  • the fabric colored by the inkjet printing method of the present invention is excellent in fastness (friction resistance). However, if necessary, the fabric can be fastened by padding the entire surface with a post-treatment agent (if necessary). In particular, it is possible to obtain a colored cloth having further improved friction resistance.
  • Post-treatment agents for the purpose of softening include cationic surfactants, anionic surfactants, nonionic surfactants, dimethyl silicone oil, amino silicone oil, carboxy modified silicone oil, hydroxy modified silicone oil, fatty acid , Fatty acid amide, mineral oil, vegetable oil, animal oil, plasticizer and the like.
  • a post-treatment agent for improving the smoothness of the colored fabric surface metal soap, paraffin wax, carnauba wax, microstalline wax, dimethyl silicone oil, amino silicone oil, carboxy modified silicone oil, hydroxy modified silicone oil, etc. Is mentioned.
  • these post-treatment agents are emulsified, thermally emulsified, or dispersed in a water solvent by stirring with a mixer, and a colored cloth is dipped, dried with mangles, dried and heat treated.
  • the friction resistance of a colored cloth can be improved by mix
  • the blending amount with respect to the post-treatment agent is preferably less than 5%, which is preferable because the softness of the texture of the colored fabric is not easily impaired.
  • the resin emulsion blended into the post-treatment agent as a sticking agent is not particularly limited, but is an acrylic ester resin emulsion, a urethane resin emulsion, an ethylene / vinyl acetate copolymer resin (EVA resin) emulsion, a silicone / acrylic resin emulsion.
  • Polyester resin emulsions and the like can be used, and in order to soften the texture of the colored cloth, the glass transition point of these resin emulsions is preferably 0 ° C. or lower.
  • Fabrics include synthetic fibers such as nylon, polyester and acrylonitrile, semi-synthetic fibers such as acetate and rayon, natural fibers such as cotton, silk and wool, and mixed fibers, woven fabrics, knitted fabrics, non-woven fabrics, etc. Is mentioned.
  • a pretreated fabric can also be used as the fabric.
  • the pretreatment liquid can be applied by a coating method, a padding method, an ink jet method, a spray method, a screen printing method, or the like.
  • the pretreatment liquid contains an aggregating agent that aggregates the dye polymer, and is preferably an aqueous solution.
  • flocculant examples include organic acids, polyvalent metal salts, and cationic compounds.
  • Apparel includes T-shirts, trainers, jerseys, pants, sweatsuits, dresses, blouses and the like. It is also suitable for bedding, handkerchiefs, cushion covers, curtains and the like.
  • the present invention also relates to an ink cartridge having the ink of the present invention and an ink jet printer having the ink of the present invention.
  • the present invention also relates to a colored fabric comprising a fabric, a dye polymer, and a pigment.
  • the fabric, the dye polymer, and the pigment are as described above.
  • the colored fabric of the present invention can be produced by the above-described inkjet printing method of the present invention.
  • NMP N-methylpyrrolidone
  • reaction solution A was obtained by reacting at 85 ° C. for 1 hour. Thereafter, V-601 (0.098 g) was added to the reaction solution A, and the mixture was further reacted at 85 ° C. for 2 hours to obtain a reaction solution B.
  • the reaction solution B is allowed to cool to 20 ° C., poured into 500 mL of water, crystals are precipitated, the crystals are filtered off, and the filtered crystals are dried in a 60 ° C. air dryer for one day to obtain a dye polymer.
  • a yellow powder of (Y-2-1) was obtained.
  • the yield of the dye polymer (Y-2-1) was 8.7 g.
  • the absorption maximum wavelength of the ultraviolet-visible absorption spectrum in a dilute solution of the dye polymer (Y-2-1) in tetrahydrofuran (THF) was 441 nm.
  • the weight average molecular weight (Mw) of the dye polymer (Y-2-1) measured by gel permeation chromatography (GPC) is 10,500 (in terms of polystyrene), and the dispersity (Mw / Mn) is 1.7. Met.
  • the weight average molecular weight of the dye polymer was calculated from gel permeation chromatography (GPC) measurement. Specifically, HLC-8220GPC (manufactured by Tosoh Corporation) was used.
  • the reaction solution was allowed to cool to 20 ° C., poured into 1 L of a 0.1 mol / L aqueous sodium hydroxide solution, 110 mL of 1 mol / L aqueous hydrochloric acid was added, and the mixture was filtered.
  • the obtained residue was added to 1 L of a 0.1 mol / L aqueous sodium hydroxide solution and stirred for 10 minutes.
  • 1 mol / L aqueous hydrochloric acid was added to adjust the pH to 5.2, followed by filtration.
  • the obtained residue was poured into 500 mL of water, stirred for 10 minutes, and then filtered.
  • the obtained residue was dried with a vacuum dryer at 60 ° C. for 3 hours to obtain a dye polymer (D-3-2).
  • a dye polymer aqueous dispersion (M1) was prepared in the same manner as the dye polymer aqueous dispersion (Y1) except that the dye polymer (D-3-2) was used in place of the dye polymer (Y-2-1). It was created.
  • the average particle diameter (MV) of the particulate dye polymer in the dye polymer aqueous dispersion (M1) was 130 nm.
  • a pigment dispersion (Bk2) was prepared in the same manner as the pigment dispersion (Y2) except that carbon black was used instead of Pigment Yellow 180.
  • Example 1 [Creation of yellow ink 1] The following components were mixed at 20 ° C., stirred for 15 minutes, and then filtered through a membrane filter (average pore size 0.8 ⁇ m) to prepare Yellow Ink 1.
  • Dye polymer aqueous dispersion (Y1) 2.0 g 1.0 g of pigment dispersion (Y2) Trimethylolpropane 0.056g 0.913g of ultrapure water 1,12-hexanediol 0.112g
  • Glycerin 0.560g
  • Surfynol 465 (trade name, manufactured by Nissin Chemical Industry) 0.056g
  • Yellow ink 1 is loaded into an ink cartridge as ink for ink-jet textile printing, and polyester fabric (polyester tropical (manufactured by Teijin Limited), Inc. Color dyeing, product code A02-01019), cotton fabric (with cotton broad sill, color dyeing, product code A02-01002), and polyester 65% cotton 35% blend (blend polyester 65 / cotton 35 broad)
  • polyester fabric polyyester tropical (manufactured by Teijin Limited), Inc. Color dyeing, product code A02-01019), cotton fabric (with cotton broad sill, color dyeing, product code A02-01002), and polyester 65% cotton 35% blend (blend polyester 65 / cotton 35 broad)
  • the images were printed on the product code A02-01030) manufactured by Color Dye Co., Ltd. and dried at 20 ° C. for 12 hours.
  • Inkjet printing Ink-jet printing was performed in the same manner as in Example 1 except that the yellow ink 2 was used in place of the yellow ink 1 to obtain a colored fabric.
  • Example 2 [Create Black Ink 1] The following components were mixed at 20 ° C., stirred for 15 minutes, and then filtered through a membrane filter (average pore size 0.8 ⁇ m) to prepare Black Ink 1.
  • Dye polymer aqueous dispersion (Bk1) 2.0 g Pigment dispersion (Bk2) 2.0g Trimethylolpropane 0.056g 0.913g of ultrapure water 1,12-hexanediol 0.112g Glycerin 0.560g Triethylene glycol monobutyl ether 0.112 g 2-pyrrolidone 0.168g Propylene glycol 0.028g Surfynol 465 (trade name, manufactured by Nissin Chemical Industry) 0.056g
  • Inkjet printing Ink-jet printing was performed in the same manner as in Example 1 except that the black ink 1 was used in place of the yellow ink 1 to obtain a colored fabric.
  • Inkjet printing Ink-jet printing was performed in the same manner as in Example 1 except that the black ink 2 was used in place of the yellow ink 1 to obtain a colored fabric.
  • Example 3 Similar to the preparation of yellow ink 1 except that the dye polymer aqueous dispersion (M1) was used instead of the dye polymer aqueous dispersion (Y1) and the pigment dispersion (M2) was used instead of the pigment dispersion (Y2). Thus, magenta ink 1 was prepared.
  • Inkjet printing Ink-jet printing was performed in the same manner as in Example 1 except that magenta ink 1 was used in place of yellow ink 1, and a colored fabric was obtained.
  • magenta ink 2 creation A magenta ink 2 was prepared in the same manner as the yellow ink 2 except that the pigment dispersion liquid (M2) was used instead of the pigment dispersion liquid (Y2).
  • Inkjet printing Ink-jet printing was performed in the same manner as in Example 1 except that magenta ink 2 was used in place of yellow ink 1, and a colored fabric was obtained.
  • Example 4 [Preparation of aqueous pretreatment liquid A (1) containing flocculant]
  • An aqueous pretreatment liquid A (1) was prepared by mixing and stirring the following components.
  • Cathiomaster PD-7 contains a cationic compound as a flocculant.
  • Cachio Master PD-7 (Yokkaichi Synthesis, solid content 50% by mass) 50g BYK348 (by Big Chemie Japan) 5g Glycerin 100g 845g of water
  • Polyester fabric (polyester tropical (manufactured by Teijin Ltd.), Color dye Co., Ltd., product code A02-01019), cotton fabric (with cotton broad sill, product of color dye Co., Ltd., product code A02-01002), and polyester 65% cotton 35% blend (mixed polyester 65 / cotton 35 broad, manufactured by Color Dyeing Co., Ltd., product code A02-01030) was applied with the aqueous pretreatment liquid A (1) prepared above by a padding method. It was squeezed at a squeezing rate of 70% and dried for 24 hours. The squeezing rate (%) represents the remaining amount (mass ratio) of the aqueous treatment liquid relative to the fabric after the cloth containing the aqueous treatment liquid is squeezed.
  • Inkjet printing process Ink-jet printing was carried out in the same manner as in Example 1 except that a pretreated fabric was used as a fabric to obtain a colored fabric.
  • Example 5 Ink-jet printing was performed in the same manner as in Example 4 except that the black ink 1 was used in place of the yellow ink 1 to obtain a colored cloth.
  • Example 6 Ink-jet printing was performed in the same manner as in Example 4 except that magenta ink 1 was used in place of yellow ink 1, and a colored fabric was obtained.
  • the prepolymer 6 is a polyurethane having a structure derived from a dye and a urethane bond and having an isocyanate group at the terminal.
  • the prepolymer 6 is a polyurethane having a structure derived from a dye and a urethane bond and having an isocyanate group at the terminal.
  • the prepolymer 4 is a polyurethane having a carboxyl group and a urethane bond and having an isocyanate group at the terminal.
  • the dye polymer contained in the dye polymer aqueous dispersion (ULx-7) was polyurethane / urea, and the average particle size (MV) thereof was 160 nm.
  • the dye polymer was found to be a polymer having a crosslinked structure because insoluble matter remained in any of dimethyl sulfoxide (DMSO), N-methylpyrrolidone (NMP), and tetrahydrofuran (THF). It was.
  • Example 7 [Preparation of cyan ink 1] The following components were mixed at 20 ° C., stirred for 15 minutes, and then filtered through a filter (average pore size 0.8 ⁇ m) to prepare cyan ink 1.
  • Dye polymer aqueous dispersion (ULx-7) 3.0 parts by weight Pigment dispersion (C2) 1.0 part by weight Ultrapure water 5.18 parts by weight Glycerin 0.60 parts by weight Triethylene glycol monobutyl ether 0.12 parts by weight Surfynol 465 (trade name, manufactured by Nissin Chemical Industry) 0.10 parts by mass
  • Q-2 was used directly in the next step.
  • 141 g of iminodiacetic acid manufactured by Tokyo Chemical Industry Co., Ltd.
  • 420 mL of triethylamine manufactured by Wako Pure Chemical Industries, Ltd.
  • 1.8 L of tetrahydrofuran manufactured by Wako Pure Chemical Industries, Ltd.
  • Q-2 was added to the flask, stirred for 30 minutes after the addition, and further stirred at 20 ° C. for 30 minutes. After stirring, 1.8 L of water was added, and the precipitate was collected by filtration to obtain Q-3.
  • the prepolymer 1 is a polyurethane having a structure derived from a dye and a urethane bond and having an isocyanate group at the terminal.
  • prepolymer 2 is a polyurethane having a carboxyl group and a urethane bond and having an isocyanate group at the terminal.
  • a mixed liquid of 35.6 parts by mass of pure water and 11.7 parts by mass of a 4% by mass aqueous sodium dodecyl sulfate solution was added, stirred for 12 minutes at 16000 rpm, and emulsified to obtain an emulsion. Thereafter, the obtained emulsion was distilled off under reduced pressure to remove the organic solvent. Thereafter, 2.8 parts by mass of a 10% by mass aqueous solution of UCAT SA102 (trade name, manufactured by San Apro Co., Ltd.) was added to the emulsified liquid, and pure water was added so that the solid concentration was 15% by mass. And prepolymer 1 and prepolymer 2 were reacted for 2 days.
  • aqueous dye polymer dispersion (ULx-8).
  • the final solid content concentration of the dye polymer aqueous dispersion (ULx-8) was 15% by mass.
  • the dye polymer contained in the dye polymer aqueous dispersion (ULx-8) was polyurethane / urea, and the average particle size thereof was 184 nm.
  • the dye polymer since the insoluble matter remained in any of DMSO, NMP, and THF, the dye polymer was found to be a polymer having a crosslinked structure.
  • Example 8 [Preparation of Yellow Ink 3] The following components were mixed at 20 ° C., stirred for 15 minutes, and then filtered through a filter (average pore size 0.8 ⁇ m) to prepare yellow ink 3.
  • Dye polymer aqueous dispersion (ULx-8) 3.0 parts by weight Pigment dispersion (Y2) 1.0 part by weight Ultrapure water 5.18 parts by weight
  • Glycerin 0.60 parts by weight
  • Triethylene glycol monobutyl ether 0.12 parts by weight
  • Surfynol 465 (trade name, manufactured by Nissin Chemical Industry) 0.10 parts by mass
  • Inkjet printing Ink-jet printing was performed in the same manner as in Example 1 except that the yellow ink 3 was used in place of the yellow ink 1 to obtain a colored fabric.
  • Example 9 Ink-jet printing was performed in the same manner as in Example 4 except that the yellow ink 3 was used in place of the yellow ink 1 to obtain a colored fabric.
  • Example 10 [Preparation of Yellow Ink 4] The following components were mixed at 20 ° C., stirred for 15 minutes, and then filtered through a filter (average pore size 0.8 ⁇ m) to prepare yellow ink 4.
  • Dye polymer aqueous dispersion (ULx-8) 3.0 parts by mass Pigment dispersion (Y2) 1.0 part by mass Nipol Lx421 (manufactured by Nippon Zeon Co., Ltd.) 0.80 parts by mass Ultrapure water 4.38 parts by mass Glycerin 0.60 parts by mass Triethylene glycol monobutyl ether 0.12 parts by mass Surfynol 465 (manufactured by Nissin Chemical Industry, trade name) 0.10 parts by mass
  • Nipol Lx421 is a dispersion containing an aqueous dispersion of a carboxyl-modified styrene / butadiene copolymer which is a water-insoluble polymer having no structure derived from a dye.
  • the average particle size of the aqueous dispersion is 100 nm and the solid content is 41% by mass.
  • Inkjet printing Ink-jet printing was performed in the same manner as in Example 1 except that the yellow ink 4 was used in place of the yellow ink 1 to obtain a colored fabric.
  • Example 11 Ink-jet printing was performed in the same manner as in Example 4 except that the yellow ink 4 was used in place of the yellow ink 1 to obtain a colored fabric.
  • Apparatus SHIMADZU Nexera X2 (manufactured by Shimadzu Corporation) Column: TSKgel ODS-120H (manufactured by Tosoh Corporation) Eluent: Liquid A) 1 L of water, 1 mL of trifluoroacetic acid B liquid) 1L of tetrahydrofuran, 1mL of trifluoroacetic acid Changed from A solution concentration 60% and B solution concentration 40% over 6 minutes to A solution concentration 0% and B solution concentration 100%, and then kept A solution concentration 0% and B solution concentration 100% for 2 minutes. .
  • Preparation of Prepolymer 5 in THF In a three-necked flask, isophorone diisocyanate 13.1 g, dimethylol butanoic acid 4.0 g, polycaprolactone diol (manufactured by Aldrich, average molecular weight 530) 6.4 g, trimethylol propane 0.5 g, THF 56.0 g, Neostan U-600 ( Nitto Kasei Kogyo Co., Ltd., trade name) 0.7 g was added and stirred at 75 ° C. for 4 hours. THF was added so that the final solid content concentration was 30% by mass to obtain a THF solution of prepolymer 5.
  • a black dye polymer aqueous dispersion (ULx-1).
  • the final solid content concentration of the dye polymer aqueous dispersion (ULx-1) was 15% by mass.
  • the dye polymer contained in the dye polymer aqueous dispersion (ULx-1) was polyurethane / urea, and the average particle size (MV) thereof was 95 nm.
  • the dye polymer since the insoluble matter remained in any of DMSO, NMP, and THF, the dye polymer was found to be a polymer having a crosslinked structure.
  • the obtained emulsion was distilled off under reduced pressure to remove the organic solvent. Thereafter, 1.8 g of a 10% by mass aqueous solution of UCAT SA102 (trade name, manufactured by San Apro Co., Ltd.) was added to the emulsion, and pure water was added so that the solid content concentration was 15% by mass. The reaction was held for a day. Thereafter, coarse particles were removed by filtration to obtain 40 g of a black dye polymer aqueous dispersion (ULx-2). The final solid content concentration of the dye polymer aqueous dispersion (ULx-2) was 15% by mass.
  • UCAT SA102 trade name, manufactured by San Apro Co., Ltd.
  • the dye polymer contained in the dye polymer aqueous dispersion (ULx-2) was polyurethane / urea, and the average particle size (MV) thereof was 115 nm. Moreover, since the insoluble matter remained in any of DMSO, NMP, and THF, the dye polymer was found to be a polymer having a crosslinked structure.
  • Example 12 [Preparation of Black Ink 3] The following components were mixed at 20 ° C., stirred for 15 minutes, and then filtered through a filter (average pore size 0.8 ⁇ m) to prepare black ink 3.
  • Dye polymer aqueous dispersion (ULx-1) 3.5 parts by weight Pigment dispersion (Bk2) 2.5 parts by weight Glycerin 0.4 parts by weight Diethylene glycol 0.3 parts by weight Surfynol 465 (manufactured by Nissin Chemical Industry, trade name) ) 0.1 parts by weight water 3.2 parts by weight
  • Example 13 [Preparation of Black Ink 4] The following components were mixed at 20 ° C., stirred for 15 minutes, and then filtered through a filter (average pore size 0.8 ⁇ m) to prepare black ink 4.
  • Dye polymer aqueous dispersion (ULx-2) 3.5 parts by weight Pigment dispersion (Bk2) 2.5 parts by weight Glycerin 0.4 parts by weight Diethylene glycol 0.3 parts by weight Surfynol 465 (manufactured by Nissin Chemical Industry, trade name) ) 0.1 parts by weight water 3.2 parts by weight
  • Example 14 [Preparation of Black Ink 5] The following components were mixed at 20 ° C., stirred for 15 minutes, and then filtered through a filter (average pore size 0.8 ⁇ m) to prepare black ink 5.
  • Dye-polymer aqueous dispersion (ULx-2) 6.0 parts by weight Pigment dispersion (Bk2) 0.5 parts by weight Glycerin 0.4 parts by weight Diethylene glycol 0.3 parts by weight Surfynol 465 (manufactured by Nissin Chemical Industry, trade name) ) 0.1 parts by weight water 2.7 parts by weight
  • Example 15 Ink-jet printing was performed in the same manner as in Example 4 except that the black ink 5 was used in place of the yellow ink 1 to obtain a colored fabric.
  • Example 16 [Preparation of Black Ink 6] The following components were mixed at 20 ° C., stirred for 15 minutes, and then filtered through a filter (average pore size 0.8 ⁇ m) to prepare black ink 6.
  • Dye polymer aqueous dispersion (ULx-2) 3.5 parts by weight Pigment dispersion (Bk2) 2.5 parts by weight WBR-2101 (manufactured by Taisei Fine Chemical Co., Ltd.) 1.0 part by weight Glycerin 0.4 part by weight Diethylene glycol 0.3 Parts by weight Surfynol 465 (manufactured by Nissin Chemical Industry Co., Ltd.) 0.1 parts by weight water 2.2 parts by weight
  • WBR-2101 is a dispersion containing an aqueous dispersion of polyurethane, which is a water-insoluble polymer having no structure derived from a dye, and the content of the aqueous dispersion of polyurethane is 25% by mass.
  • the average particle size (MV) of the body is 41 nm.
  • Example 17 Ink-jet printing was performed in the same manner as in Example 4 except that the black ink 6 was used in place of the yellow ink 1 to obtain a colored fabric.
  • the colored cloths obtained in Examples 1 to 17 and Comparative Examples 1 to 3 were evaluated as follows. In the evaluation of wet friction fastness and washing resistance, cotton cloth was used among the three kinds of cloth. -Image clarity: The sensory evaluation was performed visually. AA when 3 types of fabric are clear and dark, A when 3 types of fabric are clear, B when 2 types are clear, C when only 1 type is clear, and 4 when there is no clear image D Rated by stage. -Wet friction fastness: JIS (Japanese Industrial Standard) L-0849 (revised in 2013) Evaluation was made based on the Gakushin type friction test (class 5 method). The evaluation result of wet friction fastness shows that the larger the value, the better the fastness. Washing resistance: evaluated according to JIS L-0844 A-2 according to “JIS Handbook 31 Fiber” edited by Japanese Standards Association, published in 2015. Larger numbers indicate better wash resistance.
  • A As a color ink (magenta ink, yellow ink, and cyan ink), a commercially available pigment ink (manufactured by Fujifilm Imaging Colorant, product name Projet TX413) is used, and as the black ink, the above black inks 1 to 6 are used.
  • the image pattern for evaluation shown in FIG. 2 was printed on the cotton fabric, and sensory evaluation was performed visually. A case where the magenta, yellow and cyan color portions appear to be tightened is designated as A, and a portion where the magenta, yellow and cyan portions appear to be blurred is designated as B.
  • a method for creating an image pattern for evaluation is shown below.
  • black ink one kind selected from black inks 1 to 6 corresponding to the respective examples or comparative examples and the above-described color inks (magenta ink, yellow ink, and cyan ink) are loaded in an ink cartridge, and an ink jet printer 2 is printed on a cotton fabric (with cotton broad sill, manufactured by Color Dyeing Co., Ltd., product code A02-01002) using (Clario PX-045A manufactured by Seiko Epson Corporation). Dry at 20 ° C. for 12 hours.
  • a heat press manufactured by Asahi Textile Machinery Co., Ltd., trade name: desktop automatic flat press machine AF-54TEN type
  • B represents a portion printed in black using black ink
  • M represents a portion printed in magenta color using magenta ink
  • Y represents a portion printed in yellow color using yellow ink
  • C represents a portion printed in cyan using cyan ink.
  • the size of the black portion is 50 mm ⁇ 50 mm, and the size of the magenta, yellow, and cyan color portions is 5 mm ⁇ 5 mm, respectively.
  • the interval between the magenta portion and the yellow portion is 3 mm, and the interval between the yellow portion and the cyan portion is 3 mm.
  • the temperature was raised to 200 ° C. at 10 ° C./min, and it was confirmed whether or not it was melted at 200 ° C.
  • the dye polymer melted at 200 ° C.
  • the ink for inkjet printing of the example of the present invention gives a colored fabric having excellent image sharpness and friction fastness.
  • the ink jet textile printing method according to the embodiment of the present invention does not require a pretreatment process, and does not generate waste water and waste materials. Therefore, it is excellent in environmental load and has no problem in workability.
  • an ink that can provide a colored cloth excellent in image sharpness and fastness to wet friction, an ink jet printing method using the ink, an ink cartridge and an ink jet printer having the ink, and the colored cloth Can be provided.

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

Abstract

L'invention concerne : une encre pour impression sur tissu par jet d'encre qui contient une dispersion aqueuse d'un polymère de structure dérivée d'une teinture, et un pigment ; un procédé d'impression sur tissu par jet d'encre qui met en œuvre ladite encre pour impression sur tissu par jet d'encre ; une cartouche d'encre possédant ladite encre pour impression sur tissu par jet d'encre ; une imprimante à jet d'encre ; et un tissu coloré contenant le polymère de structure dérivée d'une teinture et le pigment. Plus précisément, l'invention permet de fournir une encre pour impression sur tissu par jet d'encre qui permet de fournir un tissu coloré excellent en termes de clarté d'image et de solidité au frottement à l'état humide ; un procédé d'impression sur tissu par jet d'encre qui met en œuvre ladite encre pour impression sur tissu par jet d'encre ; une cartouche d'encre possédant ladite encre pour impression sur tissu par jet d'encre ; une imprimante à jet d'encre ; et ledit tissu coloré.
PCT/JP2018/007846 2017-03-06 2018-03-01 Encre, procédé d'impression sur tissu par jet d'encre, cartouche d'encre, imprimante à jet d'encre, et tissu coloré WO2018163966A1 (fr)

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Publication number Priority date Publication date Assignee Title
WO2019078128A1 (fr) * 2017-10-17 2019-04-25 富士フイルム株式会社 Encre, procédé d'impression de textile par jet d'encre, cartouche d'encre, imprimante par jet d'encre, dispersion aqueuse, polyurée, polyuréthane, composé et textile coloré
EP3492652A4 (fr) * 2016-07-28 2019-08-07 FUJIFILM Corporation Procédé d'impression par jet d'encre, composition colorée, encre pour jet d'encre, cartouche d'encre, et polymère colorant

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JPH07119047A (ja) * 1993-10-18 1995-05-09 Toray Ind Inc インクジェット染色方法
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WO2016027881A1 (fr) * 2014-08-21 2016-02-25 株式会社ミマキエンジニアリング Imprimante à jet d'encre, procédé d'impression de colorant et encre
JP2016069656A (ja) * 2014-09-30 2016-05-09 富士フイルム株式会社 キサンテン骨格を有する化合物、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、インクジェットプリンタカートリッジ、インクジェット記録物、カラーフィルタ、カラートナー、転写用インク、及び捺染用着色組成物
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WO2018021158A1 (fr) * 2016-07-28 2018-02-01 富士フイルム株式会社 Procédé d'impression sur tissu à jet d'encre, composition colorée, encre pour jet d'encre, cartouche d'encre et polymère colorant
WO2018043414A1 (fr) * 2016-08-31 2018-03-08 富士フイルム株式会社 Procédé d'impression à jet d'encre sur tissu, procédé de fabrication de tissu coloré, et tissu coloré

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JPH06157899A (ja) * 1992-11-19 1994-06-07 Mitsuboshi Belting Ltd Ｒｉｍ工法廃材より再生した樹脂成形体の製造方法
JPH07119047A (ja) * 1993-10-18 1995-05-09 Toray Ind Inc インクジェット染色方法
JPH07138888A (ja) * 1993-11-15 1995-05-30 Canon Inc インクジェット捺染方法
JPH11116877A (ja) * 1997-07-31 1999-04-27 Xerox Corp 着色樹脂エマルション粒子を含むインク
JP2004516355A (ja) * 2000-12-20 2004-06-03 アベシア・リミテッド 着色した水消散性ポリウレタン
JP2006124704A (ja) * 2004-10-25 2006-05-18 Hewlett-Packard Development Co Lp 顔料成分及び染料成分を有する高分子着色剤並びに対応するインク組成物
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WO2016027881A1 (fr) * 2014-08-21 2016-02-25 株式会社ミマキエンジニアリング Imprimante à jet d'encre, procédé d'impression de colorant et encre
JP2016069656A (ja) * 2014-09-30 2016-05-09 富士フイルム株式会社 キサンテン骨格を有する化合物、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、インクジェットプリンタカートリッジ、インクジェット記録物、カラーフィルタ、カラートナー、転写用インク、及び捺染用着色組成物
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WO2018043414A1 (fr) * 2016-08-31 2018-03-08 富士フイルム株式会社 Procédé d'impression à jet d'encre sur tissu, procédé de fabrication de tissu coloré, et tissu coloré

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3492652A4 (fr) * 2016-07-28 2019-08-07 FUJIFILM Corporation Procédé d'impression par jet d'encre, composition colorée, encre pour jet d'encre, cartouche d'encre, et polymère colorant
WO2019078128A1 (fr) * 2017-10-17 2019-04-25 富士フイルム株式会社 Encre, procédé d'impression de textile par jet d'encre, cartouche d'encre, imprimante par jet d'encre, dispersion aqueuse, polyurée, polyuréthane, composé et textile coloré
JPWO2019078128A1 (ja) * 2017-10-17 2020-12-03 富士フイルム株式会社 インク、インクジェット捺染方法、インクカートリッジ、インクジェットプリンタ、水分散液、ポリウレア、ポリウレタン、化合物、及び着色布

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