JPH11302553A - Production of surface-treated pigment - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain the pigment having excellent dispersibility, transparency and brilliancy and useful as a colorant for coatings, etc. by simultaneously taking out the sulfuric acid solution of an organic pigment with a water-soluble salt of a resin acid into water. SOLUTION: This method for producing a surface-treated pigment comprises dissolving (A) an organic pigment such as a perylene. perinone-based compound pigment, a quinaquridone-based compound pigment or a phthalocyanine-based compound pigment in (B) sulfuric acid, simultaneously taking out the obtained solution (for example, a solution obtained by dissolving 2-10 pts.wt. of the component A in 100 pts.wt. of the component B having a concentration of >=95 wt.%) together with an aqueous solution of (C) a resin acid salt (for example, the reaction product of natural rosin, a modified rosin or a rosin-modified phenol with an alkali metal hydroxide) (for example, an aqueous solution of 0.5-3 pts.wt. of a resin acid salt in 100 pts.wt. of water) into (D) water to coat the surface of the deposited component A with the resin acid of the component C. The coating is preferably carried out by using the component C in an amount of 3-45 pts.wt. per 100 pts.wt. of the component A.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

The present invention relates to a method for producing a surface-treated pigment in which a pigment is surface-treated with a resin acid. More specifically, the present invention provides pigments having excellent suitability for coloring materials such as paints, plastics, printing inks, rubber, leather, textile printing, color filters, jet inks, and thermal transfer inks.

[0002]

2. Description of the Related Art In the field of color materials such as paints and inks, it is not possible to use pigments that have been subjected to surface treatment in order to impart appropriate properties such as dispersibility, transparency, fluidity, gloss, sharpness, and stability over time. General.

[0003] Conventionally, as this surface treatment agent, for example, “PIGMENT HANDBOOK” No. 3
Pp. 157-167 (issued in 1973), rosin, rosin derivatives, amines, pigment derivatives, and synthetic resins are disclosed. As a surface treatment method, rosin is dissolved in water as an alkali metal salt. A method in which this is added to an aqueous slurry of the pigment and then precipitated with sulfuric acid as an insoluble free acid or as a metal salt on the surface of the pigment, a rosin derivative, and in a synthetic resin, the aqueous dispersion of the pigment is used. A method of adding the compound to an aqueous slurry is disclosed.

In Japanese Patent Publication No. 58-47425, perylene-based compounds include perylene-3, 4,
A production method is disclosed in which 9,10-tetracarboxylic dianhydride is reacted with an amine in the presence of a resin acid to treat the resin acid during the synthesis of a pigment. JP-A-5-230390 discloses a production method in which rosin is used, emulsified and treated in an aqueous system.

As described above, these methods cannot perform a surface treatment at a fine level, and it has been impossible to obtain a surface-treated pigment having recently required dispersibility, transparency, and sharpness.

[0006]

The problem to be solved by the present invention is to coat resin acid at a finer level than before,
An object of the present invention is to provide a pigment having good dispersibility, transparency, and sharpness.

[0007]

The present inventors have conducted intensive studies to solve the above-mentioned problems. As a result, in a method for producing a surface-treated pigment, an organic pigment was dissolved in sulfuric acid, and the solution was dissolved in a resin acid. It is taken out in water at the same time as the water-soluble salt, the surface treatment is performed by coating the precipitated fine pigment surface with resin acid, and by separating the surface-treated pigment from the aqueous slurry, the dispersibility is better than before and the transparency is higher. The present inventors have found that a pigment having excellent properties and sharpness can be obtained, thereby completing the present invention.

The organic pigments used here include perylene / perinone compound pigments, quinacridone compound pigments, phthalocyanine compound pigments, anthraquinone compound pigments, phthalone compound pigments, dioxazine compound pigments, and isoindolinone compound pigments. In the case of one or more organic pigments selected from the group consisting of methine-azomethine-based compound pigments and diketopyrrolopyrrole-based compound pigments, the conventional case is more independent than when applied to the production of various azo-based compound pigments. The pigment precipitation step and the surface treatment step can be shortened to one step, which is more preferable in that the total number of production steps can be reduced. 3 parts by weight
In the range of from 45 to 45 parts by weight, the effect of improving the dispersibility and transparency is higher and preferable than the case where the surface treatment is performed only after the precipitation of the pigment, and as a result, the productivity per unit time is excellent, It was also found to be an economically superior method.

That is, the present invention provides the following inventions. (1) In a method for producing a surface-treated pigment in which an organic pigment is coated with a resin acid, the organic pigment is dissolved in sulfuric acid, and the solution is taken out in water simultaneously with a water-soluble liquid of the resin acid.
A method for producing a surface-treated pigment, which comprises coating the surface of a precipitated pigment with a resin acid.

(2) The organic pigment is a perylene / perinone compound pigment, quinacridone compound pigment, phthalocyanine compound pigment, anthraquinone compound pigment, phthalone compound pigment, dioxazine compound pigment, isoindolinone compound pigment, methine -The production method according to (1), which is one or more organic pigments selected from the group consisting of azomethine-based compound pigments and diketopyrrolopyrrole-based compound pigments;

(3) The proportion of the resin acid used for the surface treatment is 3 to 3 with respect to 100 parts by weight of the final organic pigment.
The production method according to (1) or (2), which is in a range of 0 parts by weight,

[0012]

DESCRIPTION OF THE PREFERRED EMBODIMENTS As the organic pigment which is not coated with a resin acid used in the production method of the present invention, any known and commonly used organic pigments can be mentioned, for example, perylene / perinone compound pigments, quinacridone type pigments. Compound pigment, phthalocyanine compound pigment, anthraquinone compound pigment,
Examples include phthalone compound pigments, dioxazine compound pigments, isoindolinone compound pigments, methine / azomethine compound pigments, diketopyrrolopyrrole compound pigments, insoluble azo compound pigments, and condensed azo compound pigments.

Above all, those other than azo compound pigments,
Specifically, perylene / perinone compound pigment, quinacridone compound pigment, phthalocyanine compound pigment, anthraquinone compound pigment, phthalone compound pigment, dioxazine compound pigment, isoindolinone compound pigment, methine / azomethine compound pigment, Diketopyrrolopyrrole-based compound pigments are preferred.

Regarding the method for producing the above-mentioned pigment, for example, “Industrial Organic Pigments (Industr
ial Organic Pigments) "(issued in 1993).

Specific examples of the organic pigment are as follows. Examples of perylene / perinone compound pigments include C.I. I. PigmentViolet 2
9, C.I. I. Pigment Red 123, 14
9, 178, 179, C.I. I. Pigment B
rack 31, 32, C.I. I. Pigment O
range 43, and the like.

The quinacridone compound pigments include, for example,. I. Pigment Violet 19, 4
2, C.I. I. Pigment Red 122, 20
2, 206, 207, 209, C.I. I. Pigm
ent Orange 48 and 49.

Examples of the phthalocyanine compound pigment include C.I. I. Pigment Blue 15, 15:
1, 15: 2, 15: 3, 15: 4, 15: 6, 16,
C. I. Pigment Green 7, and 36.

Examples of the anthraquinone compound pigment include C.I. I. Pigment Blue 60, C.I.
I. Pigment Yellow 24, 108,
C. I. Pigment Red 168, 177,
C. I. Pigment Orange 40 and the like.

As the phthalone compound pigment, for example,
C. I. Pigment Yellow 138 and the like.

Examples of the dioxazine compound pigment include C.I. I. Pigment Violet 23, 3
And the like.

The isoindolinone compound pigments include
For example, C.I. I. Pigment Yellow 10
9, 110, 173, C.I. I. Pigment O
and pigments such as range 61.

Examples of methine / azomethine compound pigments include C.I. I. Pigment Yellow 13
9, 185, C.I. I. Pigment Orange
66, C.I. I. Pigment Brown 38 and the like.

Examples of the diketopyrrolopyrrole compound pigment include C.I. I. Pigment Red 254 and 255.

Examples of the insoluble azo compound pigment include C.I. I. Pigment Yellow 1, 3,
12, 13, 14, 17, 55, 73, 74, 81, 83, 97, 130, 151,
152, 154, 156, 165, 166,
167, 170, 171, 172, 174,
175, 176, 180, 181, 188,
C. I. Pigment Orange 16, 3
6, 60, C.I. I. Pigment Red5, 2
2, 31, 31, 112, 146, 150, 17
1, 175, 176, 183, 185, 20
8, 213, C.I. I. PigmentViolet
43, 44, C.I. I. Pigment Blue 2
5, 26 and the like.

Examples of the condensed azo compound pigment include, for example,
C. I. Pigment Yellow 93, 9
4, 95, 128, 166, C.I. I. Pigme
ntOrange 31C. I. Pigment Re
d 144, 166, 214, 220, 22
1, 242, 248, 262, C.I. I. Pigm
ent Brown 41 and 42.

In the present invention, two or more of these organic pigments can be used in combination.

The present invention is practiced by simultaneously taking out a sulfuric acid solution of an organic pigment and an aqueous solution of a resinate into water.

The sulfuric acid solution of the organic pigment used in the present invention includes a sulfuric acid concentration satisfying a condition in which the organic pigment is dissolved,
The amount of the sulfuric acid and the amount of the organic pigment may be sufficient, but it is preferable that the amount of the organic pigment is 2 to 10 parts by weight with respect to 100 parts by weight of concentrated sulfuric acid of 95% by weight or more.

When the organic pigment is an organic pigment having a functional group capable of forming a salt with sulfuric acid, the organic pigment becomes a sulfate of the organic pigment and can be dissolved in a solution.

Next, in the present invention, an aqueous solution of a resinate is prepared. In the surface treatment of the organic pigment in the present invention, it is necessary to use an aqueous solution of resin acid as a water-soluble salt of resin acid. In the present invention, this aqueous solution is used.

As the water used in the present invention, any known water can be used, but it is preferable to use water containing no metal salts such as ion-exchanged water, distilled water, pure water and ultrapure water.

The resin acid used in the production method of the present invention includes, for example, natural rosins such as wood rosin, gum rosin, tall oil rosin, polymerized rosin, disproportionated (disproportionated) rosin, hydrogenated (hydrogenated) rosin Rosin derivatives such as modified rosin, rosin oxide, maleated rosin, rosin amine, lime rosin, rosin alkylene oxide adduct, rosin alkyd adduct, and rosin modified phenol. In the present invention, these resin acids are 2
More than one species may be used in combination.

The resinate can be obtained by reacting a resin acid with a base. As the base at this time,
Known and commonly used water-soluble bases may be mentioned, for example, alkali metal hydroxides such as sodium hydroxide and potassium hydroxide are typical.

The resinate aqueous solution can be obtained, for example, by dissolving a water-soluble base in water and adding a resin acid thereto.

The amount of the resin acid in the aqueous solution of the water-soluble salt of the resin acid is not particularly limited, but is usually 0.5 to 3.0 parts by weight per 100 parts by weight of water. ~ 2.5
It is preferably in the range of parts by weight.

The resin acid is reacted with a water-soluble base in hot water at usually 60 to 95 ° C., preferably 70 to 85 ° C. to form an aqueous solution of a water-soluble salt of the resin acid. The amount of the base is usually 0.1 to 100 parts by weight of water.
2.5 parts by weight, preferably in the range of 0.5 to 2.0 parts by weight.

The free sulfuric acid in the organic pigment sulfuric acid solution and the total water-soluble base including those contributing to the formation of the salt in the resinate aqueous solution are combined in an equivalent amount so that the former becomes excessive. It is preferable to use them.

The thus-obtained sulfuric acid solution of the organic pigment and the aqueous solution of the resinate are simultaneously taken out into water. As the water (take-out water) here, those described above are also preferably used. In addition, it is preferable that the amount of water taken out is much larger than the total amount of the organic pigment sulfuric acid solution and the aqueous solution of the resinate.

As a result of the removal, the solubility of the organic pigment dissolved in the sulfuric acid is sharply reduced by contact with the removal water, and the organic pigment is precipitated as fine particles as insoluble substances.
The resinate is returned from the state of the resinate to the resinic acid by contacting with sulfuric acid, and it is selectively and preferentially deposited on the surface of the finely divided organic pigment precipitated as an insoluble substance, The surface of the organic pigment fine particles is coated.

As a method for depositing an organic pigment, acid precipitation of resin acid, and surface treatment, the above-mentioned sulfuric acid solution and the aqueous solution of resin acid salt may be simultaneously taken out in stirring water. It is usually preferable to take out both of them at the same place and at a constant ratio at the same time and at a fixed ratio, rather than taking out the entire amount into the water to be taken out, from the viewpoint of making the pigment particle size distribution sharper.

The temperature of the water to be taken out is preferably low and preferably 10 ° C. or lower. In addition, line mixers such as ejectors, static mixers (manufactured by Noritake Co., Ltd.), sluzers (manufactured by Sumitomo Heavy Industries, Ltd.), honeycomb mixers, and imstat mixers (manufactured by Tatsumi Kogyo Co., Ltd.). The organic pigment can be precipitated and coated by surface treatment using an aspirator.

The ejector has a nozzle, a suction chamber, and a diffuser, so that a first fluid (main stream) can be introduced into the suction chamber through the nozzle, while a second fluid (suction) is provided. The liquid side) can also be introduced into the suction chamber from another inlet, and both fluids are combined and mixed in the suction chamber and discharged through the diffuser. The first fluid is ejected from the nozzle into the suction chamber, and then flows into the diffuser, whereby the second fluid is sucked into the suction chamber which has been reduced in pressure, and the first fluid can be mixed with the first fluid and discharged from the diffuser under pressure. . The ejector is sometimes called an injector (refer to the Chemical Engineering Dictionary above).

When this ejector is used, for example,
An aqueous solution of a water-soluble salt of resin acid is arranged in the main stream, and a sulfuric acid solution of an organic pigment is arranged on the suction side, so that the suction liquid comes into contact with the main stream, and at the same time, the pigment is precipitated and the surface treatment is performed. Here, the higher the speed of the ejection to the diffuser through the mainstream suction chamber, the more the suction chamber is depressurized, and there is no need to apply pressure from the suction liquid side to introduce the suction liquid into the suction chamber. Can be mixed. When an ejector is used in the method of the present invention, it is possible to perform mixing of the first fluid and the second third fluid only with a pump necessary for ejecting a mainstream first fluid from a nozzle, Compared to the case where a plurality of pumps are provided and mixed, the number of pumps can be reduced, the power energy consumption can be reduced, and the equipment can be made compact, which is preferable.

In this manner, the resin pigment is coated on the finely divided organic pigment. The resin acid is usually used in an amount of 3 to 45 parts by weight, generally about 100 parts by weight of the non-resin-acid-coated organic pigment, and almost the final organic pigment. The treatment is performed in the range of 3 to 30 parts by weight based on 100 parts by weight. However, in consideration of a decrease in the coloring power of the final organic pigment due to a decrease in the proportion of the coloring component in the final organic pigment with an increase in the resin acid treatment amount, the resin acid is added to 100 parts by weight of the non-resin acid-coated organic pigment. It is preferred that the treatment is carried out in the range of 3 to 30 parts by weight, generally in the range of 3 to 25 parts by weight based on 100 parts by weight of the final organic pigment.

The aqueous slurry of the organic pigment obtained by mixing the above-mentioned sulfuric acid solution, aqueous solution of resinate and water is subjected to filtration of the surface-treated pigment by a filter such as Nutsche or filter press. Next, it is washed with hot water or water. In some cases, it is preferable to peptize in water and wash.

As the filtration and washing and drying after washing, for example, batch or continuous drying in which the pigment is dehydrated and / or desolvated by heating at 30 to 120 ° C. by a heating source installed in a dryer, or the like. Examples of the dryer generally include a box dryer, a vacuum dryer, a band dryer, a spray dryer and the like.

The pulverization after drying is usually performed in order to pulverize the pigment when the pigment becomes a lump or the like as in the case of drying using a box type drier or a band drier. Examples thereof include pulverization with a mortar, hammer mill, disk mill, pin mill, jet mill, and the like. Further, it is preferable that coarse particles are removed from the obtained powder using a sieve or an airflow classifier.

The surface-treated pigment obtained by the production method of the present invention has good dispersibility as compared with conventional pigments, and is used for paints, plastics, printing inks, rubber, leather, textile printing, electronic toner, color filters, jet inks, and thermal transfer inks. It is suitable for coloring such as. In these applications, when the pigment obtained in the present invention is used as a coloring material for paint,
Particularly excellent transparency and sharpness are exhibited.

[0049]

EXAMPLES Hereinafter, using Examples, Reference Examples and Comparative Examples,
The present invention will be described in more detail. In the example below,
"Parts" and "%" represent "parts by weight" and "% by weight", respectively, unless otherwise specified.

Example 1 A beaker containing 500 parts of 95% sulfuric acid was charged with C.I. I. Pigment Red179
(Hereinafter abbreviated as Red179).
The mixture was gradually added with stirring to dissolve as a sulfate. After stirring for 60 minutes, this was used as a sulfuric acid solution of Red179 pigment.

Further, 1.2 parts of sodium hydroxide was added at 80 ° C.
After stirring and dissolving in 600 parts of water, 3 parts of tall oil rosin was added and dissolved by stirring to prepare a rosin aqueous solution, which was used as a surface treatment solution.

On the other hand, 5000 parts of water at 5 ° C. was charged into a beaker and stirred. Thereafter, the sulfuric acid solution of the above-mentioned pigment and the above-mentioned surface treatment solution were gradually dropped into the same water at a constant ratio at the same place, and the precipitation of the pigment, the acid precipitation of rosin, and the rosin treatment on the surface of the pigment were simultaneously performed.

After completion of the dropwise addition, the mixture was stirred for 60 minutes, and then filtered and washed with water. After washing with water to some extent, the mixture was peptized in 3000 parts of water to wash the pigment. The slurry was again filtered, washed with water, washed with water until the filtrate became neutral, dried, and powdered to obtain 12.4 parts of a surface treated pigment of Red179.

(Comparative Example 1) An experiment was performed without dropping the surface treatment solution of Example 1. As a result, 9.6 parts of an unsurface-treated pigment of Red 179 was obtained.

(Comparative Example 2) In the same manner as in Example 1, the surface treatment solution was not dropped, and the Re
A 10% aqueous solution of tall oil rosin sodium was added to an aqueous slurry at 80 ° C. in which 8 parts of the d179 pigment, in terms of a dry product, was dispersed in 300 parts of water, and the mixture was stirred for 60 minutes.
7 and rosin is acid-precipitated to perform surface treatment.
179 surface-treated pigments (10.0 parts) were obtained.

Comparative Example 3 Perylene was added to 500 parts of water.
3,4,9,10-tetracarboxylic dianhydride was added to 19.
6 parts, 0.6 part of 95% sulfuric acid and 31.37 parts of a 40% aqueous solution of methylamine (manufactured by Tokyo Chemical Industry Co., Ltd.) were charged, and stirring was continued at 0 to 5 ° C. for 1 hour. Then 1
58.8 parts of a 0% tall oil rosin sodium aqueous solution was added, the temperature was raised to 95 ° C., and stirring was continued for 3 hours. afterwards,
The mixture was cooled and maintained at 50 ° C., the pH was adjusted to 5.8, and rosin was acid-precipitated to perform a surface treatment, thereby obtaining 24.5 parts of a surface-treated pigment of Red179.

(Example 2) The surface treatment solution of Example 1
02.1 parts were weighed, and the experiment was conducted while changing the amount of rosin treatment for the pigment. As a result, 10.7 parts of a surface-treated pigment of Red 179 was obtained.

(Example 3) The surface treatment solution of Example 1
An experiment was conducted by weighing out 22.8 parts and changing the amount of rosin treatment for the pigment. As a result, 11.0 parts of a surface-treated pigment of Red 179 was obtained.

(Example 4) The surface treatment solution of Example 1
03.5 parts were weighed, and the experiment was performed while changing the amount of rosin treatment for the pigment. As a result, 11.9 parts of a surface-treated pigment of Red 179 was obtained.

(Example 5) The sulfuric acid solution of Red179 pigment in Example 1 was changed to a solution in which 25 parts of Red179 pigment was dissolved in 95% sulfuric acid. An experiment was performed. As a result, Red1
30.9 parts of 79 surface-treated pigments were obtained.

(Example 6) The amount of water taken out in Example 1 was 2
The experiment was performed with 500 parts. As a result, Red17
12.3 parts of 9 pigments were obtained.

Example 7 An experiment was conducted by changing the take-out method of Example 1 to an ejector. That is, a sulfuric acid solution of Red 179 was disposed on the mainstream liquid side, and a surface treatment solution was disposed on the suction liquid side. At the contact portion of the two liquids, pigment precipitation, rosin acid precipitation, and rosin treatment on the pigment surface were performed. As a result, R
12.3 parts of ed179 pigment were obtained.

Example 8 A beaker charged with 500 parts of 95% sulfuric acid was charged with C.I. I. Pigment Blue 60
Coarse pigment (MG BULE k-RS; manufactured by Mitsui BASF Dyeing Co., Ltd .; hereinafter abbreviated as Blue 60) 50
The portion was gradually added and dissolved while stirring. After stirring for 60 minutes, this was used as a sulfuric acid solution of indanthrone blue pigment.

After dissolving 12 parts of sodium hydroxide in 4000 parts of water at 80 ° C., 60 parts of hydrogenated rosin was added and dissolved by stirring to prepare a hydrogenated rosin sodium aqueous solution.

This aqueous solution of hydrogenated rosin sodium was mixed with 500
A part of the solution was weighed to obtain a surface treatment solution. On the other hand, 5000 parts of 5 ° C. water was charged into a beaker and stirred. Thereafter, a sulfuric acid solution of the pigment and a surface treatment solution were gradually dropped into the same water at a fixed ratio at the same location, and the precipitation of the pigment, the acid precipitation of rosin, and the rosin treatment on the pigment surface were simultaneously performed.

After completion of the dropwise addition, the mixture was stirred for 60 minutes, and then filtered and washed with water. After washing with water to some extent, the mixture was peptized in 3000 parts of water to wash the pigment. The slurry was again filtered, washed with water, washed with water until the filtrate became neutral, dried, and powdered to obtain 55.2 parts of a surface treated pigment of Blue 60.

(Comparative Example 4) In Example 8, Bl at the stage when the water washing was completed was performed so that the surface treatment solution was not dropped.
To a 80 ° C. aqueous slurry obtained by dispersing 45 parts of ue60 pigment in terms of a dry product in 1000 parts of water, 450 parts of the aqueous solution of hydrogenated rosin sodium prepared in Example 8 was added, and after stirring for 60 minutes, the pH was adjusted to 5.5. The surface treatment was carried out by acid precipitation of rosin to obtain 50.6 parts of a surface treated pigment of Blue 60.

(Embodiment 9) Blue 60 of Embodiment 8 was replaced by C.I. I. Pigment Blue 15 (hereinafter referred to as Blue)
Abbreviated as e15. ), And the experiment was conducted by further changing the hydrogenated rosin to the disproportionated rosin. As a result, Blue 15
56.1 parts of the surface-treated pigment was obtained.

(Comparative Example 5) Blue 60 of Comparative Example 4 was replaced with C.I. I. Pigment Blue 15 (hereinafter referred to as Blue)
Abbreviated as e15. ), The experiment was conducted by further changing the hydrogenated rosin to the disproportionated rosin. As a result, Blue 15
50.3 parts of the surface-treated pigment was obtained.

(Example 10) The Red179 pigment of Example 1 was replaced with C.I. I. Pigment Red 122 (hereinafter referred to as R
Abbreviated as ed122. ) Experiments were performed with pigments.
As a result, 12.2 parts of a surface-treated pigment of Red 122 was obtained.

(Test Example 1) << Comparison Test of Saturation, Coloring Power and Transparency with Melamine Alkyd Paint >>
6. Red179 pigments obtained in Comparative Examples 1 and 2, respectively.
0 g, Amirac No. 16.0 g of 1026 Clear (manufactured by Kansai Paint Co., Ltd.) and baking thinner No. 3
(Manufactured by Dojosha) 10.0 g and 3 mmφ glass beads 80 g
Was placed in a polyethylene bottle having a capacity of 100 ml, and dispersed with a paint conditioner (manufactured by Toyo Seiki Co., Ltd.) for 2 hours. 1026 Clear 5
Add 0.0g and add 1 more with paint conditioner
Dispersion was performed for 0 minutes to obtain melamine alkyd primary color paints.

Each of 6.0 g of the obtained primary color paint and Amirac No. Put 1531 white (manufactured by Kansai Paint Co., Ltd.) 10.0 g in a polyethylene cup,
The melamine alkyd light-colored paint was obtained by mixing uniformly.

The obtained melamine alkyd primary color paint is applied and spread on an art paper with a 10 mil (254 μm) applicator, and the obtained melamine alkyd light color paint is applied on an art paper with 6 mil (1 mil).
(52 μm) and spread for 1 minute, and then baked in a dryer at 140 ° C. for 20 minutes to dry.

The color of these coatings was measured using an ACS-1400STC spectrophotometer (manufactured by ACS, USA).
The chroma C * and the coloring power of the primary color paints of the nine pigments were compared.

[0075]

[Table 1]

The Red 179 pigments obtained in Examples 1 to 7 have higher definition (higher chroma) and higher coloring power than Comparative Example 2, and therefore, the formulation of the present invention is more effective than performing rosin by post-treatment. Was confirmed. In addition, it has higher clarity (higher chroma) and higher coloring power than Comparative Example 3, and it was confirmed that a finer surface-treated pigment could be produced than when rosin treatment was performed during crude synthesis. The comparison between Example 1 and Comparative Example 1 was based on the effect of the presence or absence of the rosin treatment, and it was confirmed that when the rosin treatment was not performed, there was coloring power but the sharpness was reduced.

In the comparison of Examples 1 to 4, as the rosin treatment amount increases, the image becomes sharper and the coloring power decreases.
However, since the rate of decrease in coloring power is smaller than the rate of increase in rosin processing amount, it can be seen that rosin was effectively treated at the time of removal.

Further, Embodiments 1, 6, and 7
It was confirmed from the comparison that almost the same results were obtained regardless of the amount of water taken out and the method of taking out water.

Further, it was confirmed by visual judgment that Red 179 obtained in Examples 1 to 7 was a pigment having higher transparency than Comparative Examples 1 to 3.

The surface-treated pigments of Examples 8 to 10 were confirmed to be pigments having higher chroma and transparency than those produced by the corresponding prior art.

(Test Example 2) << Comparison test of metallic feeling with acrylic melamine paint >> (Adjustment of primary color enamel) Red 179 pigment obtained in Example 1, Comparative Example 2 and Comparative Example 3, 15.0 g each,
30.0 g of Acridic 47-712 (manufactured by Dainippon Ink and Chemicals, Inc.), 40.0 g of a mixed solvent (weight ratio of xylene / n-butanol = 75/25), and 3 mm
150 g of φ glass beads is placed in a 250 ml polyethylene bottle and dispersed with a paint conditioner (manufactured by Toyo Seiki Co., Ltd.) for 2 hours, after which 90.0 g of Acridic 47-712 and Super Beckamine L-117- are dispersed. 60 (manufactured by Dainippon Ink and Chemicals, Inc.)
25.0 g was added, and the mixture was further dispersed with a paint conditioner (manufactured by Toyo Seiki Co., Ltd.) for 10 minutes to obtain an acrylic melamine primary color enamel.

(Adjustment of Aluminum Enamel) Alpaste 7
620NS (Toyo Aluminum Co., Ltd.) 40.5g
324.0 g of Acrydic 47-712 (manufactured by Dainippon Ink and Chemicals, Inc.) and Super Beckamine L
-117-60 (manufactured by Dojo Co.) 67.5 g, mixed solvent (xylene / n-butanol weight ratio = 75/25) 1
And 08.0 g were mixed in a stainless steel cup to obtain an aluminum enamel.

(Coating of acrylic melamine paint) 35.0 g of each of the acrylic melamine primary color enamels obtained above.
And 35.0 g of aluminum enamel and a mixed solvent (weight ratio of Solvesso # 100 / xylene / ethyl acetate / n-butanol = 40/30/20/10) were mixed in a plastic cup, and each mixed with 5 : 5 An aluminum acrylic melamine paint enamel was obtained.

Each of the obtained 5: 5 aluminum acrylic melamine paint enamels is applied to a painting robot (Softboy S).
B41-110R-0GA1; manufactured by Takubo Engineering Co., Ltd.) and applied to a 70 × 150 mm intermediate coated water-sharpened aluminum plate surface so that the dried coating film has a thickness of about 20 μm. 59.6% of Dainippon Ink and Chemicals, 21.3% of Super Beckamine L-117-60 (manufactured by the same company), Solvesso # 100; 17.2%, and n-butanol;
After applying a clear paint composed of 1.9% by a painting robot so that the dried film has a thickness of about 25 μm,
Leave for 1 day, bake in a dryer at 140 ° C for 23 minutes,
After drying, each test sample plate was obtained.

The color of these coatings was measured using an ACS-1400STC spectrophotometer (manufactured by ACS, USA).
The chromas C * of the nine pigments were compared.

[0086]

[Table 2]

From the above results, the Re obtained in Example 1 was obtained.
It was confirmed that the d179 pigment had higher definition (higher chroma) than Comparative Example 2 and Comparative Example 3 even in metallic coating with an acrylic melamine paint, and further had a metallic feeling. Therefore, it can be said that the pigment has higher definition and better metallic feeling than the surface-treated pigment produced by the corresponding conventional technique. In addition, it was confirmed that the surface-treated pigments of Examples 2 to 10 also had higher sharpness and better metallic feeling than those produced by the corresponding conventional technology.

(Test Example 3) << Evaluation Method of Color Filter >> Blue 6 obtained in Example 8 and Comparative Example 4 was placed in a glass container.
2.0 g each of the No. 0 pigment, the Blue 15 pigment obtained in Example 9 and Comparative Example 5, 4.0 g of an ultraviolet-curable acrylic resin (Unidick S5-122: manufactured by Dainippon Ink and Chemicals, Inc.), and 2- Butoxy-1-propanol 9
4.0 g and 300 g of 0.4 mm zirconia beads were added, and dispersed for 2 hours by a paint conditioner (manufactured by Toyo Seiki Co., Ltd.) to prepare a coating solution.

The obtained coating solution was applied to a spin coater (1H-
Glass plate (705) using 3D type: Mikasa Corporation
9: Corning Co.) to obtain a colored glass plate that can be used as an optical element. The application conditions were 200 rpm for 10 seconds, and then 2000 rpm for 30 seconds.

The transmittance of these coatings at a wavelength of 450 nm was measured using a SPECTRAFLASH 500 spectrophotometer (manufactured by Data Color International, USA).

[0091]

[Table 3]

From the above results, Bl obtained in Example 8 was obtained.
The blue60 pigment obtained in Example 9 was compared with the Blue60 pigment obtained in Comparative Example 4 for the blue60 pigment obtained in Comparative Example 4.
It was confirmed that the transmittance was higher than that of the Blue 15 pigment obtained in Step 1. Therefore, it was confirmed that it had better transparency than the corresponding one manufactured by the related art.

The surface-treated pigments obtained in Examples 1 to 7 and 10 were also compared with those produced by the corresponding prior art.
It was confirmed that the pigment was transparent.

[0094]

According to the process for producing a surface-treated pigment of the present invention, the surface is coated with a resin acid at the same time as the dissolved organic pigment is precipitated in the form of fine particles.
A resin acid-coated organic pigment is easily obtained, which has the advantages of better dispersibility, transparency, and sharpness than before.

──────────────────────────────────────────────────続 き Continued on the front page (51) Int.Cl. ⁶ Identification code FI C09B 67/20 C09B 67/20 K

Claims (3)

[Claims] In a method for producing a surface-treated pigment in which an organic pigment is coated with a resin acid, the organic pigment is dissolved in sulfuric acid, and the solution is taken out into water simultaneously with an aqueous solution of a resin acid salt, whereby the precipitated pigment surface is removed. A method for producing a surface-treated pigment, which comprises coating with a resin acid. 2. An organic pigment comprising a perylene / perinone compound pigment, a quinacridone compound pigment, a phthalocyanine compound pigment, an anthraquinone compound pigment, a phthalone compound pigment, a dioxazine compound pigment, an isoindolinone compound pigment, methine. Azomethine compound pigments,
The method according to claim 1, wherein the organic pigment is at least one organic pigment selected from the group consisting of diketopyrrolopyrrole-based compound pigments. 3. The use ratio of the resin acid used for the surface treatment is 3 parts per 100 parts by weight of the non-resin acid-coated organic pigment.
The method according to claim 1 or 2, wherein the amount is in the range of -45 parts by weight.