JP2002129073A - Composition of oil-based ink - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a composition of oil-based ink having good hue and capable of forming an image having high storage stability such as light-fastness, etc. SOLUTION: The composition of oil-based ink comprises an oil medium and a compound represented by general formula (1). In the formula, Ar is an aryl or heterocyclic group; and R1 to R3 are each hydrogen or halogen atom, -CN, -NH2, -NO2, -OH, -CO2H, alkyl, alkenyl, alkynyl, aryl, acyl, carbamoyl, sulfamoyl, alkoxycarbonyl, aryloxycarbonyl, acyloxy, alkoxy, aryloxy, alkylthio, arylthio, alkylsulfonyl, arylsulfonyl, alkylphosphoryl, arylphosphoryl or substituted amino group.

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 are used as the coloring agent. 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 Problems The object of the present invention is solved by providing the following oil-based ink composition. (1) An oil-based ink composition containing an oil-based medium and a compound represented by the following general formula (I).

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In the formula, Ar represents an aryl group or a heterocyclic group. R ¹ to R ³ are each a hydrogen atom, a halogen _{atom, -CN, -NH 2, -NO 2} , -OH, -CO 2 H,
Alkyl group, alkenyl group, alkynyl group, aryl group, acyl group, carbamoyl group, sulfamoyl group, alkoxycarbonyl group, aryloxycarbonyl group,
Represents 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, or a substituted amino group. (2) The group represented by Ar- in the general formula (I) is
The oil-based ink composition according to the above (1), which is a group represented by the following general formula (II).

[0006]

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In the formula, R ⁴ and R ⁵ represent a hydrogen atom, an alkyl group or an aryl group. R ^{6 to} R ⁹ have the same meanings as R ^{1 to} R ^{3 in the} above (1). (3) The group represented by Ar- in the general formula (I) is
The oil-based ink composition according to the above (1), which is a group represented by the following general formula (III).

[0008]

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In the formula, R ^{10 to} R ¹² represent a hydrogen atom, an alkyl group or an aryl group. R ¹³ represents a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, an aryl group, or an aryloxy group. X represents O or S. (4) The group represented by Ar- in the general formula (I) is
The oil-based ink composition according to the above (1), which is a group represented by the following general formula (IV).

[0010]

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In the formula, R ¹⁴ represents a hydrogen atom, an alkyl group or an aryl group. R ¹⁵ and R ¹⁶ represent a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, an aryloxy group, an alkylthio group, an arylthio group, or an aryl group. Y represents O or S. (5) An oil-based ink composition containing an oil-based medium and a compound represented by the following general formula (V).

[0012]

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In the formula, Ar ′ has the same meaning as Ar in the above (1). R ¹⁷ and R ¹⁸ have the same meanings as R ^{1 to} R ^{3 in} (1) above. R ¹⁹ represents a hydrogen atom, an alkyl group, an aryl group, or an acyl group. Z represents an oxygen atom or a sulfur atom.

[0014]

BEST MODE FOR CARRYING OUT THE INVENTION The oil-based ink composition of the present invention contains the compound represented by the general formula (I) as a dye. The compound represented by the general formula (V) has good hue and good light fastness. Therefore, when an image is formed using the oil-based ink composition of the present invention, the formed image exhibits a good hue and has high light stability in the image area. Further, since the compound has a good affinity for an oily medium, the oily ink composition of the present invention has good storage stability without separation of the oily medium and the dye even when stored for a long time. .

The hydrazone dye of the present invention has the general formula
It is shown by (I). In the general formula (I), Ar represents an aryl group
Or a heterocyclic group. R¹ ~ R^Three Is hydrogen
Atom, halogen atom, -CN, -NH_Two, -NO_Two, -O
H, -CO _TwoH, alkyl group, alkenyl group, alkynyl
Group, aryl group, acyl group, carbamoyl group, sulf
Amoyl group, alkoxycarbonyl group, aryloxy
Carbonyl group, acyloxy group, alkoxy group, aryl
Roxy, alkylthio, arylthio, alk
Rusulfonyl group, arylsulfonyl group, alkylphos
Holyl group, aryl phosphoryl group, or substituted amino group
Represents Halogen atoms include fluorine and chlorine atoms
And fluorine atom and chlorine atom.
Is more preferable.

Ar in the general formula (I) represents an aryl group or a heterocyclic group, which may be further substituted. Examples of the aryl group include a phenyl group and a naphthyl group, which may be further substituted with a halogen atom, a cyano group, a nitro group, an amino group, an alkoxy group, an acylamino group, an amide group, and the like. The following are preferred as the aryl group.

[0017]

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[0018]

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In addition, Ar may be a divalent group. In this case, the hydrazone dye of the present invention has two hydrazone rings. Preferred divalent Ar includes the following.

[0020]

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As the heterocyclic group, 2-pyridyl, 3-
Examples include pyridyl, 4-pyridyl, thienyl, 3-thiophenyl, 2-thiazolyl, 5-thiazolyl, benzothiazolyl, diazolyl, triazolyl, benzodiazolyl, benzoxazolyl, 2-furanyl, and benzothiophenyl. The following are preferred as the heterocyclic group.

[0022]

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The above R¹~ R^ThreeIs a further substituent
May be replaced by R¹~ R ^ThreeOf the substituents of
An aryl group further includes an alkyl group, an alkoxy group,
Oxy group, halogen atom, nitro group, cyano group,
Substituted carbamoyl group, substituted sulfamoyl group, substituted amino
Group, substituted oxycarbomoyl group, substituted oxysulfonyl
Group, alkylthio group, arylthio group, alkylsulfo
Nil group, arylsulfonyl group, aryl group, hydroxy
Group, acyl group, acyloxy group, substituted sulfonyloxy
Si group, substituted aminocarbonyloxy group, substituted phosphoryl
It may be substituted with an oxy group.

[0024] The aryl group may have 6 to 6 carbon atoms.
30 aryl groups are preferred, for example a 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
-A cyclophenyl group, a 3,5-dichlorophenyl group,
3,4-dimethoxyphenyl group, 3,5-dibutoxyphenyl group, 3-octyloxyphenyl group, 3- (dibutylaminocarbonylmethoxy) phenyl group, 3- (di-2-ethylhexylaminocarbonylmethoxy) phenyl group, 3-dodecyloxyphenyl group, 4-chlorophenyl group, 4-cyanophenyl group, 4-nitrophenyl group, 4-trifluoromethylphenyl group, 4-methoxyphenyl group, 4-ethoxyphenyl group, 4-isopropoxyphenyl 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-ethoxy Carbonylphenyl group, 4- (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 group, 4- (4-chlorophenylthio) phenyl group, besides hydroxyphenyl group, phenylsulfonyl Examples include a phenyl group, a phenylsulfonyloxyphenyl group, a phenylcarbonyloxyphenyl group, a dimethylaminocarbonyloxyphenyl group, a butylcarbonyloxyphenyl group, and the like. In addition, groups represented by the following formulas may be mentioned.

[0025]

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Among the substituents of R ^{1 to} R ³ , the alkyl group may be linear or branched, and may have an unsaturated bond. Further, these alkyl groups may be substituted with an alkoxy group, an aryloxy group, an alkoxycarbonyl group, an aryloxycarbonyl group, an aryl group, a hydroxy group, a halogen atom, or the like. The aryl group may be further substituted with an alkyl group, an alkoxy group, a nitro group, a cyano group, a hydroxy group or a halogen atom, —CO ₂ H, or the like.

The alkyl group has 1 to 30 carbon atoms.
Are preferred, for example, methyl group, trifluoromethyl group, ethyl group, butyl group, hexyl group, octyl group, 2-ethylhexyl group, decyl group, dodecyl group, octadecyl group, propyl group, isopropyl group, and isobutyl group , Sec-butyl group, t-butyl group, pentyl group, 1-ethylpentyl group, cyclopentyl group, cyclohexyl group, isopentyl group, 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-t-butylphenyloxymethyl group, ethoxycarbonylethyl group, 2-ethylhexyloxycarbonylethyl group, butyldecyloxycarbonylethyl group, dibutylaminocarbonylmethyl group, dibenzylaminocarbonylethyl group, ethyloxycarbonylpropyl group , 2-ethylhexyloxycarbonylpropyl group, 2,4-di-t-amylphenyloxypropyl group, 1- (2 ', 4'-di-t-amylphenyloxy) propyl group, 2,4-di-t -Butylphenyloxypropyl group, acetyl Aminoethyl group, N, N
-Dihexylaminocarbonylethyl group, 2,4-di-
t-amyloxyethyloxycarbonylpropyl group,
Isostearyloxycarbonylpropyl, 1- (2,
4-di-t-pentylphenyloxy) propyl group,
2,4-di -t- pentylphenyl oxyethyl oxycarbonyl propyl group, naphthyloxy ethyloxycarbonyl ethyl, N- methyl -N- phenylethyl oxycarbonyl ethyl, methanesulfonylamino propyl group, - (CH _{2) m} CO ₂ H and the like.

Among the substituents of R ^{1 to} R ³ , the alkenyl group is preferably an alkenyl group having 2 to 10 carbon atoms, for example, vinyl group, —CH ＝ CH—Ph (cinamyl group) and the like. , An alkynyl group having 2 to 2 carbon atoms
10 alkynyl groups are preferred, for example an ethynyl group,
Examples include a 2-methyl-ethynyl group and a 2-phenyl-ethynyl group.

Among the substituents of R ^{1 to} R ³ , the acyl group is preferably an acyl group having 2 to 20 carbon atoms, for example, acetyl, propanoyl, butanoyl, hexanoyl, octanoyl, octanoyl, 2-amino. Examples include an ethylhexanoyl group, a decanoyl group, a dodecanoyl group, an octadecanoyl group, a 2-cyanopropanoyl group, and a 1,1-dimethylpropanoyl group. Other examples of the acyl group include those shown below.

[0030]

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Among the substituents of R ^{1 to} R ³ , the substituted carbamoyl group includes carbamoyl, N-alkylcarbamoyl, N-arylcarbamoyl, N, N-dialkylcarbamoyl, N, N-diarylcarbamoyl , N-alkyl-N-arylcarbamoyl groups and the like. Examples of the substituted carbamoyl group include C1 to C1
30 substituted carbamoyl groups are preferred, for example, N-methylcarbamoyl group, N-ethylcarbamoyl group, N-
A propylcarbamoyl group, an 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-methylphenyl Carbamoyl 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 group, N
-4-cyanophenylcarbamoyl group, N-methyl-N
-Phenylcarbamoyl group, N, N-dimethylcarbamoyl group, N, N-dibutylcarbamoyl group, N, N-diphenylcarbamoyl group and the like. Examples of the substituted carbamoyl group further include those shown below.

[0032]

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Among the substituents of R ^{1 to} R ³ , the alkoxycarbonyl group is preferably an alkoxycarbonyl group having 2 to 20 carbon atoms, for example, a methoxycarbonyl group, an ethoxycarbonyl group, a propoxycarbonyl group,
Butoxycarbonyl group, hexyloxycarbonyl group,
2-ethylhexyloxycarbonyl group, octyloxycarbonyl group, decyloxycarbonyl group, octadecyloxycarbonyl group, phenyloxyethyloxycarbonyl group, phenyloxypropyloxycarbonyl group, 2,4-di-t-amylphenyloxyethylcarbonyl group , 2,6-di -t- butyl-4-methyl cyclohexyloxy carbonyl group, isostearyl oxycarbonyl _{group, -CO 2 - (CH 2)} m CO 2 H and the like.

Among the substituents of R ^{1 to} R ^3, the aryloxycarbonyl group is preferably an aryloxycarbonyl group having 7 to 30 carbon atoms, for example, 2-methylphenyloxycarbonyl group, 2-chlorophenyloxycarbonyl Group, 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-fluoro Examples include a phenyloxycarbonyl group, a 4-chlorophenyloxycarbonyl group, a 4-cyanophenyloxycarbonyl group, a 4-butoxyphenyloxycarbonyl group, and the like.

Among the substituents of R ^{1 to} R ³ , the acyloxy group is preferably an acyloxy group having 2 to 20 carbon atoms, for example, acetyloxy, propanoyloxy, butanoyloxy, pentanoyloxy. Group, trifluoromethylcarbonyloxy group, octanoyloxy group, decanoyloxy group, undecanoyloxy group, octadecanoyloxy group and the like. The following are further examples of the acyloxy group.

Among the substituents of R ^{1 to} R ³ , the alkoxy group is preferably an alkoxy group having 1 to 30 carbon atoms, for example, methoxy, ethoxy, propyloxy, isopropyloxy, butoxy, Isobutoxy, 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 , - octylaminocarbonyl methyloxy group, N- methyl -N- benzylaminocarbonyl methyl group, a benzyl group, a cyano methyl _{group, -O- (CH 2) m CO} 2 H and the like.

Among the substituents of R ^{1 to} R ^3, the aryloxy group is preferably an aryloxy group having 6 to 30 carbon atoms, for example, phenyloxy group, 1-naphthyloxy group, 2-naphthyloxy group. 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.

Among the substituents of R ^{1 to} R ³ , the alkylthio group is preferably an alkylthio group having 1 to 30 carbon atoms, for example, methylthio, ethylthio, propylthio, isopropylthio, butylthio, isobutyl Thio group, sec-butylthio group, t-butylthio group, pentylthio group, isopentylthio group, hexylthio group, heptylthio group, octylthio group, 2-ethylhexylthio group, decylthio group, dodecylthio group, octadecylthio group, ethoxycarbonylmethylthio group , 2-
Ethylhexyloxycarbonylmethylthio group, aminocarbonylmethylthio group, N, N-dibutylaminocarbonylmethyl group, N-methylaminocarbonylmethylthio group, N-ethylaminocarbonylmethylthio group, N-
Octylaminocarbonylmethylthio group, N-methyl-
N- benzylaminocarbonyl methyl thio group, benzylthio group, cyanomethyl thio _{group, -S- (CH 2) m CO} 2
H and the like.

Among the substituents of R ^{1 to} R ³ , the arylthio group is preferably an arylthio group having 6 to 30 carbon atoms, such as phenylthio, 1-naphthylthio, 2-naphthylthio, and 2-chlorophenylthio. Group,
2-methylphenylthio, 2-methoxyphenylthio, 2-butoxyphenylthio, 3-chlorophenylthio, 3-trifluoromethylphenylthio, 3-
Cyanophenylthio, 3- (2-ethylhexyloxy) phenylthio, 3-nitrophenylthio, 4-
A fluoriphenylthio group, a 4-cyanophenylthio group,
Examples thereof include a 4-butoxyphenylthio group, a 4- (2-ethylhexyloxy) phenylthio group, and a 4-octadecylphenylthio group.

Among the substituents of R ^{1 to} R ³ , the substituted sulfamoyl group includes sulfamoyl, N-alkylsulfamoyl, N-arylsulfamoyl, N, N-
It includes a dialkylsulfamoyl group, an N, N-diarylsulfamoyl group, and an N-alkyl-N-arylsulfamoyl group.

Among the substituents of R ^{1 to} R ³ , the substituted sulfamoyl group is preferably a substituted sulfamoyl group having 0 to 30 carbon atoms, for example, N-methylsulfamoyl group, N-ethylsulfamoyl group , N-propylsulfamoyl group, 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-di (2-ethylhexyl) sulfamoyl group and the like.

Among the substituents of R ^{1 to} R ³ , the alkylsulfonyl group is preferably an alkylsulfonyl group having 1 to 20 carbon atoms, for example, a methylsulfonyl group, an ethylsulfonyl group, a propylsulfonyl group, an isopropylsulfonyl group, Examples thereof include a butylsulfonyl group, 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.

Among the substituents of R ^{1 to} R ³ , the arylsulfonyl group is preferably an arylsulfonyl group having 6 to 30 carbon atoms, for example, a phenylsulfonyl group,
1-naphthylsulfonyl group, 2-naphthylsulfonyl group, 2-chlorophenylsulfonyl group, 2-methylphenylsulfonyl group, 2-methoxyphenylsulfonyl group, 2-butoxyphenylsulfonyl group, 3-chlorophenylsulfonyl group, 3-trifluoromethyl Phenylsulfonyl 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.

Among the substituents represented by R ^{1 to} R ³ , the alkyl phosphoryl group is preferably an alkyl phosphoryl group having 2 to 40 carbon atoms. Examples thereof include a methyl phosphoryl group, an ethyl phosphoryl group, a propyl phosphoryl group and an isopropyl phosphoryl group. Butyl phosphoryl 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-dibutylaminocarbonylmethylphosphoryl group, N-methylaminocarbonylmethylphosphoryl group, N-ethylaminocarbonyl Methylphosphoryl group,
N-octylaminocarbonylmethylphosphoryl group, benzylphosphoryl group and the like.

Among the substituents of R ^{1 to} R ³ , the aryl phosphoryl group is preferably an aryl phosphoryl group having 12 to 50 carbon atoms, for example, a phenyl phosphoryl group, a 1-naphthyl phosphoryl group and a 2-naphthyl phosphoryl group. A 2-chlorophenyl phosphoryl group, a 2-methylphenyl phosphoryl group, a 2-methoxyphenyl phosphoryl group, a 2-butoxyphenyl phosphoryl group, a 3-chlorophenyl phosphoryl group, a 3-trifluoromethylphenyl phosphoryl group, a 3-cyanophenyl phosphoryl group, 3-
(2-ethylhexyloxy) phenyl phosphoryl group,
3-nitrophenyl phosphoryl group, 4-fluorophenyl phosphoryl group, 4-cyanophenyl phosphoryl group,
-Butoxyphenylphosphoryl group, 4- (2-ethylhexyloxy) phenylphosphoryl group, 4-octadecylphenylphosphoryl group and the like.

Among the substituents of R ^{1 to} R ³ , the substituted amino group includes amino, N-alkylamino, N-arylamino, N-acylamino, N-sulfonylamino, N, N- Dialkylamino group, N, N-diarylamino group, N-alkyl-N-arylamino group,
And N-disulfonylamino group. As the substituted amino group, a substituted amino group having 0 to 50 carbon atoms is preferable. For example, an N-methylamino group, an N-ethylamino group, an N-propylamino group, an N-isopropylamino group, an 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-chlorophenylamino 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. Further, examples of the substituted amino group include the following.

[0047]

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[0048]

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Further, a dye structure having a structure in which any ^one of R ^{1 to} R ³ of the two compounds represented by the above general formula (I) is linked via a divalent linking group. It is also possible to use two hydrazone dyes.

In the general formula (II), R ⁴ and R ⁵ each represent a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. R ⁴ and R ⁵ may be the same or different. As the substituent,
Alkoxy group, alkoxycarbonyl group, alkylsulfonyl group, substituted amino group, substituted amide group, aryl group,
Examples include, but are not limited to, an aryloxy group.

The alkyl group may have 1 to 18 carbon atoms.
Are preferred, for example, a methyl group, a trifluoromethyl group, an ethyl group, a propyl group, an isopropyl group,
Butyl group, sec-butyl group, t-butyl group, pentyl group, isopentyl group, cyclopentyl group, hexyl group,
Cyclohexyl group, octyl group, t-octyl group, 2-
Ethylhexyl, nonyl, octadecyl, benzyl, 4-methoxybenzyl, tolphenylmethyl, ethoxycarbonylmethyl, butoxycarbonylmethyl, 2-ethylhexyloxycarbonylmethyl, 2 ', 4'-diisopentyl Phenyloxymethyl group, 2 ′, 4′-di-t-butylphenyloxymethyl group, dibenzylaminocarbonylmethyl group, 2,4-di-t-amylphenyloxypropyl group, ethoxycarbonylpropyl group, 1- ( 2 ′, 4′-di-t-amylphenyloxy) propyl group, acetylaminoethyl group, 2- (N, N-dimethylamino) ethyl group, 2-
(N, N-diethylamino) propyl group, methanesulfonylaminopropyl group, acetylaminoethyl group, 2-
(N, N-dimethylamino) ethyl group, 2- (N, N-
A diethylamino) propyl group is preferred.

The aryl group has 6 carbon atoms.
~ 30 aryl groups are preferable, for example, a phenyl group,
2-methylphenyl group, 2-chlorophenyl group, 2-methoxyphenyl group, 2-butoxyphenyl group, 2- (2
-Ethylhexyloxy) phenyl group, 2-octyloxyphenyl group, 3- (2,4-di-t-pentylphenoxyethoxy) phenyl group, 4-chlorophenyl group,
2,5-dichlorophenyl group, 2,4,6-trimethylphenyl group, 3-chlorophenyl group, 3-methylphenyl group, 3-methoxyphenyl group, 3-butoxyphenyl group, 3-cyanophenyl group, 3- (2 -Ethylhexyloxy) phenyl group, 3,4-dichlorophenyl group,
3,5-dichlorophenyl group, 3,4-dimethoxyphenyl group, 3- (dibutylaminocarbonylmethoxy) phenyl group, 4-cyanophenyl group, 4-methylphenyl group, 4-methoxyphenyl group, 4-butoxyphenyl group, 4- (2-ethylhexyloxy) phenyl group, 4
-Benzylphenyl group, 4-aminosulfonylphenyl group, 4-N, N-dibutylaminosulfonylphenyl group, 4-ethoxycarbonylphenyl group, 4- (2-ethylhexylcarbonyl) phenyl group, 4-fluorophenyl group, 3- Acetylphenyl group, 2-acetylaminophenyl group, 4- (4-chlorophenylthio) phenyl group, 4- (4-methylphenyl) thio-2,5-butoxyphenyl group, 4- (N-benzyl-N-methyl Amino) -2-dodecyloxycarbonylphenyl group, and the like, but are not particularly limited thereto. Further, these groups further include an alkyloxy group, an alkylthio group, a substituted phenyl group, a cyano group, a substituted amino group,
It may be substituted by a halogen atom, a heterocyclic group or the like.

In the general formula (III), R^Ten, R¹¹, R
¹²Is a hydrogen atom, a substituted or unsubstituted alkyl
Represents a group or a substituted or unsubstituted aryl group.
R^Ten, R ¹¹, R¹²Can be the same or different
Is also good. As the substituent, an alkyl group, an alkoxy group,
Alkylthio, aryl, aryloxy, ant
Thiol group, acyl group, alkoxycarbonyl group,
Bamoyl group, carboamide group, sulfonyl group, sulfa
Moyl group, sulfonamide group, ureide group, halogen source
And an amino group, a heterocyclic group and the like.

The alkyl group has 1 to 18 carbon atoms.
Are preferred, for example, a methyl group, a trifluoromethyl group, an ethyl group, a propyl group, an isopropyl group,
Butyl group, sec-butyl group, t-butyl group, ventil group, isopentyl group, cyclopentyl group, hexyl group,
Cyclohexyl group, octyl group, t-octyl group, 2-
Ethylhexyl, nonyl, octadecyl, benzyl, 4-methoxybenzyl, triphenylmethyl, ethoxycarbonylmethyl, butoxycarbonylmethyl, 2-ethylhexyloxycarbonylmethyl, 2 ', 4'-diisopentyl Phenyloxymethyl group, 2 ′, 4′-di-t-butylphenyloxymethyl group, dibenzylaminocarbonylmethyl group, 2,4-di-t-amylphenyloxypropyl group, ethoxycarbonylpropyl group, 1- ( 2 ′, 4′-di-t-amylphenyloxy) propyl group, acetylaminoethyl group, 2- (N, N-dimethylamino) ethyl group, 2-
(N, N-diethylamino) propyl group, methanesulfonylaminopropyl group, acetylaminoethyl group, 2-
(N, N-dimethylamino) ethyl group, 2- (N, N-
Diethylamino) propyl group, 1-methyl-2- (4-
(Methoxyphenoxy) ethyl group, di-n-butylaminocarbonylmethyl group, di-n-octylaminocarbonylmethyl group and the like are preferable.

The aryl group has 6 carbon atoms.
~ 30 aryl groups are preferable, for example, a phenyl group,
2-methylphenyl group, 2-chlorophenyl group, 2-methoxyphenyl group, 2-butoxyphenyl group, 2- (2
-Ethylhexyloxy) phenyl group, 2-octyloxyphenyl group, 3- (2,4-di-t-pentylphenoxyethoxy) phenyl group, 4-chlorophenyl group,
2,5-dichlorophenyl group, 2,4,6-trimethylphenyl group, 3-chlorophenyl group, 3-methylphenyl group, 3-methoxyphenyl group, 3-butoxyphenyl group, 3-cyanophenyl group, 3- (2 -Ethylhexyloxy) phenyl group, 3,4-dichlorophenyl group,
3,5-dichlorophenyl group, 3,4-dimethoxyphenyl group, 3- (dibutylaminocarbonylmethoxy) phenyl group, 4-cyanophenyl group, 4-methylphenyl group, 4-methoxyphenyl group, 4-butoxyphenyl group, 4- (2-ethylhexyloxy) phenyl group, 4
-Benzylphenyl group, 4-aminosulfonylphenyl group, 4-N, N-dibutylaminosulfonylphenyl group, 4-ethoxycarbonylphenyl group, 4- (2-ethylhexylcarbonyl) phenyl group, 4-fluorophenyl group, 3- Acetylphenyl group, 2-acetylaminophenyl group, 4- (4-chlorophenylthio) phenyl group, 4- (4-methylphenyl) thio-2,5-butoxyphenyl group, 4- (N-benzyl-N-methyl Amino) -2-dodecyloxycarbonylphenyl group, and the like, but are not particularly limited thereto.
Further, these groups may be further substituted by an alkyloxy group, an alkylthio group, a substituted phenyl group, a cyano group, a substituted amino group, a halogen atom, a heterocyclic group and the like.

In the general formula (III), R¹³Alkyl in
Group and aryl group are the same^TenOr R¹²A
The same as the alkyl group and the aryl group. Also the general formula
In (III), R¹³Is an alkoxy group, R¹³Is
-OR²⁰And R²⁰Is R ^TenOr R¹²A
Same as the alkyl group. It also has the general formula (III)
And R¹³Is an aryloxy group, R¹³Is -OR^{twenty one}so
Yes, R^{twenty one}Is R^TenOr R¹²And the aryl group in
Is the same. Also, R¹³Represents a halogen atom,
Chloro and fluoro groups are preferred.

In the general formula (IV), the alkyl group and the aryl group for R ¹⁴ are the same as the alkyl group and the aryl group for R ¹⁰ to R ¹² . Further, in the general formula (IV), the halogen, alkyl group, aryl group, alkoxy group and aryloxy group in R ¹⁵ and R ¹⁶ are the same as R ¹³ described above. In the general formula (IV), R
The alkylthio groups at ¹⁵ and R ¹⁶ are each -S-
R ²² and —SR ²³ , wherein R ²² and R ²³ are
¹⁰ to be the same as the alkyl group in R ^12. Further, in the general formula (IV), the arylthio groups for R ¹⁵ and R ¹⁶ are —S—R ²⁴ and —S—R ²⁵ , respectively.
R ²⁴ and R ²⁵ are the same as the above-mentioned aryl groups for R ¹⁰ to R ¹² . Further, the alkyl group, aryl group and acyl group in R ¹⁹ of the general formula (V) are the same as those described above for R ¹ to R ³
And the same as the alkyl group, aryl group, and acyl group.

The oil solubility and pigment structure of the hydrazone dye of the present invention can be controlled by appropriately introducing a substituent.

Tables 1 to 21 show specific examples of the Ar portion of the hydrazone dye represented by formula (I) of the present invention, and Tables 22 to 28 show specific examples of the coupler portion. Specific examples of the Ar, Ar and coupler moieties are not limited to these. The Ar portion is indicated by Arabic numerals, and the coupler portion is indicated by Arabic numerals with parentheses. [Ar part]

[0060]

[Table 1]

[0061]

[Table 2]

[0062]

[Table 3]

[0063]

[Table 4]

[0064]

[Table 5]

[0065]

[Table 6]

[0066]

[Table 7]

[0067]

[Table 8]

[0068]

[Table 9]

[0069]

[Table 10]

[0070]

[Table 11]

[0071]

[Table 12]

[0072]

[Table 13]

[0073]

[Table 14]

[0074]

[Table 15]

[0075]

[Table 16]

[0076]

[Table 17]

[0077]

[Table 18]

[0078]

[Table 19]

[0079]

[Table 20]

[0080]

[Table 21]

Specific examples of the coupler portion of the compound (dye) in the present invention are described below.

[0082]

[Table 22]

[0083]

[Table 23]

[0084]

[Table 24]

[0085]

[Table 25]

[0086]

[Table 26]

In the oil-based ink composition of the present invention, the compound represented by the general formula (I) is used in an amount of 0.2 to 10% by weight.
It is preferably contained, and more preferably 2 to 10% by weight.

When the compound represented by the formula (1) is used alone, yellow, red, magenta and blue hues can be obtained, but other dyes may be mixed to adjust the hue. You may.

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. , Petrolactam, etc .; organic acids such as polyethylene wax, chlorinated hydrocarbons, palmitic acid, stearyl acid, behenic acid, tiglic acid, 2-acetonaphthobehenic acid, 12-hydroxystearic acid, dihydroxystearic acid; dodecanol , Tetradecanol, hexadecanol, eicosanol, docosanol, tetracosanol, hexacosanol, octacosanol, dodecenol, myricyl alcohol, tetracenol, hexadecenol, eicoseno , Docosenol, pinene glycol, hinokiol, butynediol, nonanediol, isophthalyl alcohol, mesicerin, hexanediol, decanediol, tetradecanediol, hexadecanediol, docosandiol, tetracosandiol, televisionneol, phenylglycerin, eicosandi Alcohols such as all, octanediol and 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, 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;
α-methylnaphthalene, β-methylnaphthalene, 2,6
Alkyl naphthalenes such as dimethyl naphthalene; carboxylic esters such as dibutyl naphthalate, dioctyl phthalate, dibutyl adipate, dimethyl terephthalate, benzyl benzoate, naphthalene-2,6-dicarboxylic acid methyl ester; tributyl phosphate;
Phosphate esters such as triphenyl phosphate;

Examples of the liquid oily medium include a mixed solvent of one or more organic solvents. 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, dipropylene glycol monoethyl ether, triethylene glycol monoethyl ether, ethylene glycol diacetate, ethylene glycol Monoethyl ether ace Over DOO, 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, hexyl ether; ethyl acetate, amyl acetate, benzyl 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, tricresyl phosphate, diethyl phthalate, phthalic acid Dibutyl, 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,
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-
Polar solvents such as 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 (I) 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 (I) is dissolved in the liquid medium after heating and melting the liquid medium. The oil-based medium of the oil-based ink composition of the present invention is described in JP-A-9-176532.
The vehicle described in the official gazette can be used.
The method described in the above publication can be used for the method for producing the oil-based ink composition of the present invention.

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.
Further, it can be used as a ballpoint pen ink and a marker ink.

[0097]

EXAMPLES The present invention will be described in more detail with reference to the following Examples, which should not be construed as limiting the present invention. Below, the dye compound in the present invention,
This is shown as a combination of an Ar portion and a coupler portion shown below. For example, the exemplified compound 2- (1) is a compound obtained by combining a compound having an Ar moiety (diazo moiety) shown in 2 of Table 1 and a compound having a coupler moiety shown in (1) of Table 22. means. That is, the compound represented by 2- (1) has the following structure.

[0098]

Embedded image

[0099]

Embedded image

<Example 1> 1-methylnaphthalene 35 parts by weight 2,6-dimethylnaphthalene 60 parts by weight Dye (exemplary compound 262- (34)) 5 parts by weight The mixture having the above composition was stirred at 60 ° C for 5 hours. The dye was dissolved in an oily medium of 1-methylnaphthalene and 2,6-dimethylnaphthalene to obtain an oily ink composition. this,
Hot melt inkjet printer “JOLT”
SJ01A PS2 "(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. Furthermore, irradiation was performed for 100 hours using a xenon fade meter (product of Suga Test Instruments Co., Ltd.)
The discoloration of the image was small. In addition, the above ink composition
After storage at 0 ° C. for 3 months, 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 262- (34)) 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> Dibutyl adipate 30 parts by weight Benzyl benzoate 63 parts by weight Dye (exemplified compound 262- (34)) 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 262- (34)) 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 65 parts by weight of tricresyl phosphate 31 parts by weight of dibutyl adipate 4 parts by weight of a dye (exemplified compound 262- (34)) 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 20> As shown in Table 27 below, the oil-based ink compositions of Examples 6 to 20 were prepared according to any of the formulations of Examples 1 to 5, except that only the dye was changed. did. When an image was formed using the obtained oil-based ink composition in the same manner as in Example 1, the hue of the obtained image portion was a good cyan hue.

[0106]

[Table 27]

<Examples 21 to 30> Oil-based ink compositions of Examples 21 to 30 were prepared in the same manner as in Example 1 except that the dyes were changed as shown in Table 28 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.

[0108]

[Table 28]

<Example 31> 1-methylnaphthylene 35 parts by weight 2,6-dimethylnaphthalene 55 parts by weight Dye A (exemplified compound 262- (34)) 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).

[0110]

Embedded image

<Example 32> Dye A used in Example 31
(Exemplified compound 262- (34)) was converted to Exemplified compound 264.
An oil-based ink composition (hue: black) was prepared in the same manner as in Example 31, except that-(20) was used. The same evaluation was performed on the obtained oil-based ink composition.
(Except that the hue of the image portion is black) and good results were obtained.

<Example 33> Dye B used in Example 31
Was changed to Example Compound 32- (15).
In the same manner as in Example 1, an oil-based ink composition (hue: black) was prepared.
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 a dye (exemplified compound 32- (15)) A mixture of the above composition was used. In the same manner as in Example 1, an oil-based ink composition (hue: cyan) was produced. When the same evaluation was performed on the obtained oil-based ink composition, good results were obtained as in Example 1.

[0114]

Embedded image

<Example 35> Tricresyl phosphate 60 parts by weight Dibutyl adipate 15 parts by weight 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 32- ( 15)) 5 parts by weight An oil-based ink composition (hue: cyan) 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.

[0116]

Embedded image

<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: cyan) was prepared. When the same evaluation was performed on the obtained oil-based ink composition, good results were obtained as in Example 1.

[0118]

Embedded image

[0119]

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.

 ────────────────────────────────────────────────── ─── Continuing on the front page (72) Inventor Tetsunori Matsushita 200 Onakazato, Fujinomiya City, Shizuoka Prefecture Fuji Photo Film F Co., Ltd. F-term (Reference) 2H086 BA54 BA55 2H111 BA38 BA47 BA48 BA50 4J039 AD01 BB01 BB02 BB03 BC05 BC07 BC10 BC11 BC12 BC13 BC16 BC19 BC29 BC32 BC33 BC34 BC36 BC38 BC44 BC50 BC51 BC52 BC53 BC54 BC55 BC65 BC71 BC72 BC73 BC74 BC75 BC76 BC77 BC78 BC79 BE07 BE12 CA04 CA09 EA35 EA44 EA48 FA02 FA03 GA06 GA21 GA24 GA26 GA27

Claims (5)

[Claims] 1. An oil-based ink composition containing an oil-based medium and a compound represented by the following general formula (I). Embedded image In the formula, Ar represents an aryl group or a heterocyclic group. R ¹
To R ³ are a hydrogen atom, a halogen atom, -CN,
_{-NH 2, -NO 2, -OH,} -CO 2 H, an alkyl group,
Alkenyl group, alkynyl group, aryl group, acyl group,
Carbamoyl, sulfamoyl, alkoxycarbonyl, aryloxycarbonyl, acyloxy, alkoxy, aryloxy, alkylthio, arylthio, alkylsulfonyl, arylsulfonyl, alkylphosphoryl, arylphosphoryl, or substituted amino Represents a group. 2. The oil-based ink composition according to claim 1, wherein the group represented by Ar- in the general formula (I) is a group represented by the following general formula (II). Embedded image In the formula, R ⁴ and R ⁵ represent a hydrogen atom, an alkyl group, or an aryl group. R ^{6 to} R ⁹ have the same meanings as R ^{1 to} R ^{3 in} claim 1. 3. The oil-based ink composition according to claim 1, wherein the group represented by Ar— in the general formula (I) is a group represented by the following general formula (III). Embedded image In the formula, R ^{10 to} R ¹² represent a hydrogen atom, an alkyl group, or an aryl group. R ¹³ represents a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, an aryl group, or an aryloxy group. X represents O or S. 4. The oil-based ink composition according to claim 1, wherein the group represented by Ar— in the general formula (I) is a group represented by the following general formula (IV). Embedded image In the formula, R ¹⁴ represents a hydrogen atom, an alkyl group or an aryl group. R ¹⁵ and R ¹⁶ represent a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, an aryloxy group, an alkylthio group, an arylthio group, or an aryl group. Y represents O or S. 5. An oil-based ink composition containing an oil-based medium and a compound represented by the following general formula (V). Embedded image In the formula, Ar ′ has the same meaning as Ar in the above (1). R ¹⁷ and R ¹⁸ have the same meanings as R ^{1 to} R ^{3 in} (1) above. R ¹⁹ represents a hydrogen atom, an alkyl group, an aryl group, or an acyl group. Z represents an oxygen atom or a sulfur atom.