WO2012008533A1 - Composé anthrapyridone ou sel de celui-ci, composition d'encre magenta et corps coloré - Google Patents

Composé anthrapyridone ou sel de celui-ci, composition d'encre magenta et corps coloré Download PDF

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Publication number
WO2012008533A1
WO2012008533A1 PCT/JP2011/066110 JP2011066110W WO2012008533A1 WO 2012008533 A1 WO2012008533 A1 WO 2012008533A1 JP 2011066110 W JP2011066110 W JP 2011066110W WO 2012008533 A1 WO2012008533 A1 WO 2012008533A1
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salt
ink composition
compound
ink
anthrapyridone compound
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PCT/JP2011/066110
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English (en)
Japanese (ja)
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松井　貴彦
順哉 柵木
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日本化薬株式会社
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Priority to JP2012524590A priority Critical patent/JPWO2012008533A1/ja
Publication of WO2012008533A1 publication Critical patent/WO2012008533A1/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
    • C09B5/00—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings
    • C09B5/02—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings the heterocyclic ring being only condensed in peri position
    • C09B5/14—Benz-azabenzanthrones (anthrapyridones)
    • 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

Definitions

  • the present invention relates to a novel anthrapyridone compound, a magenta ink composition containing the anthrapyridone compound as a pigment, and a colored product colored with these.
  • water-based inks in which water-soluble dyes are dissolved in water-based media have been used as inks such as fountain pens and felt-tip pens and inks for inkjet recording.
  • a water-soluble organic solvent is generally added to prevent clogging of the ink at the pen tip or the ink discharge nozzle.
  • a recording image with sufficient density is provided, the clogging of the pen tip and the nozzle does not occur, the drying property on the recording material is good, the bleeding is small, and the storage stability.
  • the recorded image is required to have fastness such as water resistance, light resistance and moisture resistance.
  • a method for recording image or character information on a color display of a computer in color by an ink jet printer generally four colors of yellow (Y), magenta (M), cyan (C), and black (K) are used.
  • each of Y, M, and C is as much as possible. It is desirable to have a hue close to that of the standard and to be clear.
  • the ink used for the ink is required to be stable for long-term storage, to have a high density of recorded images, and to be excellent in fastness such as water resistance, light resistance and gas resistance.
  • inkjet printers have been expanded from small OA printers to large industrial printers, and image robustness such as water resistance, moisture resistance, light resistance, and gas resistance is required more than ever. Yes.
  • organic or inorganic fine particles such as porous silica, cationic polymer, alumina sol, and special ceramics are coated on the surface of paper together with PVA resin and an ink receiving layer is provided on the recording material.
  • Moisture resistance refers to the resistance to the phenomenon that the dye on the recording material or in the recording material oozes around the colored image when the colored recording material is stored in a high humidity atmosphere. is there. When the bleeding of the pigment occurs, the image quality is remarkably deteriorated particularly in the high-definition image quality of the photographic tone.
  • ozone gas is considered to be a major causative substance that promotes the discoloration and fading phenomenon of ink jet recorded images. Since this discoloration phenomenon is characteristic of ink jet recorded images, it is resistant to ozone gas. Improvement is also an important issue.
  • magenta dyes used in water-based inkjet inks are xanthene dyes and azo dyes using H acid (1-amino-8-hydroxy-naphthalene-3,6-disulfonic acid).
  • the former is extremely excellent in hue and sharpness but very inferior in light resistance.
  • the latter is good in terms of hue and water resistance, but is inferior in light resistance and ozone gas resistance.
  • metal complexes of azo dyes aimed at improving light resistance have been proposed, but the sharpness and ozone gas resistance are extremely poor.
  • Magenta dyes with excellent clarity and light resistance have also been developed for azo dyes, but light resistance is still higher than cyan dyes represented by copper phthalocyanine dyes; yellow dyes, etc. Inferior level.
  • An object of the present invention is to provide a magenta dye (anthrapyridone compound) excellent in light resistance and an ink composition containing the same, particularly an ink composition for ink jet recording.
  • an anthrapyridone compound represented by a specific formula can solve the above-mentioned problems, and have completed the present invention.
  • anthrapyridone compound represented by the following formula (1) or a salt thereof [In Formula (1), R 1 represents a hydrogen atom, a C1-C5 alkyl group, a hydroxy C1-C5 alkyl group, a cyclohexyl group, or a cyano C1-C5 alkyl group, X is a group represented by the following formula (2). ] [In Formula (2), * Represents a binding site with two amide groups, R 2 and R 3 each independently represent a hydrogen atom or a C1-C5 alkyl group, R 2 and R 3 may combine to form a C5-C10 cycloalkylene ring with the two carbon atoms that they each replace. ]
  • R 2 and R 3 are each independently a hydrogen atom or a methyl group, or R 2 and R 3 are bonded to each other to form a cyclohexylene ring together with two carbon atoms to be substituted.
  • An anthrapyridone compound or a salt thereof 3) The anthrapyridone compound or a salt thereof according to 1) or 2) above, wherein R 1 is a hydrogen atom or a methyl group, 4) R 1 is a hydrogen atom or a methyl group, The anthrapyridone compound or the salt thereof according to 1), wherein R 2 and R 3 are hydrogen atoms; 5) An ink composition containing the anthrapyridone compound or a salt thereof according to any one of 1) to 4) as a pigment; 6) The ink composition according to 5) above, comprising water and a water-soluble organic solvent; 7) The ink composition according to 6), which is used for inkjet recording, 8) The content of the inorganic impurities contained in the
  • magenta dye compound
  • an ink composition containing the same particularly an ink composition for inkjet recording.
  • anthrapyridone “compound” of the present invention is simplified, including both of the “anthrapyridone” “compound or salt thereof”, unless otherwise specified. In the following, it means both “compound or salt thereof”.
  • the compound of the present invention is represented by the above formula (1).
  • examples of the C1-C5 alkyl group for R 1 include linear or branched ones. Specific examples include linear chains such as methyl, ethyl, n-propyl, n-butyl, and n-pentyl; branched chains such as isopropyl, isobutyl, sec-butyl, tert-butyl, isopentyl, and tert-pentyl. And the like. Preferable specific examples include methyl and ethyl, and methyl is particularly preferable.
  • the hydroxy C1-C5 alkyl group in R 1, include those hydroxy groups at any of the carbon atoms in the "C1-C5 alkyl group for R 1" are substituted, the hydroxy group and the nitrogen atom to the same carbon atom Those which are not substituted are preferred.
  • Specific examples include straight-chain C1-C5 alkyl moieties such as 2-hydroxyethyl, 2-hydroxypropyl, 3-hydroxypropyl, 3-hydroxybutyl, 4-hydroxybutyl, etc .; 1-hydroxy-2-propyl, C1-C5 alkyl moieties such as 1-hydroxy-2-butyl, 1-hydroxy-3-butyl, 2-hydroxy-3-pentyl, 2-hydroxy-1,1-dimethylethyl, etc. are branched; It is done.
  • a preferred specific example is 2-hydroxyethyl.
  • the cyano C1-C5 alkyl group for R 1, a cyano group to any carbon atom in the "C1-C5 alkyl group for R 1" can be exemplified those obtained by substituting.
  • Specific examples include straight-chain C1-C5 alkyl moieties such as 2-cyanoethyl, 2-cyanopropyl, 3-cyanopropyl, 3-cyanobutyl, 4-cyanobutyl, etc .; 1-cyano-2-propyl, 1-cyano And the like, wherein the C1-C5 alkyl moiety such as -2-butyl, 1-cyano-3-butyl, 2-cyano-3-pentyl, 2-cyano-1,1-dimethylethyl or the like is branched.
  • a preferred specific example is 2-cyanoethyl.
  • R 1 includes a hydrogen atom and a C1-C5 alkyl group (particularly methyl), and the latter is more preferable.
  • examples of the C1-C5 alkyl group for R 2 and R 3 include the same ones as described above for “C1-C5 alkyl group for R 1 ”, including preferable ones.
  • Examples of the C5-C10 cycloalkylene ring formed by combining R 2 and R 3 include cyclopentylene, cyclohexylene, cycloheptylene, and cyclooctylene.
  • the range of carbon number is usually C5-C10, preferably C5-C8, more preferably C5-C7, and particularly preferably C6.
  • a preferred specific example is cyclohexylene.
  • R 2 and R 3 include a hydrogen atom, a methyl group, or cyclohexylene in which R 2 and R 3 are bonded, more preferably a hydrogen atom and methyl, and particularly preferably a hydrogen atom.
  • R 1 has the same meaning as in formula (1)
  • R 2 and R 3 have the same meanings as in formula (2).
  • the salt of the compound of the above formula (1) is a salt formed with an inorganic or organic cation.
  • Preferred examples of the salt formed with the inorganic cation include alkali metal salts such as lithium salts, sodium salts, potassium salts; ammonium salts.
  • Preferred examples of the salt formed with the organic cation include a salt formed with quaternary ammonium represented by the following formula (3).
  • Z 1 to Z 4 each independently represent a hydrogen atom, an alkyl group, a hydroxyalkyl group, or a hydroxyalkoxyalkyl group, and at least one of Z 1 to Z 4 is other than a hydrogen atom It is the basis of.
  • Z 1 to Z 4 include C1-C6 alkyl groups (preferably C1-C4 alkyl groups) such as methyl, ethyl, and butyl; hydroxymethyl, 2-hydroxyethyl, 3-hydroxy Hydroxy C1-C6 alkyl groups (preferably hydroxy C1-C4 alkyl groups) such as propyl, 2-hydroxypropyl, 4-hydroxybutyl, 3-hydroxybutyl, 2-hydroxybutyl; hydroxyethoxymethyl, 2-hydroxyethoxyethyl, And hydroxy C1-C6 alkoxy C1-C6 alkyl groups (preferably hydroxy C1-C4 alkoxy C1-C4 alkyl groups) such as 3-hydroxyethoxypropyl, 3-hydroxyethoxybutyl and 2-hydroxyethoxybutyl.
  • C1-C6 alkyl groups preferably C1-C4 alkyl groups
  • salts formed with sodium, potassium, lithium, monoethanolamine, diethanolamine, triethanolamine, monoisopropanolamine, diisopropanolamine, triisopropanolamine, ammonium and the like are particularly preferred.
  • a method for producing the above salt is described.
  • the reaction solution, wet cake, or dry product containing the compound of the above formula (1) is dissolved in water, sodium chloride is added thereto for salting out, and the precipitated solid is separated by filtration to obtain the formula (1
  • the sodium salt of the compound can be obtained as a wet cake.
  • the obtained wet cake is dissolved again in water, and a solid acid obtained by adding a mineral acid such as hydrochloric acid to adjust the pH to strongly acidic (usually pH 1 or lower) is separated by filtration to obtain the formula (1).
  • the free acid of the compound represented by can be obtained as a wet cake.
  • each salt is formed by adding, for example, potassium hydroxide, lithium hydroxide, ammonia water, a quaternary ammonium salt corresponding to the above formula (3) or the like to the wet cake of the above free acid in water.
  • potassium salts, lithium salts, ammonium salts, quaternary ammonium salts and the like can also be obtained.
  • a wet cake of a mixture of a free acid and, for example, a sodium salt is used, and by adding potassium hydroxide, a mixed salt of the sodium salt and the potassium salt, or a sodium salt, a potassium salt, and a free acid. It is also possible to obtain a mixture or the like.
  • anthrapyridone compound represented by the above formula (1) of the present invention is shown in Table 1 below, but the present invention is not limited to these specific examples.
  • Table 1 No. 11 and no.
  • the “cyclohexylene ring” in 12 means a cyclohexylene ring formed together with two carbon atoms that R 2 and R 3 are bonded to each other in the above formula (1).
  • R 1 to R 3 have the same meaning as in the above formula (1).
  • the anthrapyridone compound of the present invention is produced, for example, by the following method. That is, a compound represented by the following formula (7) can be obtained by synthesizing according to a known method described in Patent Document 3 or the like, or according to the method.
  • aqueous solution containing the compound of formula (7) after neutralization it is preferable to use it for the next reaction after drying to obtain a solid containing the compound of formula (7).
  • an aprotic solvent for example, amides.
  • Z is a group represented by the following formula (10).
  • * represents a bonding site with two amide groups.
  • alkali metal carbonates eg, lithium carbonate, sodium carbonate, potassium carbonate, etc.
  • alkali metal hydroxides eg, lithium hydroxide, hydroxide
  • Sodium, potassium hydroxide, etc. are preferred.
  • the compound of the above formula (1) can be obtained in a free acid form or a salt form thereof.
  • the compound of the present invention can be used as a free acid or a salt thereof derived from, for example, an alkali metal salt, alkaline earth metal salt, alkylamine salt, alkanolamine salt, ammonium salt or the like.
  • the production method leading from various salts to the free acid, the production method leading from the free acid to various salts or various mixed salts, or a mixture of free acid and salt are as described above.
  • the compound represented by the above formula (1) is an inorganic impurity such as a metal cation chloride (such as sodium chloride) or sulfate (such as sodium sulfate) contained as an impurity in the total mass of the compound. It is preferable to use a small amount.
  • the standard of the content is, for example, about 1% by mass or less.
  • Examples of the method for producing the compound of the present invention with a small amount of inorganic impurities include a known method using a reverse osmosis membrane; a method of suspension purification using a C1-C4 alcohol (or the water-containing alcohol in some cases) and the like; or Examples include a known method using an anion and a cation exchange resin as appropriate;
  • the ink composition of the present invention is obtained by dissolving the compound represented by the above formula (1) as a pigment component and water or an aqueous solvent (water containing a water-soluble organic solvent described later).
  • a reaction liquid containing a compound represented by the above formula (1) can be used directly in the production of the ink composition.
  • the target product can be isolated from the reaction solution by, for example, crystallization; spray drying; and the like, dried, and then used in the ink composition.
  • the ink composition of the present invention usually contains 0.1 to 20% by mass, preferably 1 to 15% by mass, more preferably 2 to 10% by mass of the compound represented by the above formula (1).
  • the ink composition of the present invention may contain 0 to 30% by mass, preferably 5 to 20% by mass of a water-soluble organic solvent; 0 to 10% by mass of an ink preparation agent; It is preferable to contain.
  • water-soluble organic solvents examples include C1-C4 alkanols such as methanol, ethanol, n-propanol, isopropanol, n-butanol, isobutanol, sec-butanol, and tert-butanol ( Alcohol); carboxylic acid amides such as N, N-dimethylformamide and N, N-dimethylacetamide; 2-pyrrolidone, N-methyl-2-pyrrolidone, 1,3-dimethylimidazolidin-2-one, 1,3- Heterocyclic ureas such as dimethylhexahydropyrimido-2-one; ketones or ketoalcohols such as acetone, methyl ethyl ketone, 2-methyl-2-hydroxypentan-4-one; cyclic ethers such as tetrahydrofuran, dioxane; ethylene glycol 1,2- or 1,3-propylene
  • isopropanol preferred are isopropanol, glycerin, mono-, di- or triethylene glycol, dipropylene glycol, 2-pyrrolidone, N-methyl-2-pyrrolidone, butyl carbitol, and more preferred is isopropanol, glycerin. Butyl carbitol, 2-pyrrolidone, and N-methyl-2-pyrrolidone. These water-soluble organic solvents are used alone or in combination.
  • an ink preparation agent that can be used in preparing the ink composition of the present invention will be described.
  • the ink preparation agent include antiseptic / antifungal agents, pH adjusting agents, chelating reagents, rust preventive agents, water-soluble ultraviolet absorbers, water-soluble polymer compounds, dye solubilizers, and surfactants.
  • antiseptic / antifungal agents examples include organic sulfur, organic nitrogen sulfur, organic halogen, haloallylsulfone, iodopropargyl, N-haloalkylthio, nitrile, pyridine, 8-oxyquinoline, Benzothiazole, isothiazoline, dithiol, pyridine oxide, nitropropane, organotin, phenol, quaternary ammonium salt, triazine, thiadiazine, anilide, adamantane, dithiocarbamate, brominated indanone And benzyl bromacetate compounds.
  • An example of the organic halogen compound is sodium pentachlorophenol.
  • Examples of pyridine oxide compounds include sodium 2-pyridinethiol-1-oxide.
  • Examples of the isothiazoline compounds include 1,2-benzisothiazolin-3-one, 2-n-octyl-4-isothiazolin-3-one, 5-chloro-2-methyl-4-isothiazolin-3-one, 5 -Chloro-2-methyl-4-isothiazolin-3-one magnesium chloride, 5-chloro-2-methyl-4-isothiazolin-3-one calcium chloride, 2-methyl-4-isothiazolin-3-one calcium chloride, etc. Can be mentioned.
  • antiseptic / antifungal agents include sodium sorbate, sodium benzoate, anhydrous sodium acetate, trade names Proxel RTM GXL (S) and Proxel RTM XL-2 (S) manufactured by Avecia.
  • RTM means a registered trademark.
  • any substance can be used as long as it can control the pH of the ink in the range of 7.5 to 11.0 without adversely affecting the prepared ink.
  • alkanolamines such as diethanolamine and triethanolamine
  • alkali metal hydroxides such as lithium hydroxide, sodium hydroxide and potassium hydroxide
  • ammonium hydroxide ammonia water
  • lithium carbonate, sodium carbonate and potassium carbonate Alkali metal carbonates and the like.
  • chelating reagent examples include sodium ethylenediaminetetraacetate, sodium nitrilotriacetate, sodium hydroxyethylethylenediaminetriacetate, sodium diethylenetriaminepentaacetate, sodium uracil diacetate and the like.
  • rust preventive agent examples include acidic sulfite, sodium thiosulfate, ammonium thioglycolate, diisopropylammonium nitrite, pentaerythritol tetranitrate, dicyclohexylammonium nitrite and the like.
  • water-soluble ultraviolet absorber examples include sulfonated benzophenone and sulfonated benzotriazole.
  • water-soluble polymer compound examples include polyvinyl alcohol, cellulose derivatives, polyamines and polyimines.
  • dye solubilizer examples include urea, ⁇ -caprolactam, 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 sulfocarboxylates, ⁇ -olefin sulfonates, polyoxyethylene alkyl ether acetates, N-acyl amino acids and salts thereof, N-acyl methyl taurate, alkyl sulfate polyoxyalkyl ethers Sulfate, alkyl sulfate polyoxyethylene alkyl ether phosphate, rosin acid soap, castor oil sulfate ester, lauryl alcohol sulfate ester, alkylphenol type phosphate ester, alkyl type phosphate ester, alkyl aryl sulfonate, diethyl sulfosuccinate Salts, diethylhexylsylsulfosuccinate, dioctylsulfosuccinate and the like.
  • Examples of the cationic surfactant include 2-vinylpyridine derivatives and poly-4-vinylpyridine derivatives.
  • Amphoteric surfactants include lauryldimethylaminoacetic acid betaine, 2-alkyl-N-carboxymethyl-N-hydroxyethylimidazolinium betaine, coconut oil fatty acid amidopropyldimethylaminoacetic acid betaine, polyoctylpolyaminoethylglycine, imidazoline derivatives, etc. Is mentioned.
  • Nonionic surfactants include ethers such as polyoxyethylene nonylphenyl ether, polyoxyethylene octylphenyl ether, polyoxyethylene dodecylphenyl ether, polyoxyethylene oleyl ether, polyoxyethylene lauryl ether, polyoxyethylene alkyl ether; Ester systems such as polyoxyethylene oleate, polyoxyethylene distearate, sorbitan laurate, sorbitan monostearate, sorbitan monooleate, sorbitan sesquioleate, polyoxyethylene monooleate, polyoxyethylene stearate; 2,4,7,9-tetramethyl-5-decyne-4,7-diol, 3,6-dimethyl-4-octyne-3,6-diol, 3,5-dimethyl -1-hexyne-3-acetylene alcohol such as ol; and the like.
  • Other specific examples include trade name Surfinol RTM 104E, 104PG
  • the ink composition of the present invention is a water-based ink composition, wherein the compound represented by the formula (1) is added to water or the water-based solvent (water containing a water-soluble organic solvent), and the ink preparation agent as necessary. It can be manufactured by dissolving together with the above.
  • the order in which the components are dissolved is not particularly limited.
  • the compound of the present invention may be dissolved in water or the aqueous solvent in advance and the ink preparation agent may be added, or the aqueous solvent and the ink preparation agent may be added after the compound is dissolved in water. Further, the order may be different. Further, a reaction solution after completion of the final step in the synthesis reaction of the compound of the present invention; or an aqueous solution obtained by subjecting the compound of the present invention to a desalting treatment with a reverse osmosis membrane, a water-soluble organic solvent and an ink preparation. An ink composition may be produced by adding a preparation or the like.
  • the water used for the preparation of the ink composition is preferably water with few impurities such as ion exchange water and distilled water.
  • the ink composition thus prepared may be subjected to microfiltration using a membrane filter or the like as necessary to remove impurities.
  • microfiltration is preferably performed.
  • the pore diameter of the filter for performing microfiltration is usually 1 to 0.1 ⁇ m, preferably 0.8 to 0.2 ⁇ m.
  • Examples of the recording material (media) to which the ink jet recording method of the present invention can be applied include information transmission sheets such as paper and film, fibers, and leather.
  • the information transmission sheet is preferably a surface-treated sheet, specifically a substrate, for example, a sheet provided with an ink receiving layer on the recording material.
  • the ink-receiving layer may be impregnated or coated with a cationic polymer on a base material; porous white inorganic substance capable of adsorbing pigment in ink such as porous silica, alumina sol, special ceramics, polyvinyl alcohol, polyvinyl pyrrolidone, etc.
  • Such an ink-receiving layer is usually called inkjet paper (film), glossy paper (film), etc., for example, manufactured by Pictorico Co., Ltd., trade name Pictorico Pro; manufactured by Canon Inc., trade name professional Photo paper, super photo paper, matte photo paper; manufactured by Epson Corporation, trade name Krispia RTM , photo paper (gloss), photo matte paper, Superfine gloss film; Nippon Hewlett Packard Co., Ltd., trade name Advanced Photo Paper, premium plus photo paper, premium gloss film, photo paper; manufactured by Konica Minolta Photo Imaging Co., Ltd., trade name Photo-like QP; Of course, it is also possible to use an information transmission sheet not provided with an ink receiving layer, such as plain paper.
  • the discoloration caused by ozone gas in an image recorded on a recording material coated with a porous white inorganic substance on the surface is particularly large. Since the water-based magenta ink composition of the present invention is excellent in gas resistance including ozone gas, it is particularly effective when recording on such a recording material.
  • porous white inorganic substance examples include calcium carbonate, kaolin, talc, clay, diatomaceous earth, synthetic amorphous silica, aluminum silicate, magnesium silicate, calcium silicate, aluminum hydroxide, alumina, lithopone, zeolite, barium sulfate, calcium sulfate. , Titanium dioxide, zinc sulfide, zinc carbonate and the like.
  • a container containing the ink composition of the present invention is loaded in a predetermined position of an ink jet printer, and (small) droplets of the ink composition are ejected according to a recording signal to be recorded.
  • This is a method for recording on a material.
  • the ink composition of the present invention can be used alone as a magenta ink. For example, yellow, cyan, green, orange, blue (or violet), and black as necessary
  • a full-color recorded image can be obtained by using the ink composition of each color together.
  • the containers each containing an ink composition appropriately selected from the above-described colors may be loaded and used at predetermined positions of the ink jet printer.
  • Examples of the discharge method of the ink jet printer include a piezo method using mechanical vibration; a bubble jet (registered trademark) method using bubbles generated by heating; and the like.
  • the ink composition of the present invention can be used in any of these ejection methods.
  • the colored body of the present invention means a substance colored by the compound of the present invention or an ink composition containing the compound.
  • the substance to be colored is not particularly limited, and examples thereof include, but are not limited to, paper, fiber, cloth (cellulose, nylon, wool, etc.), leather, and a color filter substrate.
  • Examples of the coloring method include a dip dyeing method, a textile printing method, a printing method such as screen printing, and an ink jet recording method.
  • the colored body of the present invention is preferably a colored body colored by the inkjet recording method of the present invention.
  • the ink composition of the present invention has a clear magenta color, has a clear hue especially on glossy paper, and has high fastness of recorded images. Moreover, it is highly safe for humans.
  • the ink composition of the present invention can be used for various recording and printing applications such as printing, copying, marking, writing, drawing, stamping and the like, and is particularly suitably used as an ink for inkjet recording.
  • the ink composition of the present invention can be used for recording on plain paper, but has a high print density of an image recorded on special inkjet paper or glossy paper, and has a hue suitable for inkjet recording. Further, the recorded image has characteristics such as various fastnesses such as water resistance, light resistance, friction resistance and moisture resistance, in particular, extremely high light resistance.
  • the ink composition of the present invention does not precipitate or separate during storage, and has extremely high storage stability.
  • the compound of the present invention is excellent in water solubility, when the ink composition of the present invention containing the compound is used for ink jet recording, solid precipitation due to drying of the ink composition in the vicinity of the nozzle is very unlikely to occur.
  • the container (ink head) is not blocked.
  • the ink composition of the present invention exhibits a change in physical properties even in a use environment such as use in a continuous ink jet printer under constant recirculation for a relatively long time; intermittent use in an on-demand ink jet printer; Do not wake up.
  • Example 1 (Process 1) 97.5 parts of a wet cake of a compound of the following formula (11) obtained by following the method described in Patent Document 3 was added to 70 parts of water (purity 45.9% by diazotization value analysis), and further 25% water. An aqueous solution of pH 7 was obtained by adding an aqueous sodium oxide solution. The obtained aqueous solution was dried with a hot air dryer at 80 ° C. to obtain a solid containing the compound of the formula (11).
  • Example 2 (A) Preparation of ink By using the compound obtained in Example 1 as a pigment, the ink composition of the present invention having the composition shown in Table 2 below was prepared, and further filtered through a 0.45 ⁇ m membrane filter. An ink for inkjet recording was obtained. In preparing the ink, ion-exchanged water was used as water. The pH of the ink composition was adjusted with a 25% aqueous sodium hydroxide solution so that the pH was 8 to 10, and water was added so that the total amount was 100 parts. Preparation of an ink using the compound obtained in Example 1 is referred to as Example 2. In Table 2 below, as the “surfactant”, trade name Surfinol RTM 104PG50 manufactured by Nissin Chemical Co., Ltd. was used.
  • surfactant trade name Surfinol RTM 104PG50 manufactured by Nissin Chemical Co., Ltd. was used.
  • Comparative Example 1 A comparative ink was prepared in the same manner as in Example 2 except that the compound disclosed in Example 3 of Patent Document 1 was used instead of the compound obtained in Example 1. This is referred to as Comparative Example 1.
  • a comparative ink was prepared in the same manner as in Example 2 except that the compound disclosed in Example 1 of Patent Document 3 was used instead of the compound obtained in Example 1. This is referred to as Comparative Example 2.
  • a comparative ink was prepared in the same manner as in Example 2 except that the compound of Example 1 of Patent Document 4 was used instead of the compound obtained in Example 1. This is referred to as Comparative Example 3.
  • the structural formulas of the compounds used in Comparative Examples 1 to 3 are shown in the following formulas (12) to (14), respectively.
  • an image pattern was prepared so as to obtain a print density with several gradations, and a recorded matter was prepared.
  • the recorded material was used as a test piece, and the following xenon light resistance test was performed.
  • the reflection density of each test piece was measured for the two gradations closest to the reflection density D value of 1.0 and 0.5.
  • a colorimetry system (trade name: SpectroEye RTM , manufactured by X-Light) was used. Colorimetry was performed under the conditions of a density standard of DIN, a viewing angle of 2 degrees, and a light source of D65. The test method of the light resistance test and the evaluation method of the test result are described below.
  • the examples show excellent results over the glossy papers at both the D value of 1.0 and the D value of 0.5 compared to the comparative examples, and are extremely useful as magenta dyes for ink jet recording. .
  • the anthrapyridone compound of the present invention and an ink composition containing the compound are suitably used for magenta inks for various recordings such as writing utensils, particularly for inkjet recording.

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  • 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)
  • Ink Jet (AREA)

Abstract

L'invention porte sur un composé anthrapyridone ou sur un sel de celui-ci, représenté par la formule (1) ci-après, comme pigment magenta qui a une teinte nette appropriée pour l'impression par jet d'encre et qui permet d'obtenir un imprimé dont la solidité de couleur, telle que la résistance à la lumière, et la stabilité au stockage sont excellentes. L'invention porte également sur une composition d'encre contenant ledit composé anthrapyridone ou sel de celui-ci comme pigment. Dans la formule (1), R1 représente un atome d'hydrogène, C1 à C5 représentent chacun un groupe alkyle ou autre, et X représente un groupe représenté par la formule (2) ci-après. Dans la formule (2), R2 et R3 représentent chacun un atome d'hydrogène ou les groupes alkyle en C1 à C5 ou autre, R2 et R3 sont reliés et peuvent chacun former des noyaux cycloalkylène en C5 à C10 avec deux atomes de carbone substitués.
PCT/JP2011/066110 2010-07-14 2011-07-14 Composé anthrapyridone ou sel de celui-ci, composition d'encre magenta et corps coloré WO2012008533A1 (fr)

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JP2012524590A JPWO2012008533A1 (ja) 2010-07-14 2011-07-14 アントラピリドン化合物又はその塩、マゼンタインク組成物及び着色体

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JP2010-159445 2010-07-14
JP2010159445 2010-07-14

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WO2012008533A1 true WO2012008533A1 (fr) 2012-01-19

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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2006083330A (ja) * 2004-09-17 2006-03-30 Konica Minolta Holdings Inc インクセットとそれを用いた画像形成方法
JP2008280467A (ja) * 2007-05-11 2008-11-20 Nippon Kayaku Co Ltd 水溶性アントラピリドン化合物又はその塩、インク組成物及び着色体
JP2010006969A (ja) * 2008-06-27 2010-01-14 Nippon Kayaku Co Ltd アントラピリドン化合物又はその塩、そのアントラピリドン化合物を含有するマゼンタインク組成物及び着色体
JP2010116565A (ja) * 2009-12-18 2010-05-27 Seiko Epson Corp インクセット、インクカートリッジ、インクジェット記録方法及び記録物

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2006083330A (ja) * 2004-09-17 2006-03-30 Konica Minolta Holdings Inc インクセットとそれを用いた画像形成方法
JP2008280467A (ja) * 2007-05-11 2008-11-20 Nippon Kayaku Co Ltd 水溶性アントラピリドン化合物又はその塩、インク組成物及び着色体
JP2010006969A (ja) * 2008-06-27 2010-01-14 Nippon Kayaku Co Ltd アントラピリドン化合物又はその塩、そのアントラピリドン化合物を含有するマゼンタインク組成物及び着色体
JP2010116565A (ja) * 2009-12-18 2010-05-27 Seiko Epson Corp インクセット、インクカートリッジ、インクジェット記録方法及び記録物

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