JP3389808B2 - Pigment composition and method for producing the same - Google Patents

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention has excellent suitability for use when dispersed in a vehicle or the like, particularly excellent in non-aggregating property, 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 thereby, and a colorant composition comprising the pigment composition and a vehicle.

[0002]

2. Description of the Related Art C.I. I. Pigment Red 177 (4
4′-diamino-1,1′-dianthraquinonyl) is a practically useful red pigment having a clear color tone and high tinting strength. However, when dispersed in vehicles such as offset inks, gravure inks and paints, especially non-aqueous vehicles, it is difficult to obtain a stable dispersion, and various dispersions which have a significant influence on the manufacturing operation and the value of the obtained product are seriously affected. It often causes problems. 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 in the worse case, gelation during storage can lead to difficulties in use. .

Further, when different kinds of pigments are mixed and used, color unevenness or a marked decrease in coloring power may appear in a color-developed product due to phenomena such as color separation due to aggregation and sedimentation. Further, the surface of the coating film of the color-developed product may be in a state of lowering gloss or poor leveling. Also, in non-aqueous vehicles such as offset inks, gravure inks and paints, C.I. I. Pigment Red 177 crystal particles change in size and morphology and shift to a stable state, so the hue of the developed product may change significantly, the coloring power may decrease, and coarse particles may be generated, impairing the commercial value. .

In order to solve these problems, many proposals have been made centering on copper phthalocyanine pigments and quinacridone pigments. The contents can be roughly classified into the following two categories according to the technical method. The first method is disclosed in US Pat. No. 3,370,971 and USP 2965.
As disclosed in Japanese Patent No. 511, the surface of the pigment particles is coated with a colorless compound such as silicon oxide, aluminum oxide and tertiary butyl benzoic acid. The second method is disclosed in JP-B-41-2466 and USP27.
No. 61865, a method of mixing a compound obtained by using an organic pigment as a base skeleton and introducing a substituent such as a sulfone group, a sulfonamide group, an aminomethyl group or a phthalimidomethyl group into a side chain. .

Compared with the first method, the second method has a significantly greater effect on the non-aggregation property of the pigment in the non-aqueous vehicle, the crystal stability, etc., and is judged from the ease of producing the pigment composition. However, this is a very advantageous method. JP 63-1
In particular, C. 72772 discloses C.I. I. Pigment Red 1
A second method of mixing the sulfonated derivative of 77 has been proposed, but the pigment composition obtained by this method is not sufficiently satisfactory in quality.

In recent years, as the development of new uses for pigment dispersions,
Application to pigment dispersions for liquid crystal display color filters, inkjet pigment dispersions used in inkjet printers, and the like is being promoted. These are intended to use the pigment dispersion in applications such as higher-performance devices. 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 terms of quality and cannot satisfy the required physical properties.

[0008]

SUMMARY OF THE INVENTION The present invention relates to C.I. I. Pigment Red 177 containing pigment pigments having a specific surface area of 50 to 150 m ² is improved.
By enabling the production of a pigment composition finely and uniformly sized so that the amount becomes / g, good flocculation resistance and crystallization resistance against a wide range of compositions of non-aqueous and aqueous vehicles can be obtained. It is intended to provide a method for producing a pigment composition which gives growth 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, water-based colors, printing, toning agents, color toners, pigment dispersions for color filters, and pigment dispersions for inkjet. The present invention provides a pigment composition and a colorant composition comprising the pigment composition and a vehicle.

[0009]

The present invention provides the following general formula [1] general formula [1]

[0010]

[Chemical 5]

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

[0012]

[Chemical 6]

(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
~ Represents an integer of 8. ) With a compound represented by
Mechanically kneading in the presence of water-soluble inorganic salts or water-soluble inorganic salts and a solvent to give pigment particles a specific surface area value of 50 to 1
A method for producing a pigment composition, which comprises finely controlling the particle size to 50 m ² / g. General formula [3]

[0014]

[Chemical 7]

(In the formula, 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-
Represents a divalent bonding group selected from R ⁵ and R ⁶ each independently represents a hydrogen atom or a carbon atom which may have a substituent.
18 alkyl groups, optionally substituted aryl groups,
R ⁵ and R ⁶ represent a 5-membered or 6-membered heterocycle which 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, and m is 0 to 6
Represents the integer. ) General formula [4]

[0016]

[Chemical 8]

(In the formula, 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 linking 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 , R ⁴ are each 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 R ³ and R ⁴ which are further nitrogen atoms. Represents a 5-membered or 6-membered heterocycle which may contain an atom or an oxygen atom and may have an alkyl group having 5 or less carbon atoms as a substituent. ) And n represent the integer of 1-6. )

[0018]

BEST MODE FOR CARRYING OUT THE INVENTION 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 the substituent X into the matrix anthraquinone skeleton. As a method of introducing the substituent X into the anthraquinone skeleton of the matrix, a phthalimidomethyl group which may have a substituent is a known method of reacting with hydroxymethylphthalimide in sulfuric acid, for example, JP-A-55-108466. Can be introduced by the method described in.

Introduction of a substituent having the structure of general formula [3]
As a method, a known method, maternal anthraquinone
-SO in the skeleton₂Cl, -COCl, -CH₂Cl,-
CH ₂NHCOCH₂Compounds in which a substituent such as Cl is introduced
To produce this compound and H ₂N (CH₂)_mNR^FiveR
⁶Or HNR^FiveR⁶(R^Five, R⁶Has the same meaning as above
Represent ) Is reacted with an amine component having a structure of
For example, according to the method described in Japanese Examined Patent Publication No. 1-34268.
Can be introduced.

As the method of introducing the substituent having the structure of the general formula [4], the reaction between the amino group having the mother anthraquinone skeleton or the substituent having an amino group and cyanuric chloride, or the halogen having the mother anthraquinone skeleton is carried out. _{group, -SO 2 Cl, -COCl, -CH} 2 Cl, -C
First, a triazine skeleton is introduced by a reaction of a substituent such as H ₂ NHCOCH ₂ Cl with melamine or a compound having a triazine skeleton, and then a halogen group, a hydroxyl group, an amino group or the like remaining in the triazine skeleton is converted into HN (CH ₂ ) _n
It is reacted with an amine component having the structure of NR ³ R ⁴ (n, R ³ and R ⁴ have the same meanings as described above), alcohols and hydroxymethylphthalimide, for example, as described in JP-B-3-14073. It can be introduced by a method.

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], which is used by mixing with Pigment Red 177, include a phthalimidomethyl group, a chlorophthalimidomethyl group and a dichlorophthalimidomethyl group. Examples thereof include, but are not limited to, a group, a methylphthalimidomethyl group, a dimethylphthalimidomethyl group, a nitrophthalimidomethyl group, and a t-butylphthalimidomethyl group.

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 thereof 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, but are not limited to, a benzene ring residue, a naphthalene ring residue and a nitrogen-containing heterocyclic residue. It is not something that will be done.

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

In the general formula [3] or general formula [4], -N
Examples of the amine residue represented by R ³ R ⁴ or —NR ⁵ R ⁶ include methylamino group, 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-pipecolicinyl group, 2,4-lupetidinyl group, 2,6-lupetidinyl group, 3-piperidinemethanol Group, N-aminopiperidinyl group, N-amino-4
-Pipecorinyl 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, thiomorphonylyl 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-pipecoinyl group, N-aminoethylmorphonylyl group, N-aminopropylpiperidinyl group, N-aminopropyl-2
Examples thereof include, but are not limited to, a -pipeconyl group and an N-aminopropylmorphonylyl group.

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

In the present invention, the compound represented by the general formula [2] is represented by C.I. I. Pigment Red 177 has a mixing ratio of 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 parts by weight, the effect is reduced, and even if it is used in an amount of more than 30 parts by weight, the effect of the amount used cannot be obtained, and there is a possibility that the various resistance of the colored product after use as a pigment composition is 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 to these.

In the present invention, examples of the water-soluble inorganic salts used when mechanically kneading include, but are not limited to, sodium chloride, potassium chloride, and glauber's salt. Water-soluble inorganic salts include C.I. I. Pigment Red 17
It is preferable to use 7 to 100 parts by weight of 100 to 2000 parts by weight, and most preferably 300 to 1000 parts by weight.

In the present invention, the solvent used for mechanical kneading is not particularly limited, but a solvent having a high boiling point is preferable from the viewpoint of safety, since the temperature rises during kneading and the solvent is easily evaporated. . Examples include 2- (methoxymethoxy) ethanol, 2-butoxyethanol, 2
-(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- 2-propanol, 1-ethoxy-2-propanol, dipropylene glycol, dipropylene glycol monomethyl ether, dipropylene glycol monoethyl ether, low molecular weight polypropylene glycol and the like can be mentioned. The solvent is C.I. I.
Pigment Red 177 is 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 necessary when mechanically kneading. The type of resin used is not particularly limited, and natural resin, modified natural resin, synthetic resin, synthetic resin modified with natural resin, and the like can be used. The resin used is preferably solid at room temperature, insoluble in water, and more preferably partially soluble in a solvent when a solvent is used during kneading.

In the present invention, the following may be mentioned as examples of vehicles constituting the coloring composition.
Examples of the vehicle for offset ink include 20 to 50% by weight of rosin-modified phenol resin, petroleum resin, alkyd resin, or a drying oil-modified resin thereof, and linseed oil,
Examples include dry oils such as tung oil and soybean oil in an amount of 0 to 30% by weight, and solvents such as n-paraffin, isoparaffin, aromatech, naphthene, and α-olefin in an amount of 10 to 60% by weight.

Examples of gravure ink vehicles include:
Gum rosin, wood rosin, tall oil rosin, lime rosin, rosin ester, maleic acid 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 mixtures thereof, or the above resins or mixtures thereof are water-solubilized. Water soluble resin,
Or 10 to 50% by weight of emulsion resin and hydrocarbon,
Alcohol, ketone, ether alcohol, ether,
Examples include those containing 30 to 80% by weight of a solvent such as ester and water.

Examples of the vehicle for paint are acrylic resin, alkyd resin, epoxy resin, chlorinated rubber, vinyl chloride, synthetic resin emulsion, silicone resin, fluororesin, polyurethane resin, polyester resin, melamine resin, urea resin, etc. Or a water-soluble resin obtained by water-solubilizing the above resin or a mixture thereof, 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 or water. It is made of.

Examples of vehicles for plastics are polyethylene, polypropylene, polybutadiene, ethylene ionomer, polyvinyl chloride, polyvinylidene chloride, ABS resin, acrylic resin, methacrylic resin, polyvinyl alcohol, cellulosic plastic, epoxy resin, polyester resin. , Phenol 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 water-based color vehicles include nonionic, anionic, and cationic surfactants, sulfonic acid amides, hydroxystearic acid, and ε.
At least one selected from caprolactam-based polymer dispersants, polyhydric alcohols such as glycerin, ethylene glycol, triethylene glycol, propylene glycol, and pentaerythritol, water, and optionally an amine,
Examples include auxiliary agents such as preservatives and defoaming agents.

[0037]

EXAMPLES The present invention will be specifically described below with reference to examples. In the examples, all "parts" are parts by weight. Example 1 Crude C.I. I. Pigment Red 177: 100 parts, 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 put into 4000 parts of warm water, and heated and stirred at about 80 ° C. for 2 hours. At this time, the mixture was in the form of a well-dispersed slurry in warm water.
The mixture is filtered and washed thoroughly with about 12000 parts of hot water at 70 ° C. to remove salt and diethylene glycol,
It was dried in a drier at 85 ° C. to obtain 97 parts of a pigment composition (a). The specific surface area of the obtained pigment composition was measured by the BET one-point method by adsorbing nitrogen gas,
It was 95 m ² / g. The pigment composition (a) was blended in an alkyd melamine resin varnish for baking paint so that the pigment content was 6% by weight, and dispersed by a ball mill to prepare a paint. Table 1 shows the results of measuring the viscosity immediately after taking out and storing for one month. Expression [5]

[0038]

[Chemical 9]

Example 2 Crude C.I. I. Pigment Red 177: 100 parts, 11.1 parts of the compound represented by the formula [6], ground salt 40
Charge 0 part and 150 parts of polyethylene glycol into a stainless steel 1 gallon kneader (manufactured by Inoue Seisakusho) and
Kneading was carried out at 0 ° C. for 3 hours. This mixture is then mixed with warm water 4000
It was put into a part and heated and stirred at about 80 ° C. for 2 hours. At this time, the mixture was in the form of a well-dispersed slurry in warm water. The mixture was filtered, washed thoroughly with about 12000 parts of hot water at 70 ° C to remove salt and polyethylene glycol, and dried in a drier at 85 ° C to prepare the pigment composition (b).
105 parts were obtained. The specific surface area of the obtained pigment composition was 85 m ² / g as measured by the BET one-point method by adsorbing nitrogen gas. The alkyd melamine resin varnish for baking paint was mixed with the pigment composition (b) so that the pigment content was 6% by weight, and dispersed by a ball mill to prepare a paint. Table 1 shows the results of measuring the viscosity immediately after taking out and storing for one month. Expression [6]

[0040]

[Chemical 10]

Further, the C.I. I. Table 1 also shows a comparative example in which Pigment Red 177 (Chromophtal Red A2B manufactured by Ciba Geigy) was used alone.

[0042]

[Table 1]

The alkyd melamine paints using the pigment compositions (a) and (b) are superior in fluidity and crystal stability as compared with Comparative Examples, and the coating film has beautiful hue and strong coloring power. It was excellent in gloss. Moreover, the storage stability was also excellent with a small degree of thickening.

The dispersion stability will be compared with reference to Examples of color separation stability which are particularly problematic in use. The paints shown in Examples 1 and 2 in Table 1 were cut with a titanium oxide base paint preliminarily adjusted with an alkyd melamine resin varnish so that the ratio of pigment to titanium oxide was 1/10 to obtain a light-colored paint. It was This light-colored paint was further diluted with xylene to obtain Ford Cup No. 20 seconds (4
Table 2 shows the results of adjusting the temperature to 5 ° C.), injecting it into a test tube, and observing changes in the glass wall surface. The pigment composition according to the invention showed excellent results.

[0045]

[Table 2]

Example 3 Crude C.I. I. Pigment Red 177: 100 parts, compound of the formula [7] 13.5 parts, ground salt 10
00 parts and diethylene glycol 200 parts were charged into a stainless steel 1-gallon kneader (manufactured by Inoue Seisakusho), and 12
Kneading was carried out at 0 ° C. for 3 hours. This mixture is then mixed with warm water 4000
It was put into a part and heated and stirred at about 80 ° C. for 2 hours. At this time, the mixture was in the form of a well-dispersed slurry in warm water. The mixture was filtered, washed thoroughly with about 12,000 parts of hot water at 70 ° C. to remove salt and diethylene glycol, and dried in a drier at 85 ° C. to prepare pigment composition (c) 9
I got 0 copies. The specific surface area of the obtained pigment composition was 80 m ² / g as measured by the BET one-point method after adsorbing nitrogen gas. The pigment composition (c) was added to 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 liquidity is C.I. I. Pigment Red 177
(Chiba Geigy Co., Ltd., Chromophtal red A3B) was used alone, and a gravure ink prepared in the same manner was compared with a B-type viscometer. As a result, the pigment composition (c) was remarkably excellent. In addition, excellent results were obtained in terms of the effect on the vividness, transparency, tinting strength, and gloss of the printed matter printed with the gravure ink. Expression [7]

[0047]

[Chemical 11]

Example 4 Crude C.I. I. Pigment Red 177: 100 parts, 1.5 parts of the compound represented by the formula [8], 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 put into 4000 parts of warm water, and heated and stirred at about 80 ° C. for 2 hours. At this time, the mixture was in the form of a well-dispersed slurry in warm water.
The mixture is filtered and washed thoroughly with about 12000 parts of hot water at 70 ° C. to remove salt and diethylene glycol,
It was dried in a drier at 85 ° C. to obtain 90 parts of a pigment composition (d). The specific surface area of the obtained pigment composition was measured by the BET one-point method by adsorbing nitrogen gas,
It was 80 m ² / g. The cyclized rubber varnish for gravure was mixed with the pigment composition (d) so that the pigment content was 10% by weight, and dispersed by a bead mill to prepare a gravure ink. Its liquidity is C.I. I. Pigment Red 177 (Chiba Geigy's Chromophtal Red A3B) used alone to compare with a gravure ink similarly prepared using a B-type viscometer. The pigment composition (d) is remarkably excellent. Was there. In addition, excellent results were obtained in terms of the effect on the vividness, transparency, tinting strength, and gloss of the printed matter printed with the gravure ink. Expression [8]

[0049]

[Chemical 12]

Example 5 Crude C.I. I. Pigment Red 177: 100 parts, 1.0 part of the compound represented by the formula [9], 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 put into 4000 parts of warm water, and heated and stirred at about 80 ° C. for 2 hours. At this time, the mixture was in the form of a well-dispersed slurry in warm water.
The mixture is filtered and washed thoroughly with about 12000 parts of hot water at 70 ° C. to remove salt and diethylene glycol,
It was dried in a drier at 85 ° C. to obtain 105 parts of a pigment composition (e). 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 105 m ² / g. The pigment composition (e) was added to 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 liquidity is C.I. I. Pigment Red 177
(Chiba Geigy Co., Ltd., Chromophtal red A3B) was used alone, and a gravure ink similarly prepared was compared with a B-type viscometer. As a result, the pigment composition (e) was significantly superior. In addition, excellent results were obtained in terms of the effect on the vividness, transparency, tinting strength, and gloss of the printed matter printed with the gravure ink. Expression [9]

[0051]

[Chemical 13]

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

Example 7 The same excellent result was obtained with the gravure ink prepared by using the pigment composition (b) prepared by the method of Example 2 in the cyclized rubber varnish for gravure.

The pigment composition obtained by the method of the present invention can be used in an aromatic solvent at room temperature as well as 16
No crystal transition or growth was observed even when heated to 0 ° C., and the hue and tinting strength were not changed. In addition, C.I. I. The pigment composition obtained by the production method of the present invention shows good dispersibility in a non-aqueous vehicle such as a paint or a gravure ink, as compared with the case where Pigment Red 177 is used without kneading with a kneader. Since it does not cause agglomeration, 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 pigments. Therefore, the gloss of the printed matter or the coating film becomes good, and a beautiful polymer coloring matter can be obtained. In the production method of the present invention, C.I. I. The compound represented by the general formula [2], which is mixed with Pigment Red 177, exhibits 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 subjected to kneading with a kneader, and the gloss, sharpness and transparency of the paint film of the color-developed product are remarkably improved as compared with the pigment composition obtained.

─────────────────────────────────────────────────── ─── Continuation of front page (51) Int.Cl. ⁷ identification code FI C09D 7/12 C09D 7/12 Z 11/00 11/00 (56) References Japanese Patent Laid-Open No. 1-247468 (JP, A) Kai 61-168666 (JP, A) JP 56-118642 (JP, A) JP 6-212088 (JP, A) JP 63-172772 (JP, A) JP 6-228454 ( (58) Fields investigated (Int.Cl. ⁷ , DB name) C09B 67/04 C09B 67/20 C09B 67/08 C09B 67/22

Claims (4)

(57) [Claims] 1. The following general formula [1] general formula [1] Represented by C.I. I. Pigment Red 177 and the following general formula [2] general formula [2] (In the formula, 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 Which represents an integer of 8) 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 a specific surface area value of 50 to 150 m ² / g.
A method for producing a pigment composition, which comprises finely sizing the particles 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-
And 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, or —NH ( CH ₂ ) _n NR ³ R ⁴ (R ³ , R ⁴
Are each 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 for R ³ and R ^4. And represents a 5-membered or 6-membered heterocycle which may have an alkyl group having 5 or less carbon atoms as a substituent. ) And n represent the integer of 1-6. ) 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 vehicle for paints.