JPH06336557A - Pigment composition and coating material - Google Patents

Abstract

PURPOSE:To obtain a pigment composition which is excellent in versatility, thus can be used as a dispersant for various pigments and easily gives a coating material having good pigment dispersion and excellent in flowability and coating film gloss, by using a specified compound together with a resin-base dispersant for pigment. CONSTITUTION:A pigment (A) is mixed with a salt (B) of N,N'-disubstituted diaminostilbenesulfonic acid and a resin-base dispersant (C) for pigment to give the objective composition. Examples of component A include a perylene pigment, a threne pigment and an anthraquinone pigment. Examples of component B include a metal salt and an ammonium salt which have a triazine ring as the substituent. An example of component C is an aminated resin-base dispersant for pigment. The composition is obtained by merely mixing the components or adding a solution containing the components B and C to an aqueous or organic solvent suspension of the pigment to deposit the components B and C on the surface of the pigment. The components B and C are usually used in amounts of 2-30 pts.wt. and 5-40 pts.wt., respectively, based on 100 pts.wt. component A.

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a pigment composition having a good pigment dispersibility, a fluidity and a coating gloss which are easily obtained, and a coating composition containing the pigment composition.

[0002]

2. Description of the Related Art Generally, when a pigment is dispersed in a non-aqueous medium such as paint or printing ink, strong energy is required because the pigment is fine, and the dispersion stability of the pigment is insufficient, and the pigment sometimes reaggregates. , The fluidity of the paint or printing ink is impaired, and the desired hue and gloss cannot be obtained in the coating film. Moreover, it is known that such a paint often has a high viscosity and causes various problems in the manufacturing operation. In addition to the dispersion stability of the pigment, the change in the hue may be caused by the change in the crystal structure of the pigment.

In the past, many proposals have been made to solve such problems. For example, German Patent Application Publication No. 2,500,509 (US Pat. No. 3,973)
3,981), German Patent Application Publication No. 3,10.
No. 6,906 (US Pat. No. 4,310,359), German Patent Application Publication No. 3,514,077 (US Pat. No. 4,664,714) and Japanese Patent Laid-Open No. Sho 5 (1999).
As described in JP-A 9-96175, there may be mentioned one in which a pigment derivative having the same skeleton as that of the pigment dispersed at the time of dispersing the pigment is added, or a pigment treated with these pigment derivatives is used. However, these are all insufficient in the pigment dispersion effect.

Further, as described in JP-A-52-150106, a dispersion using an uncolored N, N'-disubstituted diaminostilbene sulfonate has been proposed, which is also disclosed. The pigment dispersion effect is insufficient.

Therefore, as disclosed in Japanese Patent Laid-Open No. 62-295966, a proposal has been made to improve by using a pigment derivative having the same skeleton as the pigment to be dispersed and a urethane pigment dispersant. There is.

[0006]

However, Japanese Patent Laid-Open No. 62-62
In the method described in JP-A-295966, the pigment derivative must be changed every time the pigment is changed, and thus a large number of pigment derivatives are required, resulting in poor versatility for various pigments.
In addition, there is a problem that these derivatives are expensive due to manufacturing reasons.

[0007]

Therefore, the present inventors have
As a result of intensive studies to solve the above problems, when N, N′-disubstituted diaminostilbene sulfonate is used in combination with a resin-based pigment dispersant, it can be used as a dispersant for various pigments and is excellent in versatility. It has been found that a paint or ink having good pigment dispersibility and excellent fluidity and coating film gloss can be easily obtained because of high pigment dispersion effect, and thus the present invention has been completed.

That is, the present invention relates to a pigment (A), N,
N'-disubstituted diaminostilbene sulfonate (B)
And a resin-based pigment dispersant (C), and a coating composition comprising the pigment composition.

Examples of the pigment (A) used in the present invention include various organic and inorganic pigments commonly used in paints and printing inks, such as perylene pigments, anthraquinone pigments, slene pigments, and diene pigments. Ketopyrrolopyrrole pigment, quinacridone pigment, azo pigment, indigo pigment, copper phthalocyanine pigment, perinone pigment, quinophthalone pigment, dioxazine pigment, isoindolinone pigment, methine pigment, carbon black and those Examples thereof include pigment mixtures, and among them, perylene pigments, slene pigments, and anthraquinone pigments are preferable.

Examples of the N, N'-disubstituted diaminostilbene sulfonate (B) used in the present invention include N, N '
Examples thereof include metal salts and ammonium salts of N′-di-substituted diaminostilbene sulfonic acid (also referred to as ammonium salts including amine salts. The same applies hereinafter), among which N,
Aluminum salts, calcium salts, barium salts, strontium salts and substituted ammonium salts of N'-disubstituted diaminostilbene sulfonic acid are preferable, and substituted ammonium salts are particularly preferable. Further, those having a triazine ring as a substituent of N, N'-disubstituted diaminostilbenesulfonic acid are more preferable.

The N, N'-disubstituted diaminostilbene sulfonic acid metal salt (B), such as sodium N, N'-disubstituted diaminostilbene sulfonate, is prepared by converting N, N'-disubstituted diaminostilbene sulfonic acid into sodium hydroxide. It is usually obtained by reacting with. The metal salt other than the sodium salt is, for example, N, N′-disubstituted diaminostilbenesulfonic acid sodium salt dissolved in water heated to about 80 ° C., and the metal salt in the same amount as the sodium salt. In addition,
Stir at the same temperature for 1 hour, and further add pH 3-4 of this stirring solution.
It is easily obtained by adding the above metal salt until it becomes, and then cooling and filtering the resulting solid, washing with water, and drying.

Examples of the metal salt used here include aluminum salts such as aluminum chloride and aluminum nitrate, calcium salts such as calcium nitrate and calcium carbonate, barium salts such as barium chloride and barium nitrate, and strontium salts such as strontium chloride. To be Incidentally, these may be hydrates.

Further, the N, N'-di-substituted diaminostilbene sulfonic acid ammonium salt is prepared by, for example, adding a solution of N, N'-di-substituted diaminostilbene sulfonic acid sodium salt to N, N'-di-substituted diaminostilbene sulfonic acid sodium salt. The salt was dissolved in water heated to about 90 ° C., hot water in which an equivalent amount of ammonium salt to the sodium salt was dissolved was added, and the mixture was stirred at the same temperature for 30 minutes and cooled, and then the produced solid was filtered. Separately, washed and dried to easily obtain.

The ammonium salt used here is not particularly limited, but among them, a substituted ammonium salt,
Preferred are, for example, butylamine, stearylamine, cyclohexylamine, didodecylamine, 3-octadecylaminopropylamine and other tertiary amines neutralized with acids such as hydrochloric acid and acetic acid, and various quaternary ammonium salts. . Examples of the neutralized primary to tertiary amines with an acid include stearyl ammonium acetate and monobutylammonium chloride, and examples of the quaternary ammonium salt include cetyl-trimethylammonium bromide and didodecyldimethylammonium chloride. , Dioctadecyldimethylammonium chloride,
Benzyl dimethyl octadecyl ammonium chloride,
Examples thereof include N-cetylpyridinium chloride, N-cetylpiperidine chloride, N, N'-dimethyloctadecyl ammonium chloride and the like.

Further, N, N'-disubstituted diaminostilbene sulfonic acid having a triazine ring as a substituent,
Examples of the N'-disubstituted diaminostilbene sulfonate include 4,4'-bis- (4-anilino-6-methoxy-s-triazin-2-ylamino) stilbene-
2,2'-disulfonic acid metal salt or ammonium salt,
4,4'-bis- (4,6-dianilino-s-triazin-2-ylamino) stilbene-2,2'-disulfonic acid metal salt or ammonium salt, 4,4'-bis- (4
-P-toluidino-6-diethylamino-s-triazin-2-ylamino) stilbene-2,2'-disulfonic acid metal salt or ammonium salt, 4,4'-bis- (4
Examples thereof include metal salts and ammonium salts of -anilino-6-morpholino-s-triazin-2-ylamino) stilbene-2,2'-disulfonic acid.

As a typical example of the above N, N'-disubstituted diaminostilbene sulfonate, 4,4'-bis- (4
-Anilino-6-β-hydroxyethylamino-S-triazin-2-ylamino) -stilbene-2,2'-
Cetyltrimethylammonium disulfonate, 4,4 '
-Bis- (4-anilino-6-methylamino-S-triazin-2-ylamino) -stilbene-2,2'-cetyltrimethylammonium disulfonate, 4,4'-
Bis- (4-anilino-6-methoxy-S-triazin-2-ylamino) -stilbene-2,2'-cetyltrimethylammonium disulfonate, 4,4'-bis-
(4-anilino-6-β-hydroxyethylamino-S
-Triazin-2-ylamino) -stilbene-2,
2'-disulfonic acid didodecyl methyl ammonium,
4,4'-Bis- (4-anilino-6-β-hydroxyethylamino-S-triazin-2-ylamino) -stilbene-2,2'-disulfonic acid N, N'-dimethyloctadecyl ammonium, 4,4 '-Bis- (4-anilino-6-β-hydroxyethylamino-S-triazin-2-ylamino) -stilbene-2,2'-disulfonic acid dioctadecyldimethylammonium, 4,
Aluminum 4'-bis- (4-anilino-6-β-hydroxyethylamino-S-triazin-2-ylamino) -stilbene-2,2'-disulfonate, 4,4 '
-Bis- (4,6-dianilino-S-triazine-2-
Ilamino) -stilbene-2,2'-disulfonic acid aluminum, 4,4'-bis- (4-p-toluidine-
6-Diethylamino-S-triazin-2-ylamino) -stilbene-2,2'-disulfonate calcium, 4,4'-bis- (4-anilino-6-morpholino-S-triazin-2-ylamino) -stilbene −
Barium 2,2'-disulfonate, 4,4'-bis-
(4-anilino-6-β-hydroxyethylamino-S
-Triazin-2-ylamino) -stilbene-2,
Examples include 2'-strontium disulfonate.

The resin-based pigment dispersant (C) used in the present invention is not particularly limited as long as it has a pigment-dispersing effect, and is not particularly limited, but polyester-based pigment dispersants, acrylic resin-based pigment dispersants, and urethane resin-based pigment dispersants. Pigment dispersants are preferable, and dispersants having an amine value in the molecule are particularly preferable. The amine value of the dispersant having these amine values (value with respect to the resin solid content; the same applies hereinafter) is usually 10 to 120 mg · KOH / g, but it is 20 in consideration of the acid resistance of the coating film. ~ 50mg ・ KOH / g
Is preferred.

As a concrete example of the production of the polyester-based pigment dispersant, as described in JP-A-61-174939, a mixture of ε-caprolactone, lauric acid and tetrabutyl titanate is added under a nitrogen atmosphere. 17
The product was obtained by stirring for 20 hours at 0-180 ° C., and the mixture of this and dry polyethyleneimine was added under a nitrogen atmosphere at 1
The method of obtaining by stirring at 20 degreeC for 8 hours is mentioned.

The polyester-based pigment dispersant is, for example, Solspaase 3000, 6000, 900.
0, 13240, 17000, 24000 (all are I
(Manufactured by CI Corporation) and the like are commercially available.

Specific examples of the production of the acrylic resin-based pigment dispersant include xylene and n-butanol with isobornyl methacrylate and butyl acrylate as described in JP-A No. 1-164429. ,styrene,
Examples thereof include a method in which acrylonitrile, vinyl imidazole, and t-butyl perbenzoate are added and polymerized.

As the acrylic resin type pigment dispersant, for example, EFKA polymer-100, 400, 401.
(Manufactured by EFKA-Chemicals) and the like are commercially available. Specific examples of the production of the urethane resin-based pigment dispersant include vinyltoluene, isobutyl methacrylate, 2-ethylhexyl alcohol, hydroxyethyl methacrylate and polyethylene glycol, as described in European Patent Application Publication No. 3115757. A method for obtaining an acrylic-modified urethane resin-based pigment dispersant by reacting a polymer consisting of monomethacrylate with isophorone diisocyanate, and subsequently reacting with polyethylene glycol monomethacrylate and 1- (3-aminopropyl) imidazole, 60-166
No. 318, a polyester synthesized from ε-caprolactone and n-octanol is reacted with dismodular IL, followed by 1,12-diaminododecane and N, N-dimethyl-1,3-. Examples thereof include a method of obtaining a polyester-modified urethane resin-based pigment dispersant by reacting with propanediamine.

Examples of the polyester-modified urethane resin-based pigment dispersant include Disperbyk-160.
Series (Byk-Chemie), EFKA-4
0 series (made by EFKA-Chemicals), B
Olchigen SN-88 (manufactured by Borchers) and the like are commercially available.

The method for producing the pigment composition of the present invention includes:
It is not particularly limited, and includes, for example, powdered organic pigment (A), N, N'-disubstituted diaminostilbene sulfonate (B), resin-based pigment dispersant (C), and if necessary, A method of simply mixing the other components, or a suspension system of the organic pigment (A) with water or an organic solvent, the N, N′-di-substituted diaminostilbene sulfonate (B) and the resin-based pigment dispersant (C). Add the solution containing
Examples include a method of depositing the N, N′-di-substituted diaminostilbene sulfonate (B) and the resin-based pigment dispersant (C) on the pigment surface.

The amounts of N, N'-disubstituted diaminostilbene sulfonate (B) and resin-based pigment dispersant (C) used are:
Although not particularly limited, the N, N'-disubstituted diaminostilbene sulfonate (B) is usually 2 to 30 parts by weight, preferably 3 to 15 parts by weight, and the resin-based pigment is usually 100 parts by weight of the pigment (A). The dispersant (C) is usually 5 in terms of resin solid content.
-40 parts by weight, preferably 10-25 parts by weight.

Further, as a method for producing the coating material of the present invention,
For example, a method of adding and dispersing the pigment composition of the present invention in a non-aqueous resin solution, and further mixing a curing agent and an additive for paints, etc., if necessary, adding the pigment composition of the present invention to a solvent. And the like, and then a non-aqueous resin solution and, if necessary, a curing agent, a coating additive and the like are mixed.
In addition, as a method of adding the pigment composition of the present invention used here, a method of adding after mixing and dispersing the three components (A) to (C) in advance as described above is preferable.
A method of directly adding each component to the non-aqueous resin solution or solvent may be used.

The non-aqueous resin solution used here is not particularly limited, and for example, a solution of an alkyd resin, an acrylic resin, a urethane resin, an epoxy resin, a melamine resin or the like can be used.

The dispersing machine used for dispersing the pigment is
Bead grinders such as sand grinders, ball mills and attritors, roll mills, kneaders, dissolvers,
Examples include high speed mixers.

[0028]

EXAMPLES The present invention will be described in more detail below with reference to production examples, examples and comparative examples, but of course the gist of the present invention and its true meaning are not limited to these examples. In the examples, parts are parts by weight, and% is% by weight except for the gloss value.

Production Example 1 [Production of N, N'-disubstituted diaminostilbene sulfonate (B)] 4,4'-bis (4-anilino-6-β-hydroxyethylamino-s-triazine-2- ylamino) - an aqueous solution containing 500 parts 80 ° C. containing 10 parts of stilbene-2,2'-sodium disulfonate, aluminum chloride hexahydrate _{(AlCl 3 · 6H 2 O)} 10 parts was added, 1 at 80 ° C.
After stirring for an hour, aluminum chloride hexahydrate was further added until the pH of the stirred solution reached 3 to 4, and the resulting solid was filtered off, washed with water and dried to give 4,4'-bis (4 -Anilino-6-β-hydroxyethylamino-s
-Triazin-2-ylamino) -stilbene-2,
2'-Aluminium disulfonate was obtained.

Production Example 2 (same as above) 4,4'-bis (4-anilino-6-methylamino-s
-Triazin-2-ylamino) stilbene 2,2'-
20 ° C. aqueous solution containing 4 parts of sodium disulfonate 20
17 parts of a 25% aqueous solution of cetyltrimethylammonium bromide dissolved in hot water was added to the parts, and the mixture was stirred at 90 ° C. for 30 minutes and cooled, and then the produced solid was separated by filtration, washed and dried to give 4,4. ′ -Bis (4-anilino-6-methylamino-s-triazin-2-ylamino) stilbene-
Cetyltrimethylammonium 2,2'-disulfonate was obtained.

Example 1 Perylene pigment (CI Pigment Red 17
8) 9.5 parts, 4,4'-bis (4-anilino-6-β-hydroxyethylamino-s-triazin-2-ylamino) -stilbene-2,2'-disulfonic acid obtained in Preparation Example 1 0.5 part aluminum and Solspers 240
00 (polyester pigment dispersant manufactured by ICI, resin solid content: 100%, amine value: 42 mg · KOH / g)
5 parts were mixed with a Henschel mixer to obtain a pigment composition (1).

This pigment composition (1) was blended with a melamine alkyd resin for paint so that the pigment content was 11.4% (30 PHR) to prepare a melamine alkyd paint. Then, using a B type viscometer, the rotor rotation speed was 6 rpm and 6 rpm.
The viscosity of the paint was measured under the condition of 0 rpm, and T. I value (6r
The viscosity at pm / the viscosity at 60 rpm) was determined. Further, the gloss (60 °) of the coating film was measured.

The results are shown in Table 1. The paint had good pigment dispersibility, fluidity and coating gloss.

Comparative Example 1 Perylene pigment (CI Pigment Red 17
8) 9.5 parts and 4,4'-bis (4-anilino-6-β-hydroxyethylamino-s-triazin-2-ylamino) -stilbene-2,2'-disulfonic acid obtained in Preparation Example 1 0.5 parts of aluminum was mixed with a Henschel mixer to obtain a pigment composition (1 ').

A melamine alkyd coating was prepared in the same manner as in Example 1 except that this pigment composition (1 ') was used instead of the pigment composition (1). The I value and the gloss of the coating film were determined.

The results are shown in Table 1. This paint had poor pigment dispersibility and was inferior in fluidity and coating gloss.

Comparative Example 2 Perylene pigment (CI Pigment Red 17
8) 10.0 parts and 1.5 parts of Solspers 24000 are mixed by a Henschel mixer to prepare a pigment composition (2 ').
Got

An alkyd coating was prepared in the same manner as in Example 1 except that this pigment composition (2 ') was used in place of the pigment composition (1). The I value and the gloss of the coating film were determined.

The results are shown in Table 1. The paint had poor pigment dispersibility and was inferior in fluidity and coating gloss.

Example 2 Perylene pigment (CI Pigment Red 17
8) 9.5 parts, 4,4'-bis (4-anilino-6-methylamino-s-triazin-2-ylamino) stilbene 2,2'-disulfonic acid cetyltrimethylammonium salt obtained in Preparation Example 2 5 parts and EFKA polymer 40
1 (acrylic resin-based pigment dispersant manufactured by EFKA-Chemicals, resin solid content: 50%, amine value: 100 m
3.0 parts of g.KOH / g) was mixed with a Henschel mixer to obtain a pigment composition (2).

This pigment composition (2) is replaced with the pigment composition (1)
A melamine alkyd paint was prepared in the same manner as in Example 1 except that the melamine alkyd paint was used in place of the melamine alkyd. The I value and the gloss of the coating film were determined.

The results are shown in Table 1. The coating composition had good pigment dispersibility, fluidity and coating gloss.

Example 3 Perylene Pigment (CI Pigment Red 17
8) 9.5 parts, 4,4'-bis (4-anilino-6-methylamino-s-triazin-2-ylamino) stilbene 2,2'-disulfonic acid cetyltrimethylammonium salt obtained in Preparation Example 2 5 parts and Disperbyk-
4.5 parts of 160 (polyester-modified urethane resin-based pigment dispersant manufactured by Byk-Chemie, resin solid content: 29%, amine value: 38 mg · KOH / g) were mixed with a Henschel mixer to prepare a pigment composition (3). Got

This pigment composition (3) is replaced with the pigment composition (1)
A melamine alkyd paint was prepared in the same manner as in Example 1 except that the melamine alkyd paint was used in place of the melamine alkyd. The I value and the gloss of the coating film were determined.

The results are shown in Table 1. The paint had good pigment dispersibility, fluidity and coating gloss.

Example 4 Perylene Pigment (CI Pigment Red 17
8) 9.5 parts, 4,4'-bis (4-anilino-6-methylamino-s-triazin-2-ylamino) stilbene 2,2'-disulfonic acid cetyltrimethylammonium salt obtained in Preparation Example 2 5 parts and Sols Spars 2400
0 1.5 parts were mixed with a Henschel mixer to obtain a pigment composition (4).

This pigment composition (4) is replaced with the pigment composition (1)
A melamine alkyd paint was prepared in the same manner as in Example 1 except that the melamine alkyd paint was used in place of the melamine alkyd. The I value and the gloss of the coating film were determined.

The results are shown in Table 1. The paint had good pigment dispersibility, fluidity and coating gloss.

Example 5 Perylene pigment (CI Pigment Red 17
8) 9.5 parts, 4,4'-bis (4-anilino-6-methylamino-s-triazin-2-ylamino) stilbene 2,2'-disulfonic acid cetyltrimethylammonium salt obtained in Preparation Example 2 5 parts and EFKA polymer-40
0 (acrylic resin pigment dispersant manufactured by EFKA-Chemicals, resin solid content: 40%, amine value: 103 m)
3.75 parts of (g.KOH / g) was mixed with a Henschel mixer to obtain a pigment composition (5).

This pigment composition (5) is replaced with the pigment composition (1)
A melamine alkyd paint was prepared in the same manner as in Example 1 except that the melamine alkyd paint was used in place of the melamine alkyd. The I value and the gloss of the coating film were determined.

The results are shown in Table 1. The coating composition had good pigment dispersibility, fluidity and coating gloss.

Example 6 Perylene Pigment (CI Pigment Red 17
8) 9.5 parts, 4,4'-bis (4-anilino-6-methylamino-s-triazin-2-ylamino) stilbene 2,2'-disulfonic acid cetyltrimethylammonium salt obtained in Preparation Example 2 5 parts and Disperbyk-
166 (BYK-Chemie polyester modified urethane resin-based pigment dispersant, resin solid content: 30%, amine value: 67 mg.KOH / g) 5.0 parts were mixed with a Henschel mixer to prepare a pigment composition (6). Got

This pigment composition (6) is replaced with the pigment composition (1)
A melamine alkyd paint was prepared in the same manner as in Example 1 except that the melamine alkyd paint was used in place of the melamine alkyd. The I value and the gloss of the coating film were determined.

The results are shown in Table 1. The paint had good pigment dispersibility, fluidity and coating gloss.

[0055]

[Table 1]

Example 7 Anthraquinone pigment (C.I. Pigment Re
d 177) 9.5 parts, 4,4'-bis (4-anilino-6-methylamino-s-triazine-obtained in Preparation Example 2
2-ylamino) stilbene 0.5 parts of cetyltrimethylammonium 2,2'-disulfonate and Bolchi
genne SN-88 (polyester modified urethane resin-based pigment dispersant manufactured by Borchers, solid resin content: 25)
%, Amine value: 23 mg.KOH / g) 6.0 parts were mixed with a Henschel mixer to obtain a pigment composition (7).

This pigment composition (7) was added to an acrylic resin for paint so that the pigment content would be 5.6% (15 PHR) to prepare an acrylic paint. Then, using a B type viscometer, the viscosity of the coating material was measured under the conditions of a rotor rotation speed of 6 rpm and 60 rpm, and T.I. I value (viscosity at 6 rpm / 6
The viscosity at 0 rpm) was determined. Furthermore, the gloss of the coating film (60
) Was measured.

The results are shown in Table 2. The coating composition had good pigment dispersibility, fluidity and coating gloss.

Comparative Example 3 Anthraquinone type pigment (CI Pigment Re
d 177) and 4,4'-bis (4-anilino-6-methylamino-s-triazine-obtained in Production Example 2).
0.5 parts of 2-ylamino) stilbene 2,2′-cetyltrimethylammonium disulfonate was mixed by a Henschel mixer to obtain a pigment composition (3 ′).

An acrylic paint was prepared in the same manner as in Example 7 except that this pigment composition (3 ') was used in place of the pigment composition (7). The I value and the gloss of the coating film were determined.

The results are shown in Table 2. This paint had poor pigment dispersibility and was inferior in fluidity and coating gloss.

Comparative Example 4 Anthraquinone type pigment (CI Pigment Re
d 177) 10.0 parts and Bolchigenn SN
-88 6.0 parts were mixed with a Henschel mixer to obtain a pigment composition (4 ').

An acrylic paint was prepared in the same manner as in Example 7 except that this pigment composition (4 ') was used in place of the pigment composition (7). The I value and the gloss of the coating film were determined.

The results are shown in Table 2. This paint had poor pigment dispersibility and was inferior in fluidity and coating gloss.

Example 8 Slen-based pigment (C.I. Pigment Blue)
60) 9.5 parts, 4,4'-bis (4-
Anilino-6-methylamino-s-triazin-2-ylamino) stilbene 0.5 parts cetyltrimethylammonium 2,2'-disulfonate and EFKA polymer-4
3.75 parts of 00 was mixed with a Henschel mixer to obtain a pigment composition (8).

This pigment composition (8) is replaced with the pigment composition (7)
Acrylic paint was prepared in the same manner as in Example 7 except that it was used in place of No. The I value and the gloss of the coating film were determined.

The results are shown in Table 2. The paint had good pigment dispersibility, fluidity and coating gloss.

Comparative Example 5 Slen-based pigment (C.I. Pigment Blue)
60) 9.5 parts and 4,4'-bis (4-
0.5 part of anilino-6-methylamino-s-triazin-2-ylamino) stilbene 2,2′-cetyltrimethylammonium disulfonate was mixed by a Henschel mixer to obtain a pigment composition (5 ′).

An acrylic paint was prepared in the same manner as in Example 7 except that this pigment composition (5 ') was used in place of the pigment composition (7). The I value and the gloss of the coating film were determined.

The results are shown in Table 2. This paint had poor pigment dispersibility and was inferior in fluidity and coating gloss.

Comparative Example 6 Slene pigment (C.I. Pigment Blue)
60) 10.0 parts and EFKA polymer-400 3.75
Parts were mixed with a Henschel mixer to obtain a pigment composition (6 ').

An acrylic paint was prepared in the same manner as in Example 7 except that this pigment composition (6 ') was used in place of the pigment composition (7). The I value and the gloss of the coating film were determined.

The results are shown in Table 2. This paint had poor pigment dispersibility and was inferior in fluidity and coating gloss.

[0074]

[Table 2]

[0075]

The pigment composition of the present invention uses N, N'-disubstituted diaminostilbene sulfonate in combination with a resin-based pigment dispersant, and thus can be used as a dispersant for various pigments. It has excellent properties, has a high pigment dispersion effect, and easily obtains good paints and inks. Further, a coating material containing this pigment composition has good pigment dispersibility and is excellent in fluidity and coating gloss.

Claims (7)

[Claims] 1. A pigment composition comprising a pigment (A), an N, N′-disubstituted diaminostilbene sulfonate (B), and a resin-based pigment dispersant (C). 2. The N, N′-disubstituted diaminostilbene sulfonate (B) is selected from aluminum, calcium, barium, strontium and substituted ammonium salts of N, N′-disubstituted diaminostilbene sulfonate. The pigment composition according to claim 1, which is one or more salts selected from the group consisting of: 3. The pigment composition according to claim 1, wherein the N, N′-disubstituted diaminostilbenesulfonic acid salt (B) is a substituted ammonium salt of N, N′-disubstituted diaminostilbenesulfonic acid. 4. The pigment composition according to claim 1, wherein the N, N′-disubstituted diaminostilbene sulfonate (B) has a triazine ring as a substituent. 5. The pigment composition according to claim 1, wherein the resin-based dispersant (C) is a pigment dispersant having an amine value. 6. The pigment (A) is one or more kinds of organic pigments selected from the group consisting of perylene pigments, slene pigments and anthraquinone pigments.
The pigment composition according to item 1. 7. A paint comprising the pigment composition according to any one of claims 1 to 6.