JP2018168268A - Ink composition and inkjet recording method - Google Patents

Abstract

【Task】
To provide an ink that can be stably ejected and has low foaming property and excellent defoaming property while maintaining high color saturation and high image fastness as compared with conventional ones.
Using an ink composition containing a compound represented by the general formula (1), a betaine compound represented by the general formula (2A), and an antifoaming agent, and the above ink composition, an image is obtained. An ink jet recording method to be formed.
[Selection figure] None

Description

  The present invention relates to an ink composition and an ink jet recording method.

As is well known, the ink jet recording method is a method of performing printing by causing a small droplet of ink to fly and adhere to a recording medium such as paper. This printing method is capable of printing high-resolution, high-quality images at high speed and easily with an inexpensive apparatus. In particular, in color printing, technical development has recently been carried out as an image forming method that can replace photographs. .
For example, Patent Document 1 describes an ink for inkjet recording using a xanthene derivative having a specific structure as a dye.
A betaine compound is added to the dye ink for the purpose of improving moisture resistance and the like, but at that time, the foaming property and defoaming property of the ink become problems, which may cause ejection failure. In order to solve this, it is known to add an antifoaming agent to the ink.
Patent Documents 2, 3 and 4 describe ink compositions containing a betaine compound and an antifoaming agent.

International Publication No. 2016/052687 JP 2009-41022 A JP 2007-302804 A JP 2007-302802 A

  In recent years, it has been required to achieve a higher level of performance than ever for images obtained by the ink jet recording method. Specifically, further improvement in image fastness to light, humidity, etc. is required. It has been.

  SUMMARY OF THE INVENTION An object of the present invention is to provide an ink that can be stably ejected with low foaming property and excellent defoaming property while maintaining high saturation and high image fastness as compared with the prior art. .

  The present inventors diligently studied to solve the above problems and found that the above problems can be solved by an ink composition in which an antifoaming agent is added to a combination ink of a specific xanthene dye and a betaine compound.

  The present invention is as follows.

[1]
An ink composition comprising a compound represented by the following general formula (1), a betaine compound represented by the following general formula (2A), and an antifoaming agent.

In general formula (1),
R ¹ , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁸ , R ⁹ , R ¹⁰ , R ¹¹ , R ¹² , R ¹³ , R ¹⁴ , R ¹⁵ , R ¹⁶ , R ¹⁷ , R ¹⁸ , R ¹⁹ And R ²⁰ each independently represents a hydrogen atom or a substituent, and X ¹ and X ² each independently represent a hydroxyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted group Heterocyclic oxy group, substituted or unsubstituted alkylamino group, substituted or unsubstituted arylamino group, substituted or unsubstituted heterylamino group, substituted carbonylamino group, substituted or unsubstituted acyloxy group, substituted or unsubstituted amino A carbonyloxy group, a substituted sulfonylamino group, a substituted or unsubstituted alkylthio group, or a substituted or unsubstituted arylthio group is represented. .
General formula (2A):
(R _a ) _p -N- [L _a- (COOM _a ) _q ] _r
In general formula (2A),
Each R _a independently represents a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group. L _a represents a divalent or higher linking group. M _a represents a hydrogen atom, an alkali metal atom, an ammonium group, a protonated organic amine or a nitrogen-containing heterocyclic group, or a quaternary ammonium ion group, and is a counter ion of an ammonium ion composed of an N atom in the formula. In the case, it represents a group that does not exist as a cation.
q represents an integer of 1 or more, and r represents an integer of 1 to 4. p represents an integer of 0 or more and 4 or less, and p + r is 3 or 4. When p + r is 4, the N atom is a protonated ammonium atom.
When q is 2 or more, the plurality of COOM _a may be the same or different. When r is 2 or more, L _a- (COOM _a ) _q may be the same or different. When p is 2 or more, the plurality of R _a may be the same or different.

[2]
The ink composition according to [1], wherein the compound represented by the general formula (1) is a compound represented by the following general formula (1-1).

In general formula (1-1),
R ¹ , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁸ , R ⁹ , R ¹⁰ , R ¹¹ , R ¹² , R ¹³ , R ¹⁴ , R ¹⁵ , R ¹⁶ , R ¹⁷ , R ¹⁸ , R ¹⁹ And R ²⁰ each independently represents a hydrogen atom or a substituent, and R ¹⁰¹ and R ¹⁰² each independently represent a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted group Represents a carbonyl group or a substituted sulfonyl group.

[3]
R ¹⁰¹ and R ¹⁰² are each independently a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted sulfonyl group, a substituted or unsubstituted alkoxycarbonyl group, substituted or unsubstituted Unsubstituted aryloxycarbonyl group, carbamoyl group, substituted or unsubstituted monoalkylaminocarbonyl group, substituted or unsubstituted dialkylaminocarbonyl group, substituted or unsubstituted monoarylaminocarbonyl group, substituted or unsubstituted diarylamino The ink composition according to [2], which represents a carbonyl group or a substituted or unsubstituted alkylarylaminocarbonyl group.
[4]
[1] to [3] wherein R ¹ , R ⁵ , R ⁶ , and R ^{10 in the} general formula (1) or the general formula (1-1) each independently represent an alkyl group having 1 to 6 carbon atoms. ] The ink composition of any one of these.

[5]
The ink composition according to any one of [1] to [4], wherein R ¹² and R ^{15 in the} general formula (1) or the general formula (1-1) each independently represent a sulfo group.
[6]
The ink composition according to any one of [1] to [5], wherein the betaine compound represented by the general formula (2A) is a compound represented by the following general formula (2A-1).

In the general formula (2A-1),
R _{a1 to} R _a3 each independently represents a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, and La represents _a divalent linking group.

[7]
Any one of [1] to [6], wherein the antifoaming agent is a compound represented by the following general formula (3), a compound represented by the following general formula (4), or a silicone-based antifoaming agent. The ink composition described in 1.

In the general formula (3), R ³¹ and R ³² each independently represent a hydrogen atom, a substituted or unsubstituted aliphatic group, or a substituted or unsubstituted aromatic group.

In the general formula (4),
R ₄₁ represents a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, R ₄₂ represents a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 5 carbon atoms, t is 1 to 1 An integer of 100 is represented.

[8]
The ink composition according to any one of [1] to [7], wherein the content of the betaine compound is 0.01 to 20% by mass with respect to the total mass of the ink composition.
[9]
The ink composition according to any one of [1] to [7], wherein the content of the antifoaming agent is 0.01 to 3.0% by mass with respect to the total mass of the ink composition.
[10]
An inkjet recording method for forming an image using the ink composition according to any one of [1] to [9].

  According to the present invention, it is possible to provide an ink that can be stably ejected and has low foaming property and excellent defoaming property while maintaining high saturation and high image fastness as compared with the prior art.

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

(Substituent group A)
Halogen atom, alkyl group, cycloalkyl 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, carbamoyloxy group, alkoxycarbonyloxy group, aryloxycarbonyloxy group, amino group, acylamino group, aminocarbonylamino group, alkoxycarbonylamino group, aryloxycarbonylamino group, sulfamoylamino group, alkyl or arylsulfonyl Amino group, mercapto group, alkylthio group, arylthio group, heterocyclic thio group, sulfamoyl group, alkyl or arylsulfinyl group, alkyl or arylsulfonyl group, acyl group, aryloxy Examples include carbonyl groups, alkoxycarbonyl groups, carbamoyl groups, aryl or heterocyclic azo groups, imide groups, phosphino groups, phosphinyl groups, phosphinyloxy groups, phosphinylamino groups, silyl groups, and ionic hydrophilic groups. It is done. These substituents may be further substituted, and examples of the further substituent include a group selected from the substituent group A described above.

  As a halogen atom, a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom is mentioned, for example.

Examples of the alkyl group include linear or branched substituted or unsubstituted alkyl groups.
An alkyl group (for example, an alkyl group of an alkoxy group or an alkylthio group) in a substituent described below also represents such an alkyl group.
As the alkyl group, an alkyl group having 1 to 30 carbon atoms such as a methyl group, an ethyl group, an n-propyl group, an i-propyl group, a t-butyl group, an n-octyl group, an eicosyl group, 2- A chloroethyl group, a 2-cyanoethyl group, a 2-ethylhexyl group and the like can be mentioned.

  Examples of the cycloalkyl group include a substituted or unsubstituted cycloalkyl group, preferably a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, such as a cyclohexyl group, a cyclopentyl group, and 4-n-dodecylcyclohexyl. The bicycloalkyl group is preferably a substituted or unsubstituted bicycloalkyl group having 5 to 30 carbon atoms, that is, a monovalent group obtained by removing one hydrogen atom from a bicycloalkane having 5 to 30 carbon atoms. Examples thereof include a bicyclo [1,2,2] heptan-2-yl group and a bicyclo [2,2,2] octan-3-yl group.

  Examples of the aralkyl group include a substituted or unsubstituted aralkyl group, and the substituted or unsubstituted aralkyl group is preferably an aralkyl group having 7 to 30 carbon atoms. For example, a benzyl group and a 2-phenethyl group can be mentioned.

Examples of the alkenyl group include linear, branched, and cyclic substituted or unsubstituted alkenyl groups, and include cycloalkenyl groups and bicycloalkenyl groups.
Preferred examples of the alkenyl group include substituted or unsubstituted alkenyl groups having 2 to 30 carbon atoms such as vinyl group, allyl group, prenyl group, geranyl group, and oleyl group. Preferred examples of the cycloalkenyl group include Is a substituted or unsubstituted cycloalkenyl group having 3 to 30 carbon atoms, that is, a monovalent group obtained by removing one hydrogen atom of a cycloalkene having 3 to 30 carbon atoms, such as a 2-cyclopenten-1-yl group, 2-cyclohexen-1-yl group and the like. As the bicycloalkenyl group, a substituted or unsubstituted bicycloalkenyl group, preferably a substituted or unsubstituted bicycloalkenyl group having 5 to 30 carbon atoms, that is, a double bond A monovalent group obtained by removing one hydrogen atom from a bicycloalkene having one of, for example, bicyclo [2,2,1] Hept-2-en-1-yl group, a bicyclo [2,2,2] oct-2-en-4-yl group and the like.

  The alkynyl group is preferably a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms such as an ethynyl group, a propargyl group, and a trimethylsilylethynyl group.

  The aryl group is preferably a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, such as a phenyl group, a p-tolyl group, a naphthyl group, an m-chlorophenyl group, an o-hexadecanoylaminophenyl group, and the like. Can be mentioned.

  The heterocyclic group is preferably a monovalent group obtained by removing one hydrogen atom from a 5- or 6-membered substituted or unsubstituted aromatic or non-aromatic heterocyclic compound, and more preferably a carbon number. Examples thereof include 3 to 30 5- or 6-membered aromatic heterocyclic groups such as a 2-furyl group, a 2-thienyl group, a 2-pyrimidinyl group, and a 2-benzothiazolyl group. Examples of non-aromatic heterocyclic groups include morpholinyl groups.

  The alkoxy group is preferably a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, such as a methoxy group, an ethoxy group, an isopropoxy group, a t-butoxy group, an n-octyloxy group, or a 2-methoxyethoxy group. Etc.

  The aryloxy group is preferably a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, such as a phenoxy group, 2-methylphenoxy group, 4-t-butylphenoxy group, 3-nitrophenoxy group, 2 -Tetradecanoylaminophenoxy group etc. are mentioned.

  Preferred examples of the silyloxy group include substituted or unsubstituted silyloxy groups having 0 to 20 carbon atoms such as a trimethylsilyloxy group and a diphenylmethylsilyloxy group.

  Preferred examples of the heterocyclic oxy group include substituted or unsubstituted heterocyclic oxy groups having 2 to 30 carbon atoms, such as a 1-phenyltetrazole-5-oxy group and a 2-tetrahydropyranyloxy group.

  The acyloxy group is preferably a formyloxy group, a substituted or unsubstituted alkylcarbonyloxy group having 2 to 30 carbon atoms, a substituted or unsubstituted arylcarbonyloxy group having 6 to 30 carbon atoms, such as an acetyloxy group, Examples include a pivaloyloxy group, a stearoyloxy group, a benzoyloxy group, and a p-methoxyphenylcarbonyloxy group.

  The carbamoyloxy group is preferably a substituted or unsubstituted carbamoyloxy group having 1 to 30 carbon atoms, such as N, N-dimethylcarbamoyloxy group, N, N-diethylcarbamoyloxy group, morpholinocarbonyloxy group, N , N-di-n-octylaminocarbonyloxy group, Nn-octylcarbamoyloxy group and the like.

  The alkoxycarbonyloxy group is preferably a substituted or unsubstituted alkoxycarbonyloxy group having 2 to 30 carbon atoms, such as a methoxycarbonyloxy group, an ethoxycarbonyloxy group, a t-butoxycarbonyloxy group, or an n-octylcarbonyloxy group. Etc.

  The aryloxycarbonyloxy group is preferably a substituted or unsubstituted aryloxycarbonyloxy group having 7 to 30 carbon atoms, such as phenoxycarbonyloxy group, p-methoxyphenoxycarbonyloxy group, pn-hexadecyloxy. Examples include phenoxycarbonyloxy group.

  The amino group includes an alkylamino group, an arylamino group, and a heterocyclic amino group, preferably an amino group, a substituted or unsubstituted alkylamino group having 1 to 30 carbon atoms, a substituted or unsubstituted group having 6 to 30 carbon atoms. Examples of the substituted anilino group include a methylamino group, a dimethylamino group, an anilino group, an N-methyl-anilino group, a diphenylamino group, and a triazinylamino group.

  The acylamino group is preferably a formylamino group, a substituted or unsubstituted alkylcarbonylamino group having 1 to 30 carbon atoms, a substituted or unsubstituted arylcarbonylamino group having 6 to 30 carbon atoms, such as an acetylamino group, Examples include pivaloylamino group, lauroylamino group, benzoylamino group, 3,4,5-tri-n-octyloxyphenylcarbonylamino group, and the like.

  The aminocarbonylamino group is preferably a substituted or unsubstituted aminocarbonylamino group having 1 to 30 carbon atoms, such as a carbamoylamino group, N, N-dimethylaminocarbonylamino group, or N, N-diethylaminocarbonylamino group. And a morpholinocarbonylamino group.

  The alkoxycarbonylamino group is preferably a substituted or unsubstituted alkoxycarbonylamino group having 2 to 30 carbon atoms, such as methoxycarbonylamino group, ethoxycarbonylamino group, t-butoxycarbonylamino group, n-octadecyloxycarbonylamino. Group, N-methyl-methoxycarbonylamino group and the like.

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

  The sulfamoylamino group is preferably a substituted or unsubstituted sulfamoylamino group having 0 to 30 carbon atoms, such as a sulfamoylamino group, N, N-dimethylaminosulfonylamino group, Nn- Examples include octylaminosulfonylamino group.

The alkyl or arylsulfonylamino group is preferably a substituted or unsubstituted alkylsulfonylamino group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsulfonylamino group having 6 to 30 carbon atoms, such as a methylsulfonylamino group. Butylsulfonylamino group, phenylsulfonylamino group, 2,3,5-trichlorophenylsulfonylamino group, p-methylphenylsulfonylamino group, and the like.
Preferred examples of the alkylthio group include substituted or unsubstituted alkylthio groups having 1 to 30 carbon atoms, such as a methylthio group, an ethylthio group, and an n-hexadecylthio group.

  Preferred examples of the arylthio group include substituted or unsubstituted arylthio groups having 6 to 30 carbon atoms such as a phenylthio group, a p-chlorophenylthio group, and an m-methoxyphenylthio group.

  Preferred examples of the heterocyclic thio group include substituted or unsubstituted heterocyclic thio groups having 2 to 30 carbon atoms, such as a 2-benzothiazolylthio group and a 1-phenyltetrazol-5-ylthio group.

  The sulfamoyl group is preferably a substituted or unsubstituted sulfamoyl group having 0 to 30 carbon atoms, such as N-ethylsulfamoyl group, N- (3-dodecyloxypropyl) sulfamoyl group, N, N-dimethylsulfuryl group. Examples include a famoyl group, an N-acetylsulfamoyl group, an N-benzoylsulfamoyl group, and an N- (N′-phenylcarbamoyl) sulfamoyl group.

  The alkyl or arylsulfinyl group is preferably a substituted or unsubstituted alkylsulfinyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsulfinyl group having 6 to 30 carbon atoms, such as a methylsulfinyl group or an ethylsulfinyl group. , Phenylsulfinyl group, p-methylphenylsulfinyl group and the like.

  The alkyl or arylsulfonyl group is preferably a substituted or unsubstituted alkylsulfonyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsulfonyl group having 6 to 30 carbon atoms, such as a methylsulfonyl group or an ethylsulfonyl group. , Phenylsulfonyl group, p-methylphenylsulfonyl group and the like.

  The acyl group is preferably a formyl group, a substituted or unsubstituted alkylcarbonyl group having 2 to 30 carbon atoms, a substituted or unsubstituted arylcarbonyl group having 7 to 30 carbon atoms, a substituted or unsubstituted group having 2 to 30 carbon atoms. Heterocyclic carbonyl groups bonded to carbonyl groups at substituted carbon atoms, such as acetyl, pivaloyl, 2-chloroacetyl, stearoyl, benzoyl, pn-octyloxyphenylcarbonyl, 2-pyridyl Examples thereof include a carbonyl group and a 2-furylcarbonyl group.

  The aryloxycarbonyl group is preferably a substituted or unsubstituted aryloxycarbonyl group having 7 to 30 carbon atoms, such as phenoxycarbonyl group, o-chlorophenoxycarbonyl group, m-nitrophenoxycarbonyl group, pt- A butylphenoxycarbonyl group etc. are mentioned.

  The alkoxycarbonyl group is preferably a substituted or unsubstituted alkoxycarbonyl group having 2 to 30 carbon atoms, such as a methoxycarbonyl group, an ethoxycarbonyl group, a t-butoxycarbonyl group, and an n-octadecyloxycarbonyl group.

  The carbamoyl group is preferably a substituted or unsubstituted carbamoyl group having 1 to 30 carbon atoms, such as a carbamoyl group, an N-methylcarbamoyl group, an N, N-dimethylcarbamoyl group, or an N, N-di-n-octyl group. 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, such as a phenylazo group or p-chlorophenylazo group. Group, 5-ethylthio-1,3,4-thiadiazol-2-ylazo group and the like.

  Preferred examples of the imide group include an N-succinimide group and an N-phthalimide group.

  The phosphino group is preferably a substituted or unsubstituted phosphino group having 0 to 30 carbon atoms, such as a dimethylphosphino group, a diphenylphosphino group, a methylphenoxyphosphino group, and the like.

  The phosphinyl group is preferably a substituted or unsubstituted phosphinyl group having 0 to 30 carbon atoms, such as a phosphinyl group, a dioctyloxyphosphinyl group, a diethoxyphosphinyl group, and the like.

  Preferred examples of the phosphinyloxy group include substituted or unsubstituted phosphinyloxy groups having 0 to 30 carbon atoms such as a diphenoxyphosphinyloxy group and a dioctyloxyphosphinyloxy group.

  The phosphinylamino group is preferably a substituted or unsubstituted phosphinylamino group having 0 to 30 carbon atoms, such as a dimethoxyphosphinylamino group or a dimethylaminophosphinylamino group.

  Preferred examples of the silyl group include substituted or unsubstituted silyl groups having 0 to 30 carbon atoms such as a trimethylsilyl group, a t-butyldimethylsilyl group, and a phenyldimethylsilyl group.

  Examples of the ionic hydrophilic group include a sulfo group, a carboxyl group, a thiocarboxyl group, a sulfino group, a phosphono group, a dihydroxyphosphino group, and a quaternary ammonium group. Particularly preferred are a sulfo group and a carboxyl group. The ionic hydrophilic group may contain a cation or an anion, and a state containing the cation or anion is called a salt state. The carboxyl group, phosphono group and sulfo group may be in the form of a salt. Examples of counter cations that form salts include ammonium ions, alkali metal ions (eg, lithium ions, sodium ions, potassium ions) and organic cations. (Eg, tetramethylammonium ion, tetramethylguanidinium ion, tetramethylphosphonium) are included, lithium salts, sodium salts, potassium salts, and ammonium salts are preferable, and mixed salts containing sodium salts or sodium salts as main components are included. More preferred is the sodium salt.

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

[Compound represented by the general formula (1)]

In general formula (1),
R ¹ , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁸ , R ⁹ , R ¹⁰ , R ¹¹ , R ¹² , R ¹³ , R ¹⁴ , R ¹⁵ , R ¹⁶ , R ¹⁷ , R ¹⁸ , R ¹⁹ And R ²⁰ each independently represents a hydrogen atom or a substituent, and X ¹ and X ² each independently represent a hydroxyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted group Heterocyclic oxy group, substituted or unsubstituted alkylamino group, substituted or unsubstituted arylamino group, substituted or unsubstituted heterylamino group, substituted carbonylamino group, substituted or unsubstituted acyloxy group, substituted or unsubstituted amino A carbonyloxy group, a substituted sulfonylamino group, a substituted or unsubstituted alkylthio group, or a substituted or unsubstituted arylthio group is represented. .

In the general formula ^{(1), R 1, R} 3, R 4, R 5, R 6, R 8, R 9, R 10, R 11, R 12, R 13, R 14, R 15, R 16, R ¹⁷ , R ¹⁸ , R ¹⁹ and R ²⁰ each independently represents a hydrogen atom or a substituent. R ¹ , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁸ , R ⁹ , R ¹⁰ , R ¹¹ , R ¹² , R ¹³ , R ¹⁴ , R ¹⁵ , R ¹⁶ , R ¹⁷ , R ¹⁸ , R ¹⁹ And when R ²⁰ is a substituent, examples of the substituent include a substituent selected from the substituent group A.

In general formula (1), R ¹ , R ⁵ , R ⁶ and R ¹⁰ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group, substituted or unsubstituted, from the viewpoint of availability of raw materials and ease of synthesis. It preferably represents a substituted aryl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a carboxyl group, or a halogen atom, more preferably a substituted or unsubstituted alkyl group, a substituted or unsubstituted group. An aryl group, a substituted or unsubstituted alkoxy group, and particularly preferably a substituted or unsubstituted alkyl group. As an alkyl group, a C1-C6 alkyl group is preferable, a C1-C3 alkyl group is more preferable, and a methyl group is still more preferable. Moreover, the substituent selected from the said substituent group A is mentioned as a substituent in case each group has a substituent.

In general formula (1), R ⁴ and R ⁹ are each independently a hydrogen atom, substituted or non-substituted from the viewpoints of availability of raw materials and ease of synthesis, light resistance, ozone resistance, print density, and saturation. Substituted alkyl group, substituted or unsubstituted aryl group, substituted or unsubstituted alkoxy group, substituted or unsubstituted aryloxy group, substituted or unsubstituted amino group, substituted or unsubstituted acylamino group, substituted or unsubstituted Alkoxycarbonylamino group, substituted or unsubstituted alkylsulfonylamino group, substituted or unsubstituted arylsulfonylamino group, substituted or unsubstituted alkylureido group, substituted or unsubstituted arylureido group, sulfo group, carboxyl group, Or a halogen atom, preferably a hydrogen atom, substituted or unsubstituted Acylamino group, substituted or unsubstituted alkoxycarbonylamino group, substituted or unsubstituted alkylsulfonylamino group, substituted or unsubstituted arylsulfonylamino group, substituted or unsubstituted alkylureido group, substituted or unsubstituted arylureido Group or a sulfo group, particularly preferably a hydrogen atom or a sulfo group. Moreover, the substituent selected from the said substituent group A is mentioned as a substituent in case each group has a substituent.

In general formula (1), R ³ and R ⁸ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted group, from the viewpoint of availability of raw materials and ease of synthesis. Or an unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted acylamino group, a substituted or unsubstituted alkoxycarbonylamino group, a substituted or unsubstituted alkylsulfonylamino Preferably represents a group, a substituted or unsubstituted arylsulfonylamino group, a substituted or unsubstituted alkylureido group, a substituted or unsubstituted arylureido group, a sulfo group, a carboxyl group, or a halogen atom, more preferably a hydrogen atom. A substituted or unsubstituted alkyl group or a sulfo group, especially Mashiku is a substituted or unsubstituted alkyl group. As an alkyl group, a C1-C6 alkyl group is preferable, a C1-C3 alkyl group is more preferable, and a methyl group is still more preferable. Moreover, the substituent selected from the said substituent group A is mentioned as a substituent in case each group has a substituent.

In the general formula (1), R ¹¹ , R ¹⁴ , R ¹³ , R ¹⁶ , R ¹⁷ , R ¹⁸ , R ¹⁹ and R ²⁰ are each independently a hydrogen atom from the viewpoint of availability of raw materials and ease of synthesis. Preferably represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a hydroxy group, a halogen atom, or a sulfo group, and more A hydrogen atom, a hydroxy group, a halogen atom, or a sulfo group is preferable, and a hydrogen atom is particularly preferable. Moreover, the substituent selected from the said substituent group A is mentioned as a substituent in case each group has a substituent.

In general formula (1), R ¹² and R ¹⁵ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a halogen atom, from the viewpoint of availability of raw materials and ease of synthesis. Or a sulfo group, more preferably a hydrogen atom or a sulfo group, and particularly preferably a sulfo group. Moreover, the substituent selected from the said substituent group A is mentioned as a substituent in case each group has a substituent.

From the viewpoint of solubility, R ¹ , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁸ , R ⁹ , R ¹⁰ , R ¹¹ , R ¹² , R ¹³ , R in general formula (1) ^At least one of ¹⁴ , R ¹⁵ , R ¹⁶ , R ¹⁷ , R ¹⁸ , R ¹⁹ and R ²⁰ preferably has an ionic hydrophilic group such as a carboxyl group, a sulfo group, or a phosphono group. These ionic hydrophilic groups may be in a salt state. In this case, examples of the counter cation include alkali metal cations (lithium ions, sodium ions, or potassium ions), ammonium ions, and the like. From the viewpoint of ease (easy handling as a dye powder), an alkali metal cation is preferable.

X ¹ and X ² are each independently a hydroxyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heterocyclic oxy group, a substituted or unsubstituted alkylamino group, substituted Or unsubstituted arylamino group, substituted or unsubstituted heterylamino group, substituted carbonylamino group, substituted or unsubstituted acyloxy group, substituted or unsubstituted aminocarbonyloxy group, substituted sulfonylamino group, substituted or unsubstituted alkylthio A group, or a substituted or unsubstituted arylthio group;

Examples of the alkoxy group when X ¹ and X ² representing a substituted or unsubstituted alkoxy group, preferably an alkoxy group having 1 to 18 carbon atoms, more preferably an alkoxy group having 1 to 8 carbon atoms. The alkoxy group may be linear, branched or cyclic. Specifically, the alkoxy group is preferably a methoxy group, an ethoxy group, a propyloxy group, an isopropyloxy group, a cyclohexyloxy group, or a 2-ethylhexyloxy group. In addition, examples of the substituent in the case where the alkoxy group has a substituent include a substituent selected from the above substituent group A, an ionic hydrophilic group is preferable, a carboxyl group or a sulfo group is more preferable, and a carboxyl group is further preferable.

When X ¹ and X ² represent a substituted or unsubstituted aryloxy group, the aryloxy group is preferably an aryloxy group having 6 to 14 carbon atoms, more preferably an aryloxy group having 6 to 10 carbon atoms, and phenyl. An oxy group is more preferable. In addition, examples of the substituent in the case where the aryloxy group has a substituent include a substituent selected from the above-mentioned substituent group A, an ionic hydrophilic group is preferable, a carboxyl group or a sulfo group is more preferable, and a carboxyl group is Further preferred.

The heterocyclic group contained in the heterocyclic oxy group when X ¹ and X ² represent a substituted or unsubstituted heterocyclic oxy group is preferably a triazine group, a thiazolyl group, a benzothiazolyl group, or a thiadiazolyl group. Further, the substituent in the case where the heterocyclic oxy group has a substituent includes a substituent selected from the above-mentioned substituent group A, and a substituted or unsubstituted amino group, a substituted or unsubstituted sulfamoyl group is preferable, Alternatively, an unsubstituted alkylamino group, a substituted or unsubstituted alkylsulfamoyl group is more preferable, and an ionic hydrophilic group (preferably a carboxyl group or a sulfo group, more preferably a carboxyl group) substituted with an alkylamino group or Alkylsulfamoyl groups are particularly preferred.

The alkyl group contained in the alkylamino group when X ¹ and X ² represent a substituted or unsubstituted alkylamino group is preferably an alkyl group having 1 to 6 carbon atoms, more preferably an alkyl group having 1 to 3 carbon atoms. A methyl group or an ethyl group is more preferable. Moreover, as a substituent in case an alkyl group has a substituent, the substituent chosen from the said substituent group A is mentioned, An aryl group is preferable and a phenyl group is especially preferable.

The aryl group contained in the arylamino group when X ¹ and X ² represent a substituted or unsubstituted arylamino group is preferably an aryl group having 6 to 14 carbon atoms, more preferably an aryl group having 6 to 10 carbon atoms. Preferably, a phenyl group is more preferable. In addition, examples of the substituent in the case where the aryl group has a substituent include substituents selected from the above substituent group A.

The heterocyclic group contained in the heteroaryl amino group when X ¹ and X ² represent a substituted or unsubstituted heteroaryl amino group is preferably a triazine group, a thiazolyl group, a benzothiazolyl group, or a thiadiazolyl group. Further, the substituent in the case where the heterocyclic oxy group has a substituent includes a substituent selected from the above-mentioned substituent group A, and a substituted or unsubstituted amino group, a substituted or unsubstituted sulfamoyl group is preferable, Alternatively, an unsubstituted alkylamino group, a substituted or unsubstituted alkylsulfamoyl group is more preferable, and an ionic hydrophilic group (preferably a carboxyl group or a sulfo group, more preferably a carboxyl group) substituted with an alkylamino group or Alkylsulfamoyl groups are particularly preferred.

Examples of the substituted carbonylamino group when X ¹ and X ² represent a substituted carbonylamino group include, for example, a substituted or unsubstituted alkoxycarbonylamino group, a substituted or unsubstituted aryloxycarbonylamino group, a substituted or unsubstituted ureido Group.

The alkyl group contained in the alkoxycarbonylamino group when X ¹ and X ² represent a substituted or unsubstituted alkoxycarbonylamino group is preferably an alkyl group having 1 to 6 carbon atoms, and an alkyl group having 1 to 3 carbon atoms. Are more preferable, and a methyl group or an ethyl group is still more preferable. Moreover, as a substituent in case an alkyl group has a substituent, the substituent chosen from the said substituent group A is mentioned, An aryl group is preferable and a phenyl group is especially preferable.

The aryl group contained in the aryloxycarbonylamino group when X ¹ and X ² represent a substituted or unsubstituted aryloxycarbonylamino group is preferably an aryl group having 6 to 14 carbon atoms, and having 6 to 10 carbon atoms. An aryl group is more preferable, and a phenyl group is still more preferable. In addition, examples of the substituent in the case where the aryl group has a substituent include substituents selected from the above substituent group A.

Examples of the ureido group in which X ¹ and X ² are substituted or unsubstituted include a ureido group substituted with an alkyl group or an aryl group.
The alkyl group contained in the ureido group substituted with an alkyl group when X ¹ and X ² represent a ureido group substituted with an alkyl group is preferably an alkyl group having 1 to 6 carbon atoms, and having 1 to 3 carbon atoms. Are more preferable, and a methyl group or an ethyl group is still more preferable. Moreover, as a substituent in case an alkyl group has a substituent, the substituent chosen from the said substituent group A is mentioned, An aryl group is preferable and a phenyl group is especially preferable.
The aryl group contained in a ureido group substituted with an aryl group when it represents a ureido group in which X ¹ and X ² is substituted by an aryl group, preferably an aryl group having 6 to 14 carbon atoms, 6 carbon atoms 10 to 10 aryl groups are more preferable, and a phenyl group is still more preferable. In addition, examples of the substituent in the case where the aryl group has a substituent include substituents selected from the above substituent group A.

When X ¹ and X ² represent a substituted or unsubstituted acyloxy group, the acyloxy group is preferably an acyloxy group having 1 to 18 carbon atoms, and more preferably an acyloxy group having 1 to 8 carbon atoms. Specific examples of the acyloxy group include an acetyloxy group and a benzoyloxy group, and acetyloxy is preferable. In addition, examples of the substituent in the case where the acyloxy group has a substituent include a substituent selected from the above substituent group A, an ionic hydrophilic group is preferable, a carboxyl group or a sulfo group is more preferable, and a carboxyl group is further preferable.

When X ¹ and X ² represent a substituted or unsubstituted aminocarbonyloxy group, the aminocarbonyloxy group is preferably an aminocarbonyloxy group having 1 to 18 carbon atoms, and an aminocarbonyloxy group having 1 to 8 carbon atoms is preferred. More preferred. Specific examples of the aminocarbonyloxy group include an unsubstituted aminocarbonyloxy group, a dimethylaminocarbonyloxy group, and a phenylaminocarbonyloxy group, and an unsubstituted aminocarbonyloxy group and a dimethylaminocarbonyloxy group are preferable. In addition, the substituent in the case where the aminocarbonyloxy group has a substituent includes a substituent selected from the above substituent group A, an ionic hydrophilic group is preferable, a carboxyl group or a sulfo group is more preferable, and a carboxyl group Is more preferable.

Examples of the substituted sulfonylamino group when X ¹ and X ² represent a substituted sulfonylamino group include a substituted or unsubstituted alkylsulfonylamino group and a substituted or unsubstituted arylsulfonylamino group.

As the alkylsulfonylamino group when X ¹ and X ² represent a substituted or unsubstituted alkylsulfonylamino group, an alkylsulfonylamino group having 1 to 6 carbon atoms is preferable, and an alkylsulfonylamino group having 1 to 3 carbon atoms is preferable. More preferred is a methylsulfonylamino group. Moreover, the substituent selected from the said substituent group A is mentioned as a substituent in case an alkylsulfonylamino group has a substituent.

As the arylsulfonylamino group when X ¹ and X ² represent a substituted or unsubstituted arylsulfonylamino group, an arylsulfonylamino group having 6 to 14 carbon atoms is preferable, and an arylsulfonylamino group having 6 to 10 carbon atoms is preferable. More preferred is a phenylsulfonylamino group. In addition, examples of the substituent when the arylsulfonylamino group has a substituent include substituents selected from the above substituent group A, and a carboxyl group is particularly preferable.

The alkylthio group in the case where X ¹ and X ² represent a substituted or unsubstituted alkylthio group is preferably an alkylthio group having 1 to 18 carbon atoms, and more preferably an alkylthio group having 1 to 8 carbon atoms. Specific examples of the alkylthio group include a methylthio group, an ethylthio group, and a propylthio group. A methylthio group and an ethylthio group are preferable, and a methylthio group is more preferable. In addition, examples of the substituent in the case where the alkylthio group has a substituent include a substituent selected from the above substituent group A, an ionic hydrophilic group is preferable, a carboxyl group or a sulfo group is more preferable, and a carboxyl group is further preferable.

When X ¹ and X ² represent a substituted or unsubstituted arylthio group, the arylthio group is preferably an arylthio group having 6 to 14 carbon atoms, more preferably an arylthio group having 6 to 10 carbon atoms, and still more preferably a phenylthio group. . In addition, examples of the substituent in the case where the arylthio group has a substituent include a substituent selected from the above-mentioned substituent group A, an ionic hydrophilic group is preferable, a carboxyl group or a sulfo group is more preferable, and a carboxyl group is still more preferable. .

  The compound represented by the general formula (1) is preferably a compound represented by the general formula (1-1).

In general formula (1-1),
R ¹ , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁸ , R ⁹ , R ¹⁰ , R ¹¹ , R ¹² , R ¹³ , R ¹⁴ , R ¹⁵ , R ¹⁶ , R ¹⁷ , R ¹⁸ , R ¹⁹ And R ²⁰ each independently represents a hydrogen atom or a substituent, and R ¹⁰¹ and R ¹⁰² each independently represent a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted group Represents a carbonyl group or a substituted sulfonyl group.

  The compound represented by the general formula (1-1) has an amino group having a specific substituent. Although the mechanism of action is unknown, it is considered that the compound represented by the general formula (1-1) has such a structure and exhibits high chroma, excellent printing density, light resistance, and ozone resistance. It is done.

In the general formula (1-1), R ¹ , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁸ , R ⁹ , R ¹⁰ , R ¹¹ , R ¹² , R ¹³ , R ¹⁴ , R ¹⁵ , R ¹⁶ , R ¹⁷ , R ¹⁸ , R ¹⁹ and R ²⁰ are R ¹ , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁸ , R ⁹ , R ¹⁰ , R ¹¹ , in the general formula (1). It is synonymous with R < ¹² >, R <^13> , R <^14> , R <^15> , R <^16> , R <^17> , R <^18> , R < ¹⁹ > and R < ²⁰ >, and the preferred range is also the same.

In general formula (1-1), R ¹⁰¹ and R ¹⁰² are each independently a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted carbonyl group, or a substituted sulfonyl group. Represents a group.

When R ¹⁰¹ and R ¹⁰² represent a substituted or unsubstituted alkyl group, 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, a methyl group or an ethyl group. Is more preferable. Moreover, as a substituent in case an alkyl group has a substituent, the substituent chosen from the said substituent group A is mentioned, An aryl group is preferable and a phenyl group is especially preferable.
When R ¹⁰¹ and R ¹⁰² represent a substituted or unsubstituted aryl group, the aryl group is preferably an aryl group having 6 to 14 carbon atoms, more preferably an aryl group having 6 to 10 carbon atoms, and further preferably a phenyl group. . In addition, examples of the substituent in the case where the aryl group has a substituent include substituents selected from the above substituent group A.
When R ¹⁰¹ and R ¹⁰² represent a substituted or unsubstituted heterocyclic group, the heterocyclic group is preferably a triazine group, a thiazolyl group, a benzothiazolyl group, or a thiadiazolyl group. In addition, examples of the substituent in the case where the heterocyclic group has a substituent include a substituent selected from the above substituent group A, and a substituted or unsubstituted amino group and a substituted or unsubstituted sulfamoyl group are preferable.

Examples of the substituted sulfonyl group when R ¹⁰¹ and R ¹⁰² represent a substituted sulfonyl group include a substituted or unsubstituted alkylsulfonyl group, a substituted or unsubstituted arylsulfonyl group, and the like.
The alkylsulfonyl group in the case where R ¹⁰¹ and R ¹⁰² represent a substituted or unsubstituted alkylsulfonyl group is preferably an alkylsulfonyl group having 1 to 6 carbon atoms, more preferably an alkylsulfonyl group having 1 to 3 carbon atoms, and methyl More preferred is a sulfonyl group. In addition, examples of the substituent when the alkylsulfonyl group has a substituent include a substituent selected from the above substituent group A.
In the case where R ¹⁰¹ and R ¹⁰² represent a substituted or unsubstituted arylsulfonyl group, the arylsulfonyl group is preferably an arylsulfonyl group having 6 to 14 carbon atoms, more preferably an arylsulfonyl group having 6 to 10 carbon atoms, More preferred is a sulfonyl group. In addition, examples of the substituent in the case where the arylsulfonyl group has a substituent include a substituent selected from the above substituent group A, and a carboxyl group is particularly preferable.

Examples of the substituted carbonyl group when R ¹⁰¹ and R ¹⁰² represent a substituted carbonyl group include, for example, a substituted or unsubstituted alkoxycarbonyl group, a substituted or unsubstituted aryloxycarbonyl group, a carbamoyl group, a substituted or unsubstituted monoalkyl Examples include an aminocarbonyl group, a substituted or unsubstituted dialkylaminocarbonyl group, a substituted or unsubstituted monoarylaminocarbonyl group, a substituted or unsubstituted diarylaminocarbonyl group, or a substituted or unsubstituted alkylarylaminocarbonyl group. .

In the case where R ¹⁰¹ and R ¹⁰² represent a substituted or unsubstituted alkoxycarbonyl group, the alkoxycarbonyl group is preferably represented by —COOR ²⁰¹ . Here, R ²⁰¹ represents an alkyl group having 1 to 6 carbon atoms, preferably an alkyl group having 1 to 4 carbon atoms, and more preferably an isopropyl group. In addition, examples of the substituent in the case where the alkoxycarbonyl group has a substituent include a substituent selected from the above substituent group A.
When R ¹⁰¹ and R ¹⁰² represent a substituted or unsubstituted aryloxycarbonyl group, the aryloxycarbonyl group is preferably represented by —COOR ²⁰² .
R ²⁰² represents an aryl group having 6 to 14 carbon atoms, preferably an aryl group having 6 to 10 carbon atoms, and more preferably a phenyl group. In addition, examples of the substituent in the case where the aryloxycarbonyl group has a substituent include a substituent selected from the above substituent group A, and a nitro group is particularly preferable.
When R ¹⁰¹ and R ¹⁰² represent a substituted or unsubstituted monoalkylaminocarbonyl group, the monoalkylaminocarbonyl group is preferably represented by —CONHR ²⁰³ . Here, R ²⁰³ represents an alkyl group having 1 to 12 carbon atoms, preferably an alkyl group having 1 to 10 carbon atoms, more preferably an alkyl group having 1 to 6 carbon atoms, a methyl group, an ethyl group, an isopropyl group, a hexyl group. 2-ethylhexyl group, dodecyl group and cyclohexyl group are more preferable, and isopropyl group is particularly preferable. In addition, the substituent in the case where the monoalkylaminocarbonyl group has a substituent includes a substituent selected from the above substituent group A, and particularly a phenyl group, a carboxyl group, a substituted or unsubstituted amino group, and a hydroxyl group. preferable.
When R ¹⁰¹ and R ¹⁰² represent a substituted or unsubstituted dialkylaminocarbonyl group, the dialkylaminocarbonyl group is preferably represented by —CONR ²⁰⁴ R ²⁰⁵ . Here, R ²⁰⁴ and R ²⁰⁵ each independently represent an alkyl group having 1 to 10 carbon atoms, preferably an alkyl group having 1 to 6 carbon atoms, and more preferably a methyl group or an isopropyl group. In addition, examples of the substituent in the case where the dialkylaminocarbonyl group has a substituent include a substituent selected from the above-mentioned substituent group A, and include a carboxyl group and an alkyloxycarbonyl group (preferably an alkyloxycarbonyl having 2 to 6 carbon atoms). Group, more preferably an ethyloxycarbonyl group).
When R ¹⁰¹ and R ¹⁰² represent a substituted or unsubstituted monoarylaminocarbonyl group, the monoarylaminocarbonyl group is preferably represented by —CONHR ²⁰⁶ . R ²⁰⁶ represents an aryl group having 6 to 14 carbon atoms, preferably an aryl group having 6 to 12 carbon atoms, and more preferably an aryl group having 6 to 10 carbon atoms. Specifically, a phenyl group, a biphenyl group, and a naphthyl group are preferable, and a phenyl group is more preferable. In addition, examples of the substituent in the case where the monoarylaminocarbonyl group has a substituent include a substituent selected from the above substituent group A, and include a carboxyl group, a hydroxyl group, a phosphono group, and an alkoxy group (preferably having a carbon number of 1 to 6 alkoxy group, more preferably cyclohexyloxy group).
When R ¹⁰¹ and R ¹⁰² represent a substituted or unsubstituted diarylaminocarbonyl group, the diarylaminocarbonyl group is preferably represented by —CONR ²⁰⁷ R ²⁰⁸ . Wherein ^{R 207} and ^{R 208} represents an aryl group having 6 to 14 carbon atoms each independently, preferably an aryl group having 6 to 10 carbon atoms, a phenyl group is more preferable. In addition, examples of the substituent in the case where the diarylaminocarbonyl group has a substituent include a substituent selected from the above substituent group A.

R ¹⁰¹ and R ¹⁰² are preferably a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted sulfonyl group, a substituted or unsubstituted alkoxycarbonyl group, substituted or unsubstituted Unsubstituted aryloxycarbonyl group, carbamoyl group, substituted or unsubstituted monoalkylaminocarbonyl group, substituted or unsubstituted dialkylaminocarbonyl group, substituted or unsubstituted monoarylaminocarbonyl group, substituted or unsubstituted diarylamino A carbonyl group, or a substituted or unsubstituted alkylarylaminocarbonyl group.

R ¹⁰¹ and R ¹⁰² are preferably a substituted or unsubstituted alkylsulfonyl group, a substituted or unsubstituted arylsulfonyl group, a substituted or unsubstituted alkoxycarbonyl group from the viewpoints of chroma, light resistance and ozone resistance. Substituted or unsubstituted aryloxycarbonyl group, carbamoyl group, substituted or unsubstituted monoalkylaminocarbonyl group, substituted or unsubstituted dialkylaminocarbonyl group, substituted or unsubstituted monoarylaminocarbonyl group, or substituted or unsubstituted A substituted diarylaminocarbonyl group, more preferably a substituted or unsubstituted alkylsulfonyl group, a substituted or unsubstituted arylsulfonyl group, a substituted or unsubstituted monoalkylaminocarbonyl group, a substituted or unsubstituted dialkyl A minocarbonyl group, a substituted or unsubstituted monoarylaminocarbonyl group, or a substituted or unsubstituted diarylaminocarbonyl group, particularly preferably a substituted or unsubstituted monoalkylaminocarbonyl group, a substituted or unsubstituted dialkylaminocarbonyl group; A group, a substituted or unsubstituted monoarylaminocarbonyl group, or a substituted or unsubstituted diarylaminocarbonyl group.

  Although the specific example of a compound represented by General formula (1) below is given, it is not necessarily limited to these. In the structural formulas of the following specific compounds, Me represents a methyl group.

  As specific examples of the compound represented by the general formula (1), the compound (1-5) and the compound (1-6) are preferable.

[Betaine Compound Represented by General Formula (2A)]
The ink composition of the present invention contains a betaine compound represented by the general formula (2A). The betaine compound can be used as a surfactant.

General formula (2A):
(R _a ) _p -N- [L _a- (COOM _a ) _q ] _r
In general formula (2A),
Each R _a independently represents a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group. L _a represents a divalent or higher linking group. M _a represents a hydrogen atom, an alkali metal atom, an ammonium group, a protonated organic amine or a nitrogen-containing heterocyclic group, or a quaternary ammonium ion group, and is a counter ion of an ammonium ion composed of an N atom in the formula. In the case, it represents a group that does not exist as a cation.
q represents an integer of 1 or more, and r represents an integer of 1 to 4. p represents an integer of 0 or more and 4 or less, and p + r is 3 or 4. When p + r is 4, the N atom is a protonated ammonium atom.
When q is 2 or more, the plurality of COOM _a may be the same or different. When r is 2 or more, L _a- (COOM _a ) _q may be the same or different. When p is 2 or more, the plurality of R _a may be the same or different.

As the betaine compound used in the present invention, among the compounds represented by the general formula (2A), a compound represented by the following general formula (2A-1) or (2A-2) is particularly preferably used. The compound represented by (2A-1) is more preferably used.
General formula (2A-1):

In general formula (2A-1), R _a1 , R _a2 and R _a3 are each independently a substituted or unsubstituted alkyl group (preferably a group having 1 to 20 carbon atoms. For example, a methyl group, an ethyl group, a propyl group, Group, butyl group, hexyl group, octyl group, dodecyl group, cetyl group, stearyl group, oleyl group, etc.), substituted or unsubstituted aryl group (preferably a group having 6 to 20 carbon atoms. For example, phenyl group, tolyl group) Group, xylyl group, naphthyl group, cumyl group, dodecylphenyl group, etc.) or a substituted or unsubstituted heterocyclic group (preferably a group having 2 to 20 carbon atoms, such as pyridyl group, quinolyl group, etc.). , Each may be connected to each other to form an annular structure.
Among these, a substituted or unsubstituted alkyl group is preferable, and a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms is particularly preferable.

L _a represents a divalent linking group. As this example, a divalent linking group containing an alkylene group or an arylene group as a basic structural unit is preferable. You may contain hetero atoms, such as an oxygen atom, a sulfur atom, and a nitrogen atom, in a connection main chain part.
The preferred L _a, a substituted or unsubstituted alkylene group having 1 to 18 carbon atoms, more preferably an unsubstituted alkylene group having 1 to 8 carbon atoms, particularly preferably methylene group or ethylene group, .

The R _a1, R _a2, R _a3 and L _a may have various substituents.
For example, an alkyl group (preferably having 1 to 20 carbon atoms, more preferably 1 to 12 carbon atoms, particularly preferably 1 to 8 carbon atoms, such as methyl, ethyl, iso-propyl, tert-butyl, n-octyl, n -Decyl, n-hexadecyl, cyclopropyl, cyclopentyl, cyclohexyl, etc.), an alkenyl group (preferably having 2 to 20 carbon atoms, more preferably 2 to 12 carbon atoms, particularly preferably 2 to 8 carbon atoms). For example, vinyl, allyl, 2-butenyl, 3-pentenyl, etc.), an alkynyl group (preferably having 2 to 20 carbon atoms, more preferably 2 to 12 carbon atoms, and particularly preferably 2 to 8 carbon atoms). , For example, propargyl, 3-pentynyl, etc.), an aryl group (preferably having 6 to 30 carbon atoms, more preferably carbon number) To 20 and particularly preferably 6 to 12 carbon atoms, such as phenyl, p-methylphenyl, naphthyl, etc.), amino groups (preferably having 0 to 20 carbon atoms, more preferably 0 to 12 carbon atoms, Particularly preferably, it has 0 to 6 carbon atoms, and examples thereof include amino, methylamino, dimethylamino, diethylamino, diphenylamino, dibenzylamino and the like, and an alkoxy group (preferably having 1 to 20 carbon atoms, more preferably carbon. 1 to 12, particularly preferably 1 to 8 carbon atoms such as methoxy, ethoxy, butoxy, etc.), an aryloxy group (preferably 6 to 20 carbon atoms, more preferably 6 to 16 carbon atoms, Particularly preferably, it has 6 to 12 carbon atoms, and examples thereof include phenyloxy and 2-naphthyloxy.), Acyl groups (preferably Or a carbon number of 1 to 16, more preferably a carbon number of 1 to 16, particularly preferably a carbon number of 1 to 12, such as acetyl, benzoyl, formyl, pivaloyl, etc.), an alkoxycarbonyl group (preferably carbon 2 to 20, more preferably 2 to 16 carbon atoms, particularly preferably 2 to 12 carbon atoms, such as methoxycarbonyl, ethoxycarbonyl, etc.), an aryloxycarbonyl group (preferably 7 to 20 carbon atoms). , More preferably 7 to 16 carbon atoms, particularly preferably 7 to 10 carbon atoms, such as phenyloxycarbonyl, etc.), an acyloxy group (preferably 2 to 20 carbon atoms, more preferably 2 to 2 carbon atoms). 16 and particularly preferably 2 to 10 carbon atoms, such as acetoxy and benzoyloxy. An acylamino group (preferably having 2 to 20 carbon atoms, more preferably 2 to 16 carbon atoms, particularly preferably 2 to 10 carbon atoms, and examples thereof include acetylamino and benzoylamino. ), An alkoxycarbonylamino group (preferably having 2 to 20 carbon atoms, more preferably 2 to 16 carbon atoms, particularly preferably 2 to 12 carbon atoms, such as methoxycarbonylamino), aryloxycarbonylamino A group (preferably having 7 to 20 carbon atoms, more preferably 7 to 16 carbon atoms, and particularly preferably 7 to 12 carbon atoms, such as phenyloxycarbonylamino), a sulfonylamino group (preferably having a carbon number) 1-20, more preferably 1-16 carbon atoms, particularly preferably 1-12 carbon atoms, such as methanesulfonylamino, benzenesulfonylamino, etc.), sulfamoyl groups (preferably 0-20 carbon atoms, More preferably, it has 0 to 16 carbon atoms, particularly preferably 0 to 12 carbon atoms. Moyl, methylsulfamoyl, dimethylsulfamoyl, phenylsulfamoyl, etc.), carbamoyl group (preferably having 1 to 20 carbon atoms, more preferably 1 to 16 carbon atoms, particularly preferably 1 to carbon atoms). For example, carbamoyl, methylcarbamoyl, diethylcarbamoyl, phenylcarbamoyl, etc.), an alkylthio group (preferably having 1 to 20 carbon atoms, more preferably 1 to 16 carbon atoms, and particularly preferably 1 to 12 carbon atoms). For example, methylthio, ethylthio, etc.), an arylthio group (preferably having 6-20 carbon atoms, more preferably 6-16 carbon atoms, particularly preferably 6-12 carbon atoms, such as phenylthio). ), A sulfonyl group (preferably having 1 to 20 carbon atoms, more preferably charcoal) 1 to 16, particularly preferably 1 to 12 carbon atoms, such as mesyl, tosyl, etc.), sulfinyl group (preferably 1 to 20 carbon atoms, more preferably 1 to 16 carbon atoms, particularly preferably C1-C12, for example, methanesulfinyl, benzenesulfinyl, etc.), ureido group (preferably C1-C20, more preferably C1-C16, particularly preferably C1-C12 Yes, for example, ureido, methylureido, phenylureido, etc.), phosphoric acid amide group (preferably having 1 to 20 carbon atoms, more preferably 1 to 16 carbon atoms, particularly preferably 1 to 12 carbon atoms, For example, diethyl phosphoric acid amide, phenyl phosphoric acid amide, etc.), hydroxy group, mercapto group, halogen atom (for example, fluorine source) Child, chlorine atom, bromine atom, iodine atom), cyano group, sulfo group, carboxyl group, nitro group, hydroxamic acid group, sulfino group, hydrazino group, imino group, heterocyclic group (preferably having 1 to 30 carbon atoms) Preferably, it has 1 to 12 carbon atoms, and the hetero atom includes, for example, a nitrogen atom, an oxygen atom, and a sulfur atom. Specifically, for example, imidazolyl, pyridyl, quinolyl, furyl, thienyl, piperidyl, morpholino, benzoxa Examples include zolyl, benzimidazolyl, benzothiazolyl, carbazolyl, azepinyl and the like. ), A silyl group (preferably having 3 to 40 carbon atoms, more preferably 3 to 30 carbon atoms, particularly preferably 3 to 24 carbon atoms, and examples thereof include trimethylsilyl and triphenylsilyl). . These substituents may be further substituted. When there are two or more substituents, they may be the same or different. If possible, they may be linked to each other to form a ring. In addition, _a plurality of betaine structures may be contained via R _a1 , R _a2 , R _a3 or _La .

In betaine compound for use in the present invention, at least one of R _a1, R _a2, R _a3 and L _a, it is preferable to contain the group having 8 or more carbon atoms. Of these, those in which a long chain alkyl group is contained in R _a1 , R _a2 or R _a3 are particularly preferable.

  General formula (2A-2):

(R _a ) _p1 -N- [L _a- (COOM _a ¹ ) _q ] _r1

In the formula _{(2A-2), R a} , L a, and q are as defined R _a, L _a, and q in the general formula (2A).
M _a ¹ is an alkali metal ion or a hydrogen atom.
p1 represents an integer of 0 or more and 2 or less, and r1 represents an integer of 1 or more and 3 or less. However, p1 + r1 is 3.
When p1 is 2 or more, R _a may be the same or different.

  General formula (2A) and general formula (2A-2) are demonstrated below.

In general formula (2A) and general formula (2A-2), each R _a is independently a hydrogen atom or a substituted or unsubstituted alkyl group (preferably a group having 1 to 20 carbon atoms. For example, a methyl group, An ethyl group, a propyl group, a butyl group, a hexyl group, an octyl group, a dodecyl group, a cetyl group, a stearyl group, an oleyl group, and the like, or a substituted or unsubstituted aryl group (preferably a group having 6 to 20 carbon atoms). A phenyl group, a tolyl group, a xylyl group, a naphthyl group, a cumyl group, a dodecylphenyl group, etc.), a substituted or unsubstituted heterocyclic group (preferably a group having 2 to 20 carbon atoms, such as a pyridyl group, a quinolyl group). Each of which may be connected to each other to form a ring structure. Among these, a substituted or unsubstituted alkyl group is particularly preferable.

L _a represents a divalent or higher linking group. As this example, a divalent or higher valent linking group containing an alkylene group, an arylene group or the like as a basic structural unit is preferable. You may contain hetero atoms, such as an oxygen atom, a sulfur atom, and a nitrogen atom, in a connection main chain part.
The preferred L _a, a substituted or unsubstituted alkylene group having 1 to 18 carbon atoms, more preferably an unsubstituted alkylene group having 1 to 8 carbon atoms, particularly preferably methylene group or ethylene group, .

The R _a and L _a may have various substituents. The substituent which may be R _a and _{L a} have, include substituents which may be possessed by _{R a1, R a2, R a3} and L _a in the above general formula (2A-1), preferred examples Is the same.
Further, through the R _a or L _a, betaine structures may be contained plural.

M _a represents a hydrogen atom, an alkali metal cation (for example, sodium ion, potassium ion, lithium ion, cesium ion), an ammonium ion, or an aminic organic cation (in the case of a primary to tertiary amine, a protonated one). Protonated methylamine, dimethylamine, ethylamine, diethylamine, triethylamine, diazabicycloundecene, diazabicyclooctane, piperidine, pyrrolidine, morpholine, N-methylpiperidine, N-methylmorpholine, pyridine, pyrazine, aniline, N N-dimethylaniline, etc. In the case of a quaternary ammonium salt, for example, tetramethylammonium ion, tetraethylmonium ion, trimethylbenzylammonium ion, methylpyridinium ion, Lupi lysine ions or the like.) Represents the. Of these, alkali metal ions or hydrogen atoms are particularly preferred.

q represents an integer of 1 or more (preferably 1 or more and 5 or less, more preferably 1 or 2), and r represents an integer of 1 or more and 4 or less (preferably 1 or 2). p represents an integer of 0 or more and 4 or less (preferably 1 or 2), and p + r is 3 or 4.
When p + r is 4, the N atom becomes a quaternary ammonium cation, and one of M _a becomes _a dissociated anion. When q is 2 or more, COOM _a may be the same or different. When r is 2 or more, L _a- (COOM _a ) _q may be the same or different. When p is 2 or more, R _a may be the same or different.
p1 represents an integer of 0 or more and 2 or less, and r1 represents an integer of 1 or more and 3 or less. However, p1 + r1 is 3. When p1 is 2 or more, R _a may be the same or different.

In addition, there may be mentioned embodiment be included in R _a or L _a is a hydrocarbon group having 8 or more carbon atoms, the compound represented by the following formula (2A-3) can also be used.

  General formula (2A-3):

R _a —N— (L _a —COOM _a ¹ ) ₂

In the formula _{(2A-3), R a} , L a and _M ^{a 1} is the same as _{R a, L} a and _M ^{a 1} in the foregoing general formula (2A-2). Two (L _a -COOM _a ¹ ) may be the same or different (two, L _a and M _a ¹ may be the same or different). R _a is alkyl group is particularly preferred, it is preferred that L _a is an alkylene group.

  Preferred examples of the betaine compound are listed below, but the present invention is not limited thereto.

  Among the above specific examples, the compound (2-3) is preferable.

[Defoaming agent]
The ink composition of the present invention contains an antifoaming agent.
Antifoaming agents that can be used in the present invention include silicone-based antifoaming agents, acetylenic diol-based antifoaming agents, polyoxyalkylene alkyl ether-based antifoaming agents, alkanediol-based antifoaming agents, polyether polyol-based antifoaming agents, Examples include ether-based antifoaming agents, alkylene oxide-based antifoaming agents, foam-breaking polymer-based antifoaming agents, and fatty acid ester-based antifoaming agents. These may be used individually by 1 type and may use 2 or more types together.

  Examples of the silicone-based antifoaming agent include KS508, KS531, KM72, and KM85 manufactured by Shin-Etsu Chemical Co., Ltd., Q-23183A and SH5510 manufactured by Toray Dow Corning Co., Ltd., SAG30 manufactured by Nihon Unicar Co., Ltd., etc. BYK-019, BYK-020, BYK-025, BYK-080A, BYK-094, BYK-1650, BYK-1660, manufactured by BYK Chemie Japan, KF-6701 manufactured by Shin-Etsu Silicone Co., Ltd. Is mentioned.

  As said acetylene diol type | system | group antifoamer, the compound represented by following General formula (3) is mentioned, for example.

In general formula (3), R ³¹ and R ³² each independently represent a hydrogen atom, a substituted or unsubstituted aliphatic group, or a substituted or unsubstituted aromatic group.
Examples of the aliphatic group for R ³¹ and R ³² include a linear, branched or cyclic alkyl group, a linear, branched or cyclic alkenyl group, a halogenated alkyl group, — (R ³¹¹ ) n—OH, an acryloyl group, A methacryloyl group is mentioned. R ³¹¹ represents an epoxy group or an alkyleneoxy group, and n represents an integer of 2 to 20.

The alkyl group is preferably an alkyl group having 1 to 12 carbon atoms, and specific examples include a methyl group, an ethyl group, an isopropyl group, a t-butyl group, a hexyl group, and a dodecyl group.
The halogenated alkyl group is preferably a halogenated alkyl group having 2 to 12 carbon atoms, and examples of the alkyl group moiety include the alkyl groups described above. Preferred halogen species include fluorine and chlorine.
The alkenyl group is preferably an alkenyl group having 1 to 12 carbon atoms, and specific examples include a vinyl group, a propenyl group, and a butenyl group.
The alkyleneoxy group for R ³¹¹ is preferably an alkyleneoxy group having 2 to 3 carbon atoms, and specific examples include an ethyleneoxy group and a propyleneoxy group.

Examples of the aromatic group for R ³¹ and R ³² include an aryl group, an aromatic heterocyclic group, and a condensed ring group thereof.
The aryl group is preferably an aryl group having 6 to 12 carbon atoms, and specific examples include a phenyl group and a naphthyl group.
The aromatic heterocyclic group is preferably an aromatic heterocyclic group having 5 to 12 carbon atoms. Specific examples of the hetero ring include an imidazoline ring, a pyrazole ring, an oxazoline ring, a pyridine ring, a pyrimidine ring, and a triazine ring. Is mentioned.

Examples of the substituent when R ³¹ and R ³² have a substituent include an alkyl group, an alkenyl group, a halogenated alkyl group, a halogen atom, an acryloyl group, a methacryloyl group, an epoxy group, an aryl group, and an aromatic heterocyclic group. Can be mentioned.
The alkyl group is preferably an alkyl group having 1 to 12 carbon atoms, and specific examples include a methyl group, an ethyl group, an isopropyl group, a t-butyl group, a hexyl group, and a dodecyl group.
The alkenyl group is preferably an alkenyl group having 1 to 12 carbon atoms, and specific examples include a vinyl group, a propenyl group, and a butenyl group.
The halogenated alkyl group is preferably a halogenated alkyl group having 2 to 12 carbon atoms, and examples of the alkyl group moiety include the alkyl groups described above. Preferred halogen species include fluorine and chlorine.
Examples of the halogen atom include fluorine and chlorine.

The aryl group is preferably an aryl group having 6 to 12 carbon atoms, and specific examples include a phenyl group and a naphthyl group.
The aromatic heterocyclic group is preferably an aromatic heterocyclic group having 5 to 12 carbon atoms. Specific examples of the hetero ring include an imidazoline ring, a pyrazole ring, an oxazoline ring, a pyridine ring, a pyrimidine ring, and a triazine ring. Is mentioned.

  Examples of the acetylenic diol antifoaming agent include Olfin SPC manufactured by Nissin Chemical Industry Co., Ltd., Surfynol 465, Surfynol DF110D, Surfynol MD20 manufactured by Air Products Japan.

  Examples of the polyoxyalkylene alkyl ether antifoaming agent include compounds represented by the following general formula (4).

In the general formula (4), R ₄₁ represents a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, and R ₄₂ represents a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 5 carbon atoms. Represents a group, and t represents an integer of 1 to 100.

Examples of the alkyl group having 1 to 20 carbon atoms R ₄₁ represents preferably an alkyl group having 10 to 20 carbon atoms, more preferably an alkyl group having 12 to 14 carbon atoms.
Examples of the alkyl group having 1 to 5 carbon atoms R ₄₂ represents preferably an alkyl group having 1 to 3 carbon atoms, more preferably a methyl group.
t represents an integer of 1 to 100, more preferably an integer of 10 to 20.

  Examples of the alkanediol antifoaming agent include Envirogem AD01 manufactured by Air Products Japan.

Examples of the polyether polyol antifoaming agent include Anti-Floss F-233 and Anti-Floss F-244 manufactured by Daiichi Kogyo Seiyaku.
Examples of the polyether antifoaming agent include SN deformer 375 manufactured by San Nopco.
Examples of the alkylene oxide antifoaming agent include Neugen LF-202N manufactured by Daiichi Kogyo Seiyaku.

  Examples of the foam-breaking polymer-based antifoaming agent include BYK-012 manufactured by BYK Japan, StarFactant 20 manufactured by Cognis Japan, and the like.

  As said antifoamer, the compound represented by the said General formula (3), the compound represented by the said General formula (4), or a silicone type antifoamer is preferable.

  Examples of the compound represented by the general formula (3) include Surfynol MD20, Surfynol DF110D, Surfynol 465 manufactured by Air Products Japan. In particular, Surfynol MD20 manufactured by Air Products Japan is preferable.

  Examples of the compound represented by the general formula (4) include Neugen LF60-X, Neugen LF80-X, Neugen LF100-X, Anti-Floss M-7, and Anti-Floss M-9 manufactured by Daiichi Kogyo Seiyaku. In particular, Anti-Floss M-7 manufactured by Daiichi Kogyo Seiyaku is preferred.

  As the silicone-based antifoaming agent, KF-6701 manufactured by Shin-Etsu Silicone is preferred.

  Further, as the antifoaming agent that can be used in the present invention, a silicone-based antifoaming agent, an acetylenic diol-based antifoaming agent, and a polyoxyalkylene alkyl ether-based antifoaming agent are preferable from the viewpoint of foamability and defoaming property, More preferred are diol-based antifoaming agents and polyoxyalkylene alkyl ether-based antifoaming agents.

[Ink composition]
The ink composition of the present invention contains a compound represented by the general formula (1), a compound represented by the general formula (2A), and an antifoaming agent. The ink composition of the present invention can contain a medium, but when a solvent is used as the medium, it is particularly suitable as an ink for inkjet recording. The ink composition of the present invention is prepared by using a lipophilic medium or an aqueous medium as a medium, and dissolving and / or dispersing the compound represented by the general formula (1) and the above components therein. can do. Preferably, an aqueous medium is used.

  In the present invention, the content of the compound represented by the general formula (1) of the present invention contained in the ink composition is the kind of the substituent in the general formula (1) used and the ink composition is produced. The content of the compound represented by the general formula (1) in the ink composition is 1 to 20% by mass with respect to the total mass of the ink composition. Preferably, it is contained in an amount of 1-10% by mass, more preferably 2-6% by mass.

  By setting the content of the compound represented by the general formula (1) contained in the ink composition to 1% by mass or more, it is possible to improve the print density of the ink on the recording medium when printed, and the necessity. Image density can be ensured. In addition, when the total amount of the compounds represented by the general formula (1) contained in the ink composition is 10% by mass or less, the ink composition can be excellently discharged when used in an ink jet recording method. In addition, it is possible to obtain an effect such that the inkjet nozzle is not easily clogged.

  In the present invention, the content of the betaine compound represented by the general formula (2A) contained in the ink composition is preferably 0.01 to 20% by mass with respect to the total mass of the ink composition. More preferably, it is contained in an amount of 1 to 10% by mass, and more preferably 0.5 to 5% by mass.

  In the present invention, the content of the antifoaming agent contained in the ink composition is preferably 0.01 to 3.0% by mass with respect to the total mass of the ink composition, and preferably 0.01 to 2.0. More preferably, it is contained by mass%.

  The ink composition of the present invention may contain other additives as necessary within a range that does not impair the effects of the present invention. Examples of other additives include additives that can be used in ink jet recording inks described later.

[Ink for inkjet recording]
Next, the ink for inkjet recording of the present invention will be described.
The ink for inkjet recording of the present invention contains the ink 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 component contained in the ink composition of the present invention in an oleophilic medium or an aqueous medium. The ink for inkjet recording is preferably an ink using an aqueous medium.
The ink for ink jet recording can contain other additives as required within a range that does not impair the effects of the present invention. Other additives include, for example, anti-drying agents (wetting agents), anti-fading agents, emulsion stabilizers, penetration enhancers, UV absorbers, preservatives, anti-fungal agents, pH adjusters, surface tension adjusters, viscosity Well-known additives, such as a regulator, a dispersing agent, a dispersion stabilizer, a rust inhibitor, a chelating agent, are mentioned. These various additives are directly added to the ink liquid in the case of water-soluble ink. When an oil-soluble dye is used in the form of a dispersion, it is generally added to the dispersion after the preparation of the dye dispersion, but it may be added to the oil phase or the aqueous phase at the time of preparation. Details of the additive are described in International Publication No. 2017/006939, which can be referred to in the present invention.

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 (E.g., ethylene glycol, diethylene glycol, triethylene glycol, polyethylene glycol, propylene glycol, dipropylene glycol, polypropylene glycol, butylene glycol, hexanediol, pentanediol, glycerin, hexanetriol, thiodiglycol), glycol derivatives (e.g., 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), amine (for example, ethanolamine, diethanolamine, triethanolamine, N-methyldiethanolamine, N-ethyldiethanolamine, morpholine, N-ethylmorpholine, ethylenediamine, diethylenetriamine, Reethylenetetramine, 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). Two or more types of water-miscible organic solvents may be used in combination.

In 100 parts by mass of the inkjet recording ink of the present invention, the compound represented by the general formula (1) is preferably contained in an amount of 0.2 to 10 parts by mass, and preferably 1 to 6 parts by mass. Is more preferable. In addition, in the inkjet recording ink of the present invention, other dyes may be used in combination with the compound represented by the general formula (1). When using 2 or more types of pigment | dyes together, it is preferable that the sum total of content of a pigment | dye is the said range.
The contents of the betaine compound and the antifoaming agent in the ink for inkjet recording are the same as the contents of the betaine compound and the antifoaming agent in the ink composition.

  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 are various additives such as viscosity modifiers, surface tension modifiers, specific resistance modifiers, film modifiers, UV absorbers, antioxidants, antifading agents, antifungal agents, and rust inhibitors. It can be adjusted by adding a dispersant and a surfactant.

  The ink for ink jet recording of the present invention can be used in various color tones, but is preferably used in a magenta color ink. Further, it can be used not only for forming a single color image but also for forming a full color image. In order to form a full color image, a magenta color ink, a cyan color ink, and a yellow color ink can be used, and a black color ink may be further used to adjust the color tone.

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

[Inkjet recording method]
The present invention also relates to an inkjet recording method for forming an image using the ink composition or the inkjet recording ink of the present invention.
In the ink jet recording method of the present invention, a known image receiving material, that is, plain paper, resin-coated paper, for example, JP-A-8-169172, JP-A-8-27693, and JP-A-2 JP-A-276670, JP-A-7-276789, JP-A-9-323475, JP-A-62-238783, JP-A-10-153789, JP-A-10-217473, JP-A-10-235995, Form images on inkjet paper, film, electrophotographic co-paper, fabric, glass, metal, ceramics, etc. described in JP-A-10-337947, JP-A-10-217597, and JP-A-10-337947 .

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

  EXAMPLES Hereinafter, although an Example is shown and this invention is demonstrated in detail, this invention is not limited to these Examples at all. Unless otherwise specified, “%” and “parts” in the examples are% by mass and parts by mass.

[Examples 1-50, Comparative Examples 1-6]
(Preparation of ink)
Deionized water was added to the following components to make 100 g, and the mixture was stirred for 1 hour while heating at 30 to 40 ° C. Thereafter, the pH was adjusted to 9 with a 10 mol / L sodium hydroxide aqueous solution, and the mixture was filtered under reduced pressure through a microfilter having an average pore size of 0.25 μm to prepare a magenta ink.
2.00 g of the dyes listed in Table 1
1.14 g of betaine compounds listed in Table 1
Antifoaming agents listed in Table 1 Amounts listed in Table 1 Glycerin 21.18 g
Triethylene glycol monobutyl ether 20.82g
2-pyrrolidone 4.80 g
Triethylene glycol 4.18g

<Foaming and antifoaming properties>
Foaming and defoaming were carried out by visual observation and observing the foam height over time. Specifically, 5 ml of the inks of the examples and comparative examples were sealed in a test tube container having a diameter of 1.5 cm and a height of 30 cm and shaken 30 times. From the interface between the bubbles and the liquid, the maximum height of the bubbles was The height until this time was measured to evaluate foaming properties, and the time until bubbles disappeared and the liquid level was seen was evaluated as defoaming properties. (The experiment was carried out at a temperature of 23-24 ° C.)

  For light resistance and moisture resistance, each magenta ink (inkjet recording ink) is loaded into an ink cartridge, and photo glossy paper (Seiko Epson Corporation) is printed with an inkjet printer (manufactured by Seiko Epson Corporation; PX-045A). Manufactured; photo paper (glossy)) and evaluated after recording the image.

<Light resistance>
After measuring the image density Ci immediately after recording, the image was irradiated with xenon light (100,000 lux) for 21 days using a weather meter (Atlas C.165), and then the image density Cf was measured again to obtain xenon light. The dye residual ratio (Cf / Ci × 100%) was calculated from the image density before and after irradiation and evaluated. The image density was measured using a reflection densitometer (X-Rite 310TR, trade name). The dye residual ratio was measured using an image portion having an initial image density of about 1.0 ± 0.2.
The optical density residual ratio (ROD) was obtained from the following formula and evaluated according to the following criteria.
ROD (%) = (D / D0) × 100
D: OD after exposure test D0: OD before exposure test
A: When ROD is 90% or more B: When ROD is 70% or more and less than 90% C: When ROD is 50% or more and less than 70% D: When ROD is less than 50%

<Moisture resistance>
For image bleeding under high humidity conditions, a print pattern in which a square pattern of 1 mm x 1 mm of magenta is arranged so as to form a white background gap of 0.5 mm so as to be 3 cm in length and width is prepared. Was observed for 7 days under conditions of 45 ° C. and 85% relative humidity. After observing bleeding of the magenta dye in the white space, the increase in white magenta density immediately after printing was less than 0.02 in the status A magenta filter. , 0.02 or more and less than 0.10 is B, 0.10 or more and less than 0.50 is C, and 0.50 or more is D.

  The results obtained are listed in Table 2.

  Compound (X-1) is C.I. I. Acid Red 289, and the compound (X-2) is C.I. I. It represents Acid Red 52.

  From the results shown in Table 2, it can be seen that the ink compositions of the present invention and the ink jet recording examples are satisfactory in light resistance, moisture resistance, foaming property and antifoaming property.

Claims (10)

An ink composition comprising a compound represented by the following general formula (1), a betaine compound represented by the following general formula (2A), and an antifoaming agent.

In general formula (1),
R ¹ , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁸ , R ⁹ , R ¹⁰ , R ¹¹ , R ¹² , R ¹³ , R ¹⁴ , R ¹⁵ , R ¹⁶ , R ¹⁷ , R ¹⁸ , R ¹⁹ And R ²⁰ each independently represents a hydrogen atom or a substituent, and X ¹ and X ² each independently represent a hydroxyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted group Heterocyclic oxy group, substituted or unsubstituted alkylamino group, substituted or unsubstituted arylamino group, substituted or unsubstituted heterylamino group, substituted carbonylamino group, substituted or unsubstituted acyloxy group, substituted or unsubstituted amino A carbonyloxy group, a substituted sulfonylamino group, a substituted or unsubstituted alkylthio group, or a substituted or unsubstituted arylthio group is represented. .
General formula (2A):
(R _a ) _p -N- [L _a- (COOM _a ) _q ] _r
In general formula (2A),
Each R _a independently represents a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group. L _a represents a divalent or higher linking group. M _a represents a hydrogen atom, an alkali metal atom, an ammonium group, a protonated organic amine or a nitrogen-containing heterocyclic group, or a quaternary ammonium ion group, and is a counter ion of an ammonium ion composed of an N atom in the formula. In the case, it represents a group that does not exist as a cation.
q represents an integer of 1 or more, and r represents an integer of 1 to 4. p represents an integer of 0 or more and 4 or less, and p + r is 3 or 4. When p + r is 4, the N atom is a protonated ammonium atom.
When q is 2 or more, the plurality of COOM _a may be the same or different. When r is 2 or more, L _a- (COOM _a ) _q may be the same or different. When p is 2 or more, the plurality of R _a may be the same or different. The ink composition according to claim 1, wherein the compound represented by the general formula (1) is a compound represented by the following general formula (1-1).

In general formula (1-1),
R ¹ , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁸ , R ⁹ , R ¹⁰ , R ¹¹ , R ¹² , R ¹³ , R ¹⁴ , R ¹⁵ , R ¹⁶ , R ¹⁷ , R ¹⁸ , R ¹⁹ And R ²⁰ each independently represents a hydrogen atom or a substituent, and R ¹⁰¹ and R ¹⁰² each independently represent a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted group Represents a carbonyl group or a substituted sulfonyl group. R ¹⁰¹ and R ¹⁰² are each independently a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted sulfonyl group, a substituted or unsubstituted alkoxycarbonyl group, substituted or unsubstituted Unsubstituted aryloxycarbonyl group, carbamoyl group, substituted or unsubstituted monoalkylaminocarbonyl group, substituted or unsubstituted dialkylaminocarbonyl group, substituted or unsubstituted monoarylaminocarbonyl group, substituted or unsubstituted diarylamino The ink composition according to claim 2, which represents a carbonyl group or a substituted or unsubstituted alkylarylaminocarbonyl group. The general ^R 1 in formula (1) or the general formula (1-1) ^in, R 5, ^{R 6,} and ^{R 10} represents an alkyl group having 1 to 6 carbon atoms each independently of claims 1 to 3 The ink composition according to any one of the above. The ink composition according to claim 1, wherein R ¹² and R ^{15 in the} general formula (1) or the general formula (1-1) each independently represent a sulfo group. The ink composition according to claim 1, wherein the betaine compound represented by the general formula (2A) is a compound represented by the following general formula (2A-1).

In the general formula (2A-1),
R _{a1 to} R _a3 each independently represents a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, and La represents _a divalent linking group. 7. The antifoaming agent according to claim 1, wherein the antifoaming agent is a compound represented by the following general formula (3), a compound represented by the following general formula (4), or a silicone-based antifoaming agent. Ink composition.

In the general formula (3), R ³¹ and R ³² each independently represent a hydrogen atom, a substituted or unsubstituted aliphatic group, or a substituted or unsubstituted aromatic group.

In the general formula (4),
R ₄₁ represents a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, R ₄₂ represents a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 5 carbon atoms, t is 1 to 1 An integer of 100 is represented.   The ink composition according to any one of claims 1 to 7, wherein a content of the betaine compound is 0.01 to 20% by mass with respect to a total mass of the ink composition.   The ink composition according to any one of claims 1 to 7, wherein a content of the antifoaming agent is 0.01 to 3.0 mass% with respect to a total mass of the ink composition. An ink jet recording method for forming an image using the ink composition according to claim 1.