JPH0931375A - Recording liquid - Google Patents

Abstract

PROBLEM TO BE SOLVED: To prepare a recording liquid which is excellent in printed-image density, light resistance, and water resistance and has satisfactory storage stabil ity by incorporating a specific azo dye into an aqueous medium. SOLUTION: This recording liquid comprises an aqueous medium and a specific azo dye represented by the formula (wherein R1 is H, CH3 , OCH3 , or NHXR5 ; when R1 is H, CH3 , or OCH3 , then R2 is same as R1 ; when R1 is NHXR5 , then R2 is H, a 1-9C alkyl, or a 1-9C alkoxy; R3 is H, SO3 H, phenyl optionally substituted with COOH, or a 1-3C alkyl substituted with COOH; R4 is H or a 1-3C alkyl substituted with COOH; (m) is 1 or 2; and (n) is 0 or 1). The content of the azo dye is 0.5-5wt.%, based on the whole recording liquid. The aqueous medium is water or a water-soluble organic solvent (e.g. ethylene glycol). The amount of water is 45-95wt.% and that of the organic solvent is 1-50wt.%, based on the whole recording liquid. Urea or the like and a surfactant may be added thereto in an amount of 0.1-10wt.% and 0.001-5.0wt.%, respectively, based on the whole recording liquid.

Description

Detailed Description of the Invention

[0001]

FIELD OF THE INVENTION The present invention relates to a recording liquid. More specifically, the present invention relates to a recording liquid suitable for inkjet recording.

[0002]

2. Description of the Related Art A so-called ink jet recording method has been put to practical use, in which droplets of a recording liquid containing a water-soluble dye such as a direct dye or an acid dye are jetted from a fine ejection orifice to perform recording. With regard to this recording liquid, it is fast to fix to general-purpose recording paper such as PPC (plain paper copier) paper such as electrophotographic paper and fan hold paper (continuous paper such as computers), and printing of printed matter It is required that the quality is good, that is, the print has no bleeding and the contour is clear, and that the stability during storage as a recording liquid is also excellent. Significantly limited.

On the other hand, dyes for recording liquids have sufficient solubility in the above-mentioned limited solvents and are stable even when stored as recording liquids for a long time.
Further, it is required that the density of the printed image is high, and that it is excellent in water resistance and light resistance. However, it has been difficult to satisfy many of these requirements at the same time. Therefore, various methods (for example, JP-A-55-140467, JP-A-55-152747, and JP-A-57-207660) are used.
JP-A-59-22672, JP-A-61-277
6, JP-A-61-57666, JP-A-62-190
269, JP-A-62-190271, JP-A-62-290
190272, JP-A-62-197476, JP-A-62-250082, JP-A-62-246975,
JP-A-62-256974, JP-A-62-28865
9, JP-A-63-8463, JP-A-63-2286
7, JP-A-63-117079, JP-A-63-30
567, JP-A-63-33484, JP-A-63-6
No. 3764, JP-A-63-105079, JP-A-64
JP-A-31877, JP-A-1-93389, JP-A-1-93389
JP 210264, JP-A-1-240584, JP-A-2
-16171, JP-A-2-140270, JP-A-3
-200882, JP-A-5-262998), etc., but have not yet been able to sufficiently satisfy the market requirements.

Further, British Patent (GB) No. 2251625 and JP-A-6-504562 describe that a dye having a structure similar to that of the present invention can be used for ink jet recording. However, these dyes have a structure in which three naphthalene rings are linked via two azo groups, and a dye having such a structure tends to be bronze, and tends to be unable to obtain a sufficient color density.

[0005]

DISCLOSURE OF THE INVENTION The present invention provides good print quality even when recorded on plain paper for ink jet recording, writing, etc., as well as high density of recorded images, light resistance, and especially water resistance. It is an object of the present invention to provide a black recording liquid which has excellent properties and color tone of a recorded image and has good stability when stored for a long period of time.

[0006]

The present inventor has accomplished the present invention by confirming that the above object is achieved when a specific dye is used as a recording liquid component. That is, the gist of the present invention resides in a recording liquid containing an aqueous medium and at least one of the dyes represented by the general formula [I] in the form of the free acid in claim 1.

Hereinafter, the present invention will be described in detail. The dye used in the present invention has a free acid form represented by the general formula [I] in claim 1. In the general formula [I], R
₁ represents H, CH ₃ , an OCH ₃ group or a group represented by the general formula [II], preferably an OCH ₃ group or a general formula [I]
I], and more preferably an OCH ₃ group or a group of the general formula [II] in which X is —CO—.

When R ₁ represents a H, CH ₃ or OCH ₃ group, R ₂ represents a H, CH ₃ or OCH ₃ group, but preferably an OCH ₃ group. When R ₁ represents a group represented by the general formula [II], R ₂ is H, a substituted or unsubstituted alkyl group having 1 to 9 carbon atoms, or a substituted or unsubstituted alkoxy group having 1 to 9 carbon atoms. Group, preferably a substituted or unsubstituted alkoxy group having 1 to 9 carbon atoms.

[0009] R_TwoAs a substituent of the alkyl group represented by
Include a phenyl group, etc., and a substituent of an alkoxy group.
As, alkoxy group, hydroxyl group, hydroxy
Alkoxy group, phenyl group, -COOH group, -COOH
Examples thereof include an alkoxy group substituted with a group. R_ThreeIs
H, -SO_ThreeSubstituted with H group or -COOH group
Optionally substituted with a phenyl group or a -COOH group
Represents an alkyl group having a prime number of 1 to 3, R_FourIs H or -C
Represents an alkyl group having 1 to 3 carbon atoms substituted with an OOH group
But R _FourR represents H, then R_ThreeIs preferably H
Or -SO_ThreeSubstituted with H group or -COOH group
Represents an optional phenyl group, R_FourIs a -COOH group
When a substituted alkyl group having 1 to 3 carbon atoms is represented
Is R_ThreeIs preferably substituted with H or --COOH groups
Represents an alkyl group having 1 to 3 carbon atoms.

In the general formula [II], the aryl group having 6 to 12 carbon atoms represented by R ₅ is an unsubstituted aryl group such as a phenyl group or a naphthyl group, a phenyl group having a substituent such as an alkyl group, or a naphthyl group. A substituted aryl group such as a group (the total number of carbon atoms of the substituent and the aryl group is 6 to
12). The dye used in the present invention may be used as it is in the free acid form represented by the general formula [I], or may be used as it is when it is obtained in a salt form at the time of production, or may be used in a desired salt form. May be converted to Further, a part of the acid groups may be of a salt type, and a salt type dye and a free acid type dye may be mixed. Examples of such a salt type include salts of alkali metals such as Na, Li and K, alkyl groups,
Examples thereof include ammonium salts which may be substituted with a hydroxyalkyl group and organic amine salts. Examples of organic amines include lower alkylamines, hydroxy-substituted lower alkylamines, carboxy-substituted lower alkylamines, and polyamines having 2 to 10 alkyleneimine units having 2 to 4 carbon atoms. For these salt forms,
The kind of the salt is not limited to one kind, and a plurality of kinds of salts may be contained in one molecule of the dye, or dyes having different salt types may be mixed. Specific examples of these dyes include the following Nos. 1 to No. An azo dye having a structure shown in 21 is mentioned.

[0011]

Embedded image

[0012]

Embedded image

[0013]

Embedded image

[0014]

[Chemical 6]

The azo dye represented by the general formula [I] can be obtained by a method known per se [for example, Yutaka Hosoda, "New Dye Chemistry" (published by Gihodo, December 21, 1973) Nos. 396-409.
Page]], a diazotization and coupling step. The content of the dye of the general formula [I] in the recording liquid is preferably 0.5 to 5% by weight, particularly preferably about 2 to 4% by weight, based on the total amount of the recording liquid.

As the aqueous medium used in the present invention, water and water-soluble organic solvents such as ethylene glycol, propylene glycol, butylene glycol, diethylene glycol, triethylene glycol, polyethylene glycol (weight average molecular weight (Mw) = 190 to 4) are used.
00), glycerin, N-methylpyrrolidone, N-ethylpyrrolidone, 1,3-dimethylimidazolidinone, thiodiethanol, dimethylsulfoxide, ethylene glycol monoallyl ether, ethylene glycol monomethyl ether, diethylene glycol monomethyl ether, 2-pyrrolidone, sulfolane ,Ethyl alcohol,
It preferably contains isopropyl alcohol and the like. These water-soluble organic solvents are usually used in the range of 1 to 50% by weight based on the total amount of the recording liquid. On the other hand, water is used in the range of 45 to 95% by weight based on the total amount of the recording liquid.

The recording liquid of the present invention contains 0.
1 to 10% by weight, preferably 0.5 to 5% by weight of urea,
By adding a compound selected from thiourea, biuret, and semicarbazide, and by adding 0.001 to 5.0% by weight of a surfactant, it is possible to further improve quick drying after printing and print quality. it can.

[0018]

EXAMPLES The present invention will now be described in more detail with reference to examples, but the present invention is not limited to these examples as long as the gist thereof is not exceeded. Example 1 10 parts by weight of diethylene glycol, 3 parts by weight of isopropyl alcohol, No. Water was added to 3 parts by weight of dye 1 and the pH was adjusted to 9 with aqueous ammonia to make the total amount 100 parts by weight. This composition was sufficiently mixed and dissolved, filtered under pressure through a Teflon filter having a pore size of 1 μm, and then degassed with a vacuum pump and an ultrasonic cleaner to prepare a recording liquid.

An ink jet printer (trade name: HG-3000, manufactured by Epson) using the obtained recording liquid
Was used to perform inkjet recording on electrophotographic paper (product of Xerox Corporation) to obtain a high density (1.33) black printed matter. Further, various evaluations were carried out by the following methods (a), (b) and (c). The results are shown in Table 1. (A) Light fastness of recorded image: A recording paper was irradiated with a xenon fade meter (manufactured by Suga Test Instruments Co., Ltd.) for 100 hours. Discoloration after irradiation was small.

(B) Water resistance of recorded image: Water resistance test (1) Test method After the recorded image was immersed in tap water for 5 minutes, the bleeding of the image was visually examined. The OD value (printing density) of the solid printed portion before and after the immersion was measured with a Macbeth densitometer (TR927). (2) Test Results As a result of the above, blurring of the image was slight. The change in density of the solid printed portion before and after the above immersion is calculated by the following equation.
The residual rate was 98.6%.

[0021]

OD residual ratio (%) = (OD value after immersion / O before immersion)
D value) x 100

(C) Storage stability of recording liquid: When the recording liquid was sealed in a Teflon container and stored at 5 ° C. and 60 ° C. for 1 month, the change was examined and no precipitation of insoluble matter was observed. It was In the above evaluations of (a), (b), and (c), the visual judgment was evaluated in three grades of ◯: good, Δ: somewhat inferior, and x: defective.

Examples 2 to 4 Nos. Used in Example 1 were used. Instead of the dye of (1), the above No. (6), No. (13) and No.
A recording liquid was prepared by the method of Example 1 except that each of the dyes of (18) was used, and printing was carried out using this to obtain a black recorded product. Furthermore, various evaluations according to (a) to (c) of Example 1 were performed on this recorded material. As a result, good results were obtained in all cases as in Example 1. The OD residual rates were 99.1%, 97.8%, and 99.8%, respectively. The results are shown in Table 1 below.

Comparative Example 1 No. 1 in Example 1 Instead of the dye of (1), C.I.
I. Using Food Black 2, a composition was prepared in the same manner as in Example 1 and then processed to obtain a recording liquid. Using this recording liquid, printing was performed in the same manner as in Example 1 to obtain a black recorded matter. For the obtained recorded matter, (a) to (c) of Example 1
Various evaluations were performed. The results are shown in Table 1 below.

[0025]

[Table 1] ○: Good △: Slightly inferior ×: Poor

Examples 5 to 21 The above-mentioned No. 1 used in Example 1 was used. Instead of the dye of (1), the above No. (2) to (5), No. (7)-(1
2), No. (14) to (17), No. (19) ~
Using each of the dyes of (21), a recording liquid was prepared by the method of Example 1 and printing was carried out to obtain a black recorded matter. Various evaluations according to (a) to (c) of Example 1 were performed on this recorded material. As a result, similar to Example 1, good results were obtained. In addition, dye No. The residual OD of the recording liquid using (2) was 99.5%, and the dye No.
The OD residual rate of the recording liquid using (5) was 97.8%.

[0027]

INDUSTRIAL APPLICABILITY The recording liquid of the present invention is used for ink jet recording, writing instruments, etc., and when recorded on plain paper, a black recorded matter can be obtained, and its printing density, light resistance, and water resistance. In addition to excellent properties, it also has good storage stability as a recording liquid.

─────────────────────────────────────────────────── ───

[Procedure amendment]

[Submission date] August 5, 1996

[Procedure amendment 1]

[Document name to be amended] Statement

[Correction target item name] Detailed description of the invention

[Correction method] Change

[Correction contents]

Detailed Description of the Invention

[0001]

FIELD OF THE INVENTION The present invention relates to a recording liquid. More specifically, the present invention relates to a recording liquid suitable for inkjet recording.

[0002]

2. Description of the Related Art A so-called ink jet recording method has been put to practical use, in which droplets of a recording liquid containing a water-soluble dye such as a direct dye or an acid dye are jetted from a fine ejection orifice to perform recording. With regard to this recording liquid, it is fast to fix to general-purpose recording paper such as PPC (plain paper copier) paper such as electrophotographic paper and fan hold paper (continuous paper such as computers), and printing of printed matter It is required that the quality is good, that is, the print has no bleeding and the contour is clear, and that the stability during storage as a recording liquid is also excellent. Significantly limited.

On the other hand, dyes for recording liquids have sufficient solubility in the above-mentioned limited solvents and are stable even when stored as recording liquids for a long time.
Further, it is required that the density of the printed image is high, and that it is excellent in water resistance and light resistance. However, it has been difficult to satisfy many of these requirements at the same time. Therefore, various methods (for example, JP-A-55-140467, JP-A-55-152747, and JP-A-57-207660) are used.
JP-A-59-22672, JP-A-61-277
6, JP-A-61-57666, JP-A-62-190
269, JP-A-62-190271, JP-A-62-290
190272, JP-A-62-197476, JP-A-62-250082, JP-A-62-246975,
JP-A-62-256974, JP-A-62-28865
9, JP-A-63-8463, JP-A-63-2286
7, JP-A-63-117079, JP-A-63-30
567, JP-A-63-33484, JP-A-63-6
No. 3764, JP-A-63-105079, JP-A-64
JP-A-31877, JP-A-1-93389, JP-A-1-93389
JP 210264, JP-A-1-240584, JP-A-2
-16171, JP-A-2-140270, JP-A-3
-200882, JP-A-5-262998), etc., but have not yet been able to sufficiently satisfy the market requirements.

Further, British Patent (GB) No. 2251625 and JP-A-6-504562 describe that a dye having a structure similar to that of the present invention can be used for ink jet recording. However, these dyes have a structure in which three naphthalene rings are linked via two azo groups, and a dye having such a structure tends to be bronze, and tends to be unable to obtain a sufficient color density.

[0005]

DISCLOSURE OF THE INVENTION The present invention provides good print quality even when recorded on plain paper for ink jet recording, writing, etc., as well as high density of recorded images, light resistance, and especially water resistance. It is an object of the present invention to provide a black recording liquid which has excellent properties and color tone of a recorded image and has good stability when stored for a long period of time.

[0006]

The present inventor has accomplished the present invention by confirming that the above object is achieved when a specific dye is used as a recording liquid component. That is, the gist of the present invention resides in a recording liquid containing an aqueous medium and at least one of the dyes represented by the general formula [I] in the form of the free acid in claim 1.

Hereinafter, the present invention will be described in detail. The dye used in the present invention has a free acid form represented by the general formula [I] in claim 1. In the general formula [I], R
₁ represents H, CH ₃ , an OCH ₃ group or a group represented by the general formula [II], preferably an OCH ₃ group or a general formula [I]
I], and more preferably an OCH ₃ group or a group of the general formula [II] in which X is —CO—.

When R ₁ represents a H, CH ₃ or OCH ₃ group, R ₂ represents a H, CH ₃ or OCH ₃ group, but preferably an OCH ₃ group. When R ₁ represents a group represented by the general formula [II], R ₂ is H, a substituted or unsubstituted alkyl group having 1 to 9 carbon atoms, or a substituted or unsubstituted alkoxy group having 1 to 9 carbon atoms. Group, preferably a substituted or unsubstituted alkoxy group having 1 to 9 carbon atoms.

[0009] R_TwoAs a substituent of the alkyl group represented by
Include a phenyl group, etc., and a substituent of an alkoxy group.
As, alkoxy group, hydroxyl group, hydroxy
Alkoxy group, phenyl group, -COOH group, -COOH
Examples thereof include an alkoxy group substituted with a group. R_ThreeIs
H, -SO_ThreeSubstituted with H group or -COOH group
Optionally substituted with a phenyl group or a -COOH group
Represents an alkyl group having a prime number of 1 to 3, R_FourIs H or -C
Represents an alkyl group having 1 to 3 carbon atoms substituted with an OOH group
But R _FourR represents H, then R_ThreeIs preferably H
Or -SO_ThreeSubstituted with H group or -COOH group
Represents an optional phenyl group, R_FourIs a -COOH group
When a substituted alkyl group having 1 to 3 carbon atoms is represented
Is R_ThreeIs preferably substituted with H or --COOH groups
Represents an alkyl group having 1 to 3 carbon atoms.

In the general formula [II], the aryl group having 6 to 12 carbon atoms represented by R ₅ is an unsubstituted aryl group such as a phenyl group or a naphthyl group, a phenyl group having a substituent such as an alkyl group, or a naphthyl group. A substituted aryl group such as a group (the total number of carbon atoms of the substituent and the aryl group is 6 to
12). The dye used in the present invention may be used as it is in the free acid form represented by the general formula [I], or may be used as it is when it is obtained in a salt form at the time of production, or may be used in a desired salt form. May be converted to Further, a part of the acid groups may be of a salt type, and a salt type dye and a free acid type dye may be mixed. Examples of such a salt type include salts of alkali metals such as Na, Li and K, alkyl groups,
Examples thereof include ammonium salts which may be substituted with a hydroxyalkyl group and organic amine salts. Examples of organic amines include lower alkylamines, hydroxy-substituted lower alkylamines, carboxy-substituted lower alkylamines, and polyamines having 2 to 10 alkyleneimine units having 2 to 4 carbon atoms. For these salt forms,
The kind of the salt is not limited to one kind, and a plurality of kinds of salts may be contained in one molecule of the dye, or dyes having different salt types may be mixed. Specific examples of these dyes include the following Nos. 1 to No. An azo dye having a structure shown in 21 is mentioned.

[0011]

Embedded image

[0012]

Embedded image

[0013]

Embedded image

[0014]

[Chemical 6]

The azo dye represented by the general formula [I] can be obtained by a method known per se [for example, Yutaka Hosoda, "New Dye Chemistry" (published by Gihodo, December 21, 1973) Nos. 396-409.
Page]], a diazotization and coupling step. The content of the dye of the general formula [I] in the recording liquid is preferably 0.5 to 5% by weight, particularly preferably about 2 to 4% by weight, based on the total amount of the recording liquid.

As the aqueous medium used in the present invention, water and water-soluble organic solvents such as ethylene glycol, propylene glycol, butylene glycol, diethylene glycol, triethylene glycol, polyethylene glycol (weight average molecular weight (Mw) = 190 to 4) are used.
00), glycerin, N-methylpyrrolidone, N-ethylpyrrolidone, 1,3-dimethylimidazolidinone, thiodiethanol, dimethylsulfoxide, ethylene glycol monoallyl ether, ethylene glycol monomethyl ether, diethylene glycol monomethyl ether, 2-pyrrolidone, sulfolane ,Ethyl alcohol,
It preferably contains isopropyl alcohol and the like. These water-soluble organic solvents are usually used in the range of 1 to 50% by weight based on the total amount of the recording liquid. On the other hand, water is used in the range of 45 to 95% by weight based on the total amount of the recording liquid.

The recording liquid of the present invention contains 0.
1 to 10% by weight, preferably 0.5 to 5% by weight of urea,
By adding a compound selected from thiourea, biuret, and semicarbazide, and by adding 0.001 to 5.0% by weight of a surfactant, it is possible to further improve quick drying after printing and print quality. it can.

[0018]

EXAMPLES The present invention will now be described in more detail with reference to examples, but the present invention is not limited to these examples as long as the gist thereof is not exceeded. Example 1 10 parts by weight of diethylene glycol, 3 parts by weight of isopropyl alcohol, No. Water was added to 3 parts by weight of dye 1 and the pH was adjusted to 9 with aqueous ammonia to make the total amount 100 parts by weight. This composition was sufficiently mixed and dissolved, filtered under pressure through a Teflon filter having a pore size of 1 μm, and then degassed with a vacuum pump and an ultrasonic cleaner to prepare a recording liquid.

An ink jet printer (trade name: HG-3000, manufactured by Epson) using the obtained recording liquid
Was used to perform inkjet recording on electrophotographic paper (product of Xerox Corporation) to obtain a high density (1.33) black printed matter. Further, various evaluations were carried out by the following methods (a), (b) and (c). The results are shown in Table 1. (A) Light fastness of recorded image: A recording paper was irradiated with a xenon fade meter (manufactured by Suga Test Instruments Co., Ltd.) for 100 hours. Discoloration after irradiation was small.

(B) Water resistance of recorded image: Water resistance test (1) Test method After the recorded image was immersed in tap water for 5 minutes, the bleeding of the image was visually examined. The OD value (printing density) of the solid printed portion before and after the immersion was measured with a Macbeth densitometer (TR927). (2) Test Results As a result of the above, blurring of the image was slight. The change in density of the solid printed portion before and after the above immersion is calculated by the following equation.
The residual rate was 98.6%.

[0021]

OD residual ratio (%) = (OD value after immersion / O before immersion)
D value) x 100

(C) Storage stability of recording liquid: When the recording liquid was sealed in a Teflon container and stored at 5 ° C. and 60 ° C. for 1 month, the change was examined and no precipitation of insoluble matter was observed. It was In the above evaluations of (a), (b), and (c), the visual judgment was evaluated in three grades of ◯: good, Δ: somewhat inferior, and x: defective.

Examples 2 to 4 Nos. Used in Example 1 were used. Instead of the dye of (1), the above No. (6), No. (13) and No.
A recording liquid was prepared by the method of Example 1 except that each of the dyes of (18) was used, and printing was carried out using this to obtain a black recorded product. Furthermore, various evaluations according to (a) to (c) of Example 1 were performed on this recorded material. As a result, good results were obtained in all cases as in Example 1. The OD residual rates were 99.1%, 97.8%, and 99.8%, respectively. The results are shown in Table 1 below.

Comparative Example 1 No. 1 in Example 1 Instead of the dye of (1), C.I.
I. Using Food Black 2, a composition was prepared in the same manner as in Example 1 and then processed to obtain a recording liquid. Using this recording liquid, printing was performed in the same manner as in Example 1 to obtain a black recorded matter. For the obtained recorded matter, (a) to (c) of Example 1
Various evaluations were performed. The results are shown in Table 1 below.

Examples 5 to 21 Nos. Used in Example 1 were used. Instead of the dye of (1), the above No. (2) to (5), No. (7)-(1
2), No. (14) to (17), No. (19) ~
Using each of the dyes of (21), a recording liquid was prepared by the method of Example 1 and printing was carried out to obtain a black recorded matter. Various evaluations according to (a) to (c) of Example 1 were performed on this recorded material. As a result, similar to Example 1, good results were obtained. In addition, dye No. The residual OD of the recording liquid using (2) was 99.5%, and the dye No.
The OD residual rate of the recording liquid using (5) was 97.8%.

Comparative Example 2 No. 1 in Example 1 Instead of the dye of (1), the following structural formula R described in JP-A-6-220377
A composition was prepared in the same manner as in Example 1 using the compound of No. 1 and then treated to obtain a recording liquid. Using the recording liquid,
Printing was performed in the same manner as in Example 1 to obtain a black recorded material. Various evaluations according to (a) to (c) of Example 1 were performed on the obtained recorded matter. The results are shown in Table 1 below.

[0027]

[Chemical 7]

[0028]

[Table 1] ○: Good △: Slightly inferior ×: Poor

[0029]

INDUSTRIAL APPLICABILITY The recording liquid of the present invention is used for ink jet recording, writing instruments, etc., and when recorded on plain paper, a black recorded matter can be obtained, and its printing density, light resistance, and water resistance. In addition to excellent properties, it also has good storage stability as a recording liquid.

Claims (3)

[Claims] 1. A recording liquid characterized in that the form of the aqueous medium and the free acid contains at least one dye selected from the dyes represented by the following general formula [I]. Embedded image [In the formula, R ₁ represents a H, CH ₃ , OCH ₃ group or a group represented by the following general formula [II], and when R ₁ represents a H, CH ₃ or OCH ₃ group, R ₂ represents When H, CH ₃ or OCH ₃ group is represented and R ₁ is a group represented by the general formula [II], R ₂ is H, a substituted or unsubstituted alkyl group having 1 to 9 carbon atoms, or Represents a substituted or unsubstituted alkoxy group having 1 to 9 carbon atoms, R ₃ is H, —SO
Phenyl group which may be substituted with ₃ H group or -COOH group, or carbon number of 1-3 substituted with -COOH group
R ₄ represents an alkyl group having 1 to 3 carbon atoms substituted with H or a —COOH group, m represents a number of 1 or 2, and n represents a number of 0 or 1. ## STR00002 ## --NHXR ₅ ... [II] (wherein, X represents --CO-- or --SO _2- , and R ₅ is an alkyl group having 1 to 6 carbon atoms or an aryl group having 6 to 12 carbon atoms. Represents).)] 2. In the general formula [I], R ₁ represents a group represented by the general formula [II], and R ₂ has 1 to 1 carbon atoms.
The recording liquid according to claim 1, further comprising at least one dye selected from dyes having a structure represented by 9 of substituted or unsubstituted alkoxy groups. 3. In the general formula [I], R₁And R
_TwoBoth are -OCH _ThreeSelected from dyes with structures represented by groups
Characterized by containing at least one dye
The recording liquid according to claim 1.