JPH09324146A - Ink jet recording liquid - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain the subject recording liquid containing a coloring matter expressed by a specific formula, excellent in the light resistance of printed color images, having an excellent effect on a color tone for the good reproducibility of the color and effective for magenta color. SOLUTION: This ink jet recording liquid contains a coloring matter of the formula [R1 , R2 are each H, an alkyl, an alkenyl, etc.; R3 is amino, an acylamino, sulfonylamino, etc.; R4 is H, an alkyl, an alkoxy, an acylamino, etc.; R5 is a halogen, an alkyl, an alkoxy, amino, sulfo, etc.; (n) is 0-5; one of X1 , X2 is CR6 (R6 is H, an alkyl, an acylamino, etc.), and the other is N atom]. For example, an aqueous ink jet recording liquid preferably contains water and a water-soluble organic solvent such as methanol as solvents in addition to the coloring matter of the formula.

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention relates to an inkjet recording liquid containing a specific dye.

[0002]

2. Description of the Related Art Ink jet inks include:
It is suitable for the recording method used, has a high recorded image density and good color tone, has excellent color image fastness such as light resistance, heat resistance and water resistance, and can be fixed to a recording medium. It is required that it does not bleed quickly after recording, that it has excellent storage stability as an ink, that it has no safety issues such as toxicity and flammability, and that it is inexpensive. Although the above recording liquids have been proposed and studied, the ink jet recording liquids that can satisfy many of the requirements at the same time are extremely limited.

In color image recording using yellow, magenta, cyan, and black, for example, C.I. I. A conventionally known C.I. described in the index. I. Dyes and pigments having a number have been widely studied. Particularly in magenta ink, xanthene-based ink (for example, C.I.
I. Acid Red 52, etc.), azo series (for example, C.I.
It is known that a water-soluble dye such as Reactive Red 180) is used, but in general, the former has a problem of fastness such as light resistance, and the latter has a color reproducibility such as lack of sharpness of magenta color tone. Had a problem of spectral absorption characteristics.

[0004]

In order to solve this problem, an inkjet recording liquid using a magenta dye excellent in color tone and light resistance is being actively developed, but a satisfactory inkjet recording liquid is still available. The current situation is that it has not been achieved. An object of the present invention is to provide an inkjet recording liquid having excellent light resistance of a color image and an excellent color tone for obtaining good color reproducibility, particularly a magenta inkjet recording liquid.

[0005]

The above object of the present invention is achieved by the following constitution.

1. An ink jet recording liquid containing a dye represented by the following general formula (1).

[0007]

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In the formula, R ₁ and R ₂ each represent a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, an aralkyl group, an aromatic residue or a heterocyclic residue, and R ₁ forms a ring with R _2. May be. R ₃ is an amino group, an acylamino group,
It represents a sulfonylamino group, an alkoxy group, an alkyl group, an alkoxycarbonyl group, a carbamoyl group, a carboxyl group or a cyano group. R ₄ is a hydrogen atom, an alkyl group,
Alkoxy group, acylamino group, sulfonylamino group,
It represents an alkoxycarbonylamino group, a ureido group or a halogen atom. m represents an integer of 0 to 2. R ₅ represents a halogen atom, an alkyl group, an alkoxy group, an amino group, a sulfo group, a carboxyl group, a sulfamoyl group, a carbamoyl group, an alkoxycarbonyl group, a hydroxy group, an acylamino group, a sulfonylamino group, a ureido group or an alkoxycarbonylamino group. . n represents an integer of 0 to 5, and when n is 2 or more, R ₅ may be different from each other. One of X ₁ and X ₂ represents CR ₆ (R ₆ represents a hydrogen atom, an alkyl group, an acylamino group, a sulfonylamino group, a ureido group, an alkoxycarbonylamino group, a halogen atom or an alkoxy group), and the other is nitrogen. Represents an atom.

[0009] 2. 2. The inkjet recording liquid according to 1 above, wherein the dye represented by the general formula (1) is a dye represented by the following general formula (2).

[0010]

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[0011] In the formula, R ₇ and R ₈ are each an alkyl group, an aralkyl group, R ₇ may form a ring with R _8. R ₉ represents an amino group or an acylamino group. R ₁₀
Represents a hydrogen atom, an alkyl group or an acylamino group.
o represents an integer of 0 to 2. R ₁₁ represents a halogen atom or a sulfo group. p represents an integer of 0 to 5, and when p is 2 or more, R ₁₁ may be different from each other. One of X ₃ and X ₄ represents CR ₁₂ (R ₁₂ represents a hydrogen atom, an alkyl group or an acylamino group), and the other represents a nitrogen atom.

The present invention will be described in detail below.

First, the compound represented by the general formula (1) of the present invention will be described in detail.

R ₁ and R ₂ are each a hydrogen atom, an alkyl group (eg, methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, pentyl group, neopentyl group or hexyl group), alkenyl group (eg, Allyl group), alkynyl group (eg, probargyl group, etc.),
Aralkyl groups (eg benzyl group or phenethyl group etc.), aromatic residues (eg phenyl group or naphthyl group etc.) or heterocyclic residues (eg pyridyl group, pyrazinyl group, pyrimidinyl group, thienyl group, furyl group, thiazolyl group, Oxazolyl group, isoxazolyl group, pyrrolyl group, pyrazolyl group, imidazolyl group, tetrahydrofuryl group, piperazinyl group, piperidinyl group, morpholinyl group, benzothiazolyl group, benzoxazolyl group or benzimidazolyl group).

R ₁ and R ₂ may form a ring (for example, a piperidine ring, a pyrrolidine ring, a piperazine ring or a morpholine ring) together with a nitrogen atom.

R ₁ and R ₂ may be further substituted with a suitable substituent, and examples of the suitable substituent include an aliphatic group (eg, an alkyl group having 1 to 20 carbon atoms) and an aromatic residue ( For example, a phenyl group, a naphthyl group, etc.), a heterocyclic residue (for example, a 5- or 6-membered heterocyclic residue having at least one atom selected from nitrogen atom, oxygen atom, and sulfur atom), alkoxy group ( For example, an alkoxy group having 1 to 20 carbon atoms, an aryloxy group (eg, phenoxy group, naphthyloxy group, etc.), an acylamino group (eg, alkanoylamino group having 1 to 20 carbon atoms, benzoylamino group, etc.), acyloxy A group (for example, 1 to 1 carbon atoms)
20 alkanoyloxy group, benzoyloxy group, etc.), acyl group (for example, alkanoyl group having 1 to 20 carbon atoms, benzoyl group, etc.), carbamoyl group (for example, unsubstituted carbamoyl group, alkylcarbamoyl group having 1 to 20 carbon atoms) , A dialkylcarbamoyl group having 2 to 40 carbon atoms, a phenylcarbamoyl group, an N-alkyl-N-phenylcarbamoyl group having 7 to 26 carbon atoms), an alkoxycarbonyl group (for example, an alkoxycarbonyl group having 1 to 20 carbon atoms), Sulfonylamino group (eg, having 1 carbon atom
To alkanesulfonylamino group, benzenesulfonylamino group, etc.), sulfamoyl group (eg, unsubstituted sulfamoyl group, alkylsulfamoyl group having 1 to 20 carbon atoms, dialkylsulfamoyl group having 2 to 40 carbon atoms, phenyl) Sulfamoyl group, N-C7-26
Alkyl-N-phenylsulfamoyl group, etc., hydroxyl group, sulfonyl group (eg, alkanesulfonyl group having 1 to 20 carbon atoms, benzenesulfonyl group, etc.), alkylthio group (eg, alkylthio group having 1 to 20 carbon atoms, etc.) ), An arylthio group (for example, a phenylthio group, etc.),
Ureido group (eg, unsubstituted ureido group, carbon number 1 to 2)
0 alkyl ureido group, C 2-40 dialkyl ureido group, phenyl ureido group, etc.), urethane group (for example, C 1-20 alkoxycarbonylamino group, etc.), cyano group, sulfo group, carboxyl group, nitro group Group or amino group (for example, an unsubstituted amino group, a carbon number of 1 to
20 alkylamino groups, C2-40 dialkylamino groups, anilino groups, C7-26 N-alkylanilino groups, and the like).

As R ₁ and R ₂ , an alkyl group or an aralkyl group is preferable.

R ₃ is an amino group (for example, having 1 to 20 carbon atoms).
Alkylamino group, dialkylamino group having 2 to 40 carbon atoms, piperidino group, piperazino group, morpholino group, pyrrolidino group, anilino group, N-alkylanilino group having 7 to 26 carbon atoms, naphthylamino group, unsubstituted amino Groups, etc.), acylamino groups (eg, alkanoylamino groups having 1 to 20 carbon atoms, benzoylamino groups, etc.), sulfonylamino groups (eg, alkanesulfonylamino groups having 1 to 20 carbon atoms, benzenesulfonylamino groups, etc.), alkoxy A group (for example, an alkoxy group having 1 to 20 carbon atoms),
Alkyl group (for example, linear, branched or cyclic alkyl group having 1 to 20 carbon atoms), alkoxycarbonyl group (for example,
It represents an alkoxycarbonyl group having 1 to 20 carbon atoms), a carbamoyl group (for example, an alkylcarbamoyl group having 1 to 20 carbon atoms, an arylcarbamoyl group), a carboxyl group or a cyano group.

R ₃ is preferably an amino group or an acylamino group. R ₃ may be further substituted with a suitable substituent, and examples of the suitable substituent include the groups described above as the suitable substituents of R ₁ and R ₂ which may be substituted.

R ₄ is a hydrogen atom, an alkyl group (for example, a straight chain, branched or cyclic alkyl group having 1 to 25 carbon atoms) or an alkoxy group (for example, a straight chain, branched or cyclic group having 1 to 25 carbon atoms). Alkoxy group, etc.), acylamino group (eg, alkanoylamino group having 1 to 25 carbon atoms, benzoylamino group, etc.), sulfonylamino group (eg, 1 to 25 carbon atoms)
Alkanesulfonylamino group, benzenesulfonylamino group, etc.), alkoxycarbonylamino group (for example,
An alkoxycarbonylamino group having 1 to 25 carbon atoms),
It represents a ureido group (for example, an alkylureido group having 1 to 20 carbon atoms, a phenylureido group or the like) or a halogen atom (for example, a fluorine atom, a chlorine atom or a bromine atom).

R ₄ is preferably a hydrogen atom, an alkyl group or an acylamino group. m represents an integer of 0 to 2.

R ₅ is a halogen atom (for example, a fluorine atom, a chlorine atom or a bromine atom), an alkyl group (for example, a linear, branched or cyclic alkyl group having 1 to 25 carbon atoms) or an alkoxy group (for example, Straight chain having 1 to 25 carbon atoms,
A branched or cyclic alkoxy group), an amino group (for example, an alkylamino group having 1 to 25 carbon atoms, a dialkylamino group having 2 to 50 carbon atoms, anilino group, N- having 7 to 31 carbon atoms).
Alkylanilino group, etc.), sulfo group, carboxyl group,
Sulfamoyl group (eg, alkylsulfamoyl group having 1 to 20 carbon atoms, phenylsulfamoyl group, etc.), carbamoyl group (eg, alkylcarbamoyl group having 1 to 20 carbon atoms, arylcarbamoyl group, etc.), alkoxycarbonyl group ( For example, an alkylcarbonyl group having 1 to 20 carbon atoms, a hydroxy group, an acylamino group (for example, an alkanoylamino group having 1 to 20 carbon atoms, a benzoylamino group, etc.), a sulfonylamino group (for example, having 1 to 20 carbon atoms). Alkanesulfonylamino group, benzenesulfonylamino group, etc., ureido group (for example, having 1 to 1 carbon atoms)
20 alkylureido groups, phenylureido groups, etc.) or alkoxycarbonylamino groups (eg, having 1 carbon atom)
.About.20 alkoxycarbonylamino groups). n
Represents an integer of 0 to 5, and when n is 2 or more, R ₅ may be different from each other.

R ₅ is preferably a halogen atom or a sulfo group.

_One of X ₁ and X ₂ is CR ₆ (R ₆ is a hydrogen atom,
Alkyl group (eg methyl group or ethyl group), acylamino group (eg acetylamino group, trifluoroacetylamino group or propanoylamino group etc.), sulfonylamino group (eg methanesulfonylamino group or trifluoromethanesulfonylamino group etc.) A ureido group (eg, methylureido group or ethylureido group), an alkoxycarbonylamino group (eg, ethoxycarbonylamino group), a halogen atom (eg, fluorine atom, chlorine atom or bromine atom), or an alkoxy group (eg, methoxy group or Ethoxy group)) and the other represents a nitrogen atom.

X ₁ is preferably CR ₆ and X ₂ is preferably a nitrogen atom,
Further, preferred R _{6 in} this case includes a hydrogen atom, an alkyl group or an acylamino group, and among these, an alkyl group is most preferred.

In the present invention, among the dyes represented by the general formula (1), the dye represented by the general formula (2) is particularly preferable from the viewpoint of color tone.

In the general formula (2), R ₇ and R ₈ are each an alkyl group (for example, the groups described as specific examples of the aliphatic group of R ₁ and R ₂ in the general formula (1)) or an aralkyl group. (For example, the groups described as specific examples of the aralkyl group of R ₁ and R ₂ in the general formula (1)). R ₇ and R ₈ may together form a ring.

R ₇ and R ₈ may be further substituted with a suitable substituent, and examples of the suitable substituent include R ₁ and R _2.
The groups described as examples of suitable substituents which may be substituted with are mentioned.

R ₉ is an amino group (for example, the groups described as specific examples of the amino group of R _{3 in} the general formula (1))
Or an acylamino group (for example, R of the general formula (1)
Group described as a specific example of the acylamino group of ₃ ).

R ₁₀ is a hydrogen atom, an alkyl group (for example, the groups described as specific examples of the alkyl group for R _{4 in} the above general formula (1)) or an acylamino group (for example, R _{4 in the} above general formula (1)). Group described as a specific example of the acylamino group of). Of these, a hydrogen atom is preferred. o represents an integer of 0 to 2. R ₁₁ represents a halogen atom (for example, the group described as a specific example of the halogen atom of R _{5 in} the above general formula (1)) or a sulfo group. p represents an integer of 0 to 5, and when p is 2 or more, R ₁₁ may be different from each other.

One of X ₃ and X ₄ is CR ₁₂ (R ₁₂ is a hydrogen atom, an alkyl group (for example, the groups described as specific examples of the alkyl group of R _{6 in} the general formula (1)) or an acylamino group ( (For example, the groups described as specific examples of the acylamino group of R _{6 in} the general formula (1))), and the other represents a nitrogen atom. X ₃ is preferably a CR ₁₁ group, and X ₄ is preferably a nitrogen atom. Preferred R _{11 in} this case is a hydrogen atom, an alkyl group or an acylamino group, and among these, an alkyl group is most preferred.

Specific examples of the dye of the present invention are shown below, but the present invention is not limited thereto.

[0033]

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[0034]

[Chemical 6]

[0035]

[Chemical 7]

[0036]

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[0037]

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[0038]

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[0039]

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[0040]

[Chemical 12]

[0041]

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[0042]

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[0043]

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[0044]

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[0045]

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[0046]

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[0047]

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[0048]

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[0049]

[Chemical 21]

[0050]

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[0051]

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[0052]

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[0053]

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[0054]

[Chemical formula 26]

[0055]

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The ink jet recording liquid containing the dye represented by the general formula (1) or (2) of the present invention can be used as an aqueous ink jet recording liquid, an oil ink jet recording liquid, a solid (phase change) ink jet recording liquid and the like. However, it can be used particularly preferably for an aqueous inkjet recording liquid (for example, an aqueous inkjet recording liquid containing 10% by weight or more of water based on the total weight of the ink).

In the water-based ink jet recording liquid, it is preferable to use water in combination with a water-soluble organic solvent as a solvent in addition to the dye represented by the general formula (1) or (2).

Examples of the water-soluble organic solvent include alcohols (eg, methanol, ethanol, propanol,
Isopropanol, butanol, isobutanol, secondary butanol, tertiary butanol, pentanol, hexanol, cyclohexanol, benzyl alcohol, etc., and polyhydric alcohols (for example, ethylene glycol, diethylene glycol, triethylene glycol, polyethylene glycol, propylene glycol, dipropylene) Propylene glycol, polypropylene glycol, butylene glycol, hexanediol, pentanediol, glycerin, hexanetriol, thiodiglycol, etc.), polyhydric alcohol ethers (for example, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monobutyl ether, Diethylene glycol monomethyl ether, diethylene glycol Monoethyl ether, diethylene glycol monobutyl ether, propylene glycol monomethyl ether, propylene glycol monobutyl ether, ethylene glycol monomethyl ether acetate, triethylene glycol monomethyl ether, triethylene glycol monoethyl ether, triethylene glycol monobutyl ether, ethylene glycol monophenyl ether, Propylene glycol monophenyl ether, etc., amines (for example, ethanolamine, diethanolamine, triethanolamine, N-methyldiethanolamine, N-ethyldiethanolamine, morpholine, N-ethylmorpholine, ethylenediamine, diethylenediamine, triethylenetetramine, tetraethylene) Pentamine, Liethyleneimine, pentamethyldiethylenetriamine, tetramethylpropylenediamine, etc.), amides (eg, formamide, N, N-dimethylformamide, N, N-dimethylacetamide, etc.), heterocycles (eg, 2-pyrrolidone, N-methyl) -2-pyrrolidone, cyclohexylpyrrolidone, 2-oxazolidone, 1,3-dimethyl-2
-Imidazolidinone), sulfoxides (eg, dimethylsulfoxide), sulfones (eg, sulfolane), urea, acetonitrile, acetone and the like.

In the above water-based ink jet recording liquid, the dye can be used as it is if it is soluble in the solvent system. On the other hand, when it is a solid that is insoluble as it is, various dyes can be dispersed by various dispersing machines (for example, ball mill, sand mill, attritor, roll mill, agitator mill, Henschel mixer, colloid mill, ultrasonic homogenizer, pearl mill, jet mill, ong mill, etc.). Can be used to make fine particles, or the dye can be dissolved in a soluble organic solvent, and then dispersed in the solvent system together with a polymer dispersant and a surfactant. Furthermore, in the case of a liquid or semi-molten substance which is insoluble as it is, it can be dissolved as it is or in a soluble organic solvent, and can be dispersed in the solvent system together with a polymer dispersant and a surfactant.

A specific method for preparing such an aqueous ink jet recording liquid is described in, for example, JP-A-5-148436.
Nos. 5-295312, 7-97541, 7
Reference can be made to the methods described in, for example, -82515 and 7-118584.

The oil-based ink jet recording liquid uses an organic solvent as a solvent in addition to the dye of the present invention.

Examples of the solvent for the oil-based ink jet recording liquid include alcohols (for example, pentanol, heptanol, octanol, phenylethyl alcohol, phenyl propylene) in addition to those exemplified as the water-soluble organic solvent in the above water-based ink jet recording liquid. Alcohol, furfuryl alcohol, anil alcohol, etc., esters (ethylene glycol diacetate, ethylene glycol monomethyl ether acetate, diethylene glycol monomethyl ether acetate, propylene glycol diacetate, ethyl acetate, amyl acetate, benzyl acetate, phenylethyl acetate, acetic acid Phenoxyethyl, ethyl phenylacetate, benzyl propionate, ethyl benzoate, butyl benzoate, butyl laurate, isopropyl myristate , Triethyl phosphate, tributyl phosphate, diethyl phthalate, dibutyl phthalate, diethyl malonate, dipropyl malonate, diethyl diethyl malonate, diethyl succinate, dibutyl succinate, diethyl glutarate, diethyl adipate, dipropyl adipate, Dibutyl adipate, di (2-methoxyethyl) adipate, diethyl sebacate, diethyl maleate, dibutyl maleate, dioctyl maleate, diethyl fumarate, dioctyl fumarate, 3-hexenyl cinnamate), ethers (Eg, butyl phenyl ether, benzyl ethyl ether, hexyl ether, etc.), ketones (eg, benzyl methyl ketone, benzyl acetone, diacetone alcohol, cyclohexanone, etc.), and hydrocarbons (eg, petroleum ether , Petroleum benzyl, tetralin, decalin, tertiary amyl benzene, dimethyl naphthalene, etc.), amides (e.g.,
N, N-diethyldodecaneamide).

In the oil-based ink jet recording liquid as described above, the dye can be dissolved and used as it is,
In addition, a resinous dispersant or a binder may be used in combination for dispersion or dissolution.

For specific methods for preparing such an oil-based ink jet recording liquid, the methods described in JP-A-3-231975, JP-A-5-508883 and the like can be referred to.

The solid (phase change) ink jet recording liquid is
A phase change solvent which is solid at room temperature and which is in a molten liquid state when the ink is heated and ejected is used.

Examples of such a phase change solvent include natural waxes (eg, beeswax, carnauba wax, rice wax, wood wax, jojoba oil, whale wax, candelilla wax, lanolin, montan wax, ozokerite, ceresin, paraffin). Wax, microcrystalline wax, petrolactam, etc.), polyethylene wax derivative, chlorinated hydrocarbon, organic acid (eg palmitic acid,
Stearic acid, behenic acid, tiglic acid, 2-acetonaphthone behenic acid, 12-hydroxystearic acid, dihydroxystearic acid and the like, and organic acid esters (for example, alcohols such as glycerin, diethylene glycol and ethylene glycol of the above organic acids) Esters, etc.), alcohols (eg, dodecanol, tetradecanol,
Hexadecanol, eicosanol, docosanol, tetracosanol, hexacosanol, octacosanol, dodecenol, myricyl alcohol, tetracenol, hexadecenol, eicosenol, docosenol, pinene glycol, hinokiol, butynediol, nonanediol, isophthalyl alcohol, mesicerine, Terephthalyl alcohol, hexanediol,
Decanediol, dodecanediol, tetradecanediol, hexadecanediol, docosandiol, tetracosanediol, tvneol, phenylglycerin, eicosandiol, octanediol, phenylpropylene glycol, bisphenol A, para-alpha cumyl phenol, etc.), ketone (For example, benzoylacetone, diacetbenzene, benzophenone, tricosanone, heptacosanone, heptatriacontanone, hentriacontanone, heptatriacontanone, stearone, lauron, dianisole, etc.), amide (for example,
Oleic acid amide, lauric acid amide, stearic acid amide, ricinoleic acid amide, palmitic acid amide, tetrahydrofuranic acid amide, erucic acid amide, myristic acid amide, 12-hydroxystearic acid amide, N-
Stearyl erucamide, N-oleyl stearamide, N, N'-ethylenebislauric amide,
N, N'-ethylenebisstearic acid amide, N, N '
-Ethylenebisoleic acid amide, N, N'-methylenebisstearic acid amide, N, N'-ethylenebisbehenic acid amide, N, N'-xylylenebisstearic acid amide, N, N'-butylenebisstearic acid Amide,
N, N'-dioleyl adipamide, N, N'-distearyl adipamide, N, N'-dioleyl sebacamide, N, N'-cystearyl sebacamide, N, N'-diamide Stearyl terephthalamide,
N, N'-distearylisophthalamide, phenacetin, toluamide, acetamide, oleic acid dimer /
Reaction products of dimer acids such as ethylenediamine / stearic acid (1: 2: 2 molar ratio) with diamines and fatty acids, such as tetraamides; sulfonamides (eg, paratoluenesulfonamide, ethylbenzenesulfonamide;
Butylbenzenesulfonamide, etc.), silicones (for example, silicone SH6018 (Toray Silicone), silicone KR215, 216,220 (Shin-Etsu Silicone), etc.), and coumarones (for example, Escron G-90)
(Nippon Steel Chemical Co., Ltd.), cholesterol fatty acid esters (eg, cholesterol stearate, cholesterol palmitate, cholesterol myristate, cholesterol behenate, cholesterol laurate, cholesterol melissate), saccharide fatty acid esters (saccharose stearate, palmitin) Acid saccharose, saccharose behenate, saccharose laurate, saccharose melinate, lactose stearate, lactose palmitate, lactose myristate, lactose behenate, lactose laurate, lactose melinate, and the like.

The phase change temperature in the solid-liquid phase change of the solid inkjet recording liquid is preferably 60 ° C. or higher, more preferably 80 to 150 ° C.

In the solid ink jet recording liquid as described above, the dye of the present invention can be used as it is by dissolving it in a heated solvent in a molten state, and can also be dispersed or dissolved by using a resinous dispersant or a binder in combination. Can also be used.

For the specific method of preparing such a solid ink jet recording liquid, the methods described in JP-A-5-186723 and JP-A-7-70490 can be referred to.

Each of the water-based, oil-based and solid ink jet recording liquids as described above has a flying viscosity of 40 cp.
s or less, and more preferably 30 cps or less.

The surface tension of the ink jet recording liquid of the present invention during flight is preferably 20 dyn / cm or more, more preferably 25 to 80 dyn / cm.

In the ink jet recording liquid of the present invention,
The dye represented by formula (1) or (2) is preferably used in the range of 0.1 to 25% by weight, and preferably 0.5 to 10% by weight, based on the total weight of the entire inkjet recording liquid.
More preferably, it is within the range.

In the ink jet recording liquid of the present invention, a viscosity adjusting agent and a surface tension adjusting agent are used according to the purpose of improving ejection stability, compatibility with print heads and ink cartridges, storage stability, image storability, and other various performances. It is also possible to add an agent, a specific resistance adjusting agent, a film forming agent, a dispersant, a surfactant, an ultraviolet absorber, an antioxidant, a discoloration preventing agent, an antibacterial agent, an anticorrosive agent and the like.

The ink jet recording liquid of the present invention is not particularly limited with respect to the recording system used, and can be preferably used as an ink jet recording liquid for continuous type and on-demand type ink jet printers. Examples of the on-demand type system include an electro-mechanical conversion system (for example, a single cavity type, a double cavity type, a bender type, a piston type, a shared mode type, a shared wall type, etc.), and an electro-thermal conversion system (for example, thermal type). Specific examples include an ink jet type, a bubble jet type, and the like, an electrostatic suction type (for example, an electric field control type, a slit jet type, and the like), and a discharge type (for example, a spark jet type).

[0075]

EXAMPLES The present invention will be described in more detail by way of examples, but the present invention is not limited to the forms in these examples.

Example 1 Each ink composition having the composition shown in Table 1 was used to record on an inkjet-dedicated coated paper with an inkjet printer MJ-5000C (manufactured by Seiko Epson Corporation, electro-mechanical conversion system). A magenta image sample was obtained. Table 1 shows the results of evaluation of light resistance and color tone defined as follows using this sample.

Light resistance: PDA-65 (manufactured by Konica Corporation)
The residual rate of the image for the unexposed sample after 24 hours of exposure was calculated by the xenon fade meter calculated from the measurement of the reflection density by the green light, and evaluated according to the following criteria.

That is, ◯ represents a magenta image having good light resistance.

Light resistance (%) = (green light reflection density of exposed sample / green light reflection density of unexposed sample) × 100 ◯: When light resistance (%) after exposure for 24 hours is 90% or more Δ: Light resistance (%) after exposure for 24 hours is 80% or more and 90%
X: when light resistance (%) after 24 hours of bombardment is less than 80%.

Color tone: PDA-65 (manufactured by Konica Corporation) was used to measure reflection densities in blue, green and red light,
The relative blue light reflection density and the relative red light reflection density when the reflection density in green light was normalized to 1 were calculated and evaluated according to the following criteria. That is, ○ represents a magenta image having a good color tone with little illegal absorption in the wavelength region of blue light and red light.

◯: When relative blue light reflection density is less than 0.25 and relative red light reflection density is less than 0.10 Δ: When relative blue light reflection density is 0.25 or more and relative red light reflection density is less than 0.10. Or, when the relative blue light reflection density is less than 0.25 and the relative red light reflection density is 0.10 or more. X: When the relative blue light reflection density is 0.25 or more and the relative red light reflection density is 0.10 or more The unit of the amount of each compound is% by weight based on the total weight of all the inkjet recording liquids. Comparison described in the table −
The structures of 1, Comparative-2 and Surfactant-1 are shown below.

[0082]

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[0083]

[Table 1]

As is clear from the results shown in Table 1, the ink jet recording liquid of the present invention is superior in light resistance to the case where the comparative ink jet recording liquid is used, and the blue light and the red light with respect to the reflection density in the green light region. It can be seen that there is little false absorption in the light region and the color tone is good.

Further, it can be used without any problem in the continuous discharge test of the printer, and the high reliability of the electro-mechanical conversion system of the ink jet recording liquid of the present invention was confirmed.

Example 2 Using each ink composition having the composition shown in Table 2, an ink jet printer BJC-600J (manufactured by Canon Inc., electric-heat conversion system) was used to record a sample recorded on glossy paper exclusively for ink jet. Obtained. Table 2 shows the results of evaluating the light resistance and color tone of this sample in the same manner as in Example 1. The unit of the amount of each compound in Table 2 is% by weight with respect to the weight of the entire inkjet recording liquid, and the definition of the compounds of Comparative-1 and Comparative-2 and the evaluation items are the same as in Example 1.

[0087]

[Table 2]

As is clear from the results shown in Table 2, the ink jet recording liquid of the present invention is superior in light resistance to the case where the comparative ink jet recording liquid is used, and the blue light and the red light with respect to the reflection density in the green light region. It can be seen that there is little false absorption in the light region and the color tone is good.

Further, in the system of this printer, no abnormality of the head due to thermal deterioration of the ink jet recording liquid was confirmed, and it was confirmed that the system has compatibility with the electric-heat conversion system.

[0090]

The ink jet recording liquid according to the present invention has excellent light fastness of color images, excellent color tone for good color reproducibility, and particularly excellent effect of the present invention for magenta color. .

 ─────────────────────────────────────────────────── ─── Continuation of the front page (72) Inventor Hidetaka Ninomiya 1st Sakura-cho, Hino City, Tokyo Konica Stock Company (72) Inventor Hitoshi Morimoto 1st Sakura-cho, Hino City, Tokyo Konica Stock Company In-house

Claims (2)

[Claims] 1. An inkjet recording liquid containing a dye represented by the following general formula (1). Embedded image [Wherein R ₁ and R ₂ each represent a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, an aralkyl group, an aromatic residue or a heterocyclic residue, and R ₁ may form a ring together with R _2. good. R ₃ represents an amino group, an acylamino group, a sulfonylamino group, an alkoxy group, an alkyl group, an alkoxycarbonyl group, a carbamoyl group, a carboxyl group or a cyano group. R ₄ represents a hydrogen atom, an alkyl group, an alkoxy group, an acylamino group, a sulfonylamino group, an alkoxycarbonylamino group, a ureido group or a halogen atom. m represents an integer of 0 to 2. R ₅ is a halogen atom,
Alkyl group, alkoxy group, amino group, sulfo group, carboxyl group, sulfamoyl group, carbamoyl group, alkoxycarbonyl group, hydroxy group, acylamino group,
It represents a sulfonylamino group, a ureido group or an alkoxycarbonylamino group. n represents an integer of 0 to 5, and when n is 2 or more, R ₅ may be different from each other. X ₁ , X
_{One of 2} represents CR ₆ (R ₆ represents a hydrogen atom, an alkyl group, an acylamino group, a sulfonylamino group, a ureido group, an alkoxycarbonylamino group, a halogen atom or an alkoxy group), and the other represents a nitrogen atom. ] 2. The inkjet recording liquid according to claim 1, wherein the dye represented by the general formula (1) is a dye represented by the following general formula (2). Embedded image Wherein, R ₇ and R ₈ are each an alkyl group, an aralkyl group, R ₇ may form a ring with R _8. R ₉ represents an amino group or an acylamino group. R ₁₀ is a hydrogen atom,
It represents an alkyl group or an acylamino group. o represents an integer of 0 to 2. R ₁₁ represents a halogen atom or a sulfo group. p represents an integer of 0 to 5, and when p is 2 or more, R ₁₁
May be different from each other. One of X ₃ and X ₄ is CR
₁₂ (R ₁₂ represents a hydrogen atom, an alkyl group or an acylamino group), and the other represents a nitrogen atom. ]