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WO2004035691A1 - Composes de phtalocyanine pour impression a jet d'encre, compositions d'encres vertes a base d'eau contenant ces composes, et imprimes colores obtenus au moyen de ces composes - Google Patents

Composes de phtalocyanine pour impression a jet d'encre, compositions d'encres vertes a base d'eau contenant ces composes, et imprimes colores obtenus au moyen de ces composes Download PDF

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Publication number
WO2004035691A1
WO2004035691A1 PCT/JP2003/013269 JP0313269W WO2004035691A1 WO 2004035691 A1 WO2004035691 A1 WO 2004035691A1 JP 0313269 W JP0313269 W JP 0313269W WO 2004035691 A1 WO2004035691 A1 WO 2004035691A1
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Prior art keywords
ink jet
jet recording
water
group
compound
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PCT/JP2003/013269
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English (en)
Japanese (ja)
Inventor
Noriko Kajiura
Shinichi Namba
Original Assignee
Nippon Kayaku Kabushiki Kaisha
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Application filed by Nippon Kayaku Kabushiki Kaisha filed Critical Nippon Kayaku Kabushiki Kaisha
Priority to AU2003301420A priority Critical patent/AU2003301420A1/en
Publication of WO2004035691A1 publication Critical patent/WO2004035691A1/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
    • 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
    • C09B56/00—Azo dyes containing other chromophoric systems
    • C09B56/14—Phthalocyanine-azo dyes

Definitions

  • the present invention relates to a phthalocyanine compound for ink jet recording, an aqueous green ink composition containing the same, and a colored body obtained using the same.
  • the present invention provides a green pigment composition and an aqueous green ink composition containing a water-soluble cyanine compound, a mixture of a water-soluble phthalocyanine compound and a yellow dye, and a green ink composition useful for a recording method using an ink-jet printer. It relates to a colored body with high sharpness. Background art
  • a phthalocyanine compound (green dye) is described as a dye contained in an ink composition for one color filter.
  • a method for producing a green dye is described (for example, Japanese Patent Application Laid-Open No. 8-60052).
  • an ink composition for a color filter containing a phthalocyanine-based anionic water-soluble green dye is also described (for example, JP-A-9-1291240).
  • the ink composition is required to be stable for long-term storage, to have a high density of printed images, and to be excellent in fastness such as water resistance, light resistance and gas resistance. Furthermore, with the recent spread of digital cameras, the opportunity to print images at home has also increased. Discoloration of images due to oxidizing gas in the air when storing the resulting prints is also viewed as a problem. Disclosure of the invention
  • An object of the present invention is to provide a daline dye for ink jet recording which has a high solubility in water, has a hue and sharpness suitable for ink jet recording, and is more safe for humans, and an ink composition containing the same. Aim.
  • the present inventors have conducted intensive studies to solve the above-described problems, and as a result, have reached the present invention. That is, the present invention
  • Me represents Cu, Zn or Al
  • Pc represents a phthalocyanine residue.
  • Hi represents 0 to 3
  • 0 represents 0 to 2
  • a represents 1 to 4
  • + 3 + a is 4 or less.
  • B is the free acid form of formula (2)
  • R 2 is independently 1 H, 1 CH 3 , 1 COOH, — NHCO CH 3 , a halogen atom or an alkoxy group having 1 to 3 carbon atoms
  • R 3 is 1 CONH 2 , — CN Or one CH 2 SO 3 H
  • R 4 is an alkyl group having 1 to 4 carbon atoms, one (CH 2 ) n C ⁇ OH, one (CH 2 ) q S 03 H (q represents 1, 2 or 3) Or a hydroxyalkyl group having 1 to 3 carbon atoms, and n represents 0 to 2.
  • Sulfonic acid, carboxylic acid, and hydroxyl group are all represented in free acid form. Represents a compound residue.
  • a water-soluble phthalocyanine compound for ink jet recording represented by
  • R 3 is one CONH 2, or - a CH 2 S 0 3 H
  • R 4 is an alkyl group having 1 to carbon atoms 4
  • n represents each 0 or 1.
  • Me represents Cu
  • Pc represents a phthalocyanine residue.
  • a represents 1 to 2
  • ⁇ + a is 4 or less.
  • 3 one CONH 2, or represents an CH 2 S 0 3 H
  • R 4 represents an alkyl group having 1 to 4 carbon atoms
  • n represents 0 or 1.
  • the water-soluble phthalocyanine compound for ink jet recording according to (1) which is a compound represented by the formula (1):
  • an ink jet recording green composition comprising a mixture of a water-soluble phthalocyanine compound for inkjet recording and a yellow dye according to any one of (3),
  • R i and R 2 each independently represent 1 H, _CH 3 , 1 C ⁇ OH, 1 NHCO CH 3 , a halogen atom or an alkoxy group having 1 to 3 carbon atoms
  • R 3 represents 1 C ONH 2 , one CN or —CH 2 S 0 3 H
  • R 4 is an alkyl group having 1 to 4 carbon atoms, — (CH 2 ) q COOH, — (CH 2 ) q S 0 3 H (q is 1 , 2 or 3) or a hydroxyalkyl group having 1 to 3 carbon atoms
  • n represents 0 to 3
  • C represents a hydrogen atom, a substituent or a linking group, respectively.
  • R 3 one CONH 2, one CN or - a CH 2 S 0 3 H,; 4 is an alkyl group having a carbon number of 1 - 4, one (CH 2) QC_ ⁇ _OH one (CH 2 ) q S 0 3 H (q represents 1, 2 or 3) or a hydroxyalkyl group having 1 to 3 carbon atoms, n represents 0 to 3, C represents an amino group, an acetylamino group, -SO 2 H, or —SO 3 H, or a group represented by the following formula (7), (8) or (9) as a free acid]
  • X and Y each independently represent a chlorine atom, a substituted or unsubstituted amino group or a substituted or unsubstituted hydroxyl group.
  • D 2 is independently 1 H, 1 CH 3 , 1 COOH, —NHCOCH 3 , a halogen atom or an alkoxy group having 1 to 3 carbon atoms, and D 3 is 1 CONH 2 , 1 CN or —CH 2 S ⁇ 3 H
  • D 4 represents an alkyl group having 1 to 4 carbon atoms, — (CH 2 ) n C ⁇ OH, — (CH 2 ) q S 03 H (Q represents 1, 2 or 3), or 1 to 3 carbon atoms.
  • n 0 to 3, respectively.
  • the water-soluble phthalocyanine compound for inkjet recording according to any one of (1) to (3) or the ink jet recording according to any one of (5) to (7) As the pigment component, the water-soluble phthalocyanine compound for inkjet recording according to any one of (1) to (3) or the ink jet recording according to any one of (5) to (7).
  • An aqueous green ink composition for ink jet recording comprising a green composition, (9) a water-soluble phthalocyanine compound for ink jet recording according to any one of (1) to (3), (5)
  • Pc is a phthalocyanine residue, is 1 to 3, ⁇ is 1 to 4, ⁇ + ⁇ is 4 or less.
  • An aqueous green ink composition for ink jet recording comprising a water-soluble phthalocyanine compound as described in (16) or (17) as a dye component,
  • a green composition for ink jet recording comprising a mixture of the water-soluble phthalocyanine compound according to (16) or (17) and a yellow dye.
  • BEST MODE FOR CARRYING OUT THE INVENTION the present invention will be described in detail.
  • a sulfonic acid group, a hydroxyl group, and a carboxyl group are represented in a free acid form unless otherwise specified.
  • the water-soluble phthalocyanine compound for ink jet recording of the present invention will be described.
  • the phenol residue which may be substituted with a nitro group, a carboxy group, a nitrile group, or a hydroxyl group of A is, for example, a 0-nitrophenol residue, a m-nitrophenol residue.
  • examples of the halogen atom for R 1 R 2 include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.
  • examples of the alkoxy group having 1 to 3 carbon atoms include, for example, methoxy group and ethoxy group. Group, ⁇ -propoxy group and isopropoxy group.
  • alkyl group having 14 to 14 carbon atoms examples include a methyl group, an ethyl group, an ⁇ -propyl group, an isopropyl group, an ⁇ -butyl group, an isobutyl group, a sec-butyl group and a t-butyl group.
  • the bonding position of the azo group on the benzene ring is preferably 3-position relative to the bonding position of the phthalocyanine residue.
  • the water-soluble phthalocyanine compound for ink jet recording of the present invention is particularly preferably a compound represented by the above formula (10).
  • R ⁇ in Formula (2) for example R ⁇ is a hydrogen atom, R 2 is a hydrogen atom, R 3 is CONH 2 or one CH 2 S 0 3 H, with R 4 is n- butyl is there. Further, n is 1, and the bonding position of the sulfonic acid group on the benzene ring is preferably 4-position relative to the bonding position of the phthalocyanine residue.
  • the 4th position means that the position of the substituent on each benzene nucleus in CuPc is the 4, 4 ', 4 "or 4'" position of the following formula (11).
  • the yellow dye represented by the formula (5) which can be used in combination with the water-soluble phthalocyanine compound for ink jet recording of the present invention, if necessary, will be described.
  • the halogen atom of R i, R 2 include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.
  • the alkoxy group having 1 to 3 carbon atoms for example, a methoxy group Ethoxy group, n-propoxy group; and isopropoxy group.
  • Examples of the alkyl group having 1 to 4 carbon atoms for R 4 include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group and a t-butyl group.
  • Examples of C include an amino group, a sulfonic group, an acetylamino group, and the above formulas (7) to (9).
  • examples of the group that can be substituted for the amino group of X and Y include a hydroxyl group, a sulfonic group, and a phenyl group, and the phenyl group is a sulfonic acid group and an alkyl group. It may be replaced.
  • examples of the group which can be substituted with a hydroxyl group include an alkyl group.
  • Specific examples of the formulas (7), (8) and (9) include groups represented by the following formulas (10) to (16).
  • Preferred examples of the compounds represented by the formulas (5) and (6) include the compound Nos. 19 to 29 shown below.
  • the phthalocyanine compound in which the position of the group substituted on the benzene nucleus on the phthalocyanine nucleus is at the 4-position is the respective phthalocyanine compound.
  • a copper phthalocyanine having a sulfone group at the 4-position of the benzene nucleus on the mouth cyanine nucleus was produced, and the sulfonic acid was chlorided by a known method. It can be manufactured according to the manufacturing method described in (0 0 64) to (008 3) of the gazette.
  • Copper phthalocyanines having a sulfonate group at the 4-position of the benzene nucleus on each phthalocyanine nucleus are described in, for example, Japanese Patent Application Laid-Open No. 2000-30309 (0 0 10) to (0 0 11), (
  • 4-sulfophthalic acid or 4-sulfophthalic acid and anhydrous It is obtained by heating and reacting phthalic acid in a desired ratio in the presence of urea, a catalyst and a copper compound.
  • the reaction temperature is usually 150 to 290 ° C at normal pressure, preferably 170 to 270 ° C.
  • the reaction time varies depending on the reaction temperature, but is usually 1 to 8 hours.
  • the number of sulfone groups can be adjusted by changing the molar ratio of the reaction between 4-sulfophthalic acid and phthalic anhydride.
  • the pyridazo compounds represented by the formulas (5) and (6) can be produced, for example, as follows. That is, when 1 C in the formula (5) or (6) is a substituent, it is obtained by diazotizing an aromatic amine and then coupling it to a hydroxypyridone. Each substituent may be introduced before or after subjecting to the diazotization coupling reaction, but it is preferable to introduce each substituent before subjecting to the diazotization coupling reaction.
  • a water-soluble pyridazo compound into which the substituent is introduced as 1 C is used.
  • an amino group is introduced by using an aromatic amine having an acetylamino group as C in the formula, and hydrolyzing after diazotized coupling with the pyridone azo compound.
  • alkali hydroxide When X and Y are groups other than chlorine and both X and Y are hydroxyl groups, after condensing cyanuric chloride with the above-described water-soluble pyridone azo compound having an amino group introduced thereinto, alkali hydroxide is added. It is obtained by performing hydrolysis using When one of X and Y is a hydroxyl group, condensation of cyanuric chloride with HX or HY, and the above-mentioned water-soluble pyridone azo compound into which an amino group has been introduced, in any order, followed by hydrolysis using alkali hydroxide Is obtained.
  • Y is a chlorine atom, cyanuric chloride and the above-described water-soluble pyridine group into which the above amino group has been introduced. It is obtained by condensing two equivalents of a lidazo compound.
  • Y is a group other than chlorine, it can be obtained by condensing cyanuric chloride with HY and two equivalents of the water-soluble pyridone azo compound into which the above amino group has been introduced in an arbitrary order.
  • the water-soluble pyridazole having two equivalents of cyanuric chloride, ethylenediamine and the amino group described above is introduced.
  • the compound is obtained by condensing two equivalents of the compound in an arbitrary order, followed by mild hydrolysis using an alkali hydroxide.
  • both Y are groups other than chlorine, 2 equivalents of cyanuric chloride, 2 equivalents of ethylenediamine, 2 equivalents of HY, and 2 equivalents of a water-soluble pyridazo compound into which the above-described amino group has been introduced are condensed in any order. It is obtained by doing.
  • HY for two equivalents may be the same or different.
  • both Y are groups other than chlorine and both Y are hydroxyl groups
  • two equivalents of cyanuric chloride and two equivalents of ethylenediamine and the above-described water-soluble pyridazo compound into which the amino group has been introduced are optionally added. After condensation in order, it can be obtained by carrying out strong hydrolysis using hydroxide hydroxide.
  • Two equivalents of the above-mentioned amino-group-introduced pyridone azo compound having an amino group may be the same or different. May be.
  • one C in the formula (5) or the formula (6) is a linking group
  • it can also be produced as follows. That is, it is obtained by diazotizing an aromatic diamine to condensed cyanuric chloride after condensing it, and coupling it to hydroxypyridones.
  • cyanuric chloride may be uncondensed cyanuric chloride or chloride after primary condensation. It may be cyanur or cyanuric chloride after secondary condensation.
  • the water-soluble phthalocyanine compound for ink jet recording of the present invention exists in the form of a free acid or a salt thereof.
  • the salt can be used as an alkali metal salt, an alkaline earth metal salt, an alkylamine salt, an alkanolamine salt or an ammonium salt.
  • alkali metal salts such as sodium salt, potassium salt, and lithium salt
  • alkanol salts such as monoethanolamine salt, diethanolamine salt, triethanolamine salt, monoisopropanolamine salt, diisopropanolamine salt, and triisopropanolamine salt. Luamine salts and ammonium salts.
  • sodium salt is added to the reaction solution obtained above, or a cake or a dried product dissolved in water, salted out, and filtered to obtain sodium salt as a wet cake, and the wet cake is again obtained.
  • hydrochloric acid is added to adjust the pH to 1-2, and the crystals obtained are filtered to obtain the free acid (or a part of it as a sodium salt).
  • the dye in the form of the free acid is dissolved or suspended in water, and a base corresponding to the target salt, for example, an amine or an alkali metal compound other than sodium, is added and dissolved to form a solution of each salt. can get.
  • the salts other than the sodium salt can be obtained by precipitating, filtering, and drying each salt by a conventional method.
  • these salts preferred are the lithium and sodium salts.
  • the mixing ratio of the phthalocyanine compound for inkjet recording of the present invention and the pyridone azo compound represented by the formula (5) or (6) is, for example, 100 to 5 for the phthalocyanine compound and 0 to 95 for the pyridonazo compound.
  • the yellow dye other than the pyridoneazo compounds represented by the formulas (5) and (6) is preferably a water-soluble yellow direct dye or reactive dye having a maximum absorption wavelength in the visible light region of 41 O nm or less.
  • direct dyes are preferred. Particularly preferred are I. Direc t Yellow 132, 120 and U2. These yellow dyes are used in the form of a free acid or a salt thereof. The salt exchange may be performed in the same manner as described above.
  • the mixing ratio of the phthalocyanine compound for inkjet recording of the present invention to the yellow dye other than the pyridoneazo compound represented by the formula (5) or (6) is, for example, 100 to 5 for the phthalocyanine compound and 0 for the yellow dye. ⁇ 95 (weight ratio).
  • the phthalocyanine compound is 80 to 40, and the yellow dye is 20 to 60 (weight ratio).
  • the ink jet recording green composition of the present invention is suitable for dyeing natural and synthetic fiber materials or blended products, and these ink jet recording green compositions are remarkably suitable for producing writing inks and recording liquids. ing.
  • the reaction liquid of the phthalocyanine compound for ink jet recording of the present invention and, if necessary, a yellow dye used together can be used directly for producing a recording ink composition. However, it can be isolated from the reaction solution, dried, for example, spray-dried, and then processed into an ink composition.
  • the recording ink composition of the final product usually contains 0.1 to 20% by weight, more preferably 1 to 5% by weight, and still more preferably 2 to 10% by weight of the green dye of the present invention in an aqueous solution.
  • the ink composition of the present invention may contain 0 to 30% by weight of a water-soluble organic solvent and 0 to 5% by weight of an ink preparation.
  • the aqueous green ink composition for inkjet recording of the present invention comprises a phthalocyanine compound alone, a mixture of a phthalocyanine compound and a pyridoneazo compound. Or a green dye consisting of a mixture of a phthalocyanine compound and a yellow dye dissolved in water or an aqueous solvent (water containing a water-soluble organic solvent).
  • water-soluble organic solvent examples include C 1, such as methanol, ethanol, n-propanol, isopropanol, n-butanol, isobutanol, sec-butanol, and tert-butanol.
  • Carboxylic acid amides such as C4 alkanol, N, N-dimethylformamide or N, N-dimethylacetamide, lactams such as 2-pyrrolidone, N-methyl-2-pyrrolidone, 1 Cyclic ureas such as 2,3-dimethylimidazolidine-1-one or 1,3-dimethylhexahydropyrimido-2-one, ketones such as acetone, methylethylketone, 2-methyl-2-hydroxypentane-one Or cyclic ethers such as keto alcohol, tetrahydrofuran, and dioxane, ethylene glycol, 1,2- or 1,3-propylene glycol, 1 2 — or 1,4 monobutylene glycol, 1,6 hexylene glycol, diethylene glycol, triethylene glycol, tetraethylene glycol, dipropylene glycol, thiodiglycol, polyethylene glycol, polypropylene glycol, etc.
  • C2-C6 Monomers, oligomers or polyalkylene glycols having alkylene units or polyols (triols) such as polyalkylene glycol or thioglycol, glycerin, hexane-1,2,6-triol, ethylene glycol monomethyl ether Or ethylene dalicol monoethyl ether, diethylene dalicol monomethyl ether or diethylene dalicol monoethyl ether, or triethylene daryl monomethyl ether or triethylene glycol monoethyl ether (C 1 -C 4) alkyl ethers of polyhydric alcohols such as ether, heptyl lactone or dimethyl sulfoxide.
  • triols such as polyalkylene glycol or thioglycol, glycerin, hexane-1,2,6-triol, ethylene glycol monomethyl ether Or ethylene dalicol monoethyl ether, diethylene dalicol monomethyl ether or
  • the water-soluble organic solvent preferred as the water-soluble organic solvent are 2-piperidone, N-methyl-1-pyrrolidone, mono-, di- or triethylene glycol, and dipropylene glycol, more preferably 2-pyrrolidone. Don, N-methyl-1-pyrrolidone and diethylenedalicol.
  • These water-soluble organic solvents are used alone or as a mixture.
  • the ink preparation agent include an antiseptic / antifungal agent, a pH adjusting agent, a chelating agent, an antibacterial agent, a water-soluble ultraviolet absorber, a water-soluble polymer compound, a dye dissolving agent, a surfactant and the like.
  • preservatives and fungicides include organic sulfur-based, organic nitrogen-sulfur-based, organic halogen-based, haloallyl sulfone'-based, eodopropagyl-based, N-octaloalkylthio-based, nitrile-based, pyridine-based, and 8-oxyquinoline-based , Benzothiazole, isothiazoline, dithiol, pyridinoxide, nitropropane, organotin, phenol, quaternary ammonium salt, triazine, thiadiazine, anilide, adamantane, dithiocarbamate And brominated indanone compounds, benzyl bromacetate compounds, and inorganic salt compounds.
  • Examples of the organic halogen-based compound include sodium pentachlorophenol, examples of the pyridine oxide-based compound include sodium 2-pyridinethiol-l-oxide, and examples of the inorganic salt-based compound include anhydrous sodium. Sodium acetate may be mentioned.
  • Examples of the isothiazoline-based compounds include 1,2-benzisothiazoline-3-one, 2-n-octyl-4 monoisothiazoline-3-one, and 5-chloro-2-methyl-4-isothiazoline-3.
  • any substance can be used as long as it can control the pH of the ink within the range of 8.0 to 11.0 without adversely affecting the prepared ink.
  • alkanolamines such as diethanolamine and triethanolamine
  • hydroxides of alkali metals such as lithium hydroxide, sodium hydroxide and potassium hydroxide, ammonium hydroxide, or lithium carbonate, sodium carbonate
  • alkali metal carbonates such as potassium carbonate
  • the chelating reagent include sodium ethylenediaminetetraacetate, sodium triacetate triacetate, sodium hydroxyethylethylendiaminetriacetate, sodium diethylenetriaminepentaacetate, ⁇ Sodium ramyldiacetate.
  • Examples of the protective agent include acid sulfite, sodium thiosulfate, ammonium thioglycolic acid nitrite, diisopropylammonium nitrite, erythritol tetranitrate, dicyclohexylammonium nitrite, and the like.
  • Examples of the water-soluble ultraviolet absorber include sulfonated benzophenone and sulfonated benzotriazole.
  • Examples of the water-soluble polymer compound include polyvinyl alcohol, a cellulose derivative, polyamine, and polyimine.
  • Examples of the dye dissolving agent include urea, ⁇ -force prolactam, ethylene carbonate and the like.
  • surfactant examples include an anionic surfactant, an amphoteric surfactant, a cationic surfactant, and a nonionic surfactant.
  • anionic surfactants include alkyl sulfocarbonates, ⁇ -olefin sulfonates, polyoxyethylene alkyl ether acetates, hydroxyamino acids and salts thereof, hydroxymethyltaurine salts, and alkyl sulfate polyoxylates.
  • the cationic surfactant include a 2-vinylpyridine derivative and a poly (vinylvinylpyridine) derivative.
  • amphoteric surfactants include betaine lauryl dimethylaminoacetate, 2-alkyl-hydroxypropyloxymethyl hydroxybetaine, coconut oil fatty acid amidopropyldimethylaminoacetate, and polyoctyl polyaminoethyl ester. There are lysine and other imidazoline derivatives.
  • nonionic surfactant examples include polyoxyethylene nonyl ether, polyoxyethylene octyl phenyl ether, polyoxyethylene dodecyl phenyl ether, polyoxyethylene octyl phenyl ether, polyoxyethylene octyl phenyl ether, polyoxyethylene oleyl ether, Ethers such as polyoxyethylene lauryl ether, polyoxyethylene alkyl ether, and polyoxyarylalkyl alkyl ether, poly Acid, polyoxyethylene oleate, polyoxyethylene distearate, sorbitan laurate, sorbitan monostearate, sorbitan monooleate, sorbitan sesquiolate, polyoxyethylene monooleate, polyoxyethylene Esters such as stearate, 2,4,7,9-tetramethyl-15-decine-14,7-diol, 3,6-dimethyl-4, one-year-old cutin-3,6-diol, 3,5-dimethyl
  • the aqueous green ink composition for ink jet recording of the present invention comprises a green dye comprising a phthalocyanine compound alone, a mixture of a phthalocyanine compound and a pyridoneazo compound, or a mixture of a phthalocyanine compound and a yellow dye, in water or the above aqueous solvent (water-soluble organic solvent). Solvent-containing water) together with the ink preparation agent and the like.
  • this aqueous green ink composition for ink jet recording is used as an ink for an ink jet printer
  • the content of a phthalocyanine compound or a pyridone azo compound, and the content of inorganic substances such as metal cation chlorides and sulfates as known yellow dyes. It is preferable to use one having a small amount, and the standard of the content is, for example, about 1% by weight or less in the dye.
  • desalting may be performed by a usual method such as a method using a reverse osmosis membrane.
  • each may be subjected to desalting treatment and then mixed, or may be mixed and then desalted. Is desirably mixed after mixing.
  • the order of dissolution is not particularly limited. It may be pre-dissolved in water or the above-mentioned aqueous solvent (water containing a water-soluble organic solvent), and then dissolved by adding an ink preparation, or after dissolving the green dye of the present invention in water, A solvent and an ink preparation may be added and dissolved.
  • aqueous solvent and an ink preparation may be added to a reaction solution of the green dye of the present invention or a solution that has been subjected to a desalination treatment using a reverse osmosis membrane to form an ink composition. May be manufactured.
  • the order of dissolving each drug is not particularly limited.
  • the water to be used is preferably an ion-exchanged water or a water with few impurities such as distilled water.
  • fine filtration may be performed using a membrane filter or the like to remove impurities, and when used as an ink for an ink jet printer, it is preferable to perform fine filtration.
  • the pore size of a filter for performing microfiltration is usually 1 micron to 0.1 micron, preferably 0.8 micron to 0.2 micron.
  • the recording ink composition containing the water-soluble phthalocyanine compound of the present invention is suitable for use in printing, copying, marking, writing, drafting, stamping, or a recording method, particularly an ink jet printing method.
  • a high-quality green print having good resistance to water, sunlight, ozone and friction is obtained.
  • the water-soluble phthalocyanine compound of the present invention may be further mixed with a well-known and commonly used dye such as yellow or cyan to obtain a desired green color tone.
  • the colored body of the present invention is colored with the above-mentioned compound of the present invention.
  • the material to be colored is not particularly limited, and examples thereof include, but are not limited to, paper, fiber and cloth (cellulose, nylon, wool, and the like), leather, and base materials for color filters.
  • a coloring method a method using an ink jet printer is optimal, but it can also be applied to, for example, a printing method such as a dip dyeing method, a printing method, and a screen printing method.
  • Examples of the recording material to which the ink jet recording method of the present invention can be applied include a sheet for transmitting information such as paper and a film, a fiber and leather.
  • the information transmission sheet is preferably a surface-treated sheet, specifically, a sheet provided with an ink receiving layer on these substrates.
  • the ink receiving layer is formed, for example, by impregnating or coating the above-mentioned base material with a cationic polymer, or by using inorganic fine particles capable of absorbing pigments such as porous silica, alumina sol or special ceramics in polyvinyl alcohol or polyvinyl pyrrolidone.
  • Etc. hydrophilic It is provided by coating on the surface of the base material together with the hydrophilic polymer.
  • a sheet provided with such an ink receiving layer is usually called a special ink jet paper (film) or a glossy paper (film), such as a pictorico (manufactured by Asahi Glass Co., Ltd.), a color BJ paper, a color BJ photo film sheet. , Professional Photo Paper (both from Canon Inc.), Color Image Jet Paper (from Sharp Corp.), PM Photo Paper, Super Fine Dedicated Glossy Film (all from Epson Corp.) , And Pictafine (manufactured by Hitachi Maxell, Ltd.). Of course, it can also be used for plain paper.
  • the aqueous green ink composition for ink jet recording of the present invention can be used in combination with a yellow ink composition, a magenta ink composition, a cyan ink composition and, if necessary, a black ink composition.
  • the ink composition of each color is poured into each container, and this container is set (loaded) at a predetermined position of an ink jet printer, similarly to the container containing the aqueous green ink composition for ink jet recording of the present invention. , used. ''
  • a container containing the above ink composition is set at a predetermined position of an ink jet printer, and recording is performed on the recording material by an ordinary method.
  • the ink jet printer include a piezo printer using mechanical vibration and a bubble jet (registered trademark) printer using bubbles generated by heating.
  • the ink jet recording green ink composition of the present invention has a sharp dull color, and particularly has a high sharp hue on glossy ink jet paper. It is also very safe for humans. When used with other yellow and cyan inks, it is possible to produce a wide visible color tone that cannot be obtained with the green color resulting from the mixture of normal cyan ink and yellow ink. .
  • the green ink composition for ink jet recording according to the present invention does not precipitate or separate during storage. Further, when the green ink composition for ink jet recording according to the present invention is used in ink jet printing, the ejector (ink head) is not blocked.
  • the green ink composition for ink jet recording according to the present invention does not change its physical properties even under constant recirculation for a relatively long time by a continuous ink jet printer or intermittent use by an on-demand ink jet printer. .
  • Example 2
  • the mixing ratio is Compound No. 1940 parts to Compound No. 160 parts.
  • Example 3 The phthalocyanine compound represented by Compound No. 1 obtained in Example 1 and Compound No. 20 (synthesized according to Reference Example 2) were mixed to obtain a green dye composition.
  • the mixing ratio was Compound No. 160 to Compound N 0.2 140.
  • C.I.DirecctYellow1332 is 30 for compound No.170.
  • C. I. Direct B 1 u which is widely used as a cyan dye for ink jet recording instead of the mixture obtained in the examples for comparison Except for mixing 2.5 parts of e199 with 2.5 parts of C.I.D irect Yellow 13 which is widely used as yellow dye for ink jet recording, and toning it. An ink was prepared and subjected to inkjet recording in the same manner as in Example 6, and the recorded image was evaluated.
  • the mixing ratio was selected to be 50:50, where the hue of the recorded image was close to that of the example.
  • Table 2 shows the results of the hues of the Mitsuzawa paper (two types) of Example 6, Example 7, Example 8, Example 9, Example 10, and Comparative Example 1.
  • Example 6 phthalocyanine compound
  • Examples 7 to 9 mixture of phthalocyanine compound and pyridoneazo compound
  • Example 10 mixture of phthalocyanine compound and yellow direct dye
  • Table 3 shows the results of hues of the plain papers of Example 6, Example 7, Example 8, Example 9, Example 10 and Comparative Example 1.
  • Example 6 phthalocyanine compound
  • Examples 7 to 9 mixture of phthalocyanine compound and pyridoneazo compound
  • Example 10 mixture of phthalocyanine compound and yellow direct dye
  • Example 6 has higher ozone resistance than Comparative Example 1. It can be seen that Example 9 has stronger light resistance and ozone resistance than Comparative Example 1.
  • the phthalocyanine compound for ink jet recording of the present invention the mixture of the phthalocyanine compound and the pyridoneazo compound, or the green ink using the phthalocyanine compound and the yellow dye have a very sharp hue. It can be seen that this is a very excellent green color ink with high ozone fastness.
  • the crystals are separated by filtration, washed with 300 parts of ⁇ 0% methanol aqueous solution and dried, and a total of sulfone groups are added at the 4th position (4, 4 ′, 4 ′′, 4 ′′ ′′) of each benzene nucleus. 4 2. 9 parts of sulfo copper phthalocyanine having 4 were obtained as blue crystals.
  • a 5% aqueous sodium hydroxide solution was added at a liquid temperature of 5 ° C or lower while adding ice; After stirring under the same conditions for 1 hour, heat to 25 ° C, further stir at pH 8 for 1 hour, heat to 35 ° C, further stir at pH 8 for 1 hour, heat to 60 ° C, Stir for 1 hour.
  • Sodium chloride is gradually added to the completely dissolved reaction solution until crystals precipitate, and the same amount of sodium chloride is added.
  • the crystals are filtered, dried and dried to obtain a compound of No. 30 (benzene nucleus of phthalocyanine nucleus).
  • Compound having a substituent bonded to the 4-position) (Maximum absorption wavelength in water: 4 16 nm, 634 nm) 10.4 parts were obtained.
  • Example 11 The compound obtained in Example 11 was mixed with the compound of No. 20 (synthesized according to Reference Example 2) to obtain a green dye composition (maximum absorption wavelength in water: 421 nm, 634 nm). .
  • the mixing ratio is 50 for the compound of No. 30 and 50 for the compound of No. 20.
  • Example 11 The compound of No. 30 obtained in Example 11 and C. I. Direct Yellow 1332 represented by compound (02) were mixed with each other to give a green dye composition (maximum in water). Absorption wavelengths of 407 nm and 634 nm) were obtained.
  • the mixing ratio of the compound of No. 30 is 60, and the mixing ratio of C. I. Direcct Ye1 ow 132 is 40.
  • Example 14 Using the compounds or compositions obtained in Examples 11, 12, and 13, the aqueous ink compositions for ink jet recording were obtained by the method according to the above-mentioned (A) ink preparation. The test using the compound obtained in Example 11 was performed in Example 14 and the test using the composition obtained in Example 12 was performed using the mixture obtained in Example 15 and Example 13. Example 16 is performed. (B) Inkjet printer Printing was performed in the same manner as described in Lint, and the hue was evaluated in the same manner as described in (C) Evaluation of recorded image. Example 14, Example 15 and Example
  • Table 5 shows the results of hues on 16 glossy papers (2 types), and Table 6 shows the results of hues on plain paper. Table 5
  • the phthalocyanine compound for ink jet recording of the present invention is characterized by being excellent in water solubility and having good filterability on a membrane filter in the process of producing an ink composition. Further, the ink composition of the present invention using this compound does not have crystal precipitation, physical property change, color change or the like after storage for a long time, and has good storage stability.
  • Printed matter using the ink composition of the present invention as a Dary ink for ink jet recording has an ideal green hue without selecting a media (paper, film, etc.), and has been conventionally used for ink jet recording. It is possible to reproduce green with higher clarity than to reproduce green with yellow and cyan ink, and to reproduce the hue of a color image faithfully on paper.
  • the darry of the present invention When the ink composition is used together with yellow and cyan, an ink jet recording excellent in light resistance, ozone resistance and the like can be performed. Therefore, the water-soluble phthalocyanine compound for ink jet recording of the present invention is extremely useful as a dye for green ink for ink jet recording.

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

Abstract

Cette invention se rapporte à des composés de phtalocyanine hydrosolubles pour impression à jet d'encre qui ont une teinte très claire les rendant appropriés pour une impression à jet d'encre, qui permettent d'obtenir des imprimés d'une excellente solidité et qui ont une excellente durée de conservation, ces composés étant représentés par la formule générale (1), où B représente un groupe pyridoneazoanilino représenté par la formule générale (2) ; et les autres symboles sont chacun définis dans les pièces descriptives de la demande.
PCT/JP2003/013269 2002-10-18 2003-10-16 Composes de phtalocyanine pour impression a jet d'encre, compositions d'encres vertes a base d'eau contenant ces composes, et imprimes colores obtenus au moyen de ces composes WO2004035691A1 (fr)

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AU2003301420A AU2003301420A1 (en) 2002-10-18 2003-10-16 Phthalocyanine compounds for ink-jet recording, water-base green ink compositions containing the compounds, and colored prints made by using the same

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JP2002304885 2002-10-18
JP2002-304885 2002-10-18
JP2003052676 2003-02-28
JP2003-52676 2003-02-28

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009068513A3 (fr) * 2007-11-26 2010-01-14 Basf Se Procédé de nuance perfectionné
WO2016197234A1 (fr) 2015-06-11 2016-12-15 National Research Council Of Canada Préparation de films de cuivre a conductivité élevée

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
TWI842668B (zh) 2017-02-08 2024-05-21 加拿大國家研究委員會 具低黏度與低加工溫度之銀分子油墨
EP3580284B1 (fr) 2017-02-08 2023-10-25 National Research Council of Canada Encre moléculaire imprimable

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JPH0860052A (ja) * 1994-08-18 1996-03-05 Nippon Kayaku Co Ltd インク組成物及びそれを用いて作製するカラーフィルター
WO1999013009A1 (fr) * 1997-09-05 1999-03-18 Avecia Limited Composes de phtalocyanine utilises dans les encres pour impression a jet d'encre
EP0947859A1 (fr) * 1998-03-31 1999-10-06 Canon Kabushiki Kaisha Encre, filtre coloré, panneau à cristal liquide, ordinateur et procédé de fabrication de ce filtre
JP2002371210A (ja) * 2001-06-15 2002-12-26 Canon Inc インクおよびカラーフィルタとその製造方法

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Publication number Priority date Publication date Assignee Title
JPH0860052A (ja) * 1994-08-18 1996-03-05 Nippon Kayaku Co Ltd インク組成物及びそれを用いて作製するカラーフィルター
WO1999013009A1 (fr) * 1997-09-05 1999-03-18 Avecia Limited Composes de phtalocyanine utilises dans les encres pour impression a jet d'encre
EP0947859A1 (fr) * 1998-03-31 1999-10-06 Canon Kabushiki Kaisha Encre, filtre coloré, panneau à cristal liquide, ordinateur et procédé de fabrication de ce filtre
JP2002371210A (ja) * 2001-06-15 2002-12-26 Canon Inc インクおよびカラーフィルタとその製造方法

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009068513A3 (fr) * 2007-11-26 2010-01-14 Basf Se Procédé de nuance perfectionné
WO2009069077A3 (fr) * 2007-11-26 2010-01-21 The Procter & Gamble Company Compositions détergentes
CN101874079A (zh) * 2007-11-26 2010-10-27 宝洁公司 洗涤剂组合物
US8585784B2 (en) 2007-11-26 2013-11-19 Basf Se Shading process
CN101874079B (zh) * 2007-11-26 2015-11-25 宝洁公司 洗涤剂组合物
WO2016197234A1 (fr) 2015-06-11 2016-12-15 National Research Council Of Canada Préparation de films de cuivre a conductivité élevée
US10954406B2 (en) 2015-06-11 2021-03-23 National Research Council Of Canada Preparation of high conductivity copper films

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