WO2017146070A1 - Compound, coloring composition, ink for ink jet recording, ink jet recording method, and ink jet printer cartridge - Google Patents

Abstract

The present invention provides: a compound represented by general formula (1) disclosed in the description; a coloring composition comprising the compound; an ink for ink jet recording; an ink jet recording method that uses the ink for ink jet recording; and an ink jet printer cartridge.

Description

COMPOUND, COLORING COMPOSITION, INKJET RECORDING INK, INKJET RECORDING METHOD, AND INKJET PRINTER CARTRIDGE

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. In particular, in color printing, technical development has recently been carried out as an image forming method that can replace photographs. .

For example, 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.

Japanese Unexamined Patent Publication No. 2011-148773

However, in the field of dyes, further improvement in performance is required, and a compound capable of further improving image fastness such as light resistance and moisture resistance is required.

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.

As a result of intensive studies, the present inventors have found that the above problem can be solved by the compound represented by the general formula (1). In 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). Although the mechanism of action by which light resistance and moisture resistance are improved by the compound having this structure is unknown, the light resistance is improved due to steric protection around the nitrogen atom which is considered to be easily decomposed, and the silica in the image receiving paper is improved. Alternatively, it is considered that the moisture resistance is improved by the interaction between alumina and a carboxyl group bonded via the linking group.
That is, the present invention is as follows.

<1>
A compound represented by the following general formula (1).

In general formula (1),
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. Represents a residue obtained by removing m hydrogen atoms from a substituted or unsubstituted alkoxyalkyl 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.
<2>
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 a substituted or unsubstituted arylthio group.
<3>
The compound according to <1> or <2>, wherein R ³ and R ⁷ each independently represent a substituted or unsubstituted alkyl group.
<4>
The compound according to any one of <1> to <3>, wherein R ⁴ and R ⁸ represent a hydrogen atom.
<5>
<1>-<4> A colored composition containing the compound according to any one of <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>.

According to the present invention, 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.

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.

Hereinafter, the present invention will be described in detail.
First, specific examples of the substituent in the present invention are defined as a substituent group A.

(Substituent group A)
Halogen atom, alkyl group, aralkyl group, alkenyl group, alkynyl group, aryl group, heterocyclic group, cyano group, hydroxyl group, nitro group, alkoxy group, aryloxy group, silyloxy group, heterocyclic oxy group, acyloxy group, carbamoyl Oxy group, alkoxycarbonyloxy group, aryloxycarbonyloxy group, amino group, acylamino group, aminocarbonylamino group, alkoxycarbonylamino group, aryloxycarbonylamino group, sulfamoylamino group, alkyl or arylsulfonylamino group, mercapto Group, alkylthio group, arylthio group, heterocyclic thio group, sulfamoyl group, alkyl or arylsulfinyl group, alkyl or arylsulfonyl group, acyl group, aryloxycarbonyl group, Job aryloxycarbonyl group, a carbamoyl group, an aryl or heterocyclic azo group, an imido group, a phosphino group, phosphinyl group, phosphinyloxy group, phosphinylamino group, a silyl group, an ionic hydrophilic group mentioned as an example. These substituents may be further substituted, and examples of the further substituent include a group selected from the substituent group A described above.

Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

Examples of the alkyl group 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.
As the 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, and 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.

Examples of the aralkyl group 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.

Examples of the alkenyl group 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. Preferred examples of the cycloalkenyl group 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. As the 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 A monovalent group obtained by removing one hydrogen atom from a bicycloalkene having one of, for example, bicyclo [2,2,1] Hept-2-en-1-yl group, a bicyclo [2,2,2] oct-2-en-4-yl group and the like.

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. Examples of 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.

Preferred examples of the silyloxy group 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.

As the 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. Examples of 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. Butylsulfonylamino group, phenylsulfonylamino group, 2,3,5-trichlorophenylsulfonylamino group, p-methylphenylsulfonylamino group, and the like.
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.

Preferred examples of the heterocyclic thio group 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.

Preferred examples of the silyl group 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 ionic hydrophilic group may be in a state containing a cation or an anion (also referred to as “salt state”). For example, 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.

In the present invention, when the compound is a salt, the salt is dissociated into ions in the water-soluble ink.

[Compound represented by the general formula (1)]
The compound represented by the following general formula (1) will be described.
General formula (1)

In general formula (1),
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. Represents a residue obtained by removing m hydrogen atoms from a substituted or unsubstituted alkoxyalkyl 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 Preferably represents an oxycarbonyl group, a substituted or unsubstituted sulfamoyl group, a mercapto group, a substituted or unsubstituted alkylthio group, or a substituted or unsubstituted arylthio group, and represents a hydrogen atom or a substituted or unsubstituted alkyl group It is more preferable.

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.

It is preferable that 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 hydrogen atoms from an alkoxyalkyl group (for example, methoxymethyl group, ethoxyethyl group).
L may have a substituent, and examples of the substituent include a substituent selected from the above substituent group A.

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.

Specific examples of the compound represented by the general formula (1) are given below, but are not limited thereto. In the structural formulas of the following specific compounds, Me represents a methyl group.

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.

(Coloring composition)
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.

In the present invention, 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. However, 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.

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. Examples of other additives include additives that can be used in ink jet recording inks described later.

[Ink for inkjet recording]
Next, the ink for inkjet recording of the present invention will be described.
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. Preferably, 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. Other 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.

Examples of additives that can be used in the present invention include those described in JP-A-2013-133394, [0091] to [0101]. Regarding the usage form and usage method, the contents described in the above-mentioned patent documents can be preferably referred to.

It is preferable that 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. In addition, in the ink for inkjet recording of the present invention, 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 | dyes together, it is preferable that the sum total of content of a pigment | dye is the said range.

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. In particular, 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.

[Inkjet 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.

[Inkjet printer cartridge and inkjet recording]
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.

Hereinafter, a recording paper and a recording film used for ink jet printing using the ink of the present invention will be described.
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. Mechanical pulp, DIP (De- Inked Pulp), etc., and if necessary, additives such as conventionally known pigments, binders, sizing agents, fixing agents, cationic agents, paper strength enhancers, etc. What was manufactured with various apparatuses, such as a paper machine, can be used. In addition to these supports, either synthetic paper or plastic film sheets may be used. The thickness of the support is preferably 10 to 250 μm 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. When a polymer latex having a low glass transition temperature (40 ° C. or lower) is added to a layer containing a mordant, cracking and curling of the layer can be prevented. Also, 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, and 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. For example, 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.

Hereinafter, the present invention will be described in detail with reference to examples, but the present invention is not limited to these examples. Unless otherwise specified, “%” and “parts” in the examples are% by mass and parts by mass.

[Synthesis Example] Synthesis of Exemplary Compound 1 Exemplary Compound 1 can be synthesized, for example, according to the following scheme.

(Synthesis of Intermediate C)
Intermediate A (synthesized by the method described in paragraph No. 0138 of WO2015 / 105108A1) 4.18 g was dissolved in 80 mL of N, N-dimethylacetamide (DMAc), and intermediate B (pages 20 to 21 of WO2011 / 103321A1) was dissolved therein. 6.1 g) was added and reacted at 20 ° C. for 2 hours. The obtained reaction solution was poured into ethyl acetate, decanted, and the resulting residue was subjected to column chromatography (filler: Sephadex LH-20 (trade name, manufactured by Pharmacia), developing solvent: water / methanol = 1: 1. (V / v)) to obtain Intermediate C. Yield 5.0 g, yield 80%. Mass spectrum (MS): m / z = 1231 ([M−1] ⁻ , 100%).

(Synthesis of Exemplified Compound 1)
Intermediate C 4.7g was dissolved in water 50g, 50% sodium hydroxide aqueous solution 5g was added here, and it stirred at 20 degreeC for 30 minutes. After adjusting the pH to 7 with dilute hydrochloric acid, the inorganic salt was removed using a dialysis tube (Spectra / Por3, trade name, manufactured by Spectrum Laboratories), and then concentrated and dried using a rotary evaporator. The resulting residue was purified by column chromatography (filler: Sephadex LH-20, manufactured by Pharmacia, trade name, developing solvent: water / methanol = 1: 1 (v / v)), and then the pH was adjusted with sodium hydroxide. The crystals of Exemplified Compound 1 were obtained by adjusting to 8.5, removing dust using a membrane filter (Advantech, pore size 0.2 μm), 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. Moreover, the absorption spectrum in the dilute aqueous solution of exemplary compound 1 is shown in FIG. As shown in FIG. 2, the absorption maximum wavelength in the absorption spectrum of Exemplified Compound 1 in a dilute aqueous solution was 533 nm.

[Preparation of ink]
[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 μm 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.

(Image recording and evaluation)
The following evaluation was performed on the inks for ink jet recording in each of the examples and comparative examples. The results are shown in Table 1.
In Table 1, the light resistance and the moisture resistance are as follows: each ink jet recording ink is loaded into an ink cartridge, and photographic paper (trade name, Seiko) is printed with an ink jet printer (PX-205, trade name, manufactured by Seiko Epson Corporation). Evaluation was performed after recording an image on Epson Corporation.

<Light resistance-Condition (1)>
After measuring the image density Ci immediately after recording, the image was irradiated with xenon light (100,000 lux) for 14 days using a xenon weather meter (7.5 kW low-temperature cycle xenon weather meter XL75 manufactured by Suga Test Instruments), and again The image density Cf was measured, and the dye residual ratio (Cf / Ci × 100%) was calculated from the image density before and after the xenon light irradiation and evaluated. The image density was measured using a reflection densitometer (X-Rite i1, trade name, manufactured by X-Rite). The dye residual ratio was measured using an image portion having an initial image density of 1.0 ± 0.2. As evaluation criteria, the residual ratio of the dye was evaluated in three stages, with A being 80% or more, B being 60% or more and less than 80%, and C being less than 60%.

<Light resistance-Condition (2)>
Evaluation was carried out in the same manner except that the exposure period of the above light resistance-condition (1) was irradiated for 14 days to 28 days. As evaluation criteria, the residual ratio of the dye was evaluated as 4 levels, with S being 80% or more, A being 75% to less than 80%, B being 70% to less than 75%, and C being less than 70%.

<Moisture resistance-Condition (1)>
A 3 cm × 3 cm print pattern was prepared by arranging magenta 1 mm × 1 mm squares so that a 0.5 mm white gap was formed between the squares. This image sample was 45 ° C. with a relative humidity of 85%. Under the condition, after storage for 168 hours, bleeding of the magenta dye in the white space was observed.
Specifically, the OD (Optical Density) value of the printed material before and after being exposed to the high humidity condition was measured using a reflection densitometer (X-rite i1, trade name, manufactured by X-Rite). In the green filter of status A, the increase in white magenta density immediately after printing is A when less than 0.02, B when 0.02 or more and less than 0.05, and C when 0.05 or more. Rated by stage.

<Moisture resistance-Condition (2)>
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.
As 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. In a status A green filter, 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, and C is 0.1 or more. Evaluation was made in 4 stages.

 

 

As is apparent from the results in Table 1, the inks of the examples using the compounds of the present invention were excellent in all of light resistance and moisture resistance.
In the following structural formulas, Me represents a methyl group.

Comparative compound 1

Comparative compound 2

Comparative compound 3

According to the present invention, 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.

Although the present invention has been described in detail and with reference to specific embodiments, it will be apparent to those skilled in the art that various changes and modifications can be made without departing from the spirit and scope of the invention.
This application is based on a Japanese patent application filed on Feb. 25, 2016 (Japanese Patent Application No. 2016-034747), the contents of which are incorporated herein by reference.

Claims (8)

A compound represented by the following general formula (1).

In general formula (1),
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. Represents a residue obtained by removing m hydrogen atoms from a substituted or unsubstituted alkoxyalkyl 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 The compound according to claim 1, which represents an aryloxycarbonyl group, a substituted or unsubstituted sulfamoyl group, a mercapto group, a substituted or unsubstituted alkylthio group, or a substituted or unsubstituted arylthio group. The compound according to claim 1 or 2, wherein each of R ³ and R ⁷ independently represents a substituted or unsubstituted alkyl group. The compound according to any one of claims 1 to 3, wherein R ⁴ and R ⁸ represent a hydrogen atom. A coloring composition containing the compound according to any one of claims 1 to 4. An inkjet recording ink containing the compound according to any one of claims 1 to 4. An ink jet recording method using the ink for ink jet recording according to claim 6. An ink jet printer cartridge filled with the ink for ink jet recording according to claim 6.

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