JP2001152055A - Ink for ink jet recording and method for recording image with the same - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide an ink which is used for ink jet recordings and can form images having good hues and high light fastness. SOLUTION: This ink which is used for ink jet recordings and contains a compound represented by general formula (1) Ar is an aryl group or heterocyclic group; R1 to R4 are each independently H, or one of various substituents; when R1 to R4 and Ar are each an aryl group or heterocyclic group having one or more substituents, at least one of the substituents is a water-soluble group such as CO2H, SO3H, a quaternary ammonium group, CO2M1/n or SO3M1/n [M is a metal atom; (n) is an integer of 1 to 4].

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

The present invention relates to an ink jet recording ink and an image recording method using the same.

[0002]

2. Description of the Related Art Ink jet recording systems have rapidly spread and are further developed due to low material costs, high-speed recording, low noise during recording, and easy color recording. It is a recording method that is changing. Ink jet recording methods include a method in which pressure is applied by a piezo element to eject droplets, a method in which bubbles are generated in ink by heat to eject droplets, and a method in which droplets are sucked and ejected by electrostatic force. There are water-based inks, oil-based inks, and solid (melt-type) inks as inkjet inks.

JP-A-4-359967 and JP-A-4-35967
JP-A-359968 discloses a dye for the purpose of achieving both hue and light fastness, but its performance as a water-based ink is not sufficient, and further improvement in hue is particularly desired.

[0004]

SUMMARY OF THE INVENTION An object of the present invention is to provide an ink jet recording ink and an image recording method capable of forming an image having good hue and good light fastness.

[0005]

Means for solving the above problems are as follows. <1> An inkjet recording ink containing a compound represented by the following general formula (1).

[0006]

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In the general formula (1), Ar represents an aryl group or a heterocyclic group, and R ^{1 to} R ⁴ each independently represent a hydrogen atom, a halogen atom, an alkyl group, an aryl group, an acyl group, a carbamoyl group. , Sulfamoyl, alkoxycarbonyl, aryloxycarbonyl, acyloxy, alkoxy, aryloxy, alkylthio, arylthio, alkylsulfonyl, arylsulfonyl, alkylphosphoryl, arylphosphoryl, amino, -CN , -OH, -CO ₂ H, -S
O ₃ H, quaternary ammonium group, —CO ₂ M _{1 / n} , or —
SO ₃ M _{1 / n} , M represents a metal atom, n represents an integer of 1 to 4, and the compound represented by the general formula (1) has at least one water-soluble group in the molecule.

<2> The ink for inkjet recording according to <1>, wherein Ar is represented by the following general formula (2) in the general formula (1).

[0009]

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In the general formula (2), R^Five, R⁶Are independent
To represent a hydrogen atom, an alkyl group, or an aryl group.
Then R⁷~ R^TenAre each independently a hydrogen atom, a halogen atom
Child, alkyl group, aryl group, acyl group, carbamoyl
Group, sulfamoyl group, alkoxycarbonyl group, ant
Oxycarbonyl group, acyloxy group, alkoxy
Group, aryloxy group, alkylthio group, arylthio
Group, alkylsulfonyl group, arylsulfonyl group,
Alkyl phosphoryl group, aryl phosphoryl group, amino
Group, -CN, -OH, -CO_TwoH, -SO_ThreeH, 4th grade
Monium group, -CO _TwoM_{1 / n}Or -SO_ThreeM_{1 / n}The table
M represents a metal atom, and n represents an integer of 1 to 4.

<3> The ink for inkjet recording according to <1>, wherein Ar is a group represented by the following general formula (3).

[0012]

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In the general formula (3), R ^{11 to} R ¹³ each independently represent a hydrogen atom, an alkyl group or an aryl group;
R ¹⁴ is a hydrogen atom, a halogen atom, an alkyl group, an aryl group, an alkoxy group, an aryloxy group, -OH, -CO
₂ H, —SO ₃ H, quaternary ammonium group, —CO ₂ M _{1 / n} ,
Or an -SO ₃ M 1 _{/ n,} M represents a metal atom, n represents an integer of 1 to 4, X represents an oxygen atom or a sulfur atom.

<4> The ink for inkjet recording according to <1>, wherein Ar is a group represented by the following general formula (4).

[0015]

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In the general formula (4), R ¹⁵ represents a hydrogen atom or an alkyl group, and R ¹⁶ and R ¹⁷ each independently represent a hydrogen atom, a halogen atom, an alkyl group, an aryl group, an alkoxy group, an aryloxy group. , an alkylthio group, an arylthio group, -OH, -CO ₂ H, represents -SO ₃ H, 4 quaternary ammonium groups, -CO ₂ M _{1 / n,} or a -SO ₃ M _{1 / n,} M
Represents a metal atom, n represents an integer of 1 to 4, and Y represents an oxygen atom or a sulfur atom.

<5> Water-soluble group is -CO ₂ H, -SO
₃ H, quaternary ammonium group, -CO ₂ M _{1 / n} , or -S
The ink for inkjet recording according to any one of <1> to <4>, which is O ₃ M _{1 / n} . <6> An energy is supplied to the ink jet recording ink according to any one of <1> to <5> to discharge droplets of the ink onto a recording medium, and the ink droplets are formed on the recording medium. An image recording method for recording an image.

[0018]

BEST MODE FOR CARRYING OUT THE INVENTION The ink for ink-jet recording of the present invention contains a compound represented by the general formula (1) as a dye. The compound represented by the general formula (1) has good hue and good light fastness. Therefore, an image formed using the ink for ink jet recording of the present invention has a feature that it has a good hue and the light fastness of an image portion is good.

In the general formula (1), R¹~ R^FourAre independent
A hydrogen atom, a halogen atom, an alkyl group, an aryl
Group, acyl group, carbamoyl group, sulfamoyl group,
Alkoxycarbonyl group, aryloxycarbonyl group,
Acyloxy group, alkoxy group, aryloxy group,
Alkylthio group, arylthio group, alkylsulfonyl
Group, arylsulfonyl group, alkylphosphoryl group,
Reel phosphoryl group, amino group, -CN, -OH, -C
O_TwoH, -SO_ThreeH, quaternary ammonium group, -CO
_TwoM_{1 / n}Or -SO_ThreeM_{1 / n}Represents M represents a metal atom
And n represents an integer of 1 to 4.

When R ^{1 to} R ⁴ represent a halogen atom, examples of the halogen atom include a fluorine atom, a chlorine atom and a bromine atom, and a fluorine atom and a chlorine atom are preferred.

When R ^{1 to} R ⁴ represent an aryl group, R ¹ to R ⁴
The aryl group represented by R ⁴ includes an unsubstituted aryl group and an aryl group having a substituent. When R ^{1 to} R ⁴ represent an aryl group having a substituent, examples of the substituent include an alkyl group, an alkoxy group, an aryloxy group, a halogen atom, a nitro group, a cyano group, a substituted carbamoyl group, a substituted sulfamoyl group, and a substituted amino group. A substituted oxycarbomoyl group, a substituted oxysulfonyl group, an alkylthio group,
Arylthio, alkylsulfonyl, arylsulfonyl, aryl, hydroxy, acyl, acyloxy, substituted sulfonyloxy, substituted aminocarbonyloxy, substituted phosphoryloxy, -CO
₂ H, —SO ₃ H, quaternary ammonium group, —CO ₂ M _{1 / n} ,
Or include -SO ₃ M _{1 / n.} Here, M represents a metal atom, and n represents an integer of 1 to 4.

The aryl group represented by R ^{1 to} R ⁴ includes
An aryl group having 6 to 30 carbon atoms is preferable, for example,
Phenyl group, 2-methylphenyl group, 2-chlorophenyl group, 2-methoxyphenyl group, 2-ethoxyphenyl group, 2-propoxyphenyl group, 2-isopropoxyphenyl group, 2-butoxyphenyl group, 2- (2- Ethylhexyloxy) phenyl group, 2-octyloxyphenyl group, 2-undecyloxyphenyl group, 2-trifluoromethylphenyl group, 2- (2-ethylhexyloxy) -5-chlorophenyl group, 2,2′-hexyloxy -3,5-dichlorophenyl group, 3- (2,4-di-t-pentylphenoxyethoxy) phenyl group, 2-
(Dibutylaminocarbonylethoxy) phenyl group,
2,4-dichlorophenyl group, 2,5-dichlorophenyl group, 2,4,6-trimethylphenyl group, 3-chlorophenyl group, 3-nitrophenyl group, 3-cyanophenyl group, 3-trifluoromethylphenyl group, 3 -Methoxyphenyl group, 3-ethoxyphenyl group, 3-butoxyphenyl group, 3- (2'-ethylhexyloxy) phenyl group, 3,4-cyclophenyl group, 3,5-dichlorophenyl group, 3,4-dimethoxyphenyl Group, 3,5
-A dibutoxyphenyl group,

3-octyloxyphenyl group, 3- (dibutylaminocarbonylmethoxy) phenyl group, 3-
(Di-2-ethylhexylaminocarbonylmethoxy)
Phenyl, 3-dodecyloxyphenyl, 4-chlorophenyl, 4-cyanophenyl, 4-nitrophenyl, 4-trifluoromethylphenyl, 4-methoxyphenyl, 4-ethoxyphenyl, 4-iso Propoxyphenyl group, 4-butoxyphenyl group, 4-
(2-ethylhexyloxy) phenyl group, 4-isopentyloxyphenyl group, 4- (octadecyloxy)
Phenyl group, 4-benzylphenyl group, 4-aminosulfonylphenyl group, 4-N, N-dibutylsulfonylphenyl group, 4-ethoxycarbonylphenyl group, 4-
A (2-ethylhexyloxycarbonyl) phenyl group,
4-t-octylphenyl group, 4-fluorophenyl group, 3-acetylphenyl group, 2-acetylaminophenyl group, 2,4-di-t-pentylphenyl group, 4-
(2-ethylhexyloxy) carbonylphenyl group,
4-methylthiophenyl, 4- (4-chlorophenylthio) phenyl, hydroxyphenyl, phenylsulfonylphenyl, phenylsulfonyloxyphenyl, phenylcarbonyloxyphenyl, dimethylaminocarbonyloxyphenyl, butylcarbonyl An oxyphenyl group, and the like.

The aryl groups represented by R ^{1 to} R ⁴ include the following aryl groups.

[0025]

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When R ^{1 to} R ⁴ represent an alkyl group, R ¹ to R ⁴
The alkyl group represented by R ⁴ includes an unsubstituted alkyl group and an alkyl group having a substituent. Examples of the substituent include an alkoxy group, an aryloxy group, an alkoxycarbonyl group, an aryloxycarbonyl group, an aryl group, a hydroxy group, and a halogen atom. The substituent further includes an alkyl group, an alkoxy group, a nitro group, a cyano group, a hydroxy group, a halogen atom, -CO ₂
H, -SO ₃ H, 4 quaternary ammonium groups, -CO ₂ M _{1 /} n,
Or it may be substituted by -SO ₃ M 1 _{/ n.} Here, M represents a metal atom, and n represents an integer of 1 to 4.

As the alkyl group represented by R ^{1 to} R ⁴ ,
It may be linear or branched, and may have an unsaturated bond. The alkyl group represented by R ^{1 to} R ⁴ is preferably an alkyl group having 1 to 30 carbon atoms, for example, a methyl group, a trifluoromethyl group, an ethyl group, a butyl group, a hexyl group, an octyl group, Ethylhexyl, decyl, dodecyl, octadecyl, propyl, isopropyl, isobutyl, sec-butyl, t-butyl, pentyl, 1-ethylpentyl, cyclopentyl, cyclohexyl, isopentyl, heptyl Group, nonyl group, undecyl group, propenyl group, heptadecenyl group, t-octyl group, ethoxycarbonylmethyl group, butoxycarbonylmethyl group, 2-ethylhexyloxycarbonylmethyl group, 1- (ethoxycarbonyl) ethyl group, 2 ′, 4 '-Diisopentylphenyloxymethyl group, 2', 4'-di- -Butylphenyloxymethyl group, ethoxycarbonylethyl group, 2-ethylhexyloxycarbonylethyl group, butyldecyloxycarbonylethyl group, dibutylaminocarbonylmethyl group, dibenzylaminocarbonylethyl group, ethyloxycarbonylpropyl group, 2-ethylhexyloxy Carbonylpropyl group, 2,4-di-t-amylphenyloxypropyl group, 1- (2 ′, 4′-di-t-amylphenyloxy) propyl group, 2,4-di-t-butylphenyloxypropyl Group, acetylaminoethyl group, N, N-dihexylaminocarbonylethyl group,
2,4-di-t-amyloxyethyloxycarbonylpropyl group, isostearyloxycarbonylpropyl, 1- (2,4-di-t-pentylphenyloxy)
Propyl group, 2,4-di-t-pentylphenyloxyethyloxycarbonylpropyl group, naphthyloxyethyloxycarbonylethyl group, N-methyl-N-phenylethyloxycarbonylethyl group, methanesulfonylaminopropyl group,-(CH ₂ ) _m CO2H,-(CH
_{2) m CO 2 Na, -} (CH 2) m CO 2 K, - (CH 2) m S
_{O 3 H, - (CH 2} ) m SO 3 Na, - (CH 2) m SO 3 K
And the like. Here, m represents an integer of 1 to 4.

When R ^{1 to} R ⁴ represent an acyl group, R ^{1 to} R ⁴
The acyl group represented by represents an unsubstituted acyl group and an acyl group having a substituent. When R ^{1 to} R ⁴ represent an acyl group having a substituent, the substituent is preferably an alkoxy group, an aryloxy group, a halogen atom, an alkylthio group, an arylthio group, or an anilino group. R ¹ ~
The acyl group represented by R ⁴ has 2 to 20 carbon atoms.
Are preferred, for example, acetyl, propanoyl, butanoyl, hexanoyl, octanoyl, 2-ethylhexanoyl, decanoyl, dodecanoyl, octadecanoyl, 2-cyanopropanoyl, And a 1-dimethylpropanoyl group. Further, examples of the acyl group represented by R ^{1 to} R ⁴ include the following acyl groups.

[0029]

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When R ^{1 to} R ⁴ represent a carbamoyl group,
The carbamoyl group represented by ¹ to R ^4, include a carbamoyl group having an unsubstituted carbamoyl group and a substituted group. When R ^{1 to} R ⁴ represent a carbamoyl group having a substituent, the substituent is preferably an alkyl group or an aryl group. As the carbamoyl group represented by R ^{1 to} R ⁴ ,
A carbamoyl group having a total of 1 to 30 carbon atoms is preferable, for example, N-methylcarbamoyl group, N-ethylcarbamoyl group, N-propylcarbamoyl group, N-butylcarbamoyl group, N-hexylcarbamoyl group, N-cyclohexylcarbamoyl group, An N-octylcarbamoyl group,
N-2-ethylhexylcarbamoyl group, N-decylcarbamoyl group, N-octadecylcarbamoyl group, N-
Phenylcarbamoyl group, N-2-methylphenylcarbamoyl group, N-2-chlorophenylcarbamoyl group,
N-2-methoxyphenylcarbamoyl group, N-2-isopropoxyphenylcarbamoyl group, N-2- (2-
Ethylhexyloxy) phenylcarbamoyl group, N-
3-chlorophenylcarbamoyl group, N-3-nitrophenylcarbamoyl group, N-3-cyanophenylcarbamoyl group, N-4-methoxycarbamoyl group, N-4-
(2′-ethylhexyloxy) phenylcarbamoyl, N-4-cyanophenylcarbamoyl, N-methyl-N-phenylcarbamoyl, N, N-dimethylcarbamoyl, N, N-dibutylcarbamoyl,
And N-diphenylcarbamoyl group. Also,
Examples of the carbamoyl group represented by R ^{1 to} R ⁴ include the following carbamoyl groups.

[0031]

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R¹~ R^FourRepresents an alkoxycarbonyl group
If R¹~ R^FourTo the alkoxycarbonyl group represented by
Has an unsubstituted alkoxycarbonyl group and a substituent
Alkoxycarbonyl group. R¹~ R^FourIs placed
When representing an alkoxycarbonyl group having a substituent,
As a substituent of a kill group (alkyl group of an alkoxy moiety)
Is a halogen atom, an alkoxy group, or an aryloxy group
preferable. R¹~ R^FourAn alkoxycarbonyl group represented by
Is an alkoxycarbonyl group having 2 to 20 carbon atoms in total.
Are preferred, for example, methoxycarbonyl group, ethoxy
Carbonyl group, propoxycarbonyl group, butoxycal
Bonyl group, hexyloxycarbonyl group, 2-ethyl
Xyloxycarbonyl group, octyloxycarbonyl
Group, decyloxycarbonyl group, octadecyloxyca
Rubonyl group, phenyloxyethyloxycarbonyl
Group, phenyloxypropyloxycarbonyl group, 2,
4-di-t-amylphenyloxyethylcarbonyl
Group, 2,6-di-t-butyl-4-methylcyclohexyl
Ruoxycarbonyl group, isostearyloxy carbonyl
Group, -CO_Two(CH_Two)_mCO_TwoH, -CO_Two(CH_Two)_m
CO_TwoNa, -CO_Two(CH_Two) _mCO_TwoK, -CO_Two(CH
_Two)_mSO_ThreeH, -CO_Two(CH_Two)_mSO_ThreeNa, -CO
_Two(CH_Two)_mSO_ThreeK and the like. Note that m is 1 to 4.
Represents an integer.

[0033] If the R ¹ to R ⁴ represents an aryloxycarbonyl group, the aryloxycarbonyl group represented by R ¹ to R ^4, an aryloxycarbonyl group an unsubstituted aryloxycarbonyl group and a substituted group included. When R ^{1 to} R ⁴ represent an aryloxycarbonyl group having a substituent, the substituent of the aryl group (the aryl group in the aryloxy moiety) is preferably a halogen atom, an alkyl group, an alkoxy group, or an acylamino group. R ¹ ~
As the aryloxycarbonyl group represented by R ⁴ ,
An aryloxycarbonyl group having a total of 7 to 30 carbon atoms is preferable. For example, a 2-methylphenyloxycarbonyl group, a 2-chlorophenyloxycarbonyl group, a 2,6-
Dimethylphenyloxycarbonyl group, 2,4,6-trimethylphenyloxycarbonyl group, 2-methoxyphenyloxycarbonyl group, 2-butoxyphenyloxycarbonyl group, 3-cyanophenyloxycarbonyl group, 3-nitrophenyloxycarbonyl group, 2,2-
Ethylhexylphenyloxycarbonyl group, 3- (2
-Ethylhexyloxy) phenyloxycarbonyl group, 4-fluorophenyloxycarbonyl group, 4-chlorophenyloxycarbonyl group, 4-cyanophenyloxycarbonyl group, 4-butoxyphenyloxycarbonyl group, and the like. The aryloxycarbonyl groups represented by R ^{1 to} R ⁴ include the following aryloxycarbonyl groups.

[0034]

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When R ^{1 to} R ⁴ represent an acyloxy group,
The acyloxy group represented by ¹ to R ^4, include an acyloxy group having an unsubstituted acyloxy group and a substituted group. When R ^{1 to} R ⁴ represent an acyloxy group having a substituent, the substituent is preferably a halogen atom, an alkoxy group, or an aryloxy group. The acyloxy group represented by R ^{1 to} R ⁴ is preferably an acyloxy group having a total of 2 to 20 carbon atoms, for example, acetyloxy, propanoyloxy, butanoyloxy, pentanoyloxy, trifluoromethyl Examples include carbonyloxy, octanoyloxy, decanoyloxy, undecanoyloxy, and octadecanoyloxy.
The acyloxy groups represented by R ^{1 to} R ⁴ include the following acyloxy groups.

[0036]

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When R ^{1 to} R ⁴ represent an alkoxy group, R ¹
The alkoxy group represented by R ⁴ includes an unsubstituted alkoxy group and an alkoxy group having a substituent. R
^{When 1 to} R ⁴ represent an alkoxy group having a substituent, the substituent is preferably a halogen atom, an alkoxy group, or an aryloxy group. As the alkoxy group represented by R ^{1 to} R ⁴ , an alkoxy group having a total of 1 to 30 carbon atoms is preferable. For example, a methoxy group, an ethoxy group, a propyloxy group, an isopropyloxy group, a butoxy group, an isobutoxy group, a sec- Butoxy, t-butoxy, pentyloxy, isopentyloxy, hexyloxy, heptyloxy, octyloxy, 2-ethylhexyloxy, decyloxy, dodecyloxy, octadecyloxy, ethoxycarbonylmethyloxy Group, 2-ethylhexyloxycarbonylmethyloxy group, aminocarbonylmethyloxy group, N, N-dibutylaminocarbonylmethyloxy group, N-methylaminocarbonylmethyloxy group, N-ethylaminocarbonylmethyloxy group, N-octylamino Mosquito Boni methyl group, N- methyl -N- benzylaminocarbonyl methyl group, a benzyl group, a cyano methyl _{group, -O (CH 2) m CO2H} , -O (CH 2) m CO
_{2 Na, -O (CH 2)} m CO 2 K, -O (CH 2) m SO 3
_{H, -O (CH 2) m} SO 3 Na, -O (CH 2) m SO 3 K
And the like. Here, m represents an integer of 1 to 4.

When R ^{1 to} R ⁴ represent an aryloxy group,
The aryloxy groups represented by R ^{1 to} R ⁴ include an unsubstituted aryloxy group and a substituted aryloxy group. When R ^{1 to} R ⁴ represent an aryloxy group having a substituent, the substituent is preferably a halogen atom, an alkoxy group, a cyano group, a trifluoromethyl group, an aryloxy group, or a nitro group. As the aryloxy group represented by R ^{1 to} R ⁴ , an aryloxy group having a total carbon number of 6 to 30 is preferable.
-Naphthyloxy group, 2-naphthyloxy group, 2-chlorophenyloxy group, 2-methylphenyloxy group, 2
-Methoxyphenyloxy group, 2-butoxyphenyloxy group, 3-chlorophenyloxy group, 3-trifluoromethylphenyloxy group, 3-cyanophenyloxy group, 3- (2-ethylhexyloxy) phenyloxy group, 3- Examples include a nitrophenyloxy group, a 4-fluorophenyloxy group, a 4-cyanophenyloxy group, a 4-butoxyphenyloxy group, a 4- (2-ethylhexyloxy) phenyloxy group, and a 4-octadecylphenyloxy group.

When R ^{1 to} R ⁴ represent an alkylthio group,
The alkylthio group represented by ¹ to R ^4, include an alkylthio group having unsubstituted alkylthio groups and substituents. When R ^{1 to} R ⁴ represent an alkylthio group having a substituent, the substituent is preferably a carbonyl group, an alkoxy group, or an aryloxy group. As the alkylthio group represented by R ^{1 to} R ⁴ , an alkylthio group having a total of 1 to 30 carbon atoms is preferable. For example, methylthio, ethylthio, propylthio, isopropylthio, butylthio, butylthio, isobutylthio, sec- Butylthio, t-butylthio, pentylthio, isopentylthio, hexylthio, heptylthio, octylthio, 2-
Ethylhexylthio, decylthio, dodecylthio, octadecylthio, ethoxycarbonylmethylthio, 2-ethylhexyloxycarbonylmethylthio, aminocarbonylmethylthio, N, N-dibutylaminocarbonylmethyl, N-methylaminocarbonylmethylthio, N-ethylaminocarbonylmethylthio group, N-octylaminocarbonylmethylthio group, N
-Methyl-N-benzylaminocarbonylmethylthio group, benzylthio group, cyanomethylthio group, -S (CH
_{2) m CO 2 H, -S} (CH 2) m CO 2 Na, -S (C
_{H 2) m CO 2 K,} -S (CH 2) m SO 3 H, -S (C
_{H 2) m SO 3 Na,} -S (CH 2) m SO 3 K , and the like.

When R ^{1 to} R ⁴ represent an arylthio group,
The arylthio group represented by ¹ to R ^4, include arylthio groups having unsubstituted arylthio group and a substituted group. When R ^{1 to} R ⁴ represent an arylthio group having a substituent, examples of the substituent include a halogen atom, an alkyl group,
Aryloxy, alkoxy, cyano, trifluoromethyl and nitro groups are preferred. The arylthio group represented by R ^{1 to} R ⁴ is preferably an arylthio group having a total of 6 to 30 carbon atoms, for example, phenylthio, 1-naphthylthio, 2-naphthylthio, 2-chlorophenylthio, 2-methyl Phenylthio group, 2-methoxyphenylthio group, 2-butoxyphenylthio group, 3-chlorophenylthio group, 3-trifluoromethylphenylthio group, 3-cyanophenylthio group, 3- (2-ethylhexyloxy) phenylthio group , 3-nitrophenylthio, 4-fluorophenylthio, 4-cyanophenylthio, 4-butoxyphenylthio, 4- (2-ethylhexyloxy) phenylthio, 4-octadecylphenylthio, and the like. .

When R ^{1 to} R ⁴ represent a sulfamoyl group,
The sulfamoyl group represented by R ^{1 to} R ⁴ includes an unsubstituted sulfamoyl group and a sulfamoyl group having a substituent. When R ^{1 to} R ⁴ represent a sulfamoyl group having a substituent, the substituent is preferably an alkyl group or an aryl group. As the sulfamoyl group represented by R ^{1 to} R ⁴ , a sulfamoyl group having a total of 0 to 30 carbon atoms is preferable. For example, a sulfamoyl group, an N-alkylsulfamoyl group, an N-arylsulfamoyl group, N, N
-Dialkylsulfamoyl group, N, N-diarylsulfamoyl group, N-alkyl-N-arylsulfamoyl group and the like. More specifically, N-methylsulfamoyl group, N-ethylsulfamoyl group, N-
Propylsulfamoyl, N-butylsulfamoyl, N-hexylsulfamoyl, N-cyclohexylsulfamoyl, N-octylsulfamoyl,
N-2-ethylhexylsulfamoyl group, N-decylsulfamoyl group, N-octadecylsulfamoyl group, N-phenylsulfamoyl group, N-2-methylphenylsulfamoyl group, N-2-chlorophenyl Sulfamoyl group, N-2-methoxyphenylsulfamoyl group, N-2-isopropoxyphenylsulfamoyl group, N-2- (2-ethylhexyloxy) phenylsulfamoyl group, N-3-chlorophenylsulfur Famoyl group, N-3-nitrophenylsulfamoyl group, N-
3-cyanophenylsulfamoyl group, N-4-methoxysulfamoyl group, N-4- (2'-ethylhexyloxy) phenylsulfamoyl group, N-4-cyanophenylsulfamoyl group, N-methyl —N-phenylsulfamoyl group, N, N-dimethylsulfamoyl group,
N, N-dibutylsulfamoyl group, N, N-diphenylsulfamoyl group, N, N-di (2-ethylhexyl) sulfamoyl group and the like can be mentioned.

[0042] If the R ¹ to R ⁴ represents an alkylsulfonyl group, the alkylsulfonyl group represented by R ¹ to R ^4, include an alkylsulfonyl group having unsubstituted alkylsulfonyl group and a substituted group. As the alkylsulfonyl group represented by R ^{1 to} R ⁴ , an alkylsulfonyl group having 1 to 20 carbon atoms in total is preferable, for example, a methylsulfonyl group, an ethylsulfonyl group, a propylsulfonyl group, an isopropylsulfonyl group, a butylsulfonyl group, Examples include a hexylsulfonyl group, a cyclohexylsulfonyl group, an octylsulfonyl group, a 2-ethylhexylsulfonyl group, a decanoylsulfonyl group, a dodecanoylsulfonyl group, an octadecanoylsulfonyl group, and a cyanomethylsulfonyl group.

[0043] If the R ¹ to R ⁴ represents an aryl sulfonyl group, the arylsulfonyl group represented by R ¹ to R ^4, include an arylsulfonyl group having unsubstituted arylsulfonyl group and a substituted group. When R ^{1 to} R ⁴ represent an arylsulfonyl group having a substituent, examples of the substituent include a halogen atom, an alkoxy group, an aryloxy group,
Preference is given to cyano, trifluoromethyl and nitro groups. The arylsulfonyl group represented by R ^{1 to} R ⁴ is preferably an arylsulfonyl group having a total of 6 to 30 carbon atoms, for example, phenylsulfonyl, 1-naphthylsulfonyl, 2-naphthylsulfonyl, 2-chlorophenylsulfonyl Group, 2-methylphenylsulfonyl group,
2-methoxyphenylsulfonyl group, 2-butoxyphenylsulfonyl group, 3-chlorophenylsulfonyl group,
3-trifluoromethylphenylsulfonyl group, 3-cyanophenylsulfonyl group, 3- (2-ethylhexyloxy) phenylsulfonyl group, 3-nitrophenylsulfonyl group, 4-fluorophenylsulfonyl group, 4-
Examples thereof include a cyanophenylsulfonyl group, a 4-butoxyphenylsulfonyl group, a 4- (2-ethylhexyloxy) phenylsulfonyl group, and a 4-octadecylphenylsulfonyl group.

[0044] If the R ¹ to R ⁴ represents an alkyl phosphoryl groups, the alkyl phosphoryl groups represented by R ¹ to R ^4, include an alkyl phosphoryl groups having unsubstituted alkyl phosphoryl groups and substituents. As the alkylphosphoryl group represented by R ^{1 to} R ⁴ , an alkylphosphoryl group having a total of 2 to 40 carbon atoms is preferable, for example, a methylphosphoryl group, an ethylphosphoryl group, a propylphosphoryl group, an isopropylphosphoryl group, a butylphosphoryl group, Isobutyl phosphoryl group, sec-butyl phosphoryl group, t-butyl phosphoryl group, pentyl phosphoryl group, isopentyl phosphoryl group, hexyl phosphoryl group, heptyl phosphoryl group, octyl phosphoryl group, 2-ethylhexyl phosphoryl group, decyl phosphoryl group, dodecyl phosphoryl group Octadecylphosphoryl group, ethoxycarbonylmethylphosphoryl group, 2-ethylhexyloxycarbonylmethylphosphoryl group, aminocarbonylmethylphosphoryl group, N, N-dibutylaminocarbonyl Chiruhosuhoriru group, N- methylaminocarbonyl methyl phosphoryl group, N- ethylamino carbonyl methyl phosphoryl group, N- octyl aminocarbonylmethyl phosphoryl group, and a benzyl phosphoryl group.

[0045] If the R ¹ to R ⁴ represents an aryl phosphoryl groups, the aryl phosphoryl group represented by R ¹ to R ^4, include an aryl phosphoryl group having unsubstituted aryl phosphoryl group and a substituent. As the arylphosphoryl group represented by R ^{1 to} R ⁴ , an arylphosphoryl group having a total of 12 to 50 carbon atoms is preferable. For example, a phenylphosphoryl group, a 1-naphthylphosphoryl group, a 2-naphthylphosphoryl group, a 2-chlorophenylphosphoryl group Group, 2-methylphenyl phosphoryl group, 2-methoxyphenyl phosphoryl group, 2-butoxyphenyl phosphoryl group, 3-chlorophenyl phosphoryl group, 3-trifluoromethylphenyl phosphoryl group, 3-cyanophenyl phosphoryl group,
3- (2-ethylhexyloxy) phenyl phosphoryl group, 3-nitrophenyl phosphoryl group, 4-fluorophenyl phosphoryl group, 4-cyanophenyl phosphoryl group, 4-butoxyphenyl phosphoryl group, 4- (2-ethylhexyloxy) phenyl phosphoryl And 4-octadecylphenylphosphoryl group.

When R ^{1 to} R ⁴ represent an amino group, R ^{1 to} R ⁴
The amino group represented by represents an unsubstituted amino group and an amino group having a substituent. When R ^{1 to} R ⁴ represent an amino group having a substituent, the substituent is preferably an alkyl group or an aryl group. As the amino group represented by R ^{1 to} R ⁴ , an amino group having a total carbon number of 0 to 50 is preferable. For example, —NH ₂ , N-alkylamino group, N-arylamino group, N-acylamino group, -Sulfonylamino group, N, N-dialkylamino group, N, N-diarylamino group, N-alkyl-N-arylamino group, N, N-disulfonylamino group and the like. More specifically, N-methylamino group, N-ethylamino group, N-propylamino group, N-isopropylamino group, N-tertbutylamino group, N-hexylamino group, N-cyclohexylamino group, -Octylamino group, N-2-ethylhexylamino group, N-decylamino group, N-octadecylamino group, N-benzylamino group, N-phenylamino group, N-2-methylphenylamino group, N-2-chlorophenyl Amino group, N-2-methoxyphenylamino group, N-2-isopropoxyphenylamino group, N-2- (2-ethylhexyloxy)
Phenylamino group, N-3-chlorophenylamino group,
N-3-nitrophenylamino group, N-3-cyanophenylamino group, N-4-methoxyamino group, N-4-
(2′-ethylhexyloxy) phenylamino group, N
-4-cyanophenylamino group, N-methyl-N-phenylamino group, N, N-dimethylamino group, N, N-dibutylamino group, N, N-diphenylamino group, N, N
-Diacetylamino group, N, N-dibenzoylamino group, N, N- (dibutylcarbonyl) amino group, N, N
A-(di-2-ethylhexylcarbonyl) amino group,
N, N- (dimethylsulfonyl) amino group, N, N-
(Diethylsulfonyl) amino group, N, N- (dibutylsulfonyl) amino group, N, N- (2-ethylhexylsulfonyl) amino group, N, N- (diphenylsulfonyl) amino group and the like. The amino groups represented by R ^{1 to} R ⁴ include the following amino groups.

[0047]

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[0048]

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R¹~ R^FourIs a quaternary ammonium group
If R¹~ R^FourAs the quaternary ammonium group represented by
Tetramethylammonium, tetraethylammonium
System, benzyltrimethylammonium, dodecyltrime
Thilammonium is preferred. Quaternary ammonium group pair
The anion is Cl^-, Br^-, I^-, ClO_Four ^-, B
F_Four ^-, PF₆ ^-, HSO_Four ^-,

[0050]

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And the like.

R ^{1 to} R ⁴ are each —CO ₂ M _{1 / n} and —SO ₃
When M _{1 / n} is represented, M is Li, Na, K, Mg,
Ca, Ba, Al, Zn, Ni, Cu, or Fe is preferred. n is selected according to the valence of the metal atom,
Represents an integer of 4. The substituent of R ^{1 to} R ⁴ is -CO
_{In the case of 2} M _{1 / n} and —SO ₃ M _{1 / n} , preferred examples of M are the same as described above.

R ^{1 to} R ⁴ may be a divalent linking group,
Two hydrazone dye structures may be linked.

In the general formula (1), Ar represents an aryl group or a heterocyclic group. The aryl group represented by Ar includes an unsubstituted aryl group and an aryl group having a substituent. When Ar represents an alkyl group having a substituent, examples of the substituent include a halogen atom, an alkyl group, an aryl group, an acyl group, a carbamoyl group, a sulfamoyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, an acyloxy group, an alkoxy group, Aryloxy group, alkylthio group, arylthio group, alkylsulfonyl group, arylsulfonyl group, alkylphosphoryl group, arylphosphoryl group, amino group, -CN, -O
_{H, -CO 2 H, -SO 3} H, -NO 2, 4 quaternary ammonium groups, -CO ₂ M _{1 / n,} or include -SO ₃ M _{1 / n.} M represents a metal atom, and n represents an integer of 1 to 4. Further, as the aryl group, a benzene ring, a naphthalene ring,
And an anthracene ring.

When Ar represents an aryl group, preferred examples of Ar include the following monovalent groups.

[0056]

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[0057]

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When Ar represents an aryl group, Ar
Preferred examples include the following divalent groups.

[0059]

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The heterocyclic group represented by Ar includes an unsubstituted heterocyclic group and a substituted heterocyclic group. When Ar represents a heterocyclic group having a substituent, examples of the substituent include the same substituents as the examples of the substituent when Ar represents an aryl group having a substituent. Examples of the hetero ring constituting the hetero ring group include a 5-membered ring and a 6-membered hetero ring containing nitrogen, sulfur, oxygen or the like as a ring-constituting atom. For example, pyridine, thiophene, thiazole, furan, imidazole and the like can be mentioned, and these heterocycles may be condensed with another heterocycle or carbocycle.

When Ar represents a heterocyclic group, preferred examples of Ar include the following monovalent groups.

[0062]

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The compound represented by the general formula (1) has at least one water-soluble group in the molecule. The water-soluble group may be substituted at any position of the compound represented by the general formula (1). For example, R ^{1 to} R ^{4 of the} general formula (1) may be substituted.
A compound in which at least one of them represents a water-soluble group, a compound in which at least one of the substituents represents a water-soluble group when Ar in the general formula (1) represents an aryl group or a heterocyclic group having a substituent, and At least one of R ^{1 to} R ⁴
All compounds in which one is substituted with a water-soluble group are included. Since the compound represented by the general formula (1) has at least one water-soluble group in the molecule, it becomes an ink for inkjet recording using water or a mixed solvent of a water-soluble organic solvent and water. The compound represented by the general formula (1) preferably has two or more water-soluble groups in the molecule.

The water-soluble groups include —OH, —CO ₂
H, -SO ₃ H, 4 quaternary ammonium groups, -CO ₂ M _{1 /} n,
And preferably -SO ₃ M _{1 / n,} in particular, quaternary ammonium groups, -SO ₃ H, is -SO ₃ M _{1 / n,} preferred because a high solubility in water.

In the general formula (1), Ar is preferably represented by any of the general formulas (2) to (4).

In the general formula (2), R ⁵ and R ⁶ each independently represent a hydrogen atom, an alkyl group or an aryl group. The alkyl group and the aryl group represented by R ⁵ and R ⁶ have the same meanings as the alkyl group and the aryl group represented by R ^{1 to} R ^{4 in} the general formula (1), and specific examples are the same as those described above. Is mentioned.

R ^{7 to} R ¹⁰ are each independently a hydrogen atom, a halogen atom, an alkyl group, an aryl group, an acyl group, a carbamoyl group, a sulfamoyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, an acyloxy group, an alkoxy group, Aryloxy group, alkylthio group, arylthio group, alkylsulfonyl group, arylsulfonyl group, alkylphosphoryl group, arylphosphoryl group,
Amino _{group, -CN, -OH, -CO 2 H} , -SO 3 H, 4
Quaternary ammonium group, -CO ₂ M _{1 / n} , or -SO ₃ M _{1 / n}
Wherein M represents a metal atom, n represents an integer of ^{1 to 4} , and at least one of R ^{1 to} R ⁴ and R ^{7 to} R ¹⁰ represents a water-soluble group. For these substituents, R ^{1 to} R ⁴
Has the same meaning as each of the substituents represented by the following, and specific examples thereof include the same as those described above.

In the general formula (1), Ar represents the general formula
When represented by the formula (2), R¹~ R^Four, And R⁷~ R^Ten
At least one of which represents a water-soluble group, or
¹~ R ^Four, R^Five, R⁶, And R⁷~ R^TenAt least
One represents a group substituted with a water-soluble group. Preferably 2 or less
The upper part represents a water-soluble group or a group substituted with a water-soluble group. Previous
When the Ar moiety represented by the general formula (2) has a water-soluble group,
In this case, the water-soluble group is directly linked to the benzene ring in the general formula (2).
It does not need to be directly substituted, alkylene group, arylene
May be substituted on the benzene ring via a linking group such as a group
Then R^Five, R⁶, And R⁷~ R^TenOne of
May be replaced. Preferred water-soluble groups are the same as those described above.
It is like.

In the general formula (3), R ^{11 to} R ¹³ each independently represent a hydrogen atom, an alkyl group or an aryl group. The alkyl group and the aryl group represented by R ^{11 to} R ¹³ have the same meanings as the alkyl group and the aryl group represented by R ^{1 to} R ^{4 in} the general formula (1).
The same thing as the above is mentioned.

In the general formula (3), R ¹⁴ represents a hydrogen atom, a halogen atom, an alkyl group, an aryl group, an alkoxy group,
Aryloxy _{group, -OH, -CO 2 H, -SO} 3 H, 4
Quaternary ammonium group, -CO ₂ M _{1 / n} , or -SO ₃ M _{1 / n}
And M represents a metal atom, and n represents an integer of 1 to 4. When R ¹⁴ represents a halogen atom, chlorine or fluorine is preferred as the halogen atom. When R ¹⁴ represents an alkyl group or an aryl group, the alkyl group and the aryl group have the same meanings as the alkyl group and the aryl group represented by R ^{1 to} R ^{4 in} the general formula (1). The same thing as the above is mentioned. When R ¹⁴ represents an alkoxy group, R ¹⁴ is represented by —OR ²⁴ . R ²⁴ represents an alkyl group, which has the same meaning as the alkyl groups represented by R ^{1 to} R ^{4 in} the general formula (1), and specific examples thereof include the same ones as described above. When R ¹⁴ represents an aryloxy group, R ¹⁴ is represented by —OR ²⁵ . R ²⁵ represents an aryl group, which has the same meaning as the aryl groups represented by R ^{1 to} R ^{4 in} the general formula (1), and specific examples thereof include the same ones as described above. When R ¹⁴ represents a quaternary ammonium group, —CO ₂ M _{1 / n} , or —SO ₃ M _{1 / n} ,
It has the same meaning as each of the substituents represented by R ^{1 to} R ⁴ , and specific examples include the same as those described above.

In the general formula (3), X represents an oxygen atom or a sulfur atom.

When Ar in the general formula (1) is represented by the general formula (3), at least one of R ^{1 to} R ⁴ and R ¹⁴ represents a water-soluble group, or R ¹ to R ⁴ . R ⁴ ,
And at least one of R ^{11 to} R ¹⁴ represents a group substituted with a water-soluble group. Preferably, two or more represent a water-soluble group or a group substituted with a water-soluble group. When the Ar moiety represented by the general formula (3) has a water-soluble group, the water-soluble group does not need to directly substitute the benzene ring in the general formula (3), and may be an alkylene group or an arylene group. And the like, or a benzene ring may be substituted via a linking group, or any of R ^{11 to} R ¹⁴ may be further substituted. Preferred water-soluble groups are the same as described above.

In the general formula (4), R ¹⁵ represents a hydrogen atom or an alkyl group. The alkyl group represented by R ¹⁵ has the same meaning as the alkyl group represented by R ^{1 to} R ^{4 in} the general formula (1), and specific examples thereof include the same ones as described above.

In the general formula (4), R¹⁶And R¹⁷Is each
Each independently represents a hydrogen atom, a halogen atom, an alkyl group,
Reel group, alkoxy group, aryloxy group, alkyl
Thio group, arylthio group, -OH, -CO_TwoH, -SO_Three
H, quaternary ammonium group, -CO_TwoM_{1 / n}Or -SO
_ThreeM_{1 / n}And M represents a metal atom, and n is an integer of 1 to 4.
Represents R¹⁶And R¹⁷A halogen atom or alkyl represented by
Groups, aryl groups, alkoxy groups, and aryloxy
As for the group, R in the general formula (3)¹⁴Each position represented by
Synonymous with the substituent, and specific examples thereof are the same as those described above.
Is mentioned. R¹⁶And R¹⁷Represents an alkylthio group
If R¹⁶And R¹⁷Is -SR ²⁶It is represented by
R²⁶Represents an alkyl group, and R in the general formula (1)¹~ R^Four
Has the same meaning as the alkyl group represented by
And the same. R¹⁶And R¹⁷Is aryl
When representing a thio group, R¹⁶And R¹⁷Is -SR²⁸
It is represented by R²⁸Is an aryl group;
R of (1)¹~ R^FourHas the same meaning as the aryl group represented by
Examples include the same as described above.

In the general formula (4), Y represents an oxygen atom or a sulfur atom.

When Ar in the general formula (1) is represented by the general formula (4), R ^{1 to} R ⁴ and R ^{15 to} R ¹⁷
At least one of which represents a water-soluble group, or R ¹
~R ^4, R ^16, and at least one of R ¹⁷ represents a group substituted with a water-soluble group. Preferably, two or more represent a water-soluble group or a group substituted with a water-soluble group. When the Ar moiety represented by the general formula (4) has a water-soluble group, the water-soluble group does not need to directly substitute the benzene ring in the general formula (4), and may be an alkylene group or an arylene group. may be substituted on the benzene ring through a linking group such, R ¹⁵
To R ¹⁷ may be further substituted. Preferred water-soluble groups are the same as described above.

Specific examples of the compound represented by the general formula (1) are shown below, but the compounds used in the ink for ink-jet recording of the present invention are not limited to the following specific examples. Specific examples of the Ar portion of the compound represented by the general formula (1) are shown in Chemical Formulas 21 to 41 (1 to 4).
38) and specific examples (combinations of substituents R ^{1 to} R ⁴ ) of the pyrrolopyrimidine on ring portion are shown in Tables 1 to 25 ((1)
To (202)). Specific examples of the compound represented by the general formula (1) include, among various combinations of the specific examples 1 to 438 of the Ar portion and the specific examples (1) to (202) of the pyrrolopyrimidine on ring portion, Partial substituent or R ¹
To all the combinations containing a water-soluble group in any of R ⁴ to R ⁴ (for example, Compound 1- which is a combination of Specific Example 1 of the Ar moiety and Specific Example (193) of the pyrrolopyrimidine on ring)
(193) and the exemplified compound 10 in which the specific example 100 of the Ar moiety is combined with the specific example (1) of the pyrrolopyrimidione ring.
0- (1) and the like. The structures of the compounds are specified by using the same expressions for the exemplified compounds shown in Examples described later. )

[0078]

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[0079]

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[0080]

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[0081]

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[0082]

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[0083]

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[0084]

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[0085]

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[0086]

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[0087]

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[0088]

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[0089]

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[0090]

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[0091]

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[0092]

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[0093]

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[0094]

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[0095]

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[0096]

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[0097]

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[0098]

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[0099]

[Table 1]

[0100]

[Table 2]

[0101]

[Table 3]

[0102]

[Table 4]

[0103]

[Table 5]

[0104]

[Table 6]

[0105]

[Table 7]

[0106]

[Table 8]

[0107]

[Table 9]

[0108]

[Table 10]

[0109]

[Table 11]

[0110]

[Table 12]

[0111]

[Table 13]

[0112]

[Table 14]

[0113]

[Table 15]

[0114]

[Table 16]

[0115]

[Table 17]

[0116]

[Table 18]

[0117]

[Table 19]

[0118]

[Table 20]

[0119]

[Table 21]

[0120]

[Table 22]

[0121]

[Table 23]

[0122]

[Table 24]

[0123]

[Table 25]

In the ink for ink-jet recording of the present invention, the compound represented by the above general formula (1) is used in an amount of 0.2 to 0.2.
Preferably, the content is 10% by weight, and 0.5 to 5% by weight.
More preferably, it is contained.

The ink-jet recording ink of the present invention comprises:
Any form of oil-based ink, water-based ink, and solid ink may be used. Among them, the form of an aqueous ink is preferable.

When the ink for ink jet recording of the present invention is in the form of an oil-based ink, the compound represented by the general formula (1) is prepared by dissolving or dispersing the compound in a liquid medium containing an organic solvent as a main component. be able to. Examples of the organic solvent used for the liquid medium include alcohols such as ethanol, pentanol, heptanol, octanol, cyclohexanol, benzyl alcohol, phenylethyl alcohol, phenylpropyl alcohol, furfuryl alcohol, and anis alcohol; Ethyl ether, ethylene glycol monophenyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, propylene glycol monoethyl ether, propylene glycol monophenyl ether, dipropylene glycol monomethyl ether, dipropylene glycol monoethyl ether, triethylene glycol monoethyl ether, Ethylene glycol diacetate, ethylene glyco Monoethyl ether acetate, glycol derivatives such as propylene glycol diacetate;

Ketones such as benzyl methyl ketone, diacetone alcohol and cyclohexanone; ethers such as butyl phenyl ether, benzyl ethyl ether and hexyl ether; ethyl acetate, amyl acetate, benzyl acetate, phenyl ethyl acetate, phenyl ethyl acetate, phenoxy ethyl acetate;
Ethyl phenylacetate, benzyl propionate, ethyl benzoate, butyl benzoate, ethyl laurate, butyl laurate, isopropyl myristate, isopropyl palmitate, triethyl phosphate, tributyl phosphate, diethyl phthalate, dibutyl phthalate, malonic acid Diethyl, dipropyl malonate, diethyl diethylmalonate,
Diethyl succinate, dibutyl succinate, diethyl glutarate, diethyl adipate, dibutyl adipate, di (2-methoxyethyl) adipate, diethyl sebacate, diethyl maleate, dibutyl maleate, dioctyl maleate, diethyl fumarate, Esters such as dioctyl fumarate and 3-hexenyl cinnamate; hydrocarbon solvents such as petroleum ether, petroleum benzyl, tetralin, delican, 1-amylbenzene, dimethylnaphthalene; acetonitrile, formamide, N, N-dimethylformamide, N , N-dimethylacetamide, dimethylsulfoxide, sulfolane, propylene carbonate, N-methyl-2-pyrrolidone, N-vinyl-2-pyrrolidone, N, N-diethyldodecaneamide, and other polar solvents. These solvents may be used alone or as a mixture of two or more.

The compound represented by formula (1) may be dissolved in the organic solvent, or may be dispersed together with a suitable dispersant. For the method of preparing the oil-based ink, see JP-A-3-231975 and JP-T-5-50888.
Reference can be made to the method described in Japanese Patent Publication No.

When the ink for ink jet recording of the present invention is in the form of an aqueous ink, the compound represented by the general formula (1) is dissolved or dispersed in a mixed solvent consisting mainly of water and a water-soluble organic solvent. Can be prepared. Examples of the water-soluble organic solvent that can be used as a liquid medium for the aqueous ink include methanol, ethanol, propanol, isopropanol, butanol, and isobutanol.
sec-butanol, t-butanol, pentanol,
Alcohols such as hexanol, cyclohexanol and benzyl alcohol; ethylene glycol, diethylene glycol, triethylene glycol, polyethylene glycol, propylene glycol, dipropylene glycol, polypropylene glycol, butylene glycol, hexanediol, pentanediol, glycerin, hexanetriol, thiodithiol Polyhydric alcohols such as glycols; ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol monobutyl ether, propylene glycol monomethyl ether;
Glycol derivatives such as 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, and ethylene glycol monophenyl ether ;
Amines such as ethanolamine, diethanolamine, triethanolamine, N-methyldiethanolamine, N-ethyldiethanolamine, morpholine, N-ethylmorpholine, ethylenediamine, diethylenetriamine, triethylenetetramine, polyethyleneimine, and tetramethylpropylenediamine; formamide;
N, N-dimethylformamide, N, N-dimethylacetamide, dimethylsulfoxide, sulfolane, 2-pyrrolidone, N-methyl-2-pyrrolidone, N-vinyl-
Polar solvents such as 2-pyrrolidone, 2-oxazolidone, 1,3-dimethyl-2-imidazolidinone, acetonitrile, and acetone. The water-soluble organic solvent may be used in combination of two or more kinds together with water.

In a mixed solvent of water and the water-soluble organic solvent,
The compound represented by the general formula (1) may be dissolved or dispersed in the mixed solvent. When dispersing the compound in a mixed solvent, various dispersers (for example, ball mill, sand mill, attritor, roll mill, agitator mill, Henschel mixer, colloid mill, ultrasonic homogenizer, pearl mill, jet mill, ang mill, etc.) Preferably, the compound is used in the form of fine particles. After dissolving the dye in the organic solvent, the dye can be used by dispersing it in the above-mentioned mixed solvent using an appropriate dispersant or surfactant. For the method of preparing the aqueous ink, see JP-A-5-148436 and JP-A-5-295512.
Nos. 7-97541, 7-82515, 7-
Reference can be made to the method described in 118584 and the like.

When the ink for ink jet recording of the present invention is in the form of a solid ink, the compound represented by the general formula (1) is in a solid state at room temperature, and the energy supplied when the ink is ejected. And dissolved or dispersed in a phase change solvent that is melted to a liquid state. As the phase change solvent, for example, beeswax, carnauba wax, rice wax, wood wax,
Natural waxes such as jojoba oil, whale wax, candelilla wax, lanolin, montan wax, ozokerite, ceresin, paraffin wax, microcrystalline wax, petrolactam; polyethylene wax, chlorinated hydrocarbons, palmitic acid, stearyl acid, behenic acid,
Organic acids such as tigulinic acid, 2-acetonaphthobehenic acid, 12-hydroxystearic acid, dihydroxystearic acid; dodecanol, tetradecanol, hexadecanol, eicosanol, docosanol, tetracosanol, hexacosanol, octacosanol, dodecenol, Myricyl alcohol, tetracenol, hexadecenol, eicosenol, dococenol, pinene glycol, hinokiol, butynediol, nonanediol, isophthalyl alcohol, mesicerin, hexanediol, decanediol, tetradecanediol, hexadecanediol, docosandiol, tetracosanediol, Such as tvneol, phenylglycerin, eicosanediol, octanediol, and phenylpropylene glycol; Call the like;

Phenols such as bisphenol A and p-α-cumylphenol; organic acid esters of the above organic acids such as glycerin, ethylene glycol and diethylene glycol; cholesterol stearate, cholesterol palmitate, cholesterol myristate, cholesterol behenate; Cholesterol fatty acid esters such as cholesterol laurate and cholesterol melicate; saccharose stearate, saccharose palmitate, saccharose behenate, saccharose laurate, saccharose melinate, lactose stearate, lactose palmitate, lactose behenate, lactose laurate, melisin Sugar fatty acid esters such as acid lactose; benzoylacetone, diacetbenzene, benzophenone, Kosanon, heptacosanone,
Ketones such as heptatriacontanone, hentriacontanone, stearone, laurone; oleamide;
Lauric amide, stearic amide, ricinoleamide, palmitic amide, tetrahydrofuran amide, erucamide, myristic amide, 12-hydroxystearic amide, N-stearyl erucamide, N-oleyl stearamide, N , N-ethylenebislauric acid amide, N, N-ethylenebisstearic acid amide, N, N-ethylenebisbehenic acid amide, N, N-xylylenebisstearic acid amide,
N-butylenebisstearic acid amide, N, N-dioleyladipamide, N, N-dioleylsebacic amide, N, N-distearylsebacic amide,
N-distearyl terephthalamide, phenacetin,
Amides such as toluamide and acetamide; sulfonamides such as p-toluenesulfonamide, ethylbenzenesulfonamide and butylbenzenesulfonamide;
Is mentioned.

The phase change temperature of the phase change solvent from solid to liquid is preferably from 60 to 200 ° C., and from 80 to 15 ° C.
More preferably, it is 0 ° C. The solid ink may be prepared by dissolving the compound represented by the general formula (1) in the phase change solvent that has been melted by heating, or may be prepared by using an appropriate dispersant or binder in combination. It may be prepared by dispersing or dissolving. For the preparation method of solid ink,
Reference can be made to the methods described in JP-A-5-186723 and JP-A-7-70490.

A dye other than the compound represented by the general formula (1) may be added to the ink for inkjet recording of the present invention for the purpose of adjusting the hue and the like. Various additives may be added to the ink of the present invention, if desired. Examples of the additives include a viscosity adjuster, a surface tension adjuster, a specific resistance adjuster, a film adjuster, an ultraviolet absorber, an antioxidant, an antifading agent, a fungicide, a rust inhibitor, a dispersant, and a surfactant. And the like. When the inkjet recording ink of the present invention is in the form of a water-based ink or an oil-based ink, its viscosity is preferably adjusted to 40 cp or less, and its surface tension is preferably 20 dyn / cm to 10 dyn / cm.
It is preferably adjusted to 0 dyn / cm.

The ink-jet recording ink of the present invention comprises:
When the energy is applied, the liquid droplets are ejected to a recording medium, land on the recording medium, and form an image on the recording medium. The ink jet recording ink of the present invention may be applied to any type of ink jet printer. For example, it may be used for any of a continuous type and an on-demand type inkjet printer. There is no limitation on the type of the ink jet head, and the ink jet head can be preferably used for a printer having a head of any type, such as a bubble jet type, a thermal jet type, or a type using ultrasonic waves.

For example, a method of ejecting a large number of low-density inks called photo inks in a small volume, a method of improving image quality by using a plurality of inks having substantially the same hue and different densities, and a method of using colorless and transparent inks It can be used for many new types of inkjet recording type printers such as the type used. In particular, when the ink is used as a printer ink for forming an image close to a photograph by ejecting a large amount of ink having a high print speed and a low density, the improvement effect is remarkably exhibited.

Examples of the recording medium used in the image recording method of the present invention include plain paper, coated paper, plastic film and the like. It is preferable to use coated paper as the recording medium because the image quality and image storage durability are improved.

In the image recording method of the present invention, a recording paper containing a mordant may be used as a recording medium.
In particular, it is preferable to use a recording paper containing an immobilized polymer mordant. Examples of the polymer mordant include JP-A-48-28325, JP-A-54-74430, and JP-A-54-74430.
-124726, 55-22766, 55-1
No. 42339, No. 55-23850, No. 60-238
No. 51, No. 60-23852, No. 60-23853
No. 60-57836, No. 60-60643, No. 60-118834, No. 60-60643, No. 60
-118834, 60-122940, 60-
No. 122941, No. 60-122942, No. 60-2
No. 35134, JP-A-1-161236, U.S. Pat. Nos. 2,484,430, 2,548,564, 3,148,061, 3,309,690 and 4,115,124. Nos. 4,124,386, 4,193,800, 4,273,853, 4,282,305, and 4,450,224. . In particular, JP-A-1-161236
No. 2, pages 212 to 215, it is preferable to use a recording paper containing a polymer mordant. When an image is formed using a recording paper containing the polymer mordant, an image with excellent image quality is obtained and the light fastness of the image is improved.

In the image recording method of the present invention, a recording paper containing an inorganic pigment can be used as a recording medium. The type of the inorganic pigment is not particularly limited,
Any inorganic pigment can be used. For example, silica pigment, alumina pigment, titanium dioxide pigment, zinc oxide pigment, zirconium oxide pigment, mica-like iron oxide, lead white, lead oxide pigment, cobalt oxide pigment, strontium chromate, molybdenum pigment, smectite, magnesium oxide pigment, oxide Examples thereof include calcium pigments, calcium carbonate pigments, mullite, and the like, and one kind or two or more kinds can be used.

In the image recording method of the present invention, a recording paper containing various hydrophilic binders can be used as a recording medium. As the hydrophilic binder, any compound including gelatin or a derivative thereof, polyvinyl alcohol or a derivative thereof, polyalkylene oxide or a derivative thereof, and other superabsorbent polymers can be used. For example, those described in JP-A-1-161236, pp. 215 to 222, can be used. In the image recording method of the present invention, it is preferable to use a recording paper containing a matting agent as the recording material. As the matting agent, conventionally known matting agents can be used.
What is described on page 263-264 of 61236 can be used. In the image recording method of the present invention, recording paper hardened with a hardener can be used. There are no particular restrictions on the type of hardener, and known hardeners, for example, those described on page 222 of JP-A-1-161236 can be used.

Various surfactants can be used in the constituent layers of the recording medium for the purpose of improving coating properties, improving releasability, improving slipperiness, and preventing static charge. Specific examples of the surfactant are described in JP-A-62-173463 and JP-A-62-1.
No. 83457 and the like. Further, an organic fluoro compound may be included for the above purpose. Representative examples of the organic fluoro compound include JP-B-57-9053.
Nos. 8-17, JP-A-61-20994, 62-
Examples include fluorine-based surfactants described in each publication such as No. 135826, and hydrophobic fluorine compounds such as an oily fluorine-based compound such as fluorine oil or a solid fluorine-containing resin such as ethylene tetrafluoride resin.

The constituent layers (including the back layer) of the recording medium may contain various polymer latexes for the purpose of improving film physical properties such as dimensional stability, curl prevention, adhesion prevention and film crack prevention. Can be. Specifically, JP-A Nos. 62-245258 and 62-131648,
Any of the polymer latexes described in each gazette such as JP-A-62-10066 can be used. In particular, when a polymer latex having a low glass transition point (40 ° C. or lower) is used for the mordant layer, the mordant layer can be prevented from cracking and curl can be improved. An anti-curl effect is obtained. In the image recording method of the present invention, a constituent layer may contain an anti-fading agent. Anti-fading agents include, for example, antioxidants, ultraviolet absorbers, or certain metal complexes.
As an example, JP-A-1-161236, page 225-
What is described on page 247 can be used.

The recording medium may contain a fluorescent whitening agent. In particular, it is preferable that a fluorescent whitening agent is incorporated in the recording medium, or it is contained in ink or the like and supplied from the outside to the recording medium. In the present invention, the support of the recording medium is not particularly limited, but is a polyolefin (for example, polyethylene, polystyrene,
Paper laminated with a homopolymer such as polyethylene terephthalate or polybutene, or a copolymer of any combination thereof, or a plastic support (provided that a white pigment such as titanium oxide or zinc oxide, cobalt blue or ultramarine, It is preferable to add a coloring dye such as neodymium).

[0144]

[Ink A]

Dye (exemplified compound 102- (78)) 4 parts by weight (compound represented by formula (1)) diethylene glycol 9 parts by weight tetraethylene glycol monobutyl ether 9 parts by weight glycerin 7 parts by weight diethanolamine 1 part by weight water 70 parts by weight After stirring the above components for 1 hour while heating at 30 to 40 ° C., the target ink A was obtained by pressure filtration using a microfilter having an average pore diameter of 0.8 μm and a diameter of 47 mm.

Using the ink A thus produced, printing was performed on an ink jet paper manufactured by Fuji Photo Film Co., Ltd., Super Photo Grade (photo glossy paper) using an ink jet printer PM-700C (manufactured by Seiko Epson Corporation) to obtain an image sample.

The hue and light fastness were evaluated using the obtained image samples. The evaluation results are shown in Table 27 below. Evaluation of Hue The hue of the image part was visually evaluated. -Light resistance evaluation The image samples were irradiated with xenon light (85,000 lux) for 3 days using an "Atlas CI 65 weather meter", and the image densities before and after xenon irradiation were measured with a reflection densitometer ("X-Rite"). 310TR ”)
The dye remaining rate was calculated. The higher the residual dye ratio, the higher the light fastness. The reflection density before irradiation is 1, 1.5,
The evaluation was made at three points of 2.0, and at any concentration, the dye remaining rate was 80% or more, Δ, the case of 50 to 80% was Δ, and the other cases were evaluated as ×.

<Examples 2 to 5> Inks were produced in the same manner as in Example 1 except that the dyes (Exemplified Compound 102- (178)) used in Example 1 were replaced with the dyes shown in Table 26 below. Then, in the same manner as in Example 1, the hue and the light resistance were evaluated. The evaluation results are shown in Table 27 below.

[0148]

[Table 26]

Example 6 An ink was produced in the same manner as in Example 1 except that the dye (Example Compound 102- (178), 4 parts by weight) used in Example 1 was changed to the following dye. Dye (exemplified compound 102- (178)) 1.3 parts by weight Dye (compound represented by structural formula 1) 1.3 parts by weight Dye (compound represented by structural formula 2) 1.4 parts by weight The hue and light fastness of the ink thus obtained were evaluated in the same manner as in Example 1. The evaluation results are shown in Table 27 below.

[0150]

Embedded image

[0151]

[Table 27]

[0152]

According to the present invention, it is possible to provide an ink jet recording ink and an image recording method capable of forming an image having good hue and light fastness.

Continuation of the front page (72) Inventor Tomohiro Kodama 200-Onakazato, Fujinomiya-shi, Shizuoka Fuji Photo Film F Co., Ltd. F-term (reference) 2C056 EA13 FC01 2H086 BA02 BA55 4J039 BA29 BA30 BA31 BC05 BC07 BC12 BC16 BC19 BC20 BC29 BC31 BC33 BC36 BC44 BC47 BC50 BC51 BC52 BC53 BC54 BC55 BC65 BC66 BC73 BC75 BC77 BC79 EA35 GA24

Claims (6)

[Claims] 1. An ink jet recording ink containing a compound represented by the following general formula (1). Embedded image (In the general formula (1), Ar represents an aryl group or a heterocyclic group, and R ^{1 to} R ⁴ each independently represent a hydrogen atom, a halogen atom, an alkyl group, an aryl group, an acyl group, a carbamoyl group, a sulfamoyl group. Group, alkoxycarbonyl group, aryloxycarbonyl group, acyloxy group, alkoxy group, aryloxy group, alkylthio group, arylthio group, alkylsulfonyl group, arylsulfonyl group, alkylphosphoryl group, arylphosphoryl group,
Amino _{group, -CN, -OH, -CO 2 H} , -SO 3 H, 4
Quaternary ammonium group, -CO ₂ M _{1 / n} , or -SO ₃ M _{1 / n}
Wherein M represents a metal atom, n represents an integer of 1 to 4, and the compound represented by the general formula (1) has at least one water-soluble group in the molecule. ) 2. In the general formula (1), Ar represents the following general formula:
The ink jet according to claim 1, which is a group represented by (2).
Recording ink. Embedded image(In the general formula (2), R^Five, R⁶Is each independently hydrogen
Represents an atom, an alkyl group, or an aryl group;⁷~ R
^TenAre each independently a hydrogen atom, a halogen atom, an alkyl
Group, aryl group, acyl group, carbamoyl group, sulfa
Moyl group, alkoxycarbonyl group, aryloxyca
Rubonyl group, acyloxy group, alkoxy group, aryl
Oxy group, alkylthio group, arylthio group, alkyl
Sulfonyl group, arylsulfonyl group, alkylphospho
Ryl group, aryl phosphoryl group, amino group, -CN,-
OH, -CO_TwoH, -SO_ThreeH, quaternary ammonium group,-
CO _TwoM_{1 / n}Or -SO_ThreeM_{1 / n}And M is a metal atom
And n represents an integer of 1 to 4. ) 3. The ink for inkjet recording according to claim 1, wherein Ar is a group represented by the following general formula (3). Embedded image (In the general formula (3), R ^{11 to} R ¹³ each independently represent a hydrogen atom, an alkyl group, or an aryl group, and R ¹⁴ represents a hydrogen atom, a halogen atom, an alkyl group, an aryl group, an alkoxy group, an aryl group. oxy group, -OH, -CO ₂ H, -S
O ₃ H, quaternary ammonium group, —CO ₂ M _{1 / n} , or —
SO ₃ M _{1 / n} , M represents a metal atom, n represents an integer of 1 to 4, and X represents an oxygen atom or a sulfur atom. ) 4. The ink for inkjet recording according to claim 1, wherein Ar is a group represented by the following general formula (4). Embedded image (In the general formula (4), R ¹⁵ represents a hydrogen atom or an alkyl group, and R ¹⁶ and R ¹⁷ each independently represent a hydrogen atom, a halogen atom, an alkyl group, an aryl group, an alkoxy group, an aryloxy group, an alkylthio group. Group, arylthio group,-
_{OH, -CO 2 H, -SO 3} H, 4 quaternary ammonium group, -
Represents CO ₂ M _{1 / n} or —SO ₃ M _{1 / n} , M represents a metal atom, n represents an integer of 1 to 4, and Y represents an oxygen atom or a sulfur atom. ) 5. The method according to claim 1, wherein the water-soluble group is —CO ₂ H, —SO ₃ H, a quaternary ammonium group, —CO ₂ M _{1 / n} or —SO ₃ M _{1 / n.} The ink for inkjet recording according to any one of the above. 6. Any one of claims 1 to 5
The energy is supplied to the ink jet recording ink according to the item, and the ink droplets are ejected to a recording medium,
An image recording method for recording an image composed of the ink on a recording medium.