JP2003049103A - Oily ink composition - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide an oily ink composition capable of forming an image having a good hue and high preservation stability such as light fastness. SOLUTION: This oily ink composition comprises an oily medium and a compound represented by general formula (I) (Ar denotes an aryl group or the like; R<1> denotes hydrogen atom, a halogen atom, nitrile, hydroxy group, nitro group, carboxy group, an alkyl group, an aryl group, an alkoxy group, an aryloxy group, an alkylthio group, an arylthio group, an alkylcarbonyl group, an arylcarbonyl group, can alkylsulfonyl group, an arylsulfonyl group or the like; R<2> to R<4> denote each hydrogen atom, an alkyl group, an aryl group, an alkylcarbonyl group, an arylcarbonyl group, an alkylsulfonyl group, an arylsulfonyl group or the like; X denotes N-R<5> , oxygen atom or sulfur atom; R<5> denotes hydrogen atom, an alkyl group, an aryl group or the like; Y denotes C-R<6> or nitrogen atom; and R<6> is the same as that defined by R<1> ).

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention relates to an oil-based ink composition, and more particularly to an oil-based ink composition using an azo dye having a specific structure.

[0002]

BACKGROUND OF THE INVENTION Oil-based ink compositions are generally compositions in which a colorant is dispersed or dissolved in an oil-based medium. Conventionally,
Various pigments are used as the colorant. However, when a conventional dye is used, there are problems that the hue of the oil-based ink composition is slightly unclear, the light fastness is poor, and the like. In addition, since the dispersibility or dissolution stability of the dye in the oil medium is insufficient, there are drawbacks such that the dye discolors or discolors or separates from the oil medium when the oil-based ink composition is stored for a long period of time. .

[0003]

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

[0004]

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).

[0005]

[Chemical 6]

In the general formula (I), Ar represents an aryl group or a heterocyclic group. R ¹ is a hydrogen atom, a halogen atom, a nitrile, a hydroxy group, a nitro group, a carboxyl group, an alkyl group, an aryl group, an alkoxy group, an aryloxy group, an alkylthio group, an arylthio group, an alkylcarbonyl group, an arylcarbonyl group, an alkylsulfonyl. Represents a group, an arylsulfonyl group, a carbamoyl group, a sulfamoyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, an alkylphosphoryl group, an arylphosphoryl, and an amino group.

In the general formula (1), R ^{2 to} R ⁴ are hydrogen atoms,
Represents an alkyl group, aryl group, alkylcarbonyl group, arylcarbonyl group, alkylsulfonyl group, arylsulfonyl group, alkoxycarbonyl group, aryloxycarbonyl group, dialkylphosphoryl group, diarylphosphoryl group, dialkoxyphosphoryl group, diaryloxyphosphoryl group. . R ² and R ³ may combine with each other to form a ring.

In the general formula (1), X represents NR ⁵ , an oxygen atom and a sulfur atom. R ⁵ is a hydrogen atom, an alkyl group,
It represents an aryl group, an alkylsulfonyl group, an arylsulfonyl group, an alkylcarbonyl group, or an arylcarbonyl group. In the general formula (1), Y represents C-R ^6, a nitrogen atom. R ⁶ has the same meaning as R ¹ .

<2> The oil-based ink composition according to <1>, wherein the group represented by Ar-in the general formula (I) is a group represented by the following general formula (II).

[0010]

[Chemical 7]

In the general formula (II), R ⁷ and R ⁸ are hydrogen atoms,
It represents an alkyl group or an aryl group. R ^{9 to} R ¹² are
It is synonymous with R ^{1 of} claim 1.

<3> The oil-based ink composition according to <1>, wherein the group represented by Ar-in the general formula (I) is a group represented by the following general formula (III).

[0013]

[Chemical 8]

In the general formula (III), R ^{13 to} R ¹⁵ represent a hydrogen atom, an alkyl group or an aryl group. General formula (II
In I), R ¹⁶ is a hydrogen atom, a halogen atom, an alkyl group,
It represents an aryl group, an alkoxy group, or an aryloxy group.

<4> The oil-based ink composition according to <1>, wherein the group represented by Ar-in the general formula (I) is a group represented by the following general formula (IV).

[0016]

[Chemical 9]

In the general formula (IV), R ¹⁷ represents a hydrogen atom, an alkyl group or an aryl group. In the general formula (IV), R ¹⁸ ,
R ¹⁹ represents a hydrogen atom, a halogen atom, an alkyl group, an aryl group, an alkoxy group, an aryloxy group, an alkylthio group or an arylthio group. In general formula (IV), Z represents an oxygen atom or a sulfur atom.

<5> The compound represented by the general formula (I) is represented by the following general formula (I-1), the following general formula (I-2), the following general formula (I-3), or the following general formula (I-3). The oil-based ink composition according to <1>, which is a compound represented by I-4).

[0019]

[Chemical 10]

[0020]

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. In order to improve the hue such as sharpening the absorption of the dye, it is preferable that the structure is biased to one of the azo structure and the hydrazone structure, or that the structure does not cause tautomerization. The present inventors have found that they are fixed to an azo dye by a guanidino group, and completed the present invention. The azo dye of the present invention gives magenta coloring excellent in hue such as sharp absorption of the dye.

The azo dye used in the oil-based ink composition of the present invention is represented by the above general formula (I). General formula (I)
Ar therein 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. As the aryl group, those shown below are preferable.

[0022]

[Chemical 11]

[0023]

[Chemical 12]

Further, Ar may be a divalent group. The following are mentioned as preferable divalent Ar.

[0025]

[Chemical 13]

As the heterocyclic group, 2-pyridyl, 3-
Pyridyl, 4-pyridyl, thienyl, 3-thiophenyl, 2-thiazolyl, 5-thiazolyl, benzothiazolyl, diazolyl, triazolyl, benzodiazolyl, benzoxazolyl, 2-furanyl, benzothiophenyl and the like can be mentioned. As the heterocyclic group, those shown below are preferable.

[0027]

[Chemical 14]

In the general formula (II), R ⁷ and R ⁸ are respectively
It represents a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. Examples of the substituent include, but are not limited to, an alkoxy group, an alkoxycarbonyl group, an alkylsulfonyl group, a substituted amino group, a substituted amide group, an aryl group and an aryloxy group.

The alkyl group represented by R ⁷ and R ⁸ is
An alkyl group having 1 to 18 carbon atoms is preferable, for example, methyl group, trifluoromethyl group, ethyl group, propyl group, 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 group, nonyl group, octadecyl group, benzyl group, 4-methoxybenzyl group,
Triphenylmethyl group, ethoxycarbonylmethyl group,
Butoxycarbonylmethyl group, 2-ethylhexyloxycarbonylmethyl group, 2 ', 4'-diisopentylphenyloxymethyl 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 and the like are preferable.

The aryl group represented by R ⁷ and R ⁸ is preferably an aryl group having 6 to 30 carbon atoms, for example, phenyl group, 2-methylphenyl group, 2-chlorophenyl group, 2-methoxy group. Phenyl 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, Examples thereof include a 5-butoxyphenyl group and a 4- (N-benzyl-N-methylamino) -2-dodecyloxycarbonylphenyl group, but are not particularly limited thereto. In addition, these groups are further
Alkyloxy group, alkylthio group, substituted phenyl group,
It may be substituted with a cyano group, a substituted amino group, a halogen atom, a heterocyclic group or the like. Note that R ^{9 to} R ¹² have the same meaning as R ¹ described later.

In the general formula (III), R ^{13 to} R ¹⁵ are
Each represents a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. As the substituent, an alkyl group, an alkoxy group, an alkylthio group, an aryl group, an aryloxy group, an arylthio group, an acyl group, an alkoxycarbonyl group, a carbamoyl group, a carboxamide group, a sulfonyl group, a sulfamoyl group, a sulfonamide group, a ureido group, Examples thereof include a halogen atom, an amino group and a heterocyclic group.

The alkyl group represented by R ^{13 to} R ¹⁵ is preferably an alkyl group having 1 to 18 carbon atoms, for example, methyl group, trifluoromethyl group, ethyl group, propyl group, 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 group, nonyl group, octadecyl group, benzyl group, 4-methoxybenzyl group, triphenyl Methyl group, ethoxycarbonylmethyl group, butoxycarbonylmethyl group, 2-ethylhexyloxycarbonylmethyl group, 2 ', 4'-diisopentylphenyloxymethyl 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-
An n-octylaminocarbonylmethyl group and the like are preferable.

The aryl group represented by R ^{13 to} R ¹⁵ is preferably an aryl group having 6 to 30 carbon atoms,
For example, 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- Examples thereof include a 2,5-butoxyphenyl group and a 4- (N-benzyl-N-methylamino) -2-dodecyloxycarbonylphenyl group, but are not particularly limited thereto. In addition, these groups are further
Alkyloxy group, alkylthio group, substituted phenyl group,
It may be substituted with a cyano group, a substituted amino group, a halogen atom, a heterocyclic group or the like.

In the general formula (III), R ¹⁶ is a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy. Represents a group. The alkyl group and aryl group for R ¹⁶ are the same as R ¹³
To R ^{15 have} the same meanings as the alkyl group and the aryl group. Further, in the general formula (III), when R ¹⁶ is an alkoxy group, R ¹⁶ is —OR ²⁰ , and R ²⁰ is the same as the alkyl group in R ^{13 to} R ¹⁵ . Further, in formula (III), when R ¹⁶ is an aryl group, R ^{1 6} is -OR
^And R ²¹ has the same meaning as the aryl group in R ^{13 to} R ¹⁵ . Further, when R ¹⁶ represents a halogen atom, a chloro group and a fluoro group are preferable.

R ¹⁷ in the general formula (IV) represents a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. The alkyl group and aryl group for R ^{17 have the same} meaning as the alkyl group and aryl group for R ^{13 to} R ¹⁵ . R ¹⁸ and R ¹⁹ in the general formula (IV) are a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group,
It represents a substituted or unsubstituted aryl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkylthio group, or a substituted or unsubstituted arylthio group. The halogen atom, alkyl group, aryl group, alkoxy group and aryloxy group in R ¹⁸ and R ¹⁹ have the same meaning as R ¹⁶ . Also, R ¹⁸ ,
The alkylthio group in R ¹⁹ is —S—R ²² and —S—R ²³ , respectively, and R ²² and R ²³ have the same meaning as the alkyl group in R ^{13 to} R ¹⁵ . Furthermore, the arylthio groups in R ¹⁸ and R ¹⁹ are —S—R ²⁴ and —S—R ^{25, respectively.}
And R ²⁴ and R ²⁵ have the same meaning as the aryl group in R ^{13 to} R ¹⁵ . Z in the general formula (IV) represents an oxygen atom or a sulfur atom.

R ¹ in the general formula (I) is a hydrogen atom,
Halogen atom, nitrile, hydroxy group, nitro group, carboxyl group, alkyl group, aryl group, alkoxy group, aryloxy group, alkylthio group, arylthio group, alkylsulfonyl group, arylsulfonyl group, alkylcarbonyl group, arylcarbonyl group, carbamoyl Group, sulfamoyl group, alkoxycarbonyl group,
It represents an aryloxycarbonyl group, an amino group, an alkylphosphoryl group, or an arylphosphoryl, which may have a substituent.

R in the general formula (I)²~ R^FourIs the hydrogen source
Child, alkyl group, aryl group, alkylsulfonyl group,
Arylsulfonyl group, alkylcarbonyl group, aryl
Lecarbonyl group, alkoxycarbonyl group, aryl group
Xycarbonyl group, dialkylphosphoryl group, diary
Ruphosphoryl group, dialkoxyphosphoryl group, diaryle
Represents a luoxyphosphoryl group, which has a substituent
You may stay. Also, R ²And R³Combine to form a ring
You may stay.

Particularly, at least one of R ^{2 to} R ⁴ is an alkylsulfonyl group, arylsulfonyl group, alkylcarbonyl group, arylcarbonyl group, dialkoxyphosphoryl group, diaryloxyphosphoryl group, dialkylphosphoryl group, diarylphosphoryl group. Is preferred.

X in the general formula (I) represents NR ⁵ , an oxygen atom and a sulfur atom. R ⁵ represents a hydrogen atom, an alkyl group, an aryl group, an alkylsulfonyl group, an arylsulfonyl group, an alkylcarbonyl group or an arylcarbonyl group, which may have a substituent. Y in the general formula (I) represents C—R ^{6 or} a nitrogen atom. R
⁶ has the same meaning as R ¹ above.

The alkyl group represented by R ^{1 to} R ⁶ 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.
Is 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, 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.

The aryl group represented by R ^{1 to} R ⁶ is an alkyl group, an alkoxy group, an aryloxy group, a halogen atom, a nitro group, a cyano group, a substituted carbamoyl group, a substituted sulfamoyl group, a substituted amino group or a substituted oxycarbo group. Moyl 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, substituted phosphoryloxy group It may be substituted.

The aryl group has 6 to 6 carbon atoms.
An aryl group of 30 is preferable, 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
-Cyclorophenyl group, 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, hydroxyphenyl group, phenylsulfonyl group Examples thereof include a phenyl group, a phenylsulfonyloxyphenyl group, a phenylcarbonyloxyphenyl group, a dimethylaminocarbonyloxyphenyl group, and a butylcarbonyloxyphenyl group. In addition to these, groups represented by the following formulas are also included.

[0044]

[Chemical 15]

The alkoxy group represented by R ¹ and R ⁶ is preferably an alkoxy group having 1 to 30 carbon atoms, and examples thereof include a methoxy group, an ethoxy group, a propyloxy group, an isopropyloxy group, a butoxy group and an isobutoxy group. , S
ec-butoxy group, t-butoxy group, pentyloxy group, isopentyloxy group, hexyloxy group, heptyloxy group, octyloxy group, 2-ethylhexyloxy group, decyloxy group, dodecyloxy group, octadecyloxy group, ethoxycarbonyl Methyloxy group, 2
-Ethylhexyloxycarbonylmethyloxy group, aminocarbonylmethyloxy group, N, N-dibutylaminocarbonylmethyloxy group, N-methylaminocarbonylmethyloxy group, N-ethylaminocarbonylmethyloxy group, N-octylaminocarbonylmethyloxy group group, N- methyl -N- benzylaminocarbonyl methyl group, a benzyl group, a cyano methyl _{group, -O- (CH 2) m CO} 2 H and the like.

The aryloxy group represented by R ¹ and R ⁶ is preferably an aryloxy group having 6 to 30 carbon atoms, for example, phenyloxy group, 1-naphthyloxy group, 2-naphthyloxy group, 2 -Chlorophenyloxy group, 2-methylphenyloxy group, 2-methoxyphenyloxy group, 2-butoxyphenyloxy group, 3-chlorophenyloxy group, 3-trifluoromethylphenyloxy group, 3-cyanophenyloxy group, 3 -(2-ethylhexyloxy) phenyloxy group, 3-nitrophenyloxy group, 4-fluorphenylphenyloxy group, 4-
Examples thereof include a cyanophenyloxy group, a 4-butoxyphenyloxy group, a 4- (2-ethylhexyloxy) phenyloxy group and a 4-octadecylphenyloxy group.

The alkylthio group represented by R ¹ and R ⁶ is preferably an alkylthio group having 1 to 30 carbon atoms,
For example, methylthio group, ethylthio group, propylthio group, isopropylthio group, butylthio group, isobutylthio 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-benzylaminocarbonylmethylthio group, benzylthio group,
Cyanomethylthio _{group, -S- (CH 2) m CO} 2 H and the like.

The arylthio group represented by R ¹ and R ⁶ is preferably an arylthio group having 6 to 30 carbon atoms,
For example, phenylthio group, 1-naphthylthio group, 2-naphthylthio group, 2-chlorophenylthio group, 2-methylphenylthio group, 2-methoxyphenylthio group, 2-butoxyphenylthio group, 3-chlorophenylthio group, 3
-Trifluoromethylphenylthio group, 3-cyanophenylthio group, 3- (2-ethylhexyloxy) phenylthio group, 3-nitrophenylthio group, 4-fluorphenylphenyl group, 4-cyanophenylthio group, 4-butoxy Phenylthio group, 4- (2-ethylhexyloxy)
Examples thereof include a phenylthio group and a 4-octadecylphenylthio group.

The alkylcarbonyl group represented by R ^{1 to} R ⁶ is preferably an alkylcarbonyl group having 2 to 20 carbon atoms, for example, acetyl group, propanoyl group, butanoyl group, hexanoyl group, octanoyl group, 2- Ethylhexanoyl group, decanoyl group, dodecanoyl group,
Octadecanoyl group, 2-cyanopropanoyl group, 1,
1-dimethylpropanoyl group and the like. Other examples of the alkylcarbonyl group include those shown below.

[0050]

[Chemical 16]

The arylcarbonyl group represented by R ^{1 to} R ⁶ is preferably an arylcarbonyl group having a carbon number of 6 to 30, and examples thereof include a benzoyl group, a 4-chlorobenzoyl group, a 2-chlorobenzoyl group and 3,5. Examples thereof include dichlorobenzoyl group, 2,4-dichlorobenzoyl group, 3-methylbenzoyl group and 2-methylbenzoyl group. Other examples of the arylcarbonyl group include those shown below.

[0052]

[Chemical 17]

The alkylsulfonyl group represented by R ^{1 to} R ⁶ is preferably an alkylsulfonyl group having 1 to 20 carbon atoms, and examples thereof include a methylsulfonyl group, an ethylsulfonyl group, a propylsulfonyl group, an isopropylsulfonyl group and a butylsulfonyl group. Group, hexylsulfonyl group, cyclohexylsulfonyl group, octylsulfonyl group, 2-
Examples thereof include an ethylhexylsulfonyl group, a decanoylsulfonyl group, a dodecanoylsulfonyl group, an octadecanoylsulfonyl group, a cyanomethylsulfonyl group and a trifluoromethylsulfonyl group.

The arylsulfonyl group represented by R ^{1 to} R ⁶ is preferably an arylsulfonyl group having 6 to 30 carbon atoms, for example, phenylsulfonyl group, 1-naphthylsulfonyl group, 2-naphthylsulfonyl group, 2 -Chlorophenylsulfonyl group, 2-methylphenylsulfonyl group, 2-methoxyphenylsulfonyl group, 2-butoxyphenylsulfonyl group, 3-chlorophenylsulfonyl group, 3-trifluoromethylphenylsulfonyl group, 3-cyanophenylsulfonyl group, 3- (2-Ethylhexyloxy) phenylsulfonyl group, 3-nitrophenylsulfonyl group, 4-fluorphenylphenylsulfonyl group, 4-cyanophenylsulfonyl group, 4-butoxyphenylsulfonyl group, 4- (2-ethylhexyloxy) phenylsul Group, such as 4-octadecyl phenylsulfonyl group.

The carbamoyl group represented by R ¹ and R ⁶ includes N-alkylcarbamoyl group, N-arylcarbamoyl group, N, N-dialkylcarbamoyl group, N, N.
Examples include a -diarylcarbamoyl group and an N-alkyl-N-arylcarbamoyl group. Specifically, a carbamoyl group having 1 to 30 carbon atoms is preferable, and 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 group, N-4-cyanophenylcarbamoyl group, N-methyl-N-phenylcarbamoyl group, N, N-dimethylcarbamoyl group, N, N-dibutylcarbamoyl group, N,
Examples thereof include N-diphenylcarbamoyl group. Examples of the carbamoyl group further include those shown below.

[0056]

[Chemical 18]

The sulfamoyl group represented by R ¹ and R ⁶ includes N-alkylsulfamoyl group, N-arylsulfamoyl group, N, N-dialkylsulfamoyl group and N, N-diarylsulfayl group. Examples thereof include a moyl group and an N-alkyl-N-arylsulfamoyl group.

Specifically, as the sulfamoyl group,
A substituted sulfamoyl group having 0 to 30 carbon atoms is preferable, and examples thereof include N-methylsulfamoyl group, N-ethylsulfamoyl group, N-propylsulfamoyl group, and 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 can be mentioned.

The alkoxycarbonyl group represented by R ^{1 to} R ⁴ and R ⁶ is preferably an alkoxycarbonyl group having 2 to 20 carbon atoms, and examples thereof include a methoxycarbonyl group, an ethoxycarbonyl group, a propoxycarbonyl group and a butoxy group. Carbonyl group, hexyloxycarbonyl group, 2-ethylhexyloxycarbonyl group, octyloxycarbonyl group, decyloxycarbonyl group, octadecyloxycarbonyl group, phenyloxyethyloxycarbonyl group, phenyloxypropyloxycarbonyl group, 2,4-di- t- amylphenyloxy ethylcarbonyl 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.

The aryloxycarbonyl group represented by R ^{1 to} R ⁴ and R ⁶ is preferably an aryloxycarbonyl group having 7 to 30 carbon atoms, for example, 2-methylphenyloxycarbonyl group and 2-chlorophenyl. Oxycarbonyl 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-fluorophenyloxycarbonyl group, 4-chlorophenyloxycarbonyl group, 4-sia Phenyloxycarbonyl group, 4
-Butoxyphenyloxycarbonyl group and the like.

The alkylphosphoryl group represented by R ¹ and R ⁶ is preferably an alkylphosphoryl group having 2 to 40 carbon atoms, and examples thereof include a methylphosphoryl group, an ethylphosphoryl group, a propylphosphoryl group, an isopropylphosphoryl group and a butyl group. Phosphoryl group, isobutylphosphoryl group, sec-butylphosphoryl group, t-butylphosphoryl group, pentylphosphoryl group, isopentylphosphoryl group, hexylphosphoryl group, heptylphosphoryl group, octylphosphoryl group, 2-ethylhexylphosphoryl group, decylphosphoryl group, Dodecylphosphoryl group, octadecylphosphoryl group, ethoxycarbonylmethylphosphoryl group, 2-ethylhexyloxycarbonylmethylphosphoryl group, aminocarbonylmethylphosphoryl group,
N, N-dibutylaminocarbonylmethylphosphoryl group, N-methylaminocarbonylmethylphosphoryl group,
N-ethylaminocarbonylmethylphosphoryl group, N-
Examples thereof include an octylaminocarbonylmethylphosphoryl group and a benzylphosphoryl group.

The arylphosphoryl group represented by R ¹ and R ⁶ is preferably an arylphosphoryl group having 12 to 50 carbon atoms, for example, a phenylphosphoryl group, 1-
Naphthylphosphoryl group, 2-naphthylphosphoryl group, 2
-Chlorophenylphosphoryl group, 2-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-fluorphenyl Examples thereof include a phosphoryl group, a 4-cyanophenylphosphoryl group, a 4-butoxyphenylphosphoryl group, a 4- (2-ethylhexyloxy) phenylphosphoryl group and a 4-octadecylphenylphosphoryl group.

The amino group represented by R ¹ and R ⁶ is N
-Alkylamino group, N-arylamino group, N-acylamino group, N-sulfonylamino group, N, N-dialkylamino group, N, N-diarylamino group, N-alkyl-N-arylamino group, N, Examples thereof include N-disulfonylamino group.

Specifically, the amino group has 0 to 5 carbon atoms.
0 is preferably an amino group, for example, 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-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- (di-2-ethylhexylcarbonyl) amino group, N, N- (dimethylsulfonyl) amino group, N, N- (diethylsulfonyl) amino group, N, N
Examples thereof include a-(dibutylsulfonyl) amino group, an N, N- (2-ethylhexylsulfonyl) amino group and an N, N- (diphenylsulfonyl) amino group. Further, examples of the amino group include the following.

[0065]

[Chemical 19]

[0066]

[Chemical 20]

The dialkylphosphoryl group represented by R ^{2 to} R ⁴ is preferably a dialkylphosphoryl group having 2 to 36 carbon atoms, and examples thereof include dimethylphosphoryl group, diethylphosphoryl group, diisopropylphosphoryl group and di-
Examples include n-butylphosphoryl group and di-t-butylphosphoryl group. The diarylphosphoryl group represented by R ^{2 to} R ⁴ is preferably a diarylphosphoryl group having 12 to 36 carbon atoms, and examples thereof include diphenylphosphoryl group, di- (4-chloro-phenyl) phosphoryl group and di-
(4-methyl-phenyl) phosphoryl group and the like can be mentioned.

The dialkoxyphosphoryl group represented by R ^{2 to} R ⁴ is preferably a dialkoxyphosphoryl group having 2 to 36 carbon atoms, and examples thereof include dimethoxyphosphoryl group, diethoxyphosphoryl group and di-n-propoxyphosphoryl group. Group, a di-n-butoxyphosphoryl group and the like. The diaryloxyphosphoryl group represented by R ^{2 to} R ⁴ is preferably a diaryloxyphosphoryl group having 12 to 36 carbon atoms, and examples thereof include a diphenoxyphosphoryl group, a di- (4-chloro-phenoxy) phosphoryl group,
Examples thereof include a di- (4-methyl-phenoxy) phosphoryl group.

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

Specific examples of the Ar portion of the azo dye represented by the general formula (I) of the present invention are shown below.
To [Chemical Formula 41] and specific examples of the coupler moiety are shown in [Chemical Formula 42] to [Chemical Formula 51], but the present invention is not limited thereto.

<Ar part>

[Chemical 21]

[0072]

[Chemical formula 22]

[0073]

[Chemical formula 23]

[0074]

[Chemical formula 24]

[0075]

[Chemical 25]

[0076]

[Chemical formula 26]

[0077]

[Chemical 27]

[0078]

[Chemical 28]

[0079]

[Chemical 29]

[0080]

[Chemical 30]

[0081]

[Chemical 31]

[0082]

[Chemical 32]

[0083]

[Chemical 33]

[0084]

[Chemical 34]

[0085]

[Chemical 35]

[0086]

[Chemical 36]

[0087]

[Chemical 37]

[0088]

[Chemical 38]

[0089]

[Chemical Formula 39]

[0090]

[Chemical 40]

[0091]

[Chemical 41]

<Coupler part>

[Chemical 42]

[0093]

[Chemical 43]

[0094]

[Chemical 44]

[0095]

[Chemical formula 45]

[0096]

[Chemical formula 46]

[0097]

[Chemical 47]

[0098]

[Chemical 48]

[0099]

[Chemical 49]

[0100]

[Chemical 50]

[0101]

[Chemical 51]

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

The compound represented by the general formula (I) has good hue and light resistance. 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. Further, since the compound has a good affinity with an oily medium, the oily ink composition of the present invention has good storage stability without separation of the dye from the oily medium even when stored for a long time. .

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

Examples of the solid oily medium include beeswax, carnauba wax, rice wax, wood wax, jojoba oil, spermaceti wax, candelilla wax, lanolin, montan wax, ozokerite, ceresin, paraffin wax, microcrystalline wax. , Natural waxes 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, dihydroxystearic acid; dodecanol , Tetradecanol, hexadecanol, eicosanol, docosanol, tetracosanol, hexacosanol, octacosanol, dodecenol, myricyl alcohol, tetracenol, hexadecenol, eicoseno , Docosenol, pinene glycol, hinokiol, butynediol, nonanediol, isophthalyl alcohol, messerine, hexanediol, decanediol, tetradecanediol, hexadecanediol, docosanediol, tetracosandiol, tvneol, phenylglycerin, eicosandi Alcohols such as oat, 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 melicinate; saccharose stearate, saccharose palmitate, saccharose behenate, saccharose laurate, saccharose melicinate, lactose stearate, lactose palmitate, lactose behenate, lactate laurate, melicin. Acid fatty acid esters such as lactose; benzoylacetone, diacetobenzene, benzophenone, Kosanon, heptacosanone,
Ketones such as heptatriacontanone, hentriacontanone, stearone, laurone; oleic acid amide,
Lauric acid amide, stearic acid amide, ricinoleic acid amide, palmitic acid amide, tetrahydrofuranic acid amide, erucic acid amide, myristic acid amide, 12-hydroxystearic acid amide, N-stearyl erucic acid amide, N-oleyl stearic acid amide, N , N-ethylenebislauric acid amide, N, N-ethylenebisstearic acid amide, N, N-ethylenebisbehenic acid amide, N, N-xylylenebisstearic acid amide, N,
N-butylene bisstearic acid amide, N, N-dioleyl adipamic acid amide, N, N-dioleyl sebacic acid amide, N, N-distearyl sebacic acid amide, N,
N-distearyl terephthalic acid amide, phenacetin,
Amides such as toluamide and acetamide; sulfonamides such as p-toluenesulfonamide, ethylbenzenesulfonamide and butylbenzenesulfonamide;
α-methylnaphthalene, β-methylnaphthalene, 2,6
-Alkylnaphthalenes such as dimethylnaphthalene; dibutylnaphthalate, dioctylphthalate, dibutyladipate, dimethyl terephthalate, benzyl benzoate, carboxylic acid esters such as naphthalene-2,6-dicarboxylic acid methyl ester; tributyl phosphate,
And phosphoric acid esters such as triphenyl phosphate.

Examples of the liquid oily medium include one kind or a mixed solvent of two or more kinds of organic solvents. Examples of the organic solvent include alcohols such as ethanol, pentanol, heptanol, octanol, cyclohexanol, benzyl alcohol, phenylethyl alcohol, phenylpropyl alcohol, furfuryl alcohol, 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 and 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 malonate diethyl, 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 and dimethylnaphthalene; acetonitrile, formamide,
N, N-dimethylformamide, N, N-dimethylacetamide, dimethyl sulfoxide, sulfolane, propylene carbonate, N-methyl-2-pyrrolidone, N-
And a polar solvent such as vinyl-2-pyrrolidone or N, N-diethyldodecane amide. These solvents may be used alone or in combination 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 (120 to 200 ° C.) in combination.
When used in combination, the robustness of the image portion of the formed image is improved, and color transfer or the like is less likely to occur even when a plurality of recording sheets on which images are formed are stacked, which is preferable. The oily medium preferably contains a polyamide-based, polyurethane-based, polyester-based, epoxy-based or polyacrylic-based resin compatible with the oily 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 mass based on the total mass of the oil-based ink composition of the present invention. Further, an additive having an action of improving the fastness of the dye, an antioxidant, a singlet oxygen quencher, an ultraviolet absorber and the like may be allowed to coexist.

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 being heated to melt it. The oily medium of the oily ink composition of the present invention is described in JP-A-9-176532.
The vehicle described in the publication can be used, and
The method described in the above publication can also 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 room temperature, it can be used as an ink composition for a so-called hot melt type (or wax jet type) inkjet recording device. In addition, 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 it on a substrate such as cloth or plastic film.
Further, it can be used as a ballpoint pen ink and a marker ink.

[0112]

The present invention will be described in more detail with reference to the following examples, but the present invention is not limited to these examples. Below, the dye compound in the present invention,
Shown as a combination of the Ar portion and the coupler portion shown below. For example, the exemplified compound 2- (1-2) means Ar
It means a combination of the moiety (diazo moiety) represented by 2 in [Chemical Formula 21] and the coupler moiety represented by (1-2) in [Chemical Formula 42]. That is, 2- (1
The compound represented by -2) has the following structure.

[0113]

[Chemical 52]

Example 1 1-Methylnaphthalene 35 parts by mass 2,6-Dimethylnaphthalene 60 parts by mass Dye (Exemplified Compound 2- (1-2)) 5 parts by mass The mixture having the above composition is stirred at 60 ° C. for 5 hours. Then, the dye was dissolved in an oil medium of 1-methylnaphthalene or 2,6-dimethylnaphthalene to prepare an oil-based 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 (Xerox product). When the image portion of the formed image was visually observed, the image portion was free from bleeding and had a good magenta hue. When the image area was rubbed with a hand 10 seconds after the image was recorded, no stain was generated on the background area around the image and the rubbed hand. Furthermore, using a xenon fade meter (product of Suga Test Instruments Co., Ltd.), irradiation was performed for 100 hours.
The discoloration of the image was small. In addition, the above ink composition 6
No separation of dye and medium occurred even after storage at 0 ° C. for 3 months.

<Example 2> 50 parts by mass of dibutyl naphthalate Naphthalene-2,6-dicarboxylic acid diethyl ester 43 parts by mass Dye (Exemplified compound 2- (1-2)) 7 parts by mass Using the mixture having the above composition, An oil-based ink composition 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.

Example 3 Dibutyl Adipate 30 parts by mass Benzyl Benzoate 63 parts by mass Dye (Exemplified Compound 2- (1-2)) 7 parts by mass In the same manner as in Example 1 using the mixture having the above composition, an oil-based ink A composition was made. 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 mass 2-Methylnaphthalene 20 parts by mass Stearic Acid Amide 35 parts by mass Dye (Exemplified Compound 2- (1-2)) 5 parts by mass Implemented using a mixture of the above compositions. An oil-based ink composition 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.

Example 5 Tricresyl Phosphate 65 parts by mass Dibutyl Adipate 31 parts by mass Dye (Exemplified Compound 2- (1-2)) 4 parts by mass In the same manner as in Example 1, using the mixture having the above composition, oiliness An 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.

<Examples 6 to 20> As shown in Table 1 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 area was a good magenta hue.

[0120]

[Table 1]

<Example 21> Tricresyl phosphate 60 parts by mass Dibutyl adipate 20 parts by mass Compound 10 represented by the following structural formula 1 10 parts by mass Dye (Exemplified compound 307- (1-2)) 5 parts by mass Mixture of the above composition 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.

[0122]

[Chemical 53]

<Example 22> Tricresyl phosphate 60 parts by mass Dibutyl adipate 15 parts by mass The compound represented by the structural formula 1 10 parts by mass The compound represented by the structural formula 2 below 10 parts by mass Dye (exemplified compound 31- ( 1-16)) 5 parts by mass Using the mixture having the above composition, 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.

[0124]

[Chemical 54]

<Example 23> An oil-based ink was prepared in the same manner as in Example 22 except that the compound represented by the structural formula 1 was replaced by the compound represented by the structural formula 3 below. 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.

[0126]

[Chemical 55]

[0127]

EFFECTS OF THE INVENTION According to the present invention, it is possible to provide an oil-based ink composition capable of forming an image having a good hue and high storage stability such as light fastness.

   ─────────────────────────────────────────────────── ─── Continued front page    F-term (reference) 2H086 BA01 BA54 BA56                 4J039 AB01 AB04 AB05 AB12 AD01                       BC03 BC07 BC09 BC16 BC19                       BC20 BC33 BC34 BC36 BC40                       BC44 BC50 BC51 BC52 BC53                       BC54 BC55 BC65 CA04 CA07                       EA21 EA35 EA44

Claims (5)

[Claims] 1. An oil-based ink composition containing an oil-based medium and a compound represented by the following general formula (I). [Chemical 1] (In the general formula (I), Ar represents an aryl group or a heterocyclic group. R ¹ represents a hydrogen atom, a halogen atom, a nitrile, a hydroxy group, a nitro group, a carboxyl group, an alkyl group,
Aryl group, alkoxy group, aryloxy group, alkylthio group, arylthio group, alkylcarbonyl group, arylcarbonyl group, alkylsulfonyl group, arylsulfonyl group, carbamoyl group, sulfamoyl group, alkoxycarbonyl group, aryloxycarbonyl group,
It represents an alkylphosphoryl group, an arylphosphoryl group or an amino group. R ^{2 to} R ⁴ are a hydrogen atom, an alkyl group, an aryl group, an alkylcarbonyl group, an arylcarbonyl group, an alkylsulfonyl group, an arylsulfonyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, a dialkylphosphoryl group, a diarylphosphoryl group, and a diarylphosphoryl group. Represents an alkoxyphosphoryl group and a diaryloxyphosphoryl group. R ² and R ³ may combine with each other to form a ring. X
Represents N—R ⁵ , an oxygen atom, and a sulfur atom. R ⁵ represents a hydrogen atom, an alkyl group, an aryl group, an alkylsulfonyl group, an arylsulfonyl group, an alkylcarbonyl group or an arylcarbonyl group. Y represents a C-R ^6, a nitrogen atom. R ⁶ has the same meaning as R ¹ . ) 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). [Chemical 2] (In the general formula (II), R ⁷ and R ⁸ represent a hydrogen atom, an alkyl group, or an aryl group. R ^{9 to} R ¹² are each represented by the claim 1.
Is synonymous with R ¹ of. 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). [Chemical 3] (In the general formula (III), R ^{13 to} R ¹⁵ represent a hydrogen atom, an alkyl group, or an aryl group. R ¹⁶ represents a hydrogen atom, a halogen atom, an alkyl group, an aryl group, an alkoxy group, or an aryloxy group. .) 4. Represented by Ar- in the general formula (I).
The group is a group represented by the following general formula (IV)
The oil-based ink composition according to claim 1. [Chemical 4] (In the general formula (IV), R¹⁷Is a hydrogen atom, an alkyl group or
Represents an aryl group. R ¹⁸, R¹⁹Is hydrogen atom, halogen atom
Child, alkyl group, aryl group, alkoxy group, aryl
It represents an oxy group, an alkylthio group, or an arylthio group. Z
Represents an oxygen atom or a sulfur atom. ) 5. A compound represented by the general formula (I) is represented by the following general formula (I-1), the following general formula (I-2), the following general formula (I-3), or the following general formula (I). 4. The oil-based ink composition according to claim 1, which is a compound represented by -4). [Chemical 5]