Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
  • C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
  • C07D221/04—Ortho- or peri-condensed ring systems
  • C07D221/18—Ring systems of four or more rings
• • 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
  • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
  • C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
  • C09B62/02—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring
  • C09B62/04—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring to a triazine ring
  • C09B62/043—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring to a triazine ring containing two or more triazine rings linked together by a non-chromophoric link
• • 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, an aqueous magenta ink composition, and an ink jet recording method.
• the dyes used In order to reproduce the additive color image of R, G, B by CRT display etc. as faithfully as possible by the subtractive color image, the dyes used, especially the dyes used for Y, M, C inks, should be Y, M , C are desired to have a hue close to each standard and to be sharp.
• the ink composition is required to be stable for long-term storage, to have a high density of a printed image, and to be excellent in fastness such as water resistance, light resistance and gas resistance.
• ink jet pudding has been expanded from small pudding for OA to large pudding for industrial use, and robustness such as water resistance and light resistance is required more than ever.
• inorganic fine particles such as porous silica, cationic polymers, alumina sol or special ceramics that can adsorb the dye in the ink are PVA. It was greatly improved by coating the surface of paper with resin, etc., but stricter quality improvement such as improved moisture resistance during storage of printed materials such as photographs is required.
• a technology to significantly improve light fastness has not yet been established.In particular, among the four primary colors of Y, ⁇ , C, and K, dyes for magenta and yellow are inherently weak in light fastness, and improvement is important. Is an important issue.
• the dye skeleton of the magenta dye used in the water-soluble ink for ink jet recording is described in JP-A-54-8911, JP-A-8-60053, and JP-A-8-143978.
• Xanthene type found in Japanese Patent Application Laid-open Nos. Sho 61-62, 562, 62-156, 168, Hei 3-209, 370, Hei 7-1, 569
• Typical azo dyes using acetic acid such as those described in No. 8 and Japanese Patent Publication No. 7-78190, etc., are representative.
• xanthenes have very good hue and sharpness but very poor light fastness.
• azo-based dyes using sulfuric acid are good in terms of hue and water resistance, but are inferior in light resistance and sharpness.
• magenta dyes having excellent sharpness and light resistance have been developed for this type, but cyan dyes represented by copper phthalocyanine dyes have been developed. Lightfastness is still inferior to dyes of other hues such as dyes and yellow dyes.
• An object of the present invention is to provide a magenta dye having a hue and sharpness suitable for ink-jet recording and having high light fastness, gas fastness and moisture fastness of a recorded matter. Disclosure of the invention
• R is a hydrogen atom, an alkyl group, a hydroxy lower alkyl group, a cyclohexyl group, a mono- or dialkylaminoalkyl group or a cyano lower alkyl group
• Y is a chlorine, hydroxyl, amino, mono- or di-alkylamino group
• It may have a substituent selected from the group consisting of a sulfonic acid group, a carboxy group and a hydroxyl group on the alkyl group), an aralkylamino group, a cycloalkylamino group, an alkoxy group, a phenoxy group (a sulfone group on the benzene ring)
• An acid group, a carboxy group, an acetylamino group, an amino group, and a hydroxyl group which may be substituted with a substituent selected from the group consisting of an anilino group (a group selected from the group consisting of a sul
• Y is chlorine, hydroxyl, amino, alkylamino, dialkylamino, aralkylamino, cycloalkylamino, alkoxy, phenoxy (sulfonate, carboxy, acetylamino, amino, and hydroxyl) May be substituted with a substituent selected from the group consisting of: a sulfonic acid group, a carboxy group or a mono- or dialkylamino group having a hydroxyl group, and an anilino group (selected from the group consisting of a sulfonic acid group and a carboxy group.
• X may be substituted with one or two types of substituents, a naphthylamino group (a naphthyl group may be substituted with a sulfonic acid group) or a mono- or dialkylaminoalkylamino group, A novel anthrapyridone compound represented by the formula: or a salt thereof.
• Y is an amino group
• crosslinking group X is a diaminoalkylene group.
• Y is an amino group
• the cross-linking group X is a diaminophenylene group which may have a substituent.
• An aqueous magenta ink composition comprising, as a dye component, an anthrapyridone compound or a salt thereof according to any one of (1) to (14), (16) The aqueous magenta ink composition according to (15), which contains a water-soluble organic solvent,
• the crosslinking group X has the following formula
• A is a divalent hydrocarbon residue having 1 to 20 carbon atoms, and may include a nitrogen atom, an oxygen atom or a sulfur atom, n represents 1 or 2, m represents 1 or 0, When n is 1, m indicates 1, and when n is 2, m indicates 0.)
• novel anthrapyridone compound of the present invention is represented by the above formula (14), and a typical compound is a compound represented by the above formula (1).
• alkyl is not limited as long as it falls within the usual definition of “alkyl”. Usually, unless otherwise specified, an alkyl group having about 1 to 10 carbon atoms is preferable, and a lower alkyl group having about 1 to 4 carbon atoms is more preferable. The same applies to alkyl groups in alkoxy, aralkyl, etc.
• the alkyl group for R is, for example, a C 1 -C 4 alkyl such as a methyl group, an ethyl group, an n-propyl group or an n-butyl group.
• Examples of the alkyl in the hydroxy lower alkyl group and the cyano lower alkyl group for R include, for example, ethyl and propyl, with ethyl being preferred.
• alkylamino group for Y examples include a C1 to C8 alkylamino group such as a methylamino group, an ethylamino group, a butylamino group, and a 2-ethylhexylamino group.
• dialkylamino group examples include a C1-C8 dialkylamino group such as a getylamino group, a dibutylamino group, and a dihexylamino group.
• Aralkylamino groups include phenylamino, phenylethylamino and phenylpropylamino groups.
• (C 1 -C 6) alkylamino group and as the cycloalkylamino group, examples thereof include a cyclo (C 5 -C 7) alkylamino group such as a cyclohexylamino group and a cyclopentylamino group.
• Examples of the alkoxy group include a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, and a butoxy group. And C 1 -C 4 alkoxy groups.
• alkyl in the alkylamino group having a sulfonic acid group or a carboxy group examples include C1 to C4 alkyl such as methyl, ethyl, n-propyl, and n-butyl.
• phenoxy group in Y which may be substituted with a substituent selected from the group consisting of a sulfonic group, a carboxy group, an acetylamino group, an amino group and a hydroxyl group include, for example, 4-sulfophenoxy group, 4 —Carboxyphenoxy group,
• alkylamino group having a sulfonic acid group or a carboxy group in Y include, for example, a 2-sulfoethylamino group, a carboxymethylamino group, a 2-hydroxypropyloxyamino group, and a 1-carboxy group. Examples thereof include an ethylamino group, a 1,2-dicarboxylamino group and a di (carboxymethyl) amino group.
• alkylamino group having a hydroxyl group include hydroxyethylamino. And a dihydroxyethylamino group.
• anilino group in Y which may be substituted with one or two kinds of substituents selected from the group consisting of a sulfonic acid group and a carboxy group include, for example, 2,2.
• 5-disulfoarilino group, 3-sulfoadirino group, 2-sulfoadirino group, 4 _sulfoadirino group, 2-carboxy-4-sulfoadirino group, 2-caproloxy-5-sulfoaanilino group, etc. can give.
• naphthylamino group which may be substituted with a sulfonic acid group in Y include, for example, 3,6,8-trisulfo-1-naphthylamino group, 4,6,8-trisulfo-2-naphthylamino group, 3,6 , 8-trisulfo-2-naphthylamino group and 4,8-disulfo-2-naphthylamino group.
• the cross-linking group for X includes a nitrogen atom, an oxygen atom, or a nitrogen atom or an oxygen atom at both ends of a hydrocarbon residue having 1 to 20 carbon atoms which may contain a nitrogen atom, an oxygen atom, or a sulfur atom. And a divalent group having an oxygen atom as a bond.
• A is a divalent hydrocarbon residue having 1 to 20 carbon atoms, and may include a nitrogen atom, an oxygen atom or a sulfur atom, n represents 1 or 2, m represents 1 or 0, When n is 1, m represents 1, and when n is 2, m represents 0).
• Examples of the divalent hydrocarbon residue having 1 to 20 carbon atoms of A include, for example, a carbon residue having 1 to 15 carbon atoms which may contain 1 to 2 hetero atoms (eg, nitrogen atom, oxygen atom, sulfur atom, etc.).
• Divalent aliphatic group which may contain 1 to 3 hetero atoms (for example, nitrogen atom, oxygen atom, sulfur atom, etc.)
• Divalent aromatic group having 3 to 10 carbon atoms, preferably 5 to 10 carbon atoms
• a divalent group formed by bonding the aliphatic group and the aromatic group may have a substituent (a sulfonic acid group, a propyloxyl group, an amino group, or a lower alkyl group in the case of an aromatic group).
• the above aliphatic group is substituted with a lower alkyl group such as methylene, dimethylene (ethylene), trimethylene (propylene), 2-methyltrimethylene (2-methylpropylene), tetramethylene (butylene) and hexamethylene.
• a lower alkyl group such as methylene, dimethylene (ethylene), trimethylene (propylene), 2-methyltrimethylene (2-methylpropylene), tetramethylene (butylene) and hexamethylene.
• C1-C6 (poly) methylene, cyclopentane-1,2- or 1,3-diyl, cyclohexane-1,2-, _ 1,3- or 1,4-diyl C5-C7 cycloalkylene, such as cycloheptane-diyl, methylenecyclohexane-1,4-dimethylene (—CH 2 —C 6 H 10 —CH 2 —), methylene dicyclohexane-diyl ( _C 6 H 10 — CH 2 — C 6 H 10 —), methylenebis (methylcyclohexane-diyl) ⁇ —C 6 H 10 (CH 3 ) -CH 2 -C 6 H 10 (CH 3 ) _ ⁇ , cyclo Hexane-diyl-dimethylene ( CH 2 - C 6 H 1 ( ) _CH 2 _) lower alkylene and aliphatic rings (which may have a lower alkyl
• Examples of the divalent aromatic Shokumoto phenylene may be mentioned an aromatic group having 6 to 10 carbon atoms such as (- - C 6 H 4 _ ), naphthylene (_C 1 () H 6) .
• Xylylene is a divalent group formed by bonding the aliphatic group and the aromatic group. (-CH 2 -C 6 H 4 -CH 2 -) and the like.
• dimethylene hexamethylene, 1,
• Examples include 3-xylylene, methylenedicyclohexane-1,4-diyl, methylenebis (2-methylcyclohexane-4,1-diyl), and cyclohexane-1,3-diyldimethylene.
• crosslinking group X examples include a 1,2-diaminoethylene group (_NH—CH 2 CH 2 —NH—), a 1,4-diaminobutylene group (one NH—C 4 H 8 —NH—), and a 1,6- Diaminoalkylene group such as diaminohexylene group (—NH—C 6 H 12 —NH—), 1,4-pirazazinediyl group (_NC 4 H 8 N—), 1,4-diaminophenylene group ( Diaminophenylene groups such as one NH—C 6 H 4 —p-NH—) and 1,3-diaminophenylene group (—NH—C 6 H 4 -m-NH—); —Diaminophenylene group ⁇ — NH— C 6 H 4 (p-S0 3 H) —m-NH— ⁇ , 5-dihydroxyphenyl 1,1,3-diaminophenylene group and other substituted diaminophenylene groups, 1, 3
• R is a hydrogen atom or a methyl group
• ⁇ is a chlorine atom, a hydroxyl group or an amino group
• X is a diaminoethylene group, a 1,4-piperazinedyl group, a 1,3-diene Aminoxylylene, 4,4'-diaminodicyclohexylmethane, 4,4'-diamino-3,3, -dimethyldicyclohexylmethane, 1,3-bis (aminomethyl) cyclohexane .
• Table 1 shows specific examples of the novel anthrapyridone compound represented by the formula (1) of the present invention.
• Jiaminoechiren is 1, means 2-diamino ethylene group (-NH- _ ⁇ H-CH 2 CH 2).
• Ph represents a phenyl group, for example, Ph 0 represents a phenoxy group, HPh represents an anilino group, and the like.
• NHPh is a 4-sulfoaurino group (p-S03H indicates that the sulfonic acid group is at the para-position to the phenyl group), and NHPh (COOH) 2 (3,5) is 3,5- Dicarpoxy dilino group ⁇ Ph (C00H) 2 (3, 5) indicates that the phenyl group is substituted with a carbonyl group at the 3- and 5-positions of the phenyl group ⁇ , and the other groups are similarly described .
• naphthyl represents a naphthyl group
• H-2naphthyl (S03H) 3 (3,6,8) represents 3,6,8-trisulfo-12-naphthylamino
• NH (cyclohexyl) represents cyclohexylamino.
• A is a linking group, for example, a divalent hydrocarbon residue having 1 to 20 carbon atoms, which may include a nitrogen atom, an oxygen atom or a sulfur atom, n is 1 or 2, and m is 1 Or 0, and when n is 1, m indicates 1, and when n is 2, m indicates 0.
• A is preferably C 1 to C 6 (poly) methylene, Phenylene, xylylene, methylenedicyclohexane-diyl, methylenebis (methylcyclohexanediyl), cyclohexane-diyl-dimethylene which may be present, more preferably dimethylene, hexamethylene, 3_xylylene, methylenedicyclohexane-4,1-diyl, methylenebis (2-methylcyclohexane) -4,1-1diyl, cyclohexane-1,3-diyl-dimethylene, etc.) pH4 to 10, 5 ⁇ 90 ° C, 10 minutes ⁇ 5 hours (9) where Y is a chlorine atom and both ends of the crosslinking group X are amino groups.
• the crosslinking group —NH—A—NH— in the formula (9) is replaced with — ⁇ —A_ ⁇ —
• the compound is obtained, and the compound is treated in the same manner as described above to obtain a compound in which the crosslinking group —NH—A—NH— in the formula (10) is replaced with —0—A— ⁇ _.
• the compound thus obtained exists in the form of a free acid or a salt thereof.
• the free acid or a salt thereof can be used as an alkali metal salt, an alkaline earth metal salt, an alkylamine salt, an alkanolamine salt or an ammonium salt.
• an alkali metal salt such as a sodium salt, a potassium salt, a lithium salt or the like
• an alkanoate such as a monoethanolamine salt, a diethanolamine salt, a triethanolamine salt, a monoisopropanolamine salt, a diisopropanolamine salt, a triisopropanolamine salt, etc.
• Lumin salts and ammonium salts As a method for preparing a salt, for example, sodium salt is added to the reaction solution of the tertiary condensate obtained above, salting out and filtration are performed to obtain a sodium salt as a wet cake, and the wet cake is dissolved in water again.
• the crystals obtained by adjusting the pH to 1 to 2 by adding hydrochloric acid are filtered off to obtain the free acid (or a part thereof as a sodium salt). Furthermore, if the wet cake in the form of the free acid is stirred with water, for example, potassium hydroxide, lithium hydroxide, and aqueous ammonia are added to make it alkaline, the potassium salt, the lithium salt, and the ammonia salt, respectively. A salt is obtained.
• the anthrapyridone compound of the formula (6) can be obtained, for example, as follows. That is, the following equation (1 1)
• the compound of the formula (13) is sulfonated in 50% to 120 ° C. in 8%;
• the aqueous magenta ink composition of the present invention comprises a compound represented by the above formulas (1) and (2) or a salt thereof, which is dissolved in water or an aqueous solvent (including a water-soluble organic solvent (dissolution aid described below. )) Dissolved in water).
• the pH of the ink is preferably about 6 to 11.
• this water-based ink composition is used for printing ink jet recording, it is preferable to use, as a pigment component, one having a low content of inorganic substances such as metal cation chlorides and sulfates.
• the total content of sodium chloride and sodium sulfate is 1% by weight or less.
• the pigment component of the present invention having a small amount of inorganic substances
• a usual method using a reverse osmosis membrane, or a dried product of the pigment component of the present invention or a wet cake is stirred a required number of times in a mixed solvent of methanol and water. Then, the operation of desalting by filtration and drying may be repeated.
• the aqueous ink composition of the present invention is prepared using water as a medium.
• the compound of the present invention or a salt thereof is contained in the aqueous ink composition preferably in an amount of 0.1 to 20% by weight, more preferably 1 to 20% by weight. -10% by weight, more preferably about 2-8% by weight.
• the aqueous ink composition of the present invention may further contain 0 to 30% by weight of a water-soluble organic solvent and 0 to 5% by weight of an ink conditioner. The balance is water.
• the ink composition of the present invention is prepared by adding the compound of the present invention or a salt thereof and, if necessary, the above-mentioned water-soluble organic solvent, an ink conditioner and the like to purified water such as distilled water.
• the present invention is applied to a mixture of water and the above-mentioned water-soluble organic solvent, ink conditioner, etc.
• a light compound or a salt thereof may be added and dissolved. If necessary, filtration may be performed after obtaining the ink composition to remove contaminants.
• water-soluble organic solvents that can be used include, for example, CI to C4 alcohols such as methanol, ethanol, propanol, isopropanol, butanol, isobutanol, second butanol, and tert-butanol; Carboxylic acid amides such as N, N-dimethylformamide or N, N-dimethylacetamide; lactams such as N-methylpiperidin-12-one; 1,3-dimethylimidazolidine-12-one or 1 Cyclic urea such as 2,3-dimethylhexahydropyrimido-2-one, ketone or keto alcohol such as acetone, methylethylketone, 2-methyl-12-hydroxypentane-4-one, tetrahydrofuran, dioxane, etc.
• CI to C4 alcohols such as methanol, ethanol, propanol, isopropanol, butanol, isobutanol,
• Ether ethylene glycol, 1,2_ or 1,3-propylene glycol, 1,2- or 1,4-butylene glycol, 1 Mono-, oligo- or polyalkylene dalicol or tiodic alcohol having C2-C6 alkylene units such as 6-hexylene glycol, diethylene dallyol, triethylene glycol, dipropylene glycol, thiodiglycol, polyethylene glycol, polypropylene glycol, etc.
• Glycerin hexane-polyols such as 1,2,6-triol (triol), ethylene daryl glycol monomethyl ether, ethylene glycol monoethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, triethylene CI to C4 alkyl ethers of polyhydric alcohols such as glycol monomethyl ether, triethylene glycol-monoethyl ether, ⁇ -butyrolactone or dimethyl sulfoxy Etc.
• hexane-polyols such as 1,2,6-triol (triol)
• ethylene daryl glycol monomethyl ether ethylene glycol monoethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, triethylene CI to C4 alkyl ethers of polyhydric alcohols such as glycol monomethyl ether, triethylene glycol-monoethyl ether, ⁇ -butyrolactone or di
• Preferred organic solvents miscible with water include ⁇ ⁇ ⁇ -methylpyrrolidin-2-one, mono-, di- or trialkylene glycols having a C 2 -C 6 alkylene unit, and preferred are mono-, di- or tri-alkylene glycols. Examples thereof include ethylene glycol, dipropylene calendar, and dimethyl sulfoxide. In particular, use of N-methylpyrrolidin-2-one, diethylenedaricol, and dimethyl sulfoxide is preferred.
• the ink conditioner is preferably used in an aqueous solution containing the compound (colorant component) of the present invention.
• used for the purpose of imparting ink suitability such as antiseptics and fungicides, PH regulators, chelating reagents, antioxidants, water-soluble ultraviolet absorbers, water-soluble polymer compounds, dye dissolving agents, surfactants, etc. Is mentioned.
• the antiseptic / antifungal agent include sodium dehydroacetate, sodium sorbate, sodium 2-pyridinethiol-l-oxide, sodium benzoate, sodium pentachlorophenol and the like.
• any substance can be used as long as it can control the pH of the ink, preferably to a range of 6 to 11, without adversely affecting the ink to be prepared.
• alkanolamines such as diethanolamine and triethanolamine
• hydroxides of alkali metal elements such as lithium hydroxide, sodium hydroxide and potassium hydroxide, ammonium hydroxide, or lithium carbonate and carbonate.
• alkali metal carbonates such as sodium and potassium carbonate.
• the chelating reagent include sodium ethylenediaminetetraacetate, sodium triacetate, sodium hydroxyethylethylenediaminetriacetate, sodium diethylenetriaminepentaacetate, and sodium peramyldiacetate.
• Examples of the protective agent include acid sulfite, sodium thiosulfate, ammonium thiodarcholate, diisopropylammonium nitrite, pentaerythritol tetranitrate, and dicyclohexylammonium nitrite.
• Examples of the dye dissolving agent include ⁇ -force prolactam, urea, and ethylene carbonate.
• Examples of the surfactant include ordinary anionic, cationic, and nonionic surfactants.
• Examples of the recording material in the ink jet recording method of the present invention include, for example, an information transmission sheet such as paper and film, a fiber, and leather.
• the information transmission sheet is preferably a surface-treated sheet, specifically, a sheet in which an ink receiving layer is provided 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 coating inorganic fine particles such as porous silica, alumina sol and special ceramics capable of adsorbing dyes in the ink with polyvinyl alcohol-polypropylene. It is provided by coating the substrate surface together with a hydrophilic polymer such as vinylpyrrolidone.
• the one provided with such an ink receiving layer is usually an inkjet It is called special paper (film) or glossy paper (film).
• Pictorico made by Asahi Glass
• Color BJ paper color BJ photo film sheet (all manufactured by Canon)
• Color Image Jet paper Sharp
• Super Fine glossy film Seiko Epson
• Pictafine Hitachi Maxell
• the fibers are preferably cellulose fibers or polyamide fibers such as nylon, silk and wool, and are preferably nonwoven fabrics or cloths.
• wet heat for example, about 80 to 120 ° C
• dry heat for example, about 1
• a dye can be dyed inside the fiber, and a dyed article having excellent clarity, light fastness and washing resistance can be obtained.
• the container of the present invention contains the aqueous magenta ink composition described above.
• the ink jet pudding of the present invention has a container of the present invention containing the aqueous magenta ink composition set in an ink tank portion.
• the colored body of the present invention is a novel anthrapyridone compound represented by the above formulas (1) and (2) or a salt thereof, preferably colored with the above aqueous magenta ink composition.
• the water-based ink composition of the present invention has a clear, nearly ideal magenta color, and can be used in combination with other yellow and cyan inks to produce a color tone in a wide visible region, and has lightfastness. When used in combination with existing yellow, cyan, and black, which have excellent water resistance, it is possible to obtain a recorded matter having excellent light resistance, water resistance, and gas resistance.
• 1.8 parts of 28% ammonia water was added to the reaction solution, and the mixture was reacted at 10 to 15 for 2 hours and at 25 to 30 for 1 hour to obtain a reaction solution containing a secondary condensate.
• Each liquid was prepared by preparing a liquid having the composition shown in Table 2 below containing the anthrapyridone compound (dye component) of the present invention obtained in Examples 1 and 2, and filtering it through a 0.45 m membrane filter.
• a water-based magenta ink composition was obtained.
• the water used was ion-exchanged water.
• Water and ammonium hydroxide were added so that the pH of the ink composition was 8 to 10 and the total amount was 100 parts.
• Table 3 shows the hues of one sample of the standard mazen evening color of JNC JAPAN Co 1 or. Table 3
• Paper is Japan Color Standard Paper
• the recorded image was irradiated for 50 hours at 24 ° C. and 60% RH using a xenon weather meter (manufactured by Atlas).
• the color difference ( ⁇ ⁇ ) before and after irradiation was measured using the above colorimetric system for the change before and after irradiation. The results are shown in Table 4.
• test piece printed on the recorded image was left at 40 t :, 4 ppm for 10 hours using an ozone weather meter (manufactured by Suga Test Instruments Co., Ltd.), and the color difference ( ⁇ ) before and after the test was measured.
• ⁇ color difference
• thermo-hygrostat manufactured by Applied Giken Sangyo Co., Ltd.
• Table 4 shows the results determined in three steps. Table 4 shows the results of the hue, sharpness, light fastness, ozone fastness and moisture fastness test of the recorded images. In addition, the result of evaluating the ink composition prepared using the compound obtained in Example 1 was evaluated, and the result of evaluating the ink composition prepared using the compound obtained in Example 2 in the same manner as in Evaluation Example 1 was evaluated. Is referred to as Evaluation Example 2. Further, as Comparative Example 1, an anthrapyridone compound (compound of No. 4) of Example 2 of JP-A-2000-109464, and Table 4 also shows the results of evaluation using the anthrapyridone compound (compound of the formula (1)) of Synthesis Example 1 of JP-A-2000-169776 as Comparative Example 2 and Comparative Example 2. Table 4
• Example 3 The result of evaluating the ink composition produced using the obtained compound was evaluated as Evaluation Example 3, and the result of evaluating the ink composition manufactured using the compound obtained in Example 4 was evaluated as Evaluation Example 4.
• Table 5 shows the results of the hue, clarity, light fastness, ozone fastness, and humidity fastness tests of the recorded images of the aqueous magenta ink compositions of Evaluation Examples 3 and 4.
• the anthrapyridone compound of the present invention is similar to the JNC standard magenta color and sharpness, and is a compound suitable as a magenta dye for inkjet. Also, The C * value is higher than that of the JNC standard magenta, and the sharpness is higher.
• the light fastness of the product of the present invention is smaller than that of the comparative example and can be evaluated as high light fastness magenta.
• the ozone resistance of the product of the present invention is smaller than those of the comparative examples in all ⁇ ⁇ values, indicating that a surprising improvement in ozone gas durability has been achieved.
• the anthrapyridone compound of the present invention is extremely useful as a magenta ink for ink jet recording with improved moisture resistance while maintaining high light resistance. Was obtained.
• the novel anthrapyridone compound of the present invention has the characteristics that it is extremely excellent in water solubility, the aqueous solution has good stability over time, and the filterability of the membrane filter during the ink composition manufacturing process is good. Furthermore, this compound is highly safe for living organisms. Furthermore, the ink composition of the present invention using the novel anthrapyridone compound has good storage stability without crystal precipitation, change in physical properties, color change, etc. after long-term storage. Further, printed matter using the ink composition of the present invention as a magenta ink for inkjet recording is excellent in light fastness, ozone fastness and moisture fastness, and enables excellent ink jet recording.
• the print surface is clear and almost ideal magenta-yellow, and when used with other yellow and cyan inks, it is possible to colorize a wide visible region.
• the ink composition of the present invention is extremely useful as a magenta ink for inkjet recording.

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• 2002
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• 2005
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