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WO2012050061A1 - Colorant porphyrazine, son procédé de fabrication, composition d'encre et corps coloré - Google Patents

Colorant porphyrazine, son procédé de fabrication, composition d'encre et corps coloré Download PDF

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Publication number
WO2012050061A1
WO2012050061A1 PCT/JP2011/073223 JP2011073223W WO2012050061A1 WO 2012050061 A1 WO2012050061 A1 WO 2012050061A1 JP 2011073223 W JP2011073223 W JP 2011073223W WO 2012050061 A1 WO2012050061 A1 WO 2012050061A1
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group
formula
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Japanese (ja)
Inventor
米田　孝
知樹 藤田
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Nippon Kayaku Co Ltd
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Nippon Kayaku Co Ltd
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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
    • C09D11/328—Inkjet printing inks characterised by colouring agents characterised by dyes
    • 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
    • C09B47/00—Porphines; Azaporphines
    • C09B47/04—Phthalocyanines abbreviation: Pc
    • C09B47/08—Preparation from other phthalocyanine compounds, e.g. cobaltphthalocyanineamine complex
    • C09B47/24—Obtaining compounds having —COOH or —SO3H radicals, or derivatives thereof, directly bound to the phthalocyanine radical
    • C09B47/26—Amide radicals
    • 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
    • B41M5/50—Recording sheets characterised by the coating used to improve ink, dye or pigment receptivity, e.g. for ink-jet or thermal dye transfer recording
    • B41M5/52—Macromolecular coatings
    • B41M5/5218—Macromolecular coatings characterised by inorganic additives, e.g. pigments, clays

Definitions

  • the present invention relates to a porphyrazine coloring matter, a method for producing the same, an ink composition containing the same, an ink jet recording method using the ink composition, and a colored body.
  • the coloring matter used in the ink for ink jet recording dyes and pigments are generally used.
  • the water-soluble dye has various durability, that is, light resistance, gas resistance (NOx, SOx, ozone, etc., especially resistance to ozone gas), moisture resistance, water resistance, etc.
  • the performance required for the dye used in the ink for ink jet recording is good solubility in water or an organic solvent containing water; high density recording is possible.
  • no bronzing (phenomenon) occurs; good hue; good fixability to recording materials and low bleeding; excellent ink storage stability; no toxicity; Can be obtained at low cost; and the like.
  • Typical water-soluble cyan dyes used in cyan ink for ink jet recording are phthalocyanine dyes and triphenylmethane dyes.
  • Typical phthalocyanine dyes reported and used most widely include phthalocyanine derivatives disclosed in the following patent documents.
  • a cyan dye that satisfies all the above-mentioned qualities and can be manufactured at low cost has not been obtained yet. For this reason, it has not yet fully satisfied the demands of the market.
  • the present invention provides a porphyrazine coloring matter that is excellent in ozone resistance and is suitable for ink jet recording that hardly causes bronzing even if the coloring matter concentration in the ink is increased, a method for producing the same, and an ink composition containing the same. Is an issue.
  • the present inventors have studied various porphyrazine dyes in detail, and have found that a specific dye represented by the following formula (1) can solve the above problems, and have completed the present invention. That is, the present invention relates to the following 1) to 12).
  • E represents an alkylene group
  • R 1 represents an alkyl group
  • X is an anilino group having at least one sulfo group, and further comprises, as a substituent, a carboxy group; a phosphate group; a hydroxy group; an alkoxy group; an alkylcarbonylamino group; a ureido group; a nitro group; It may have a group selected from the group.
  • Rings A to D represented by broken lines each independently represent a benzene ring or a heteroaromatic ring, the number of the heteroaromatic rings being an average value of 0.0 to 3.0, and the rest being benzene rings Yes
  • E represents an alkylene group
  • R 1 represents an alkyl group
  • X is an anilino group having at least one sulfo group, and further comprises, as a substituent, a carboxy group; a phosphate group; a hydroxy group; an alkoxy group; an alkylcarbonylamino group; a ureido group; a nitro group; It may have a group selected from the group.
  • b is an average value greater than 0.0 and less than 3.9
  • c is an average value of 0.1 or more and less than 4.0
  • And the sum of b and c is 1.0 or more and less than 4.0 on average.
  • Rings A to D represented by broken lines each independently represent a benzene ring or a heteroaromatic ring, the number of the heteroaromatic rings being an average value of 0.0 to 3.0, and the rest being benzene rings Yes
  • E represents an alkylene group
  • R 1 represents an alkyl group
  • X is an anilino group having at least one sulfo group, and further comprises, as a substituent, a carboxy group; a phosphate group; a hydroxy group; an alkoxy group; an alkylcarbonylamino group; a ureido group; a nitro group; It may have a group selected from the group.
  • b is an average value greater than 0.0 and less than 3.9; c is an average value of 0.1 or more and less than 4.0; And the sum of b and c is 1.0 or more and less than 4.0 on average. ] 3)
  • dye represented by following formula (1), or its salt.
  • Rings A to D represented by broken lines each independently represent a benzene ring or a heteroaromatic ring, the number of the heteroaromatic rings being an average value of 0.0 to 3.0, and the rest being benzene rings Yes
  • E represents an alkylene group
  • R 1 represents an alkyl group
  • X is an anilino group having at least one sulfo group, and further comprises, as a substituent, a carboxy group; a phosphate group; a hydroxy group; an alkoxy group; an alkylcarbonylamino group; a ureido group; a nitro group; It may have a group selected from the group.
  • b is an average value greater than 0.0 and less than 3.9
  • c is an average value of 0.1 or more and less than 4.0
  • And the sum of b and c is 1.0 or more and less than 4.0 on average.
  • a porphyrazine coloring matter suitable for ink jet recording which is excellent in ozone resistance and hardly causes bronzing even when the coloring matter concentration in the ink is increased, a method for producing the same, and an ink composition containing the same. can do.
  • dye of this invention or its salt is a mixture of the pigment
  • the heteroaromatic rings in rings A to D represented by broken lines are heteroaromatic rings having at least one nitrogen atom as a ring constituent atom, that is, nitrogen-containing heteroaromatic rings.
  • the number of nitrogen atoms is usually 1 to 2, preferably 1.
  • Specific examples include pyridine having one nitrogen atom; similarly two pyrazines, pyridazines and pyrimidines.
  • the condensed ring site with the porphyrazine ring in the heteroaromatic ring is not particularly limited, when the rings A to D are pyridine rings, the position of the nitrogen atom is the 1st position, the 2nd position and the 3rd position, or the 3rd position and the 4th position.
  • the ring is preferably condensed at the position, and the latter is particularly preferred.
  • the number of the heteroaromatic rings is an average value of generally greater than 0.0 and 3.0 or less, preferably 0.2 or more and 2.0 or less, more preferably 0.5 or more and 1.7 or less, and still more preferably It is the range of 0.7 or more and 1.5 or less.
  • the remaining rings A to D are benzene rings, and the number of benzene rings in the rings A to D is also generally an average value of 1.0 or more and less than 4.0, preferably 2.0 or more and 3.8 or less. More preferably, they are 2.3 or more and 3.5 or less, More preferably, they are 2.5 or more and 3.3 or less.
  • the number of the heteroaromatic ring is rounded off to the first digit after the second decimal place.
  • the former becomes 1.4 and the latter becomes 2.7
  • the sum of both is the sum of rings A to D. It becomes larger than 4.0.
  • the second decimal place on the heteroaromatic ring side is rounded down, and only the benzene ring side is rounded off to describe the former as 1.3 and the latter as 2.7.
  • b and c in formula (1) to be described later are also rounded off to the first digit by rounding off the second digit after the decimal point.
  • the second digit after the decimal point on the b side is rounded down. Only the c side is rounded off.
  • the alkylene group in E includes a linear, branched, or cyclic alkylene group, preferably a linear or cyclic group, and more preferably a linear chain.
  • the range of the carbon number in the alkylene is usually C2-C12, preferably C2-C6, more preferably C2-C4, and particularly preferably C2-C3.
  • linear chains such as ethylene, propylene, butylene, pentylene, hexylene, heptylene, octylene, nonylene, decylene, undecylene and dodecylene; branched chains such as 2-methylethylene; cyclopropylene diyl, 1 , 2- or 1,3-cyclopentylenediyl, cyclic cyclohexylenediyl such as 1,2-, 1,3-, 1,4- and the like; and the like.
  • examples of the alkyl group in R 1 include straight chain, branched chain, and cyclic groups, and straight chain or branched chain groups are preferable, and straight chain groups are more preferable. preferable.
  • the range of carbon number is usually C1-C6, preferably C1-C4, more preferably C1-C3. Specific examples include straight chain such as methyl, ethyl, n-propyl, n-butyl, n-pentyl and n-hexyl; branched chain such as isopropyl, isobutyl, sec-butyl, t-butyl, isopentyl and isohexyl.
  • Cyclic groups such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc. Among these, methyl, ethyl, or isopropyl is preferable, methyl or ethyl is more preferable, and methyl is particularly preferable.
  • the anilino group having at least one sulfo group in X usually has 1 to 3, preferably 1 or 2, more preferably 2 sulfo groups.
  • Anilino group may be mentioned. Specific examples include those having one sulfo group such as 2-sulfoanilino, 3-sulfoanilino, 4-sulfoanilino; 2,3-disulfoanilino, 2,4-disulfoanilino, 2,5-disulfoanilino, 3,4-disulfoanilino, Having two sulfo groups such as 3,5-disulfoanilino; 2,3,4-trisulfoanilino, 2,3,5-trisulfoanilino, 2,3,6-trisulfoanilino, 3, And those having three sulfo groups such as 4,5-trisulfoanilino; Of these, 2,5-disulfoanilino;
  • the number of the substituents is usually one or two, Preferably one.
  • the type of the substituent may be single or plural, and is arbitrarily selected from the eight types of groups described as the above group.
  • alkoxy group in the above group examples include straight-chain, branched-chain, and cyclic groups, preferably straight-chain or branched-chain groups, and more preferably straight-chain groups.
  • the range of carbon number is usually C1-C6, preferably C1-C4, more preferably C1-C3.
  • Specific examples include straight chain such as methoxy, ethoxy, n-propoxy, n-butoxy, n-pentoxy, n-hexyloxy; isopropoxy, isobutoxy, sec-butoxy, t-butoxy, isopentyloxy, isohexyloxy, etc.
  • a cyclic group such as cyclopropoxy, cyclopentoxy, cyclohexyloxy, etc.
  • methoxy, ethoxy, or isopropoxy is preferable, and methoxy is more preferable.
  • alkylcarbonylamino group in the above group examples include straight-chain or branched-chain groups, and straight-chain groups are preferred.
  • the range of the carbon number of the alkyl moiety is usually C1-C6, preferably C1-C4, more preferably C1-C3.
  • Specific examples include straight chain such as methylcarbonylamino (acetylamino), ethylcarbonylamino, n-propylcarbonylamino, n-butylcarbonylamino, etc .; branched chain such as isopropylcarbonylamino; Of these, acetylamino is preferred.
  • b and c and the sum of b and c are all average values.
  • b is greater than 0.0 and less than 3.9.
  • c is 0.1 or more and less than 4.0.
  • the sum of b and c is 1.0 or more and less than 4.0.
  • the average value of the heteroaromatic rings in rings A to D is greater than 0.0 and less than or equal to 3.0, and similarly the benzene ring is greater than or equal to 1.0 and less than 4.0.
  • the heteroaromatic ring in rings A to D is 0.2 or more and 2.0 or less, and the benzene ring is 2.0 or more and 3.8 or less, b is 1.8 or more and 3.6 or less, and c is It is 0.2 or more and 2.0 or less, and the sum of b and c is 2.0 or more and 3.8 or less. More preferably, when the heteroaromatic ring in rings A to D is 0.3 to 1.5 and the benzene ring is 2.5 to 3.7, b is 2.2 to 3.0, and c Is 0.3 or more and 1.5 or less, and the sum of b and c is 2.5 or more and 3.7 or less.
  • heteroaromatic ring in rings A to D is 0.5 or more and 1.2 or less, and the benzene ring is 2.8 or more and 3.5 or less
  • b is 2.1 or more and 3.1 or less
  • c Is 0.4 or more and 1.4 or less
  • the sum of b and c is 2.8 or more and 3.5 or less.
  • n which means the number of chlorosulfonyl groups is an average value, and means the same number as the sum of said b and c including a preferable thing.
  • the dye represented by the above formula (1) can form a salt using an acidic functional group such as a sulfo group in the molecule.
  • the counter cation preferably forms a salt with each cation such as inorganic metal; ammonia (NH 3 ); organic base;
  • the inorganic metal include alkali metals and alkaline earth metals.
  • the alkali metal include lithium, sodium, potassium and the like.
  • alkaline earth metals include calcium and magnesium.
  • organic base examples include organic amines such as C1-C3 alkylamines such as methylamine and ethylamine; monoamines such as monoethanolamine, diethanolamine, triethanolamine, monoisopropanolamine, diisopropanolamine and triisopropanolamine. -, Di-, or tri-C1-C4 alkanolamines; and the like.
  • preferable salts of the dye represented by the formula (1) include alkali metal salts such as sodium salt, potassium salt and lithium salt; monoethanolamine, diethanolamine, triethanolamine, monoisopropanolamine, diisopropanolamine , Salts with mono-, di- or tri-C1-C4 alkanolamines such as triisopropanolamine; ammonium salts (NH 4 + ); and the like, but are not limited thereto.
  • the salt of the dye represented by the formula (1) may vary depending on the type of the salt, such as physical properties such as solubility; performance of ink containing the dye, particularly performance related to fastness; is there.
  • dye represented by the said Formula (1) is shown in following Table 1, this invention is not limited to these.
  • the dye represented by the formula (1) is a complex mixture containing a plurality of isomers, and exhibits the effects obtained by the present invention in that state.
  • a typical structural formula is described for convenience.
  • surface in order to avoid complexity, the 1st decimal place was rounded off and described. For this reason, b in Table 1 is described as 0 for convenience, but this is a matter of calculation processing, meaning that b in Formula (1) is greater than 0.0. Absent.
  • dye represented by the said Formula (1) is the compound represented by the said Formula (3) obtained by chlorosulfonylating the compound represented by the said Formula (2), and the said Formula (4).
  • the organic amine represented is reacted in the presence of an ammonia source.
  • Any of the compounds represented by the above formula (2) can be obtained by a known method or a modification thereof. Examples of known methods include the methods disclosed in Patent Documents 15 to 17 mentioned above.
  • a compound represented by the formula (2) is added to chlorosulfonic acid and reacted, and then a chlorinating agent is further added to react. Is preferred.
  • a compound in which a chlorosulfonyl group and a sulfo group are mixed and substituted is obtained, and the target compound represented by the formula (3) is obtained. It is difficult to obtain with high selectivity. For this reason, a method of reacting the compound represented by the formula (2) with chlorosulfonic acid and then adding a chlorinating agent to convert the sulfo group into a chlorosulfonyl group is preferred.
  • the chlorosulfonic acid is usually used 3 to 20 times by mass, preferably 5 to 10 times by mass with respect to the compound represented by the formula (2).
  • the reaction temperature is usually 100 to 150 ° C, preferably 120 to 150 ° C.
  • the reaction time varies depending on the reaction conditions such as the reaction temperature, but is usually 1 to 10 hours.
  • the chlorinating agent include, but are not limited to, thionyl chloride, sulfuryl chloride, phosphorus trichloride, phosphorus pentachloride, and phosphorus oxychloride. Of these, thionyl chloride is preferred.
  • the addition amount of the chlorinating agent is not uniform depending on the kind thereof, but is usually 6 to 40 mol, preferably 9 to 20 mol, relative to 1 mol of the compound represented by the formula (2).
  • the reaction temperature at this time is usually 30 to 100 ° C., preferably 50 to 90 ° C.
  • the reaction time varies depending on the reaction conditions such as the reaction temperature, but is usually 1 to 10 hours.
  • the organic amine represented by the above formula (4) can be produced by the following method. That is, 5 to 60 mol of alcohols corresponding to R 1 represented as “R 1 —OH”, 1 mol of 2,4,6-trichloro-S-triazine (cyanuric chloride), 0.8% sodium bicarbonate ⁇ 1.2 mol is reacted under the conditions of 5 to 70 ° C. for 2 to 12 hours to obtain a reaction liquid containing the primary condensate.
  • the obtained primary condensate may be isolated as a solid such as a wet cake by an appropriate method (for example, salting out) and used for the next reaction.
  • reaction solution or wet cake (preferably the reaction solution) of the primary condensate is added to an aqueous solution of 0.9 to 1.5 mol of aniline corresponding to X, and an alkali metal hydroxide such as sodium hydroxide is added.
  • an alkali metal hydroxide such as sodium hydroxide
  • the reaction of the compound represented by the formula (3) and the organic amine represented by the formula (4) is carried out in water in the presence of ammonia or an ammonia generating source at about pH 8 to 10, preferably 5 to 70 ° C., preferably Is carried out by reacting at 5 to 40 ° C. for 1 to 20 hours to obtain the target dye represented by the formula (1).
  • ammonia include ammonia water; a water-miscible organic solvent containing ammonia gas; and the like.
  • Examples of the water-miscible organic solvent containing ammonia gas include dimethylformamide and dimethylacetamide containing ammonia gas.
  • Ammonia generating source means a chemical substance that generates ammonia by neutralization or decomposition.
  • the chemical substance include ammonium salts that generate ammonia by neutralization of ammonium chloride and ammonium sulfate; substances that generate ammonia by thermal decomposition of urea and the like.
  • ammonia is preferable, and among the ammonia, ammonia water is more preferable.
  • Concentrated aqueous ammonia (usually commercially available as approximately 28% ammonia water), or water as necessary is available. Aqueous ammonia diluted with 1 is more preferred, and concentrated aqueous ammonia is particularly preferred from the advantage that the amount of the reaction solution can be reduced.
  • the amount of the organic amine represented by the formula (4) is usually the theoretical value [the value of c in the dye represented by the target formula (1) with respect to 1 mol of the compound represented by the formula (3).
  • the number of moles of the organic amine represented by the formula (4) required for obtaining the same is approximately 1 mole equivalent, but it depends on the reactivity of the organic amine used and the reaction conditions, and is limited to these. It is not something. Usually, it is about 1 to 3 molar equivalents, preferably about 1 to 2 molar equivalents of the above theoretical value.
  • Examples of the method for isolating the dye represented by the formula (1) from the reaction solution in the final step in the production method include acid precipitation; salting out; acid precipitation using a combination thereof;
  • the salting out is preferably performed, for example, in the range of acidic to alkaline, preferably pH 1-11.
  • the temperature at the time of salting out is not particularly limited, but it is preferable to salt out by adding sodium chloride or the like after heating to 40 to 80 ° C., preferably 40 to 60 ° C.
  • acid salting out in which salting out is performed under strong acidity of about pH 1 is preferable.
  • phthalocyanine-based porphyrazine dyes are generally classified into three types according to the substitution position of the substituent: ⁇ -position substitution type; ⁇ -position substitution type; or ⁇ -position mixed substitution type. Is done. These classifications are disclosed in, for example, Patent Document 12 and Patent Document 21.
  • dye represented by the said Formula (1) has a benzene ring with a specific average value as the rings A thru
  • dye represented by the said Formula (1) of this invention is (alpha) (beta) position mixed substitution type among these.
  • the ink composition of the present invention is a substantially aqueous ink composition containing a dye represented by the above formula (1).
  • the ink composition containing the coloring matter can be used as a cyan ink.
  • the ink composition of the present invention has a low dye concentration used not only for cyan ink having a high dye concentration but also for the purpose of smoothly reproducing the gradation portion of an image; for the purpose of reducing graininess in a light color region; It may be used as a cyan ink having a density (referred to as light cyan ink or photocyan ink).
  • the dye and the yellow dye may be blended for use in preparing a green ink, or the dye and the magenta dye may be blended for use in preparing a violet or blue ink.
  • an ink can be prepared by blending the coloring matter with, for example, a yellow coloring matter, a magenta coloring matter, or the like, and each ink such as dark yellow, gray, or black can be obtained.
  • the content of anions such as Cl ⁇ and SO 4 2 ⁇ contained as impurities in the dye represented by the formula (1) is small. .
  • the total content of Cl - and SO 4 2- in the total mass of the dye it is usually 5% by mass or less, preferably 3% by mass or less, more preferably 1% by mass or less.
  • the lower limit may be equal to or lower than the detection limit of the detection device, that is, 0%.
  • the Cl - and SO 4 content of 2 can be measured, for example, ion chromatography.
  • Examples of the method for producing the coloring matter having a low anion content include desalting with a reverse osmosis membrane; suspension purification in a hydrous organic solvent, preferably hydrous alcohol, and the like.
  • Examples of the alcohol used for the hydrous alcohol include C1-C4 alcohol, preferably C1-C3 alcohol, specifically methanol, ethanol, n-propanol, 2-propanol (isopropanol) and the like.
  • the kind of alcohol is appropriately selected in consideration of the solubility of the pigment and the like.
  • the pigment suspension is heated to the boiling point or a temperature close to the boiling point and stirred, then cooled as necessary, and the pigment is separated by filtration.
  • the method is also preferably performed.
  • the pigment wet cake obtained by the filtration and separation may be dried by a known method and used, for example, for the preparation of an ink composition.
  • dye represented by Formula (1) forms the copper complex, this center metal copper ion is not included in an impurity.
  • the standard for the impurity content is preferably about 500 ppm or less for heavy metal ions such as zinc and iron, calcium ions, silica, etc. in the total mass of the dry solid of the dye represented by formula (1). May be below the detection limit of the analytical instrument, ie 0 ppm.
  • the impurity content in the total mass of the dye can be measured by ion chromatography, atomic absorption, or ICP (Inductively Coupled Plasma) emission analysis.
  • the ink composition of the present invention contains 0.1 to 8% by mass, preferably 0.3 to 6% by mass of the dye represented by the formula (1) with respect to the total mass of the composition.
  • the ink composition may further contain a water-soluble organic solvent and an ink preparation agent as necessary within a range that does not impair the effects of the present invention.
  • the water-soluble organic solvent is used with the expectation of effects such as dye dissolution, prevention of drying, adjustment of viscosity, acceleration of penetration, adjustment of surface tension, and defoaming, and is contained in the ink composition of the present invention. Is preferred.
  • ink preparation agents include antiseptic / antifungal agents, pH adjusters, chelating reagents, rust preventive agents, UV absorbers, viscosity adjusters, dye solubilizers, antifading agents, surface tension adjusters, and antifoaming agents. You may add as needed.
  • the water-soluble organic solvent is usually 0 to 60% by mass, preferably 10 to 50% by mass, and the ink preparation agent is usually 0 to 20% by mass, preferably 0 to 15% by mass, based on the total mass of the ink composition; It is good to use.
  • the balance is water.
  • water-soluble organic solvent examples include C1-C4 alcohols such as methanol, ethanol, n-propanol, isopropanol, n-butanol, isobutanol, sec-butanol and tert-butanol; N, N-dimethylformamide, N, Carboxylic acid amides such as N-dimethylacetamide; complex such as 2-pyrrolidone, N-methyl-2-pyrrolidone, 1,3-dimethylimidazolidin-2-one, 1,3-dimethylhexahydropyrimido-2-one Cyclic ketones; 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 glycol; 1,2- or 1,4-butylene glyco 1,6-hexyl
  • Preferred as the above-mentioned water-soluble organic solvent are isopropanol, glycerin, mono-, di- or triethylene glycol, dipropylene glycol, 2-pyrrolidone, N-methyl-2-pyrrolidone, butyl carbitol, more preferably isopropanol.
  • antiseptic / antifungal agents examples include organic sulfur, organic nitrogen sulfur, organic halogen, haloaryl sulfone, iodopropargyl, N-haloalkylthio, benzothiazole, nitrile, pyridine, 8- Oxyquinoline, isothiazoline, dithiol, pyridine oxide, nitropropane, organotin, phenol, quaternary ammonium salt, triazine, thiadiazine, anilide, adamantane, dithiocarbamate, brominated indanone And compounds such as benzyl bromacetate and inorganic salts.
  • 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-isothiazoline-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 examples include sodium sorbate, sodium benzoate, sodium acetate, manufactured by Arch Chemical Co., Ltd., trade names Proxel RTM GXL (S), Proxel RTM XL-2 (S), and the like.
  • 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 6.0 to 11.0 for the purpose of improving the storage stability of the 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 examples include alkali metal carbonates; aminosulfonic acids such as taurine; and the like.
  • chelating reagent examples include disodium 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.
  • the ultraviolet absorber examples include benzophenone compounds, benzotriazole compounds, cinnamic acid compounds, triazine compounds, and stilbene compounds. Further, a compound that absorbs ultraviolet rays typified by a benzoxazole-based compound and emits fluorescence, a so-called fluorescent brightener can also be used.
  • viscosity modifier examples include water-soluble polymer compounds such as polyvinyl alcohol, cellulose derivatives, polyamines, and polyimines.
  • dye solubilizer examples include urea, ⁇ -caprolactam, ethylene carbonate, and the like.
  • the anti-fading agent is used for the purpose of improving image storage stability.
  • various organic and metal complex antifading agents can be used.
  • organic anti-fading agents include hydroquinones, alkoxyphenols, dialkoxyphenols, phenols, anilines, amines, indanes, chromans, alkoxyanilines, heterocycles, etc. Includes nickel complexes and zinc complexes.
  • Examples of the surface tension adjusting agent include surfactants, and examples thereof include anionic surfactants, amphoteric surfactants, cationic surfactants, and nonionic surfactants.
  • 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, alkylaryl sulfonate, diethylsulfosuccinate Salt, diethyl hexyl sulphosuccinate, dioctyl
  • 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 and other imidazoline derivatives. 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 (e.g., manufactured by Nissin Chemical Industry Co., Ltd. Surfynol RTM
  • antifoaming agent a highly oxidized oil-based, glycerin fatty acid ester-based, fluorine-based, or silicone-based compound is used as necessary.
  • the surface tension of the ink of the present invention is usually 25 to 70 mN / m, preferably 25 to 60 mN / m.
  • the viscosity of the ink of the present invention is preferably adjusted to 30 mPa ⁇ s or less, and more preferably 20 mPa ⁇ s or less.
  • the water used for preparing the ink composition is preferably water having few impurities such as metal ions, 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 microns, preferably 0.8 to 0.1 microns.
  • the ink composition of the present invention can be used not only for forming a single color image but also for forming a full color image.
  • a full-color image it may be used as an ink set of three primary colors with magenta ink and yellow ink, and further as an ink set of four colors with black ink added thereto.
  • it can be used as an ink set in combination with light cyan ink, light magenta ink, blue ink, green ink, orange ink, dark yellow ink, gray ink, etc.
  • the color tone of the area can also be expressed. Examples of the colorant used in each color ink set used in combination with the ink composition of the present invention include known colorant colors.
  • the ink composition of the present invention can be used for various recording applications such as printing, copying, marking, writing, drawing, stamping and the like, and is particularly suitable for ink jet recording.
  • the inkjet recording method of the present invention provides various recording materials, that is, plain paper, resin-coated paper, by supplying energy to the ink composition of the present invention in accordance with a recording signal and discharging droplets of the ink composition.
  • Ink jet paper, glossy paper, glossy film, electrophotographic paper, fiber and cloth (cellulose, nylon, wool, etc.), glass, metal, ceramics, leather, etc. is there.
  • a polymer fine particle dispersion (also referred to as polymer latex) may be used in combination for the purpose of imparting glossiness and water resistance to the image; the purpose of improving weather resistance;
  • the timing for applying the polymer latex to the recording material may be before, after, or simultaneously with the inkjet recording on the recording material. That is, the ink composition of the present invention may be recorded on a recording material containing a polymer latex, or the polymer latex may be contained in the ink composition. Further, before or after recording on the recording material with the ink composition, the polymer latex may be applied to the recording material as a single liquid.
  • the colored product of the present invention is a) the ink composition according to 4) above, b) The ink composition according to 5) above, or c) The ink jet recording method described in 7) above, Means a substance colored by any of the above.
  • the substance to be colored is not particularly limited, and examples thereof include information transmission sheets such as paper and film, fibers and cloths (cellulose, nylon, wool, etc.), leather, color filter base materials, and the like. Is preferred.
  • a surface-treated sheet specifically, a sheet having an ink receiving layer containing white inorganic pigment particles on a support (base material) such as paper, synthetic paper, or film is preferable.
  • the ink receiving layer is formed by, for example, impregnating or coating the base material with a cationic polymer; white inorganic fine pigment particles capable of absorbing pigments in ink, such as porous silica, alumina sol, and special ceramics; A method of coating the surface of the substrate together with a hydrophilic polymer such as polyvinylpyrrolidone;
  • An information transmission sheet having such an ink-receiving layer is usually called ink jet dedicated paper (film), glossy paper (film) or the like.
  • Typical examples of the above-mentioned special paper that can be obtained as a commercial product include Canon Inc., trade name: Photographic Paper / Glossy Pro “Platinum Grade”, Photographic Paper / Glossy Gold; Seiko Epson Corporation, Tradename Photographic paper Crispier (high gloss), Photographic paper (glossy), Photo matte paper; Nihon Hewlett-Packard Co., Ltd., trade name Advanced photo paper (glossy); Brother Co., Ltd., trade name Premium Plus Glossy Photopaper And so on.
  • plain paper can also be used. Specific examples include PB paper GF500 manufactured by Canon Inc., and trade name double-sided plain plain paper manufactured by Seiko Epson Corporation.
  • a container containing the above ink composition may be loaded at a predetermined position of the ink jet printer and recording may be performed by the above recording method.
  • the ink jet printer include a piezo printer using mechanical vibration; a bubble jet (registered trademark) printer using bubbles generated by heating.
  • the ink composition of the present invention is not limited to these ejection methods, and any method can be used.
  • the ink composition containing the coloring matter represented by the formula (1) of the present invention does not precipitate or separate even after long-term storage, and does not cause changes in physical properties, hue, etc. Good stability. Further, when the ink composition is used for ink jet recording, the ejector (ink head) is not blocked.
  • the ink composition of the present invention does not cause a change in physical properties even in recording for a relatively long time and under constant recirculation by a continuous inkjet printer; intermittent recording by an on-demand inkjet printer;
  • the ink composition has a clear and good hue as a cyan ink, and a recorded image having a high print density can be obtained, so that the dye density in the ink can be reduced. For this reason, it has industrial advantages such as cost reduction. Further, since the recorded image is excellent in various fastnesses such as light resistance, water resistance, ozone gas resistance and moisture resistance, particularly ozone gas resistance, and it is extremely difficult to cause bronzing, a high quality recorded image can be obtained.
  • the obtained wet cake was added to 300 parts of 5% hydrochloric acid, heated to 60 ° C. and stirred at the same temperature for 1 hour, and then the solid was separated by filtration and washed with 300 parts of water to obtain a wet cake.
  • the obtained wet cake was added to 300 parts of 5% aqueous ammonia and stirred at 60 ° C. for 1 hour, and then the solid was separated by filtration and washed with 300 parts of water to obtain 138.2 parts of a wet cake.
  • the obtained wet cake was dried at 80 ° C. to obtain 46.3 parts of the objective compound as a blue solid.
  • Example 1 At room temperature, 5.8 parts of the compound of the formula (2) obtained in Example 1 (Step 1) was gradually added to 46.2 parts of chlorosulfonic acid so as not to exceed 60 ° C., and then at 140 ° C. Reacted for 4 hours.
  • the obtained reaction liquid was cooled to 70 ° C., 17.9 parts of thionyl chloride was added dropwise over 30 minutes, and the mixture was further reacted at 70 ° C. for 3 hours.
  • the reaction solution was cooled to 30 ° C. or lower, slowly poured into 800 parts of ice water, the precipitated solid was separated by filtration, and washed with 200 parts of cold water to obtain 33.0 parts of the target compound wet cake.
  • Cyanuric chloride 36.8 parts, trade name Leocol RTM TD-90 (4 parts) and sodium hydrogen carbonate (16.8 parts) were added to 160 parts of methanol and reacted at 30 ° C. or lower for 1 hour to obtain the primary condensate.
  • a reaction solution containing was obtained.
  • 2,5-Disulfoaniline (56.1 parts) and 25% aqueous sodium hydroxide solution (32 parts) were added to 280 parts of water to adjust the pH to 3-5.
  • the reaction solution containing the primary condensate obtained as described above is gradually added to this solution, and further reacted overnight at room temperature while adjusting the pH to 6 to 7 with a 25% aqueous sodium hydroxide solution to contain the secondary condensate.
  • a reaction solution was obtained.
  • reaction liquid 360 parts of hydrochloric acid and 125 parts of ice were added and cooled to 0 ° C., and 120 parts of ethylenediamine was further added dropwise.
  • the resulting solution was reacted at 80 ° C. for 2.5 hours while adjusting the pH to 5 to 6 with a 25% aqueous sodium hydroxide solution to obtain a reaction solution containing a tertiary condensate.
  • hydrochloric acid was added to adjust the pH to 1.0.
  • the liquid volume at this time was 1000 parts.
  • 200 parts of sodium chloride was added and stirred for 30 minutes, and the precipitated solid was separated by filtration to obtain 183 parts of a wet cake.
  • the obtained wet cake was added to 1000 parts of water and adjusted to pH 9.0 with 25% aqueous sodium hydroxide solution to obtain a solution.
  • 55 parts of hydrochloric acid was added to adjust the pH to 1.0.
  • the liquid volume was 1400 parts.
  • To this solution was added 280 parts of sodium chloride, and the mixture was stirred at room temperature for 30 minutes and further at 0 ° C. for 30 minutes, and the precipitated solid was separated by filtration to obtain 60 parts of a wet cake.
  • the obtained wet cake was added to a mixed liquid of 224 parts of methanol and 56 parts of water to form a suspension and stirred at 50 ° C. for 1 hour, and then the solid was separated by filtration to obtain 51.3 parts of a wet cake. .
  • the obtained wet cake was dried to obtain 37.0 parts of a desired organic amine white powder.
  • the temperature of the reaction solution was raised to 50 ° C., 33.8 parts of sodium chloride was added and stirred for 30 minutes, then adjusted to pH 1.0 with concentrated hydrochloric acid over 20 minutes, and the precipitated solid was separated by filtration.
  • the wet cake was washed with 100 parts of a sodium chloride aqueous solution to obtain 62.3 parts of a wet cake.
  • the obtained wet cake was added to 200 parts of water, and adjusted to pH 9.0 with 25% aqueous sodium hydroxide solution to obtain a solution.
  • the liquid volume at this time was 275 parts.
  • the temperature of this solution was raised to 50 ° C., 22.5 parts of sodium chloride was added and stirred for 30 minutes, and then adjusted to pH 1.0 with concentrated hydrochloric acid over 20 minutes.
  • the wet cake was washed with 100 parts of an aqueous sodium solution to obtain 37.1 parts of a wet cake.
  • the obtained wet cake was added to a mixed liquid of 160 parts of ethanol and 40 parts of water to form a suspension. After stirring this liquid at 50 ° C. for 1 hour, the solid was separated by filtration to obtain 32.0 parts of a wet cake. It was.
  • the obtained wet cake was dried to obtain 10.0 parts of the free acid of the target pigment as a blue powder. ⁇ max: 605 nm.
  • the reaction mixture was cooled to 65 ° C., 50 parts of methanol was added, and the precipitated solid was separated by filtration and washed with 200 parts of methanol to obtain 106.1 parts of a wet cake.
  • the total amount of the obtained wet cake was added to 343 parts of water, 57 parts of hydrochloric acid, and 100 parts of sodium chloride to form a suspension.
  • the solid was separated by filtration, The wet cake was obtained by washing with 200 parts of a 20% aqueous sodium chloride solution.
  • the obtained wet cake was added to a mixed solvent of 400 parts of methanol and 100 parts of 25% aqueous sodium hydroxide solution to form a suspension, heated to 60 ° C. and stirred at the same temperature for 1 hour, and the solid was separated by filtration. And washed with 200 parts of methanol to obtain 76.5 parts of a wet cake.
  • the obtained wet cake was added to a mixed solvent of 540 parts of methanol and 60 parts of water to form a suspension, heated to 60 ° C. and stirred at the same temperature for 1 hour, and then the solid was separated by filtration to obtain 200 parts of methanol. To obtain 72.0 parts of a wet cake.
  • the temperature of the reaction solution was raised to 50 ° C., 35 parts of sodium chloride was added and stirred for 30 minutes, then adjusted to pH 1.0 over 20 minutes with concentrated hydrochloric acid, and the precipitated solid was separated by filtration, and 20% sodium chloride.
  • By washing with 100 parts of an aqueous solution 61.2 parts of a wet cake was obtained.
  • the obtained wet cake was added to 130 parts of water and adjusted to pH 9.0 with 25% aqueous sodium hydroxide solution to obtain a solution.
  • the liquid volume at this time was 200 parts.
  • Example 2 [(A) Preparation of ink] Each component described in Table 2 below was mixed and dissolved, and filtered through a 0.45 ⁇ m membrane filter (manufactured by Advantech) to prepare an ink for evaluation test.
  • water ion-exchanged water was used. Further, the pH of the ink was adjusted with sodium hydroxide so as to be 8 to 10, and water was added so that the total amount became 100 parts.
  • Preparation of an ink using the pigment obtained in Example 1 is referred to as Example 2.
  • a comparative ink was prepared in the same manner as in Example 2 except that the comparative pigment obtained in Comparative Example 1 was used instead of the pigment obtained in Example 1. This ink preparation is referred to as Comparative Example 2.
  • surfactant described in Table 2 below, trade name Surfinol RTM 104PG50 manufactured by Nissin Chemical Co., Ltd. was used.
  • Inkjet recording was performed on the following three types of glossy paper using an inkjet printer (product name: PIXUS ip4500, manufactured by Canon Inc.). During ink jet recording, a gradation image pattern was created so that six levels of gradations of 100%, 85%, 70%, 55%, 40%, and 25% were obtained, and this was used as a test piece. .
  • Glossy paper 1 “Fine Film Photo Pro” by Fuji Film Co., Ltd.
  • Glossy paper 2 “Advanced Photo Paper” manufactured by Hewlett-Packard Company
  • Glossy Paper 3 “Photographic Paper Crispear RTM ” manufactured by Seiko Epson Corporation
  • Example 2 using the ⁇ -position mixed substitution type dye of the present invention is equivalent to or better than the ⁇ -position substitution type Comparative Example 2 in ozone gas resistance.
  • Comparative Example 2 the occurrence of bronzing was confirmed in the 70% gradation portion in the two types of glossy paper and in the 100% gradation portion in the remaining one type of glossy paper. There was no bronzing in all gradations. This indicates that the quality of the recorded image with the ink of Example 2 is extremely high, and the image recorded with the ⁇ -position mixed substitution type dye of the present invention and the ink composition containing the same exhibits fastness and quality. It was confirmed that the balance was extremely excellent.
  • the dye and the ink composition containing the dye Since the image recorded with the dye of the present invention and the ink composition containing the same showed excellent fastness and high quality, the dye and the ink composition containing the dye, various recording uses, particularly It is extremely suitable for inkjet recording applications.

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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)
  • Ink Jet Recording Methods And Recording Media Thereof (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)
  • Ink Jet (AREA)

Abstract

L'invention concerne un colorant qui est idéal pour l'enregistrement à jet d'encre en ce que le colorant a une excellente résistance à l'ozone et produit peu de bronzage même lorsque la concentration en colorant dans de l'encre est élevée. L'invention concerne également un procédé de fabrication du colorant et une composition d'encre contenant le colorant. Selon la présente invention, le composé représenté par la formule (2) est soumis à une chlorosulfonylation pour obtenir le composé représenté par la formule (3), qui est mis à réagir avec une amine organique représentée par la formule (4) en présence d'ammoniac ou similaire pour produire le colorant, etc., représenté par la formule (1). Dans chaque formule, les noyaux A à D représentent chacun indépendamment un noyau benzène ou un noyau hétéroaromatique, E représente alkylène, R1 représente un groupe alkyle, X représente un groupe aniline ou similaire ayant des groupes sulfo, b est supérieur à 0,0 mais inférieur à 3,9, c est 0,1 ou plus mais inférieur à 4,0, et la somme de b et c est 1,0 ou plus mais inférieure à 4,0. [Dans chacune des formules, les noyaux A à D représentent chacun indépendamment un noyau benzénique ou un noyau hétéroaromatique, E représente alkylène, R1 représente un groupe alkyle, X représente un groupe aniline ou similaire ayant des groupes sulfo, b est supérieur à 0,0 mais inférieur à 3,9, c est 0,1 ou plus mais inférieur à 4,0, et la somme de b et c est 1,0 ou plus mais inférieure à 4,0].
PCT/JP2011/073223 2010-10-14 2011-10-07 Colorant porphyrazine, son procédé de fabrication, composition d'encre et corps coloré Ceased WO2012050061A1 (fr)

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Cited By (4)

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Publication number Priority date Publication date Assignee Title
WO2013064802A1 (fr) * 2011-10-31 2013-05-10 Fujifilm Imaging Colorants Limited Azaphthalocyanines
EP2706097A1 (fr) 2012-09-05 2014-03-12 Canon Kabushiki Kaisha Encre, cartouche d'encre et procédé d'enregistrement à jet d'encre
WO2015020222A1 (fr) 2013-08-08 2015-02-12 日本化薬株式会社 Composition d'encre, procédé d'impression par jet d'encre l'utilisant et matière colorée
JPWO2013191029A1 (ja) * 2012-06-18 2016-05-26 日本化薬株式会社 ポルフィラジン色素及びその用途

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10851256B2 (en) 2016-12-14 2020-12-01 Canon Kabushiki Kaisha Inkjet printing method and inkjet printing apparatus

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JPS60208365A (ja) * 1984-04-02 1985-10-19 Nippon Kayaku Co Ltd 銅フタロシアニン化合物及びこれを含有する水性記録液
JP2004323605A (ja) * 2003-04-23 2004-11-18 Nippon Kayaku Co Ltd 色素混合物、インク、インクセット、このインク又はインクセットを用いたインクジェット記録方法、着色体、及び製造方法
JP2007196395A (ja) * 2006-01-23 2007-08-09 Fujifilm Corp インクジェット記録媒体及びその製造方法、インクジェット記録方法、インクジェット記録セット、並びにインクジェット記録物
WO2008111635A1 (fr) * 2007-03-14 2008-09-18 Nippon Kayaku Kabushiki Kaisha Nouveau colorant porphyrazine, encre, jeu d'encres, et matière colorée de porphyrazine

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JP2004323605A (ja) * 2003-04-23 2004-11-18 Nippon Kayaku Co Ltd 色素混合物、インク、インクセット、このインク又はインクセットを用いたインクジェット記録方法、着色体、及び製造方法
JP2007196395A (ja) * 2006-01-23 2007-08-09 Fujifilm Corp インクジェット記録媒体及びその製造方法、インクジェット記録方法、インクジェット記録セット、並びにインクジェット記録物
WO2008111635A1 (fr) * 2007-03-14 2008-09-18 Nippon Kayaku Kabushiki Kaisha Nouveau colorant porphyrazine, encre, jeu d'encres, et matière colorée de porphyrazine

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013064802A1 (fr) * 2011-10-31 2013-05-10 Fujifilm Imaging Colorants Limited Azaphthalocyanines
JPWO2013191029A1 (ja) * 2012-06-18 2016-05-26 日本化薬株式会社 ポルフィラジン色素及びその用途
EP2706097A1 (fr) 2012-09-05 2014-03-12 Canon Kabushiki Kaisha Encre, cartouche d'encre et procédé d'enregistrement à jet d'encre
US8992674B2 (en) 2012-09-05 2015-03-31 Canon Kabushiki Kaisha Ink, ink cartridge and ink jet recording method
WO2015020222A1 (fr) 2013-08-08 2015-02-12 日本化薬株式会社 Composition d'encre, procédé d'impression par jet d'encre l'utilisant et matière colorée
KR20160040630A (ko) 2013-08-08 2016-04-14 닛뽄 가야쿠 가부시키가이샤 잉크 조성물, 이것을 사용하는 잉크젯 기록 방법, 및 착색체
US10190009B2 (en) 2013-08-08 2019-01-29 Nippon Kayaku Kabushiki Kaisha Ink composition, ink jet recording method using same, and colored material

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