JP6654526B2 - Method for producing coloring composition, coloring composition, and coloring agent - Google Patents

Description

  The present invention relates to a method for producing a coloring composition useful as a material for producing a color filter used in a color liquid crystal display device, a color image pickup tube element, and the like.

  In recent years, color filters have been required to have higher definition, higher brightness, and higher contrast. To meet such demands, for example, it has been proposed to improve brightness and contrast by using a combination of a conventional pigment and an organic solvent-soluble dye (Patent Documents 1 and 2). A coloring composition comprising a xanthene dye and a specific conjugate base has also been proposed (Patent Document 3).

JP 2010-32999 A JP 2010-254964 A JP 2012-107192 A

  When manufacturing a color liquid crystal display device, a transparent electrode for driving the liquid crystal is formed on the color filter by vapor deposition or sputtering, and an alignment film for aligning the liquid crystal in a certain direction is also formed. For this reason, when forming a transparent electrode or an alignment film, the color filter is exposed to a high temperature condition of 200 to 230 ° C. or higher. However, in the case of the methods proposed in Patent Documents 1 and 2, since the heat resistance of the organic solvent-soluble dye is insufficient, the brightness of the formed color filter may be insufficient.

  Although the coloring composition proposed in Patent Document 3 has a certain degree of heat resistance, it cannot always be said that it has sufficient performance. Furthermore, the coloring composition proposed in Patent Document 3 contains a xanthene dye having high solubility in an organic solvent as an essential component. May dissolve easily. For this reason, a problem such as “bleeding” may occur in the pattern. Therefore, there has been a strong demand for developing a coloring composition having a good balance between heat resistance and solvent resistance while using a xanthene dye.

  The present invention has been made in view of such problems of the related art, and has as its object to produce a color filter having excellent brightness, contrast, heat resistance, and solvent resistance. An object of the present invention is to provide a possible coloring composition and a method for producing the same. Another object of the present invention is to provide a colorant capable of producing a color filter having excellent brightness, contrast, heat resistance, and solvent resistance.

That is, according to the present invention, a method for producing a coloring composition described below is provided.
[1] C.I. I. Pigment Red 177 and a colorant solution obtained by dissolving a xanthene dye represented by the following general formula (1) in concentrated sulfuric acid, and water to mix the water with water to form a colored composition. Production method.

(In the general formula (1), R _{1 to} R ₄ each independently represent an alkyl group having 1 to 8 carbon atoms.)

  [2] The method for producing a coloring composition according to [1], wherein the coloring material solution is added to a large amount of the flowing water, and the coloring material solution and the water are mixed.

Further, according to the present invention, there are provided the following coloring compositions.
[3] A colored composition produced by the method for producing a colored composition according to [1] or [2].

Further, according to the present invention, the following coloring agents are provided.
[4] A coloring agent containing the coloring composition according to [3].
[5] The coloring agent according to the above [4], which is used for producing a color filter.

  ADVANTAGE OF THE INVENTION According to this invention, the coloring composition which can manufacture the color filter excellent in brightness, contrast, heat resistance, and solvent resistance, and its manufacturing method can be provided. Further, according to the present invention, it is possible to provide a colorant capable of producing a color filter having excellent brightness, contrast, heat resistance, and solvent resistance.

4 is an electron microscope (TEM) photograph showing the particle structure of the coloring composition (A-1) obtained in Example 1. 13 is an electron microscope (TEM) photograph showing the particle structure of the coloring composition (A-5) obtained in Example 5.

<Coloring composition and manufacturing method thereof>
Hereinafter, embodiments of the present invention will be described, but the present invention is not limited to the following embodiments. The method for producing the coloring composition of the present invention is described in C.I. I. Pigment Red 177 and a colorant solution obtained by dissolving a xanthene dye represented by a predetermined general formula in concentrated sulfuric acid, and water to mix the water with water to precipitate a coloring composition. Hereinafter, the details will be described.

(Deposition process)
The method for producing the coloring composition of the present invention is described in C.I. I. Pigment Red 177 and a colorant solution obtained by dissolving a xanthene dye represented by the following general formula (1) in concentrated sulfuric acid, and water to mix the mixture with water to precipitate a coloring composition (precipitation step). .

In the general formula (1), R _{1 to} R ₄ each independently represent an alkyl group having 1 to 8 carbon atoms. Examples of the alkyl group having 1 to 8 carbon atoms include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, and a hexyl group. These alkyl groups may be linear or branched. R _{1 to} R ₄ are each independently preferably an alkyl group having 1 to 4 carbon atoms, and more preferably a methyl group, an ethyl group, or a propyl group. The xanthene dye is particularly preferably a compound represented by the following formula (c).

  Xanthene dyes can be easily synthesized according to known methods. For example, a method of reacting benzaldehyde-2-sulfonic acid with N-substituted-m-aminophenols, as described in "Theoretical Production Dye Chemistry" (Toyo Hosoda, Gihodo, 1957). is there. Incidentally, examples of the N-substituted-m-aminophenols include dimethylaminophenol and diethylaminophenol. Further, using a compound (a) represented by the following formula (a) as a starting material as disclosed in JP-A-10-88047, the compound (a) and a compound having an amino group are used. And the like.

  Examples of the compound having an amino group to be reacted with the compound (a) include methylaniline, dimethylaniline, trimethylaniline, fluoroaniline, chloroaniline, bromoaniline and the like.

  In the precipitation step, the coloring composition is precipitated by mixing the coloring material solution and water. The coloring material solution is C.I. I. Pigment Red 177 and a predetermined xanthene dye can be dissolved in concentrated sulfuric acid. As the concentrated sulfuric acid, it is preferable to use concentrated sulfuric acid (aqueous sulfuric acid solution) having a concentration of 65 to 98% by mass, and it is more preferable to use concentrated sulfuric acid (aqueous sulfuric acid solution) having a concentration of 80 to 90% by mass. When the sulfuric acid concentration of the aqueous sulfuric acid solution is less than 65% by mass, C.I. I. Pigment Red 177 may not be sufficiently dissolved. On the other hand, when the sulfuric acid concentration of the aqueous sulfuric acid solution is more than 98% by mass, the xanthene dye may be easily decomposed.

  C. I. The temperature at which Pigment Red 177 and the xanthene dye are dissolved in concentrated sulfuric acid is preferably from 20 to 80C, more preferably from 40 to 60C. C. I. Pigment Red 177 and the xanthene dye are dissolved in concentrated sulfuric acid at a temperature of less than 20 ° C. I. Pigment Red 177 may be difficult to sufficiently dissolve. On the other hand, if it is higher than 80 ° C., the xanthene dye may be easily decomposed.

  C. dissolved in concentrated sulfuric acid I. The amounts of Pigment Red 177 and xanthene dye may be appropriately set according to the intended use of the coloring composition and the like. The amount of xanthene dye dissolved in concentrated sulfuric acid depends on the amount of C.I. I. Pigment Red 177 is 100 parts by mass, for example, 1 to 30 parts by mass, preferably 1 to 20 parts by mass.

  C. I. Pigment Red 177 and the xanthene dye may be added to and dissolved in concentrated sulfuric acid at the same time, or each may be added stepwise and dissolved. Hardly soluble C.I. I. Pigment Red 177 is dissolved in a high-concentration aqueous sulfuric acid solution under high-temperature conditions, then the sulfuric acid concentration and the temperature of the aqueous sulfuric acid solution are reduced, and then the xanthene dye is added and dissolved to suppress the sulfonation of the xanthene dye. Preferred because it can be. More specifically, the C.I. I. After adding Pigment Red 177 and dissolving at 20 to 80 ° C., the sulfuric acid concentration of the aqueous sulfuric acid solution is reduced to 65 to 90% by mass. Further, it is preferable to adjust the temperature of the aqueous sulfuric acid solution to 40 to 60 ° C. and then add and dissolve the xanthene dye.

  C. I. Pigment Red 177 and a predetermined xanthene dye are dissolved in concentrated sulfuric acid, and a coloring material solution prepared by mixing with water can precipitate a coloring composition. For example, if a coloring material solution is added to a large amount of water or ice water and mixed, a particulate colored composition can be precipitated. If necessary, water to which a water-soluble organic solvent has been added may be used. Above all, it is preferable to add a coloring material solution to a large amount of water flowing at a high speed and mix the coloring material solution with water, because a coloring composition having a smaller particle diameter can be precipitated. As a method for adding the colorant solution to a large amount of flowing water, for example, a method using an aspirator (water flow pump) directly connected to a tap of a tap is preferable. Specifically, if the water that has flowed in from the water inlet of the aspirator directly connected to the faucet is discharged from the water outlet and the colorant solution is sucked up from the air inlet, a large amount of water that flows at high speed inside the aspirator And the color material solution are brought into contact with each other and gradually mixed, whereby a colored composition having a smaller particle size can be precipitated.

(Coloring composition)
After the precipitation step, the colored composition of the present invention can be obtained, for example, by filtering the precipitate and subjecting it to steps such as washing and drying as necessary. The coloring composition of the present invention produced in this manner includes C.I. I. Pigment Red 177 and a xanthene dye are different from a mixture in which the xanthene dye is simply contained, but are excellent in heat resistance and solvent resistance. Further, since the coloring composition of the present invention contains a xanthene dye, C.I. I. As compared with a case where only a pigment such as Pigment Red 177 is used, a colored material such as a color filter having more excellent brightness and contrast can be produced.

  The shape of the coloring composition of the present invention is, for example, particulate. The volume average particle diameter (MV) of the particulate colored composition is preferably 100 nm or less, more preferably 20 to 40 nm. By using a coloring composition having a smaller particle size, a color filter having more excellent contrast can be manufactured.

  In order to further enhance the performance of the coloring composition of the present invention, the coloring composition may be pigmented by a desired pigmentation method. Examples of the pigmentation method include solvent salt milling, salt milling, dry milling, and solvent treatment.

<Colorant>
By using the coloring composition of the present invention, a coloring agent capable of producing a color filter having excellent brightness, contrast, heat resistance and solvent resistance can be prepared. That is, the colorant of the present invention contains the above-described coloring composition, and is suitable as a colorant for producing a color filter (colorant for CF).

  Examples of the components other than the coloring composition contained in the coloring agent include general components used for ordinary coloring agents. For example, components such as an organic solvent, a binder resin, and a dispersant can be appropriately selected and blended. Furthermore, if a photocurable resin, a photopolymerizable compound, a photopolymerization initiator, a sensitizer and the like are blended, a photosensitive colorant (photosensitive colored resin composition) can be obtained.

  Hereinafter, the present invention will be specifically described based on examples, but the present invention is not limited to these examples. In the Examples and Comparative Examples, “parts” and “%” are based on mass unless otherwise specified.

<Synthesis of xanthene dye>
(Synthesis example 1)
A mixture of 50 parts of the compound (a) represented by the following formula (a), 135 parts of isopropyl alcohol, and 27 parts of ethylamine was placed in a flask equipped with a cooling tube and a stirring device, and stirred at 120 ° C. for 18 hours to perform a reaction. I let it. After cooling to room temperature, the obtained reaction solution was added dropwise to 240 parts of 17.5% hydrochloric acid, and the mixture was stirred at room temperature for 1 hour. The precipitate was collected by filtration, washed with pure water at 80 ° C., and dried at 60 ° C. to obtain 51 parts of dark red crystals (compound (b) represented by the following formula (b)). 10 parts of the obtained compound (b), 64 parts of 1-methyl-2-pyrrolidinone, 4 parts of potassium carbonate, and 8 parts of ethyl iodide were mixed and stirred at 80 ° C. for 2 hours. After allowing to cool to room temperature, the obtained reaction solution was dropped into 250 parts of 17.5% hydrochloric acid at 0 to 10 ° C, and the mixture was stirred for 1 hour. The precipitate was collected by filtration and dried at 60 ° C. to obtain 8 parts of deep red crystals (compound (c) represented by the following formula (c)).

(Synthesis example 2)
A mixture of 50 parts of a compound (a) represented by the following formula (a), 135 parts of isopropyl alcohol, and 36 parts of 2,6-xylidine is placed in a flask equipped with a condenser and a stirrer at 120 ° C. for 18 hours. The reaction was carried out with stirring. After cooling to room temperature, the obtained reaction solution was added dropwise to 240 parts of 17.5% hydrochloric acid, and the mixture was stirred at room temperature for 1 hour. The precipitate was collected by filtration, washed with pure water at 80 ° C., and dried at 60 ° C. to obtain 69 parts of dark red crystals (compound (d) represented by the following formula (d)).

(Synthesis example 3)
A mixture of 50 parts of a compound (a) represented by the following formula (a), 135 parts of isopropyl alcohol, and 18 parts of 2,6-xylidine is placed in a flask equipped with a condenser and a stirrer at 80 ° C. for 15 hours. The reaction was carried out with stirring. After cooling to room temperature, the obtained reaction solution was added dropwise to 240 parts of 17.5% hydrochloric acid, and the mixture was stirred at room temperature for 1 hour. The precipitate was collected by filtration, washed with pure water at 80 ° C, and dried at 60 ° C to obtain 48 parts of deep orange crystals (compound (e) represented by the following formula (e)). 10 parts of the obtained compound (e), 50 parts of ethylene glycol, and 7 parts of o-toluidine were mixed and stirred at 120 ° C for 18 hours. After cooling to room temperature, the obtained reaction solution was added dropwise to 200 parts of 17.5% hydrochloric acid, and the mixture was stirred at room temperature for 1 hour. The precipitate was collected by filtration, washed with pure water at 80 ° C., and dried at 60 ° C. for 24 hours to obtain 11 parts of dark red crystals (compound represented by the following formula (f)). 10 parts of the obtained compound (f), 70 parts of 1-methyl-2-pyrrolidinone, 4 parts of potassium carbonate and 8 parts of ethyl iodide were mixed and stirred at 80 ° C. for 2 hours. After cooling to room temperature, the obtained reaction solution was added dropwise to 250 parts of 17.5% hydrochloric acid at 0 to 10 ° C, and the mixture was stirred for 1 hour. The precipitate was collected by filtration, and dried at 60 ° C. to obtain 8 parts of deep red crystals (compound (g) represented by the following formula (g)).

<Preparation of dye composition>
(Preparation Example 1)
A flask equipped with a condenser and a stirrer was charged with 10 parts of Acid Red 289 (manufactured by Daiwa Kasei Co., Ltd.), 70 parts of chloroform, and 5 parts of N, N-dimethylformamide, and the internal temperature was kept at 10 ° C. or lower under stirring. While stirring, 7 parts of thionyl chloride was added dropwise. After completion of the dropwise addition, the temperature was raised to 50 ° C., and the mixture was stirred and reacted for 5 hours. After cooling to 10 ° C., 6 parts of 2-ethylhexylamine and 16 parts of triethylamine were sequentially added dropwise, and reacted at room temperature for 15 hours. The obtained reaction mixture was concentrated, 35 parts of methanol was added, and the mixture was concentrated again until the liquid amount became about half. A reaction product obtained by adding 45 parts of methanol and 5 parts of acetic acid and reacting for 30 minutes was poured into 75 parts of ion-exchanged water for crystallization. The obtained crystals are collected by filtration, washed successively with 50 parts of a 50% aqueous methanol solution, 150 parts of a 5% aqueous hydrochloric acid solution, and 50 parts of deionized water, and then dried at 60 ° C. to obtain a red-violet solid (dye composition ( h)) 7 parts are obtained.

(Preparation Example 2)
8 parts of a dye composition (i) was obtained in the same manner as in Preparation Example 1 described above, except that Acid Red 52 (manufactured by Daiwa Kasei Co., Ltd.) was used instead of Acid Red 289.

<Production of coloring composition>
(Example 1)
To 1,192 parts of an 80% aqueous sulfuric acid solution was added C.I. I. Pigment Red 177 (100 parts) and stirred at 60 ° C. for 3 hours. After cooling to 40 ° C., 5 parts of compound (c) was added, and the mixture was stirred for 1 hour to obtain a coloring material solution. The coloring material solution obtained from the suction port of the aspirator directly connected to the tap was sucked up and mixed with 3,000 mL of water. The precipitate was collected by filtration, washed with water until the filtrate became neutral, and dried at 80 ° C. to obtain 98 parts of a coloring composition (A-1). An electron microscope (TEM) photograph showing the particle structure of the obtained coloring composition (A-1) is shown in FIG.

(Example 2)
97 parts of a coloring composition (A-2) was obtained in the same manner as in Example 1 except that a 90% aqueous sulfuric acid solution was used instead of the 80% aqueous sulfuric acid solution.

(Example 3)
C. in 80% aqueous sulfuric acid. I. Pigment Red 177 was added and the mixture was stirred at 40 ° C., and 93 parts of a coloring composition (A-3) was obtained in the same manner as in Example 1 described above.

(Example 4)
To 1,192 parts of an 80% aqueous sulfuric acid solution was added C.I. I. Pigment Red 177 (100 parts) and Compound (c) (5 parts) were added, and the mixture was stirred at 60 ° C. for 3 hours to obtain a coloring material solution. The coloring material solution obtained from the suction port of the aspirator directly connected to the tap was sucked up and mixed with 3,000 mL of water. The precipitate was collected by filtration, washed with water until the filtrate became neutral, and dried at 80 ° C. to obtain 98 parts of a coloring composition (A-4).

(Example 5)
99 parts of a coloring composition (A-5) was obtained in the same manner as in Example 1 except that the coloring material solution was added to 3,000 mL of water without using an aspirator. FIG. 2 shows an electron microscope (TEM) photograph showing the particle structure of the obtained coloring composition (A-5).

(Comparative Example 1)
Except that the compound (d) was used in place of the compound (c), 99 parts of a coloring composition (A-6) was obtained in the same manner as in Example 1 described above.

(Comparative Example 2)
Except that the compound (g) was used instead of the compound (c), 98 parts of a coloring composition (A-7) was obtained in the same manner as in Example 1 described above.

(Comparative Example 3)
98 parts of a coloring composition (A-8) was obtained in the same manner as in Example 1 except that Acid Red 289 (manufactured by Daiwa Kasei Co., Ltd.) was used instead of the compound (c).

(Comparative Example 4)
100 parts of a coloring composition (A-9) was obtained in the same manner as in Example 1 except that Acid Red 52 (manufactured by Daiwa Kasei Co., Ltd.) was used instead of the compound (c).

(Comparative Example 5)
Except that the dye composition (h) was used in place of the compound (c), 100 parts of a coloring composition (A-10) was obtained in the same manner as in Example 1 described above.

(Comparative Example 6)
Except that the dye composition (i) was used in place of the compound (c), 100 parts of a coloring composition (A-11) was obtained in the same manner as in Example 1 described above.

  Table 1 shows a summary of the produced coloring compositions.

<Preparation of CF colorant (pigment dispersion liquid)>
(Example 6)
The following components were mixed and stirred until uniform, and then dispersed using a paint conditioner and zirconia beads having a diameter of 0.5 mm for 3 hours to obtain a dispersion. 24 parts of propylene glycol-1-monomethyl ether-2-acetate was added to 96 parts of the dispersion filtered with a filter. After dispersing for 3 hours using zirconia beads having a diameter of 0.1 mm using a paint conditioner, the mixture was filtered through a filter to obtain a colorant for CF (DA-1). Volume average particles of the coloring composition (A-1) in the coloring agent (DA-1) measured using a particle size distribution analyzer (trade name "Nanotrack UPA-UT", manufactured by Microtrac Bell Inc.) The diameter (MV) was 36.4 nm.
-Coloring composition (A-1): 15.0 parts-Dispersant solution (trade name "BYK LPN-6919", manufactured by BYK Chemie): 10.0 parts-Binder resin solution (trade name "SPC-2000", (Showa Denko KK): 17.1 parts ・ Propylene glycol-1-monomethyl ether-2-acetate: 57.9 parts

(Examples 7 to 10, Comparative Examples 7 to 12)
Instead of using the coloring composition (A-1) in place of the coloring composition (A-1), each of the coloring compositions (A-2) to (A-11) shown in Table 2 was used in the same manner as in Example 6 described above. Colorants (DA-2) to (DA-11) were obtained. Volume average particles of the coloring composition (A-5) in the coloring agent (DA-5) measured using a particle size distribution measuring device (trade name “Nanotrack UPA-UT”, manufactured by Microtrac Bell Inc.) The diameter (MV) was 40.3 nm.

(Comparative Example 13)
Instead of the coloring composition (A-1), C.I. I. Pigment Red 177 (manufactured by Dainichi Seika Kogyo Co., Ltd.) and the colorant for CF (DA-12) in the same manner as in Example 6 except that 0.75 part of the dye composition (i) was used. I got

(Comparative Example 14)
Instead of the coloring composition (A-1), C.I. I. A colorant for CF (DA-13) was obtained in the same manner as in Example 6 except that Pigment Red 177 (manufactured by Dainichi Seika Kogyo) was used.

<Evaluation (1)>
(contrast)
A colorant for CF was applied to a glass substrate using a spinner, dried at 90 ° C. for 2 minutes, and then heated at 230 ° C. for 30 minutes to form a coating film. Brightness and darkness of the three coating films formed by changing the speed of the spinner were measured using a contrast meter (manufactured by Tsubosaka Electric Co., Ltd.), and the contrast (brightness / darkness) was calculated. The chromaticity x of the coating film was measured using a spectrophotometer (trade name “U-3310”, manufactured by Hitachi, Ltd.). An approximate straight line was created by plotting the chromaticity x and the contrast on a graph, and the contrast value at the chromaticity x = 0.620 was read. Then, a relative value (%) was calculated, where the contrast value of the coating film formed with the CF pigment colorant of Comparative Example 14 was 100%. Table 2 shows the results.

(brightness)
Using a spectrophotometer (trade name “U-3310”, manufactured by Hitachi, Ltd.), the coating film formed on the glass substrate formed in the evaluation of the “contrast” was used in a CIE XYZ color system using a C light source. The lightness was measured. In addition, in order to evaluate correctly, it converted into the brightness at x = 0.650 and y = 0.323 by simulation. Table 2 shows the results.

(Liquidity)
Using an E-type viscometer, the viscosity (mPa · s) immediately after (initial) preparation of the colorant for CF and the viscosity (mPa · s) after standing at 45 ° C. for one week were measured. The measurement conditions were as follows: temperature: room temperature (25 ° C.), and rotor rotation speed: 60 rpm. Table 2 shows the results.

(Heat-resistant)
The lightness after drying at 90 ° C. (prebake) and the lightness after heating at 230 ° C. (postbake) were measured for the coating film formed on the glass substrate in the evaluation of the “contrast”. Then, a difference in lightness of the coating film (= brightness of post-bake−brightness of pre-bake) was calculated, and heat resistance was evaluated according to the following criteria. Table 2 shows the results.
：: Lightness difference is 0 or more Δ: Lightness difference is -0.1 or more and less than 0 ×: Lightness difference is less than -0.1

<Preparation of photosensitive colored resin composition>
(Example 11)
The following components were mixed to obtain a photosensitive colored resin composition (R-1).
-Coloring agent (DA-1): 9 parts-Acrylic resin solution: 1.48 parts-Dipentaerythritol hexaacrylate (photopolymerizable compound, trade name "KAYARAD DPHA", manufactured by Nippon Kayaku Co., Ltd.): 0.57 parts・ Alkylphenone-based photopolymerization initiator (trade name “Irgacure 907”, manufactured by BASF): 0.087 parts ・ 4,4′-bis (diethylamino) benzophenone (photopolymerization initiator, trade name “EAB-F”) , Manufactured by Hodogaya Chemical Co.): 0.02 parts

(Examples 12 to 15, Comparative Examples 15 to 20)
Instead of the coloring agent (DA-1), coloring agents (DA-2) to (DA-6), (DA-8), and (DA-10) to (DA-13) of the types shown in Table 3 were used. Except for using each, photosensitive color resin compositions (R-2) to (R-11) were obtained in the same manner as in Example 11 described above.

<Evaluation (2)>
(Solvent resistance)
After the photosensitive colored resin composition was applied on a glass substrate by a spin coating method, it was prebaked at 90 ° C. for 2 minutes. After cooling, the glass substrate was irradiated with light using an exposure machine (trade name “UX-1000SM”, manufactured by Ushio Inc.) at an exposure amount of 65 mJ / cm ² (based on 365 nm) in an air atmosphere. Next, the glass substrate was placed in an oven and post-baked at 230 ° C. for 30 minutes to form a coating film. After cooling, the film thickness of the formed coating film was measured using a film thickness measurement device (trade name “DEKTAK6M”, manufactured by ULVAC), and was 1.7 μm. The test piece was immersed in a petri dish containing propylene glycol-1-monomethyl ether-2-acetate for 30 minutes, and the chromaticity value of the sample before and after immersion was measured by a spectrophotometer (trade name “U-3310”). , Manufactured by Hitachi, Ltd.), and the color difference ΔEab ^* was calculated from the following formula (I).
^{ΔEab * = [{L * (} 2) -L * (1)} 2 + {a * (2) -a * (1)} 2 + {b * (2) -b * (1)} 2] 1 ^/ 2 ··· (I)

Next, the solvent resistance of the coating film was evaluated according to the following criteria. Table 3 shows the results.
：: ΔEab ^* is less than 0.5 Δ: ΔEab ^* is 0.5 or more and less than 1.0 ×: ΔEab ^* is 1.0 or more

Claims (5)

C. I. Pigment Red 177 and a colorant solution obtained by dissolving a xanthene dye represented by the following general formula (1) in concentrated sulfuric acid, and water to mix the water with water to form a colored composition. Production method.
(In the general formula (1), R _{1 to} R ₄ each independently represent an alkyl group having 1 to 8 carbon atoms.)   The method for producing a coloring composition according to claim 1, wherein the coloring material solution is added to a large amount of the flowing water, and the coloring material solution and the water are mixed.   A colored composition produced by the method for producing a colored composition according to claim 1.   A coloring agent containing the coloring composition according to claim 3.   The colorant according to claim 4, which is used for producing a color filter.