WO2017146070A1 - Composé, composition colorante, encre pour enregistrement à jet d'encre, procédé d'enregistrement à jet d'encre, et cartouche pour imprimante à jet d'encre - Google Patents

Composé, composition colorante, encre pour enregistrement à jet d'encre, procédé d'enregistrement à jet d'encre, et cartouche pour imprimante à jet d'encre Download PDF

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WO2017146070A1
WO2017146070A1 PCT/JP2017/006442 JP2017006442W WO2017146070A1 WO 2017146070 A1 WO2017146070 A1 WO 2017146070A1 JP 2017006442 W JP2017006442 W JP 2017006442W WO 2017146070 A1 WO2017146070 A1 WO 2017146070A1
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group
substituted
unsubstituted
ink
ink jet
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Japanese (ja)
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藤江　賀彦
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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
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B11/00—Diaryl- or thriarylmethane dyes
    • C09B11/04—Diaryl- or thriarylmethane dyes derived from triarylmethanes, i.e. central C-atom is substituted by amino, cyano, alkyl
    • C09B11/10—Amino derivatives of triarylmethanes
    • C09B11/24—Phthaleins containing amino groups ; Phthalanes; Fluoranes; Phthalides; Rhodamine dyes; Phthaleins having heterocyclic aryl rings; Lactone or lactame forms of triarylmethane 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
    • C09B11/00—Diaryl- or thriarylmethane dyes
    • C09B11/04—Diaryl- or thriarylmethane dyes derived from triarylmethanes, i.e. central C-atom is substituted by amino, cyano, alkyl
    • C09B11/10—Amino derivatives of triarylmethanes
    • C09B11/22—Amino derivatives of triarylmethanes containing OH groups bound to an aryl nucleus and their ethers and esters
    • 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 compound, a coloring composition, an ink for ink jet recording, an ink jet recording method, and an ink jet printer cartridge.
  • the ink jet recording method is a method of printing by causing ink droplets to fly and adhere to a recording medium such as paper as is well known.
  • This printing method is capable of printing high-resolution, high-quality images at high speed and easily with an inexpensive apparatus.
  • technical development has recently been carried out as an image forming method that can replace photographs. .
  • Patent Document 1 describes a xanthene derivative substituted with an anilino group, and a compound in which an acylamino group is substituted for the anilino group.
  • the present invention relates to a compound capable of forming an image having excellent light resistance and moisture resistance, a colored composition containing the above compound, an ink for ink jet recording, an ink jet recording method using the ink for ink jet recording, and an ink jet
  • An object is to provide a printer cartridge.
  • the present inventors have found that the above problem can be solved by the compound represented by the general formula (1).
  • an anilino group of a xanthene derivative substituted with an anilino group is substituted with an acylamino group, and a carboxyl group is bonded to the acylamino group via a linking group.
  • a sulfo group is bonded to a specific position (ortho position relative to the anilino group).
  • R 1 , R 2 , R 5 and R 6 each independently represents an unsubstituted alkyl group having 1 to 3 carbon atoms;
  • R 3 , R 4 , R 7 , and R 8 each independently represent a hydrogen atom or a substituent
  • L is a residue obtained by removing m hydrogen atoms from a substituted or unsubstituted alkyl group, a residue obtained by removing m hydrogen atoms from a substituted or unsubstituted alkenyl group, or m residues from a substituted or unsubstituted aryl group.
  • M represents a hydrogen atom or an alkali metal.
  • m represents an integer of 1 to 5.
  • a plurality of M may be the same or different.
  • a plurality of L may be the same or different.
  • a plurality of m may be the same or different.
  • R 3 , R 4 , R 7 and R 8 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a hydroxyl group, a substituted or unsubstituted alkoxy group, substituted or unsubstituted Substituted aryloxy group, substituted or unsubstituted amino group, substituted or unsubstituted acyl group, carboxyl group, sulfo group, substituted or unsubstituted carbamoyl group, substituted or unsubstituted alkoxycarbonyl group, substituted or unsubstituted ⁇ 1>
  • the compound according to ⁇ 1> which represents an aryloxycarbonyl group, a substituted or unsubstituted sulfamoyl group, a mercapto group, a substituted or unsubstituted alkylthio group, or
  • ⁇ 3> The compound according to ⁇ 1> or ⁇ 2>, wherein R 3 and R 7 each independently represent a substituted or unsubstituted alkyl group.
  • R 4 and R 8 represent a hydrogen atom.
  • ⁇ 5> ⁇ 1>- ⁇ 4>
  • ⁇ 6> ⁇ 1> to ⁇ 4>
  • An inkjet recording ink comprising the compound according to any one of ⁇ 4>.
  • ⁇ 7> An inkjet recording method using the inkjet recording ink according to ⁇ 6>.
  • ⁇ 8> An ink jet printer cartridge filled with the ink for ink jet recording according to ⁇ 6>.
  • a compound capable of forming an image having excellent light resistance and moisture resistance a colored composition containing the compound, an ink for ink jet recording, an ink jet recording method using the ink for ink jet recording, And an inkjet printer cartridge.
  • FIG. 1 is a diagram showing a 1 H-NMR (nuclear magnetic resonance) spectrum of Exemplified Compound 1 in dimethyl sulfoxide-d6.
  • FIG. It is a figure which shows the absorption spectrum in the dilute aqueous solution of the exemplary compound 1.
  • 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 for example, 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.
  • the ionic hydrophilic group examples 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 ionic hydrophilic group may be in a state containing a cation or an anion (also referred to as “salt state”).
  • the carboxyl group, the phosphono group, and the sulfo group may be in a state containing a cation.
  • Examples of the cation that forms a salt state include ammonium ion, alkali metal ion (eg, lithium ion, sodium ion, potassium ion). Ions) and organic cations (eg, tetramethylammonium ion, tetramethylguanidinium ion, tetramethylphosphonium), lithium ion, sodium ion, potassium ion, and ammonium ion are preferable, and lithium ion or sodium ion is more preferable. Sodium ion is more preferable.
  • the salt when the compound is a salt, the salt is dissociated into ions in the water-soluble ink.
  • R 1 , R 2 , R 5 and R 6 each independently represents an unsubstituted alkyl group having 1 to 3 carbon atoms;
  • R 3 , R 4 , R 7 , and R 8 each independently represent a hydrogen atom or a substituent
  • L is a residue obtained by removing m hydrogen atoms from a substituted or unsubstituted alkyl group, a residue obtained by removing m hydrogen atoms from a substituted or unsubstituted alkenyl group, or m residues from a substituted or unsubstituted aryl group.
  • M represents a hydrogen atom or an alkali metal.
  • m represents an integer of 1 to 5.
  • a plurality of M may be the same or different.
  • a plurality of L may be the same or different.
  • a plurality of m may be the same or different.
  • the unsubstituted alkyl group having 1 to 3 carbon atoms represented by R 1 , R 2 , R 5 , and R 6 in the general formula (1) is a linear, branched, or cyclic group having 1 to 3 carbon atoms. Examples thereof include an alkyl group. Specifically, a methyl group, an ethyl group, an n-propyl group, and an isopropyl group are preferable, a methyl group or an ethyl group is more preferable, and a methyl group is still more preferable.
  • R 3 , R 4 , R 7 , and R 8 each independently represent a hydrogen atom or a substituent, and examples of the substituent include a substituent selected from the above substituent group A.
  • R 3 , R 4 , R 7 and R 8 are each independently a hydrogen atom, substituted or unsubstituted alkyl group, substituted or unsubstituted aryl group, hydroxyl group, substituted or unsubstituted alkoxy group, substituted or unsubstituted Aryloxy group, substituted or unsubstituted amino group, substituted or unsubstituted acyl group, carboxyl group, sulfo group, substituted or unsubstituted carbamoyl group, substituted or unsubstituted alkoxycarbonyl group, substituted or unsubstituted aryl
  • the alkyl group when R 3 , R 4 , R 7 and R 8 in the general formula (1) represent a substituted or unsubstituted alkyl group is preferably an alkyl group having 1 to 12 carbon atoms.
  • An alkyl group having 6 to 6 carbon atoms is more preferable, and an alkyl group having 1 to 3 carbon atoms is still more preferable.
  • Examples of the alkyl group include a linear, branched or cyclic alkyl group, and specifically include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, and a sec-butyl group.
  • T-butyl group and cyclohexyl group are preferred, methyl group, ethyl group and isopropyl group are more preferred, methyl group or ethyl group is further preferred, and methyl group is most preferred.
  • R 3 and R 7 in the general formula (1) each independently represent a substituted or unsubstituted alkyl group. Further, it is preferred that R 4 and R 8 are hydrogen.
  • L is a substituted or unsubstituted alkyl group (for example, methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, t-butyl group, pentyl group, hexyl group, preferably methyl group, ethyl group, n
  • a residue obtained by removing m hydrogen atoms from a -propyl group or a butyl group a substituted or unsubstituted alkenyl group (eg, vinyl group, allyl group, 3-buten-1-yl group, preferably vinyl group) a residue obtained by removing m hydrogen atoms, a residue obtained by removing m hydrogen atoms from a substituted or unsubstituted aryl group (for example, a phenyl group, a naphthyl group, preferably a phenyl group), or a substituted or unsubstituted one A residue obtained by removing
  • M represents a hydrogen atom or an alkali metal, preferably represents an alkali metal, more preferably represents lithium, sodium, or potassium, and still more preferably represents sodium.
  • m represents an integer of 1 to 5, preferably an integer of 1 to 3, and more preferably 1 or 2.
  • the compound represented by the general formula (1) can be synthesized according to a conventionally known method (for example, Japanese Patent Application Laid-Open No. 2011-148973). More specific synthesis methods are exemplified in the examples.
  • the coloring composition of the present invention contains at least one compound represented by the above general formula (1).
  • the coloring composition of the present invention can contain a medium, but when a solvent is used as the medium, it is particularly suitable as an ink for inkjet recording.
  • the coloring composition of the present invention can be prepared by dissolving and / or dispersing the compound represented by the general formula (1) in a lipophilic medium or an aqueous medium as a medium. it can. Preferably, an aqueous medium is used.
  • the coloring composition of the present invention includes an ink composition excluding a medium.
  • the content of the compound of the present invention contained in the colored composition is determined by the type of substituent in the general formula (1) used, the type of solvent component used for producing the colored composition, and the like.
  • the content of the compound represented by the general formula (1) in the coloring composition is preferably 0.2 to 20% by mass with respect to the total mass of the coloring composition, and is preferably 1 to 10% by mass. More preferably, it is contained in an amount of 2 to 6% by mass.
  • the content of the compound represented by the general formula (1) contained in the coloring composition By setting the content of the compound represented by the general formula (1) contained in the coloring composition to 1% by mass or more, it is possible to improve the print density of the ink on the recording medium when printed, and it is necessary. Image density can be ensured. Moreover, when the total amount of the compounds represented by the general formula (1) contained in the colored composition is 20% by mass or less, the dischargeability of the colored composition can be improved when used in the ink jet recording method. In addition, it is possible to obtain an effect such that the inkjet nozzle is not easily clogged.
  • 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 present invention also relates to an inkjet recording ink containing at least one compound represented by the general formula (1).
  • the ink for inkjet recording can be produced by dissolving and / or dispersing the compound represented by the general formula (1) of the present invention in an oleophilic medium or an aqueous medium.
  • the ink uses an aqueous medium. If necessary, 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.
  • additives examples include those described in JP-A-2013-133394, [0091] to [0101].
  • the contents described in the above-mentioned patent documents can be preferably referred to.
  • the compound represented by the general formula (1) of the present invention is contained in an amount of 0.2% by mass or more and 10% by mass or less in 100% by mass of the ink jet recording ink of the present invention. It is more preferable to contain the following.
  • other dyes may be used in combination with the compound represented by the general formula (1) of the present invention. 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 as an ink jet recording ink having a magenta color tone.
  • 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.
  • Supports for recording paper and recording film include chemical pulps such as LBKP (hardwood bleached kraft pulp), NBKP (softwood bleached kraft pulp), GP (ground pulp), PGW (pressurized groundwood pulp), RMP (refiner ground) ⁇ Pulp), TMP (Thermo-mechanical pulping), CTMP (Chemi-thermo-mechanical pulping), CMP (Chemical mechanical pulp), CGP (Chemical ground pulp), etc.
  • chemical pulps such as LBKP (hardwood bleached kraft pulp), NBKP (softwood bleached kraft pulp), GP (ground pulp), PGW (pressurized groundwood pulp), RMP (refiner ground) ⁇ Pulp), TMP (Thermo-mechanical pulping), CTMP (Chemi-thermo-mechanical pulping), CMP (Chemical mechanical pulp), CGP (Chemical ground pulp), etc.
  • 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.
  • any material may be used as the material to be dyed.
  • a sheet-like material such as a fabric (hydrophobic fiber fabric, etc.), a resin (plastic) film, paper, or the like is preferably used.
  • An object having a three-dimensional shape such as a rectangular parallelepiped shape may be used.
  • the crystals of Exemplified Compound 1 were obtained by adjusting to 8.5, removing dust using a membrane filter (Advantech, pore size 0.2 ⁇ m), and concentrating to dryness. Yield 3.7 g, 74% yield.
  • the 1 H-NMR spectrum of Exemplified Compound 1 in dimethyl sulfoxide-d6 is shown in FIG.
  • the absorption spectrum in the dilute aqueous solution of exemplary compound 1 is shown in FIG.
  • the absorption maximum wavelength in the absorption spectrum of Exemplified Compound 1 in a dilute aqueous solution was 533 nm.
  • Example 1 Deionized water was added to the following ingredients to make 100 g, followed by stirring for 1 hour while heating at 30 to 40 ° C. Thereafter, the pH was adjusted to 9 with a 10 mol / L sodium hydroxide aqueous solution, and the solution was filtered under reduced pressure through a microfilter having an average pore size of 0.25 ⁇ m to prepare magenta ink liquid 1.
  • Dye (Exemplary Compound 1) 3.50 g Diethylene glycol 10.65g Glycerin 14.70g Diethylene glycol monobutyl ether 12.70g Triethanolamine 0.65g Olfin E1010 (Nissin Chemical Industry Co., Ltd.) 0.9g
  • Examples 2 to 12, Comparative Examples 1 to 3 Except for changing the dye as shown in Table 1 below, in the same manner as in the preparation of Ink Liquid 1, ink liquids 2 to 12 and comparative compounds 1 to 3 shown below as comparative ink liquids were used for comparison. Ink liquids 1 to 3 were prepared. The prepared ink liquids 1 to 12 and comparative ink liquids 1 to 3 were used as inks for inkjet recording.
  • a print pattern of 3 cm ⁇ 3 cm is prepared by arranging a blue 1 mm ⁇ 1 mm square formed by magenta ink and cyan ink so that a white background gap of 0.5 mm is formed between the squares. After storage for 168 hours at 45 ° C. and a relative humidity of 85%, the magenta dye bleed in the white space was observed.
  • magenta inks inks prepared as examples and comparative examples were used, and as cyan ink, ICC70 (trade name, manufactured by Seiko Epson Corporation) was used.
  • the OD value of the printed matter before and after exposure to the above high humidity conditions is measured using a reflection densitometer (X-rite i1, trade name, manufactured by X-Rite), and the magenta density of the white background increases immediately after printing.
  • X-rite i1 trade name, manufactured by X-Rite
  • S is less than 0.02
  • A is 0.02 or more and less than 0.05
  • B is 0.05 or more and less than 0.1
  • C is 0.1 or more. Evaluation was made in 4 stages.
  • a compound capable of forming an image having excellent light resistance and moisture resistance a colored composition containing the compound, an ink for ink jet recording, an ink jet recording method using the ink for ink jet recording, And an inkjet printer cartridge.

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

Abstract

L'invention fournit un composé représenté par la formule générale (1) définie dans la description, une composition colorante comprenant ce composé, une encre pour enregistrement à jet d'encre, un procédé d'enregistrement à jet d'encre mettant en œuvre cette encre pour enregistrement à jet d'encre, et une cartouche pour imprimante à jet d'encre.
PCT/JP2017/006442 2016-02-25 2017-02-21 Composé, composition colorante, encre pour enregistrement à jet d'encre, procédé d'enregistrement à jet d'encre, et cartouche pour imprimante à jet d'encre Ceased WO2017146070A1 (fr)

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JP2018501718A JPWO2017146070A1 (ja) 2016-02-25 2017-02-21 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、及びインクジェットプリンタカートリッジ

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JP2016034747 2016-02-25
JP2016-034747 2016-02-25

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Cited By (2)

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Publication number Priority date Publication date Assignee Title
WO2018061784A1 (fr) * 2016-09-30 2018-04-05 富士フイルム株式会社 Solution aqueuse, composition colorante, encre pour enregistrement à jet d'encre, procédé d'enregistrement à jet d'encre, et cartouche d'encre
WO2018163940A1 (fr) * 2017-03-06 2018-09-13 富士フイルム株式会社 Composition colorante, encre pour impression à jet d'encre, procédé d'impression à jet d'encre et cartouche pour imprimante à jet d'encre

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JP2014205821A (ja) * 2013-03-21 2014-10-30 キヤノン株式会社 化合物、インク、インクカートリッジ、及びインクジェット記録方法
WO2015105108A1 (fr) * 2014-01-10 2015-07-16 富士フイルム株式会社 Composé, composition colorante, encre d'impression par jet d'encre, procédé d'impression par jet d'encre, cartouche d'imprimante à jet d'encre, matériau imprimé par jet d'encre, filtre de couleur, encre en poudre de couleur et encre de transfert
WO2015199135A1 (fr) * 2014-06-24 2015-12-30 富士フイルム株式会社 Composition colorante pour teinture ou impression textile, encre pour impression textile à jet d'encre, procédé d'impression textile de tissu, et tissu teint ou à impression textile

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Publication number Priority date Publication date Assignee Title
JP2014205821A (ja) * 2013-03-21 2014-10-30 キヤノン株式会社 化合物、インク、インクカートリッジ、及びインクジェット記録方法
WO2015105108A1 (fr) * 2014-01-10 2015-07-16 富士フイルム株式会社 Composé, composition colorante, encre d'impression par jet d'encre, procédé d'impression par jet d'encre, cartouche d'imprimante à jet d'encre, matériau imprimé par jet d'encre, filtre de couleur, encre en poudre de couleur et encre de transfert
WO2015199135A1 (fr) * 2014-06-24 2015-12-30 富士フイルム株式会社 Composition colorante pour teinture ou impression textile, encre pour impression textile à jet d'encre, procédé d'impression textile de tissu, et tissu teint ou à impression textile

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2018061784A1 (fr) * 2016-09-30 2018-04-05 富士フイルム株式会社 Solution aqueuse, composition colorante, encre pour enregistrement à jet d'encre, procédé d'enregistrement à jet d'encre, et cartouche d'encre
US10745577B2 (en) 2016-09-30 2020-08-18 Fujifilm Corporation Aqueous solution, coloring composition, ink jet recording ink, ink jet recording method, and ink cartridge
WO2018163940A1 (fr) * 2017-03-06 2018-09-13 富士フイルム株式会社 Composition colorante, encre pour impression à jet d'encre, procédé d'impression à jet d'encre et cartouche pour imprimante à jet d'encre

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