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WO2015141362A1 - Composé, composition colorante, encre pour l'impression par jet d'encre, procédé d'impression par jet d'encre, cartouche d'imprimante à jet d'encre et produit imprimé par jet d'encre - Google Patents

Composé, composition colorante, encre pour l'impression par jet d'encre, procédé d'impression par jet d'encre, cartouche d'imprimante à jet d'encre et produit imprimé par jet d'encre Download PDF

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Publication number
WO2015141362A1
WO2015141362A1 PCT/JP2015/054440 JP2015054440W WO2015141362A1 WO 2015141362 A1 WO2015141362 A1 WO 2015141362A1 JP 2015054440 W JP2015054440 W JP 2015054440W WO 2015141362 A1 WO2015141362 A1 WO 2015141362A1
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Prior art keywords
group
ink
substituted
inkjet
carbon atoms
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PCT/JP2015/054440
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English (en)
Japanese (ja)
Inventor
隆史 飯泉
立石　桂一
和史 古川
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Fujifilm Corp
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Fujifilm Corp
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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
    • C09B31/00—Disazo and polyazo dyes of the type A->B->C, A->B->C->D, or the like, prepared by diazotising and coupling
    • C09B31/02—Disazo dyes
    • C09B31/12—Disazo dyes from other coupling components "C"
    • C09B31/14—Heterocyclic components
    • C09B31/153—Heterocyclic components containing a six-membered ring with one nitrogen atom as the only ring hetero-atom
    • 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
    • C09B33/00—Disazo and polyazo dyes of the types A->K<-B, A->B->K<-C, or the like, prepared by diazotising and coupling
    • C09B33/02—Disazo dyes
    • C09B33/12—Disazo dyes in which the coupling component is a heterocyclic compound

Definitions

  • the present invention relates to a compound, a coloring composition, an ink for ink jet recording, an ink jet recording method, an ink jet printer cartridge, and an ink jet recorded matter.
  • the ink jet recording method is rapidly spreading and further developing because of its low material cost, high speed recording, low noise during recording, and easy color recording.
  • Inkjet recording methods include a continuous method in which droplets are continuously ejected and an on-demand method in which droplets are ejected in accordance with image information signals.
  • There are a method for ejecting droplets a method for generating bubbles in ink by discharging heat, a method for discharging droplets, a method using ultrasonic waves, and a method for attracting and discharging droplets by electrostatic force.
  • As the ink for ink jet recording water-based ink, oil-based ink, or solid (melted type) ink is used.
  • Patent Document 1 describes that an azo compound having a specific structure has an excellent hue as a black ink, can suppress the occurrence of bronze gloss, and can provide an image excellent in light resistance and ozone resistance. .
  • Patent Document 1 exhibits excellent performance as described above, but there is room for further performance improvement regarding the storage stability of the ink containing the azo compound.
  • An object of the present invention is to provide a compound that can form an image excellent in light resistance and ozone resistance and capable of forming an image with suppressed bronze gloss and having excellent storage stability.
  • Another object of the present invention is to provide a coloring composition containing the compound, an ink for ink jet recording, an ink jet recording method using the ink for ink jet recording, an ink jet printer cartridge, and an ink jet recorded matter.
  • R represents a substituted or unsubstituted alkyl group or a halogen atom.
  • G represents a nitrogen atom or —C (R 2 ) ⁇ .
  • R 2 represents a hydrogen atom, a sulfo group, a carboxy group, a substituted or unsubstituted carbamoyl group, or a cyano group.
  • R 11 , R 12 , R 13 and R 14 each independently represent a hydrogen atom or a substituent.
  • M represents a hydrogen atom or a counter cation each independently.
  • R 11 , R 12 , R 13 and R 14 are each independently a hydrogen atom, The compound according to [1] or [2], which is an alkyl group substituted with a halogen atom, a hydroxyl group or an ionic hydrophilic group, or an aryl group substituted with a halogen atom, a hydroxyl group or an ionic hydrophilic group.
  • [4] The compound according to any one of [1] to [3], wherein G represents —C (R 2 ) ⁇ and R 2 represents a cyano group.
  • M represents a lithium ion, a potassium ion or a sodium ion.
  • [6] [1] A coloring composition comprising the compound according to any one of [5]. [7] [1] An ink for ink-jet recording containing the compound according to any one of [5]. [8] An ink jet recording method using the ink for ink jet recording according to [7]. [9] An ink jet printer cartridge filled with the ink for ink jet recording according to [7]. [10] An ink-jet recorded matter in which a colored image is formed on a recording material using the ink for ink-jet recording described in [7].
  • the compound which can form the image which is excellent in light resistance and ozone resistance, can suppress the bronze glossiness, and can prepare the ink which is excellent in storage stability can be provided.
  • the coloring composition containing this compound, the inkjet recording ink, the inkjet recording method using the inkjet recording ink, an inkjet printer cartridge, and an inkjet recorded matter can be provided.
  • halogen atom examples include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
  • alkyl group examples include linear, branched, and cyclic substituted or unsubstituted alkyl groups, and include cycloalkyl groups, bicycloalkyl groups, and tricyclo structures having many ring structures.
  • An alkyl group (for example, an alkyl group of an alkoxy group or an alkylthio group) in a substituent described below also represents such an alkyl group.
  • an alkyl group having 1 to 30 carbon atoms such as a methyl group, an ethyl group, an n-propyl group, an i-propyl group, a t-butyl group, an n-octyl group, an eicosyl group, 2- Examples thereof include a chloroethyl group, a 2-cyanoethyl group, a 2-ethylhexyl group, etc.
  • the cycloalkyl group is preferably a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, such as a cyclohexyl group, a cyclopentyl group, 4 -N-dodecylcyclohexyl group and the like
  • the bicycloalkyl group is preferably a substituted or unsubstituted bicycloalkyl group having 5 to 30 carbon atoms, that is, one hydrogen atom from a bicycloalkane having 5 to 30 carbon atoms.
  • Monovalent groups removed such as bicyclo [1,2,2] heptan-2-yl group, bicyclo [2,2 2] octan-3-yl group.
  • aralkyl group examples include a substituted or unsubstituted aralkyl group, and the substituted or unsubstituted aralkyl group is preferably an aralkyl group having 7 to 30 carbon atoms. Examples thereof include a benzyl group and a 2-phenethyl group.
  • alkenyl group examples include linear, branched, and cyclic substituted or unsubstituted alkenyl groups, and include cycloalkenyl groups and bicycloalkenyl groups.
  • Preferred examples of the alkenyl group include substituted or unsubstituted alkenyl groups having 2 to 30 carbon atoms such as vinyl group, allyl group, prenyl group, geranyl group, and oleyl group.
  • cycloalkenyl group examples include Is a substituted or unsubstituted cycloalkenyl group having 3 to 30 carbon atoms, that is, a monovalent group obtained by removing one hydrogen atom of a cycloalkene having 3 to 30 carbon atoms, such as a 2-cyclopenten-1-yl group, 2-cyclohexen-1-yl group and the like.
  • bicycloalkenyl group a substituted or unsubstituted bicycloalkenyl group, preferably a substituted or unsubstituted bicycloalkenyl group having 5 to 30 carbon atoms, that is, a double bond
  • the alkynyl group is preferably a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, such as an ethynyl group, a propargyl group, a trimethylsilylethynyl group, and the like.
  • the aryl group is preferably a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, such as a phenyl group, a p-tolyl group, a naphthyl group, an m-chlorophenyl group, an o-hexadecanoylaminophenyl group, and the like. Can be mentioned.
  • the heterocyclic group is preferably a monovalent group obtained by removing one hydrogen atom from a 5- or 6-membered substituted or unsubstituted aromatic or non-aromatic heterocyclic compound, and more preferably a carbon number.
  • Examples thereof include 3 to 30 5- or 6-membered aromatic heterocyclic groups such as a 2-furyl group, a 2-thienyl group, a 2-pyrimidinyl group, and a 2-benzothiazolyl group.
  • non-aromatic heterocyclic groups include morpholinyl groups.
  • the alkoxy group is preferably a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, such as a methoxy group, an ethoxy group, an isopropoxy group, a t-butoxy group, an n-octyloxy group, or a 2-methoxyethoxy group. Etc.
  • the aryloxy group is preferably a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, such as a phenoxy group, 2-methylphenoxy group, 4-t-butylphenoxy group, 3-nitrophenoxy group, 2 -Tetradecanoylaminophenoxy group and the like.
  • silyloxy group examples include substituted or unsubstituted silyloxy groups having 0 to 20 carbon atoms, such as trimethylsilyloxy group and diphenylmethylsilyloxy group.
  • the heterocyclic oxy group is preferably a substituted or unsubstituted heterocyclic oxy group having 2 to 30 carbon atoms, such as a 1-phenyltetrazol-5-oxy group and a 2-tetrahydropyranyloxy group.
  • the acyloxy group is preferably a formyloxy group, a substituted or unsubstituted alkylcarbonyloxy group having 2 to 30 carbon atoms, a substituted or unsubstituted arylcarbonyloxy group having 6 to 30 carbon atoms, such as an acetyloxy group, Examples include pivaloyloxy group, stearoyloxy group, benzoyloxy group, p-methoxyphenylcarbonyloxy group and the like.
  • the carbamoyloxy group is preferably a substituted or unsubstituted carbamoyloxy group having 1 to 30 carbon atoms, such as N, N-dimethylcarbamoyloxy group, N, N-diethylcarbamoyloxy group, morpholinocarbonyloxy group, N , N-di-n-octylaminocarbonyloxy group, Nn-octylcarbamoyloxy group and the like.
  • the alkoxycarbonyloxy group is preferably a substituted or unsubstituted alkoxycarbonyloxy group having 2 to 30 carbon atoms, such as a methoxycarbonyloxy group, an ethoxycarbonyloxy group, a t-butoxycarbonyloxy group, or an n-octylcarbonyloxy group. Etc.
  • aryloxycarbonyloxy group a substituted or unsubstituted aryloxycarbonyloxy group having 7 to 30 carbon atoms such as phenoxycarbonyloxy group, p-methoxyphenoxycarbonyloxy group, pn-hexadecyloxy is preferable. Examples include phenoxycarbonyloxy group.
  • the amino group includes an alkylamino group, an arylamino group, and a heterocyclic amino group, preferably an amino group, a substituted or unsubstituted alkylamino group having 1 to 30 carbon atoms, a substituted or unsubstituted group having 6 to 30 carbon atoms.
  • the substituted anilino group include a methylamino group, a dimethylamino group, an anilino group, an N-methyl-anilino group, a diphenylamino group, and a triazinylamino group.
  • the acylamino group is preferably a formylamino group, a substituted or unsubstituted alkylcarbonylamino group having 1 to 30 carbon atoms, a substituted or unsubstituted arylcarbonylamino group having 6 to 30 carbon atoms, such as an acetylamino group, Examples include pivaloylamino group, lauroylamino group, benzoylamino group, 3,4,5-tri-n-octyloxyphenylcarbonylamino group, and the like.
  • the aminocarbonylamino group is preferably a substituted or unsubstituted aminocarbonylamino group having 1 to 30 carbon atoms, such as a carbamoylamino group, N, N-dimethylaminocarbonylamino group, N, N-diethylaminocarbonylamino group. And a morpholinocarbonylamino group.
  • the alkoxycarbonylamino group is preferably a substituted or unsubstituted alkoxycarbonylamino group having 2 to 30 carbon atoms, such as a methoxycarbonylamino group, an ethoxycarbonylamino group, a t-butoxycarbonylamino group, or an n-octadecyloxycarbonylamino group. Group, N-methyl-methoxycarbonylamino group and the like.
  • the aryloxycarbonylamino group is preferably a substituted or unsubstituted aryloxycarbonylamino group having 7 to 30 carbon atoms, such as phenoxycarbonylamino group, p-chlorophenoxycarbonylamino group, mn-octyloxyphenoxy. Examples thereof include a carbonylamino group.
  • the sulfamoylamino group is preferably a substituted or unsubstituted sulfamoylamino group having 0 to 30 carbon atoms, such as a sulfamoylamino group, N, N-dimethylaminosulfonylamino group, Nn- Examples include octylaminosulfonylamino group.
  • the alkyl or arylsulfonylamino group is preferably a substituted or unsubstituted alkylsulfonylamino group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsulfonylamino group having 6 to 30 carbon atoms, such as a methylsulfonylamino group.
  • the alkylthio group is preferably a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, such as a methylthio group, an ethylthio group, and an n-hexadecylthio group.
  • the arylthio group is preferably a substituted or unsubstituted arylthio group having 6 to 30 carbon atoms, such as a phenylthio group, a p-chlorophenylthio group, and an m-methoxyphenylthio group.
  • heterocyclic thio group examples include substituted or unsubstituted heterocyclic thio groups having 2 to 30 carbon atoms, such as 2-benzothiazolylthio group and 1-phenyltetrazol-5-ylthio group.
  • the sulfamoyl group is preferably a substituted or unsubstituted sulfamoyl group having 0 to 30 carbon atoms, such as N-ethylsulfamoyl group, N- (3-dodecyloxypropyl) sulfamoyl group, N, N-dimethylsulfuryl group.
  • Examples include a famoyl group, an N-acetylsulfamoyl group, an N-benzoylsulfamoyl group, and an N- (N′-phenylcarbamoyl) sulfamoyl group.
  • the alkyl or arylsulfinyl group is preferably a substituted or unsubstituted alkylsulfinyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsulfinyl group having 6 to 30 carbon atoms, such as a methylsulfinyl group or an ethylsulfinyl group. , Phenylsulfinyl group, p-methylphenylsulfinyl group and the like.
  • the alkyl or arylsulfonyl group is preferably a substituted or unsubstituted alkylsulfonyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsulfonyl group having 6 to 30 carbon atoms, such as a methylsulfonyl group or an ethylsulfonyl group. , Phenylsulfonyl group, p-methylphenylsulfonyl group and the like.
  • the acyl group is preferably a formyl group, a substituted or unsubstituted alkylcarbonyl group having 2 to 30 carbon atoms, a substituted or unsubstituted arylcarbonyl group having 7 to 30 carbon atoms, a substituted or unsubstituted group having 2 to 30 carbon atoms.
  • Heterocyclic carbonyl groups bonded to carbonyl groups at substituted carbon atoms eg, acetyl, pivaloyl, 2-chloroacetyl, stearoyl, benzoyl, pn-octyloxyphenylcarbonyl, 2-pyridyl
  • Examples thereof include a carbonyl group and a 2-furylcarbonyl group.
  • the aryloxycarbonyl group is preferably a substituted or unsubstituted aryloxycarbonyl group having 7 to 30 carbon atoms, such as a phenoxycarbonyl group, an o-chlorophenoxycarbonyl group, an m-nitrophenoxycarbonyl group, pt- A butylphenoxycarbonyl group etc. are mentioned.
  • the alkoxycarbonyl group is preferably a substituted or unsubstituted alkoxycarbonyl group having 2 to 30 carbon atoms, such as a methoxycarbonyl group, an ethoxycarbonyl group, a t-butoxycarbonyl group, and an n-octadecyloxycarbonyl group.
  • the carbamoyl group is preferably a substituted or unsubstituted carbamoyl group having 1 to 30 carbon atoms, such as a carbamoyl group, an N-methylcarbamoyl group, an N, N-dimethylcarbamoyl group, or an N, N-di-n-octyl group.
  • a carbamoyl group, an N- (methylsulfonyl) carbamoyl group, and the like can be given.
  • the aryl or heterocyclic azo group is preferably a substituted or unsubstituted arylazo group having 6 to 30 carbon atoms, a substituted or unsubstituted heterocyclic azo group having 3 to 30 carbon atoms, such as a phenylazo group, p-chlorophenylazo Group, 5-ethylthio-1,3,4-thiadiazol-2-ylazo group and the like.
  • Preferred examples of the imide group include an N-succinimide group and an N-phthalimide group.
  • the phosphino group is preferably a substituted or unsubstituted phosphino group having 0 to 30 carbon atoms, such as a dimethylphosphino group, a diphenylphosphino group, a methylphenoxyphosphino group, and the like.
  • the phosphinyl group is preferably a substituted or unsubstituted phosphinyl group having 0 to 30 carbon atoms, such as a phosphinyl group, a dioctyloxyphosphinyl group, a diethoxyphosphinyl group, and the like.
  • the phosphinyloxy group is preferably a substituted or unsubstituted phosphinyloxy group having 0 to 30 carbon atoms, such as a diphenoxyphosphinyloxy group and a dioctyloxyphosphinyloxy group.
  • the phosphinylamino group is preferably a substituted or unsubstituted phosphinylamino group having 0 to 30 carbon atoms, such as a dimethoxyphosphinylamino group or a dimethylaminophosphinylamino group.
  • silyl group examples include substituted or unsubstituted silyl groups having 0 to 30 carbon atoms, such as a trimethylsilyl group, a t-butyldimethylsilyl group, and a phenyldimethylsilyl group.
  • Examples of the ionic hydrophilic group include a sulfo group, a carboxyl group, a thiocarboxyl group, a sulfino group, a phosphono group, a dihydroxyphosphino group, and a quaternary ammonium group. Particularly preferred are a sulfo group and a carboxyl group.
  • the carboxyl group, phosphono group and sulfo group may be in the form of a salt.
  • Examples of counter cations that form a salt include ammonium ion, alkali metal ion (eg, lithium ion, sodium ion, potassium ion) and organic.
  • Cation eg, tetramethylammonium ion, tetramethylguanidinium ion, tetramethylphosphonium
  • lithium salt, sodium salt, potassium salt, ammonium salt is preferable
  • lithium salt or mixed salt containing lithium salt as a main component Are more preferred, and lithium salts are most preferred.
  • (Substituent group B) Straight or branched alkyl group having 1 to 12 carbon atoms, straight or branched aralkyl group having 7 to 18 carbon atoms, straight or branched alkenyl group having 2 to 12 carbon atoms, straight chain having 2 to 12 carbon atoms Or a branched alkynyl group, a cycloalkyl group having 3 to 12 carbon atoms, a cycloalkenyl group having 3 to 12 carbon atoms (for example, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, sec-butyl) , T-butyl, 2-ethylhexyl, 2-methylsulfonylethyl, 3-phenoxypropyl, trifluoromethyl, cyclopentyl), halogen atom (eg, chlorine atom, bromine atom), aryl group (eg, phenyl, 4-
  • R represents a substituted or unsubstituted alkyl group or a halogen atom.
  • G represents a nitrogen atom or —C (R 2 ) ⁇ .
  • R 2 represents a hydrogen atom, a sulfo group, a carboxy group, a substituted or unsubstituted carbamoyl group, or a cyano group.
  • R 11 , R 12 , R 13 and R 14 each independently represent a hydrogen atom or a substituent.
  • M represents a hydrogen atom or a counter cation each independently.
  • the compound represented by the general formula (1) has a cyano group in the ortho position with respect to the azo group of the phenyl group bonded to the azo group, and a substituted or unsubstituted alkyl group or halogen atom in the para position. It is considered that an ink having excellent storage stability can be obtained. The details of this mechanism of action are not clear, but it is considered that a hydrophobic substituted or unsubstituted alkyl group or halogen atom at the para position makes it difficult for nucleophiles such as hydrophilic water to approach.
  • R represents a substituted or unsubstituted alkyl group or a halogen atom.
  • R is preferably an alkyl group having 1 to 10 carbon atoms or a halogen atom.
  • the alkyl group is preferably an alkyl group having 1 to 10 carbon atoms, more preferably an alkyl group having 1 to 6 carbon atoms, and an alkyl group having 1 to 4 carbon atoms. Further preferred.
  • a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, and a t-butyl group are preferable, and a methyl group, an ethyl group, an isopropyl group, and a tert-butyl group are preferable.
  • a butyl group is more preferable, and a methyl group is still more preferable.
  • the alkyl group may have a substituent, and the substituent in the case of having a substituent includes a substituent selected from the above-mentioned substituent group A, and includes an amino group and an alkylamino group (preferably having 1 carbon atom).
  • an arylamino group having 6 to 10 carbon atoms More preferably an arylamino group having 6 to 10 carbon atoms, more preferably a phenylamino group or a cyanophenylamino group), a hydroxyl group or an alkoxy group (preferably an alkoxy group having 1 to 12 carbon atoms).
  • an alkoxy group having 1 to 6 carbon atoms more preferably an ethoxy group or a methoxy group
  • an arylthio group Preferably, it is an arylthio group having 6 to 20 carbon atoms, more preferably an arylthio group having 6 to 10 carbon atoms, more preferably a phenylthio group or an ethylbenzenethio group, and an alkylthio group (preferably having a carbon number of 1 to 20).
  • An alkylthio group having 1 to 10 carbon atoms more preferably a methylthio group and an ethylthio group, and an alkylsulfonyl group (preferably an alkylsulfonyl group having 1 to 10 carbon atoms, and more An alkylsulfonyl group having 1 to 6 carbon atoms is preferable, and a methanesulfonyl group and an ethanesulfonyl group are more preferable.
  • R represents a halogen atom
  • G represents a nitrogen atom or —C (R 2 ) ⁇ .
  • R 2 represents a hydrogen atom, a sulfo group, a carboxy group, a substituted or unsubstituted carbamoyl group, or a cyano group.
  • the substituent is an alkyl group (preferably an alkyl group having 1 to 6 carbon atoms, more preferably an alkyl group having 1 to 4 carbon atoms, and particularly preferably a methyl group or ethyl group).
  • Group and an aryl group (preferably an aryl group having 6 to 8 carbon atoms, more preferably a phenyl group).
  • R 2 is preferably a carboxy group, a substituted or unsubstituted carbamoyl group or a cyano group, and more preferably a cyano group.
  • G preferably represents a nitrogen atom or —C (CN) ⁇ , and more preferably —C (CN) ⁇ .
  • R 11 , R 12 , R 13 and R 14 each independently represent a hydrogen atom or a substituent. It is preferable that one of R 11 and R 12 represents a hydrogen atom and the other represents a substituent. It is preferable that one of R 13 and R 14 represents a hydrogen atom and the other represents a substituent. Preferred examples of R 11 , R 12 , R 13 and R 14 include a hydrogen atom or a substituent selected from the above substituent group B.
  • alkyl group include alkyl groups having 1 to 10 carbon atoms, such as methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, or t-butyl group.
  • a methyl group, an ethyl group, or an n-propyl group is more preferable, and an ethyl group is still more preferable.
  • the aryl group include an aryl group having 6 to 20 carbon atoms, and a phenyl group and a naphthyl group are preferable, and a phenyl group is more preferable.
  • the ionic hydrophilic group is preferably a sulfo group, a carboxyl group or a hydroxy group, more preferably a sulfo group, a lithium salt of a sulfo group (—SO 3 Li), a sodium salt of a sulfo group (—SO 3 Na), or a sulfo group
  • a lithium salt of a sulfo group —SO 3 Li
  • —SO 3 Na a sodium salt of a sulfo group
  • the potassium salt of the group (—SO 3 K) is more preferred, and the lithium salt of the sulfo group (—SO 3 Li) is particularly preferred.
  • R 11 , R 12 , R 13 and R 14 represent substituents are shown below, but the present invention is not limited thereto. * Represents a bonding position.
  • M represents a hydrogen atom or a counter cation each independently.
  • the counter cation include ammonium ion, alkali metal ion (for example, lithium ion, sodium ion, potassium ion) and organic cation (for example, tetramethylammonium ion, tetramethylguanidinium ion, tetramethylphosphonium).
  • M preferably represents a counter cation, more preferably represents an alkali metal ion or ammonium ion, more preferably represents an alkali metal ion, particularly preferably represents a lithium ion, potassium ion or sodium ion, and lithium ion Most preferably, is represented.
  • Me represents a methyl group.
  • the compound represented by the general formula (1) can be synthesized by a coupling reaction between a diazo component and a coupler, and for these, JP 2012-177073 A, JP 2003-306623 A, and JP-A-2005-139427 describes it.
  • the compound represented by the general formula (1) can be made into an aqueous solution by dissolving water in a main solvent.
  • the aqueous solution containing the compound (pigment) represented by the general formula (1) is prepared by dissolving in an aqueous medium when the dye is water-soluble, and lipophilic when the dye is oil-soluble. It is preferable to prepare by dissolving and / or dispersing in a medium and / or an aqueous medium.
  • the aqueous medium is a solvent mainly containing water, and optionally contains an organic solvent such as a water-miscible organic solvent. This organic solvent may have a function as a viscosity reducing agent.
  • the lipophilic medium is mainly composed of an organic solvent.
  • the main solvent is water, preferably the water content in the total solvent is 50% by mass to 100% by mass, more preferably the water content in the total solvent is 60% by mass to 100% by mass. It is.
  • the aqueous solution may contain a water-miscible organic solvent and a lipophilic medium in addition to water.
  • the compound represented by the general formula (1) is dissolved or dispersed in the solvent, preferably dissolved.
  • the content of the compound represented by the general formula (1) is preferably 1% by mass to 25% by mass and more preferably 2% by mass to 20% by mass with respect to the total mass of the aqueous solution. More preferably, it is 2 to 15% by mass.
  • the aqueous solution preferably has a pH of 7.0 to 9.0 at 25 ° C., more preferably 7.5 to 8.5.
  • the aqueous solution may be referred to as “ink stock solution”.
  • the use of the aqueous solution is not particularly limited, but is preferably used for inkjet.
  • a preservative In the aqueous solution, generation of insoluble matter due to decay may be a problem. In order to prevent this, a preservative can be added to the aqueous solution.
  • Various preservatives that can be used in the present invention can be used. Examples of the preservative include inorganic preservatives (such as silver ion-containing substances) and salts containing heavy metal ions.
  • Organic preservatives include quaternary ammonium salts (tetrabutylammonium chloride, cetylpyridinium chloride, benzyltrimethylammonium chloride, etc.), phenol derivatives (phenol, cresol, butylphenol, xylenol, bisphenol, etc.), phenoxyether derivatives (phenoxyethanol) Etc.), heterocyclic compounds (benzotriazole, proxel, 1,2-benzisothiazolin-3-one, etc.), acid amides, carbamic acid, carbamates, amidine / guanidine, pyridines (sodium pyridinethione- 1-oxide, etc.), diazines, triazines, pyrrole / imidazoles, oxazoles / oxazines, thiazoles / thiadiazines, thioureas, thiosemicarbazides , Dithiocarbamates, sulfides, sul
  • the antiseptic those described in the antibacterial and microscopic handbook (Technical Hall: 1986), the antibacterial and antifungal encyclopedia (edited by the Japanese Society for Antibacterial and Antifungal Society), etc. can be used.
  • the preservative a phenol derivative and a heterocyclic compound are preferable, a heterocyclic compound is more preferable, and a heterocyclic compound (Proxel XL-II: manufactured by Fujifilm Imaging Colorant) is further preferable.
  • Preservatives can be added singly or in combination of two or more.
  • Various preservatives such as oil-soluble structures and water-soluble structures can be used, but water-soluble preservatives are preferred.
  • At least one preservative is a heterocyclic compound.
  • the effect of the present invention is more satisfactorily exhibited.
  • the combination of a heterocyclic compound and an antibiotic, the combination of a heterocyclic compound and a phenol derivative, etc. are mentioned preferably.
  • the addition amount of the preservative to the aqueous solution can be used within a wide range, but is preferably 0.001 to 10% by mass, more preferably 0.1 to 5% by mass. By setting the content of the preservative within the above range, there is an effect of suppressing the growth of bacteria in the aqueous solution.
  • the aqueous solution may further contain a pH adjuster.
  • the aqueous solution may be adjusted to a more preferable hue by using another colorant together with the compound represented by the general formula (1).
  • Any dye can be used as the dye to be used in combination.
  • the coloring composition of this invention contains the compound represented by the said General formula (1).
  • the content of the compound represented by the general formula (1) in the coloring composition is preferably 0.2 to 20% by mass, more preferably 0.5 to 10% by mass, and 1.0 to 8.0% by mass. % Is particularly preferred.
  • the coloring composition of the present invention preferably contains 0.2 to 20% by mass of the total dye, more preferably 0.5 to 10% by mass, and particularly preferably 1.0 to 8.0% by mass. contains.
  • the pH of the coloring composition at 25 ° C. is preferably adjusted to 7.0 to 10.0 with a pH adjuster, and the pH is adjusted to 7.5 to 9.5. More preferably.
  • a pH adjuster used for a coloring composition lithium hydrogencarbonate, sodium hydrogencarbonate, and potassium hydrogencarbonate are preferable, and lithium hydrogencarbonate and sodium hydrogencarbonate are more preferable.
  • the use of the coloring composition of the present invention is not particularly limited, and is an ink composition for printing such as inkjet, an ink sheet in a thermal recording material, a color toner for electrophotography, an LCD, a display such as PDP, and the like.
  • an ink composition for inkjet recording is particularly preferable.
  • the said aqueous solution can be used for the manufacturing method of a coloring composition.
  • the coloring composition is preferably black ink, but should not be limited to black ink, and can include ink of any color by mixing with other dyes or pigments.
  • the manufacturing method of a coloring composition includes the process (henceforth a liquid preparation process) which produces the desired ink composition of the said viscosity range at least using aqueous solution.
  • the liquid preparation step is a step of preparing the aqueous solution obtained as described above into an ink composition having a specific viscosity and desired use, and may be a final product or an intermediate product. It may be.
  • This preparation step includes at least a step of diluting the aqueous solution with a medium, preferably an aqueous medium.
  • the aqueous solution containing the oil-soluble dye is not particularly limited in the medium used in this dilution step, but is preferably prepared as an aqueous ink composition by being emulsified and dispersed in an aqueous medium.
  • This medium may contain various components of a necessary concentration, or these components may be added separately to the aqueous solution, or both of them may be combined. Since the colored composition produced according to the present invention is produced using an aqueous solution having a high dye concentration, the solubility of the dye is improved as compared with the colored composition produced by a normal method, and thus the ejection stability is improved. improves.
  • the process which removes the dust which is solid content by filtration.
  • a filtration filter is used for this operation, and a filter having an effective diameter of 1 ⁇ m or less, preferably 0.3 ⁇ m or less is used as the filtration filter at this time.
  • Various materials can be used as the filter material, but in the case of an aqueous solution of a water-soluble dye, it is preferable to use a filter prepared for an aqueous solvent. Among them, it is particularly preferable to use a jacket type filter made of a polymer material that is difficult to generate dust.
  • the jacket may be passed by liquid feeding, and either pressure filtration or vacuum filtration can be used.
  • the viscosity reducing agent may be used and the said filtration process can be performed without resistance.
  • various methods such as dissolution by stirring, dissolution by ultrasonic irradiation, and dissolution by shaking can be used as a method for dissolving the dye and other components.
  • the stirring method is particularly preferably used.
  • various methods such as known fluidization agitation and agitation using shearing force using an inverted agitator or dissolver can be used.
  • a stirring method using a shearing force with the bottom surface of the container such as a magnetic stirrer, can also be preferably used.
  • the dye is not particularly limited, but the half-value width (W ⁇ , 1/2 ) in an absorption spectrum of a diluted solution having a ⁇ max of 500 nm to 700 nm and an absorbance normalized to 1.0 is 100 nm or more, preferably 120 nm. It is preferable to include at least one azo compound represented by the general formula (1) which is not less than 500 nm and more preferably not less than 120 nm and not more than 350 nm.
  • this dye can be used alone as a raw material for an aqueous solution or ink composition, but it is usually used in combination with a dye that covers a region where the absorption of this dye is low. It is common.
  • an ink composition using an azo compound represented by the general formula (1) it is preferably used in combination with another dye having a main absorption ( ⁇ max of 350 nm to 500 nm) in the yellow region.
  • Other dyes can be used in the aqueous solution, but are preferably mixed and used in preparation of the ink composition from the viewpoint of storage stability.
  • the coloring composition of the present invention may contain other additives as necessary within a range that does not impair the effects of the present invention.
  • other additives include additives that can be used in ink jet recording inks described later.
  • the ink for inkjet recording of the present invention contains the coloring composition of the present invention.
  • the ink for inkjet recording can be produced by dissolving and / or dispersing the compound represented by the general formula (1) in an oleophilic medium or an aqueous medium.
  • the ink uses an aqueous medium.
  • other additives can be contained within a range that does not impair the effects of the present invention.
  • additives include, for example, anti-drying agents (wetting agents), anti-fading agents, emulsion stabilizers, penetration enhancers, ultraviolet absorbers, preservatives, anti-fungal agents, pH adjusters, surface tension adjusters, Well-known additives, such as a foaming agent, a viscosity modifier, a dispersing agent, a dispersion stabilizer, a rust preventive agent, a chelating agent, are mentioned. These various additives are directly added to the ink liquid in the case of water-soluble ink. When an oil-soluble dye is used in the form of a dispersion, it is generally added to the dispersion after the preparation of the dye dispersion, but it may be added to the oil phase or the aqueous phase at the time of preparation.
  • the compound represented by the general formula (1) is preferably contained in an amount of 0.2% by mass or more and 10% by mass or less, and preferably 1% by mass or more and 6% by mass or less. Is more preferable.
  • other dyes may be used in combination with the compound represented by the general formula (1). When using 2 or more types of pigment
  • the ink for ink jet recording of the present invention preferably has a viscosity of 30 mPa ⁇ s or less.
  • the surface tension is preferably 25 mN / m or more and 70 mN / m or less.
  • Viscosity and surface tension are various additives such as viscosity modifiers, surface tension modifiers, specific resistance modifiers, film modifiers, UV absorbers, antioxidants, antifading agents, antifungal agents, and rust inhibitors. It can be adjusted by adding a dispersant and a surfactant.
  • the ink for inkjet recording of the present invention can be used not only for forming a single color image but also for forming a full color image.
  • it is preferably used for black ink-jet recording ink.
  • the ink composition of the present invention can be used for recording methods such as printing, copying, marking, writing, drawing, stamping and the like, and is particularly suitable for use in an ink jet recording method.
  • the present invention also relates to an inkjet recording method for forming an image using the colored composition or the inkjet recording ink of the present invention.
  • the ink cartridge for ink jet recording of the present invention is filled with the ink for ink jet recording of the present invention described above. Further, the ink-jet recorded matter of the present invention is obtained by forming a colored image on a recording material using the above-described ink for ink-jet recording of the present invention.
  • the support in recording paper and recording film is made of chemical pulp such as LBKP and NBKP, mechanical pulp such as GP, PGW, RMP, TMP, CTMP, CMPMP, CGP, and waste paper pulp such as DIP.
  • Additives such as known pigments, binders, sizing agents, fixing agents, cationic agents, paper strength enhancers, etc. can be mixed and manufactured using various devices such as long net paper machines and circular net paper machines. is there.
  • either synthetic paper or plastic film sheets may be used.
  • the thickness of the support is preferably 10 to 250 ⁇ m and the basis weight is preferably 10 to 250 g / m 2 .
  • Polymer latex may be added to the constituent layers (including the backcoat layer) of the inkjet recording paper and recording film.
  • the polymer latex is used for the purpose of improving film physical properties such as dimensional stabilization, curling prevention, adhesion prevention, and film cracking prevention.
  • the polymer latex is described in JP-A Nos. 62-245258, 62-136648, and 62-110066.
  • a polymer latex having a low glass transition temperature 40 ° C. or lower
  • cracking and curling of the layer can be prevented.
  • curling can be prevented by adding a polymer latex having a high glass transition temperature to the backcoat layer.
  • the ink of the present invention is not limited to an ink jet recording system, and is a known system, for example, a charge control system that discharges ink using electrostatic attraction, a drop-on-demand system (pressure) that uses the vibration pressure of a piezo element.
  • Pulse method acoustic ink jet method that converts electrical signal into acoustic beam and irradiates ink and uses ink to discharge ink
  • thermal ink jet that heats ink to form bubbles and uses generated pressure Used for systems.
  • Inkjet recording methods use a method of ejecting a large number of low-density inks called photo inks in a small volume, a method of improving image quality using a plurality of inks having substantially the same hue and different concentrations, and colorless and transparent inks. The method is included.
  • Lithium hydroxide was added to the reaction solution to adjust the pH to 8.0, and then 500 mL of isopropanol was added dropwise over 30 minutes.
  • the slurry reaction solution was filtered and washed with 200 mL of isopropanol to obtain crude (BLACK-1).
  • the crude product was dissolved by adding 40 mL of water, passed through a Li-type cation exchange resin, and then adjusted to pH 8.0 with a lithium hydroxide solution. After removing dust with a membrane filter to remove insolubles, the solution was concentrated with an evaporator to obtain 3.4 g of BLACK-1.
  • ⁇ max of the solution spectrum was 691 nm in DMF (dimethylformamide), 608 nm in water, molecular weight was 1282.10 by ESI-mass spectrum measurement, and it was confirmed by ion chromatography that the counter cation of sulfonic acid was lithium.
  • the crude product was dissolved by adding 50 mL of water, passed through a Li-type cation exchange resin, and then adjusted to pH 7.0 with a lithium hydroxide solution. After removing dust with a membrane filter to remove insolubles, the filtrate was concentrated with an evaporator to obtain 3.2 g of BLACK-2. ⁇ max of the solution spectrum was 707 nm in DMF, 613 nm in water, the molecular weight was 1302.05 by ESI-mass spectrum measurement, and it was confirmed by ion chromatography that the counter cation of sulfonic acid was lithium.
  • aqueous solution containing the coloring compound is herein referred to as “ink stock solution”.
  • the aqueous solution was adjusted to pH 8.1-8.3 using a 4 mol / L lithium hydroxide aqueous solution.
  • Example 1 100 g of the dye compound (BLACK-1) was dissolved in 900 g of ultrapure water with stirring at room temperature, and 0.1 g of a preservative (Proxel XL-II: manufactured by Fuji Film Imaging Colorant) was added as a solid content. The pH was adjusted to 8.2 using a 4 mol / L lithium hydroxide aqueous solution, and then unnecessary substances were filtered using a 0.2 ⁇ m membrane filter to obtain Ink Stock Solution-1.
  • a preservative Proxel XL-II: manufactured by Fuji Film Imaging Colorant
  • Example 2 An ink stock solution-2 was obtained in the same manner as in Example 1 except that (BLACK-2) was used instead of the dye compound (BLACK-1).
  • Comparative Example 1 A comparative ink stock solution-01 was obtained in the same manner as in Example 1, except that the following comparative compound 1 was used instead of the coloring compound (BLACK-1). Comparative compound 1
  • the ink stock solution is as follows based on the ABS value after dilution with ultrapure water so that the mass of the dye compound relative to the total mass of the ink stock solution is 1/5000. It was set.
  • Example 11 to 26, Comparative Examples 11 to 12 [Preparation of ink for inkjet recording] Based on the composition shown in Table 2 below, each inkjet recording ink was prepared. In the same manner as in Example 1, an ink stock solution containing a dye compound and a preservative was prepared, diluted by adding the remaining components, stirred for 30 minutes at room temperature, and then using a 4 mol / L lithium hydroxide aqueous solution. Then, the pH was adjusted to 8.2, and the obtained solution was filtered using a membrane filter having an aperture of 1.0 ⁇ m to obtain each ink for ink jet recording.
  • each component indicates the mass% of each component when the mass of the ink for inkjet recording is 100%, and the “residue” indicating the amount of water is combined with the components other than water. The amount is 100% in total. Inkjet recording inks B-01 to B-18 were thus prepared.
  • ABS absorbance
  • the ABS (absorbance) of the inkjet recording ink immediately after the ink preparation for inkjet recording was diluted with ultrapure water so that the mass of the coloring compound relative to the total mass of the inkjet recording ink was 1/5000.
  • Value and forced thermal aging test at 60 ° C. for 14 days
  • Stylus Color 880 (trademark) (trade name, manufactured by Seiko Epson Corporation) was used, and an inkjet-dedicated recording medium ⁇ photographic paper ⁇ gloss> (trade name, manufactured by Seiko Epson Corporation) ⁇ was used.
  • Monochrome with ink cartridges filled with ink for ink jet recording loaded into an ink jet printer, and the density changed stepwise so that the OD value measured with a reflection densitometer (X-Rite 310TR) is 0.7 to 1.8.
  • An image pattern was printed, and image fastness (light resistance and ozone gas resistance) and image quality (bronze gloss) were evaluated.
  • D represents the OD value after the exposure test
  • D 0 represents the OD value before the exposure test.
  • the ozone resistance recorded on the ink jet recording medium was ranked A to D using the following criteria.
  • Evaluation A ROD after 7 days from the start of the test is 85% or more at any concentration.
  • Evaluation B The ROD after 7 days from the start of the test is such that the concentration at any one point is less than 85%.
  • Evaluation C The ROD after 7 days from the start of the test is such that the concentration at any two points is less than 85%.
  • Evaluation D ROD after 7 days from the start of the test is less than 85% at all concentrations. In this test, a recorded material with little decrease in ROD is excellent even when exposed to ozone for a long time. The obtained results are shown in Table 3 as “ozone gas fastness”.
  • D represents the OD value after the exposure test
  • D 0 represents the OD value before the exposure test.
  • the light resistance recorded on the inkjet recording medium was ranked A to D using the following criteria.
  • the compound which can form the image which is excellent in light resistance and ozone resistance, can suppress the bronze glossiness, and can prepare the ink which is excellent in storage stability can be provided.
  • the coloring composition containing this compound, the inkjet recording ink, the inkjet recording method using the inkjet recording ink, an inkjet printer cartridge, and an inkjet recorded matter can be provided.

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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 composé qui a d'excellentes résistance à l'ozone et solidité à la lumière, qui permet d'éviter le bronzage lors de la formation d'images et qui permet de préparer une encre présentant une excellente stabilité au stockage, ainsi qu'une composition colorante et une encre pour l'impression par jet d'encre qui contiennent ledit composé, un procédé d'impression par jet d'encre qui utilise ladite encre d'impression par jet d'encre, une cartouche d'imprimante à jet d'encre et un produit imprimé par jet d'encre. Un exemple de ces derniers est un composé représenté par NOIR-1 ou NOIR-2, une composition colorante et une encre pour l'impression par jet d'encre qui contiennent ledit composé, un procédé d'impression par jet d'encre qui utilise ladite encre d'impression par jet d'encre, une cartouche d'imprimante à jet d'encre et un produit imprimé par jet d'encre.
PCT/JP2015/054440 2014-03-19 2015-02-18 Composé, composition colorante, encre pour l'impression par jet d'encre, procédé d'impression par jet d'encre, cartouche d'imprimante à jet d'encre et produit imprimé par jet d'encre Ceased WO2015141362A1 (fr)

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JP2014057181A JP6247971B2 (ja) 2014-03-19 2014-03-19 化合物、着色組成物、インクジェット記録用インク、インクジェット記録方法、インクジェットプリンタカートリッジ、及びインクジェット記録物
JP2014-057181 2014-03-19

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WO2019065636A1 (fr) * 2017-09-29 2019-04-04 富士フイルム株式会社 Ensemble d'encres, cartouche d'encre, imprimante à jet d'encre, et procédé d'enregistrement à jet d'encre

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JP2012177073A (ja) * 2010-07-30 2012-09-13 Fujifilm Corp 新規なアゾ化合物、水溶液、インク組成物、インクジェット記録用インク、インクジェット記録方法、インクジェット記録用インクカートリッジ、及びインクジェット記録物
JP2012193333A (ja) * 2011-02-28 2012-10-11 Fujifilm Corp インク組成物、インクジェット記録用インク及びインクジェット記録方法

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JP2012177073A (ja) * 2010-07-30 2012-09-13 Fujifilm Corp 新規なアゾ化合物、水溶液、インク組成物、インクジェット記録用インク、インクジェット記録方法、インクジェット記録用インクカートリッジ、及びインクジェット記録物
JP2012193333A (ja) * 2011-02-28 2012-10-11 Fujifilm Corp インク組成物、インクジェット記録用インク及びインクジェット記録方法

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