JPH10245501A - Pigment composition and preparation thereof - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a composition which can impact, to a vehicle, good resistance to coagulation and to growth of a crystal, good stability and food flowability of a disperse system based on the vehicle, and also can be used for producing a coating film having excellent clearness and transparency by subjecting to a mechanical kneading a mixture of C.I. Pigment Red 177 with a specific compound having an anthraquinone skeleton in the presence of a water-soluble inorganic salt, thereby adjusting the specific surface area of a pigment to a value in a specific range. SOLUTION: This pigment composition is prepared by a method comprising subjecting to a mechanical kneading a mixture of C.I. Pigment Red 177 having formula I with a compound having formula II, [wherein X represents phthalimidomethyl group, a group having formula III (wherein Y is a group of -CH2 NH-, -SO2 NH- or the like, R<5-6> is H, a 1-18C alkyl and m is 0 to 6), and a group having formula IV (wherein Z is -NH- or Y and R<1-2> is OH, an alkoxy, phthalimidomethylamino or the like); and p is 1 to 8], wherein the kneading is conducted in the presence of a water-soluble inorganic salt (for example, sodium chloride) or a combination of the salt and a solvent such as ethylene glycol, thereby adjusting the specific surface area of a pigment to a value in the range of 50 to 150m<2> /g by minute control of operation.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention is excellent in suitability for use when dispersed in a vehicle or the like, particularly excellent in non-aggregation, crystal stability and fluidity, and excellent in sharpness and transparency when formed into a coating film. C. I. The present invention relates to a method for producing a pigment composition containing Pigment Red 177, the pigment composition obtained by the method, and a colorant composition comprising the pigment composition and a vehicle.

[0002]

2. Description of the Related Art I. Pigment Red 177 (4,
4'-Diamino-1,1'-dianthraquinonyl) is a practically useful red pigment having a vivid color tone and high coloring power. However, when dispersed in vehicles such as offset inks, gravure inks and paints, particularly non-aqueous vehicles, it is difficult to obtain a stable dispersion, and various dispersions that have a significant effect on the production work and the value of the obtained product. Problems often occur. For example, C.I. I. Pigment Red 1
Dispersions containing 77 often exhibit high viscosities, which not only makes it difficult to remove and transport the product from the disperser, but also worse, causes gelling during storage and may make it difficult to use. .

[0003] When different kinds of pigments are mixed and used, color unevenness and a marked decrease in coloring power may occur in a developed product due to phenomena such as color separation and sedimentation due to aggregation. Further, with respect to the surface of the coated film of the colored product, a state such as a decrease in gloss or poor leveling may occur. In non-aqueous vehicles such as offset inks, gravure inks and paints, C.I. I. Since the pigment particles of Pigment Red 177 change their size and form and shift to a stable state, the commercial value may be impaired due to a marked change in hue, a decrease in coloring power, generation of coarse particles, and the like in the developed product. .

In order to solve these problems, many proposals have been made mainly on copper phthalocyanine pigments and quinacridone pigments. The contents can be roughly classified into the following two when classified according to the technical method. A first method is disclosed in US Pat. No. 3,370,971 and US Pat.
As disclosed in JP-A-511, a colorless compound such as silicon oxide, aluminum oxide and tertiary butyl benzoic acid coats the surface of pigment particles. The second method is disclosed in JP-B-41-2466 and US Pat.
As represented by 61865, a method of mixing a compound obtained by introducing a substituent such as a sulfone group, a sulfonamide group, an aminomethyl group or a phthalimidomethyl group into a side chain using an organic pigment as a parent skeleton. .

[0005] The second method has a remarkable effect on the non-aggregation property and crystal stability of the pigment in the non-aqueous vehicle as compared with the first method, and is judged from the easiness of production of the pigment composition. This is a very advantageous method. JP-A-63-1
No. 72772 discloses, in particular, C.I. I. Pigment Red 1
A second method of mixing the sulfonated derivative of No. 77 has been proposed, but the pigment composition obtained by this method is not sufficiently satisfactory in quality.

In recent years, as a new application development of a pigment dispersion,
Application to a pigment dispersion for a color filter of a liquid crystal display, a pigment dispersion for an ink-jet used in an ink-jet printer, and the like has been advanced. These are intended to use the pigment dispersion for applications to more sophisticated devices, etc., in order to obtain a pigment dispersion that meets the required physical properties,
In particular, a pigment that is fine and stably dispersed is required.

For use as a pigment dispersion for these new uses, C.I. I. The pigment composition containing Pigment Red 177 is not sufficient in quality, and cannot satisfy required physical properties.

[0008]

The present invention relates to C.I. I. Pigment Red 177 contains a pigment composition having a specific surface area of 50 to 150 m ^2.
/ G of finely and uniformly sized pigment composition, and has good agglomeration resistance and crystal resistance against a wide range of non-aqueous and aqueous vehicles. An object of the present invention is to provide a method for producing a pigment composition which gives growth properties and stability and fluidity of a dispersion, and is excellent in sharpness and transparency when formed into a coating film. Furthermore, the present invention has excellent suitability for applications such as offset inks, gravure inks, paints, colorants for plastics, aqueous colors, textile printing, toning agents, color toners, pigment dispersions for color filters, pigment dispersions for inkjets, and the like. It is intended to provide a pigment composition and a colorant composition comprising the pigment composition and a vehicle.

[0009]

Means for Solving the Problems The present invention provides a compound represented by the following general formula [1]:

[0010]

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Represented by C.I. I. Pigment Red 1
77 and the following general formula [2] General formula [2]

[0012]

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(Wherein X represents a phthalimidomethyl group which may have a substituent, a substituent represented by the following general formula [3] or a substituent represented by the following general formula [4]; Is 1
Represents an integer of ８8. ), A mixture with the compound represented by
The pigment particles are mechanically kneaded in the presence of a water-soluble inorganic salt or a water-soluble inorganic salt and a solvent so that the pigment particles have a specific surface area of 50 to 1
A method for producing a pigment composition, which comprises finely regulating the particle size to 50 m ² / g. General formula [3]

[0014]

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(Where Y is -CH ₂ NH-, -SO ₂ N
_{H -, - CH 2 NHCOCH 2} NH -, - CONH-,
_{-CONHC 6 H 4 CONH -, -} CONHC 6 H 4 NH
_{-, - SO 2 -, -} CH 2 NHCOCH 2 -, - CO-
R ⁵ and R ⁶ each independently represent a hydrogen atom or a carbon atom having 1 to 5 carbon atoms which may have a substituent.
18 alkyl groups, an aryl group which may have a substituent,
R ⁵ and R ^{6 each} may further contain a nitrogen atom or an oxygen atom, represent a 5- or 6-membered heterocyclic ring which may have an alkyl group having 5 or less carbon atoms as a substituent, and m represents 0 to 6
Represents an integer. ) General formula [4]

[0016]

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(Where Z is —NH—, —CH ₂ NH—,
_{-SO 2 NH -, - CH 2} NHCOCH 2 NH -, - C
_{ONHC 6 H 4 CONH -, -} CONHC 6 H 4 NH-,
_{-CONH -, - SO 2 -,} - CH 2 NHCOCH 2
-, - represents a divalent bonding group selected from CO-, R ^1,
R ² independently represents a hydroxyl group, an alkoxy group which may have a substituent, a phthalimidomethylamino group which may have a substituent, or —NH (CH ₂ ) _n NR ³ R ⁴ (R
³ and R ⁴ each independently represent a hydrogen atom, an alkyl group having 1 to 18 carbon atoms which may have a substituent, an aryl group which may have a substituent, and further nitrogen represented by R ³ and R ⁴ Represents a 5- or 6-membered heterocyclic ring which may contain an atom or an oxygen atom and may have an alkyl group having 5 or less carbon atoms as a substituent. ), N represents an integer of 1 to 6. )

[0018]

DESCRIPTION OF THE PREFERRED EMBODIMENTS In the present invention, C.I. I. The compound represented by the general formula [2], which is used as a mixture with Pigment Red 177, is produced by introducing a substituent X into a parent anthraquinone skeleton. As a method for introducing the substituent X into the anthraquinone skeleton of the base, a phthalimidomethyl group which may have a substituent may be a known method of reacting with hydroxymethylphthalimide in sulfuric acid, for example, Japanese Patent Publication No. 17171/1988. It can be introduced by the methods described.

Introduction of a substituent having a structure of the general formula [3]
As the method, the parent anthraquinone was obtained by a known method.
-SO in the skeleton_TwoCl, -COCl, -CH_TwoCl,-
CH _TwoNHCOCH_TwoCompounds having substituents such as Cl introduced
, And this compound and H _TwoN (CH_Two)_mNR^FiveR
⁶Or HNR^FiveR⁶(R^Five, R⁶Has the same meaning as above
Represent. Example 1) reacting with an amine component having the structure of
For example, the method described in JP-B-63-17101 is used.
More can be introduced.

As a method for introducing a substituent having the structure of the general formula [4], a reaction between an amino group or a substituent having an amino group in a parent anthraquinone skeleton and cyanuric chloride, or a halogen in a parent anthraquinone skeleton may be used. _{group, -SO 2 Cl, -COCl, -CH} 2 Cl, -C
First, a triazine skeleton is introduced by reacting a substituent such as H ₂ NHCOCH ₂ Cl with melamine or another compound having a triazine skeleton, and then halogen groups, hydroxyl groups, amino groups, and the like remaining in the triazine skeleton are replaced with HN (CH ₂ ). _n
It can be introduced by reacting with an amine component having the structure of NR ³ R ⁴ (n, R ³ and R ⁴ have the same meaning as described above), alcohols, and hydroxymethylphthalimide.

In the present invention, C.I. I. Examples of the phthalimidomethyl group which may have a substituent in the compound represented by the general formula [2] used by mixing with Pigment Red 177 include phthalimidomethyl group, chlorophthalimidomethyl group, dichlorophthalimidomethyl Groups, methylphthalimidomethyl group, dimethylphthalimidomethyl group, nitrophthalimidomethyl group, t-butylphthalimidomethyl group, and the like, but are not limited thereto.

Examples of the substituent of the alkyl group having 1 to 18 carbon atoms which may have a substituent and the aryl group which may have a substituent in the compound represented by the general formula [3] of the present invention Examples include, but are not limited to, a hydroxyl group, a halogen atom, a nitro group, an amino group, a carboxylic acid group, and a sulfonic acid group.

Examples of the aryl group in the compound represented by the general formula [3] of the present invention include a benzene ring residue, a naphthalene ring residue and a nitrogen-containing heterocyclic residue, but are not limited thereto. It is not something to be done.

Examples of the substituent of the optionally substituted alkoxy group and the optionally substituted phthalimidomethylamino group in the compound represented by the general formula [4] of the present invention include a hydroxyl group. , A halogen atom, a nitro group, an amino group, a carboxylic acid group, a sulfonic acid group, and the like, but are not limited thereto.

In the general formula [3] or the general formula [4], -N
Examples of the amine residue represented by R ³ R ⁴ or -NR ⁵ R ⁶ is a methyl group, an ethylamino group, propylamino group, isopropylamino group, n- butylamino group, isobutylamino group, n- Amylamino group, isoamylamino group, n-hexylamino group, octylamino group, 2-ethylhexylamino group, decylamino group, dodecylamino group, stearylamino group, dimethylamino group, diethylamino group, di-n-butylamino group, diisobutyl Amino group, N-methylhexylamino group, di-
n-octylamino group, di- (2-ethylhexyl) amino group, 2-hydroxymethylaminoethanol group, diethanolamino group, 3-aminopropanol group, 2-
Aminopropanol group, 3-methoxypropylamino group, 3-ethoxypropylamino group, 3-propoxypropylamino group, 3-butoxypropylamino group, 3-
(2-ethylhexyloxy) propylamino group, 3-lauryloxypropylamino group, piperidinyl group, 2-pipecolinyl group, 4-pipecolinyl group, 2,4-lupetidinyl group, 2,6-lupetidinyl group, 3-piperidinemethanol Group, N-aminopiperidinyl group, N-amino-4
-Pipecolinyl group, 2-piperidineethanol group, pyrrolidinyl group, 3-hydroxypyrrolidinyl group, N-methylhomopiperidinyl group, N-methylpiperazinyl group, 1
-Amino-4-cyclopentylpiperazinyl group, 1-cyclopentylpiperazinyl group, morpholinyl group, thiomorphonyl group, dimethylaminoethylamino group, ethylaminoethylamino group, diethylaminoethylamino group, methylaminopropylamino group, dimethylamino Propylamino group, diethylaminopropylamino group, dibutylaminopropylamino group, 2-hydroxyethylaminopropylamino group, laurylaminopropylamino group, diethanolaminopropylamino group, N-aminoethylpiperidinyl group, N-aminoethyl- 4-pipecolinyl group, N-aminoethylmorphonyl group, N-aminopropylpiperidinyl group, N-aminopropyl-2
-Pipeconyl group, N-aminopropylmorphonyl group and the like, but are not limited thereto.

The amine residue introduced into these side chains has a strong affinity with the carboxyl group and the like of the resin component contained in the vehicle. I. Pigment Red 177 is considered to contribute to improvement in dispersibility.

In the present invention, the compound represented by the general formula [2]: I. Pigment Red 177 is C.I. I. Pigment Red 177 is preferably 0.3 to 30 parts by weight with respect to 100 parts by weight. If the amount is less than 0.3 part by weight, the effect is reduced, and if the amount is more than 30 parts by weight, the effect of the amount used is not obtained, and there is a possibility that various resistances of the colored material after use as a pigment composition may be deteriorated. . Most preferred is 0.5 to 20 parts by weight.

In the present invention, C.I. I. Pigment Red 177 and the compound represented by the general formula [2] are mechanically kneaded by a kneader, a two-roll mill, a three-roll mill,
A ball mill, an attritor, a sand mill, or the like can be used, but is not limited thereto.

In the present invention, examples of the water-soluble inorganic salts used for mechanical kneading include salt, potassium chloride, and glass nitrate, but are not limited thereto. Water-soluble inorganic salts include C.I. I. Pigment Red 17
7 is preferably used in an amount of 100 to 2000 parts by weight, more preferably 300 to 1000 parts by weight, per 100 parts by weight.

In the present invention, the solvent used for mechanical kneading is not particularly limited. However, a solvent having a high boiling point is preferred from the viewpoint of safety because the temperature rises during kneading and the solvent is easily evaporated. . Examples include 2- (methoxymethoxy) ethanol, 2-butoxyethanol,
-(Isopentyloxy) ethanol, 2- (hexyloxy) ethanol, diethylene glycol, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, triethylene glycol, triethylene glycol monomethyl ether, liquid polyethylene glycol, 1-methoxy- Examples thereof include 2-propanol, 1-ethoxy-2-propanol, dipropylene glycol, dipropylene glycol monomethyl ether, dipropylene glycol monoethyl ether, and low molecular weight polypropylene glycol. The solvent is C.I. I.
Pigment Red 177 in an amount of 10 to 100 parts by weight.
It is preferred to use 1000 parts by weight, most preferably 50 to 500 parts by weight.

In the present invention, a resin may be added as required during mechanical kneading. The type of the resin used is not particularly limited, and a natural resin, a modified natural resin, a synthetic resin, a synthetic resin modified with a natural resin, or the like can be used. The resin used is preferably solid at room temperature, insoluble in water, and, when a solvent is used during kneading, more preferably partially soluble in the solvent.

In the present invention, the following can be mentioned as examples of the vehicle constituting the coloring composition.
Examples of the vehicle for offset ink include rosin-modified phenolic resin, petroleum resin, alkyd resin, and 20 to 50% by weight of these dry oil-modified resins, and linseed oil,
Those comprising 0 to 30% by weight of a drying oil such as tung oil and soybean oil, and 10 to 60% by weight of a solvent such as n-paraffin, isoparaffin, aromatech, naphthene and α-olefin.

Examples of gravure ink vehicles include:
Gum rosin, wood rosin, tall oil rosin, lime rosin, rosin ester, maleic resin, polyamide resin, vinyl resin, nitrocellulose, cellulose acetate,
Ethyl cellulose, chlorinated rubber, cyclized rubber, ethylene-vinyl acetate copolymer resin, polyurethane resin, polyester resin, alkyd resin, acrylic resin, gilsonite, dammar, shellac, etc. or a mixture thereof, or the above resin or a mixture thereof Water-soluble resin,
Or 10 to 50% by weight of an emulsion resin and a hydrocarbon,
Alcohol, ketone, ether alcohol, ether,
Examples include those comprising 30 to 80% by weight of a solvent such as an ester or water.

Examples of the vehicle for coating include acrylic resin, alkyd resin, epoxy resin, chlorinated rubber, vinyl chloride, synthetic resin emulsion, silicone resin, fluorine resin, polyurethane resin, polyester resin, melamine resin, urea resin and the like. Or a water-soluble resin obtained by making the above resin or a mixture thereof water-soluble, or 20 to 80% by weight of an emulsion resin and 10 to 60% by weight of a solvent such as hydrocarbon, alcohol, ketone, ether alcohol, ether, ester, and water. And those consisting of

Examples of vehicles for plastic include polyethylene, polypropylene, polybutadiene, ethylene ionomer, polyvinyl chloride, polyvinylidene chloride, ABS resin, acrylic resin, methacrylic resin, polyvinyl alcohol, cellulose plastic, epoxy resin, polyester resin. , Phenolic resin, urea resin, melamine resin, polyurethane resin, silicone resin,
Polyamide resin, polystyrene, polyacetal, polycarbonate, polyphenylene ether, polyphenylene sulfite, polysulfone, polyetherimide,
Examples thereof include polyether ketone, and composites thereof.

Examples of aqueous color vehicles include nonionic, anionic and cationic surfactants, sulfonic acid amides, hydroxystearic acid and ε.
-At least one selected from a caprolactam-based polymer dispersant, and a polyhydric alcohol such as glycerin, ethylene glycol, triethylene glycol, propylene glycol, and pentaeristol, water, and, if necessary, an amine,
Those composed of auxiliaries such as preservatives and defoamers are exemplified.

[0037]

EXAMPLES The present invention will be specifically described below with reference to examples. In the examples, all “parts” indicate parts by weight. Example 1 Crude C.I. I. Pigment Red 177: 100 parts, the compound of the formula [5] 5.3 parts, ground salt 700
And 180 parts of diethylene glycol were charged into a stainless steel 1 gallon kneader (manufactured by Inoue Seisakusho) and kneaded at 70 ° C. for 4 hours. Next, this mixture was poured into 4000 parts of warm water, and heated and stirred at about 80 ° C. for 2 hours. At this time, the mixture was in a well-dispersed slurry state in warm water.
The mixture was filtered and washed thoroughly with about 12000 parts of 70 ° C. hot water to remove salt and diethylene glycol;
It was dried in a dryer at 85 ° C. to obtain 95 parts of a pigment composition (a). The specific surface area of the obtained pigment composition was measured by adsorbing nitrogen gas according to the BET one-point method.
It was 105 m ² / g. The pigment composition (a) is added to an alkyd melamine resin varnish for baking paint, and the pigment content is 6% by weight.
, And dispersed by a ball mill to prepare a paint. Table 1 shows the results of measuring the viscosities immediately after removal and storage for one month. Equation [5]

[0038]

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Example 2 Crude C.I. I. Pigment Red 177: 100 parts, the compound represented by the formula [6] 11.1 parts, ground salt 40
0 parts and 150 parts of polyethylene glycol were charged in a stainless steel 1 gallon kneader (manufactured by Inoue Seisakusho), and
Kneaded at 0 ° C. for 3 hours. The mixture is then added to hot water 4000
And stirred with heating at about 80 ° C. for 2 hours. At this time, the mixture was in a well-dispersed slurry state in warm water. The mixture was filtered, washed thoroughly with about 12,000 parts of 70 ° C. hot water to remove salt and polyethylene glycol, and dried in a dryer at 85 ° C. to obtain a pigment composition (b).
105 parts were obtained. The specific surface area of the obtained pigment composition was measured according to the BET one-point method by adsorbing nitrogen gas, and the result was 90 m ² / g. The pigment composition (b) was blended with the alkyd melamine resin varnish for baking paint so that the pigment content was 6% by weight, and dispersed by a ball mill to prepare the paint. Table 1 shows the results of measuring the viscosities immediately after removal and storage for one month. Equation [6]

[0040]

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Further, the C.I. I. Pigment Red 177 (Chromophthal Red A2B manufactured by Ciba Geigy) alone is shown in Table 1 together with Comparative Examples.

[0042]

[Table 1]

The alkyd melamine paints using the pigment compositions (a) and (b) are more excellent in fluidity and crystal stability than the comparative examples, and have beautiful hue and coloring power in the coating film. Excellent gloss. The storage stability was also excellent with a small degree of thickening.

Regarding the dispersion stability, comparison will be made with Examples concerning color separation stability, which is particularly problematic in use. The paints shown in Examples 1 and 2 of Table 1 were cut with a base paint of titanium oxide prepared in advance with an alkyd melamine resin varnish so that the ratio of pigment to titanium oxide was 1/10 to obtain a light-colored paint. Was. The light-colored paint was further diluted with xylene to obtain a Ford Cup No. 4 for 20 seconds (2
The temperature was adjusted to 5 ° C.), and the mixture was injected into a test tube and observed for changes in the glass wall surface. The pigment compositions according to the invention have shown excellent results.

[0045]

[Table 2]

Example 3 Crude C.I. I. Pigment Red 177: 100 parts, the compound represented by the formula [7] 13.5 parts, ground salt 10
00 parts and 200 parts of diethylene glycol were charged into a stainless steel 1 gallon kneader (manufactured by Inoue Seisakusho), and
Kneaded at 0 ° C. for 3 hours. The mixture is then added to hot water 4000
And stirred with heating at about 80 ° C. for 2 hours. At this time, the mixture was in a well-dispersed slurry state in warm water. The mixture was filtered, thoroughly washed with about 12000 parts of 70 ° C. hot water to remove salt and diethylene glycol, and dried in a dryer at 85 ° C. to obtain a pigment composition (c) 9
0 parts were obtained. The specific surface area of the obtained pigment composition was measured according to the BET one-point method by adsorbing nitrogen gas, and as a result, it was 80 m ² / g. The pigment composition (c) was blended with the cyclized rubber varnish for gravure so that the pigment content was 10% by weight, and dispersed by a bead mill to prepare a gravure ink. Its fluidity is referred to as C.I. I. Pigment Red 177
A comparison was made using a B-type viscometer with a gravure ink prepared in the same manner using (Chromophthal Red A3B manufactured by Ciba-Geigy Co., Ltd.) alone. As a result, the one using the pigment composition (c) was remarkably excellent. In addition, excellent results were obtained in the effects on the clarity, transparency, coloring power, and gloss of the color tone of the printed matter printed with the gravure ink. Equation [7]

[0047]

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Example 4 Crude C.I. I. Pigment Red 177: 100 parts, the compound of the formula [8] 1.0 part, ground salt 700
Parts and 200 parts of diethylene glycol were charged into a stainless steel 1 gallon kneader (manufactured by Inoue Seisakusho) and kneaded at 70 ° C. for 4 hours. Next, this mixture was poured into 4000 parts of warm water, and heated and stirred at about 80 ° C. for 2 hours. At this time, the mixture was in a well-dispersed slurry state in warm water.
The mixture was filtered and washed thoroughly with about 12000 parts of 70 ° C. hot water to remove salt and diethylene glycol;
It was dried in a dryer at 85 ° C. to obtain 97 parts of a pigment composition (d). The specific surface area of the obtained pigment composition was measured by adsorbing nitrogen gas according to the BET one-point method.
It was 100 m ² / g. The pigment composition (d) was blended with the cyclized rubber varnish for gravure so that the pigment content was 10% by weight, and dispersed by a bead mill to prepare a gravure ink. Its fluidity is referred to as C.I. I. Pigment Red 177 (Chromophthal Red A3B manufactured by Ciba Geigy) alone was compared with a gravure ink prepared in the same manner using a B-type viscometer, and the result obtained using the pigment composition (d) was remarkably excellent. I was In addition, excellent results were obtained in the effects on the clarity, transparency, coloring power, and gloss of the color tone of the printed matter printed with the gravure ink. Equation [8]

[0049]

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Example 5 Crude C.I. I. Pigment Red 177: 100 parts, the compound of the formula [9] 1.5 parts, ground salt 400
And 250 parts of diethylene glycol were charged into a stainless steel 1 gallon kneader (manufactured by Inoue Seisakusho) and kneaded at 90 ° C. for 4 hours. Next, this mixture was poured into 4000 parts of warm water, and heated and stirred at about 80 ° C. for 2 hours. At this time, the mixture was in a well-dispersed slurry state in warm water.
The mixture was filtered and washed thoroughly with about 12000 parts of 70 ° C. hot water to remove salt and diethylene glycol;
The pigment was dried in a dryer at 85 ° C. to obtain 95 parts of a pigment composition (e). The specific surface area of the obtained pigment composition was measured by adsorbing nitrogen gas according to the BET one-point method.
It was 95 m ² / g. The pigment composition (e) was mixed with the cyclized rubber varnish for gravure so that the pigment content was 10% by weight, and dispersed by a bead mill to prepare a gravure ink. Its fluidity is referred to as C.I. I. Pigment Red 177 (Chromophthal Red A3B, manufactured by Ciba Geigy) alone was compared with a gravure ink prepared in the same manner using a B-type viscometer. The results using the pigment composition (e) were remarkably excellent. I was In addition, excellent results were obtained in the effects on the clarity, transparency, coloring power, and gloss of the color tone of the printed matter printed with the gravure ink. Equation [9]

[0051]

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Example 6 The same excellent results were obtained with a gravure ink prepared using the pigment composition (a) prepared by the method of Example 1 as a cyclized rubber varnish for gravure.

Example 7 The same excellent results were obtained with a gravure ink prepared using the pigment composition (b) prepared by the method of Example 2 as a cyclized rubber varnish for gravure.

The pigment composition obtained by the production method of the present invention can be used in an aromatic solvent at room temperature or at room temperature.
Even when heated to 0 ° C., no crystal transition or growth is observed, and no change in hue and coloring power is caused. C.I. I. The pigment composition obtained by the production method of the present invention shows better dispersibility in a non-aqueous vehicle such as a paint or a gravure ink than when Pigment Red 177 is used without kneading with a kneader. Since it does not cause aggregation, it exhibits good fluidity and, at the same time, does not cause color separation or sedimentation of the pigment even when used in combination with different kinds of pigments. Therefore, the gloss of a printed matter or a coating film becomes good, and a beautiful polymer coloring matter can be obtained. In the production method of the present invention, C.I. I. Pigment Red 177 and the compound represented by the general formula [2] have an extremely high effect in sizing the pigment particles into a fine and uniform shape. The pigment composition obtained by the production method of the present invention has C.I. I. Pigment Red 177 alone is used for kneading with a kneader, and the gloss, clarity, and transparency of the painted film are significantly improved as compared with the obtained pigment composition.

Claims (4)

[Claims] 1. The following general formula [1]: [1] Represented by C.I. I. Pigment Red 177 and the following general formula [2]: [2] (Wherein, X represents a phthalimidomethyl group which may have a substituent, a substituent represented by the following general formula [3] or a substituent represented by the following general formula [4], and p is 1 to And a mixture with a compound represented by the formula (1), which is mechanically kneaded in the presence of a water-soluble inorganic salt or a water-soluble inorganic salt and a solvent to give pigment particles having a specific surface area of 50 to 150 m ² / g.
A method for producing a pigment composition, wherein the pigment is finely sized so that General formula [3] (Wherein, Y is _{-CH 2 NH -, - SO 2} NH -, - CH
₂ NHCOCH ₂ NH-, -CONH-, -CONHC
_{6 H 4 CONH -, - CONHC} 6 H 4 NH -, - SO
_{2 -, - CH 2 NHCOCH 2} -, - CO- represents a divalent linking group selected from, R ^5, R ⁶ are each independently a hydrogen atom, carbon atoms which may have a substituent 1 to 18 An alkyl group, an aryl group which may have a substituent, R ⁵ and R ⁶
And may further contain a nitrogen atom or an oxygen atom, and may have an alkyl group having 5 or less carbon atoms as a substituent.
Represents a 6-membered or 6-membered heterocycle. m represents an integer of 0 to 6. ) General formula [4] (Wherein, Z is _{-NH -, - CH 2 NH -} , - SO 2 NH
_{-, - CH 2 NHCOCH 2 NH} -, - CONHC 6 H 4
_{CONH -, - CONHC 6 H 4} NH-, -CONH
_{-, - SO 2 -, -} CH 2 NHCOCH 2 -, - CO-
R ¹ and R ² each independently represent a hydroxyl group, an alkoxy group which may have a substituent, a phthalimidomethylamino group which may have a substituent, -NH ( CH ₂ ) _n NR ³ R ⁴ (R ³ , R ⁴
Is independently a hydrogen atom, an alkyl group having 1 to 18 carbon atoms which may have a substituent, an aryl group which may have a substituent, and a further nitrogen atom or oxygen atom represented by R ³ and R ⁴ And a 5- or 6-membered heterocyclic ring which may have an alkyl group having 5 or less carbon atoms as a substituent. ), N represents an integer of 1 to 6. ) 2. A pigment composition obtained by the production method according to claim 1. 3. A colorant composition comprising the pigment composition according to claim 2 and a vehicle. 4. The colorant composition according to claim 3, wherein the vehicle is a paint vehicle.