JP2015193800A - Compound, coloring composition, ink for inkjet recording, inkjet recording method, inkjet printer cartridge, and inkjet recorded matter - Google Patents

Abstract

【選択図】なしA compound capable of forming an image excellent in light resistance, ozone resistance, and moisture resistance and excellent in storage stability of an ink, a coloring composition containing the compound, an ink for inkjet recording, and the ink Provided inkjet recording method and recorded matter.
In the compound represented by the general formula (1), D is a residue of the compound represented by the general formula (D).

[Selection figure] None

Description

  The present invention relates to a compound, a coloring composition containing the compound, an inkjet recording ink, an inkjet recording method, an inkjet printer cartridge, and an inkjet recorded matter.

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. .
When forming a color image using an inkjet recording method, it is common to use at least yellow ink, magenta ink, cyan ink, and black ink. These inks have physical properties such as viscosity and surface tension within an appropriate range, nozzle clogging, excellent storage stability, and a high density recording image, light resistance, ozone resistance, Properties such as excellent water resistance and moisture resistance are required.

  These performances often meet the required levels by using water or a water-based ink containing a mixture of water and a water-soluble organic solvent as a main solvent, but in particular, color tone, vividness, light resistance, Ozone resistance, water resistance, moisture resistance, and the like depend largely on the colorant, and various dyes have been studied in the past.

For example, Patent Document 1 describes a xanthene derivative substituted with an anilino group, and a compound in which an acylamino group is substituted for the anilino group, and an ink jet recorded material formed using a colored composition containing the compound The saturation, light resistance, ozone resistance, etc. are being studied.
Patent Document 2 describes a compound in which a specific substituent containing a triazine ring is bonded to a xanthene derivative substituted with an anilino group, and an image formed using a colored composition containing this compound is printed. It describes that it is excellent in concentration, ozone resistance, light resistance and moisture resistance.

JP 2011-148773 A JP 2013-49776 A

  However, in the field of dyes, further improvement in performance is required, and a compound that can further improve image fastness such as light resistance, ozone resistance, and moisture resistance and ink storage stability is required. Has been.

  An object of this invention is to provide the compound and coloring composition which can form the image excellent in light resistance, ozone resistance, and moisture resistance, and are excellent also in the storage stability of an ink. Another object of the present invention is to provide an ink jet recording ink containing the above compound and a coloring composition, an ink jet recording method using the ink for ink jet recording, an ink jet printer cartridge, and an ink jet recorded product.

As a result of intensive studies, the present inventors have found that the above problem can be solved by a compound represented by the following general formula (1).
The compound represented by the general formula (1) has an alkyl group at a specific position (ortho position with respect to the carbon atom bonded to the nitrogen atom) of the anilino group of the xanthene derivative substituted with the anilino group, and has a specific A compound having an acylamino group at a position (meta position with respect to a carbon atom bonded to a nitrogen atom) and a group containing a triazine ring. Although the mechanism of action is unknown, it is considered that the compound has an acylamino group at the meta position with respect to the carbon atom bonded to the nitrogen atom of the anilino group, thereby exhibiting excellent light resistance and ozone resistance. Further, it is considered that moisture resistance is improved by having a group containing a triazine ring due to interaction with a printing medium by hydrogen bonding. Furthermore, although the mechanism of action is unknown, the presence of the acylamino group and the group containing a triazine ring suppresses the formation of a decomposition product of the compound in the ink for ink jet recording containing this compound, thereby improving the storage stability. It is considered a thing.
That is, the present invention is as follows.

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

In general formula (1), D represents a residue obtained by removing n hydrogen atoms from a compound represented by the following general formula (D), L represents a single bond or a divalent linking group, and R ^a represents A hydrogen atom or a substituent is represented, and R ^b and R ^c each independently represent a substituent. n represents an integer of 1 to 4.
Formula (D)

In general formula (D), R ¹ , R ⁵ , R ⁶ and R ¹⁰ each independently represents a substituted or unsubstituted alkyl group. R ³ , R ⁴ , R ⁸ , R ⁹ , R ¹¹¹ , R ¹¹² , R ¹¹³ , R ¹¹⁴ , R ¹¹⁵ , R ¹¹⁶ , R ¹¹⁷ , R ¹¹⁸ , R ¹¹⁹ and R ¹²⁰ are each independently a hydrogen atom or a substituent. Represents. R ¹⁰¹ and R ¹⁰² each independently represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group. R ¹⁰³ and R ¹⁰⁴ each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group.
[2]
The compound according to [1], wherein D is a residue obtained by removing a hydrogen atom from at least one of R ¹⁰¹ and R ^{102 in} the general formula (D).
[3]
The compound according to [1], wherein D is a residue obtained by removing a hydrogen atom from at least one of R ⁴ and R ^{9 in} the general formula (D).
[4]
The compound according to any one of [1] to [3], wherein L is represented by the following general formula (L1) or (L2).
General formula (L1)

In General Formula (L1), R ¹¹ represents a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. L ¹¹ represents a substituted or unsubstituted alkylene group.
General formula (L2)

In General Formula (L2), R ²¹ represents a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. L ²¹ represents a substituted or unsubstituted alkylene group.
[5]
[1] The compound according to any one of [1] to [4], wherein n represents 1 or 2.
[6]
The compound according to [1], [2] or [4], wherein the compound represented by the general formula (1) is represented by the following general formula (2).
General formula (2)

In General Formula (2), L ² each independently represents a single bond or a divalent linking group, R ^a represents ^a hydrogen atom or a substituent, and R ^b and R ^c each independently represent a substituent. R ¹ , R ⁵ , R ⁶ and R ¹⁰ each independently represents a substituted or unsubstituted alkyl group. R ³ , R ⁴ , R ⁸ , R ⁹ , R ¹¹¹ , R ¹¹² , R ¹¹³ , R ¹¹⁴ , R ¹¹⁵ , R ¹¹⁶ , R ¹¹⁷ , R ¹¹⁸ , R ¹¹⁹ and R ¹²⁰ are each independently a hydrogen atom or a substituent. Represents. R ¹⁰³ and R ¹⁰⁴ each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group.
[7]
The compound according to [1], [3] or [5], wherein the compound represented by the general formula (1) is represented by the following general formula (3).
General formula (3)

In General Formula (3), L ³ represents a single bond or a divalent linking group, R ^a represents ^a hydrogen atom or a substituent, and R ^b and R ^c each independently represent a substituent. R ¹ , R ⁵ , R ⁶ and R ¹⁰ each independently represents a substituted or unsubstituted alkyl group. R ³ , R ⁴ , R ⁸ , R ¹¹¹ , R ¹¹² , R ¹¹³ , R ¹¹⁴ , R ¹¹⁵ , R ¹¹⁶ , R ¹¹⁷ , R ¹¹⁸ , R ¹¹⁹ and R ¹²⁰ each independently represent a hydrogen atom or a substituent. R ¹⁰¹ and R ¹⁰² each independently represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group. R ¹⁰³ and R ¹⁰⁴ each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group.
[8]
The compound according to [1], [3] or [5], wherein the compound represented by the general formula (1) is represented by the following general formula (4).
General formula (4)

In General Formula (4), L ⁴ each independently represents a single bond or a divalent linking group, R ^a represents ^a hydrogen atom or a substituent, and R ^b and R ^c each independently represent a substituent. R ¹ , R ⁵ , R ⁶ and R ¹⁰ each independently represents a substituted or unsubstituted alkyl group. R ³ , R ⁸ , R ¹¹¹ , R ¹¹² , R ¹¹³ , R ¹¹⁴ , R ¹¹⁵ , R ¹¹⁶ , R ¹¹⁷ , R ¹¹⁸ , R ¹¹⁹ and R ¹²⁰ each independently represent a hydrogen atom or a substituent. R ¹⁰¹ and R ¹⁰² each independently represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group. R ¹⁰³ and R ¹⁰⁴ each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group.
[9]
The compound according to [1], [3] or [5], wherein the compound represented by the general formula (1) is represented by the following general formula (5).
General formula (5)

In General Formula (5), L ⁵ each independently represents a single bond or a divalent linking group, R ^a represents ^a hydrogen atom or a substituent, and R ^b and R ^c each independently represent a substituent. R ¹ , R ⁵ , R ⁶ and R ¹⁰ each independently represents a substituted or unsubstituted alkyl group. R ³ , R ⁴ , R ⁸ , R ⁹ , R ¹¹¹ , R ¹¹² , R ¹¹³ , R ¹¹⁴ , R ¹¹⁶ , R ¹¹⁷ , R ¹¹⁸ , R ¹¹⁹ and R ¹²⁰ each independently represent a hydrogen atom or a substituent. R ¹⁰¹ and R ¹⁰² each independently represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group. R ¹⁰³ and R ¹⁰⁴ each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group.
[10]
The compound according to [1], [3] or [5], wherein the compound represented by the general formula (1) is represented by the following general formula (6).
General formula (6)

In General Formula (6), L ⁶ each independently represents a single bond or a divalent linking group, R ^a represents ^a hydrogen atom or a substituent, and R ^b and R ^c each independently represent a substituent. R ¹ , R ⁵ , R ⁶ and R ¹⁰ each independently represents a substituted or unsubstituted alkyl group. R ³ , R ⁴ , R ⁸ , R ⁹ , R ¹¹¹ , R ¹¹³ , R ¹¹⁴ , R ¹¹⁶ , R ¹¹⁷ , R ¹¹⁸ , R ¹¹⁹ and R ¹²⁰ each independently represent a hydrogen atom or a substituent. R ¹⁰¹ and R ¹⁰² each independently represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group. R ¹⁰³ and R ¹⁰⁴ each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group.
[11]
The compound according to [6], wherein L ² is represented by the following general formula (L3).
General formula (L3)

In General Formula (L3), R ³¹ represents a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. L ³¹ and L ³² each independently represents a substituted or unsubstituted alkylene group.
[12]
The compound according to [7], [8], [9] or [10], wherein each of L ³ , L ⁴ , L ⁵ or L ⁶ is independently represented by the following general formula (L4).
General formula (L4)

In General Formula (L4), R ⁴¹ represents a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. L ⁴¹ represents a substituted or unsubstituted alkylene group.
[13]
A coloring composition containing the compound according to any one of [1] to [12].
[14]
[1] An ink for ink jet recording containing the compound according to any one of [12].
[15]
An inkjet recording method using the inkjet recording ink according to [14].
[16]
[14] An ink jet printer cartridge filled with the ink for ink jet recording described in [14].
[17]
[14] An ink-jet recorded matter in which a colored image is formed on a recording material using the ink for ink-jet recording described in [14].

  The compound of the present invention can be suitably used for a coloring composition and an ink for inkjet recording, and is excellent in storage stability of the ink. The coloring composition and the ink for inkjet recording of the present invention can form an image excellent in light resistance, ozone resistance, and moisture resistance. In addition, according to the present invention, there are provided an ink jet recording method, an ink jet printer cartridge, and an ink jet recorded matter using the above ink jet recording ink.

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

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

  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, branched, and cyclic substituted or unsubstituted alkyl groups, and include cycloalkyl groups, bicycloalkyl groups, and tricyclo structures having many ring structures. An alkyl group (for example, an alkyl group of an alkoxy group or an alkylthio group) in a substituent described below also represents such an alkyl group.
As the alkyl group, an alkyl group having 1 to 30 carbon atoms such as a methyl group, an ethyl group, an n-propyl group, an i-propyl group, a t-butyl group, an n-octyl group, an eicosyl group, 2- Examples thereof include a chloroethyl group, a 2-cyanoethyl group, a 2-ethylhexyl group, etc. The cycloalkyl group is preferably a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, such as a cyclohexyl group, a cyclopentyl group, 4 -N-dodecylcyclohexyl group and the like, and the bicycloalkyl group is preferably a substituted or unsubstituted bicycloalkyl group having 5 to 30 carbon atoms, that is, one hydrogen atom from a bicycloalkane having 5 to 30 carbon atoms. Removed monovalent groups such as bicyclo [1,2,2] heptan-2-yl group, bicyclo [2,2 2] octan-3-yl group.

  Examples of the aralkyl group include a substituted or unsubstituted aralkyl group, and the substituted or unsubstituted aralkyl group is preferably an aralkyl group having 7 to 30 carbon atoms. 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 carboxyl group, phosphono group and sulfo group may be in the form of a salt. Examples of counter cations that form a salt include ammonium ion, alkali metal ion (eg, lithium ion, sodium ion, potassium ion) and organic. Cation (eg, tetramethylammonium ion, tetramethylguanidinium ion, tetramethylphosphonium) is included, lithium salt, sodium salt, potassium salt, ammonium salt is preferable, sodium salt or mixed salt containing sodium salt as main component Are more preferred, and the sodium salt is most preferred.

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

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

In general formula (1), D represents a residue obtained by removing n hydrogen atoms from a compound represented by the following general formula (D), L represents a single bond or a divalent linking group, and R ^a represents A hydrogen atom or a substituent is represented, and R ^b and R ^c each independently represent a substituent. n represents an integer of 1 to 4.
Formula (D)

In general formula (D), R ¹ , R ⁵ , R ⁶ and R ¹⁰ each independently represents a substituted or unsubstituted alkyl group. R ³ , R ⁴ , R ⁸ , R ⁹ , R ¹¹¹ , R ¹¹² , R ¹¹³ , R ¹¹⁴ , R ¹¹⁵ , R ¹¹⁶ , R ¹¹⁷ , R ¹¹⁸ , R ¹¹⁹ and R ¹²⁰ are each independently a hydrogen atom or a substituent. Represents. R ¹⁰¹ and R ¹⁰² each independently represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group. R ¹⁰³ and R ¹⁰⁴ each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group.

In general formula (1), R ^a represents a hydrogen atom or a substituent. When R ^a represents a substituent, examples of the substituent include a substituted or unsubstituted alkyl group and a substituted or unsubstituted aryl group. The alkyl group is preferably an alkyl group having 1 to 6 carbon atoms, 1 to 3 alkyl groups are more preferable, and a methyl group is still more preferable. As the aryl group, an aryl group having 6 to 20 carbon atoms is preferable, an aryl group having 6 to 12 carbon atoms is more preferable, and a phenyl group is still more preferable. In addition, examples of the substituent in the case where the alkyl group or aryl group has a substituent include a substituent selected from the above substituent group A, and a chlorine atom is preferable.
R ^a preferably represents ^a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group, more preferably represents a hydrogen atom or a substituted or unsubstituted alkyl group, and represents a hydrogen atom. Is more preferable. In addition, examples of the substituent in the case where the alkyl group or aryl group has a substituent include a substituent selected from the above substituent group A, and a chlorine atom is preferable.

In general formula (1), R ^b and R ^c each independently represent a substituent. Examples of the substituent represented by R ^b and R ^c include a substituent selected from the above substituent group A, and include a substituted or unsubstituted amino group, a hydroxyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted group. An aryloxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted arylthio group, and a substituted or unsubstituted heterocyclic thio group are preferred, and a substituted or unsubstituted amino group is more preferred.
Examples of the substituent when the substituent represented by R ^b and R ^c further has a substituent include the substituent selected from the above substituent group A, and an alkyl group, an aryl group, or a heterocyclic group is preferable. . These may be further substituted with a substituent selected from Substituent Group A, and more preferably substituted with an ionic hydrophilic group.
R ^b and R ^c are particularly preferably an amino group, a morpholino group, a substituted or unsubstituted alkylamino group, or a substituted or unsubstituted arylamino group. The alkylamino group is preferably an alkylamino group having 1 to 6 carbon atoms, more preferably an alkylamino group having 1 to 3 carbon atoms, and still more preferably an ethylamino group. As the arylamino group, an arylamino group having 6 to 20 carbon atoms is preferable, an arylamino group having 6 to 12 carbon atoms is more preferable, and a phenylamino group is still more preferable. In addition, as the substituent when the alkylamino group or arylamino group has a substituent, an ionic hydrophilic group is preferable, a carboxyl group, a sulfo group, or a phosphono group is more preferable, and a carboxyl group or a sulfo group is still more preferable. Examples of the counter cation of these ionic hydrophilic groups include a hydrogen atom (proton), an alkali metal cation (lithium ion, sodium ion, or potassium ion), an ammonium ion, and the like, and is preferably an alkali metal cation. More preferred is sodium ion.

  In general formula (1), n represents an integer of 1 to 4, and preferably represents 1 or 2.

In general formula (1), L represents a single bond or a divalent linking group, and examples of the divalent linking group include an oxy group (—O—), a thio group (—S—), a carbonyl group (—CO—). ), A sulfonyl group (—SO ₂ —), an imino group (—NH—), an alkylene group (preferably an alkylene group having 1 to 10 carbon atoms, more preferably an alkylene group having 2 to 6 carbon atoms), an arylene group (preferably Is an arylene group having 6 to 20 carbon atoms, more preferably an arylene group having 6 to 10 carbon atoms), and a group formed by combining these. These groups may have a substituent, and examples of the substituent include a substituent selected from Substituent Group A, and an alkyl group is preferable.
L is preferably an alkylene group having 1 to 10 carbon atoms which may have a substituent, or an arylene group having 6 to 10 carbon atoms which may have a substituent, more preferably a substituent. It is a C1-C10 alkylene group which may have, More preferably, it is a C2-C6 alkylene group which may have a substituent.
L is preferably represented by the following general formula (L1) or (L2).
General formula (L1)

In General Formula (L1), R ¹¹ represents a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. L ¹¹ represents a substituted or unsubstituted alkylene group.
General formula (L2)

In General Formula (L2), R ²¹ represents a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. L ²¹ represents a substituted or unsubstituted alkylene group.

In General Formula (L1), R ¹¹ represents a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group.
The alkyl groups which may R ¹¹ represents an alkyl group, preferably an alkyl group having 1 to 6 carbon atoms, more preferably an alkyl group having 1 to 3 carbon atoms, more preferably methyl group. Moreover, as a substituent in case an alkyl group has a substituent, the substituent chosen from the said substituent group A is mentioned, A chlorine atom is preferable.
As the aryl group when R ¹¹ represents an aryl group, an aryl group having 6 to 20 carbon atoms is preferable, an aryl group having 6 to 12 carbon atoms is more preferable, and a phenyl group is still more preferable. Moreover, as a substituent in case an aryl group has a substituent, the substituent chosen from the said substituent group A is mentioned, A chlorine atom is preferable.
R ¹¹ preferably represents a hydrogen atom or a substituted or unsubstituted alkyl group, and more preferably represents a hydrogen atom.

In general formula (L1), L ¹¹ represents a substituted or unsubstituted alkylene group, preferably an optionally substituted alkylene group having 1 to 10 carbon atoms, and has a substituent. It is more preferable to represent an alkylene group having 2 to 6 carbon atoms, and it is most preferable to represent an ethylene group. Examples of the substituent when the alkylene group has a substituent include a substituent selected from the above substituent group A, and a chlorine atom is preferable.

In the general formula (L2), R ²¹ and L ²¹ have the same meanings as R ¹¹ and L ¹¹ in the general formula (L1), and specific examples and preferred ranges thereof are also the same.

The carbon atom of the carbonyl group in the general formula (L1) or the sulfur atom of the sulfonyl group in the general formula (L2) and D in the general formula (1) are bonded to each other, so that L ¹¹ in the general formula (L1) or the general formula ( it is preferable that N in L2) ^{L 21} and the general formula in (1) binds.

In general formula (1), D represents a residue obtained by removing n hydrogen atoms from the compound represented by general formula (D).
In general formula (D), R ¹ , R ⁵ , R ⁶ and R ¹⁰ each independently represent a substituted or unsubstituted alkyl group. From the viewpoint of availability of raw materials and ease of synthesis, A C1-C6 alkyl group is preferable, a C1-C3 alkyl group is more preferable, and a methyl 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, A chlorine atom is preferable.

In the general formula (D), R ³ , R ⁴ , R ⁸ , R ⁹ , R ¹¹¹ , R ¹¹² , R ¹¹³ , R ¹¹⁴ , R ¹¹⁵ , R ¹¹⁶ , R ¹¹⁷ , R ¹¹⁸ , R ¹¹⁹ and R ¹²⁰ are each Independently represents a hydrogen atom or a substituent, and examples of the substituent include a substituent selected from the substituent group A.

In general formula (D), R ⁴ and R ⁹ 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, light resistance, and ozone resistance. 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 an unsubstituted alkylsulfonylamino 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. Preferably, more preferably a hydrogen atom, a 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 sulfo Group, particularly preferably a hydrogen atom or a sulfo group. Moreover, as a substituent in case each group has a substituent, the substituent chosen from the said substituent group A is mentioned, A chlorine atom is preferable.

In general formula (D), 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, as a substituent in case each group has a substituent, the substituent chosen from the said substituent group A is mentioned, A chlorine atom is preferable.

In general formula (D), R ¹¹¹ , R ¹¹³ , R ¹¹⁴ , R ¹¹⁶ , R ¹¹⁷ , R ¹¹⁸ , R ¹¹⁹ and R ¹²⁰ are each independently a hydrogen atom from the viewpoint of availability of raw materials and ease of synthesis. Substituted or unsubstituted 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 Preferably represents a carboxyl group or a halogen atom, more Mashiku is a hydrogen atom, a substituted or unsubstituted alkyl group, or a sulfo group, particularly preferably a hydrogen atom or 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, as a substituent in case each group has a substituent, the substituent chosen from the said substituent group A is mentioned, A chlorine atom is preferable.

In the general formula (D), R ¹¹² and R ¹¹⁵ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted group, from the viewpoint of availability of raw materials and ease of synthesis, light resistance, and ozone resistance. 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 an unsubstituted alkylsulfonylamino 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. Preferably, more preferably a hydrogen atom, a substituted or unsubstituted acyl group 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, as a substituent in case each group has a substituent, the substituent chosen from the said substituent group A is mentioned, A chlorine atom is preferable.

From the viewpoint of solubility, R ¹ , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁸ , R ⁹ , R ¹⁰ , R ¹¹¹ , R ¹¹² , R ¹¹³ , R in general formula (D) ¹¹⁴ , R ¹¹⁵ , R ¹¹⁶ , R ¹¹⁷ , R ¹¹⁸ , R ¹¹⁹ and R ¹²⁰ , or at least one of the substituents of R ¹⁰¹ , R ¹⁰² , R ¹⁰³ and R ¹⁰⁴ is a carboxyl group, a sulfo group, Alternatively, it preferably has an ionic hydrophilic group such as a phosphono group. Examples of the counter cation of these ionic hydrophilic groups include a hydrogen atom (proton), an alkali metal cation (lithium ion, sodium ion, or potassium ion), an ammonium ion, and the like, but easy synthesis (as dye powder) From the viewpoint of ease of handling, it is preferably an alkali metal cation.

In General Formula (D), R ¹⁰¹ and R ¹⁰² each independently represent a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.

The alkyl group in the case where R ¹⁰¹ and R ¹⁰² represent an alkyl group is preferably an alkyl group having 1 to 25 carbon atoms, more preferably an alkyl group having 1 to 18 carbon atoms, and further an alkyl group having 1 to 8 carbon atoms. preferable. Examples of the alkyl group include linear, branched or cyclic alkyl groups, and specifically, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group. , T-butyl group, cyclohexyl group and 2-ethylhexyl group are preferable, and methyl group, ethyl group, isopropyl group and cyclohexyl group are more preferable. The alkyl group may have a substituent, and examples of the substituent include a substituent selected from the above substituent group A, and chlorine is preferred.

When R ¹⁰¹ and R ¹⁰² represent an 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. Specific examples of the aryl group include a phenyl group, a naphthyl group, and an anthracenyl group, and a phenyl group is preferable. The aryl group may have a substituent, and examples of the substituent include a substituent selected from the above substituent group A, and a chlorine atom is preferable.

When R ¹⁰¹ and R ¹⁰² represent a heterocyclic group, the heterocyclic group is preferably an aromatic heterocyclic group, more preferably a 5-membered or 6-membered aromatic heterocyclic group having a nitrogen atom, a sulfur atom or an oxygen atom. preferable. As the heterocyclic group, if the substitution position is not limited, pyrrole ring, pyrazole ring, imidazole ring, triazole ring, thiophene ring, thiazole ring, isothiazole ring, thiadiazole ring, pyridine ring, pyrazine ring, pyrimidine ring, triazine A ring etc. are mentioned preferably, A pyridine ring and a thiazole ring are more preferable. The 5-membered or 6-membered aromatic heterocyclic group may further have a condensed ring structure, and for example, a benzothiazole ring is preferable. The heterocyclic group may have a substituent, and examples of the substituent include a substituent selected from the above substituent group A, and a chlorine atom is preferable.

In general formula (D), R ¹⁰³ and R ¹⁰⁴ each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group.
The alkyl groups which may R ¹⁰³ and R ¹⁰⁴ represents an alkyl group, preferably an alkyl group having 1 to 6 carbon atoms, more preferably an alkyl group having 1 to 3 carbon atoms, more preferably methyl group. Moreover, as a substituent in case an alkyl group has a substituent, the substituent chosen from the said substituent group A is mentioned, A chlorine atom is preferable.
When R ¹⁰³ and R ¹⁰⁴ represent an aryl group, the aryl group is preferably an aryl group having 6 to 20 carbon atoms, more preferably an aryl group having 6 to 12 carbon atoms, and further preferably a phenyl group. Moreover, as a substituent in case an aryl group has a substituent, the substituent chosen from the said substituent group A is mentioned, A chlorine atom is preferable.
R ¹⁰³ and R ¹⁰⁴ preferably represent a hydrogen atom or a substituted or unsubstituted alkyl group, and more preferably represent a hydrogen atom.

From the viewpoint of ease of synthesis, D in the general formula (1) is a residue obtained by removing a hydrogen atom from at least one of R ¹⁰¹ and R ^{102 in} the general formula (D), or the general formula (D). It is a residue obtained by removing a hydrogen atom from at least one of R ⁴ and R ⁹ therein, or a residue obtained by removing a hydrogen atom from at least one of R ¹¹² and R ^{115 in} the general formula (D). preferable.

The compound represented by the general formula (1) is preferably a compound represented by the following general formula (2).
General formula (2)

In General Formula (2), L ² each independently represents a single bond or a divalent linking group, R ^a represents ^a hydrogen atom or a substituent, and R ^b and R ^c each independently represent a substituent. R ¹ , R ⁵ , R ⁶ and R ¹⁰ each independently represents a substituted or unsubstituted alkyl group. R ³ , R ⁴ , R ⁸ , R ⁹ , R ¹¹¹ , R ¹¹² , R ¹¹³ , R ¹¹⁴ , R ¹¹⁵ , R ¹¹⁶ , R ¹¹⁷ , R ¹¹⁸ , R ¹¹⁹ and R ¹²⁰ are each independently a hydrogen atom or a substituent. Represents. R ¹⁰³ and R ¹⁰⁴ each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group.

In the general formula (2), R ^a , R ^b , R ^c , R ¹ , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁸ , R ⁹ , R ¹⁰ , R ¹⁰³ , R ¹⁰⁴ , R ¹¹¹ , R ¹¹² , R ¹¹³ , R ¹¹⁴ , R ¹¹⁵ , R ¹¹⁶ , R ¹¹⁷ , R ¹¹⁸ , R ¹¹⁹ and R ¹²⁰ are each represented by R ^a , R ^b , R ^c , R ¹ , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁸ , R ⁹ , R ¹⁰ , R ¹⁰³ , R ¹⁰⁴ R ¹¹¹ , R ¹¹² , R ¹¹³ , R ¹¹⁴ , R ¹¹⁵ , R ¹¹⁶ , R ¹¹⁷ , R ¹¹⁸ , R ¹¹⁹ and has the same meaning as R ^120, it is the same specific examples and preferred ranges.

In General Formula (2), each L ² independently represents a single bond or a divalent linking group, and is preferably represented by the following General Formula (L3).
General formula (L3)

In General Formula (L3), R ³¹ represents a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. L ³¹ and L ³² each independently represents a substituted or unsubstituted alkylene group.

In the general formula (L3), R ³¹ has the same meaning as R ¹¹ in the general formula (L1), and specific examples and preferred ranges thereof are also the same.
In the general formula (L3), L ³¹ and L ³² have the same meaning as L ¹¹ in the general formula (L1), and specific examples and preferred ranges thereof are also the same.

Formula (L3) ^{L 32} and the general formula (2) carbon atom of the carbonyl group is bonded in the, it is preferable that the N of ^{L 31} of the general formula (L3) (2) are attached.

It is also preferred that the compound represented by the general formula (1) is a compound represented by the following general formula (3).
General formula (3)

In General Formula (3), L ³ represents a single bond or a divalent linking group, R ^a represents ^a hydrogen atom or a substituent, and R ^b and R ^c each independently represent a substituent. R ¹ , R ⁵ , R ⁶ and R ¹⁰ each independently represents a substituted or unsubstituted alkyl group. R ³ , R ⁴ , R ⁸ , R ¹¹¹ , R ¹¹² , R ¹¹³ , R ¹¹⁴ , R ¹¹⁵ , R ¹¹⁶ , R ¹¹⁷ , R ¹¹⁸ , R ¹¹⁹ and R ¹²⁰ each independently represent a hydrogen atom or a substituent. R ¹⁰¹ and R ¹⁰² each independently represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group. R ¹⁰³ and R ¹⁰⁴ each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group.

In the general formula (3), R ^a , R ^b , R ^c , R ¹ , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁸ , R ¹⁰ , R ¹⁰¹ , R ¹⁰² , R ¹⁰³ , R ¹⁰⁴ , R ¹¹¹ , R ¹¹² , R ¹¹³ , R ¹¹⁴ , R ¹¹⁵ , R ¹¹⁶ , R ¹¹⁷ , R ¹¹⁸ , R ¹¹⁹ and R ¹²⁰ are each represented by R ^a , R ^b , R ^c , R ¹ , and R ¹²⁰ in general formula (1). ^{R 3, R 4, R 5} , R 6, R 8, R 10, R 101, R 102, R 103, R 104, R 111, R 112, R 113, R 114, R 115, R 116, R 117 , R ¹¹⁸ , R ¹¹⁹ and R ¹²⁰ , and specific examples and preferred ranges are also the same.

In General Formula (3), L ³ represents a single bond or a divalent linking group, and is preferably represented by the following General Formula (L4).
General formula (L4)

In General Formula (L4), R ⁴¹ represents a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. L ⁴¹ represents a substituted or unsubstituted alkylene group.
In the general formula (L4), R ⁴¹ has the same meaning as R ²¹ in the general formula (L2), and specific examples and preferred ranges thereof are also the same.
In the general formula (L4), L ⁴¹ has the same meaning as L ²¹ in the general formula (L2), and specific examples and preferred ranges thereof are also the same.

It is also preferred that the compound represented by the general formula (1) is a compound represented by the following general formula (4).
General formula (4)

In General Formula (4), L ⁴ each independently represents a single bond or a divalent linking group, R ^a represents ^a hydrogen atom or a substituent, and R ^b and R ^c each independently represent a substituent. R ¹ , R ⁵ , R ⁶ and R ¹⁰ each independently represents a substituted or unsubstituted alkyl group. R ³ , R ⁸ , R ¹¹¹ , R ¹¹² , R ¹¹³ , R ¹¹⁴ , R ¹¹⁵ , R ¹¹⁶ , R ¹¹⁷ , R ¹¹⁸ , R ¹¹⁹ and R ¹²⁰ each independently represent a hydrogen atom or a substituent. R ¹⁰¹ and R ¹⁰² each independently represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group. R ¹⁰³ and R ¹⁰⁴ each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group.

In the general formula (4), R ^a , R ^b , R ^c , R ¹ , R ³ , R ⁵ , R ⁶ , R ⁸ , R ¹⁰ , R ¹⁰¹ , R ¹⁰² , R ¹⁰³ , R ¹⁰⁴ , R ¹¹¹ , R ¹¹² , R ¹¹³ , R ¹¹⁴ , R ¹¹⁵ , R ¹¹⁶ , R ¹¹⁷ , R ¹¹⁸ , R ¹¹⁹ and R ¹²⁰ are each represented by R ^a , R ^b , R ^c , R ¹ , R ³ , R ⁵ , R ⁶ , R ⁸ , R ¹⁰ , R ¹⁰¹ , R ¹⁰² , R ¹⁰³ , R ¹⁰⁴ , R ¹¹¹ , R ¹¹² , R ¹¹³ , R ¹¹⁴ , R ¹¹⁵ , R ¹¹⁶ , R ¹¹⁷ , R ¹¹⁸ , R ¹¹⁹ And R ¹²⁰ , and specific examples and preferred ranges are also the same.

In General Formula (4), L ⁴ represents a single bond or a divalent linking group, and is preferably represented by General Formula (L4).

The sulfur atom of the sulfonyl group of the general formula (L4) and the carbon atom of the benzene ring of the general formula (3) or (4) are bonded, and L ⁴¹ of the general formula (L4) and the general formula (3) or (4) N is preferably bonded.

It is also preferred that the compound represented by the general formula (1) is a compound represented by the following general formula (5).
General formula (5)

In General Formula (5), L ⁵ each independently represents a single bond or a divalent linking group, R ^a represents ^a hydrogen atom or a substituent, and R ^b and R ^c each independently represent a substituent. R ¹ , R ⁵ , R ⁶ and R ¹⁰ each independently represents a substituted or unsubstituted alkyl group. R ³ , R ⁴ , R ⁸ , R ⁹ , R ¹¹¹ , R ¹¹² , R ¹¹³ , R ¹¹⁴ , R ¹¹⁶ , R ¹¹⁷ , R ¹¹⁸ , R ¹¹⁹ and R ¹²⁰ each independently represent a hydrogen atom or a substituent. R ¹⁰¹ and R ¹⁰² each independently represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group. R ¹⁰³ and R ¹⁰⁴ each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group.

In the general formula (5), R ^a , R ^b , R ^c , R ¹ , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁸ , R ⁹ , R ¹⁰ , R ¹⁰¹ , R ¹⁰² , R ¹⁰³ , R ¹⁰⁴ , R ¹¹¹ , R ¹¹² , R ¹¹³ , R ¹¹⁴ , R ¹¹⁶ , R ¹¹⁷ , R ¹¹⁸ , R ¹¹⁹ and R ¹²⁰ are respectively R ^a , R ^b , R ^c , R ¹ , R ³ , R ⁵ , R ⁶ , R ⁸ , R ¹⁰ , R ¹⁰¹ , R ¹⁰² , R ¹⁰³ , R ¹⁰⁴ , R ¹¹¹ , R ¹¹² , R ¹¹³ , R ¹¹⁴ , R ¹¹⁶ , R ¹¹⁷ , R ¹¹⁸ , R ¹¹⁹ And R ¹²⁰ , and specific examples and preferred ranges are also the same.

In General Formula (5), L ⁵ represents a single bond or a divalent linking group, and is preferably represented by General Formula (L4).

Formula (L4) of carbon atoms of the benzene ring of the sulfur atom of the general formula sulfonyl group (5) is attached, and it is preferable that the N of L ⁴¹ of the general formula (L4) (5) are attached.

It is also preferred that the compound represented by the general formula (1) is a compound represented by the following general formula (6).
General formula (6)

In General Formula (6), L ⁶ each independently represents a single bond or a divalent linking group, R ^a represents ^a hydrogen atom or a substituent, and R ^b and R ^c each independently represent a substituent. R ¹ , R ⁵ , R ⁶ and R ¹⁰ each independently represents a substituted or unsubstituted alkyl group. R ³ , R ⁴ , R ⁸ , R ⁹ , R ¹¹¹ , R ¹¹³ , R ¹¹⁴ , R ¹¹⁶ , R ¹¹⁷ , R ¹¹⁸ , R ¹¹⁹ and R ¹²⁰ each independently represent a hydrogen atom or a substituent. R ¹⁰¹ and R ¹⁰² each independently represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group. R ¹⁰³ and R ¹⁰⁴ each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group.

In the general formula (6), R ^a , R ^b , R ^c , R ¹ , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁸ , R ⁹ , R ¹⁰ , R ¹⁰¹ , R ¹⁰² , R ¹⁰³ , R ¹⁰⁴ , R ¹¹¹ , R ¹¹³ , R ¹¹⁴ , R ¹¹⁶ , R ¹¹⁷ , R ¹¹⁸ , R ¹¹⁹ and R ¹²⁰ are each represented by R ^a , R ^b , R ^c , R ¹ , R ³ , Synonymous with R ⁵ , R ⁶ , R ⁸ , R ¹⁰ , R ¹⁰¹ , R ¹⁰² , R ¹⁰³ , R ¹⁰⁴ , R ¹¹¹ , R ¹¹³ , R ¹¹⁴ , R ¹¹⁶ , R ¹¹⁷ , R ¹¹⁸ , R ¹¹⁹ and R ¹²⁰ There are also specific examples and preferred ranges.

In General Formula (6), L ⁶ represents a single bond or a divalent linking group, and is preferably represented by General Formula (L4).

It is preferable that the sulfur atom of the sulfonyl group of the general formula (L4) and the carbon atom of the benzene ring of the general formula (6) are bonded, and L ⁴¹ of the general formula (L4) and N of the general formula (6) are bonded.

  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, Et represents an ethyl group, and i-Pr represents an isopropyl group.

  The method for synthesizing the compound represented by the general formula (1) of the present invention is not particularly limited. For example, the method described in [0154] to [0169] of JP2010-254964A, A method in accordance with the method described in [0130] to [0131] of Kai 2013-49776 can be used. Specifically, a synthesis example is illustrated in the Examples.

(Coloring composition)
The coloring composition of the present invention contains at least one compound represented by the above general formula (1). The coloring composition of the present invention can contain a medium, but when a solvent is used as the medium, it is particularly suitable as an ink for inkjet recording. The coloring composition of the present invention can be prepared by dissolving and / or dispersing the compound represented by the general formula (1) in a lipophilic medium or an aqueous medium as a medium. it can. Preferably, an aqueous medium is used. The coloring composition of the present invention includes an ink composition excluding a medium.

  In the present invention, the content of the compound of the present invention contained in the colored composition is determined by the type of substituent in the general formula (1) used, the type of solvent component used for producing the colored composition, and the like. However, it is preferable that content of the compound represented by General formula (1) in a coloring composition is contained 1-20 mass% with respect to the gross mass of a coloring composition, and 1-10 mass% is contained. It is more preferable, and it is still more preferable that 2-6 mass% is contained.

  By setting the content of the compound represented by the general formula (1) contained in the coloring composition to 1% by mass or more, it is possible to improve the print density of the ink on the recording medium when printed, and it is necessary. Image density can be ensured. Moreover, when the total amount of the compounds represented by the general formula (1) contained in the colored composition is 20% by mass or less, the dischargeability of the colored composition can be improved when used in the ink jet recording method. In addition, it is possible to obtain an effect such that the inkjet nozzle is not easily clogged.

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

[Ink for inkjet recording]
Next, the ink for inkjet recording of the present invention will be described.
The present invention also relates to an inkjet recording ink containing at least one compound represented by the general formula (1) of the present invention.
The ink for inkjet recording can be produced by dissolving and / or dispersing the compound (mixture) of the present invention in an oleophilic medium or an aqueous medium. Preferably, the ink uses an aqueous medium. If necessary, other additives can be contained within a range that does not impair the effects of the present invention. Other additives include, for example, anti-drying agents (wetting agents), anti-fading agents, emulsion stabilizers, penetration enhancers, ultraviolet absorbers, preservatives, anti-fungal agents, pH adjusters, surface tension adjusters, Well-known additives, such as a foaming agent, a viscosity modifier, a dispersing agent, a dispersion stabilizer, a rust preventive agent, a chelating agent, are mentioned. These various additives are directly added to the ink liquid in the case of water-soluble ink. When an oil-soluble dye is used in the form of a dispersion, it is generally added to the dispersion after the preparation of the dye dispersion, but it may be added to the oil phase or the aqueous phase at the time of preparation.

  The compound of the present invention is preferably contained in an amount of 0.2% by mass or more and 10% by mass or less, and more preferably 1% by mass or more and 6% by mass or less, in 100% by mass of the ink for inkjet recording of the present invention. In addition, the inkjet recording ink of the present invention may be used in combination with other dyes together with the compound of the present invention. When using 2 or more types of pigment | dyes together, it is preferable that the sum total of content of a pigment | dye is the said range.

  The ink for 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 inkjet recording of the present invention can be used not only for forming a single color image but also for forming a full color image. In particular, it is preferably used as an ink jet recording ink having a magenta color tone.

  The ink composition of the present invention can be used 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 colored composition or the inkjet recording ink of the present invention.

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

Hereinafter, a recording paper and a recording film used for ink jet printing using the ink of the present invention will be described.
The support in recording paper and recording film is made of chemical pulp such as LBKP and NBKP, mechanical pulp such as GP, PGW, RMP, TMP, CTMP, CMPMP, CGP, and waste paper pulp such as DIP. Additives such as known pigments, binders, sizing agents, fixing agents, cationic agents, paper strength enhancers, etc. can be mixed and manufactured using various devices such as long net paper machines and circular net paper machines. is there. In addition to these supports, either synthetic paper or plastic film sheets may be used. The thickness of the support is preferably 10 to 250 μm and the basis weight is preferably 10 to 250 g / m ² .

  Polymer latex may be added to the constituent layers (including the backcoat layer) of the ink jet recording paper and recording film. The polymer latex is used for the purpose of improving film physical properties such as dimensional stabilization, curling prevention, adhesion prevention, and film cracking prevention. The polymer latex is described in JP-A Nos. 62-245258, 62-136648, and 62-110066. When a polymer latex having a low glass transition temperature (40 ° C. or lower) is added to a layer containing a mordant, cracking and curling of the layer can be prevented. Also, curling can be prevented by adding a polymer latex having a high glass transition temperature to the backcoat layer.

  The ink of the present invention is not limited to an ink jet recording system, and is a known system, for example, a charge control system that discharges ink using electrostatic attraction, a drop-on-demand system (pressure) that uses the vibration pressure of a piezo element. Pulse method), acoustic ink jet method that converts electrical signal into acoustic beam and irradiates ink and uses ink to discharge ink, and thermal ink jet that heats ink to form bubbles and uses generated pressure Used for systems. Inkjet recording methods use a method of ejecting a large number of low-density inks called photo inks in a small volume, a method of improving image quality using a plurality of inks having substantially the same hue and different concentrations, and colorless and transparent inks. The method is included.

  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.

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

[Synthesis of Intermediate (A)]
20 g of DCSF (manufactured by Chugai Kasei Co., Ltd., trade name), 46 g of 2,4-diaminomesitylene-6-sulfonic acid, 30 g of diazabicycloundecene (DBU) and 6.7 g of zinc chloride are added to 250 g of ethylene glycol at 150 ° C. The reaction was performed for 6 hours. The resulting reaction solution was cooled to room temperature, poured into 1 L of acetonitrile, and the resulting crystals were filtered off, followed by column chromatography (filler: Sephadex LH-20 (Pharmacia), developing solvent: water / methanol). To obtain intermediate (A). Yield 7.7 g, 19% yield, MS (m / z) = 836 ([M-1]-, 100%).

[Synthesis of Intermediate (B)]
After 8.3 g of intermediate (A) was added to 100 g of N, N-dimethylacetamide and heated to 60 ° C., 22 g of succinic anhydride was added in portions over 15 minutes, followed by reaction at 60 ° C. for 2 hours. . The obtained reaction solution was cooled to room temperature, poured into 1 L of saturated brine, and the resulting crystals were filtered off, followed by column chromatography (filler: Sephadex LH-20 (Pharmacia), developing solvent: water / (Methanol) to obtain intermediate (B). Yield 6.8 g, Yield 63%, MS (m / z) = 991 ([M-4Na + 3H] ⁻ , 100%)

[Synthesis of Intermediate (C)]
10.8 g of intermediate (B) was added to 150 g of N, N-dimethylacetamide, and 5 g of diisopropylethylamine was added dropwise thereto, and then the internal temperature was cooled to 5 ° C. Methanesulfonyl chloride 2.5g was dripped here, keeping internal temperature 10 degrees C or less, Then, it was made to react at room temperature for 60 minutes. The obtained reaction solution was poured into 800 mL of acetonitrile, and the resulting crystals were filtered off and washed with 500 mL of acetonitrile to obtain crude crystals of intermediate (C). Crude yield 10.9 g, crude yield 91%, MS (m / z) = 1147 ([M-2Na + 1H] ⁻ , 100%). The obtained crude crystals were used in the next step without purification.

[Synthesis of Exemplary Compound (1-1)]
Intermediate (D) 10 g (synthesized according to the method described in JP 2013-49776 A) is dispersed in 200 g of water, the pH is adjusted to 7.0 using an aqueous sodium hydroxide solution, and the internal temperature is increased to 5 ° C. Cooled down. To this, 11.9 g of crude crystals of intermediate (C) were added in portions at an internal temperature of 10 ° C. or lower, and the pH was continuously adjusted to 7.0 using an aqueous sodium hydroxide solution. It was. The obtained reaction solution was poured into 1 L of saturated saline, and the resulting crystals were filtered off and purified by column chromatography (filler: Sephadex LH-20 (Pharmacia), developing solvent: water / methanol). Example compound (1-1) was obtained. Yield 10.2 g, 54% yield, MS (m / z) = 1737 ([M-6Na + 5H] ⁻ , 100%). The absorption maximum wavelength of the absorption spectrum in the dilute aqueous solution of Exemplified Compound (1-1) was 529 nm.

(Synthesis of Exemplary Compound (1-2))
Exemplary compound (1-2) can be synthesized, for example, according to the following scheme.

[Synthesis of Intermediate (E)]
8.3 g of intermediate (A), which is a synthetic intermediate of exemplary compound (1-1), was dissolved in 100 g of N, N-dimethylacetamide, and the internal temperature was cooled to 5 ° C. Acetic anhydride (5 g) was slowly added dropwise thereto while maintaining the internal temperature at 15 ° C. or lower. After completion of the dropwise addition, the reaction solution was returned to room temperature and reacted for 2 hours. The obtained reaction solution was poured into saturated brine, and the precipitated crystals were separated by filtration. The obtained crystals were purified by column chromatography (filler: Sephadex LH-20 (Pharmacia), developing solvent: water / methanol) to obtain intermediate (E). Yield 8.2 g, 89% yield, MS (m / z) = 875 ([M-2Na + 1H] ⁻ , 100%).

[Synthesis of Exemplified Compound (1-2)]
9.2 g of intermediate (E) was dispersed in 100 g of thionyl chloride and reacted at an internal temperature of 65 ° C. for 6 hours. The residue obtained after distilling off thionyl chloride under reduced pressure was separately dispersed in 200 g of water with 8.0 g of intermediate (F) (synthesized according to the method described in JP 2013-49776 A). The pH was adjusted to 7.0, and the solution was added to a solution whose internal temperature was cooled to 5 ° C while maintaining the internal temperature at 10 ° C or lower. The pH was adjusted to 7 using sodium hydroxide and continued to be added until there was no pH fluctuation. To the obtained reaction solution, 40 g of sodium chloride was added, and the precipitated crystals were separated by filtration. The obtained crystals were purified by column chromatography (filler: Sephadex LH-20 (Pharmacia), developing solvent: water / methanol) to obtain Exemplified Compound (1-2). Yield 10.2 g, 65% yield, MS (m / z) = 1504 ([M-2Na + 1H] ⁻ , 100%). The absorption maximum wavelength of the absorption spectrum in the dilute aqueous solution of Exemplified Compound (1-2) was 528 nm.

(Synthesis of Exemplary Compound (1-4))
The exemplified compound (1-4) can be synthesized, for example, according to the following scheme.

[Synthesis of Intermediate (G)]
8.4 g of intermediate (A), which is a synthetic intermediate of exemplary compound (1-1), was dissolved in 100 g of N, N-dimethylacetamide, and the internal temperature was cooled to 5 ° C. To this, 5 g of isobutyric anhydride was slowly added dropwise while maintaining the internal temperature at 15 ° C. or lower, and after completion of the addition, the reaction solution was returned to room temperature and reacted for 2 hours. The obtained reaction solution was poured into 1 L of saturated brine, and the precipitated crystals were separated by filtration. The obtained crystals were purified by column chromatography (filler: Sephadex LH-20 (Pharmacia), developing solvent: water / methanol) to obtain an intermediate (G). Yield 9.0 g, 92% yield, MS (m / z) = 931 ([M-2Na + 1H] ⁻ , 100%).

[Synthesis of Exemplified Compound (1-4)]
9.8 g of intermediate (G) was dispersed in 100 g of thionyl chloride and reacted at an internal temperature of 65 ° C. for 6 hours. The residue obtained after distilling off thionyl chloride under reduced pressure was separately dispersed in 150 g of water with 4.5 g of intermediate (H) (synthesized according to the method described in JP 2013-49776 A). The pH was adjusted to 7.0 using and the solution was added to a solution whose internal temperature was cooled to 5 ° C. while maintaining the internal temperature at 10 ° C. or lower. The pH was adjusted to 7 using sodium hydroxide and continued to be added until there was no pH fluctuation. 50 g of sodium chloride was added to the obtained reaction solution, and the precipitated crystals were separated by filtration. The obtained crystals were purified by column chromatography (filler: Sephadex LH-20 (Pharmacia), developing solvent: water / methanol) to obtain Exemplified Compound (1-4). Yield 6.8 g, Yield 48%, MS (m / z) = 1346 ([M-3Na + 2H] ⁻ , 100%). The absorption maximum wavelength of the absorption spectrum of the exemplified compound (1-4) in a dilute aqueous solution was 528 nm.

(Synthesis of Exemplary Compound (1-7))
Exemplary compound (1-7) can be synthesized, for example, according to the following scheme.

9.8 g of intermediate (I) (synthesized by the method described in JP2011-148973) was dispersed in 100 g of thionyl chloride and reacted at 45 ° C. for 2 hours. The obtained reaction solution was cooled to room temperature, poured into 800 g of ice water, and the precipitated crystals were separated by filtration. The obtained crystals were dispersed in 200 g of ice water, and 7.6 g of intermediate (J) (synthesized by the method described in JP 2013-49776 A) was added thereto and stirred for 5 minutes at an internal temperature of 0 to 5 ° C. Thereafter, while maintaining the internal temperature at 0 to 5 ° C., the pH was adjusted to 7.0 using a 2M aqueous sodium hydroxide solution, and the addition was continued until there was no pH fluctuation. The resulting reaction solution was concentrated and dried after removing inorganic salts using a dialysis membrane (fractionated molecular weight 3500, Spectra / Por3 Dialysis Membrane (trade name, Spectrum = Laboratory)), and the residue was concentrated to dryness. The exemplified compound (1-7) was isolated by purification with chromatography (filler: Sephadex LH-20 (Pharmacia, trade name), developing solvent: water / methanol = 1/1 (v / v)). 8.6 g, yield 46%, MS (m / z) = 11761 ([M-4Na + 3H] ⁻ , 100%) The absorption maximum wavelength of the visible absorption spectrum of the dilute aqueous solution of Example Compound (1-7) is 536 nm. there were.

(Synthesis of Exemplary Compound (1-9))
Exemplified compound (1-9) was obtained in the same manner except that the amount of intermediate (J) in the synthesis of exemplified compound (1-7) was changed to 3.8 g. Yield 4.2 g, 33% yield. MS (m / z) = 1200 ([M-3Na + 2H] ^- , 100%). The absorption maximum wavelength of the visible absorption spectrum of the dilute aqueous solution of Example Compound (1-9) was 534 nm.

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

[Example 1]
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 aqueous sodium hydroxide solution, and the mixture was filtered under reduced pressure through a microfilter having an average pore size of 0.25 μm to prepare ink jet recording ink 1 as a magenta ink liquid.

Inkjet recording ink 1 composition:
Dye (Exemplary Compound (1-1)) 3.50 g
Diethylene glycol 10.65g
Glycerin 14.70g
Diethylene glycol monobutyl ether 12.70g
Triethanolamine 0.65g
Olfin E1010 (Nissin Chemical Industry Co., Ltd.) 0.9g

[Examples 2 to 10, Comparative Examples 1 and 2]
Inkjet recording inks 2 to 10 were prepared in the same manner as the inkjet recording ink 1 except that the dye was changed as shown in Table 1 below. Moreover, the inkjet recording ink using the comparative compound 1-comparative compound 2 shown below as a comparative inkjet recording ink was prepared, respectively.

(Image recording and evaluation)
The following evaluation was performed on the inks for ink jet recording in each of the examples and comparative examples. The results are shown in Table 1.
In Table 1, the ozone resistance, light resistance, and moisture resistance are as follows: each ink jet recording ink is loaded into an ink cartridge, and photo glossy paper (Canon photographic paper professional) is printed with an ink jet printer (Canon Pixus iP8600, product name). Evaluation was performed after recording an image on PT-201, product name). The image includes a monochrome image pattern in which the density changes stepwise so that the reflected image density measured by a reflection densitometer (X-Rite 310TR) is about 0.7 to 1.8, and a check pattern (density 100%). And 0% 1.5 mm square square pattern).

<Light resistance>
After measuring the image density Ci immediately after recording, the image was irradiated with xenon light (100,000 lux) for 7 days using a weather meter (Atlas C.165), and then the image density Cf was measured again. 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). The dye residual ratio was measured using an image portion having an initial reflection density of around 1.0. The residual dye ratio was evaluated in three stages: A for 85% or more, B for 75% to less than 85%, and C for less than 75%.

<Ozone resistance>
While passing dry air through the Siemens type ozonizer's double glass tube, an AC voltage of 5 kV is applied, and this is used to form an image in a box where the ozone gas concentration is 5 ± 0.1 ppm, set at room temperature in a dark place. The photo glossy paper is allowed to stand for 1 day, and the image density before and after being left under ozone gas is measured using a reflection densitometer (X-Rite 310TR, product name), and the initial image density Ci and the image density Cf after being left under ozone gas are measured. ₂ was evaluated as a dye residual ratio (Cf ₂ / Ci × 100%). The dye residual ratio was measured using an image portion having an initial reflection density of around 1.0. The ozone gas concentration in the box was set using an ozone gas monitor (model: OZG-EM-01) manufactured by APPLICS.
The dye residual ratio was evaluated in three stages: A for 80% or more, B for 70% or more and less than 80%, and C for less than 70%.

<Moisture resistance>
During ink-jet recording, a check pattern (a pattern in which squares having a 1.5 mm square with a density of 100% and 0% were alternately combined) was created to obtain a magenta-white check pattern print with high contrast. . After printing, the printed matter with a check pattern that has been dried for 24 hours is left in an environment of 80 ° C. and 70% RH for 7 days, and the degree of bleeding from the colored portion to the white portion is visually evaluated. Evaluation was made in three stages, where B was slightly blurred and C was blurred.

<Ink storage stability>
The prepared ink cartridge was aged for one month in a constant temperature bath at 60 ° C., and then inkjet recording was performed again. In the ink jet recording before and after this test, A was obtained when the same recorded image was obtained with respect to density and hue, B was changed when either density or hue changed, and both density and hue changed. The ones (or the ones that could not be recorded well) were evaluated in 3 grades.

As is apparent from the results in Table 1, the inks of Examples using the compounds of the present invention were excellent in all of light resistance, ozone resistance, moisture resistance, and storage stability.
In the following structural formulas, Me represents a methyl group, and Ac represents an acetyl group.
Comparative compound 1:

Comparative compound 2:

Claims (17)

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

In general formula (1), D represents a residue obtained by removing n hydrogen atoms from a compound represented by the following general formula (D), L represents a single bond or a divalent linking group, and R ^a represents A hydrogen atom or a substituent is represented, and R ^b and R ^c each independently represent a substituent. n represents an integer of 1 to 4.
Formula (D)

In general formula (D), R ¹ , R ⁵ , R ⁶ and R ¹⁰ each independently represents a substituted or unsubstituted alkyl group. R ³ , R ⁴ , R ⁸ , R ⁹ , R ¹¹¹ , R ¹¹² , R ¹¹³ , R ¹¹⁴ , R ¹¹⁵ , R ¹¹⁶ , R ¹¹⁷ , R ¹¹⁸ , R ¹¹⁹ and R ¹²⁰ are each independently a hydrogen atom or a substituent. Represents. R ¹⁰¹ and R ¹⁰² each independently represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group. R ¹⁰³ and R ¹⁰⁴ each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. The compound according to claim 1, wherein D is a residue obtained by removing a hydrogen atom from at least one of R ¹⁰¹ and R ^{102 in} the general formula (D). The compound according to claim 1, wherein D is a residue obtained by removing a hydrogen atom from at least one of R ⁴ and R ^{9 in} the general formula (D). The compound according to any one of claims 1 to 3, wherein the L is represented by the following general formula (L1) or (L2).
General formula (L1)

In General Formula (L1), R ¹¹ represents a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. L ¹¹ represents a substituted or unsubstituted alkylene group.
General formula (L2)

In General Formula (L2), R ²¹ represents a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. L ²¹ represents a substituted or unsubstituted alkylene group.   The compound according to any one of claims 1 to 4, wherein n represents 1 or 2. The compound represented by the said General formula (1) is a compound of Claim 1, 2, or 4 represented by following General formula (2).
General formula (2)

In General Formula (2), L ² each independently represents a single bond or a divalent linking group, R ^a represents ^a hydrogen atom or a substituent, and R ^b and R ^c each independently represent a substituent. R ¹ , R ⁵ , R ⁶ and R ¹⁰ each independently represents a substituted or unsubstituted alkyl group. R ³ , R ⁴ , R ⁸ , R ⁹ , R ¹¹¹ , R ¹¹² , R ¹¹³ , R ¹¹⁴ , R ¹¹⁵ , R ¹¹⁶ , R ¹¹⁷ , R ¹¹⁸ , R ¹¹⁹ and R ¹²⁰ are each independently a hydrogen atom or a substituent. Represents. R ¹⁰³ and R ¹⁰⁴ each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. The compound of Claim 1, 3 or 5 by which the compound represented by the said General formula (1) is represented by following General formula (3).
General formula (3)

In General Formula (3), L ³ represents a single bond or a divalent linking group, R ^a represents ^a hydrogen atom or a substituent, and R ^b and R ^c each independently represent a substituent. R ¹ , R ⁵ , R ⁶ and R ¹⁰ each independently represents a substituted or unsubstituted alkyl group. R ³ , R ⁴ , R ⁸ , R ¹¹¹ , R ¹¹² , R ¹¹³ , R ¹¹⁴ , R ¹¹⁵ , R ¹¹⁶ , R ¹¹⁷ , R ¹¹⁸ , R ¹¹⁹ and R ¹²⁰ each independently represent a hydrogen atom or a substituent. R ¹⁰¹ and R ¹⁰² each independently represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group. R ¹⁰³ and R ¹⁰⁴ each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. The compound represented by the said General formula (1) is a compound of Claim 1, 3 or 5 represented by following General formula (4).
General formula (4)

In General Formula (4), L ⁴ each independently represents a single bond or a divalent linking group, R ^a represents ^a hydrogen atom or a substituent, and R ^b and R ^c each independently represent a substituent. R ¹ , R ⁵ , R ⁶ and R ¹⁰ each independently represents a substituted or unsubstituted alkyl group. R ³ , R ⁸ , R ¹¹¹ , R ¹¹² , R ¹¹³ , R ¹¹⁴ , R ¹¹⁵ , R ¹¹⁶ , R ¹¹⁷ , R ¹¹⁸ , R ¹¹⁹ and R ¹²⁰ each independently represent a hydrogen atom or a substituent. R ¹⁰¹ and R ¹⁰² each independently represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group. R ¹⁰³ and R ¹⁰⁴ each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. 6. The compound according to claim 1, 3 or 5, wherein the compound represented by the general formula (1) is represented by the following general formula (5).
General formula (5)

In General Formula (5), L ⁵ each independently represents a single bond or a divalent linking group, R ^a represents ^a hydrogen atom or a substituent, and R ^b and R ^c each independently represent a substituent. R ¹ , R ⁵ , R ⁶ and R ¹⁰ each independently represents a substituted or unsubstituted alkyl group. R ³ , R ⁴ , R ⁸ , R ⁹ , R ¹¹¹ , R ¹¹² , R ¹¹³ , R ¹¹⁴ , R ¹¹⁶ , R ¹¹⁷ , R ¹¹⁸ , R ¹¹⁹ and R ¹²⁰ each independently represent a hydrogen atom or a substituent. R ¹⁰¹ and R ¹⁰² each independently represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group. R ¹⁰³ and R ¹⁰⁴ each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. 6. The compound according to claim 1, 3 or 5, wherein the compound represented by the general formula (1) is represented by the following general formula (6).
General formula (6)

In General Formula (6), L ⁶ each independently represents a single bond or a divalent linking group, R ^a represents ^a hydrogen atom or a substituent, and R ^b and R ^c each independently represent a substituent. R ¹ , R ⁵ , R ⁶ and R ¹⁰ each independently represents a substituted or unsubstituted alkyl group. R ³ , R ⁴ , R ⁸ , R ⁹ , R ¹¹¹ , R ¹¹³ , R ¹¹⁴ , R ¹¹⁶ , R ¹¹⁷ , R ¹¹⁸ , R ¹¹⁹ and R ¹²⁰ each independently represent a hydrogen atom or a substituent. R ¹⁰¹ and R ¹⁰² each independently represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group. R ¹⁰³ and R ¹⁰⁴ each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. The compound according to claim 6, wherein L ² is represented by the following general formula (L3).
General formula (L3)

In General Formula (L3), R ³¹ represents a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. L ³¹ and L ³² each independently represents a substituted or unsubstituted alkylene group. The compound according to claim 7, 8, 9 or 10, wherein each of L ³ , L ⁴ , L ⁵ or L ⁶ is independently represented by the following general formula (L4).
General formula (L4)

In General Formula (L4), R ⁴¹ represents a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. L ⁴¹ represents a substituted or unsubstituted alkylene group.   The coloring composition containing the compound of any one of Claims 1-12.   Ink for inkjet recording containing the compound of any one of Claims 1-12.   An ink jet recording method using the ink for ink jet recording according to claim 14.   An ink jet printer cartridge filled with the ink for ink jet recording according to claim 14.   An ink-jet recorded matter in which a colored image is formed on a recording material using the ink for ink-jet recording according to claim 14.