JP6839723B2 - Coloring composition, ink for inkjet recording, inkjet recording method, and inkjet printer cartridge - Google Patents

Description

The present invention relates to a coloring composition, an ink for inkjet recording, an inkjet recording method, and an inkjet printer cartridge.

As is well known, the inkjet recording method is a method of printing by flying small droplets of ink and adhering them to a recording medium such as paper. This printing method can print high-resolution, high-quality images at high speed and easily with an inexpensive device. Especially in color printing, technological development has been carried out in recent years as an image forming method that can replace photographs. ..

For example, Patent Documents 1 and 2 describe inks for inkjet recording containing a xanthene compound.

Japanese Patent Application Laid-Open No. 2013-133395 International Publication No. 2015/105108

However, in the field of dyes, further improvement in performance is required.

INDUSTRIAL APPLICABILITY The present invention can form an image having excellent hue, saturation, coloring power (print density), excellent light resistance, ozone resistance, and moisture resistance, and is also excellent in ejection stability in an inkjet printer. It is an object of the present invention to provide a coloring composition, an inkjet recording ink using the coloring composition, an inkjet recording method using the inkjet recording ink, and an inkjet printer cartridge filled with the inkjet recording ink.

The present inventors have diligently studied and found that the above problems can be solved by the following means. In the present invention, by combining the compound represented by the general formula (1) and the azo compound represented by the general formula (D), the dye concentration contained in the coloring composition (ink) is reduced (ink). While contributing to the improvement of ejection stability), it is possible to achieve both high coloring power (print density) and image fastness (light resistance, ozone resistance, and moisture resistance). In the present invention, by combining different pigment mother nuclei having good hue and saturation and high coloring power, it is possible to satisfy the coloring power and image fastness at a higher level than when each of them is used alone. Conceivable.
Although the detailed reason is not clear, when the xanthene dye represented by the general formula (1) and the azo dye represented by the general formula (D) are mixed (for example, in an ink for inkjet recording or an inkjet recording method). It is presumed that the required performance was achieved without causing a large drawback such as a decrease in light resistance and a decrease in ink ejection stability because there was little physicochemical interaction with the inkjet prints created using ing.

[1]
A coloring composition containing a compound represented by the following general formula (1) and a compound represented by the following general formula (D).
When the content _{W 1} of the compound represented by the following general formula _{(1), W 1 / W} D 99/1 is the mass ratio of the content of _{W D} of the compound represented by the following general formula (D) A coloring composition of 50/50.

In the general formula (1), R ¹ , R ⁵ , R ⁶ and R ¹⁰ each independently represent an alkyl group. R ⁴ , R ⁹ , R ¹¹ , R ¹² , R ¹³ , R ¹⁴ , R ¹⁵ , R ¹⁶ , R ¹⁷ , R ¹⁸ , R ¹⁹ and R ²⁰ each independently represent a hydrogen atom or substituent. R ² , R ³ , R ⁷ and R ⁸ each independently represent a hydrogen atom, an alkyl group or a substituent represented by the following general formula (A), and at least of ^{R 2} , R ³ , R ⁷ and R ⁸ One represents a substituent represented by the following general formula (A).

In the general formula (A), X represents a substituent represented by the following general formula (X1), general formula (X2) or general formula (X3). * Represents a bond that binds to the benzene ring.

In the general formula (X1), R ⁴⁰¹ , R ⁴⁰² , R ⁴⁰³ , R ⁴⁰⁴ and R ⁴⁰⁵ each independently represent a hydrogen atom or a substituent. However, R ⁴⁰¹ , R ⁴⁰² , R ⁴⁰³ , R ⁴⁰⁴ and R ⁴⁰⁵ satisfy the following conditions (i) or (ii). * Represents a bond that binds to a sulfur atom.
Condition (i): At ^{least one of R 401} , R ⁴⁰² , R ⁴⁰³ , R ⁴⁰⁴ and R ⁴⁰⁵ represents a hydroxyl group, and at least one represents a carboxyl group.
Condition (ii): At ^{least two of R 401} , R ⁴⁰² , R ⁴⁰³ , R ⁴⁰⁴ and R ⁴⁰⁵ represent a carboxyl group.

In the general formula (X2), R ⁵⁰¹ , R ⁵⁰² , R ⁵⁰³ , R ⁵⁰⁴ , R ⁵⁰⁵ , R ⁵⁰⁶ and R ⁵⁰⁷ each independently represent a hydrogen atom or a substituent. However, R ⁵⁰¹ , R ⁵⁰² , R ⁵⁰³ , R ⁵⁰⁴ , R ⁵⁰⁵ , R ⁵⁰⁶ and R ⁵⁰⁷ satisfy the following conditions (iii) or (iv). * Represents a bond that binds to a sulfur atom.
Condition (iii): At ^{least one of R 501} , R ⁵⁰² , R ⁵⁰³ , R ⁵⁰⁴ , R ⁵⁰⁵ , R ⁵⁰⁶ and R ⁵⁰⁷ represents a hydroxyl group, and at least one represents a carboxyl group.
Condition (iv): At ^{least two of R 501} , R ⁵⁰² , R ⁵⁰³ , R ⁵⁰⁴ , R ⁵⁰⁵ , R ⁵⁰⁶ and R ⁵⁰⁷ represent a carboxyl group.

In the general formula (X3), R ⁶⁰¹ and R ⁶⁰² , R ⁶⁰³ , R ⁶⁰⁴ , R ⁶⁰⁵ , R ⁶⁰⁶ and R ⁶⁰⁷ each independently represent a hydrogen atom or a substituent. However, R ⁶⁰¹ and R ⁶⁰² , R ⁶⁰³ , R ⁶⁰⁴ , R ⁶⁰⁵ , R ⁶⁰⁶ and R ⁶⁰⁷ satisfy the following conditions (v) or (vi). * Represents a bond that binds to a sulfur atom.
Condition (v): At ^{least one of R 601} and R ⁶⁰² , R ⁶⁰³ , R ⁶⁰⁴ , R ⁶⁰⁵ , R ⁶⁰⁶ and R ⁶⁰⁷ represents a hydroxyl group, and at least one represents a carboxyl group.
Condition (vi): At ^{least two of R 601} , R ⁶⁰² , R ⁶⁰³ , R ⁶⁰⁴ , R ⁶⁰⁵ , R ⁶⁰⁶ and R ⁶⁰⁷ represent a carboxyl group.

In the general formula (D), Y ₁ and Y ₂ each independently represent a hydrogen atom or a substituent. Z _{1 to} Z ₅ independently represent a hydrogen atom or a substituent. M ₁ and M ₂ independently represent a hydrogen atom, an ammonium ion, an alkali metal ion or an organic cation, respectively.
[2]
X in the general formula (A) represents a substituent represented by the general formula (X1), and R ⁴⁰¹ , R ⁴⁰² , R ⁴⁰³ , R ⁴⁰⁴ and R ^{405 in the} general formula (X1) are the above. The coloring composition according to [1], which satisfies the condition (i).
[3]
X in the general formula (A) represents a substituent represented by the general formula (X2), and R ⁵⁰¹ , R ⁵⁰² , R ⁵⁰³ , R ⁵⁰⁴ , R ⁵⁰⁵ , R in the general formula (X2). The coloring composition according to [1], wherein ⁵⁰⁶ and R ^{507 satisfy the above condition (iii).}
[4]
X in the general formula (A) represents a substituent represented by the general formula (X3), and R ⁶⁰¹ , R ⁶⁰² , R ⁶⁰³ , R ⁶⁰⁴ , R ⁶⁰⁵ , R in the general formula (X3). The coloring composition according to [1], wherein ⁶⁰⁶ and R ^{607 satisfy the above condition (v).}
[5]
The total content of the compound represented by the general formula (1) and the compound represented by the general formula (D) is 1.5 to 5.0% by mass in the coloring composition [1] to The coloring composition according to any one of [4].
[6]
The _W 1 / _{W D} is 95 / 5-90 / 10 [1] - coloring composition according to any one of [5].
[7]
The coloring composition according to any one of [1] to [6], which further contains a coloring material other than the compound represented by the general formula (1) and the compound represented by the general formula (D).
[8]
An ink for inkjet recording using the coloring composition according to any one of [1] to [7].
[9]
An inkjet recording method using the inkjet recording ink according to [8].
[10]
An inkjet printer cartridge filled with the ink for inkjet recording according to [8].
The present invention is the invention according to the above [1] to [10], but other matters are also described below for reference.
<1>
A coloring composition containing a compound represented by the following general formula (1) and a compound represented by the following general formula (D).
When the content _{W 1} of the compound represented by the following general formula _{(1), W 1 / W} D 99/1 is the mass ratio of the content of _{W D} of the compound represented by the following general formula (D) A coloring composition of 50/50.

In the general formula (1), R ¹ , R ⁵ , R ⁶ and R ¹⁰ each independently represent an alkyl group. R ⁴ , R ⁹ , R ¹¹ , R ¹² , R ¹³ , R ¹⁴ , R ¹⁵ , R ¹⁶ , R ¹⁷ , R ¹⁸ , R ¹⁹ and R ²⁰ each independently represent a hydrogen atom or substituent. R ² , R ³ , R ⁷ and R ⁸ each independently represent a hydrogen atom, an alkyl group or a substituent represented by the following general formula (A), and at least of ^{R 2} , R ³ , R ⁷ and R ⁸ One represents a substituent represented by the following general formula (A).

In the general formula (A), X represents a substituent represented by the following general formula (X1), general formula (X2) or general formula (X3). * Represents a bond that binds to the benzene ring.

In the general formula (X1), R ⁴⁰¹ , R ⁴⁰² , R ⁴⁰³ , R ⁴⁰⁴ and R ⁴⁰⁵ each independently represent a hydrogen atom or a substituent. However, R ⁴⁰¹ , R ⁴⁰² , R ⁴⁰³ , R ⁴⁰⁴ and R ⁴⁰⁵ satisfy the following conditions (i) or (ii). * Represents a bond that binds to a sulfur atom.
Condition (i): At ^{least one of R 401} , R ⁴⁰² , R ⁴⁰³ , R ⁴⁰⁴ and R ⁴⁰⁵ represents a hydroxyl group, and at least one represents a carboxyl group.
Condition (ii): At ^{least two of R 401} , R ⁴⁰² , R ⁴⁰³ , R ⁴⁰⁴ and R ⁴⁰⁵ represent a carboxyl group.

In the general formula (X2), R ⁵⁰¹ , R ⁵⁰² , R ⁵⁰³ , R ⁵⁰⁴ , R ⁵⁰⁵ , R ⁵⁰⁶ and R ⁵⁰⁷ each independently represent a hydrogen atom or a substituent. However, R ⁵⁰¹ , R ⁵⁰² , R ⁵⁰³ , R ⁵⁰⁴ , R ⁵⁰⁵ , R ⁵⁰⁶ and R ⁵⁰⁷ satisfy the following conditions (iii) or (iv). * Represents a bond that binds to a sulfur atom.
Condition (iii): At ^{least one of R 501} , R ⁵⁰² , R ⁵⁰³ , R ⁵⁰⁴ , R ⁵⁰⁵ , R ⁵⁰⁶ and R ⁵⁰⁷ represents a hydroxyl group, and at least one represents a carboxyl group.
Condition (iv): At ^{least two of R 501} , R ⁵⁰² , R ⁵⁰³ , R ⁵⁰⁴ , R ⁵⁰⁵ , R ⁵⁰⁶ and R ⁵⁰⁷ represent a carboxyl group.

In the general formula (X3), R ⁶⁰¹ and R ⁶⁰² , R ⁶⁰³ , R ⁶⁰⁴ , R ⁶⁰⁵ , R ⁶⁰⁶ and R ⁶⁰⁷ each independently represent a hydrogen atom or a substituent. However, R ⁶⁰¹ and R ⁶⁰² , R ⁶⁰³ , R ⁶⁰⁴ , R ⁶⁰⁵ , R ⁶⁰⁶ and R ⁶⁰⁷ satisfy the following conditions (v) or (vi). * Represents a bond that binds to a sulfur atom.
Condition (v): At ^{least one of R 601} and R ⁶⁰² , R ⁶⁰³ , R ⁶⁰⁴ , R ⁶⁰⁵ , R ⁶⁰⁶ and R ⁶⁰⁷ represents a hydroxyl group, and at least one represents a carboxyl group.
Condition (vi): At ^{least two of R 601} , R ⁶⁰² , R ⁶⁰³ , R ⁶⁰⁴ , R ⁶⁰⁵ , R ⁶⁰⁶ and R ⁶⁰⁷ represent a carboxyl group.

In the general formula (D), Y ₁ and Y ₂ each independently represent a hydrogen atom or a substituent. Z _{1 to} Z ₅ independently represent a hydrogen atom or a substituent. M ₁ and M ₂ independently represent a hydrogen atom, an ammonium ion, an alkali metal ion or an organic cation, respectively.
<2>
X in the general formula (A) represents a substituent represented by the general formula (X1), and R ⁴⁰¹ , R ⁴⁰² , R ⁴⁰³ , R ⁴⁰⁴ and R ^{405 in the} general formula (X1) are the above. The coloring composition according to <1>, which satisfies the condition (i).
<3>
X in the general formula (A) represents a substituent represented by the general formula (X2), and R ⁵⁰¹ , R ⁵⁰² , R ⁵⁰³ , R ⁵⁰⁴ , R ⁵⁰⁵ , R in the general formula (X2). The coloring composition according to <1>, wherein ⁵⁰⁶ and R ^{507 satisfy the above condition (iii).}
<4>
X in the general formula (A) represents a substituent represented by the general formula (X3), and R ⁶⁰¹ , R ⁶⁰² , R ⁶⁰³ , R ⁶⁰⁴ , R ⁶⁰⁵ , R in the general formula (X3). The coloring composition according to <1>, wherein ⁶⁰⁶ and R ^{607 satisfy the above condition (v).}
<5>
The total content of the compound represented by the general formula (1) and the compound represented by the general formula (D) is 5.0% by mass or less in the coloring composition <1> to <4>. The coloring composition according to any one of the above.
<6>
The _W 1 / _{W D} is 95 / 5-90 / 10 <1> - coloring composition according to any one of <5>.
<7>
The coloring composition according to any one of <1> to <6>, which further contains a coloring material other than the compound represented by the general formula (1) and the compound represented by the general formula (D).
<8>
An ink for inkjet recording using the coloring composition according to any one of <1> to <7>.
<9>
An inkjet recording method using the inkjet recording ink according to <8>.
<10>
An inkjet printer cartridge filled with the ink for inkjet recording according to <8>.

According to the present invention, it is possible to form an image having excellent hue, saturation, coloring power (print density), and excellent light resistance, ozone resistance, and moisture resistance, and further, it is possible to improve ejection stability in an inkjet printer. It is also possible to provide an excellent coloring composition, an inkjet recording ink using the coloring composition, an inkjet recording method using the inkjet recording ink, and an inkjet printer cartridge filled with the inkjet recording ink.

^{It is a figure which shows the 1} H-NMR (nuclear magnetic resonance) spectrum in the dimethyl sulfoxide-d6 of the example compound (1-11). It is a figure which shows ^{the 1} H-NMR spectrum in dimethyl sulfoxide-d6 of the example compound (1-18). It is a figure which shows ^{the 1} H-NMR spectrum in dimethyl sulfoxide-d6 of the example compound (1-26). It is a figure which shows ^{the 1} H-NMR spectrum in dimethyl sulfoxide-d6 of the example compound (1-30).

Hereinafter, the present invention will be described in detail.
First, a specific example of the substituent in the present invention is 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, alkoxycarbonyl group, carbamoyl group, aryl or heterocyclic azo group, Examples thereof include an imide group, a phosphino group, a phosphinyl group, a phosphinyloxy group, a phosphinylamino group, a silyl group, and an ionic hydrophilic group. These substituents may be further substituted, and examples of further substituents include groups 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, cyclically substituted or unsubstituted alkyl groups, and include cycloalkyl groups, bicycloalkyl groups, and tricyclostructures having many ring structures. Alkyl groups among the substituents described below (for example, alkoxy groups, alkyl groups of alkylthio groups) also represent alkyl groups of such a concept.
The alkyl group is preferably an alkyl group having 1 to 30 carbon atoms, for example, 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 and the like, and the cycloalkyl group is preferably a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, for example, a cyclohexyl group, a cyclopentyl group, or 4 Examples thereof include the -n-dodecylcyclohexyl group, 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. The removed monovalent groups, for example, bicyclo [1,2,2] heptan-2-yl group, bicyclo [2,2,2] octane-3-yl group and the like can be mentioned.

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. For example, a benzyl group and a 2-phenethyl group can be mentioned.

Examples of the alkenyl group include linear, branched, cyclically substituted or unsubstituted alkenyl groups, and include cycloalkenyl groups and bicycloalkenyl groups.
The alkenyl group preferably includes a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, for example, a vinyl group, an allyl group, a prenyl group, a geranyl group, an oleyl group and the like, and the cycloalkenyl group is preferable. Is a substituted or unsubstituted cycloalkenyl group having 3 to 30 carbon atoms, that is, a monovalent group from which one hydrogen atom of a cycloalkene having 3 to 30 carbon atoms has been removed, for example, a 2-cyclopentene-1-yl group. Examples thereof include 2-cyclohexene-1-yl group, and examples of the bicycloalkenyl group include 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 from which one hydrogen atom of a bicycloalkene having one is removed, for example, a bicyclo [2,2,1] hept-2-ene-1-yl group, a bicyclo [2,2,2] octo-2- Examples thereof include an en-4-yl group.

The alkynyl group preferably includes a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, for example, 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, for example, 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 the number of carbon atoms. Examples include 3 to 30 5- or 6-membered aromatic heterocyclic groups such as 2-furyl group, 2-thienyl group, 2-pyrimidinyl group, 2-benzothiazolyl group and the like. Examples of non-aromatic heterocyclic groups include morpholinyl groups and the like.

The alkoxy group is preferably a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, for example, a methoxy group, an ethoxy group, an isopropoxy group, a t-butoxy group, an n-octyloxy group, or a 2-methoxyethoxy group. And so on.

The aryloxy group is preferably a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, for example, a phenoxy group, a 2-methylphenoxy group, a 4-t-butylphenoxy group, a 3-nitrophenoxy group, 2 -Tetradecanoylaminophenoxy group and the like can be mentioned.

The silyloxy group preferably includes a substituted or unsubstituted silyloxy group having 0 to 20 carbon atoms, for example, a trimethylsilyloxy group, a diphenylmethylsilyloxy group and the like.

The heterocyclic oxy group preferably includes a substituted or unsubstituted heterocyclic oxy group having 2 to 30 carbon atoms, for example, a 1-phenyltetrazole-5-oxy group, a 2-tetrahydropyranyloxy group and the like.

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, for example, an acetyloxy group. Examples thereof include a pivaloyloxy group, a stearoyloxy group, a benzoyloxy group, a p-methoxyphenylcarbonyloxy group and the like.

The carbamoyloxy group is preferably a substituted or unsubstituted carbamoyloxy group having 1 to 30 carbon atoms, for example, an N, N-dimethylcarbamoyloxy group, an N, N-diethylcarbamoyloxy group, a 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, for example, a methoxycarbonyloxy group, an ethoxycarbonyloxy group, a t-butoxycarbonyloxy group, an n-octylcarbonyloxy group. And so on.

The aryloxycarbonyloxy group is preferably a substituted or unsubstituted aryloxycarbonyloxy group having 7 to 30 carbon atoms, for example, a phenoxycarbonyloxy group, a p-methoxyphenoxycarbonyloxy group, pn-hexadecyloxy. Examples thereof include a 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, and a substituted or absence of 6 to 30 carbon atoms. Substituted anilino groups, for example, methylamino group, dimethylamino group, anilino group, N-methyl-anilino group, diphenylamino group, triazinylamino group and the like can be mentioned.

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, for example, an acetylamino group. Examples thereof include a pivaloylamino group, a lauroylamino group, a benzoylamino group, a 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, for example, a carbamoylamino group, an N, N-dimethylaminocarbonylamino group, an N, N-diethylaminocarbonylamino group. , Morphorinocarbonylamino group and the like.

The alkoxycarbonylamino group is preferably a substituted or unsubstituted alkoxycarbonylamino group having 2 to 30 carbon atoms, for example, a methoxycarbonylamino group, an ethoxycarbonylamino group, a t-butoxycarbonylamino group, an n-octadecyloxycarbonylamino. Examples include a group, an N-methyl-methoxycarbonylamino group and the like.

The aryloxycarbonylamino group is preferably a substituted or unsubstituted aryloxycarbonylamino group having 7 to 30 carbon atoms, for example, a phenoxycarbonylamino group, a p-chlorophenoxycarbonylamino group, an mn-octyloxyphenoxy. Examples include a carbonylamino group.

The sulfamoylamino group is preferably a substituted or unsubstituted sulfamoylamino group having 0 to 30 carbon atoms, for example, a sulfamoylamino group, an N, N-dimethylaminosulfonylamino group, Nn-. Examples thereof include an 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, for example, a methylsulfonylamino group. , Butylsulfonylamino group, phenylsulfonylamino group, 2,3,5-trichlorophenylsulfonylamino group, p-methylphenylsulfonylamino group and the like.
The alkylthio group preferably includes a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, for example, a methylthio group, an ethylthio group, an n-hexadecylthio group and the like.

The arylthio group preferably includes a substituted or unsubstituted arylthio group having 6 to 30 carbon atoms, for example, a phenylthio group, a p-chlorophenylthio group, an m-methoxyphenylthio group and the like.

The heterocyclic thio group preferably includes a substituted or unsubstituted heterocyclic thio group having 2 to 30 carbon atoms, for example, a 2-benzothiazolylthio group, a 1-phenyltetrazole-5-ylthio group and the like.

The sulfamoyl group is preferably a substituted or unsubstituted sulfamoyl group having 0 to 30 carbon atoms, for example, an N-ethylsulfamoyl group, an N- (3-dodecyloxypropyl) sulfamoyl group, N, N-dimethylsul. Examples thereof include a famoyl group, an N-acetylsulfamoyl group, an N-benzoyl sulfamoyl group, an N- (N'-phenylcarbamoyl) sulfamoyl group and the like.

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, for example, 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, for example, a methylsulfonyl group or an ethylsulfonyl group. , Phenylsulfonyl group, p-methylphenylsulfonyl group and the like.

As the acyl group, 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 no substituted carbonyl group having 2 to 30 carbon atoms is preferable. A heterocyclic carbonyl group bonded to a carbonyl group at a substituted carbon atom, such as an acetyl group, a pivaloyl group, a 2-chloroacetyl group, a stearoyl group, a benzoyl group, a pn-octyloxyphenylcarbonyl group, 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, for example, a phenoxycarbonyl group, an o-chlorophenoxycarbonyl group, an m-nitrophenoxycarbonyl group, pt-. Examples include a butylphenoxycarbonyl group.

Preferred examples of the alkoxycarbonyl group include a substituted or unsubstituted alkoxycarbonyl group having 2 to 30 carbon atoms, for example, a methoxycarbonyl group, an ethoxycarbonyl group, a t-butoxycarbonyl group, an n-octadecyloxycarbonyl group and the like.

The carbamoyl group is preferably a substituted or unsubstituted carbamoyl group having 1 to 30 carbon atoms, for example, a carbamoyl group, an N-methylcarbamoyl group, an N, N-dimethylcarbamoyl group, an N, N-di-n-octyl. Examples thereof include a carbamoyl group and an N- (methylsulfonyl) carbamoyl group.

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, for example, a phenylazo group or p-chlorophenylazo. Groups, 5-ethylthio-1,3,4-thiadiazole-2-ylazo group and the like can be mentioned.

The imide group preferably includes an N-succinimide group, an N-phthalimide group and the like.

The phosphino group preferably includes a substituted or unsubstituted phosphino group having 0 to 30 carbon atoms, for example, a dimethylphosphino group, a diphenylphosphino group, a methylphenoxyphosphino group and the like.

The phosphinyl group preferably includes a substituted or unsubstituted phosphinyl group having 0 to 30 carbon atoms, for example, a phosphinyl group, a dioctyloxyphosphinyl group, a diethoxyphosphinyl group and the like.

The phosphinyloxy group preferably includes a substituted or unsubstituted phosphinyloxy group having 0 to 30 carbon atoms, for example, a diphenoxyphosphinyloxy group, a dioctyloxyphosphinyloxy group and the like.

The phosphinylamino group preferably includes a substituted or unsubstituted phosphinylamino group having 0 to 30 carbon atoms, for example, a dimethoxyphosphinylamino group and a dimethylaminophosphinylamino group.

The silyl group preferably includes a substituted or unsubstituted silyl group having 0 to 30 carbon atoms, for example, a trimethylsilyl group, a t-butyldimethylsilyl group, a phenyldimethylsilyl group and the like.

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 preferably, it is a sulfo group or a carboxyl group. Further, the ionic hydrophilic group may contain a cation or an anion, and a state containing the cation or an anion is called a salt state. The carboxyl group, phosphono group and sulfo group may be in the salt state, and examples of counter cations forming the salt include ammonium ion, alkali metal ion (eg, lithium ion, sodium ion, potassium ion) and organic cation. (For example, tetramethylammonium ion, tetramethylguanidium ion, tetramethylphosphonium) are contained, and lithium salt, sodium salt, potassium salt, and ammonium salt are preferable, and sodium salt or a mixed salt containing a sodium salt as a main component is preferable. More preferably, sodium salt is most preferred.

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

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

In the general formula (1), R ¹ , R ⁵ , R ⁶ and R ¹⁰ each independently represent an alkyl group. R ⁴ , R ⁹ , R ¹¹ , R ¹² , R ¹³ , R ¹⁴ , R ¹⁵ , R ¹⁶ , R ¹⁷ , R ¹⁸ , R ¹⁹ and R ²⁰ each independently represent a hydrogen atom or substituent. R ² , R ³ , R ⁷ and R ⁸ each independently represent a hydrogen atom, an alkyl group or a substituent represented by the following general formula (A), and at least of ^{R 2} , R ³ , R ⁷ and R ⁸ One represents a substituent represented by the following general formula (A).

In the general formula (A), X represents a substituent represented by the following general formula (X1), general formula (X2) or general formula (X3). * Represents a bond that binds to the benzene ring.

In the general formula (X1), R ⁴⁰¹ , R ⁴⁰² , R ⁴⁰³ , R ⁴⁰⁴ and R ⁴⁰⁵ each independently represent a hydrogen atom or a substituent. However, R ⁴⁰¹ , R ⁴⁰² , R ⁴⁰³ , R ⁴⁰⁴ and R ⁴⁰⁵ satisfy the following conditions (i) or (ii). * Represents a bond that binds to a sulfur atom.
Condition (i): At ^{least one of R 401} , R ⁴⁰² , R ⁴⁰³ , R ⁴⁰⁴ and R ⁴⁰⁵ represents a hydroxyl group, and at least one represents a carboxyl group.
Condition (ii): At ^{least two of R 401} , R ⁴⁰² , R ⁴⁰³ , R ⁴⁰⁴ and R ⁴⁰⁵ represent a carboxyl group.

In the general formula (X2), R ⁵⁰¹ , R ⁵⁰² , R ⁵⁰³ , R ⁵⁰⁴ , R ⁵⁰⁵ , R ⁵⁰⁶ and R ⁵⁰⁷ each independently represent a hydrogen atom or a substituent. However, R ⁵⁰¹ , R ⁵⁰² , R ⁵⁰³ , R ⁵⁰⁴ , R ⁵⁰⁵ , R ⁵⁰⁶ and R ⁵⁰⁷ satisfy the following conditions (iii) or (iv). * Represents a bond that binds to a sulfur atom.
Condition (iii): At ^{least one of R 501} , R ⁵⁰² , R ⁵⁰³ , R ⁵⁰⁴ , R ⁵⁰⁵ , R ⁵⁰⁶ and R ⁵⁰⁷ represents a hydroxyl group, and at least one represents a carboxyl group.
Condition (iv): At ^{least two of R 501} , R ⁵⁰² , R ⁵⁰³ , R ⁵⁰⁴ , R ⁵⁰⁵ , R ⁵⁰⁶ and R ⁵⁰⁷ represent a carboxyl group.

In the general formula (X3), R ⁶⁰¹ and R ⁶⁰² , R ⁶⁰³ , R ⁶⁰⁴ , R ⁶⁰⁵ , R ⁶⁰⁶ and R ⁶⁰⁷ each independently represent a hydrogen atom or a substituent. However, R ⁶⁰¹ and R ⁶⁰² , R ⁶⁰³ , R ⁶⁰⁴ , R ⁶⁰⁵ , R ⁶⁰⁶ and R ⁶⁰⁷ satisfy the following conditions (v) or (vi). * Represents a bond that binds to a sulfur atom.
Condition (v): At ^{least one of R 601} and R ⁶⁰² , R ⁶⁰³ , R ⁶⁰⁴ , R ⁶⁰⁵ , R ⁶⁰⁶ and R ⁶⁰⁷ represents a hydroxyl group, and at least one represents a carboxyl group.
Condition (vi): At ^{least two of R 601} , R ⁶⁰² , R ⁶⁰³ , R ⁶⁰⁴ , R ⁶⁰⁵ , R ⁶⁰⁶ and R ⁶⁰⁷ represent a carboxyl group.

In the general formula (1), R ¹¹ , R ¹³ , R ¹⁴ , R ¹⁶ , R ¹⁷ , R ¹⁸ , R ¹⁹ and R ²⁰ each independently represent a hydrogen atom or a substituent. When R ¹¹ , R ¹³ , R ¹⁴ , R ¹⁶ , R ¹⁷ , R ¹⁸ , R ¹⁹ and R ²⁰ represent a substituent, the substituent includes a substituent selected from the above-mentioned Substituent Group A.
R ¹¹ , R ¹³ , R ¹⁴ , R ¹⁶ , R ¹⁷ , R ¹⁸ , R ¹⁹ and R ²⁰ preferably represent a hydrogen atom.

In the general formula (1), R ¹ , R ⁵ , R ⁶ and R ¹⁰ each independently represent an alkyl group, and an alkyl group having 1 to 6 carbon atoms is preferable from the viewpoint of availability of raw materials and ease of synthesis. , Alkyl groups having 1 to 3 carbon atoms are more preferable, and methyl groups or ethyl groups are even more preferable. Further, the ^{alkyl group represented by R 1} , R ⁵ , R ⁶ and R ¹⁰ may have a substituent, and examples of the substituent include a substituent selected from the above-mentioned Substituent Group A.

In the general formula (1), R ⁴ , R ⁹ , R ¹² and R ¹⁵ each independently represent a hydrogen atom or a substituent. When R ⁴ , R ⁹ , R ¹² and R ¹⁵ represent a substituent, an alkyl group or an ionic hydrophilic group is preferable as the substituent.
The alkyl group is preferably an alkyl group having 1 to 6 carbon atoms, more preferably an alkyl group having 1 to 3 carbon atoms, still more preferably a methyl group or an ethyl group, and particularly preferably a methyl group. ..
As the ionic hydrophilic group, a carboxyl group, a sulfo group or a phosphono group is preferable. Examples of the counter cation of the ionic hydrophilic group include hydrogen atom (proton), alkali metal cation (lithium ion, sodium ion, or potassium ion), ammonium ion, etc., and easy synthesis (handling as dye powder). From the viewpoint of ease of use), it is preferably an alkali metal cation.
At ^{least one of R 4} , R ⁹ , R ¹² and R ¹⁵ preferably represents an ionic hydrophilic group, and more preferably two or more represent an ionic hydrophilic group.
When R ¹² and R ¹⁵ represent an ionic hydrophilic group and R ⁴ and R ⁹ represent a hydrogen atom, or when R ⁴ and R ⁹ represent an ionic hydrophilic group and R ¹² and R ^{15 represent an ionic hydrophilic group.} It is preferable that it represents a hydrogen atom, and it is more preferable that R ¹² and R ¹⁵ represent an ionic hydrophilic group and R ⁴ and R ⁹ represent a hydrogen atom.
R ⁴ and R ⁹ preferably independently represent a hydrogen atom, a sulfo group or a carboxyl group, and more preferably represent a hydrogen atom or a sulfo group.
R ¹² and R ¹⁵ preferably independently represent a hydrogen atom, a sulfo group or a carboxyl group, and more preferably represent a hydrogen atom or a sulfo group.

In the general formula (1), R ² , R ³ , R ⁷ and R ⁸ independently represent a hydrogen atom, an alkyl group or a substituent represented by the above general formula (A), and are R ² , R ³ , R. ^At least one of 7 and R ⁸ represents a substituent represented by the above general formula (A).
When R ² , R ³ , R ⁷ and R ⁸ represent an alkyl group, an alkyl group having 1 to 6 carbon atoms is preferable, an alkyl group having 1 to 3 carbon atoms is more preferable, and a methyl group or an ethyl group is further preferable. Further, the ^{alkyl group represented by R 2} , R ³ , R ⁷ and R ⁸ may have a substituent, and examples of the substituent include a substituent selected from the above-mentioned Substituent Group A.
When R ² and R ⁷ each independently represent a substituent represented by the general formula (A) and R ³ and R ⁸ represent an alkyl group, or R ³ and R ⁸ each independently represent a general formula (A). It represents a substituent represented by a), and preferably if R ² and R ⁷ represents an alkyl group, a substituent R ² and R ⁷ is represented by the general formula (a) each independently and It ^{is more preferable that R 3} and R ⁸ represent an alkyl group.

In the general formula (A), X represents a substituent represented by the general formula (X1), the general formula (X2) or the general formula (X3).
The counter cation of the carboxyl group in the general formula (X1), the general formula (X2) or the general formula (X3) includes a hydrogen atom (proton), an alkali metal cation (lithium ion, sodium ion, or potassium ion), and ammonium. Examples thereof include ions, but alkali metal cations are preferable.

In the general formula (X1), R ⁴⁰¹ , R ⁴⁰² , R ⁴⁰³ , R ⁴⁰⁴ and R ⁴⁰⁵ each independently represent a hydrogen atom or a substituent. However, R ⁴⁰¹ , R ⁴⁰² , R ⁴⁰³ , R ⁴⁰⁴ and R ⁴⁰⁵ satisfy the following conditions (i) or (ii).
Condition (i): At ^{least one of R 401} , R ⁴⁰² , R ⁴⁰³ , R ⁴⁰⁴ and R ⁴⁰⁵ represents a hydroxyl group, and at least one represents a carboxyl group.
Condition (ii): At ^{least two of R 401} , R ⁴⁰² , R ⁴⁰³ , R ⁴⁰⁴ and R ⁴⁰⁵ represent a carboxyl group.

In the general formula (X1), ^{it is preferable that R 401} , R ⁴⁰² , R ⁴⁰³ , R ⁴⁰⁴ and R ⁴⁰⁵ satisfy the above condition (i). That is, ^{it is preferable that at least one of R 401} , R ⁴⁰² , R ⁴⁰³ , R ⁴⁰⁴ and R ⁴⁰⁵ represents a hydroxyl group, and at least one represents a carboxyl group.

Of R ⁴⁰¹ , R ⁴⁰² , R ⁴⁰³ , R ⁴⁰⁴ and R ⁴⁰⁵ , the number of hydroxyl groups is preferably 1 to 3, more preferably 1 to 2, and even more preferably 1. The number of carboxyl groups is more preferably 1 to 3, and even more preferably 1 to 2.
It is preferable ^{that R 403} represents a hydroxyl group and R ⁴⁰² represents a carboxyl group, or R ⁴⁰¹ represents a hydroxyl group and R ⁴⁰² represents a carboxyl group, and R ⁴⁰¹ represents a hydroxyl group and R. ^It is more preferable that 402 represents a carboxyl group.
When R ⁴⁰¹ , R ⁴⁰² , R ⁴⁰³ , R ⁴⁰⁴ , and R ⁴⁰⁵ represent a substituent, the substituent includes a substituent selected from the above-mentioned Substituent Group A, and an alkyl group or an alkoxy group is preferable, and the number of carbon atoms is preferable. Alkyl groups or alkoxy groups of 1 to 6 are more preferable, alkyl groups or alkoxy groups having 1 to 3 carbon atoms are further preferable, and methyl groups or methoxy groups are particularly preferable. Further, ^{as the substituent when R 401} , R ⁴⁰² , R ⁴⁰³ , R ⁴⁰⁴ , and R ⁴⁰⁵ represent a substituent, in another embodiment from the above, a carboxyl group, a chlorine atom, a nitro group, or trifluoromethyl. Groups are mentioned, with carboxyl groups, chlorine atoms, or nitro groups being more preferred, and carboxyl groups being even more preferred. In particular, when R ⁴⁰¹ represents a hydroxyl group and R ⁴⁰² represents a carboxyl group, it is preferable that R ⁴⁰⁴ is the above-mentioned substituent (carboxyl group, chlorine atom, nitro group, or trifluoromethyl group).

In the general formula (X1), when R ⁴⁰¹ , R ⁴⁰² , R ⁴⁰³ , R ⁴⁰⁴ and R ⁴⁰⁵ satisfy the above condition (ii), ^{it is preferable that R 402} and R ⁴⁰⁴ represent a carboxyl group.

Specific examples of the group represented by the general formula (X1) are shown below, but the present invention is not limited thereto. In the structural formula of the specific compound below, Me represents a methyl group. * Represents a bond that binds to a sulfur atom.

In the general formula (X2), R ⁵⁰¹ , R ⁵⁰² , R ⁵⁰³ , R ⁵⁰⁴ , R ⁵⁰⁵ , R ⁵⁰⁶ and R ⁵⁰⁷ each independently represent a hydrogen atom or a substituent. However, R ⁵⁰¹ , R ⁵⁰² , R ⁵⁰³ , R ⁵⁰⁴ , R ⁵⁰⁵ , R ⁵⁰⁶ and R ⁵⁰⁷ satisfy the following conditions (iii) or (iv).
Condition (iii): At ^{least one of R 501} , R ⁵⁰² , R ⁵⁰³ , R ⁵⁰⁴ , R ⁵⁰⁵ , R ⁵⁰⁶ and R ⁵⁰⁷ represents a hydroxyl group, and at least one represents a carboxyl group.
Condition (iv): At ^{least two of R 501} , R ⁵⁰² , R ⁵⁰³ , R ⁵⁰⁴ , R ⁵⁰⁵ , R ⁵⁰⁶ and R ⁵⁰⁷ represent a carboxyl group.

In the general formula (X2), ^{it is preferable that R 501} , R ⁵⁰² , R ⁵⁰³ , R ⁵⁰⁴ , R ⁵⁰⁵ , R ⁵⁰⁶ and R ⁵⁰⁷ satisfy the condition (iii). That is, ^{it is preferable that at least one of R 501} , R ⁵⁰² , R ⁵⁰³ , R ⁵⁰⁴ , R ⁵⁰⁵ , R ⁵⁰⁶ and R ⁵⁰⁷ represents a hydroxyl group, and at least one represents a carboxyl group.

When R ⁵⁰¹ , R ⁵⁰² , R ⁵⁰³ , R ⁵⁰⁴ , R ⁵⁰⁵ , R ⁵⁰⁶ and R ⁵⁰⁷ represent a substituent, a substituent selected from the above-mentioned Substituent Group A can be mentioned, and an alkyl group or an alkoxy group can be mentioned. Is preferable, an alkyl group or an alkoxy group having 1 to 6 carbon atoms is more preferable, an alkyl group or an alkoxy group having 1 to 3 carbon atoms is further preferable, and a methyl group or a methoxy group is particularly preferable.
Of R ⁵⁰¹ , R ⁵⁰² , R ⁵⁰³ , R ⁵⁰⁴ , R ⁵⁰⁵ , R ⁵⁰⁶ and R ⁵⁰⁷ , the number of hydroxyl groups is preferably 1 to 3, more preferably 1 to 2, and even more preferably 1. The number of carboxyl groups is more preferably 1 to 2, and even more preferably 1.
It is preferable ^{that R 504} represents a hydroxyl group and R ⁵⁰³ represents a carboxyl group, or R ⁵⁰⁴ represents a hydroxyl group and R ⁵⁰⁵ represents a carboxyl group, and R ⁵⁰⁴ represents a hydroxyl group and R. ^It is more preferable that 503 represents a carboxyl group.

Specific examples of the group represented by the general formula (X2) are shown below, but the present invention is not limited thereto. * Represents a bond that binds to a sulfur atom.

In the general formula (X3), R ⁶⁰¹ and R ⁶⁰² , R ⁶⁰³ , R ⁶⁰⁴ , R ⁶⁰⁵ , R ⁶⁰⁶ and R ⁶⁰⁷ each independently represent a hydrogen atom or a substituent. However, R ⁶⁰¹ and R ⁶⁰² , R ⁶⁰³ , R ⁶⁰⁴ , R ⁶⁰⁵ , R ⁶⁰⁶ and R ⁶⁰⁷ satisfy the following conditions (v) or (vi). * Represents a bond that binds to a sulfur atom.
Condition (v): At ^{least one of R 601} and R ⁶⁰² , R ⁶⁰³ , R ⁶⁰⁴ , R ⁶⁰⁵ , R ⁶⁰⁶ and R ⁶⁰⁷ represents a hydroxyl group, and at least one represents a carboxyl group.
Condition (vi): At ^{least two of R 601} , R ⁶⁰² , R ⁶⁰³ , R ⁶⁰⁴ , R ⁶⁰⁵ , R ⁶⁰⁶ and R ⁶⁰⁷ represent a carboxyl group.

In the general formula (X3), ^{it is preferable that R 601} , R ⁶⁰² , R ⁶⁰³ , R ⁶⁰⁴ , R ⁶⁰⁵ , R ⁶⁰⁶ and R ⁶⁰⁷ satisfy the condition (v). That is, ^{it is preferable that at least one of R 601} and R ⁶⁰² , R ⁶⁰³ , R ⁶⁰⁴ , R ⁶⁰⁵ , R ⁶⁰⁶ and R ⁶⁰⁷ represents a hydroxyl group, and at least one represents a carboxyl group.

When R ⁶⁰¹ , R ⁶⁰² , R ⁶⁰³ , R ⁶⁰⁴ , R ⁶⁰⁵ , R ⁶⁰⁶ and R ⁶⁰⁷ represent a substituent, a substituent selected from the above-mentioned Substituent Group A can be mentioned as an alkyl group or an alkoxy group. Is preferable, an alkyl group or an alkoxy group having 1 to 6 carbon atoms is more preferable, an alkyl group or an alkoxy group having 1 to 3 carbon atoms is further preferable, and a methyl group or a methoxy group is particularly preferable.
Of R ⁶⁰¹ and R ⁶⁰² , R ⁶⁰³ , R ⁶⁰⁴ , R ⁶⁰⁵ , R ⁶⁰⁶ and R ⁶⁰⁷ , the number of hydroxyl groups is preferably 1 to 3, more preferably 1 to 2, and even more preferably 1. The number of carboxyl groups is more preferably 1 to 2, and even more preferably 1.
It is preferable ^{that R 606} represents a hydroxyl group and R ⁶⁰⁵ represents a carboxyl group, or R ⁶⁰³ represents a hydroxyl group and R ⁶⁰² represents a carboxyl group, and R ⁶⁰⁶ represents a hydroxyl group and R. ^It is more preferable that 605 represents a carboxyl group.

Specific examples of the group represented by the general formula (X3) are shown below, but the present invention is not limited thereto. * Represents a bond that binds to a sulfur atom.

The compound represented by the general formula (1) is preferably a compound represented by the following general formula (2), general formula (3) or general formula (4).

In the general formula (2), R ¹ , R ⁵ , R ⁶ and R ¹⁰ each independently represent an alkyl group. R ⁴ , R ⁹ , R ¹¹ , R ¹² , R ¹³ , R ¹⁴ , R ¹⁵ , R ¹⁶ , R ¹⁷ , R ¹⁸ , R ¹⁹ and R ²⁰ each independently represent a hydrogen atom or substituent. R ³ and R ⁸ each independently represent a hydrogen atom or an alkyl group. R ⁴⁰¹ , R ⁴⁰² , R ⁴⁰³ , R ⁴⁰⁴ and R ⁴⁰⁵ each independently represent a hydrogen atom or substituent. However, R ⁴⁰¹ , R ⁴⁰² , R ⁴⁰³ , R ⁴⁰⁴ and R ⁴⁰⁵ satisfy the following conditions (i-1) or (ii-1). R ⁴⁰⁶ , R ⁴⁰⁷ , R ⁴⁰⁸ , R ⁴⁰⁹ and R ⁴¹⁰ each independently represent a hydrogen atom or substituent. However, R ⁴⁰⁶ , R ⁴⁰⁷ , R ⁴⁰⁸ , R ⁴⁰⁹ and R ⁴¹⁰ satisfy the following conditions (i-2) or (ii-2).
Condition (i-1): At ^{least one of R 401} , R ⁴⁰² , R ⁴⁰³ , R ⁴⁰⁴ and R ⁴⁰⁵ represents a hydroxyl group, and at least one represents a carboxyl group.
Condition (ii-1): At ^{least two of R 401} , R ⁴⁰² , R ⁴⁰³ , R ⁴⁰⁴ and R ⁴⁰⁵ represent a carboxyl group.
Condition (i-2): At ^{least one of R 406} , R ⁴⁰⁷ , R ⁴⁰⁸ , R ⁴⁰⁹ and R ⁴¹⁰ represents a hydroxyl group, and at least one represents a carboxyl group.
Condition (ii-2): At ^{least two of R 406} , R ⁴⁰⁷ , R ⁴⁰⁸ , R ⁴⁰⁹ and R ⁴¹⁰ represent a carboxyl group.

In the general formula (3), R ¹ , R ⁵ , R ⁶ and R ¹⁰ each independently represent an alkyl group. R ⁴ , R ⁹ , R ¹¹ , R ¹² , R ¹³ , R ¹⁴ , R ¹⁵ , R ¹⁶ , R ¹⁷ , R ¹⁸ , R ¹⁹ and R ²⁰ each independently represent a hydrogen atom or substituent. R ³ and R ⁸ each independently represent a hydrogen atom or an alkyl group. R ⁵⁰¹ , R ⁵⁰² , R ⁵⁰³ , R ⁵⁰⁴ , R ⁵⁰⁵ , R ⁵⁰⁶ and R ⁵⁰⁷ each independently represent a hydrogen atom or substituent. However, R ⁵⁰¹ , R ⁵⁰² , R ⁵⁰³ , R ⁵⁰⁴ , R ⁵⁰⁵ , R ⁵⁰⁶ and R ⁵⁰⁷ satisfy the following conditions (iii-1) or (iv-1). R ⁵⁰⁸ , R ⁵⁰⁹ , R ⁵¹⁰ , R ⁵¹¹ , R ⁵¹² , R ⁵¹³ and R ⁵¹⁴ each independently represent a hydrogen atom or substituent. However, R ⁵⁰⁸ , R ⁵⁰⁹ , R ⁵¹⁰ , R ⁵¹¹ , R ⁵¹² , R ⁵¹³ and R ⁵¹⁴ satisfy the following conditions (iii-2) or (iv-2).
Condition (iii-1): At ^{least one of R 501} , R ⁵⁰² , R ⁵⁰³ , R ⁵⁰⁴ , R ⁵⁰⁵ , R ⁵⁰⁶ and R ⁵⁰⁷ represents a hydroxyl group, and at least one represents a carboxyl group.
Condition (iv-1): At ^{least two of R 501} , R ⁵⁰² , R ⁵⁰³ , R ⁵⁰⁴ , R ⁵⁰⁵ , R ⁵⁰⁶ and R ⁵⁰⁷ represent a carboxyl group.
Condition (iii-2): At ^{least one of R 508} , R ⁵⁰⁹ , R ⁵¹⁰ , R ⁵¹¹ , R ⁵¹² , R ⁵¹³ and R ⁵¹⁴ represents a hydroxyl group and at least one represents a carboxyl group.
Condition (iv-2): At ^{least two of R 508} , R ⁵⁰⁹ , R ⁵¹⁰ , R ⁵¹¹ , R ⁵¹² , R ⁵¹³ and R ⁵¹⁴ represent a carboxyl group.

In the general formula (4), R ¹ , R ⁵ , R ⁶ and R ¹⁰ each independently represent an alkyl group. R ⁴ , R ⁹ , R ¹¹ , R ¹² , R ¹³ , R ¹⁴ , R ¹⁵ , R ¹⁶ , R ¹⁷ , R ¹⁸ , R ¹⁹ and R ²⁰ each independently represent a hydrogen atom or substituent. R ³ and R ⁸ each independently represent a hydrogen atom or an alkyl group. R ⁶⁰¹ and R ⁶⁰² , R ⁶⁰³ , R ⁶⁰⁴ , R ⁶⁰⁵ , R ⁶⁰⁶ and R ⁶⁰⁷ each independently represent a hydrogen atom or a substituent. However, R ⁶⁰¹ and R ⁶⁰² , R ⁶⁰³ , R ⁶⁰⁴ , R ⁶⁰⁵ , R ⁶⁰⁶ and R ⁶⁰⁷ satisfy the following conditions (v-1) or (vi-1). R ⁶⁰⁸ , R ⁶⁰⁹ , R ⁶¹⁰ , R ⁶¹¹ , R ⁶¹² , R ⁶¹³ and R ⁶¹⁴ each independently represent a hydrogen atom or substituent. However, R ⁶⁰⁸ , R ⁶⁰⁹ , R ⁶¹⁰ , R ⁶¹¹ , R ⁶¹² , R ⁶¹³ and R ⁶¹⁴ satisfy the following conditions (v-2) or (vi-2).
Condition (v-1): At ^{least one of R 601} and R ⁶⁰² , R ⁶⁰³ , R ⁶⁰⁴ , R ⁶⁰⁵ , R ⁶⁰⁶ and R ⁶⁰⁷ represents a hydroxyl group, and at least one represents a carboxyl group.
Condition (vi-1): At ^{least two of R 601} and R ⁶⁰² , R ⁶⁰³ , R ⁶⁰⁴ , R ⁶⁰⁵ , R ⁶⁰⁶ and R ⁶⁰⁷ represent a carboxyl group.
Condition (v-2): At ^{least one of R 608} , R ⁶⁰⁹ , R ⁶¹⁰ , R ⁶¹¹ , R ⁶¹² , R ⁶¹³ and R ⁶¹⁴ represents a hydroxyl group and at least one represents a carboxyl group.
Condition (vi-2): At ^{least two of R 608} , R ⁶⁰⁹ , R ⁶¹⁰ , R ⁶¹¹ , R ⁶¹² , R ⁶¹³ and R ⁶¹⁴ represent a carboxyl group.

^{R 1} , R ⁴ , R ⁵ , R ⁶ , R ⁹ , R ¹⁰ , R ¹¹ , R ¹² , R ¹³ , R ¹⁴ , R ¹⁵ , R ¹⁶ , R ¹⁷ , R ¹⁸ , R in the general formula (2) ¹⁹ and R ^{20 are R 1} , R ⁴ , R ⁵ , R ⁶ , R ⁹ , R ¹⁰ , R ¹¹ , R ¹² , R ¹³ , R ¹⁴ , R ¹⁵ , R ¹⁶ , R, respectively, in the general formula (1). ^{It is synonymous with 17} , R ¹⁸ , R ¹⁹ and R ²⁰ , and the preferred range is also the same.
^{R 3} and R ⁸ in the general formula (2) independently represent a hydrogen atom or an alkyl group, and preferably represent an alkyl group. As the alkyl group, an alkyl group having 1 to 6 carbon atoms is preferable, an alkyl group having 1 to 3 carbon atoms is more preferable, and a methyl group or an ethyl group is further preferable. Further, the alkyl group may have a substituent, and examples of the substituent include a substituent selected from the above-mentioned Substituent Group A.
^{It is preferable that R 401} , R ⁴⁰² , R ⁴⁰³ , R ⁴⁰⁴ and R ⁴⁰⁵ in the general formula (2) satisfy the above condition (i-1). That is, ^{it is preferable that at least one of R 401} , R ⁴⁰² , R ⁴⁰³ , R ⁴⁰⁴ and R ⁴⁰⁵ represents a hydroxyl group, and at least one represents a carboxyl group. ^{The preferred ranges of R 401} , R ⁴⁰² , R ⁴⁰³ , R ⁴⁰⁴ and R ⁴⁰⁵ are the same as R ⁴⁰¹ , R ⁴⁰² , R ⁴⁰³ , R ⁴⁰⁴ and R ^{405 in} the general formula (X1), respectively.
^{It is preferable that R 406} , R ⁴⁰⁷ , R ⁴⁰⁸ , R ⁴⁰⁹ and R ⁴¹⁰ in the general formula (2) satisfy the above condition (i-2). That is, ^{it is preferable that at least one of R 406} , R ⁴⁰⁷ , R ⁴⁰⁸ , R ⁴⁰⁹ and R ⁴¹⁰ represents a hydroxyl group, and at least one represents a carboxyl group. The preferable ranges of R ⁴⁰⁶ , R ⁴⁰⁷ , R ⁴⁰⁸ , R ⁴⁰⁹ and R ⁴¹⁰ are the same as those of R ⁴⁰¹ , R ⁴⁰² , R ⁴⁰³ , R ⁴⁰⁴ and R ^{405 in the} general formula (2), respectively.

^{R 1} , R ⁴ , R ⁵ , R ⁶ , R ⁹ , R ¹⁰ , R ¹¹ , R ¹² , R ¹³ , R ¹⁴ , R ¹⁵ , R ¹⁶ , R ¹⁷ , R ¹⁸ , R in the general formula (3) ¹⁹ and R ^{20 are R 1} , R ⁴ , R ⁵ , R ⁶ , R ⁹ , R ¹⁰ , R ¹¹ , R ¹² , R ¹³ , R ¹⁴ , R ¹⁵ , R ¹⁶ , R, respectively, in the general formula (1). ^{It is synonymous with 17} , R ¹⁸ , R ¹⁹ and R ²⁰ , and the preferred range is also the same.
^{R 3} and R ⁸ in the general formula (3) independently represent a hydrogen atom or an alkyl group, and preferably represent an alkyl group. As the alkyl group, an alkyl group having 1 to 6 carbon atoms is preferable, an alkyl group having 1 to 3 carbon atoms is more preferable, and a methyl group or an ethyl group is further preferable. Further, the alkyl group may have a substituent, and examples of the substituent include a substituent selected from the above-mentioned Substituent Group A.
^{It is preferable that R 501} , R ⁵⁰² , R ⁵⁰³ , R ⁵⁰⁴ , R ⁵⁰⁵ , R ⁵⁰⁶ and R ⁵⁰⁷ in the general formula (3) satisfy the above condition (iii-1). That is, ^{it is preferable that at least one of R 501} , R ⁵⁰² , R ⁵⁰³ , R ⁵⁰⁴ , R ⁵⁰⁵ , R ⁵⁰⁶ and R ⁵⁰⁷ represents a hydroxyl group, and at least one represents a carboxyl group. ^{R 501, R 502, R 503} , R 504, R 505, R 506 and preferred ranges of ^{R 507} may, ^R 501 each in the general formula ^{(X2), R 502, R} 503, R 504, R 505, R 506 And R ⁵⁰⁷ .
^{It is preferable that R 508} , R ⁵⁰⁹ , R ⁵¹⁰ , R ⁵¹¹ , R ⁵¹² , R ⁵¹³ and R ⁵¹⁴ in the general formula (3) satisfy the above condition (iii-2). That is, ^{it is preferable that at least one of R 508} , R ⁵⁰⁹ , R ⁵¹⁰ , R ⁵¹¹ , R ⁵¹² , R ⁵¹³ and R ⁵¹⁴ represents a hydroxyl group and at least one represents a carboxyl group. The preferred ranges of R ⁵⁰⁸ , R ⁵⁰⁹ , R ⁵¹⁰ , R ⁵¹¹ , R ⁵¹² , R ⁵¹³ and R ^{514 are R 501} , R ⁵⁰² , R ⁵⁰³ , R ⁵⁰⁴ , R ⁵⁰⁵ , R ^{506 in the} general formula (3), respectively. And R ⁵⁰⁷ .

^{R 1} , R ⁴ , R ⁵ , R ⁶ , R ⁹ , R ¹⁰ , R ¹¹ , R ¹² , R ¹³ , R ¹⁴ , R ¹⁵ , R ¹⁶ , R ¹⁷ , R ¹⁸ , R in the general formula (4) ¹⁹ and R ^{20 are R 1} , R ⁴ , R ⁵ , R ⁶ , R ⁹ , R ¹⁰ , R ¹¹ , R ¹² , R ¹³ , R ¹⁴ , R ¹⁵ , R ¹⁶ , R, respectively, in the general formula (1). ^{It is synonymous with 17} , R ¹⁸ , R ¹⁹ and R ²⁰ , and the preferred range is also the same.
^{R 3} and R ⁸ in the general formula (4) independently represent a hydrogen atom or an alkyl group, and preferably represent an alkyl group. As the alkyl group, an alkyl group having 1 to 6 carbon atoms is preferable, an alkyl group having 1 to 3 carbon atoms is more preferable, and a methyl group or an ethyl group is further preferable. Further, the alkyl group may have a substituent, and examples of the substituent include a substituent selected from the above-mentioned Substituent Group A.
^{It is preferable that R 601} , R ⁶⁰² , R ⁶⁰³ , R ⁶⁰⁴ , R ⁶⁰⁵ , R ⁶⁰⁶ and R ⁶⁰⁷ in the general formula (4) satisfy the above condition (v-1). That is, ^{it is preferable that at least one of R 601} and R ⁶⁰² , R ⁶⁰³ , R ⁶⁰⁴ , R ⁶⁰⁵ , R ⁶⁰⁶ and R ⁶⁰⁷ represents a hydroxyl group, and at least one represents a carboxyl group. ^{R 601, R 602, R 603} , R 604, R 605, R 606 and preferred ranges of ^{R 607} may, ^R 601 each in the general formula ^{(X3), R 602, R} 603, R 604, R 605, R 606 And R ⁶⁰⁷ .
^{It is preferable that R 608} , R ⁶⁰⁹ , R ⁶¹⁰ , R ⁶¹¹ , R ⁶¹² , R ⁶¹³ and R ⁶¹⁴ in the general formula (4) satisfy the above condition (v-2). That is, ^{it is preferable that at least one of R 608} , R ⁶⁰⁹ , R ⁶¹⁰ , R ⁶¹¹ , R ⁶¹² , R ⁶¹³ and R ⁶¹⁴ represents a hydroxyl group and at least one represents a carboxyl group. The preferred ranges of R ⁶⁰⁸ , R ⁶⁰⁹ , R ⁶¹⁰ , R ⁶¹¹ , R ⁶¹² , R ⁶¹³ and R ^{614 are R 601} , R ⁶⁰² , R ⁶⁰³ , R ⁶⁰⁴ , R ⁶⁰⁵ , R ^{606 in the} general formula (4), respectively. And R ⁶⁰⁷ .

Specific examples of the compound represented by the general formula (1) are given below, but the present invention is not limited thereto. In the structural formula of the specific compound below, Me represents a methyl group and Et represents an ethyl group.

A specific method for synthesizing the compound represented by the general formula (1) will be illustrated in Examples.

[Compound represented by the general formula (D)]
Next, the compound represented by the following general formula (D) will be described.

In the general formula (D), Y ₁ and Y ₂ each independently represent a hydrogen atom or a substituent. Z _{1 to} Z ₅ independently represent a hydrogen atom or a substituent. M ₁ and M ₂ independently represent a hydrogen atom, an ammonium ion, an alkali metal ion or an organic cation, respectively.

In the general formula (D), Y ₁ is preferably a substituted group, it is more preferable that an alkyl group or an aryl group, more preferably an aryl group. The alkyl group or the aryl group may have a substituent, and examples of the substituent include a substituent selected from the above-mentioned Substituent Group A.
When Y ₁ represents an aryl group having a substituent, the substituent is preferably a hydroxyl group, an ionic hydrophilic group, or an alkyl group. In particular _{, it is most preferable that Y 1} is a p-tolyl group from the viewpoint of availability of raw materials.

In the general formula (D), Y ₂ preferably represents a hydrogen atom, an alkyl group or an aryl group. Among them, a hydrogen atom, a methyl group or a phenyl group is preferable, and a hydrogen atom is most preferable from the viewpoint of availability of raw materials and dye production.

In the general formula (D), _{it is preferable that at least one of Z 1 to} Z ₅ represents a substituent, and it is more preferable that at least two represent a substituent. In particular, _{it is preferable that at least two of Z 1 to} Z ₅ represent two or more kinds of substituents different from each other. Examples of the substituent include a substituent selected from the above-mentioned Substituent Group A, which may be a substituent selected from a halogen atom, an alkyl group, an aryl group, an alcohol group, an aryloxy group, and an ionic hydrophilic group. It is more preferable that the substituent is selected from a halogen atom, an alcohol group, an aryloxy group, and an ionic hydrophilic group, and among them, a substituent selected from a halogen atom, an aryloxy group, and an ionic hydrophilic group. Is preferable. The alkyl group, the aryl group, the alkoxy group, and the aryloxy group may further have a substituent, and examples of the further substituent include a substituent selected from the above-mentioned Substituent Group A.

In the general formula (D), M ₁ and M ₂ independently represent a hydrogen atom, an ammonium ion, an alkali metal ion or an organic cation, preferably a hydrogen atom, an ammonium ion or an alkali metal ion, respectively, and represent a hydrogen atom or an alkali. It is more preferable to represent a metal ion.
The alkali metal ion is preferable from the viewpoint of water solubility, and as the alkali metal ion, potassium ion, sodium ion or lithium ion is preferable, lithium ion or sodium ion is more preferable, and sodium ion is most preferable from the viewpoint of cost and solubility. ..
Examples of the organic cation include tetramethylammonium ion, tetramethylguanidium ion, tetramethylphosphonium and the like.

From the viewpoint of water solubility, the compound represented by the general formula (D) preferably has 2 or more and 8 or less ionic hydrophilic groups (preferably carboxyl groups or sulfo groups) in its molecule. It is more preferable to have one or more and four or less.

The compound represented by the general formula (D) is preferably a compound represented by the following general formula (D2).

In the general formula (D2), Z _{1 to} Z ₅ and Z _{11 to} Z ₁₅ each independently represent a hydrogen atom or a substituent. M ₁ and M ₂ independently represent a hydrogen atom, an ammonium ion, an alkali metal ion or an organic cation, respectively.

In the general formula (D2), _{examples of the substituent when Z 11 to} Z ₁₅ represent a substituent include a substituent selected from the above-mentioned Substituent Group A.
Z _{11 to} Z ₁₅ preferably represent a hydrogen atom, an alkyl group, an aryl group, a sulfamoyl group, a hydroxyl group, or an ionic hydrophilic group, and represent a hydrogen atom, an alkyl group, a hydroxyl group, or an ionic hydrophilic group. More preferably, at least one selected from a hydrogen atom, an alkyl group and an ionic hydrophilic group is particularly preferable.

_{Z 1 ~Z} 5, _M 1 and _{M 2} in the general formula (D2) of the general formula (D) in the same meaning as _{Z 1 ~Z} 5, _M 1 and _{M 2} of the preferred range is also the same.

Further, the compound represented by the general formula (D) may be a compound represented by the following general formula (D3).

In the general formula (D3), Y ₂ and Y ₁₂ each independently represent a hydrogen atom or a substituent. Z _{1 to} Z ₅ and Z _{21 to} Z ₂₅ independently represent a hydrogen atom or a substituent. M ₁ , M ₂ , M ₁₁ and M ₁₂ independently represent a hydrogen atom, an ammonium ion, an alkali metal ion or an organic cation, respectively. L represents a divalent linking group.

L in the general formula (D3) preferably represents an alkylene group or an arylene group, and more preferably represents an arylene group. The alkylene group or the arylene group may have a substituent, and examples of the substituent include a substituent selected from the above-mentioned Substituent Group A.
_{Y 2, Z 1 ~Z 5,} M 1 and _{M 2} in the general formula (D3) is, _Y 2 in the general formula _{(D), Z 1 ~Z 5} , have the same meaning as _{M 1} and _{M 2,} preferably The range is the same.
_{Y 12} in the general formula (D3) _{has the same meaning as Y 2} in the general formula (D), and the preferable range is also the same.
_{Z 21 to} Z ₂₅ in the general formula (D3) _{are synonymous with Z 1 to} Z ₅ in the general formula (D), and the preferable range is also the same.
_{M 11} and M ₁₂ in the general formula (D3) _{are synonymous with M 1} and M ₂ in the general formula (D), and the preferable range is also the same.

Specific examples of the compound represented by the general formula (D) are shown below, but the present invention is not limited to the following examples. In the specific examples below, -SO ₃ M ₁ , -SO ₃ M ₂ , -SO ₃ M ₁₁ , -SO ₃ M ₁₂ , -CO ₂ M ₃ to _{-CO 2} M ₅ are free acids (-SO ₃ H), it may be in the state of _(-CO 2 H), salt ^{_{(-SO 3 - M +),}} (- CO 2 - M +) or in the form of. M ⁺ represents an ammonium ion, an alkali metal ion or an organic cation.

[Coloring composition]
The coloring composition of the present invention contains the compound represented by the general formula (1) and the compound represented by the general formula (D).
The compound represented by the above general formula (1) contained in the coloring composition of the present invention may be one kind or two or more kinds. Further, the compound represented by the above general formula (D) contained in the coloring composition of the present invention may be one kind or two or more kinds.

The coloring composition of the present invention can further contain a medium, but is particularly suitable as an ink for inkjet recording when a solvent is used as the medium. The coloring composition of the present invention uses a lipophilic medium or an aqueous medium as a medium, and the compound represented by the general formula (1) and the compound represented by the general formula (D) are contained therein. It can be made by dissolving and / or dispersing. Preferably, an aqueous medium is used. The coloring composition of the present invention also includes a composition for ink excluding the medium.

The content of the compound represented by the general formula (1) contained in the coloring composition is the type of the compound represented by the general formula (1) used and the solvent component used for producing the coloring composition. _{The content (W 1} ) of the compound represented by the general formula (1) in the coloring composition is 1.0 to 20% by mass with respect to the total amount of the coloring composition. Is more preferable, and it is more preferably 2.0 to 10% by mass, further preferably 2.0 to 5% by mass, particularly preferably 2.0 to 4.0% by mass, and 2.0. Most preferably, it is at least by mass% and less than 3.5% by mass.

The content of the compound represented by the general formula contained in the coloring composition _(D) (W D) is preferably 0.1 to 3.0 wt% based on the total weight of the coloring composition, It is more preferably 0.1 to 2.5% by mass, further preferably 0.1 to 2.0% by mass, and most preferably 0.1% by mass or more and less than 1.5% by mass. ..

The total content of the compound represented by the general formula (1) and the compound represented by the general formula (D) contained in the coloring composition is 5.0% by mass with respect to the total amount of the coloring composition. It is preferably less than or equal to, more preferably 1.5 to 5.0% by mass, further preferably 1.5 to 4.5% by mass, and 1.5 to 4.0% by mass. It is particularly preferable, it is extremely preferably 1.5 to 3.5% by mass, and most preferably 2.0 to 3.5% by mass.

When printed by setting the total content of the compound represented by the general formula (1) and the compound represented by the general formula (D) contained in the coloring composition to 1.5% by mass or more. The printing density of the ink on the recording medium can be improved. Further, by setting the total content of the compound represented by the general formula (1) and the compound represented by the above general formula (D) contained in the coloring composition to 3.5% by mass or less, inkjet recording can be performed. When used in the method, the ejection property of the coloring composition can be improved, and the effect that the inkjet nozzle is less likely to be clogged can be obtained.

The content of the compound represented by the general formula (1) and _{(W 1),} the content of the compound represented by the general formula (D) _{(W D)} and the mass ratio of _(W 1 / _{W D)} the hue , chroma, coloring power (printing density), light resistance, ozone resistance, and in view of moisture resistance _balance, W 1 / _{W D} is 99 / 1-50 / 50, 99 / 1-60 / 40 It is more preferably 99/1 to 70/30, particularly preferably 95/5 to 80/20, and even more preferably 95/5 to 85/15. Most preferably, it is / 5 to 90/10.

The coloring composition of the present invention is a coloring material other than the compound represented by the general formula (1) and the compound represented by the general formula (D) (that is, a coloring material other than the compound represented by the general formula (1)). However, a coloring material other than the compound represented by the general formula (D)) may be further contained.

If necessary, the coloring composition of the present invention may contain other additives within the range in which the effects of the present invention are exhibited. The coloring composition of the present invention is suitably used as an ink for inkjet recording.

[Ink for inkjet recording]
The ink for inkjet recording of the present invention contains the coloring composition of the present invention.
The ink for inkjet recording of the present invention may be the coloring composition of the present invention.
The ink for inkjet recording can be produced by dissolving and / or dispersing the compound represented by the general formula (1) and the compound represented by the general formula (D) in a lipophilic medium or an aqueous medium. The ink for inkjet recording is preferably an ink using an aqueous medium.
If necessary, the ink for inkjet recording may contain other additives within the range in which the effects of the present invention are exhibited. Other additives include, for example, anti-drying agents (wetting agents), anti-fading agents, emulsion stabilizers, penetration promoters, UV absorbers, preservatives, fungicides, pH regulators, surface tension regulators, defoamers. Known additives such as foaming agents, viscosity regulators, dispersants, dispersion stabilizers, rust preventives, chelating agents, betaine compounds and the like can be mentioned. In the case of water-soluble ink, these various additives can be added directly to the ink liquid. When the oil-soluble dye is used in the form of a dispersion, it is generally added to the dispersion after preparation of the dye dispersion, but it may be added to the oil phase or the aqueous phase at the time of preparation.
The content of the compound represented by the general formula (1), the content of the compound represented by the general formula (D), the content of the compound represented by the general formula (1) and the general formula ( The preferable range of the mass ratio with the content of the compound represented by D) is the same as that described above.

The anti-drying agent is preferably used for the purpose of preventing clogging due to drying of the ink for inkjet recording at the ink injection port of the nozzle used in the inkjet recording method.

As the anti-drying agent, a water-soluble organic solvent having a lower vapor pressure than water is preferable. Specific examples include ethylene glycol, propylene glycol, diethylene glycol, polyethylene glycol, thiodiglycol, dithiodiglycol, 2-methyl-1,3-propanediol, 1,2,6-hexanetriol, acetylene glycol derivative, and glycerin. , Polyhydric alcohols typified by trimethylolpropane, etc., lower alkyl ethers of polyhydric alcohols such as ethylene glycol monomethyl (or ethyl) ether, diethylene glycol monomethyl (or ethyl) ether, triethylene glycol monoethyl (or butyl) ether, etc. , 2-Pyrrolidone, N-methyl-2-pyrrolidone, 1,3-dimethyl-2-imidazolidinone, N-ethylmorpholin and other heterocyclics, sulfolane, dimethylsulfoxide, 3-sulfolene and other sulfur-containing compounds, Examples thereof include polyfunctional compounds such as diacetone alcohol and diethanolamine, and urea derivatives. Of these, polyhydric alcohols such as glycerin and diethylene glycol are more preferable. Further, the above-mentioned anti-drying agent may be used alone or in combination of two or more. These anti-drying agents are preferably contained in the ink in an amount of 10 to 50% by mass.

The penetration accelerator can be used for the purpose of allowing the ink for inkjet recording to penetrate the paper better. As the permeation accelerator, alcohols such as ethanol, isopropanol, butanol, di (tri) ethylene glycol monobutyl ether and 1,2-hexanediol, sodium lauryl sulfate, sodium oleate, nonionic surfactant and the like can be used. .. If these are contained in the ink in an amount of 5 to 30% by mass, they usually have a sufficient effect, and it is preferable to use them in an amount of addition that does not cause print bleeding or paper omission (print through).

The ultraviolet absorber can be used for the purpose of improving the storage stability of the image. Examples of the ultraviolet absorber include benzotriazoles described in JP-A-58-185677, JP-A-61-190537, JP-A-2-782, JP-A-5-97075, JP-A-9-34057 and the like. Compounds, Benzophenone-based compounds described in JP-A-46-2784, JP-A-5-194843, US Pat. No. 3,214,463, etc. Triazole compounds described in JP-A-10-88106, etc., JP-A-4-298503, JP-A-8-53427, JP-A-8-239368, JP-A-10-182621, JP-A-8. Triazine-based compounds described in JP-A-501291, etc., Research Disclosure No. A compound described in No. 24239, a compound that absorbs ultraviolet rays and emits fluorescence, such as a stilbene-based compound and a benzoxazole-based compound, a so-called fluorescent whitening agent can also be used.

Anti-fading agents are used for the purpose of improving the storage stability of images. As the anti-fading agent, various organic and metal complex-based anti-fading agents can be used. Organic anti-fading agents include hydroquinones, alkoxyphenols, dialkoxyphenols, phenols, anilines, amines, indans, chromans, alkoxyanilines, heterocycles, etc., and nickel as a metal complex. There are complexes, zinc complexes, etc. More specifically, Research Disclosure No. 17643, No. I to J of VII, No. 15162, No. 18716, page 650, left column, No. No. 527 of 36544, the same No. 307105, p. 872, No. Compounds described in the patent cited in 15162 and compounds included in the general formulas and compound examples of representative compounds described on pages 127 to 137 of JP-A-62-215272A can be used.

Examples of the fungicide include sodium dehydroacetate, sodium benzoate, sodium pyridinethioone-1-oxide, p-hydroxybenzoic acid ethyl ester, 1,2-benzisothiazolin-3-one and salts thereof. These are preferably used in an ink in an amount of 0.02 to 1.00% by mass.

As the pH adjuster, a neutralizing agent (organic base, inorganic alkali) can be used. The pH adjuster is preferably added so that the pH of the inkjet recording ink becomes 6 to 10, and more preferably 7 to 10 for the purpose of improving the storage stability of the inkjet recording ink.

Examples of the surface tension adjusting agent include nonionic, cationic or anionic surfactants. The surface tension of the ink for inkjet recording of the present invention is preferably 25 to 70 mN / m. Further, 25 to 60 mN / m is preferable. The viscosity of the ink for inkjet recording of the present invention is preferably 30 mPa · s or less. Further, it is more preferable to adjust to 20 mPa · s or less. Examples of surfactants are fatty acid salts, alkyl sulfates, alkylbenzene sulfonates, alkylnaphthalene sulfonates, dialkyl sulfosuccinates, alkyl phosphates, naphthalene sulfonic acid formalin condensates, polyoxyethylene alkyl sulfates. Anionic surfactants such as ester salts, polyoxyethylene alkyl ether, polyoxyethylene alkyl allyl ether, polyoxyethylene fatty acid ester, sorbitan fatty acid ester, polyoxyethylene sorbitan fatty acid ester, polyoxyethylene alkylamine, glycerin fatty acid ester , Oxyethylene oxypropylene block copolymer and other nonionic surfactants are preferable. Further, SURFYNOLS (AirProducts & Chemicals), which is an acetylene-based polyoxyethylene oxide surfactant, is also preferably used. In addition, amine oxide type amphoteric surfactants such as N, N-dimethyl-N-alkylamine oxide are also preferable. Further, Japanese Patent Application Laid-Open No. 59-157,636, pp. (37) to (38), Research Disclosure No. Those listed as surfactants described in 308119 (1989) can also be used.

As the defoaming agent, a fluorine-based compound, a silicone-based compound, a chelating agent typified by EDTA (ethylenediaminetetraacetic acid), or the like can also be used, if necessary.

Betaine compounds can be used for the purpose of preventing image bleeding under high humidity conditions. As the betaine compound, those listed in JP-A-2004-285269 and the like can be preferably used. The preferable range of the amount of these betaine compounds added varies depending on the type, but it is preferable to use 0.01 to 10.0% by mass, preferably 0.01 to 5.0% by mass in the ink for inkjet recording. It is more preferable, and it is most preferable to use 0.01 to 3.0% by mass.

As the betaine compound that can be used in the present invention, a compound represented by the following general formula (W-2) is particularly preferable.

In the general formula (W-2), Ra to Rc each independently represent a hydrogen atom, an alkyl group, an aryl group, or a heterocyclic group. However, at least one of Ra to Rc contains an alkyl group having 8 or more carbon atoms. L ₁ represents a divalent linking group.

In the general formula (W-2), at least one of Ra to Rc is preferably an alkyl group having 8 or more carbon atoms, more preferably an alkyl group having 8 or more carbon atoms and 18 or less carbon atoms, and has 12 or more carbon atoms and 16 carbon atoms. The following alkyl groups are more preferred.

Specific examples of the compound represented by the general formula (W-2) are shown below, but the present invention is not limited to the following examples.

As the aqueous medium, a mixture containing water as a main component and optionally adding a water-miscible organic solvent can be used. Examples of water-miscible organic solvents include alcohols (eg, methanol, ethanol, propanol, isopropanol, butanol, isobutanol, sec-butanol, t-butanol, pentanol, hexanol, cyclohexanol, benzyl alcohol), polyhydric alcohols. Classes (eg, ethylene glycol, diethylene glycol, triethylene glycol, polyethylene glycol, propylene glycol, dipropylene glycol, polypropylene glycol, butylene glycol, hexanediol, pentanediol, glycerin, hexanetriol, thiodiglycol), glycol derivatives (eg, Ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol monobutyl ether, propylene glycol monomethyl ether, propylene glycol monobutyl ether, dipropylene glycol monomethyl ether, triethylene glycol monomethyl ether, ethylene glycol Diacetate, ethylene glycol monomethyl ether acetate, triethylene glycol monomethyl ether, triethylene glycol monoethyl ether, ethylene glycol monophenyl ether), amines (eg ethanolamine, diethanolamine, triethanolamine, N-methyldiethanolamine, N-ethyl) Diethanolamine, morpholine, N-ethylmorpholine, ethylenediamine, diethylenetriamine, triethylenetetramine, polyethyleneimine, tetramethylpropylenediamine) and other polar solvents (eg, formamide, N, N-dimethylformamide, N, N-dimethylacetamide, dimethyl). Sulfoxide, sulfolane, 2-pyrrolidone, N-methyl-2-pyrrolidone, N-vinyl-2-pyrrolidone, 2-oxazolidone, 1,3-dimethyl-2-imidazolidinone, acetonitrile, acetone) are included. Two or more kinds of water-miscible organic solvents may be used in combination.

The ink for inkjet 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 can be determined by various additives such as viscosity modifiers, surface tension modifiers, specific resistance modifiers, film modifiers, UV absorbers, antioxidants, fading inhibitors, fungicides, rust inhibitors. , Dispersants and surfactants can be added.

Although the ink for inkjet recording of the present invention can be used as an ink having various color tones, it is preferably used as a magenta color tone ink. Further, it can be used not only for monochromatic image formation but also for full-color image formation. Magenta tones, cyan tones, and yellow tones can be used to form full-color images, and black tones may be further used to adjust the tones.

The ink for inkjet recording of the present invention can be used for recording methods such as printing, copying, marking, writing, drafting, and stamping, and is particularly suitable for use in an inkjet recording method.

[Inkjet recording method]
The inkjet recording method of the present invention supplies energy to the inkjet recording ink of the present invention to provide known image-receiving materials, that is, plain paper, resin-coated paper, for example, JP-A-8-169172 and No. 8-27693. , 2-276670, 7-276789, 9-323475, 62-238783, 10-153989, 10-217473, 10-235995. Images on inkjet paper, film, electrophotographic paper, cloth, glass, metal, ceramics, etc. described in No. 10, No. 10-33747, No. 10-217597, No. 10-337947, etc. To form.

When forming an image, a polymer fine particle dispersion (also referred to as polymer latex) may be used in combination for the purpose of imparting glossiness and water resistance or improving weather resistance. The time when the polymer latex is applied to the image receiving material may be before, after, or at the same time as the colorant is applied, and therefore the place of addition may be in the image receiving paper. It may be used in ink or as a liquid substance of polymer latex alone. Specifically, Japanese Patent Application No. 2000-363090, 2000-315231, 2000-354380, 2000-343944, 2000-268952, 2000-299465, 2000-297365, etc. The method described in the specification can be preferably used.

[Inkjet printer cartridge and inkjet recorded material]
The inkjet printer cartridge of the present invention is filled with the above-mentioned ink for inkjet recording of the present invention. Further, the inkjet recorded material is obtained by forming a colored image on the material to be recorded by using the above-mentioned ink for inkjet recording of the present invention.

The inkjet recording ink of the present invention is not limited to the inkjet recording method, and is a known method, for example, a charge control method for ejecting ink by using electrostatic attraction, and a drop-on-demand method using the vibration pressure of a piezo element. Method (pressure pulse method), acoustic inkjet method that converts an electric signal into an acoustic beam and irradiates the ink to eject the ink using the radiation pressure, and heats the ink to form bubbles and uses the generated pressure. It is used for thermal inkjet methods and the like. For the inkjet recording method, a method of ejecting a large number of low-density inks called photo inks in a small volume, a method of improving image quality by using a plurality of inks having substantially the same hue but different densities, and a colorless and transparent ink are used. The method is included.

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 "part" in the example are mass% and parts by mass.

(Synthesis example)
(Synthesis of Exemplified Compound (1-11))
Exemplified compound (1-11) can be synthesized, for example, according to the following scheme.

(Synthesis of intermediate (B))
23.0 g of Intermediate (A) (synthesized by the method described in paragraph 17 of Japanese Patent Application Laid-Open No. 2011-148973) was added to 420 g of 10% fuming sulfuric acid and reacted at room temperature for 48 hours. .. The reaction solution was poured into a large excess of ethyl acetate, and the precipitated crystals were filtered off. The filtered crystals were dissolved in 500 mL of methanol, adjusted to pH 7 with a 28% sodium methoxide methanol solution, and the precipitated sodium sulfate was removed by filtration. The filtrate is concentrated using a rotary evaporator, and the obtained residue is purified by column chromatography (filler: Sephadex LH-20 (manufactured by Pharmacia), developing solvent: methanol) to obtain crystals of the intermediate (B). It was. Yield 21.0 g, yield 68%, mass spectrum (MS) (m / z) = 793 ([M-2Na + H] ⁻ , 100%).

(Synthesis of Exemplified Compound (1-11))
3.0 g of Intermediate (B) was dissolved in 15 mL of ultrapure water, and the internal temperature was cooled to 10 ° C. or lower. Add 2.55 g of 5-chlorosulfonylsalicylic acid (synthesized by the method described in German Patent DE264786) as a powder, and adjust the pH of the reaction solution to 8.0 using a 10% NaOH aqueous solution while keeping the internal temperature at 10 ° C or lower. It was maintained and the dropping was continued until there was no change in pH. The obtained reaction solution was poured into a large excess of isopropyl alcohol, and the precipitated solid was filtered off. The obtained solid is dissolved in 20 mL of a mixed solvent of water / methanol: 1/1, purified by column chromatography (filler: Sephadex LH-20 (manufactured by Pharmacia), developing solvent: water / methanol), and then a dialysis membrane. Inorganic salts and residual organic solvents were removed using (fractional molecular weight 3500, Spectra / Por3 Dialysis Membrane (trade name, manufactured by Spectrum = Laboratory Co., Ltd.)). The pH of the obtained aqueous solution was adjusted to 7 with a dilute sodium hydroxide aqueous solution, dust removal and filtration were performed with a membrane filter, and the obtained aqueous solution was concentrated to dryness with a rotary evaporator to bring the green color of the example compound (1-11). Glossy crystals were obtained. Yield 1.5 g, yield 33%. MS (m / z) = 1191 ([M-1] ⁻ , 100%). The absorption maximum wavelength of the absorption spectrum of the exemplified compound (1-11) in a dilute aqueous solution was 532 nm, and the molar extinction coefficient was 87,000. ^{The 1} H-NMR spectrum of the exemplary compound (1-11) in dimethyl sulfoxide-d6 is shown in FIG.

(Synthesis of Exemplified Compound (1-18))
Exemplified compound (1-18) can be synthesized, for example, according to the following scheme.

3.0 g of the intermediate (B) obtained as a synthetic intermediate of the above-mentioned exemplified compound (1-11) was dissolved in 15 mL of ultrapure water, and the internal temperature was cooled to 10 ° C. or lower. Add 2.2 g of 5-chlorosulfonyl-3-hydroxy-2-naphthoic acid (synthesized by the method described in German Patent DE264786) as a powder, and react with a 10% NaOH aqueous solution at an internal temperature of 10 ° C. or lower. The pH of the solution was maintained at 7.5, and dropping was continued until there was no change in pH. The obtained reaction solution was poured into a large excess of isopropyl alcohol, and the precipitated solid was filtered off. The obtained solid is dissolved in 20 mL of a mixed solvent of water / methanol: 1/1, purified by column chromatography (filler: Sephadex LH-20 (manufactured by Pharmacia), developing solvent: water / methanol), and then a dialysis membrane. Inorganic salts and residual organic solvents were removed using (fractional molecular weight 3500, Spectra / Por3 Dialysis Membrane (trade name, manufactured by Spectrum = Laboratory Co., Ltd.)). The pH of the obtained aqueous solution was adjusted to 7 with a dilute sodium hydroxide aqueous solution, dust removal and filtration were performed with a membrane filter, and the obtained aqueous solution was concentrated to dryness with a rotary evaporator to bring the green color of the example compound (1-18). Glossy crystals were obtained. Yield 1.2 g, yield 24%. MS (m / z) = 1291 ([M-1] ⁻ , 100%). The absorption maximum wavelength of the absorption spectrum of the exemplified compound (1-18) in a dilute aqueous solution was 532 nm, and the molar extinction coefficient was 85,000. ^{The 1} H-NMR spectrum of the example compound (1-18) in dimethyl sulfoxide-d6 is shown in FIG.

(Synthesis of Exemplified Compound (1-25))
Exemplified compound (1-25) can be synthesized, for example, according to the following scheme.

3.0 g of the intermediate (B) obtained as a synthetic intermediate of the above-mentioned exemplified compound (1-11) was dissolved in 15 mL of ultrapure water, and the internal temperature was cooled to 10 ° C. or lower. Add 2.2 g of 6-chlorosulfonyl-2-hydroxy-1-naphthoic acid (synthesized by the method described in German Patent DE278901) as a powder, and react with a 10% NaOH aqueous solution at an internal temperature of 10 ° C. or lower. The pH of the solution was maintained at 7.5, and dropping was continued until there was no change in pH. The obtained reaction solution was poured into a large excess of isopropyl alcohol, and the precipitated solid was filtered off. The obtained solid is dissolved in 20 mL of a mixed solvent of water / methanol: 1/1, purified by column chromatography (filler: Sephadex LH-20 (manufactured by Pharmacia), developing solvent: water / methanol), and then a dialysis membrane. Inorganic salts and residual organic solvents were removed using (fractional molecular weight 3500, Spectra / Por3 Dialysis Membrane (trade name, manufactured by Spectrum = Laboratory Co., Ltd.)). The pH of the obtained aqueous solution was adjusted to 7 with a dilute sodium hydroxide aqueous solution, dust removal and filtration were performed with a membrane filter, and the obtained aqueous solution was concentrated to dryness with a rotary evaporator to bring the green color of the example compound (1-25). Glossy crystals were obtained. Yield 1.3 g, yield 26%. MS (m / z) = 1291 ([M-1] ⁻ , 100%). The absorption maximum wavelength of the absorption spectrum of the exemplified compound (1-25) in a dilute aqueous solution was 532 nm, and the molar extinction coefficient was 83000.

(Synthesis of Exemplified Compound (1-26))
Exemplified compound (1-26) can be synthesized, for example, according to the following scheme.

3.0 g of the intermediate (B) obtained as a synthetic intermediate of the above-mentioned exemplified compound (1-11) was dissolved in 15 mL of ultrapure water, and the internal temperature was cooled to 10 ° C. or lower. Add 2.7 g of 5-chlorosulfonyl-4-hydroxyisophthalic acid (synthesized by the method described in German Patent DE264786) as a powder, keep the internal temperature at 10 ° C. or lower, and use a 10% NaOH aqueous solution to pH the reaction solution. Was kept at 7.5, and dropping was continued until there was no change in pH. The obtained reaction solution was poured into a large excess of isopropyl alcohol, and the precipitated solid was filtered off. The obtained solid is dissolved in 20 mL of a mixed solvent of water / methanol: 1/1, purified by column chromatography (filler: Sephadex LH-20 (manufactured by Pharmacia), developing solvent: water / methanol), and then a dialysis membrane. Inorganic salts and residual organic solvents were removed using (fractional molecular weight 3500, Spectra / Por3 Dialysis Membrane (trade name, manufactured by Spectrum = Laboratory Co., Ltd.)). The pH of the obtained aqueous solution was adjusted to 7 with a dilute sodium hydroxide aqueous solution, dust removal and filtration were performed with a membrane filter, and the obtained aqueous solution was concentrated to dryness with a rotary evaporator to bring the green color of the example compound (1-26). Glossy crystals were obtained. Yield 1.8 g, yield 36%. MS (m / z) = 1279 ([M-1] ⁻ , 100%). The absorption maximum wavelength of the absorption spectrum of the exemplified compound (1-26) in a dilute aqueous solution was 534 nm, and the molar extinction coefficient was 95,000. ^{The 1} H-NMR spectrum of the example compound (1-26) in dimethyl sulfoxide-d6 is shown in FIG.

(Synthesis of Exemplified Compound (1-30))
Exemplified compound (1-30) can be synthesized, for example, according to the following scheme.

3.0 g of the intermediate (B) obtained as a synthetic intermediate of the above-mentioned exemplified compound (1-11) was dissolved in 15 mL of ultrapure water. Add 2.2 g of dimethyl 5-chlorosulfonyl-terephthalate (synthesized by the method described in German Patent DE278901) as a powder, keep the pH of the reaction solution at 5 to 7 using a 10% NaOH aqueous solution, and change the pH. The dropping was continued until there was no more. After completion of the reaction, 3 mL of a 50% aqueous NaOH solution was subsequently added, and the mixture was stirred for 1 hour. The obtained reaction solution was poured into a large excess of ethanol, and the precipitated solid was filtered off. The obtained solid is dissolved in 20 mL of a mixed solvent of water / methanol: 1/1, purified by column chromatography (filler: Sephadex LH-20 (manufactured by Pharmacia), developing solvent: water / methanol), and then a dialysis membrane. Inorganic salts and residual organic solvents were removed using (fractional molecular weight 3500, Spectra / Por3 Dialysis Membrane (trade name, manufactured by Spectrum = Laboratory Co., Ltd.)). The pH of the obtained aqueous solution was adjusted to 7 with a dilute sodium hydroxide aqueous solution, dust removal and filtration were performed with a membrane filter, and the obtained aqueous solution was concentrated to dryness with a rotary evaporator to bring the green color of the example compound (1-30). Glossy crystals were obtained. Yield 3.7 g, yield 70%. MS (m / z) = 1247 ([M-1] ⁻ , 100%). The absorption maximum wavelength of the absorption spectrum of the exemplified compound (1-30) in a dilute aqueous solution was 532 nm, and the molar extinction coefficient was 82000. ^{The 1} H-NMR spectrum of the example compound (1-30) in dimethyl sulfoxide-d6 is shown in FIG.

Other exemplary compounds can also be synthesized according to the above method.

When the exemplified compounds (d-1) to (d-5) are used in the following Examples and Comparative Examples, they are represented by the above-mentioned structural formulas, and M _{1 to} M ₅ , M ₁₁ and M ₁₂ are all represented. A compound that is a sodium ion was used.

[Example 1]
After adding deionized water to the following components to make 100 g, the mixture was stirred for 1 hour while heating at 30-40 ° C. Then, the pH was adjusted to 8.5 with a 10 mol / L aqueous sodium hydroxide solution, and the ink was filtered under reduced pressure with a microfilter having an average pore size of 0.20 μm to prepare an ink 1 for inkjet recording for magenta.
Compound of general formula (1) (exemplified compound (1-11)) 2.25 g
Compound of general formula (D) (exemplified compound (d-3)) 0.25 g
Proxel XLII (preservative, manufactured by LONZA Co., Ltd.) 0.11 g
Glycerin 10.00g
Triethylene glycol 2.00g
Triethylene glycol monobutyl ether 10.00g
2-Pyrrolidone 2.00 g
Surfinol (manufactured by Air Products & Chemicals)
1.00g

[Example 2]
After adding deionized water to the following components to make 100 g, the mixture was stirred for 1 hour while heating at 30-40 ° C. Then, the pH was adjusted to 8.5 with a 10 mol / L aqueous sodium hydroxide solution, and the ink was filtered under reduced pressure with a microfilter having an average pore size of 0.20 μm to prepare an ink for inkjet recording 2 for magenta.
Compound of general formula (1) (exemplified compound (1-11)) 2.25 g
Compound of general formula (D) (exemplified compound (d-3)) 0.25 g
Proxel XLII (preservative, manufactured by LONZA Co., Ltd.) 0.11 g
Betaine-1 (betaine compound having the following structure) 1.28 g
Glycerin 10.00g
Triethylene glycol 2.00g
Triethylene glycol monobutyl ether 10.00g
2-Pyrrolidone 2.00 g
Surfinol (manufactured by Air Products & Chemicals)
1.00g

[Example 3]
After adding deionized water to the following components to make 100 g, the mixture was stirred for 1 hour while heating at 30-40 ° C. Then, the pH was adjusted to 8.5 with a 10 mol / L sodium hydroxide aqueous solution, and the ink was filtered under reduced pressure with a microfilter having an average pore size of 0.20 μm to prepare an inkjet recording ink 3 for magenta.
Compound of general formula (1) (exemplified compound (1-11)) 2.25 g
Compound of general formula (D) (exemplified compound (d-3)) 0.25 g
Proxel XLII (preservative, manufactured by LONZA Co., Ltd.) 0.11 g
Betaine-2 (betaine compound having the following structure) 1.28 g
Glycerin 10.00g
Triethylene glycol 2.00g
Triethylene glycol monobutyl ether 10.00g
2-Pyrrolidone 2.00 g
Surfinol (manufactured by Air Products & Chemicals)
1.00g

[Example 4]
After adding deionized water to the following components to make 100 g, the mixture was stirred for 1 hour while heating at 30-40 ° C. Then, the pH was adjusted to 8.5 with a 10 mol / L sodium hydroxide aqueous solution, and the ink was filtered under reduced pressure with a microfilter having an average pore size of 0.20 μm to prepare an inkjet recording ink 4 for magenta.
Compound of general formula (1) (exemplified compound (1-11)) 2.00 g
Compound of general formula (D) (exemplified compound (d-3)) 0.50 g
Proxel XLII (preservative, manufactured by LONZA Co., Ltd.) 0.11 g
Betaine-1 1.14g
Glycerin 10.00g
Triethylene glycol 2.00g
Triethylene glycol monobutyl ether 10.00g
2-Pyrrolidone 2.00 g
Surfinol (manufactured by Air Products & Chemicals)
1.00g

[Example 5]
After adding deionized water to the following components to make 100 g, the mixture was stirred for 1 hour while heating at 30-40 ° C. Then, the pH was adjusted to 8.5 with a 10 mol / L sodium hydroxide aqueous solution, and the ink was filtered under reduced pressure with a microfilter having an average pore size of 0.20 μm to prepare an inkjet recording ink 5 for magenta.
Compound of general formula (1) (exemplified compound (1-11)) 1.75 g
Compound of general formula (D) (exemplified compound (d-3)) 0.75 g
Proxel XLII (preservative, manufactured by LONZA Co., Ltd.) 0.11 g
Betaine-1 1.00g
Glycerin 10.00g
Triethylene glycol 2.00g
Triethylene glycol monobutyl ether 10.00g
2-Pyrrolidone 2.00 g
Surfinol (manufactured by Air Products & Chemicals)
1.00g

[Example 6]
An inkjet recording ink 6 was prepared by the same operation as in Example 2 except that the example compound (1-18) was used instead of the example compound (1-11).

[Example 7]
An inkjet recording ink 7 was prepared by the same operation as in Example 2 except that the example compound (1-19) was used instead of the example compound (1-11).

[Example 8]
An inkjet recording ink 8 was prepared by the same operation as in Example 2 except that the example compound (1-20) was used instead of the example compound (1-11).

[Example 9]
An inkjet recording ink 9 was prepared by the same operation as in Example 2 except that the example compound (1-25) was used instead of the example compound (1-11).

[Example 10]
An inkjet recording ink 10 was prepared by the same operation as in Example 1 except that the exemplary compound (1-26) was used instead of the exemplary compound (1-11).

[Example 11]
An inkjet recording ink 11 was prepared by the same operation as in Example 2 except that the example compound (1-26) was used instead of the example compound (1-11).

[Example 12]
An inkjet recording ink 12 was prepared by the same operation as in Example 2 except that the exemplary compound (1-29) was used instead of the exemplary compound (1-11).

[Example 13]
An inkjet recording ink 13 was prepared by the same operation as in Example 2 except that the exemplified compound (1-30) was used instead of the illustrated compound (1-11).

[Example 14]
An inkjet recording ink 14 was prepared by the same operation as in Example 3 except that the example compound (1-30) was used instead of the example compound (1-11).

[Example 15]
An inkjet recording ink 15 was prepared by the same operation as in Example 2 except that the exemplary compound (1-34) was used instead of the exemplary compound (1-11).

[Example 16]
An inkjet recording ink 16 was prepared by the same operation as in Example 1 except that the exemplary compound (1-35) was used instead of the exemplary compound (1-11).

[Example 17]
An inkjet recording ink 17 was prepared by the same operation as in Example 2 except that the example compound (1-35) was used instead of the example compound (1-11).

[Example 18]
An inkjet recording ink 18 was prepared by the same operation as in Example 1 except that the example compound (d-1) was used instead of the example compound (d-3).

[Example 19]
An inkjet recording ink 19 was prepared by the same operation as in Example 2 except that the exemplary compound (d-1) was used instead of the exemplary compound (d-3).

[Example 20]
An inkjet recording ink 20 was prepared by the same operation as in Example 2 except that the exemplified compound (d-2) was used instead of the illustrated compound (d-3).

[Example 21]
An inkjet recording ink 21 was prepared by the same operation as in Example 2 except that the exemplified compound (d-4) was used instead of the illustrated compound (d-3).

[Example 22]
An inkjet recording ink 22 was prepared by the same operation as in Example 2 except that the exemplary compound (d-5) was used instead of the exemplary compound (d-3).

[Example 23]
After adding deionized water to the following components to make 100 g, the mixture was stirred for 1 hour while heating at 30-40 ° C. Then, the pH was adjusted to 8.5 with a 10 mol / L aqueous sodium hydroxide solution, and the ink was filtered under reduced pressure with a microfilter having an average pore size of 0.20 μm to prepare an ink for inkjet recording 23 for magenta.
Compound of general formula (1) (exemplified compound (1-30)) 2.25 g
Compound of general formula (D) (exemplified compound (d-3)) 0.25 g
Proxel XLII (preservative, manufactured by LONZA Co., Ltd.) 0.11 g
Betaine-3 (betaine compound having the following structure) 1.28 g
Glycerin 10.00g
Triethylene glycol 2.00g
Triethylene glycol monobutyl ether 10.00g
2-Pyrrolidone 2.00 g
Surfinol (manufactured by Air Products & Chemicals)
1.00g

[Example 24]
After adding deionized water to the following components to make 100 g, the mixture was stirred for 1 hour while heating at 30-40 ° C. Then, the pH was adjusted to 8.5 with a 10 mol / L sodium hydroxide aqueous solution, and the ink was filtered under reduced pressure with a microfilter having an average pore size of 0.20 μm to prepare an inkjet recording ink 24 for magenta.
Compound of general formula (1) (exemplified compound (1-30)) 2.25 g
Compound of general formula (D) (exemplified compound (d-3)) 0.25 g
Proxel XLII (preservative, manufactured by LONZA Co., Ltd.) 0.11 g
Betaine-4 (betaine compound having the following structure) 1.28 g
Glycerin 10.00g
Triethylene glycol 2.00g
Triethylene glycol monobutyl ether 10.00g
2-Pyrrolidone 2.00 g
Surfinol (manufactured by Air Products & Chemicals)
1.00g

[Example 25]
After adding deionized water to the following components to make 100 g, the mixture was stirred for 1 hour while heating at 30-40 ° C. Then, the pH was adjusted to 8.5 with a 10 mol / L aqueous sodium hydroxide solution, and the ink was filtered under reduced pressure with a microfilter having an average pore size of 0.20 μm to prepare an ink 25 for inkjet recording for magenta.
Compound of general formula (1) (exemplified compound (1-30)) 2.25 g
Compound of general formula (D) (exemplified compound (d-3)) 0.25 g
Proxel XLII (preservative, manufactured by LONZA Co., Ltd.) 0.11 g
Betaine-5 (betaine compound with the following structure) 1.28 g
Glycerin 10.00g
Triethylene glycol 2.00g
Triethylene glycol monobutyl ether 10.00g
2-Pyrrolidone 2.00 g
Surfinol (manufactured by Air Products & Chemicals)
1.00g

[Example 26]
After adding deionized water to the following components to make 100 g, the mixture was stirred for 1 hour while heating at 30-40 ° C. Then, the pH was adjusted to 8.5 with a 10 mol / L aqueous sodium hydroxide solution, and the ink was filtered under reduced pressure with a microfilter having an average pore size of 0.20 μm to prepare an ink for inkjet recording 26 for magenta.
Compound of general formula (1) (exemplified compound (1-30)) 2.25 g
Compound of general formula (D) (exemplified compound (d-3)) 0.25 g
Proxel XLII (preservative, manufactured by LONZA Co., Ltd.) 0.11 g
Betaine-6 (betaine compound with the following structure) 1.28 g
Glycerin 10.00g
Triethylene glycol 2.00g
Triethylene glycol monobutyl ether 10.00g
2-Pyrrolidone 2.00 g
Surfinol (manufactured by Air Products & Chemicals)
1.00g

[Example 27]
After adding deionized water to the following components to make 100 g, the mixture was stirred for 1 hour while heating at 30-40 ° C. Then, the pH was adjusted to 8.5 with a 10 mol / L aqueous sodium hydroxide solution, and the mixture was filtered under reduced pressure with a microfilter having an average pore size of 0.20 μm to prepare an inkjet recording ink 27 for magenta.
Compound of general formula (1) (exemplified compound (1-26)) 2.25 g
Compound of general formula (D) (exemplified compound (d-3)) 0.25 g
Proxel XLII (preservative, manufactured by LONZA Co., Ltd.) 0.11 g
Glycerin 7.00g
Ethylene urea 7.00g
1,5-pentanediol 7.00g
2-Pyrrolidone 5.00g
Surfinol (manufactured by Air Products & Chemicals)
0.50g

[Example 28]
After adding deionized water to the following components to make 100 g, the mixture was stirred for 1 hour while heating at 30-40 ° C. Then, the pH was adjusted to 8.5 with a 10 mol / L aqueous sodium hydroxide solution, and the ink was filtered under reduced pressure with a microfilter having an average pore size of 0.20 μm to prepare an ink for inkjet recording 28 for magenta.
Compound of general formula (1) (exemplified compound (1-30)) 2.25 g
Compound of general formula (D) (exemplified compound (d-3)) 0.25 g
Proxel XLII (preservative, manufactured by LONZA Co., Ltd.) 0.11 g
Glycerin 7.00g
Ethylene urea 7.00g
1,5-pentanediol 7.00g
2-Pyrrolidone 5.00g
Surfinol (manufactured by Air Products & Chemicals)
0.50g

[Example 29]
After adding deionized water to the following components to make 100 g, the mixture was stirred for 1 hour while heating at 30-40 ° C. Then, the pH was adjusted to 8.5 with a 10 mol / L aqueous sodium hydroxide solution, and the ink was filtered under reduced pressure with a microfilter having an average pore size of 0.20 μm to prepare an ink for inkjet recording 29 for magenta.
Compound of general formula (1) (exemplified compound (1-30)) 2.38 g
Compound of general formula (D) (exemplified compound (d-3)) 0.12 g
Proxel XLII (preservative, manufactured by LONZA Co., Ltd.) 0.11 g
Glycerin 7.00g
Ethylene urea 7.00g
1,5-pentanediol 7.00g
2-Pyrrolidone 5.00g
Surfinol (manufactured by Air Products & Chemicals)
0.50g

[Example 30]
After adding deionized water to the following components to make 100 g, the mixture was stirred for 1 hour while heating at 30-40 ° C. Then, the pH was adjusted to 8.5 with a 10 mol / L sodium hydroxide aqueous solution, and the ink was filtered under reduced pressure with a microfilter having an average pore size of 0.20 μm to prepare an inkjet recording ink 30 for magenta.
Compound of general formula (1) (exemplified compound (1-30)) 2.00 g
Compound of general formula (D) (exemplified compound (d-3)) 0.50 g
Proxel XLII (preservative, manufactured by LONZA Co., Ltd.) 0.11 g
Glycerin 7.00g
Ethylene urea 7.00g
1,5-pentanediol 7.00g
2-Pyrrolidone 5.00g
Surfinol (manufactured by Air Products & Chemicals)
0.50g

[Example 31]
After adding deionized water to the following components to make 100 g, the mixture was stirred for 1 hour while heating at 30-40 ° C. Then, the pH was adjusted to 8.5 with a 10 mol / L sodium hydroxide aqueous solution, and the ink was filtered under reduced pressure with a microfilter having an average pore size of 0.20 μm to prepare an inkjet recording ink 31 for magenta.
Compound of general formula (1) (exemplified compound (1-30)) 1.75 g
Compound of general formula (D) (exemplified compound (d-3)) 0.75 g
Proxel XLII (preservative, manufactured by LONZA Co., Ltd.) 0.11 g
Glycerin 7.00g
Ethylene urea 7.00g
1,5-pentanediol 7.00g
2-Pyrrolidone 5.00g
Surfinol (manufactured by Air Products & Chemicals)
0.50g

[Example 32]
After adding deionized water to the following components to make 100 g, the mixture was stirred for 1 hour while heating at 30-40 ° C. Then, the pH was adjusted to 8.5 with a 10 mol / L sodium hydroxide aqueous solution, and the ink was filtered under reduced pressure with a microfilter having an average pore size of 0.20 μm to prepare an inkjet recording ink 32 for magenta.
Compound of general formula (1) (exemplified compound (1-30)) 1.50 g
Compound of general formula (D) (exemplified compound (d-3)) 1.00 g
Proxel XLII (preservative, manufactured by LONZA Co., Ltd.) 0.11 g
Glycerin 7.00g
Ethylene urea 7.00g
1,5-pentanediol 7.00g
2-Pyrrolidone 5.00g
Surfinol (manufactured by Air Products & Chemicals)
0.50g

[Example 33]
After adding deionized water to the following components to make 100 g, the mixture was stirred for 1 hour while heating at 30-40 ° C. Then, the pH was adjusted to 8.5 with a 10 mol / L aqueous sodium hydroxide solution, and the ink was filtered under reduced pressure with a microfilter having an average pore size of 0.20 μm to prepare an ink for inkjet recording 33 for magenta.
Compound of general formula (1) (exemplified compound (1-30)) 1.25 g
Compound of general formula (D) (exemplified compound (d-3)) 1.25 g
Proxel XLII (preservative, manufactured by LONZA Co., Ltd.) 0.11 g
Glycerin 7.00g
Ethylene urea 7.00g
1,5-pentanediol 7.00g
2-Pyrrolidone 5.00g
Surfinol (manufactured by Air Products & Chemicals)
0.50g

[Example 34]
After adding deionized water to the following components to make 100 g, the mixture was stirred for 1 hour while heating at 30-40 ° C. Then, the pH was adjusted to 8.5 with a 10 mol / L aqueous sodium hydroxide solution, and the ink was filtered under reduced pressure with a microfilter having an average pore size of 0.20 μm to prepare an ink for inkjet recording 34 for magenta.
Compound of general formula (1) (exemplified compound (1-30)) 5.00 g
Compound of general formula (D) (exemplified compound (d-3)) 0.50 g
Proxel XLII (preservative, manufactured by LONZA Co., Ltd.) 0.11 g
Glycerin 7.00g
Ethylene urea 7.00g
1,5-pentanediol 7.00g
2-Pyrrolidone 5.00g
Surfinol (manufactured by Air Products & Chemicals)
0.50g

[Example 35]
After adding deionized water to the following components to make 100 g, the mixture was stirred for 1 hour while heating at 30-40 ° C. Then, the pH was adjusted to 8.5 with a 10 mol / L aqueous sodium hydroxide solution, and the ink was filtered under reduced pressure with a microfilter having an average pore size of 0.20 μm to prepare an ink 35 for inkjet recording for magenta.
Compound of general formula (1) (exemplified compound (1-30)) 4.50 g
Compound of general formula (D) (exemplified compound (d-3)) 0.50 g
Proxel XLII (preservative, manufactured by LONZA Co., Ltd.) 0.11 g
Glycerin 7.00g
Ethylene urea 7.00g
1,5-pentanediol 7.00g
2-Pyrrolidone 5.00g
Surfinol (manufactured by Air Products & Chemicals)
0.50g

[Example 36]
After adding deionized water to the following components to make 100 g, the mixture was stirred for 1 hour while heating at 30-40 ° C. Then, the pH was adjusted to 8.5 with a 10 mol / L aqueous sodium hydroxide solution, and the ink was filtered under reduced pressure with a microfilter having an average pore size of 0.20 μm to prepare an ink for inkjet recording 36 for magenta.
Compound of general formula (1) (exemplified compound (1-30)) 3.60 g
Compound of general formula (D) (exemplified compound (d-3)) 0.40 g
Proxel XLII (preservative, manufactured by LONZA Co., Ltd.) 0.11 g
Glycerin 7.00g
Ethylene urea 7.00g
1,5-pentanediol 7.00g
2-Pyrrolidone 5.00g
Surfinol (manufactured by Air Products & Chemicals)
0.50g

[Example 37]
After adding deionized water to the following components to make 100 g, the mixture was stirred for 1 hour while heating at 30-40 ° C. Then, the pH was adjusted to 8.5 with a 10 mol / L aqueous sodium hydroxide solution, and the ink was filtered under reduced pressure with a microfilter having an average pore size of 0.20 μm to prepare an ink for inkjet recording 37 for magenta.
Compound of general formula (1) (exemplified compound (1-30)) 2.70 g
Compound of general formula (D) (exemplified compound (d-3)) 0.30 g
Proxel XLII (preservative, manufactured by LONZA Co., Ltd.) 0.11 g
Glycerin 7.00g
Ethylene urea 7.00g
1,5-pentanediol 7.00g
2-Pyrrolidone 5.00g
Surfinol (manufactured by Air Products & Chemicals)
0.50g

[Example 38]
After adding deionized water to the following components to make 100 g, the mixture was stirred for 1 hour while heating at 30-40 ° C. Then, the pH was adjusted to 8.5 with a 10 mol / L sodium hydroxide aqueous solution, and the ink was filtered under reduced pressure with a microfilter having an average pore size of 0.20 μm to prepare an inkjet recording ink 38 for magenta.
Compound of general formula (1) (exemplified compound (1-30)) 1.80 g
Compound of general formula (D) (exemplified compound (d-3)) 0.20 g
Proxel XLII (preservative, manufactured by LONZA Co., Ltd.) 0.11 g
Glycerin 7.00g
Ethylene urea 7.00g
1,5-pentanediol 7.00g
2-Pyrrolidone 5.00g
Surfinol (manufactured by Air Products & Chemicals)
0.50g

[Example 39]
After adding deionized water to the following components to make 100 g, the mixture was stirred for 1 hour while heating at 30-40 ° C. Then, the pH was adjusted to 8.5 with a 10 mol / L aqueous sodium hydroxide solution, and the ink was filtered under reduced pressure with a microfilter having an average pore size of 0.20 μm to prepare an ink for inkjet recording 39 for magenta.
Compound of general formula (1) (exemplified compound (1-30)) 1.35 g
Compound of general formula (D) (exemplified compound (d-3)) 0.15 g
Proxel XLII (preservative, manufactured by LONZA Co., Ltd.) 0.11 g
Glycerin 7.00g
Ethylene urea 7.00g
1,5-pentanediol 7.00g
2-Pyrrolidone 5.00g
Surfinol (manufactured by Air Products & Chemicals)
0.50g

[Example 40]
After adding deionized water to the following components to make 100 g, the mixture was stirred for 1 hour while heating at 30-40 ° C. Then, the pH was adjusted to 8.5 with a 10 mol / L aqueous sodium hydroxide solution, and the ink was filtered under reduced pressure with a microfilter having an average pore size of 0.20 μm to prepare an ink for inkjet recording 40 for magenta.
Compound of general formula (1) (exemplified compound (1-26)) 2.00 g
Compound of general formula (D) (exemplified compound (d-3)) 0.25 g
Compound X 0.25 g of the following structural formula
Proxel XLII (preservative, manufactured by LONZA Co., Ltd.) 0.11 g
Glycerin 7.00g
Ethylene urea 7.00g
1,5-pentanediol 7.00g
2-Pyrrolidone 5.00g
Surfinol (manufactured by Air Products & Chemicals)
0.50g

[Comparative Example 1]
After adding deionized water to the following components to make 100 g, the mixture was stirred for 1 hour while heating at 30-40 ° C. Then, the pH was adjusted to 8.5 with a 10 mol / L sodium hydroxide aqueous solution, and the ink was filtered under reduced pressure with a microfilter having an average pore size of 0.20 μm to prepare a comparative inkjet recording ink 1 for magenta.
Compound of general formula (D) (exemplified compound (d-3)) 2.50 g
Proxel XLII (preservative, manufactured by LONZA Co., Ltd.) 0.11 g
Glycerin 10.00g
Triethylene glycol 2.00g
Triethylene glycol monobutyl ether 10.00g
2-Pyrrolidone 2.00 g
Surfinol (manufactured by Air Products & Chemicals)
1.00g

[Comparative Example 2]
After adding deionized water to the following components to make 100 g, the mixture was stirred for 1 hour while heating at 30-40 ° C. Then, the pH was adjusted to 8.5 with a 10 mol / L sodium hydroxide aqueous solution, and the ink was filtered under reduced pressure with a microfilter having an average pore size of 0.20 μm to prepare a comparative inkjet recording ink 2 for magenta.
Compound of general formula (D) (exemplified compound (d-3)) 2.50 g
Proxel XLII (preservative, manufactured by LONZA Co., Ltd.) 0.11 g
Betaine-1 1.43g
Glycerin 10.00g
Triethylene glycol 2.00g
Triethylene glycol monobutyl ether 10.00g
2-Pyrrolidone 2.00 g
Surfinol (manufactured by Air Products & Chemicals)
1.00g

[Comparative Example 3]
After adding deionized water to the following components to make 100 g, the mixture was stirred for 1 hour while heating at 30-40 ° C. Then, the pH was adjusted to 8.5 with a 10 mol / L aqueous sodium hydroxide solution, and the ink was filtered under reduced pressure with a microfilter having an average pore size of 0.20 μm to prepare a comparative inkjet recording ink 3 for magenta.
Compound of general formula (1) (exemplified compound (1-11)) 1.00 g
Proxel XLII (preservative, manufactured by LONZA Co., Ltd.) 0.11 g
Glycerin 10.00g
Triethylene glycol 2.00g
Triethylene glycol monobutyl ether 10.00g
2-Pyrrolidone 2.00 g
Surfinol (manufactured by Air Products & Chemicals)
1.00g

[Comparative Example 4]
After adding deionized water to the following components to make 100 g, the mixture was stirred for 1 hour while heating at 30-40 ° C. Then, the pH was adjusted to 8.5 with a 10 mol / L sodium hydroxide aqueous solution, and the ink was filtered under reduced pressure with a microfilter having an average pore size of 0.20 μm to prepare a comparative inkjet recording ink 4 for magenta.
Compound of general formula (1) (exemplified compound (1-11)) 0.50 g
Compound of general formula (D) (exemplified compound (d-1)) 2.00 g
Proxel XLII (preservative, manufactured by LONZA Co., Ltd.) 0.11 g
Glycerin 10.00g
Triethylene glycol 2.00g
Triethylene glycol monobutyl ether 10.00g
2-Pyrrolidone 2.00 g
Surfinol (manufactured by Air Products & Chemicals)
1.00g

[Comparative Example 5]
After adding deionized water to the following components to make 100 g, the mixture was stirred for 1 hour while heating at 30-40 ° C. Then, the pH was adjusted to 8.5 with a 10 mol / L aqueous sodium hydroxide solution, and the ink was filtered under reduced pressure with a microfilter having an average pore size of 0.20 μm to prepare a comparative inkjet recording ink 5 for magenta.
Compound of general formula (1) (exemplified compound (1-11)) 0.50 g
Compound of general formula (D) (exemplified compound (d-3)) 2.00 g
Proxel XLII (preservative, manufactured by LONZA Co., Ltd.) 0.11 g
Glycerin 10.00g
Triethylene glycol 2.00g
Triethylene glycol monobutyl ether 10.00g
2-Pyrrolidone 2.00 g
Surfinol (manufactured by Air Products & Chemicals)
1.00g

[Comparative Example 6]
After adding deionized water to the following components to make 100 g, the mixture was stirred for 1 hour while heating at 30-40 ° C. Then, the pH was adjusted to 8.5 with a 10 mol / L sodium hydroxide aqueous solution, and the ink was filtered under reduced pressure with a microfilter having an average pore size of 0.20 μm to prepare a comparative inkjet recording ink 6 for magenta.
Compound of general formula (1) (exemplified compound (1-11)) 0.50 g
Compound of general formula (D) (exemplified compound (d-5)) 2.00 g
Proxel XLII (preservative, manufactured by LONZA Co., Ltd.) 0.11 g
Glycerin 10.00g
Triethylene glycol 2.00g
Triethylene glycol monobutyl ether 10.00g
2-Pyrrolidone 2.00 g
Surfinol (manufactured by Air Products & Chemicals)
1.00g

[Comparative Example 7]
After adding deionized water to the following components to make 100 g, the mixture was stirred for 1 hour while heating at 30-40 ° C. Then, the pH was adjusted to 8.5 with a 10 mol / L sodium hydroxide aqueous solution, and the ink was filtered under reduced pressure with a microfilter having an average pore size of 0.20 μm to prepare a comparative inkjet recording ink 7 for magenta.
Comparative compound 12.00 g
Compound of general formula (D) (exemplified compound (d-3)) 0.50 g
Proxel XLII (preservative, manufactured by LONZA Co., Ltd.) 0.11 g
Glycerin 10.00g
Triethylene glycol 2.00g
Triethylene glycol monobutyl ether 10.00g
2-Pyrrolidone 2.00 g
Surfinol (manufactured by Air Products & Chemicals)
1.00g

[Comparative Example 8]
After adding deionized water to the following components to make 100 g, the mixture was stirred for 1 hour while heating at 30-40 ° C. Then, the pH was adjusted to 8.5 with a 10 mol / L aqueous sodium hydroxide solution, and the ink was filtered under reduced pressure with a microfilter having an average pore size of 0.20 μm to prepare a comparative inkjet recording ink 8 for magenta.
Comparative compound 22.00 g
Compound of general formula (D) (exemplified compound (d-3)) 0.50 g
Proxel XLII (preservative, manufactured by LONZA Co., Ltd.) 0.11 g
Glycerin 10.00g
Triethylene glycol 2.00g
Triethylene glycol monobutyl ether 10.00g
2-Pyrrolidone 2.00 g
Surfinol (manufactured by Air Products & Chemicals)
1.00g

[Comparative Example 9]
After adding deionized water to the following components to make 100 g, the mixture was stirred for 1 hour while heating at 30-40 ° C. Then, the pH was adjusted to 8.5 with a 10 mol / L sodium hydroxide aqueous solution, and the ink was filtered under reduced pressure with a microfilter having an average pore size of 0.20 μm to prepare a comparative inkjet recording ink 9 for magenta.
Comparative compound 3 2.00 g
Compound of general formula (D) (exemplified compound (d-3)) 0.50 g
Proxel XLII (preservative, manufactured by LONZA Co., Ltd.) 0.11 g
Glycerin 10.00g
Triethylene glycol 2.00g
Triethylene glycol monobutyl ether 10.00g
2-Pyrrolidone 2.00 g
Surfinol (manufactured by Air Products & Chemicals)
1.00g

[Comparative Example 10]
After adding deionized water to the following components to make 100 g, the mixture was stirred for 1 hour while heating at 30-40 ° C. Then, the pH was adjusted to 8.5 with a 10 mol / L sodium hydroxide aqueous solution, and the ink was filtered under reduced pressure with a microfilter having an average pore size of 0.20 μm to prepare a comparative inkjet recording ink 10 for magenta.
Comparative compound 4 2.00 g
Compound of general formula (D) (exemplified compound (d-3)) 0.50 g
Proxel XLII (preservative, manufactured by LONZA Co., Ltd.) 0.11 g
Glycerin 10.00g
Triethylene glycol 2.00g
Triethylene glycol monobutyl ether 10.00g
2-Pyrrolidone 2.00 g
Surfinol (manufactured by Air Products & Chemicals)
1.00g

[Comparative Example 11]
After adding deionized water to the following components to make 100 g, the mixture was stirred for 1 hour while heating at 30-40 ° C. Then, the pH was adjusted to 8.5 with a 10 mol / L aqueous sodium hydroxide solution, and the ink was filtered under reduced pressure with a microfilter having an average pore size of 0.20 μm to prepare a comparative inkjet recording ink 11 for magenta.
Compound of general formula (D) (exemplified compound (d-3)) 2.50 g
Proxel XLII (preservative, manufactured by LONZA Co., Ltd.) 0.11 g
Glycerin 7.00g
Ethylene urea 7.00g
1,5-pentanediol 7.00g
2-Pyrrolidone 5.00g
Surfinol (manufactured by Air Products & Chemicals)
0.50g

[Comparative Example 12]
After adding deionized water to the following components to make 100 g, the mixture was stirred for 1 hour while heating at 30-40 ° C. Then, the pH was adjusted to 8.5 with a 10 mol / L aqueous sodium hydroxide solution, and the ink was filtered under reduced pressure with a microfilter having an average pore size of 0.20 μm to prepare a comparative inkjet recording ink 12 for magenta.
Comparative compound 1 0.25 g
Compound of general formula (D) (exemplified compound (d-3)) 2.25 g
Proxel XLII (preservative, manufactured by LONZA Co., Ltd.) 0.11 g
Glycerin 7.00g
Ethylene urea 7.00g
1,5-pentanediol 7.00g
2-Pyrrolidone 5.00g
Surfinol (manufactured by Air Products & Chemicals)
0.50g

[Comparative Example 13]
After adding deionized water to the following components to make 100 g, the mixture was stirred for 1 hour while heating at 30-40 ° C. Then, the pH was adjusted to 8.5 with a 10 mol / L aqueous sodium hydroxide solution, and the ink was filtered under reduced pressure with a microfilter having an average pore size of 0.20 μm to prepare a comparative inkjet recording ink 13 for magenta.
Comparative compound 2 2.25 g
Compound of general formula (D) (exemplified compound (d-3)) 0.25 g
Proxel XLII (preservative, manufactured by LONZA Co., Ltd.) 0.11 g
Glycerin 7.00g
Ethylene urea 7.00g
1,5-pentanediol 7.00g
2-Pyrrolidone 5.00g
Surfinol (manufactured by Air Products & Chemicals)
0.50g

[Comparative Example 14]
After adding deionized water to the following components to make 100 g, the mixture was stirred for 1 hour while heating at 30-40 ° C. Then, the pH was adjusted to 8.5 with a 10 mol / L aqueous sodium hydroxide solution, and the ink was filtered under reduced pressure with a microfilter having an average pore size of 0.20 μm to prepare a comparative inkjet recording ink 14 for magenta.
Comparative compound 3 2.25 g
Compound of general formula (D) (exemplified compound (d-3)) 0.25 g
Proxel XLII (preservative, manufactured by LONZA Co., Ltd.) 0.11 g
Glycerin 7.00g
Ethylene urea 7.00g
1,5-pentanediol 7.00g
2-Pyrrolidone 5.00g
Surfinol (manufactured by Air Products & Chemicals)
0.50g

[Comparative Example 15]
After adding deionized water to the following components to make 100 g, the mixture was stirred for 1 hour while heating at 30-40 ° C. Then, the pH was adjusted to 8.5 with a 10 mol / L aqueous sodium hydroxide solution, and the ink was filtered under reduced pressure with a microfilter having an average pore size of 0.20 μm to prepare a comparative inkjet recording ink 15 for magenta.
Comparative Compound 4 2.25 g
Compound of general formula (D) (exemplified compound (d-3)) 0.25 g
Proxel XLII (preservative, manufactured by LONZA Co., Ltd.) 0.11 g
Glycerin 7.00g
Ethylene urea 7.00g
1,5-pentanediol 7.00g
2-Pyrrolidone 5.00g
Surfinol (manufactured by Air Products & Chemicals)
0.50g

[Comparative Example 16]
After adding deionized water to the following components to make 100 g, the mixture was stirred for 1 hour while heating at 30-40 ° C. Then, the pH was adjusted to 8.5 with a 10 mol / L aqueous sodium hydroxide solution, and the ink was filtered under reduced pressure with a microfilter having an average pore size of 0.20 μm to prepare a comparative inkjet recording ink 16 for magenta.
Comparative compound 2 2.50 g
Proxel XLII (preservative, manufactured by LONZA Co., Ltd.) 0.11 g
Glycerin 7.00g
Ethylene urea 7.00g
1,5-pentanediol 7.00g
2-Pyrrolidone 5.00g
Surfinol (manufactured by Air Products & Chemicals)
0.50g

(Image recording and evaluation)
The following evaluations were performed on the inkjet recording inks 1 to 26 of Examples and the comparative inkjet recording inks 1 to 10 of Comparative Examples. The results are shown in Tables 1 to 3.
In Tables 1 to 3, each evaluation is performed by loading each ink for inkjet recording into an ink cartridge and using an inkjet printer (manufactured by Seiko Epson Corporation; PM-700C) as photo paper (photo paper manufactured by Seiko Epson Corporation). It was evaluated after recording the image in <gloss>).

The following evaluations were performed on the inkjet recording inks 27 to 40 of Examples and the comparative inkjet recording inks 11 to 16 of Comparative Examples. The results are shown in Tables 1 to 3. In Tables 1 to 3, each evaluation was performed by loading each ink for inkjet recording into an ink cartridge and using an inkjet printer (manufactured by Canon Inc .; PIXUS Pro9000MkII) for dedicated inkjet paper (manufactured by Canon Inc .; photo glossy paper). It was evaluated after recording an image on PT-202).

<Hue>
The printed sample was visually observed and evaluated on a three-point scale, with A being a pure-colored magenta, B being a magenta that was slightly reddish-red, and C being a clear magenta.

<Saturation>
The saturation (C ^* ) of the printed matter was calculated by the following formula based on the measurement of the color characteristics. For the printed image part at an applied voltage of 50%, use a reflection densitometer (trade name X-Rite 310TR, manufactured by Xrite), CIE L ^* a ^* b ^* color system (International Commission on Illumination Standard (1976)) or ^{Measure the brightness L *} and chromaticity a ^* and b ^* in JIS (Japanese Industrial Standards) Z8781-4: 2013) ^{, obtain the saturation (C *} ) from the obtained values based on the following formula, and evaluate. The results were evaluated according to the following criteria.

A: When C ^* is 90 or more B: When C ^* is 80 or more and less than 90 C: When C ^* is less than 80

<Print density>
For Examples 1 to 26 and Comparative Examples 1 to 10, an inkjet printer (manufactured by Seiko Epson Corporation) was used using the inkjet recording inks 1 to 26 of Examples and the comparative inkjet recording inks 1 to 10 of Comparative Examples, respectively. A solid-painted image (printed image at an applied voltage of 100%) was recorded on a photo paper (photo paper <glossy> manufactured by Seiko Epson Corporation) using PM-700C).
For Examples 27 to 40 and Comparative Examples 11 to 16, respectively, the inkjet recording inks 27 to 40 of the example and the comparative inkjet recording inks 11 to 16 of the comparative example were used, and an inkjet printer (manufactured by Canon Inc.; A solid-painted image (printed image at an applied voltage of 100%) was recorded on an inkjet paper (manufactured by Canon Inc .; photo glossy paper PT-202) with PIXUSPro9000MkII).
The print density of the created solid-painted image is measured using a reflection densitometer (trade name X-Rite310TR, manufactured by X-Rite), and when the print density is 2.0 or more, it is A, 1.8 or more and less than 2.0. The case of 1 was B, the case of 1.7 or more and less than 1.8 was C, and the case of less than 1.7 was D, and the evaluation was made on a four-point scale.

<Light resistance>
After measuring the image density Ci immediately after recording, the image was irradiated with xenon light (100,000 lux) for 28 days using a weather meter (Atlas C.165), and then the image density Cf1 was measured again to measure the xenon light. The dye residual rate was calculated and evaluated from the image density before and after irradiation. The image density was measured using a reflection densitometer (trade name: X-Rite 310TR, manufactured by Xrite). The dye residual ratio was measured using an image portion having an initial image density of 1.0 ± 0.2.
The dye residual ratio was calculated from the following formula, and the light resistance was evaluated according to the following criteria.
Dye residual rate (%) = (Cf1 / Ci) x 100

A: When the dye residual rate is 90% or more and less than 95% B: When the dye residual rate is 80% or more and less than 90% C: When the dye residual rate is less than 80%

<Ozone resistance>
A 5 kV AC voltage is applied while passing dry air through the double glass tube of the Siemens type ozonizer, and the ozone gas concentration is 5 ± 0.1 ppm, the room temperature (20 ° C.), and the inside of the box is set in a dark place. , The paper on which the image was formed was left for 3 days, the image density after being left under ozone gas was measured using a reflection densitometer (trade name X-Rite 310TR, manufactured by Xrite), and the initial image density Ci and leaving under ozone gas were measured. The dye residual rate was calculated and evaluated from the subsequent image density Cf2. The dye residual ratio was measured using an image portion having an initial image density of 1.0 ± 0.2. The ozone gas concentration in the box was set using an ozone gas monitor manufactured by APPLICS (model: OZG-EM-01).
The dye residual ratio was calculated from the following formula, and the ozone resistance was evaluated according to the following criteria.
Dye residual rate (%) = (Cf2 / Ci) x 100

A: When the dye residual rate is 85% or more and less than 90% B: When the dye residual rate is 80% or more and less than 85% C: When the dye residual rate is less than 80%

<Moisture resistance>
For image bleeding under high humidity conditions, a 3 cm x 3 cm print pattern was created by arranging magenta 1 mm x 1 mm squares so that a 0.5 mm white background gap was formed between the squares. After storing this image sample at 45 ° C. and a relative humidity of 80% for 7 days, bleeding of magenta dye in the gaps between white backgrounds was observed.
Specifically, the OD value of the printed matter before being exposed to the above conditions (45 ° C. and 80% relative humidity) (immediately after printing) and after being stored for 7 days under the above conditions is measured by a reflection densitometer (“Spectrilino””. Measured using (trade name: Gretag), the magenta concentration increase on a white background after storage for 7 days under the above conditions immediately after printing is less than 0.02 in the status A green filter, A, 0. The case of 0.02 or more and less than 0.05 was designated as B, the case of 0.05 or more and less than 0.10 was designated as C, and the case of 0.10 or more was designated as D.

<Discharge stability>
Regarding ejection stability, immediately after preparing each ink for inkjet recording, for an inkjet printer (trade name PM-700C, manufactured by Seiko Epson Corporation) (Examples 1 to 26, Comparative Examples 1 to 10), and an inkjet. After filling the ink cartridges for the printer (manufactured by Canon Corporation; PIXUSPro9000MkII) (Examples 27 to 40, Comparative Examples 11 to 16), setting the ink cartridges in the inkjet printer, and confirming the ink ejection from all the nozzles. , A4 size inkjet recording medium {photo paper <gloss> (trade name, manufactured by Seiko Epson Corporation)} (Examples 1 to 26, Comparative Examples 1 to 10) or inkjet paper (manufactured by Canon Corporation; Photo) Glossy paper PT-202) (Examples 27 to 40, Comparative Examples 11 to 16) When 100 sheets were output and evaluated according to the following criteria, the evaluation result was "A" in all Examples and Comparative Examples. there were.
Further, after storing each inkjet recording ink under the conditions of 40 ° C. and 80% relative humidity for 2 weeks, each inkjet recording ink is again used in an inkjet printer (trade name: product name PM-700C, manufactured by Seiko Epson Corporation). Ink cartridges for use (Examples 1 to 26, Comparative Examples 1 to 10) and for inkjet printers (manufactured by Canon Inc .; PIXUSPro9000MkII) (Examples 27 to 39, Comparative Examples 11 to 16) are filled with ink. After setting the cartridge in the inkjet printer and checking the ejection of ink from all the nozzles, A4 size inkjet recording medium {photo paper <gloss> (trade name, manufactured by Seiko Epson Corporation)} (Examples 1 to 26, Output was performed on 100 sheets of Comparative Examples 1 to 10) or an inkjet paper (manufactured by Canon Corporation; photo glossy paper PT-202) (Examples 27 to 40, Comparative Examples 11 to 16).
It was evaluated whether or not there was a difference between the ejection property of the inkjet recording ink immediately after the preparation and the ejection property of the inkjet recording ink after storage at 40 ° C. and a relative humidity of 80% for 2 weeks.
Differences were evaluated according to the following criteria, and the results are shown in Tables 1 to 3 below.
A: There is almost no print distortion from the start to the end of printing B: Output with print distortion occurs C: There is print distortion from the start to the end of printing

As is clear from the results in Tables 1 to 3, the inks for inkjet recording of the examples are excellent in hue, coloring power, light resistance, ozone resistance, moisture resistance, and ejection stability in an inkjet printer. It was.

According to the present invention, it is possible to form an image having excellent hue, saturation, coloring power (print density), and excellent light resistance, ozone resistance, and moisture resistance, and further, it is possible to improve ejection stability in an inkjet printer. It is also possible to provide an excellent coloring composition, an inkjet recording ink using the coloring composition, an inkjet recording method using the inkjet recording ink, and an inkjet printer cartridge filled with the inkjet recording ink.

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 February 3, 2017 (Japanese Patent Office 2017-019039) and a Japanese patent application filed on January 29, 2018 (Japanese Patent Office 2018-012895). It is taken here as a reference.

Claims (10)

A coloring composition containing a compound represented by the following general formula (1) and a compound represented by the following general formula (D).
When the content _{W 1} of the compound represented by the following general formula _{(1), W 1 / W} D 99/1 is the mass ratio of the content of _{W D} of the compound represented by the following general formula (D) A coloring composition of 50/50.

In the general formula (1), R ¹ , R ⁵ , R ⁶ and R ¹⁰ each independently represent an alkyl group. R ⁴ , R ⁹ , R ¹¹ , R ¹² , R ¹³ , R ¹⁴ , R ¹⁵ , R ¹⁶ , R ¹⁷ , R ¹⁸ , R ¹⁹ and R ²⁰ each independently represent a hydrogen atom or substituent. R ² , R ³ , R ⁷ and R ⁸ each independently represent a hydrogen atom, an alkyl group or a substituent represented by the following general formula (A), and at least of ^{R 2} , R ³ , R ⁷ and R ⁸ One represents a substituent represented by the following general formula (A).

In the general formula (A), X represents a substituent represented by the following general formula (X1), general formula (X2) or general formula (X3). * Represents a bond that binds to the benzene ring.

In the general formula (X1), R ⁴⁰¹ , R ⁴⁰² , R ⁴⁰³ , R ⁴⁰⁴ and R ⁴⁰⁵ each independently represent a hydrogen atom or a substituent. However, R ⁴⁰¹ , R ⁴⁰² , R ⁴⁰³ , R ⁴⁰⁴ and R ⁴⁰⁵ satisfy the following conditions (i) or (ii). * Represents a bond that binds to a sulfur atom.
Condition (i): At ^{least one of R 401} , R ⁴⁰² , R ⁴⁰³ , R ⁴⁰⁴ and R ⁴⁰⁵ represents a hydroxyl group, and at least one represents a carboxyl group.
Condition (ii): At ^{least two of R 401} , R ⁴⁰² , R ⁴⁰³ , R ⁴⁰⁴ and R ⁴⁰⁵ represent a carboxyl group.

In the general formula (X2), R ⁵⁰¹ , R ⁵⁰² , R ⁵⁰³ , R ⁵⁰⁴ , R ⁵⁰⁵ , R ⁵⁰⁶ and R ⁵⁰⁷ each independently represent a hydrogen atom or a substituent. However, R ⁵⁰¹ , R ⁵⁰² , R ⁵⁰³ , R ⁵⁰⁴ , R ⁵⁰⁵ , R ⁵⁰⁶ and R ⁵⁰⁷ satisfy the following conditions (iii) or (iv). * Represents a bond that binds to a sulfur atom.
Condition (iii): At ^{least one of R 501} , R ⁵⁰² , R ⁵⁰³ , R ⁵⁰⁴ , R ⁵⁰⁵ , R ⁵⁰⁶ and R ⁵⁰⁷ represents a hydroxyl group, and at least one represents a carboxyl group.
Condition (iv): At ^{least two of R 501} , R ⁵⁰² , R ⁵⁰³ , R ⁵⁰⁴ , R ⁵⁰⁵ , R ⁵⁰⁶ and R ⁵⁰⁷ represent a carboxyl group.

In the general formula (X3), R ⁶⁰¹ and R ⁶⁰² , R ⁶⁰³ , R ⁶⁰⁴ , R ⁶⁰⁵ , R ⁶⁰⁶ and R ⁶⁰⁷ each independently represent a hydrogen atom or a substituent. However, R ⁶⁰¹ and R ⁶⁰² , R ⁶⁰³ , R ⁶⁰⁴ , R ⁶⁰⁵ , R ⁶⁰⁶ and R ⁶⁰⁷ satisfy the following conditions (v) or (vi). * Represents a bond that binds to a sulfur atom.
Condition (v): At ^{least one of R 601} and R ⁶⁰² , R ⁶⁰³ , R ⁶⁰⁴ , R ⁶⁰⁵ , R ⁶⁰⁶ and R ⁶⁰⁷ represents a hydroxyl group, and at least one represents a carboxyl group.
Condition (vi): At ^{least two of R 601} , R ⁶⁰² , R ⁶⁰³ , R ⁶⁰⁴ , R ⁶⁰⁵ , R ⁶⁰⁶ and R ⁶⁰⁷ represent a carboxyl group.

In the general formula (D), Y ₁ and Y ₂ each independently represent a hydrogen atom or a substituent. Z _{1 to} Z ₅ independently represent a hydrogen atom or a substituent. M ₁ and M ₂ independently represent a hydrogen atom, an ammonium ion, an alkali metal ion or an organic cation, respectively. X in the general formula (A) represents a substituent represented by the general formula (X1), and R ⁴⁰¹ , R ⁴⁰² , R ⁴⁰³ , R ⁴⁰⁴ and R ^{405 in the} general formula (X1) are said. The coloring composition according to claim 1, which satisfies the condition (i). X in the general formula (A) represents a substituent represented by the general formula (X2), and R ⁵⁰¹ , R ⁵⁰² , R ⁵⁰³ , R ⁵⁰⁴ , R ⁵⁰⁵ , R in the general formula (X2). The coloring composition according to claim 1, wherein ⁵⁰⁶ and R ^{507 satisfy the above condition (iii).} X in the general formula (A) represents a substituent represented by the general formula (X3), and R ⁶⁰¹ , R ⁶⁰² , R ⁶⁰³ , R ⁶⁰⁴ , R ⁶⁰⁵ , R in the general formula (X3). ^{The coloring composition according to claim 1, wherein 606} and R ⁶⁰⁷ satisfy the above-mentioned condition (v). Claims 1 to the total content of the compound represented by the general formula (1) and the compound represented by the general formula (D) is 1.5 to 5.0% by mass in the coloring composition. The coloring composition according to any one of 4. Wherein _W 1 / _{W D} coloring composition according to any one of claims 1 to 5 is 95 / 5-90 / 10. The coloring composition according to any one of claims 1 to 6, further comprising a coloring material other than the compound represented by the general formula (1) and the compound represented by the general formula (D). An ink for inkjet recording using the coloring composition according to any one of claims 1 to 7. The inkjet recording method using the inkjet recording ink according to claim 8. An inkjet printer cartridge filled with the inkjet recording ink according to claim 8.