JP2001234104A - Oil based ink composition - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain an oil based ink composition which has a good hue, a sharp absorption spectrum, and a good color purity and can form an image having a high stock stability such as light fastness, and the like. SOLUTION: This oil based ink composition contains an oil solvent and a compound of general formula (1). In general formula (1), Ar is an aryl group or a hetero cyclic group; and X1-X5 are each carbon or nitrogen atom which can form an unsaturated hetero 5-member ring.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

The present invention relates to an oil-based ink composition, and more particularly, to an oil-based ink composition utilizing a hydrazone dye having a specific structure.

[0002]

2. Description of the Related Art An oil-based ink composition is generally a composition in which a colorant is dispersed or dissolved in an oil-based medium. Conventionally, various dyes have been used as the colorant. However, when a conventional dye is used, there are problems such as that the hue of the oil-based ink composition is slightly unclear and light fastness is poor. In addition, since the dispersibility or dissolution stability of the dye in the oil medium is insufficient, when the oil ink composition is stored for a long period of time, the dye may be decolorized or discolored or separated from the oil medium. .

[0003]

SUMMARY OF THE INVENTION An object of the present invention is to provide an oil-based ink composition which can form an image having good hue and high storage stability such as light fastness.

[0004]

Means for solving the above problems are as follows. That is, <1> an oil-based ink composition comprising an oil-based medium and a compound represented by the following general formula (1).

[0005]

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(In the general formula (1), Ar represents an aryl group or a heterocyclic group, and X ^{1 to} X ⁵ each independently represent a carbon atom or a nitrogen atom capable of forming an unsaturated 5-membered heterocyclic ring. <2> The oil-based ink composition according to <1>, wherein the compound represented by the general formula (1) is a compound represented by the following general formula (2).

[0007]

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(In the general formula (2), Ar represents an aryl group or a heterocyclic group, and R ^{1 to} R ³ each independently represent a hydrogen atom, an aryl group, an alkyl group, a heterocyclic group, an acyl group. A carbamoyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, a sulfamoyl group, an alkylsulfonyl group, an arylsulfonyl group, an acyloxy group,
Represents an alkoxy group, an aryloxy group, an alkylthio group, an arylthio group, an amino group, or —OH. <3> The oil-based ink composition according to <1>, wherein the compound represented by the general formula (1) is a compound represented by the following general formula (3).

[0009]

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(In the general formula (3), Ar represents an aryl group or a heterocyclic group, and R ^{1 to} R ⁴ represent the general formula (2)
It has the same meaning as R ^{1 to} R ³ in. <4> The oil-based ink composition according to <1>, wherein the compound represented by the general formula (1) is a compound represented by the following general formula (4).

[0011]

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(In the general formula (4), Ar represents an aryl group or a heterocyclic group, and R ^{1 to} R ³ represent the general formula (2)
Has the same meaning as R ^{1 to} R ³ in the formula, and R represents a substituent having a Hammett's substituent constant σ _p of 0.3 to 1.5. <5> The oil-based ink composition according to <1>, wherein the compound represented by the general formula (1) is a compound represented by the following general formula (5).

[0013]

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[0014] (In the general formula (5), Ar represents an aryl group or a heterocyclic group, R ¹ and R ³ have the same meanings as R ¹ to R ³ in the general formula (2).) <6> The oil-based ink composition according to <1>, wherein the compound represented by the general formula (1) is a compound represented by the following general formula (6).

[0015]

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[0016] In (Formula (6), Ar represents an aryl group or a heterocyclic group, R ¹ and R ³ have the same meanings as R ¹ to R ³ in the general formula (2), R , Hammet
Represents a substituent having a substituent constant σ _p of 0.3 to 1.5. <7> In the general formula (1), Ar represents the following general formula (7)
The oil-based ink composition according to any one of <1> to <6>, which is a group represented by the formula:

[0017]

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(In the general formula (7), R ⁵ and R ⁶ each independently represent a hydrogen atom, an alkyl group or an aryl group, and R ^{7 to} R ¹⁰ each independently represent a hydrogen atom A halogen atom, an alkyl group, an aryl group, an acyl group, a carbamoyl group, a sulfamoyl group, an alkoxycarbonyl group,
Represents an aryloxycarbonyl group, an acyloxy group, an alkoxy group, an aryloxy group, an alkylthio group, an arylthio group, an alkylsulfonyl group, an arylsulfonyl group, an alkylphosphoryl group, an arylphosphoryl group, an amino group, -CN, or -OH. <8> In the general formula (1), Ar represents the following general formula (8)
The oil-based ink composition according to any one of <1> to <6>, which is a group represented by the formula:

[0019]

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(In the general formula (8), 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 or an aryl group. , An alkoxy group, an aryloxy group, or -O
H represents X and X represents an oxygen atom or a sulfur atom. <9> In the general formula (1), Ar represents the following general formula (9)
The oil-based ink composition according to any one of <1> to <6>, which is a group represented by the formula:

[0021]

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(In the general formula (9), 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, Represents an aryloxy group, an alkylthio group, an arylthio group, or -OH, and Y represents an oxygen atom or a sulfur atom.)

[0023]

BEST MODE FOR CARRYING OUT THE INVENTION Hereinafter, the present invention will be described in detail. The oil-based ink composition of the present invention has the general formula (1)
Is contained as a dye. The compound represented by the general formula (1) can have various tautomeric structures, and the compound represented by the general formula (1) in the present invention includes these tautomers. . The compound represented by the general formula (1) has good hue, sharp absorption spectrum, good color purity, and good light fastness. Therefore, when an image is formed using the oil-based ink composition of the present invention, the formed image has a good hue and the light stability of the image area is high. Also,
Since the compound has a good affinity for an oily medium,
The oil-based ink composition of the present invention has good storage stability even when stored for a long time without separation of the oil-based medium and the dye.

In the general formula (1), X ^{1 to} X ⁵ each independently represent a carbon atom or a nitrogen atom capable of forming a 5-membered unsaturated heterocyclic ring. Each includes an unsubstituted carbon atom and a nitrogen atom, and a substituted carbon atom and a nitrogen atom. Among the compounds represented by the general formula (1), the compound represented by the general formula (2)
The compounds represented by the formulas (6) to (6) are preferable, the compounds represented by the formula (2) and the compounds represented by the formula (3) are more preferable, and the compounds represented by the formula (2) are particularly preferable. Are preferred. However, the compound represented by the general formula (1) is not limited to the compounds represented by the general formulas (2) to (6).

In the above general formulas (2) to (6), R ^{1 to} R
⁴ is each independently a hydrogen atom, an aryl group, an alkyl group, a heterocyclic group, an acyl group, a carbamoyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, a sulfamoyl group, an alkylsulfonyl group, an arylsulfonyl group, an acyloxy group, Represents an alkoxy group, an aryloxy group, an alkylthio group, an arylthio group, an amino group, or —OH.

[0026] In the general formula (2) to (6), if R ¹ to R ⁴ represents an aryl group, the aryl group represented by R ¹ to R ^4, an unsubstituted aryl group and substituents Aryl groups are included. 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 carbonyl group, a substituted sulfamoyl group, and a substituted Amino group, substituted oxycarbonyl group, substituted oxysulfonyl group, alkylthio group, arylthio group, alkylsulfonyl group, arylsulfonyl group, aryl group, hydroxy group, acyl group, acyloxy group, substituted sulfonyloxy group, substituted aminocarbonyloxy group, And substituted phosphoryloxy groups.

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-dichlorophenyl group, 3,5-dichlorophenyl group, 3,4-dimethoxyphenyl group , 3,5
-A dibutoxyphenyl group,

3-octyloxyphenyl group, 3- (dibutylaminocarbonylmethoxy) phenyl group,
(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 Oxyphenyl groups and the like can be mentioned.

[0029] In the general formula (2) to (6), if R ¹ to R ⁴ represents a heterocyclic group, the heterocyclic group represented by R ¹ to R ^4, unsubstituted heterocyclic group and substituted Heterocyclic groups having groups are included. When R ^{1 to} R ⁴ represent a heterocyclic 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, Examples include an acyloxy group, an alkoxy group, an aryloxy group, an alkylthio group, an arylthio group, an alkylsulfonyl group, an arylsulfonyl group, an alkylphosphoryl group, an arylphosphoryl group, an amino group, and -CN. Examples of the hetero ring constituting the hetero ring group include nitrogen, sulfur, oxygen, and the like as ring-constituting atoms.
And six-membered heterocycles. For example, pyridine, thiophene, thiazole, furan, imidazole and the like can be mentioned, and these heterocycles may be condensed with another heterocycle or carbocycle. Specific examples of the heterocyclic group represented by R ^{1 to} R ⁴ include, for example, the following heterocyclic groups.

[0030]

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[0031] In the general formula (2) to (6), if R ¹ to R ⁴ represents an alkyl group, the alkyl group represented by R ¹ to R ^4, an unsubstituted alkyl group and substituents Includes alkyl groups. When R ^{1 to} R ⁴ represent 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 may be further substituted with an alkyl group, an alkoxy group, a nitro group, a cyano group, a hydroxy group, a halogen atom, or the like.

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 group, 1- (2,4-di-t-pentylphenyloxy)
Propyl group, 2,4-di-t-pentylphenyloxyethyloxycarbonylpropyl group, naphthyloxyethyloxycarbonylethyl group, N-methyl-N-phenylethyloxycarbonylethyl group, methanesulfonylaminopropyl group and the like. .

In the general formulas (2) to (6), R¹~ R^FourBut reed
R represents a group¹~ R^FourThe acyl group represented by
Includes substituted acyl groups and substituted acyl groups
You. R ¹~ R^FourRepresents an acyl group having a substituent,
Examples of the substituent include an alkoxy group, an aryloxy group,
Logen atom, alkylthio group, arylthio group, anili
Nono groups are preferred. R¹~ R^FourAs an acyl group represented by
Is preferably an acyl group having 2 to 20 carbon atoms.
Acetyl, propanoyl, butanoyl,
Sanoyl group, octanoyl group, 2-ethylhexanoyl
Group, decanoyl group, dodecanoyl group, octadecanoyl
Group, 2-cyanopropanoyl group, 1,1-dimethylpro
And a panoyl group. Also, R¹~ R^FourRepresented by
Examples of the acyl group also include the following acyl groups.

[0034]

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[0035] In the general formula (2) to (6), if R ¹ to R ⁴ represents a carbamoyl group, a carbamoyl group represented by R ¹ to R ^4, an unsubstituted carbamoyl group and substituents Includes carbamoyl groups. When R ^{1 to} R ⁴ represent a carbamoyl group having a substituent, the substituent is preferably an alkyl group or an aryl group. The carbamoyl group represented by R ^{1 to} R ⁴ is preferably a carbamoyl group having a total of 1 to 30 carbon atoms, for example, N-methylcarbamoyl group, N
-Ethylcarbamoyl group, N-propylcarbamoyl group, N-butylcarbamoyl group, N-hexylcarbamoyl group, N-cyclohexylcarbamoyl group, 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, N, N-diphenylcarbamoyl and the like. . Examples of the carbamoyl group represented by R ^{1 to} R ⁴ include the following carbamoyl groups.

[0036]

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In the general formulas (2) to (6), R¹~ R^FourIs al
When representing a oxycarbonyl group, R ¹~ R^FourA represented by
Unsubstituted alkoxy carboxy groups
And a substituted alkoxycarbonyl group.
I will. R¹~ R^FourHaving a substituent
When representing an alkyl group, an alkyl group (the alkyl
Group) as a substituent, a halogen atom, an alkoxy group,
Aryloxy groups are preferred. R¹~ R^FourAl represented by
The oxycarbonyl group includes an alkyl group having 2 to 20 carbon atoms.
A oxycarbonyl group is preferred, for example, methoxycarbonyl
Bonyl, ethoxycarbonyl, propoxycarbonyl
Group, butoxycarbonyl group, hexyloxycarboni
Group, 2-ethylhexyloxycarbonyl group, octyl
Ruoxycarbonyl group, decyloxycarbonyl group,
Kutadecyloxycarbonyl group, phenyloxyethyl
Oxycarbonyl group, phenyloxypropyloxyca
Rubonyl group, 2,4-di-t-amylphenyloxy
Tylcarbonyl group, 2,6-di-t-butyl-4-methyl
Rucyclohexyloxycarbonyl group, isostearyl
An oxycarbonyl group;

In the general formulas (2) to (6), R¹~ R^FourAnts
When it represents a carbonyloxy group, R¹~ R^FourRepresented by
Aryloxycarbonyl groups include unsubstituted aryl
Aryloxy having an oxycarbonyl group and a substituent
Includes carbonyl groups. R ¹~ R^FourHas a substituent
When representing a reeloxycarbonyl group, an aryl group (A
As the substituent for the aryl group of the reeloxy moiety), halo
Gen atom, alkyl group, alkoxy group, acylamino group
Is preferred. R¹~ R^FourAryloxycarbo represented by
As the phenyl group, aryloxyca having a total of 7 to 30 carbon atoms is used.
A rubonyl group is preferred, for example, 2-methylphenylo
Xycarbonyl group, 2-chlorophenyloxycarboni
A 2,6-dimethylphenyloxycarbonyl group,
2,4,6-trimethylphenyloxycarbonyl group,
2-methoxyphenyloxycarbonyl group, 2-butoki
Cyphenyloxycarbonyl group, 3-cyanophenylo
Xycarbonyl group, 3-nitrophenyloxycarboni
Group, 2,2-ethylhexylphenyloxycarbonyl
Group, 3- (2-ethylhexyloxy) phenyloxy
Sicarbonyl group, 4-fluorophenyloxycarboni
Group, 4-chlorophenyloxycarbonyl group,
Anophenyloxycarbonyl group, 4-butoxyphenyl
And a luoxycarbonyl group.

[0039] In the general formula (2) to (6), if R ¹ to R ⁴ is a sulfamoyl group, a sulfamoyl group represented by R ¹ to R ^4, an unsubstituted sulfamoyl group and a substituted group Includes sulfamoyl groups. 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 A dialkylsulfamoyl group,
N, N-diarylsulfamoyl group, N-alkyl-
And N-arylsulfamoyl groups. More specifically, N-methylsulfamoyl, N-ethylsulfamoyl, N-propylsulfamoyl, N-
Butylsulfamoyl group, N-hexylsulfamoyl group, N-cyclohexylsulfamoyl group, N-octylsulfamoyl group, N-2-ethylhexylsulfamoyl group, N-decylsulfamoyl group, N- Octadecylsulfamoyl group, N-phenylsulfamoyl group, N-2-methylphenylsulfamoyl group, N-2
-Chlorophenylsulfamoyl group, N-2-methoxyphenylsulfamoyl group, N-2-isopropoxyphenylsulfamoyl group, N-2- (2-ethylhexyloxy) phenylsulfamoyl group, N-3- Chlorophenylsulfamoyl 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-
And a di- (2-ethylhexyl) sulfamoyl group.

[0040] In the general formula (2) to (6), if R ¹ to R ⁴ represents an alkylsulfonyl group, the alkylsulfonyl group represented by R ¹ to R ^4, unsubstituted alkylsulfonyl group and a substituted And alkylsulfonyl groups having a 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.

[0041] In the general formula (2) to (6), if R ¹ to R ⁴ represents an aryl sulfonyl group, the arylsulfonyl group represented by R ¹ to R ^4, unsubstituted arylsulfonyl group and a substituted And arylsulfonyl groups having a group.
When R ^{1 to} R ⁴ represent an arylsulfonyl group having a substituent, the substituent is preferably a halogen atom, an alkoxy group, an aryloxy group, a cyano group, a trifluoromethyl group, or a nitro group. 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-
A (2-ethylhexyloxy) phenylsulfonyl group,
3-nitrophenylsulfonyl group, 4-fluorophenylsulfonyl group, 4-cyanophenylsulfonyl group, 4
-Butoxyphenylsulfonyl group, 4- (2-ethylhexyloxy) phenylsulfonyl group, 4-octadecylphenylsulfonyl group and the like.

[0042] In the general formula (2) to (6), if R ¹ to R ⁴ represents an acyloxy group, the acyloxy group represented by R ¹ to R ^4, an unsubstituted acyloxy group and substituents Includes acyloxy groups. 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 a carbonyloxy group, an octanoyloxy group, a decanoyloxy group, an undecanoyloxy group, and an octadecanoyloxy group.

[0043] In the general formula (2) to (6), if R ¹ to R ⁴ represents an alkoxy group, the alkoxy group represented by R ¹ to R ^4, an unsubstituted alkoxy group and substituents Includes alkoxy groups. When R ^{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-
Examples include an ethylaminocarbonylmethyloxy group, an N-octylaminocarbonylmethyloxy group, an N-methyl-N-benzylaminocarbonylmethyloxy group, a benzyloxy group, a cyanomethyloxy group, and the like.

[0044] In the general formula (2) to (6), if R ¹ to R ⁴ represents an aryloxy group, the aryloxy group represented by R ¹ to R ^4, unsubstituted aryloxy group, and a substituted And aryloxy groups having groups. 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 of 6 to 30 carbon atoms is preferable. For example, a phenyloxy group, a 1-naphthyloxy group, a 2-naphthyloxy group, a 2-chlorophenyloxy group 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-nitrophenyloxy group, 4-fluorophenyloxy group, 4-cyanophenyloxy group, 4-butoxyphenyloxy group,
-(2-ethylhexyloxy) phenyloxy group, 4
-Octadecylphenyloxy group and the like.

[0045] In the general formula (2) to (6), if R ¹ to R ⁴ represents an alkylthio group, the alkylthio group represented by R ¹ to R ^4, an unsubstituted alkylthio group and substituents Includes alkylthio groups. 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-ethylhexyloxy Carbonylmethylthio group, aminocarbonylmethylthio group,
N, N-dibutylaminocarbonylmethylthio, N-methylaminocarbonylmethylthio, N-ethylaminocarbonylmethylthio, N-octylaminocarbonylmethylthio, N-methyl-N-benzylaminocarbonylmethylthio, benzylthio, cyano And a methylthio group.

[0046] In the general formula (2) to (6), if R ¹ to R ⁴ is an arylthio group, the arylthio group represented by R ¹ to R ^4, an unsubstituted arylthio group and substituents Arylthio groups are included. When R ^{1 to} R ⁴ represent an arylthio group having a substituent, the substituent is preferably a halogen atom, an alkyl group, an aryloxy group, an alkoxy group, a cyano group, a trifluoromethyl group, or a nitro group. As the arylthio group represented by R ^{1 to} R ⁴ , an arylthio group having a total carbon number of 6 to 30 is preferable.
Phenylthio, 1-naphthylthio, 2-naphthylthio, 2-chlorophenylthio, 2-methylphenylthio, 2-methoxyphenylthio, 2-butoxyphenylthio, 3-chlorophenylthio, 3-trifluoro Methylphenylthio, 3-cyanophenylthio, 3- (2-ethylhexyloxy) phenylthio, 3-nitrophenylthio, 4-fluorophenylthio, 4-cyanophenylthio, 4-butoxyphenylthio , 4- (2-ethylhexyloxy) phenylthio group, 4-octadecylphenylthio group and the like.

In the general formulas (2) to (6), R¹~ R^FourIs Ami
When representing a group, R¹~ R^FourThe amino group represented by
Includes substituted amino groups and substituted amino groups
You. R ¹~ R^FourRepresents an amino group having a substituent,
As the substituent, an alkyl group and an aryl group are preferable.
R¹~ R^FourThe amino group represented by
An amino group of 0 is preferred, for example, -NH_Two, N-Al
Killamino group, N-arylamino group, N-acylamino
Group, N-sulfonylamino group, N, N-dialkyl
Mino 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,
N-octylamino group, N-2-ethylhexylamino
Group, N-decylamino group, N-octadecylamino group,
N-benzylamino group, N-phenylamino group, N-2
-Methylphenylamino group, N-2-chlorophenyla
Mino group, N-2-methoxyphenylamino group, N-2-
Isopropoxyphenylamino group, N-2- (2-ethyl
Ruhexyloxy) phenylamino group, N-3-chloro
Phenylamino group, N-3-nitrophenylamino group,
N-3-cyanophenylamino group, N-4-methoxya
Amino group, N-4- (2'-ethylhexyloxy)
Nylamino group, N-4-cyanophenylamino group, N-
Methyl-N-phenylamino group, N, N-dimethylamino
Group, N, N-dibutylamino group, N, N-diphenyl
Amino group, N, N-diacetylamino group, N, N-dibe
Nzoylamino group, N, N- (dibutylcarbonyl) a
Amino group, N, N- (di-2-ethylhexylcarboni
L) amino group, N, N- (dimethylsulfonyl) amino
Group, N, N- (diethylsulfonyl) amino group, N, N
-(Dibutylsulfonyl) amino group, N, N- (2-E
Tylhexylsulfonyl) amino group, N, N- (dife
Nylsulfonyl) amino group and the like. Also, R¹
~ R^FourAs the amino group represented by the following amino group also
No.

[0048]

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[0049]

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In the general formulas (4) and (6), R is Ham
represents a substituent having a substituent constant [sigma] _p of 0.3 to 1.5, which includes a cyano group, a nitro group, a sulfonyl group (for example, octylsulfonyl, phenylsulfonyl, trifluoromethylsulfonyl, pentane). Fluorophenylsulfonyl, etc.), β-carboxyvinyl group, sulfinyl group (eg, t-butylsulfinyl, tolylsulfinyl, trifluoromethylsulfinyl, pentafluorophenylsulfinyl, etc.), β, β-dicyanovinyl group, alkyl halide group ( For example, trifluoromethyl, perfluorooctyl, ω-hydroperfluorododecyl, etc.), formyl group, carboxyl group, carbonyl group (eg, acetyl, pivaloyl, benzoyl, trifluoroacetyl, etc.), alkyl or aryloxycarbonyl group (eg, If, ethoxycarbonyl, phenoxycarbonyl, etc.), 1-tetrazolyl group, 5-chloro-1-tetrazolyl group, a carbamoyl group (e.g.,
Dodecylcarbamoyl, phenylcarbamoyl, etc.), sulfamoyl group (eg, trifluoromethylsulfamoyl, phenylsulfamoyl, ethylsulfamoyl, etc.). Among them, a cyano group, a sulfonyl group, a sulfinyl group, a trifluoromethyl group, an alkyl or aryloxycarbonyl group, a carbamoyl group and a sulfamoyl group are preferable, and a cyano group and a sulfonyl group are particularly preferable.

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

In the general formulas (1) to (6), 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 aryl 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, and an alkoxy group. , An aryloxy group, an alkylthio group, an arylthio group, an alkylsulfonyl group, an arylsulfonyl group, an alkylphosphoryl group, an arylphosphoryl group, an amino group, -CN, or -OH. Further, as the aryl group,
Examples include 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.

[0054]

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[0055]

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

[0057]

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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.

[0060]

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In the general formulas (1) to (6), Ar is represented by the general formula (7), the general formula (8) or the general formula (9). Preferred)

In the general formula (7), 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 formulas (2) to (6), respectively. And the same as those described above.

In the general formula (7), R ^{7 to} R ¹⁰ each independently represent 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 aryloxy group. Carbonyl group, acyloxy group, alkoxy group, aryloxy group, alkylthio group, arylthio group, alkylsulfonyl group, arylsulfonyl group, alkylphosphoryl group, arylphosphoryl group, amino group, -CN, or-
Represents OH. These substituents have the same meanings as the respective substituents represented by R ^{1 to} R ⁴ in the general formulas (2) to (6), and specific examples thereof include the same ones as described above. However, when R ^{7 to} R ¹⁰ represent a halogen atom, an alkylphosphoryl group, or an arylphosphoryl group,
Specific examples thereof include the following.

When R ^{7 to} R ¹⁰ 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.

[0065] If the R ⁷ to R ¹⁰ represents an alkyl phosphoryl groups, the alkyl phosphoryl groups represented by R ⁷ to R ^10, include alkyl phosphoryl groups having unsubstituted alkyl phosphoryl groups and substituents. The alkyl phosphoryl groups represented by R ⁷ to R ^10, alkyl phosphoryl group having a total carbon number of 2 to 40 is preferred, for example, Mechiruhosuhoriru group, Echiruhosuhoriru group, propyl phosphoryl group, isopropyl phosphoryl group, Buchiruhosuhoriru 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, octadecyl phosphoryl group, ethoxycarbonylmethyl phosphoryl group, 2-ethylhexyloxycarbonylmethyl phosphoryl group, Aminocarbonylmethylphosphoryl group, N, N-dibutylaminocarbonylmethylphosphoryl group, N-methylaminocarbonylmethylphosphoryl group, N-ethylaminocarbonylmethylphosphoryl group, N-octylaminocarbonylmethylphosphoryl group, benzylphosphoryl group and the like. Can be

[0066] If the R ⁷ to R ¹⁰ represents an aryl phosphoryl groups, the aryl phosphoryl group represented by R ⁷ to R ^10, include an aryl phosphoryl group having unsubstituted aryl phosphoryl group and a substituted group. The aryl phosphoryl group represented by R ⁷ to R ^10, total carbon number 12 to 50
Arylphosphoryl group is preferable, for example, phenylphosphoryl group, 1-naphthylphosphoryl group, 2-naphthylphosphoryl group, 2-chlorophenylphosphoryl group,
-Methylphenylphosphoryl group, 2-methoxyphenylphosphoryl group, 2-butoxyphenylphosphoryl group, 3
-Chlorophenylphosphoryl group, 3-trifluoromethylphenylphosphoryl group, 3-cyanophenylphosphoryl group, 3- (2-ethylhexyloxy) phenylphosphoryl group, 3-nitrophenylphosphoryl group, 4-fluorophenylphosphoryl group, 4-cyano Phenylphosphoryl group, 4-butoxyphenylphosphoryl group, 4- (2
-Ethylhexyloxy) phenylphosphoryl group, 4-
And octadecylphenylphosphoryl group.

In the general formula (8), 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 formulas (2) to (6), respectively. And the same as those described above.

In the general formula (8), R¹⁴Is a hydrogen atom,
Halogen atom, alkyl group, aryl group, alkoxy
Group, an aryloxy group, or -OH. R¹⁴Is halo
When a halogen atom is represented, chlorine and fluorine
N2 is preferred. R¹⁴Represents an alkyl group or an aryl group.
The alkyl group and the aryl group,
R in general formulas (2) to (6)¹~ R^FourAnd an alkyl group represented by
And aryl groups have the same meanings, respectively, and as specific examples,
And the same. R¹⁴Represents an alkoxy group
If R¹⁴Is -OR^{twenty four}It is represented by R^{twenty four}Represents an alkyl group
And represents R in the general formulas (2) to (6)¹~ R^FourRepresented by
It has the same meaning as the alkyl group, and specific examples thereof are the same as described above.
One. R¹⁴Is an aryloxy group
If R¹⁴Is -OR^{twenty five}It is represented by R^{twenty five}Represents an aryl group
And R in the general formulas (2) to (6) ¹~ R^FourA represented by
Synonymous with the reel group, and as a specific example, the same as above
Things.

In the general formula (8), X represents an oxygen atom or a sulfur atom.

In the general formula (9), 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 formulas (2) to (6), and specific examples thereof include the same ones as described above. Can be

In the general formula (9), 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, or- Represents OH. For the halogen atom, alkyl group, aryl group, alkoxy group, and aryloxy group represented by R ¹⁶ and R ¹⁷ ,
It has the same meaning as each substituent represented by R ¹⁴ in the general formula (8), and specific examples thereof include the same as those described above. If R ¹⁶ and R ¹⁷ represents an alkylthio group, R ¹⁶ and R ¹⁷ are each represented by -S-R ^26. R ²⁶ represents an alkyl group, which has the same meaning as the alkyl groups represented by R ^{1 to} R ⁴ in the general formulas (2) to (6), and specific examples thereof include the same ones as described above. If R ¹⁶ and R ¹⁷ represents an arylthio group, R ¹⁶ and R ¹⁷ are each represented by -S-R ^28. R ²⁸ is an aryl group, and has the general formula (2) to
Has the same meaning as the aryl group represented by R ^{1 to} R ⁴ in (6),
Specific examples include the same as described above.

In the general formula (9), Y represents an oxygen atom or a sulfur atom.

Specific examples of the compounds represented by formulas (1) to (6) are shown below. The compounds used in the oil-based ink composition of the present invention are limited to the following specific examples. is not. Specific examples of the Ar moiety of the compounds represented by the general formulas (1) to (6) are shown in Chemical formulas 28 to 48 (1 to 438), and specific examples of the condensed 5-membered heterocyclic moiety (substituent R ^{1 to} R ⁴ and R) are shown in Tables 1 to 27 ((1) to (134)). As specific examples of the compounds represented by the general formulas (1) to (6), specific examples 1 of the Ar moiety
To 438 and a fused 5-membered heterocyclic moiety (1) to (1)
34) are all included. For example, exemplified compound 32- (2) obtained by combining specific example 32 of the Ar moiety and specific example (25) of the fused 5-membered heterocyclic moiety
5) or an exemplary compound 60- in which the specific example 60 of the Ar moiety is combined with the specific example (43) of the fused 5-membered heterocyclic moiety.
(43) and the like. The structures of the compounds are specified by using the same expressions for the exemplified compounds shown in Examples described later.

[0074]

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[0075]

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[0076]

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[0077]

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[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]

[Table 1]

[0096]

[Table 2]

[0097]

[Table 3]

[0098]

[Table 4]

[0099]

[Table 5]

[0100]

[Table 6]

[0101]

[Table 7]

[0102]

[Table 8]

[0103]

[Table 9]

[0104]

[Table 10]

[0105]

[Table 11]

[0106]

[Table 12]

[0107]

[Table 13]

[0108]

[Table 14]

[0109]

[Table 15]

[0110]

[Table 16]

[0111]

[Table 17]

[0112]

[Table 18]

[0113]

[Table 19]

[0114]

[Table 20]

[0115]

[Table 21]

[0116]

[Table 22]

[0117]

[Table 23]

[0118]

[Table 24]

[0119]

[Table 25]

[0120]

[Table 26]

[0121]

[Table 27]

The dye represented by formula (1) may contain a tautomer. For example, the general formula (2)
The dye represented by the formula (1) has at least the following tautomers.

[0123]

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The dye represented by the general formula (2) exists as an isomer mixture with the dyes represented by the general formulas (2-A) and (2-B) shown above. And the dye represented by the general formula (2) alone or the dye represented by the general formula (2-
The dye represented by A) alone or the general formula (2-
The dye represented by B) may be present alone.

In the oil-based ink composition of the present invention, the compound represented by the formula (1) is preferably contained in an amount of 1 to 20% by weight, more preferably 2 to 10% by weight. When the compound represented by the general formula (1) is used alone, hues of yellow, red, magenta, blue and cyan can be obtained, but other dyes may be mixed for hue adjustment. Is also good.

The oil-based ink composition of the present invention is obtained by dissolving or dispersing the compound represented by the general formula (1) in an oil-based medium. The oily medium may be a solid or liquid at normal temperature. Those which are solid at room temperature are preferably those which melt and undergo a phase change to liquid or amorphous by application of heat in the image recording step.

Examples of solid oily media include beeswax, carnauba wax, rice wax, wood wax, jojoba oil, spermaceti, candelilla wax, lanolin, montan wax, ozokerite, ceresin, paraffin wax, and microcrystalline wax. And natural acids such as petrolactam; organic acids such as polyethylene wax, chlorinated hydrocarbons, palmitic acid, stearyl acid, behenic acid, tiglic acid, 2-acetonaphthobehenic acid, 12-hydroxystearic acid and dihydroxystearic acid;
Dodecanol, tetradecanol, hexadecanol,
Eicosanol, docosanol, tetracosanol, hexacosanol, octacosanol, dodecenol, myricyl alcohol, tetracenol, hexadecenol, eicosenol, docosenol, pinene glycol, hinokiol, butynediol, nonanediol,
Alcohols such as isophthalyl alcohol, mesicerin, hexanediol, decanediol, tetradecanediol, hexadecanediol, docosandiol, tetracosandiol, tvneol, phenylglycerin, eicosandiol, octanediol, phenylpropylene glycol;

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, lactose melissa, and the like; saccharide fatty acid esters; Ketones such as heptatriacontanone, hentriacontanone, stearone, lauron; oleamide, lauric amide, stearamide, ricinoleamide, palmitamide, tetrahydrofuranamide, erucamide, myristic amide, 12-hydroxystearic amide, N-stearyl erucamide, N-oleyl stearamide, N, N-ethylenebislauric amide, N N-ethylenebisstearic acid amide, N, N-ethylenebisbehenic acid amide, N, N-xylylenebisstearic acid amide, N, N-butylenebisstearic acid amide, N, N-dioleyladipamide, N N, N-dioleyl sebacamide, N, N
Amides such as distearyl sebacamide, N, N-distearyl terephthalamide, phenacetin, toluamide, acetamide; sulfonamides such as p-toluenesulfonamide, ethylbenzenesulfonamide, butylbenzenesulfonamide; α-methyl Alkyl naphthalenes such as naphthalene, β-methylnaphthalene, and 2,6-dimethylnaphthalene; carboxylic acid esters such as dibutylnaphthalate, dioctylphthalate, dibutyladipate, dimethylterephthalate, benzylbenzoate, and methyl naphthalene-2,6-dicarboxylate Phosphoric acid esters such as tributyl phosphate and triphenyl phosphate;

As the liquid oily medium, one or two kinds may be used.
A mixed solvent of at least one kind of organic solvent is exemplified. Examples of the organic solvent include alcohols such as ethanol, pentanol, heptanol, octanol, cyclohexanol, benzyl alcohol, phenylethyl alcohol, phenylpropyl alcohol, furfuryl alcohol and anis alcohol; ethylene glycol monoethyl 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,
Glycol derivatives such as dipropylene glycol monoethyl ether, triethylene glycol monoethyl ether, ethylene glycol diacetate, ethylene glycol monoethyl ether acetate, and 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, phenoxy ethyl acetate and phenyl acetate Ethyl acetate, benzyl propionate, ethyl benzoate, butyl benzoate, ethyl laurate, butyl laurate, isopropyl myristate, isopropyl palmitate, triethyl phosphate, tributyl phosphate, tricresyl phosphate, diethyl phthalate, dibutyl phthalate ,
Diethyl malonate, 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, dioctyl fumarate, 3-cinnamate Esters such as hexenyl; hydrocarbon solvents such as petroleum ether, petroleum benzyl, tetralin, delican, 1-amylbenzene, dimethylnaphthalene; acetonitrile, formamide, N, N-
And polar solvents such as dimethylformamide, N, N-dimethylacetamide, dimethylsulfoxide, sulfolane, propylene carbonate, N-methyl-2-pyrrolidone, N-vinyl-2-pyrrolidone, and N, N-diethyldodecaneamide. These solvents may be used alone or as a mixture of two or more.

As the oily medium, it is preferable to use a medium having a relatively low melting point (softening point) (for example, 70 ° C. or lower) and a medium having a relatively high melting point (softening point) (120 to 200 ° C.).
When used together, the robustness of the image portion of the formed image is improved, and color transfer or the like is unlikely to occur even when a plurality of recording papers on which the images are formed are superposed. The oil medium preferably contains a polyamide, polyurethane, polyester, epoxy or polyacryl resin compatible with the oil medium used. By using the resin in combination, the film strength of the oil-based ink can be further increased. The resin is preferably contained in an amount of 0.5 to 20% by weight based on the total weight of the oil-based ink composition of the present invention. Further, an additive having an effect of improving the fastness of the dye, an antioxidant, a singlet oxygen quencher, an ultraviolet absorber and the like may be coexisted.

The oil-based ink composition of the present invention can be prepared by dissolving or dispersing the compound represented by the general formula (1) in a liquid or solid oil-based medium. When the oily medium is a solid, it is preferable that the compound represented by the general formula (1) is dissolved in the liquid medium after heating and melting the liquid medium. As the oily medium of the oily ink composition of the present invention, the vehicle described in JP-A-9-176532 can be used, and the method for producing the oily ink composition of the present invention is also described in the above publication. A method is available.

The oil-based ink composition of the present invention can be used as an ink for inkjet recording. In particular,
When the oily medium is solid at normal temperature, it can be used as an ink composition for a so-called hot melt type (or wax jet type) ink jet recording apparatus. Further, the oil-based ink composition of the present invention can be used as an ink sheet for melt-type thermal transfer by coating or impregnating a base material such as a cloth or a plastic film.
Furthermore, it can be used as ink for ballpoint pens and ink for markers.

[0134]

EXAMPLES Hereinafter, the present invention will be described in more detail with reference to examples, but the present invention is not limited to these examples. <Example 1> 1-methylnaphthalene 35 parts by weight 2,6-dimethylnaphthalene 60 parts by weight Dye (exemplified compound 60- (27)) 5 parts by weight The mixture having the above composition was stirred at 60 ° C for 5 hours, and 1-methyl was added. The dye was dissolved in an oil medium of naphthalene and 2,6-dimethylnaphthalene to obtain an oil ink composition. this,
Hot melt inkjet printer “JOLT”
SJ01APS2 "(trade name, product of Hitachi Koki Co., Ltd.) was used to print on electrophotographic paper (product of Xerox Corporation).
When the image portion of the formed image was visually observed, there was no blur in the image portion, and the image had a good magenta hue.
After the image was recorded, the image portion was rubbed with the hand 10 seconds later. As a result, no stain was generated on the background portion around the image and the rubbed hand. Further, irradiation was performed for 100 hours using a xenon fade meter (manufactured by Suga Test Instruments Co., Ltd.), but the discoloration of the image was small. In addition, the oil-based ink composition is
After storage for 3 months at ℃, no separation of the dye and the medium occurred.

<Example 2> Dibutyl naphthalate 50 parts by weight Naphthalene-2,6-dicarboxylic acid diethyl ester 43 parts by weight Dye (exemplified compound 60- (27)) 7 parts by weight Example using a mixture of the above composition In the same manner as in Example 1, an oil-based ink composition was prepared. When the same evaluation was performed on the obtained oil-based ink composition, good results were obtained as in Example 1.

Example 3 30 parts by weight of dibutyl adipate 63 parts by weight of benzyl benzoate 7 parts by weight of a dye (exemplified compound 60- (27)) 7 parts by weight An oil-based ink composition was prepared in the same manner as in Example 1 using the mixture having the above composition. Was prepared. When the same evaluation was performed on the obtained oil-based ink composition, good results were obtained as in Example 1.

<Example 4> Benzyl benzoate 40 parts by weight 2-methylnaphthalene 20 parts by weight Stearamide 35 parts by weight Dye (exemplified compound 60- (27)) 5 parts by weight Example 1 was prepared using the mixture having the above composition. In the same manner as in the above, an oil-based ink composition was prepared. When the same evaluation was performed on the obtained oil-based ink composition, good results were obtained as in Example 1.

Example 5 Tricresyl phosphate 65 parts by weight Dibutyl adipate 31 parts by weight Dye (exemplified compound 60- (27)) 4 parts by weight An oil-based ink composition was prepared in the same manner as in Example 1 using the mixture having the above composition. A product was made. When the same evaluation was performed on the obtained oil-based ink composition, good results were obtained as in Example 1.

<Examples 6 to 25> As shown in Table 28 below, the oil-based ink compositions of Examples 6 to 25 were prepared according to any of the formulations of Examples 1 to 5, except that only the dye was changed. did. Example 1 using the obtained oil-based ink composition
When an image was formed in the same manner as in the above, the hue of the obtained image portion was a good magenta hue.

[0140]

[Table 28]

<Examples 26 to 30> The oil-based ink compositions of Examples 26 to 30 were prepared in the same manner as in Example 1 except that the dyes were changed as shown in Table 29 below. When an image was formed using the obtained oil-based ink composition in the same manner as in Example 1, the obtained image portions had good hues.

[0142]

[Table 29]

Example 31 1-methylnaphthylene 35 parts by weight 2,6-dimethylnaphthalene 55 parts by weight Dye A (exemplified compound 60- (27)) 3 parts by weight Dye B (compound represented by the following structural formula) 3 parts by weight Dye C (compound represented by the following structural formula) 4 parts by weight An oil-based ink composition (hue: black) was prepared in the same manner as in Example 1 using the mixture having the above composition. When the same evaluation was performed on the obtained oil-based ink composition, a good result was obtained in the same manner as in Example 1 (however, the hue of the image portion was black).

[0144]

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<Example 32> Dye A used in Example 31
(Exemplified compound 60- (27)) was replaced with Exemplified compound 303-
An oil-based ink composition (hue: black) was prepared in the same manner as in Example 31 except that (44) was used. When the same evaluation was performed on the obtained oil-based ink composition, a good result was obtained in the same manner as in Example 1 (however, the hue of the image portion was black).

<Example 33> Dye A used in Example 31
(Exemplified compound 60- (27)) was converted to Exemplified compound 90- (6).
An oil-based ink composition (hue: black) was prepared in the same manner as in Example 31 except that 2) was used instead. When the same evaluation was performed on the obtained oil-based ink composition, a good result was obtained in the same manner as in Example 1 (however, the hue of the image portion was black).

Example 34 60 parts by weight of tricresyl phosphate 20 parts by weight of dibutyl adipate 10 parts by weight of a compound represented by the following structural formula 1 5 parts by weight of dye (exemplified compound 6- (27)) A mixture of the above composition was used. Thus, an oil-based ink composition (hue: magenta) was prepared in the same manner as in Example 1. When the same evaluation was performed on the obtained oil-based ink composition,
Good results were obtained as in Example 1.

[0148]

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<Example 35> 60 parts by weight of tricresyl phosphate 15 parts by weight of dibutyl adipate 10 parts by weight of the compound represented by the above structural formula 1 10 parts by weight of the compound represented by the following structural formula 2 Dye (Exemplified compound 6- ( 27)) 5 parts by weight An oil-based ink composition (hue: magenta) was prepared in the same manner as in Example 1 using the mixture having the above composition. When the same evaluation was performed on the obtained oil-based ink composition,
Good results were obtained as in Example 1.

[0150]

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<Example 36> An oil-based ink was prepared in the same manner as in Example 35, except that the compound represented by Structural Formula 3 was used instead of the compound represented by Structural Formula 1. A composition (hue: magenta) was prepared. When the same evaluation was performed on the obtained oil-based ink composition,
Good results were obtained as in Example 1.

[0152]

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[0153]

According to the present invention, it is possible to provide an oil-based ink composition which can form an image having good hue and high storage stability such as light fastness.

 ──────────────────────────────────────────────────続 き Continuing on the front page (72) Inventor Yasuhiro Mitamura 200 Fujinaka Film Co., Ltd., Fuji Photo Film Co., Ltd. (72) Inventor Tatsuo Kawabuchi 200 Onakazato Fujinaka City, Fujinomiya City, Shizuoka Prefecture F Terms (reference) 2C056 EA11 EA13 EE08 FC02 FD02 2H086 BA54 BA56 4J039 AB04 AB05 AB12 BB01 BC03 BC31 BC32 BC33 BC40 BC51 BC52 BC53 BC55 BC65 BC71 BC72 BC73 BC74 BC76 BC77 BC79 BE12 CA04 CA07 EA14 EA35 EA44 GA24

Claims (9)

[Claims] 1. An oil-based ink composition comprising an oil-based medium and 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 X ^{1 to} X ⁵ each independently represent an unsaturated hetero-5 group.
Represents a carbon atom or a nitrogen atom capable of forming a membered ring. ) 2. A compound represented by the general formula (1):
The oil-based ink composition according to claim 1, which is a compound represented by the following general formula (2). Embedded image (In the general formula (2), Ar represents an aryl group or a heterocyclic group, and R ^{1 to} R ³ each independently represent a hydrogen atom, an aryl group, an alkyl group, a heterocyclic group, an acyl group, a carbamoyl group. An alkoxycarbonyl group, an aryloxycarbonyl group, a sulfamoyl group, an alkylsulfonyl group,
Represents an arylsulfonyl group, an acyloxy group, an alkoxy group, an aryloxy group, an alkylthio group, an arylthio group, an amino group, or —OH. ) 3. The compound represented by the general formula (1)
The oil-based ink composition according to claim 1, which is a compound represented by the following general formula (3). Embedded image (Wherein general formula (3), Ar represents an aryl group or a heterocyclic group, R ¹ to R ⁴ are, R ¹ to R ³ in the general formula (2)
Is synonymous with ) 4. A compound represented by the general formula (1):
The oil-based ink composition according to claim 1, which is a compound represented by the following general formula (4). Embedded image (Wherein general formula (4), Ar represents an aryl group or a heterocyclic group, R ¹ to R ³ are, R ¹ to R ³ in the general formula (2)
And R represents a substituent having a Hammett's substituent constant σ _p of 0.3 to 1.5. ) 5. A compound represented by the general formula (1):
The oil-based ink composition according to claim 1, which is a compound represented by the following general formula (5). Embedded image (In the general formula (5), Ar represents an aryl group or a heterocyclic group, and R ¹ and R ³ represent R ¹ to R ¹ in the general formula (2).
It is synonymous with R ³ . ) 6. The compound represented by the general formula (1):
The oil-based ink composition according to claim 1, which is a compound represented by the following general formula (6). Embedded image (In the general formula (6), Ar represents an aryl group or a heterocyclic group, and R ¹ and R ³ represent R ¹ to R ¹ in the general formula (2).
R is synonymous with R ³ and R is Hammet's substituent constant σ _p
Represents a substituent of 0.3 to 1.5. ) 7. The oil-based ink composition according to claim 1, wherein in the general formula (1), Ar is a group represented by the following general formula (7). Embedded image (In the general formula (7), R ⁵ and R ⁶ are each independently:
It represents a hydrogen atom, an alkyl group, or aryl group, R ⁷ ~
R ¹⁰ is 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, an aryloxy group, an alkylthio group. Group, arylthio group, alkylsulfonyl group, arylsulfonyl group, alkylphosphoryl group, arylphosphoryl group, amino group, -C
Represents N or -OH. ) 8. The oil-based ink composition according to claim 1, wherein in the general formula (1), Ar is a group represented by the following general formula (8). Embedded image (In the general formula (8), 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, or an alkoxy group. , An aryloxy group, or —OH, and X represents an oxygen atom or a sulfur atom.) 9. The oil-based ink composition according to claim 1, wherein Ar in the general formula (1) is a group represented by the following general formula (9). Embedded image (In the general formula (9), 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, or —OH, and Y represents an oxygen atom or a sulfur atom.)