KR101620287B1 - Pigment dispersant, pigment composition and pigment-based colorant - Google Patents

Abstract

Provided is a pigment dispersant which can substantially improve flowability of pigment-containing ink or paint, etc., and can prevent flocculation of pigment particles. Also, the pigment dispersant can prevent generation of foreign substances, and can manufacture a colored product exhibiting excellent gloss and clarity. The pigment dispersant is represented by chemical formulas (I-A) and (II-A).

Description

PIGMENT DISPERSANT, PIGMENT COMPOSITION AND PIGMENT-BASED COLORANT,

The present invention relates to a pigment dispersant, a pigment composition, and a pigment colorant.

In general, it is difficult to mix and disperse pigments (particles) in a stable state in vehicles such as paints, gravure inks, and offset inks. For example, fine pigment particles once dispersed in a vehicle tend to agglomerate in the vehicle. There is a problem that the viscosity of the vehicle in which the pigment particles are agglomerated increases. Further, when a vehicle in which agglomerated pigment particles are dispersed is used, various problems such as deterioration of the coloring power of the ink and the paint, and gloss of the coating film are liable to occur.

[0004] However, a color filter used for manufacturing a liquid crystal color display, an image pickup device, and the like is manufactured, for example, by the following method using a pigment dispersion. First, a pigment dispersion for a color filter (pigment colorant for a color filter (CF)) in which three color pigments of red (R), green (G) and blue (B) are dispersed in a photosensitive resin liquid is prepared. These CF pigment colorants are applied to a substrate for a color filter according to a spin coating method to form a colored film. Next, a color filter can be obtained by exposing a colored film formed through a photomask and then developing it to pattern the colored film and forming a desired pixel on the substrate.

Examples of pigments for producing color filters include green pigments, red pigments, and blue pigments. As the green pigment, for example, C.I. (Hereinafter referred to as " PG ") 36, PG7, and PG58. As the red pigment, for example, C.I. Diketopyrrolopyrrole red such as Pigment Red (hereinafter referred to as " PR ")254; Anthraquinone red such as PR177; Azo red such as PR242 is generally used. As the blue pigment, for example, C.I. Phthalocyanine blue such as Pigment Blue (hereinafter referred to as " PB ") 15: 6 is generally used.

Further, since there is a difference between the hue of these pigments and the color characteristics required for liquid crystal displays, pigments for complementary colors are used in combination. For example, for green and red pigments, C.I. Pigment Yellow (hereinafter referred to as " PY ") 138, PY139, and PY150 are used in small quantities as pigments for complementary colors. As for the blue pigment, C.I. Pigment violet (hereinafter referred to as " PV ") 23) are used in small quantities as pigments for complementary colors. In order to form a good pixel of the color filter, it is preferable that the predominant pigment and the complementary color pigment exist in a uniform state in the CF pigment colorant.

However, it is difficult to disperse the above-mentioned pigment into a dispersion medium such as a photosensitive resin liquid using a conventional dispersing machine as well as when the pigment is used in combination, and when only a pigment dispersion in which the dispersion state of the pigment is poor is not obtained . A pixel of a color filter formed using a pigment coloring agent for CF having a poor dispersion state of the pigment becomes insufficient in light transmittance and the light transmittance as a pixel of the color filter becomes insufficient. That is, the pigment colorant for CF obtained by dispersing the pigment using a conventional dispersing machine is not sufficient as a coloring agent for forming pixels of the color filter.

On the other hand, as a photosensitive resin for a photoresist which is a pigment dispersion medium, an acrylic polymer having a high acid value is mainly used so that a colored film after exposure can be easily developed into an aqueous alkali solution as a developer. However, the above-mentioned pigment and a pigment colorant containing an acrylic polymer having a high acid value have a problem that the pigment easily agglomerates and the viscosity tends to be high. In addition, since agglomeration of pigment progresses due to aging, the storage stability is low. In addition, when a color filter is produced by using a pigment colorant exhibiting a high viscosity, or a pigment having a viscosity which is aggregated and thixotropic, the central portion of the colored film before exposure may swell up. For this reason, there arises a problem that a pixel located at the center of the substrate and a pixel located at the peripheral portion cause a difference in color and density. This problem becomes more prominent when a larger color filter is to be manufactured.

Therefore, the pigment colorant for CF (photoresist) has a high dispersibility in the photosensitive resin which is a dispersion medium of the pigment while containing the pigment at a high concentration, and has a low viscosity as compared with a normal dry paint or baking paint . Generally, even if the pigment concentration is from 5 to 20 mass%, it is required that the pigment is not agglomerated, its viscosity is about 5 to 20 mPa · s, and the storage stability is good.

In order to satisfy the above requirements, conventionally, a method of adding a pigment derivative as a dispersing agent of a pigment, a method of using a pigment treated with a pigment derivative, and the like have been proposed. Specifically, when diketopyrrolopyrrole red such as PR254 is used as a pigment, it has been proposed to use a substituted derivative of diketopyrrolopyrrole as a pigment dispersant. Further, when an anthraquinone red such as PR177 is used as a pigment, it has been proposed to use a substituted derivative of anthraquinone as a pigment dispersant (for example, see Patent Documents 1 to 3).

Japanese Patent Application Laid-Open No. 2001-240780 Japanese Patent Application Laid-Open No. 2001-174616 JP-A-2009-029886

In recent years, there is a desire to further improve the performance of color filters. Specifically, it is required to further improve the transparency of the colored pixel, increase the contrast of the transmitted light of the colored pixel, or increase the pigment concentration of the colored pixel. However, it has been difficult to obtain a pigment colorant capable of producing a color filter that satisfies the above-mentioned performance in the conventional techniques as proposed in Patent Documents 1 to 3 and the like. In addition, the pigment colorant obtained by the conventional technique is not limited to the color filter, but foreign matter may be generated in the formed coating film (colored film), and therefore improvement is desired.

The present invention has been made in view of the problems of such prior arts, and it is an object of the present invention to provide a pigment which can remarkably improve the fluidity of an ink or a paint containing a pigment, And a pigment dispersant capable of producing a colored article exhibiting excellent gloss and sharpness while preventing the generation of foreign matter. Another object of the present invention is to provide a pigment composition and a pigment colorant obtained by using the pigment dispersant.

That is, according to the present invention, the following pigment dispersant is provided.

[1] A pigment dispersant which is a compound represented by any one of the following formulas (I-A) to (I-F) and (II-A) to (II-F)

Further, according to the present invention, the following pigment compositions are provided.

[2] A pigment composition comprising the pigment and the pigment dispersant according to the above [1].

[3] The pigment composition according to the above [2], wherein the blending amount of the pigment dispersant relative to 100 parts by mass of the pigment is 0.5 to 40 parts by mass.

Further, according to the present invention, there is provided a pigment colorant described below.

[4] A pigment colorant comprising the pigment composition according to [2] or [3] and a film-forming material.

[5] A pigment colorant according to the above-mentioned [4], wherein the pigment colorant is for image display, image recording, printing ink, writing ink, plastic, pigment printing, or paint.

[6] The pigment colorant according to [4], which is used for a color filter.

INDUSTRIAL APPLICABILITY The pigment dispersant of the present invention can remarkably improve the fluidity of inks and paints containing pigments, and can prevent particle aggregation of the pigments, and exhibits excellent gloss and sharpness while preventing the generation of foreign matter A colored article can be manufactured. For this reason, the pigment dispersant of the present invention can be used in various fields such as printing inks such as offset ink and gravure ink, various paints, plastics, pigment flame retardants, dry or liquid toner for electrophotography, ink for inkjet recording, ink for thermal transfer recording, And can be suitably used for a vehicle to be used for an ink for a resist for a writing tool or the like. Further, by using the pigment dispersant of the present invention, it is possible to provide a pigment composition and a pigment colorant capable of remarkably improving the fluidity of various paints and the like, preventing aggregation of the pigment particles and forming a colored film effectively prevented from generation of foreign matter Can be provided. Further, the pigment colorant of the present invention can hardly cause thickening or gelation at the time of storage, and can produce a colorant having excellent gloss and sharpness. For this reason, the pigment colorant of the present invention is particularly suitable as a pigment colorant for color filters and the like.

Hereinafter, an embodiment of the present invention will be described, but the present invention is not limited to the following embodiments.

<Pigment dispersant>

DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS Hereinafter, the present invention will be described in detail with reference to preferred embodiments. The pigment dispersant of the present invention is one of the main characteristics that is a compound represented by the following general formula (I-1), a quaternary ammonium salt of the compound, an amine salt of the compound, or a metal salt of the compound. Further, the pigment dispersant of the present invention is one of the main characteristics that is a compound represented by the following general formula (II-1). The pigment dispersant of the present invention having such characteristics has excellent affinity for various pigments and can be suitably used as a pigment dispersant for dispersing various pigments regardless of organic or inorganic pigments. In addition, since the pigment dispersant of the present invention has an excellent pigment dispersing effect, it can be used as a material for preparing pigment colorants for various purposes.

In the general formula (I-1), X represents a residue of an aromatic compound or a heterocyclic compound which may have a substituent. The bonding site with "N = N-" in the general formula (I-1) is an aromatic ring of the aromatic compound or a heterocyclic ring of the above-mentioned heterocyclic compound. In the general formula (I-1), n represents a number of 0.2 to 3. N in the general formula (1) means the average number of sulfonic acid groups introduced into the compound represented by the general formula (1).

In the general formula (II-1), X represents a residue of an aromatic compound or a heterocyclic compound which may have a substituent. The bonding site with "N = N-" in the general formula (II-1) is an aromatic ring of the aromatic compound or a heterocyclic ring of the above-mentioned heterocyclic compound. Y in the general formula (II-1) represents a reactive residue of an aliphatic amine, an alicyclic amine, or a heteroalicyclic amine having 2 to 30 carbon atoms and having a basic nitrogen atom. The bonding site with "O ₂ S-" in the general formula (II-1) is a nitrogen atom of the above-mentioned aliphatic amine, the above-mentioned alicyclic amine, or the above-mentioned heteroalicyclic amine. In the general formula (II-1), n represents a number of from 0.2 to 3. N in the general formula (II-1) means the average number of introduced groups represented by "-SO ₂ Y" in the compound represented by the general formula (1).

The pigment dispersant of the present invention exhibits an excellent effect as a dispersant of a pigment even in a small amount. Further, the pigment composition and the pigment colorant prepared using the pigment dispersant of the present invention hardly cause thickening or gelation at the time of storage, and foreign matter is hardly generated in the coating film formed by using them. Specific examples of the pigment dispersant of the present invention include compounds represented by the following formulas (I-A) to (I-F) and the following formulas (II-A) to (II-F).

More specific examples of the pigment dispersant of the present invention include compounds represented by the following formulas (I-1-1) to (I-1-8) and the following formulas (II-1-1) to .

The compound (pigment dispersant) represented by the general formula (I-1) can be synthesized, for example, as follows. First, an aromatic compound or a heterocyclic compound having an amino group such as 1-aminoanthraquinone is diazotized by a conventional method and then coupled with 2,4-dihydroxyquinoline to obtain an intermediate. When the obtained intermediate is sulfonated by a conventional method using a known sulfonating agent such as fuming sulfuric acid, a compound (pigment dispersant) represented by the general formula (I-1) can be obtained. In addition, the pigment dispersant of the present invention may contain a small amount of unreacted raw materials, and as long as the effect of the present invention can be obtained, a small amount of unreacted raw materials may be contained.

The compound (pigment dispersant) represented by the general formula (II-1) can be synthesized, for example, as follows. First, an aromatic compound or a heterocyclic compound having an amino group such as 1-aminoanthraquinone is diazotized by a conventional method and then coupled with 2,4-dihydroxyquinoline to obtain an intermediate. Next, an intermediate obtained in chlorosulfonic acid at 50 to 60 ° C is chlorosulfonylated, and then precipitated in ice water (ice water), followed by filtration and washing with ice water to obtain a chlorosulfonylated water paste. The resulting chlorosulfonylated compound is reacted with an amine compound having a basic nitrogen atom such as N, N-diethylaminopropylamine at 50 to 60 ° C to give a compound (pigment dispersant) represented by the general formula (II-1) Can be obtained. In addition, the pigment dispersant of the present invention may contain a small amount of unreacted raw materials and sulfone and other by-products. As long as the effect of the present invention can be attained, these unreacted raw materials and by-products may be slightly contained .

Specific examples of the aromatic compound and heterocyclic compound having an amino group which can be used in the above synthesis method include aniline, toluidine (o-, m- or p-), 2,4-xylidine, Aminophenol (o-, m- or p-), anthranilic acid, p-aminobenzoic acid, nitroaniline (o-, m- or p-), anthracene, Or p-), chloroaniline (o-, m- or p-), 2,5-dichloroaniline, 3,4-dichloroaniline, 3,5-dichloroaniline, 2,3,4- trichloroaniline, 2 , 2,4-trichloroaniline, 3,4,5-trichloroaniline, 2-chloro-4-nitroaniline, 5-chloro-2-nitroaniline, 2,6 -Dichloro-4-nitroaniline, o-fluoroaniline, 2,4-difluoroaniline, m-trifluoromethylaniline, 2-chloro-5-trifluoromethylaniline, 2-aminothiophenol, 2 -Amino-5-nitrobenzonitrile, 2-amino-3-bromo-5-nitrobenzo Aminopyridine, 2-aminothiazole, 2-amino-5-nitrothiazole, 2-aminopyridine, 2-aminopyridine, Aminobenzothiazole, 1-aminoanthraquinone, 2-aminoanthraquinone, 5-amino-2-benzimidazolinone, 4-aminophthalimide, 4-amino-N-methylphthalimide, o- (phenylsulfonyl) aniline, 2-ethylsulfonyl-5-methoxyaniline, 2- ethylsulfonyl-5-trifluoromethylaniline, Amino-4-methoxybenzamide, 3-amino-4-methoxybenzamide, 3-amino-4-methoxybenzylamide, Aminobenzamide, 2-amino-4,4'-dichlorodiphenyl ether, 4-benzamide-2,5-dimethoxyaniline, 9-aminoacridine, 6- . Among them, 1-aminoanthraquinone and 5-amino-2-benzimidazolinone are preferable.

Examples of the amine forming the sulfonic acid group and the amine salt in the general formula (I-1) include amines such as (mono, di or tri) alkylamines, substituted or unsubstituted alkylenediamines, Ammonium chloride, and the like. Among them, a quaternary ammonium salt is preferable. Examples of the metal forming the sulfonate group and the metal salt in the general formula (I-1) include alkali metals such as Li, Na and K; Ca, Ba, Al, Mn, Sr, Mg, Ni, and the like.

Specific examples of the amine compound having a basic nitrogen atom include N, N-dimethylaminomethylamine, N, N-diethylaminomethylamine, N, N-dipropylaminomethylamine, N, Amines such as N, N-dimethylaminoethylamine, N, N-diethylaminoethylamine, N, N-dipropylaminoethylamine, N, N-dibutylaminoethylamine, N, N-diethylaminobutylamine, N, N-dipropylaminobutylamine, N, N-diethylaminopropylamine, , N-dibutylaminobutylamine, N, N-dimethylaminolaurylamine, N, N-diethylaminolaurylamine, N, N-dibutylaminolaurylamine, N, , N, N-diethylaminostearylamine, N, N-diethanol aminoethylamine, N, N-diethanolaminopropylamine, N- (3-aminopropyl) cyclohexylamine, N- Nop N, N ", N "), N, N-diethylaminoethoxypropylamine, N, N, N ", N" -tetra (n-propyl) diethylenetriamine, N, N " , N ", N", tetra (i-propyl) diethylenetriamine, N, N, N " (N, N-dimethylpropylamine), 3, 4'-diethylenetriamine, N, N, (N, N-di (n-propyl) propylamine), 3,3'-iminobis (N, N-diethylpropylamine) (N-butyl) propylamine), 3,3'-iminobis (N, N-di (i- (N, N-dimethylpropylamine), 2,9-dimethyl-2,5,9-triazadecane, 2,10-dimethyl- Azadecane, 2,12-dimethyl-2,6,12-triazatridecane, 2,12-dimethyl-2,5,12-triazatridecane, 2,16-dimethyl-2,9,16-tri Di (n-butyl) -5,9,13-triazaheptadecane, di (2-picolyl) ) Amine, di (3-picolyl) amine, and the like. Of these, N, N-diethylaminopropylamine and N- (3-aminopropyl) cyclohexylamine are preferred.

The method of using the pigment dispersant of the present invention is not particularly limited, but the following usage methods are exemplified. In any of these methods, a desired pigment dispersion effect can be obtained.

(1) A pigment and a pigment dispersant are mixed in advance by a known method, and the obtained pigment composition is added to a vehicle or the like to disperse the pigment in the vehicle.

(2) A pigment and a pigment dispersant are separately added to the vehicle at a predetermined ratio to disperse the pigment in the vehicle.

(3) The pigment and the pigment dispersant are separately dispersed in a vehicle or the like, and the obtained dispersions are mixed at a predetermined ratio, and the pigment is dispersed in the vehicle.

(4) To a dispersion obtained by dispersing a pigment in a vehicle or the like, a pigment dispersant is added in a predetermined ratio to disperse the pigment in the vehicle.

In the above methods (1) to (4), a polymer dispersant having a counter ionic group (counter ionic group) in the compound represented by formula (I-1) And then dispersed. Particularly, in the method (1) or (2), it is preferable to use the polymer dispersant in combination with a polymer dispersant having a cationic group.

<Pigment composition>

The pigment composition of the present invention contains a pigment and the above-mentioned pigment dispersant. The blending amount of the pigment dispersant relative to 100 parts by mass of the pigment is preferably 0.5 to 40 parts by mass, more preferably 1 to 20 parts by mass. If the blending amount of the pigment dispersant is less than the above-mentioned range, the effect of the desired dispersant may not be sufficiently obtained. On the other hand, if the blending amount of the pigment dispersant is larger than the above-mentioned range, the effect of the dispersant becomes a peak, and further effects can not be expected, and the material cost becomes high, which may be disadvantageous from the viewpoint of productivity. Further, in paints or inks using a pigment composition containing such a pigment dispersant in excess, the physical properties of the vehicle may be deteriorated, or the color of the pigment may vary greatly depending on the color of the pigment dispersant itself.

Specific examples of the pigments for obtaining an effective dispersing effect by using the pigment dispersant of the present invention include soluble and insoluble azo pigments, high molecular weight azo pigments, phthalocyanine pigments, quinacridone pigments, anthraquinone pigments, diketopyrrolopyrrole pigments, Naphthalone pigments, methine azomethine pigments, perylene pigments, perinone pigments, isoindolinone pigments, isoindoline pigments, metal complex pigments, and the like. Among them, particularly, when a pigment is used in a red color, a more remarkable effect can be obtained, which is preferable. As the pigment whose color is red, PR254 which is a diketopyrrolopyrrole pigment and PR177 which is an anthraquinone pigment are preferable.

The method for producing the pigment composition of the present invention is not particularly limited. For example, when the pigment and the pigment dispersant are mixed by a conventionally known method, the pigment composition of the present invention can be obtained. Specific examples of the method for producing the pigment composition of the present invention include the following methods (1) to (4).

(1) A method of mixing a powder of a pigment and a powder of a pigment dispersant without using a dispersing machine.

(2) A method of mechanically mixing a pigment and a pigment dispersant with various dispersers such as a kneader, a roll, an attritor, and a horizontal bead mill.

(3) A method in which a liquid in which a pigment dispersant is dissolved or finely dispersed is added to and mixed with an aqueous or organic solvent-based suspension of the pigment, and the pigment dispersant is uniformly deposited on the surface of the pigment.

(4) A method in which a pigment and a pigment dispersant are dissolved in a solvent having a strong dissolving power such as sulfuric acid and co-precipitated with a poor solvent such as water.

The property of the pigment dispersant used for preparing the pigment composition may be any of a solution, a slurry, a paste, and a powder. A desired effect can be obtained even when a certain kind of pigment dispersant is used.

&Lt; Pigment coloring agent &

The pigment colorant of the present invention contains the above-mentioned pigment composition and a film-forming material. The pigment coloring agent of the present invention can be obtained by mixing, for example, the above-mentioned pigment composition which has been made finer and a film forming material such as a resin ((co) polymer), an oligomer or a monomer selected corresponding to its use. The pigment coloring agent of the present invention can be used in a wide range of fields as a coloring agent for image display, image recording, printing ink, writing ink, plastics, pigment printing, painting and the like. Particularly, as an image display material in which the transparency of a colored pixel is a problem, it is suitable as a pigment colorant for a color filter. Of course, the pigment coloring agent of the present invention is also useful as a material for an image recording material such as dry or liquid toner for electrophotography, ink for inkjet recording, ink for electrodeposition recording, ink for thermal transfer recording, . The materials for these image recording materials are used in various image recording methods such as an inkjet recording method, an electrodeposition recording method, and an electrophotographic method. By using the pigment coloring agent of the present invention, it is possible to prepare a material for an image recording agent capable of providing a high-quality image in any image recording method.

Hereinafter, a pigment dispersion for a color filter (a pigment colorant for a color filter (CF)), which is a pigment coloring agent for image display, will be described as a representative example of the pigment colorant of the present invention. In order to prepare a pigment dispersion (photoresist) for a color filter, firstly, the above-mentioned pigment composition is added to a liquid containing a film-forming material and premixed. Next, by dispersing, a pigment dispersion for a color filter can be obtained. More specifically, a pigment composition uniformly polished by using a dispersing machine such as a vertical type medium dispersing machine, a horizontal type medium dispersing machine, a ball mill or the like is applied to a liquid containing a film-forming material To obtain a pigment dispersion for a color filter. Further, the pigment and the pigment dispersant are dissolved in sulfuric acid or the like, and the resulting solution is mixed with water, and the pigment composition containing the pigment and the pigment dispersant is precipitated and separated as a solid solution or an eutectoid. The separated pigment composition may be added to and mixed with a liquid containing a film-forming material or a polymer dispersant and then subjected to pulverization and dispersion using a horizontal type wet medium disperser (bead mill) such as a dyno mill, A pigment dispersion can be obtained.

The pigment colorant of the present invention may further contain a polymer dispersant. As the polymer dispersant, a basic polymer dispersant is preferred. The surface of the pigment in the pigment colorant of the present invention is treated with an acidic pigment dispersant represented by the general formula (1). Therefore, by containing a basic polymer dispersant, a pigment dispersion for a color filter having a lower viscosity and a higher contrast can be obtained. In addition, when an acidic polymer dispersant is contained, the pigment may aggregate, and the pigment colorant may be easily thickened.

As the polymer dispersant, a known dispersant can be used. DISPERBYK-182, DISPERBYK-163, DISPERBYK-163, DISPERBYK-166, DISPERBYK-171, DISPERBYK-182, DISPERBYK- DISPERBYK-2000, DISPERBYK-2001, DISPERBYK-2070 and DISPERBYK-2150 (all manufactured by BYK ADDITIVES &INSTRUMENTS); EFKA-44, EFKA-44, EFKA-47, EFKA-48, EFKA-4010, EFKA-4015, EFKA-4020, EFKA-4050, EFKA- 4400, EFKA-4406, EFKA-4510, EFKA-4800 (all manufactured by BASF); SOLSPERS-24000, SOLSPERS-32550, NBZ-4204/10 (above, manufactured by Lubrizol); Hinoact T-6000, Hinoact T-7000, Hinoact T-8000 (manufactured by Kawaken Fine Chemicals Co., Ltd.); Ajispa-PB-821, Ajispa-PB-822 and Ajispa-PB-823 (all manufactured by Ajinomoto Fine-Techno Co., Inc.).

Specific examples of the basic polymeric dispersant include KF-10000 (trade name, manufactured by Kawaken Fine Chemicals); Alpha Resin SA-300 (manufactured by Alpha Kenshin Co., Ltd.); DISPERBYK-110, DISPERBYK-111, DISPERBYK-180 (all manufactured by Big Chemicals); SOLSPERS-41000 (manufactured by Lubrizol); Aji Spa-PA-111 (Ajinomoto Fine Technosaje).

The blending amount of the polymeric dispersing agent is preferably 2 to 100 parts by mass, more preferably 10 to 50 parts by mass with respect to 100 parts by mass of the pigment. If the blend amount of the polymer dispersant is less than 2 parts by mass, it may be difficult to obtain good pigment dispersion stability. On the other hand, when the blending amount of the polymeric dispersant exceeds 100 parts by mass, the developability of the formed film may be lowered.

As a solution containing a film-forming material used for preparing a pigment dispersion for a color filter, a solution of a film-forming polymer contained in conventionally known pigment dispersion for a color filter can be used. Examples of the liquid medium used for the liquid containing the film-forming material include an organic solvent, water, and a mixture of an organic solvent and water. In addition, conventionally known additives such as a dispersion aid, a smoothing agent, and an adhesion agent may be added to the pigment dispersion for a color filter according to necessity.

The amount of the pigment composition contained in the pigment colorant of the present invention is preferably 5 to 500 parts by mass, more preferably 50 to 250 parts by mass with respect to 100 parts by mass of the film forming material. As the liquid containing the film-forming material, a liquid containing a photosensitive film-forming material or a liquid containing a non-photosensitive film-forming material may be appropriately selected and used in accordance with the use. Specific examples of the liquid containing the photosensitive film-forming material include a liquid containing a photosensitive film-forming material used for an ultraviolet curable ink, an electron beam (curable) ink, and the like. Specific examples of the liquid containing the non-photosensitive film-forming material include varnishes used in printing inks such as relief ink, flat ink, gravure ink, and screen ink; Varnishes for use as permanent dry or baking paints; Varnish used for electrodeposition coating; And varnishes used in thermal transfer ribbons.

The pigment dispersion for a color filter is required to have a low viscosity as compared with a general dry paint or a baking paint while containing a pigment at a high concentration and having good dispersion of the pigment. Generally, even if the pigment concentration is from 5 to 20 mass%, it is required that the pigment is not agglomerated, its viscosity is about 5 to 20 mPa 占 퐏, and the storage stability is good. Therefore, when it is used for a color filter, the pigment dispersion of the present invention preferably satisfies the above viscosity condition. Preferably, the viscosity is 5 to 15 mPa · s, and the viscosity increase rate after standing for 1 month at 25 ° C. (after standing) is within 10%. If the viscosity is increased, it becomes difficult to produce a film with a constant film thickness.

Specific examples of photosensitive film-forming materials include photosensitive cyclic rubber-based resins, photosensitive phenolic resins, photosensitive polyacrylate resins, photosensitive polyamide resins, photosensitive polyimide resins, unsaturated polyester resins, polyester A photosensitive resin such as an acrylate resin, a polyepoxyacrylate resin, a polyurethane acrylate resin, a polyether acrylate resin, and a polyol acrylate resin. To the liquid containing these photosensitive resins, various monomers may be added as a reactive diluent.

When a photopolymerization initiator such as benzoin ether or benzophenone is added to a pigment colorant containing a photosensitive resin as a film forming material and milled by a conventionally known method, a photocurable photosensitive pigment dispersion can be obtained. When a thermal polymerization initiator is used instead of the photopolymerization initiator described above, a thermosetting pigment dispersion can be used.

Specific examples of the non-photosensitive film-forming material include a styrene- (meth) acrylate-based (co) polymer, a soluble polyamide-based resin, a soluble polyimide-based resin, a soluble polyamide- , A water-soluble salt of a styrene-maleic acid ester-based copolymer, a water-soluble salt of a (meth) acrylic acid ester- (meth) acrylic acid-based copolymer, and a water-soluble aminopolyester-based resin.

[Example]

Next, the present invention will be described in more detail with reference to examples and comparative examples. Hereinafter, "part" and "%" are based on mass unless otherwise specified.

<Preparation of pigment dispersant>

(Example I-1)

10 parts of 2,4-dihydroxyquinoline and 5 parts of sodium hydroxide were dissolved in 600 parts of water, and 14 parts of 1-aminoanthraquinone was diazotized by a conventional method, followed by coupling at 20 to 30 ° C for 4 hours . After filtration, washing with water and drying, 24 parts of an intermediate were obtained. 10 parts of the obtained intermediate was dissolved in 100 parts of 20% fuming sulfuric acid and reacted at 50 to 60 캜 for 5 hours. 12 parts of a yellowish brown pigment dispersant (I-A) represented by the following formula (I-A) was obtained by charging the mixture into iced water, followed by filtration, washing with water and drying.

(Example I-2)

120 parts of water was added to 50 parts of the paste (pigment dispersant (I-A) in 10 parts) of the pigment dispersant (I-A) obtained in Example I-1 and stirred at 20 to 30 ° C for 1 hour. 14 parts of tetrabutylammonium bromide was added and stirred for 1 hour, followed by filtration, washing with water and drying to obtain 14 parts of a yellowish brown pigment dispersant (I-B) represented by the following formula (I-B).

(Example I-3)

10.3 parts of a yellowish green pigment dispersant (IC) represented by the following formula (IC) was obtained in the same manner as in the above Example I-2 except that 14 parts of tetrabutylammonium bromide was replaced by 13 parts of aluminum sulfate 14-18 hydrate .

(Example I-4)

Except that 10 parts of 5-amino-2-benzimidazolidinone was used in place of 14 parts of 1-aminoanthraquinone to prepare a red pigment dispersant ( ID) of 12.4 parts was obtained.

(Example I-5)

Except that the paste of the pigment dispersant (ID) obtained in Example I-4 (the amount of pigment dispersant (ID): 9 parts) was used in place of the paste of the pigment dispersant (IA) , 13 parts of a red pigment dispersant (IE) represented by the following formula (IE) was obtained.

(Example I-6)

Except that the paste of the pigment dispersant (ID) obtained in Example I-4 (the amount of the pigment dispersant (ID): 9 parts) was used in place of the paste of the pigment dispersant (IA) , 9.1 parts of a red pigment dispersant (IF) represented by the following formula (IF) was obtained.

It was confirmed that the pigment dispersants (I-A) to (I-F) prepared had the intended compositions by mass analysis by elemental analysis of CHN and MALDI (abbreviation of matrix-assisted laser desorption ionization method). The results of elemental analysis for the pigment dispersants (I-A) to (I-F) are shown in Table I-1. As shown in Table I-1, a value close to a calculated value (theoretical value) was obtained for any of C, H, and N elements. Further, by S analysis, a value close to a calculated value (theoretical value) in which the number of substitution of the sulfonic acid group was &quot; 1 &quot; was obtained. As to the pigment dispersant (I-A), a peak of m / z = 475 was detected by mass spectrometry. The pigment dispersant (IA) measured by high performance liquid chromatography (column: YMCPack Pro C18, manufactured by Nippon Bunko Kogyo Co., Ltd.: MODEL 860-CO, YMC CO., LTD. ) Was 93%. Therefore, it was confirmed from the results of raw materials, elemental analysis, mass spectrometry, and high-performance liquid chromatography that the compound of the desired composition was obtained.

[Table I-1]

&Lt; Preparation of pigment compositions (I-1) to (I-12)

(Example I-7)

, 100 parts of PR254 (trade name: IRGAZIN RED L3660HD, manufactured by BASF), 5 parts of the pigment dispersant (IA) obtained in Example I-1, 600 parts of sodium chloride having an average particle diameter of 5 mu m and 150 parts of diethylene glycol, I put it in one kneader. Kneaded until a uniformly wet mass was produced in the kneader, the pressure lid was closed, and kneading was started while pressing the contents at a pressure of 6 kg / cm ² . The contents were milled for 4 hours while controlling the cooling temperature and the amount of cooling water so that the temperature of the contents was 40 to 45 占 폚 to obtain a milled product. The obtained wastes were put into 3,000 parts of 2% sulfuric acid aqueous solution heated at 80 占 폚, stirred for 1 hour, filtered and washed with water to remove sodium chloride and diethylene glycol. The filtration residue was dried in a hot-air dryer at 80 ° C for 24 hours to obtain a pigment composition (I-1).

(Examples I-8 to I-12)

Pigment compositions (I-2) to (I-6) were obtained in the same manner as in Example I-7 except that the pigment dispersants (I-B) to (I-F) were used in place of the pigment dispersant (I-A).

(Example I-13)

(I-7) was obtained in the same manner as in the above Example I-7 except that PR177 (trade name: PALIOGEN RED L4039, manufactured by BASF) was used instead of PR254.

(Examples I-14 to I-18)

Pigment compositions (I-8) to (I-12) were obtained in the same manner as in the above Example I-13 except that the pigment dispersants (I-B) to (I-F) were used in place of the pigment dispersant (I-A).

The combination of the pigment and the pigment dispersant used in preparing the pigment compositions (I-1) to (I-12) is shown in Table I-2.

[Table I-2]

Composition of pigment composition

<Preparation of pigment dispersion (pigment colorant for color filter (CF))>

(Example I-19)

An acrylic resin varnish having an average molecular weight of 12,000 and a solid content concentration of 40% was obtained by copolymerizing methacrylic acid / benzyl acrylate / styrene / hydroxyer acrylate in a molar ratio of 25/50/15/10 , And a pigment dispersion was prepared according to the following method. , 20 parts of the pigment composition (I-1), 17.4 parts of a basic polymer dispersant (trade name &quot; DISPERBYK-2001 &quot;, manufactured by Big-Chemie, solid content 46%) and 50 parts of propylene glycol- And 20 parts of methyl ether-2-acetate were mixed, premixed and dispersed using a horizontal bead mill to obtain a pigment colorant for CF (Example I-19).

(Examples I-20 to I-30)

20 to I-12 were prepared in the same manner as in Example I-19 except that the pigment compositions (I-2) to (I-12) were used in place of the pigment compositions (I- 30).

(Comparative Example I-1)

A composition containing PR254 not treated with a pigment dispersant was obtained in the same manner as in Example I-7, except that the pigment dispersant (I-A) was not used. A pigment colorant for CF (Comparative Example I-1) was obtained in the same manner as in Example I-19, except that the composition containing PR254 obtained above was used in place of the pigment composition (I-1).

(Comparative Example I-2)

(I-13) was obtained in the same manner as in Example I-7, except that the pigment dispersant (I-G) represented by the following formula (I-G) described in Patent Document 1 was used instead of the pigment dispersant (I-A). A pigment colorant for CF (Comparative Example I-2) was obtained in the same manner as in the above Example I-19 except that the pigment composition (I-13) obtained above was used in place of the pigment composition (I-1) .

(Comparative Example I-3)

A composition containing PR177 not treated with a pigment dispersant was obtained in the same manner as in Example I-13, except that the pigment dispersant (I-A) was not used. A pigment colorant for CF (Comparative Example I-3) was obtained in the same manner as in Example I-19, except that the composition containing PR177 obtained above was used in place of the pigment composition (I-1).

(Comparative Example I-4)

(I-14) was obtained in the same manner as in Example I-13, except that the pigment dispersant (I-H) represented by the following formula (I-H) described in Patent Document 1 was used instead of the pigment dispersant (I-A). A pigment colorant for CF (Comparative Example I-4) was obtained in the same manner as in the above Example I-19 except that the pigment composition (I-14) obtained above was used in place of the pigment composition (I-1) .

<Evaluation>

(1) fluidity (storage stability), (2) gloss of a colored surface, and (3) coloring property of the CF pigment colorants of Examples I-19 to I-30 and Comparative Examples I- (3) foreign matters in the coating film, and (4) contrast. Each evaluation method is shown below. The evaluation results are shown in Table I-3.

(1) Fluidity (storage stability)

The viscosity (mPa 占 퐏) of the pigment coloring agent for CF was measured immediately after preparation (initial) and at 25 占 폚 for one month (after standing) by using an E-type viscometer, The measurement conditions were temperature: room temperature (25 DEG C), and number of revolutions of the rotor: 6 rpm. In addition, &quot; viscosity after standing / initial viscosity (%) &quot; was calculated, and the obtained value was used to evaluate &quot; storage stability &quot; according to the following criteria.

○: "Viscosity after initialization / initial viscosity" is 110% or less

X: "Viscosity after initialization / initial viscosity" exceeds 110%

(2) Gloss of the front surface

Using a bar coater (thickness of winding wire: 0.45 mm), a pigment colorant for CF was transferred to a polypropylene film to form a color surface. The gloss of the formed color front surface was observed with the naked eye and observed with a gloss meter, and the &quot; gloss of the front surface &quot; was evaluated according to the following criteria. Further, it can be determined that the higher the glossiness of the color surface, the better.

◎: Very good

○: Good

X: Bad

(3)

A pigment colorant for CF was applied to a glass substrate using a spinner, dried at 90 DEG C for 2 minutes, and then heated at 270 DEG C for 30 minutes to form a coating film. Using a microscope, the surface (coated surface) of the formed coating film was observed at 200-fold magnification to check the presence or absence of foreign matter, and the "foreign matter in the coating film" was evaluated according to the following criteria.

◎: No foreign matter

○: Some foreign matter

×: There is foreign matter

(4) Contrast

A pigment colorant for CF was applied to a glass substrate using a spinner, dried at 90 DEG C for 2 minutes, and then heated at 230 DEG C for 30 minutes to form a coating film. Further, the speed of the spinner was changed to form three coating films. Brightness and darkness of a coated film formed by using a contrast meter (manufactured by i-System Co., Ltd.) were measured and the contrast (bright / dark brightness) was calculated. The coating film was colorimetrically measured using a spectrophotometer (trade name &quot; U-2000A &quot;, manufactured by Hitachi Seisakusho), and the chromaticity x was measured. An approximate straight line was drawn on the graph prepared by plotting the contrast for the chromaticity x and the contrast of the chromaticity x = 0.650 was read. The contrast ratio (%) of each example and the comparative example was calculated assuming that the contrast of the comparative example I-2 or the contrast of the comparative example I-4 was "100%". Then, using the obtained calculated values, "contrast" was evaluated according to the following criteria.

◎: 110% or more

○: 90% or more and less than 110%

×: less than 90%

[Table I-3]

As shown in Table I-3, the pigment colorants for CF of the Examples had low viscosity, good storage stability, good gloss of the color surface, and foreign matter , And it is also understood that the contrast is high. From the above, it is apparent that the pigment dispersant of the examples has an excellent effect.

In addition, the pigment compositions of the examples may be used in combination with printing inks such as offset inks; Various paints such as nitrocellulose lacquer and melamine alkyd paint; And a coloring agent for a synthetic resin such as a vinyl chloride resin. As a result, in either case, the pigment did not aggregate and showed good dispersibility. Recently, a pigment dispersant of the examples was used for the preparation of dry or wet toner for electrophotography, ink for inkjet recording, ink for thermal transfer recording, ink for writing instrument and the like, which are particularly required to be highly dispersible. As a result, excellent dispersibility was exhibited in any case.

<Preparation of pigment dispersant>

(Example II-1)

10 parts of 2,4-dihydroxyquinoline and 5 parts of sodium hydroxide were dissolved in 600 parts of water, and 14 parts of 1-aminoanthraquinone was diazotized by a conventional method, followed by coupling at 20 to 30 ° C for 4 hours . After filtration, washing with water and drying, 24 parts of an intermediate were obtained. After 10 parts of the obtained intermediate was dissolved in 100 parts of chlorosulfonic acid, 10 parts of thionyl chloride was added and the mixture was reacted at 50 to 60 DEG C for 5 hours. After cooling, the mixture was poured into ice water, filtered and washed with ice water to obtain a water dispersion of chlorosulfonylated product. The aqueous paste of the chlorosulfonylated product thus obtained was stirred and dispersed in a mixture of 200 parts of water and 100 parts of ice, and 7 parts of N, N-diethylaminopropylamine was added. The mixture was stirred at 20 to 30 ° C for 5 hours and reacted by heating at 60 to 70 ° C for 1 hour. After completion of the reaction, the resultant was filtered, washed with water and dried to obtain 14 parts of a yellowish brown pigment dispersant (II-A) represented by the following formula (II-A).

(Example II-2)

(II-B) was obtained in the same manner as in Example II-1 except that 8 parts of N- (3-aminopropyl) cyclohexylamine was used instead of 7 parts of N, N-diethylaminopropylamine 15 parts of a yellowish brown pigment dispersant (II-B) was obtained.

(Example II-3)

Except that 11 parts of N, N, N ", N" -tetraethyldiethylenetriamine was used instead of 7 parts of N, N-diethylaminopropylamine in the same manner as in Example II- 16 parts of a yellowish brown pigment dispersant (II-C) represented by the following formula (II-C).

(Example II-4)

Except that 10 parts of 5-amino-2-benzimidazolidinone was used in place of 14 parts of 1-aminoanthraquinone, the red pigment represented by the following formula (II-D) 15 parts of dispersant (II-D) were obtained.

(Example II-5)

Except that 10 parts of 5-amino-2-benzimidazolidinone was used in place of 14 parts of 1-aminoanthraquinone, and 10 parts of N- (3-aminopropyl) cyclo 16 parts of a red pigment dispersant (II-E) represented by the following formula (II-E) was obtained in the same manner as in the above Example II-1 except that 10 parts of hexylamine was used.

(Example II-6)

Except that 10 parts of 5-amino-2-benzimidazolidinone was used instead of 14 parts of 1-aminoanthraquinone used in Example II-1 and 10 parts of N, N-diethylaminopropylamine was used instead of 7 parts of N, N- (II-F) 17 (II-F) represented by the following formula (II-F) was obtained in the same manner as in Example II-1, except that 14 parts of N, N ", N "- tetraethyldiethylenetriamine I got wealth.

It was confirmed that the prepared pigment dispersants (II-A) to (II-F) had a desired composition by mass analysis by elemental analysis of CHN and MALDI (abbreviation of matrix-assisted laser desorption ionization method). The results of elemental analysis for the pigment dispersants (II-A) to (II-F) are shown in Table II-1. As shown in Table II-1, a value close to a calculated value (theoretical value) was obtained for any of C, H, and N elements. Further, by S analysis, a value close to the calculated value (theoretical value) in which the number of substitution of the sulfonamide group was &quot; 1 &quot; was obtained. Further, with respect to the pigment dispersant (II-A), a peak at m / z = 587 was detected by mass spectrometry. The purity of the pigment dispersant (II-A) was 91% as measured using high performance liquid chromatography (Nippon Bunko Kogyo Co., Ltd., MODEL860-CO, WYMERSHACCHE column: YMCPack Pro C18). Therefore, it was confirmed from the results of raw materials, elemental analysis, mass spectrometry, and high-performance liquid chromatography that the compound of the desired composition was obtained.

[Table II-1]

&Lt; Preparation of pigment compositions (II-1) to (II-12)

(Example II-7)

, 12 parts of the pigment dispersant (II-A) obtained in Example II-1, 600 parts of sodium chloride having an average particle diameter of 5 mu m, and 150 parts of diethylene glycol were mixed with 100 parts of PR254 (trade name: IRGAZIN RED L3660HD, Was put in a kneader equipped with a stirrer. Kneaded until a uniformly wet mass was produced in the kneader, the pressure lid was closed, and kneading was started while pressing the contents at a pressure of 6 kg / cm ² . The contents were milled for 4 hours while controlling the cooling temperature and the amount of cooling water so that the temperature of the contents was 40 to 45 占 폚 to obtain a milled product. The obtained wastes were put into 3,000 parts of a 2% sulfuric acid aqueous solution heated at 80 占 폚, stirred for 1 hour, filtered and washed with water to remove sodium chloride and diethylene glycol. The filtration residue was dried in a hot-air dryer at 80 ° C for 24 hours to obtain a pigment composition (II-1).

(Examples II-8 to II-12)

(II-2) to (II-6) were obtained in the same manner as in Example II-7 except that the pigment dispersants (II-B) to (II- &Lt; / RTI &gt;

(Example II-13)

Pigment composition (II-7) was obtained in the same manner as in Example II-7, except that PR177 (trade name: PALIOGEN RED L4039, available from BASF) was used instead of PR254.

(Examples II-14 to II-18)

(II-8) to (II-12) were obtained in the same manner as in Example II-13 except that the pigment dispersants (II-B) to (II- .

The combination of the pigment and the pigment dispersant used in preparing the pigment compositions (II-1) to (II-12) is shown in Table II-2.

[Table II-2]

<Preparation of pigment dispersion (pigment colorant for color filter (CF))>

(Example 19)

Acrylic resin varnish having an average molecular weight of 12,000 and a solid content concentration of 40%, obtained by copolymerizing methacrylic acid / benzyl acrylate / styrene / hydroxy acrylate at a molar ratio of 25/50/15/10, To prepare a pigment dispersion. 15 parts of an acrylic resin varnish, 20 parts of a pigment composition (II-1), 15.4 parts of an acidic polymer pigment dispersant (trade name: DISPERBYK-110, manufactured by Big Chemicals Co., solid content 52%), Acetate and 20 parts of monomethyl ether-2-acetate were mixed and premixed and dispersed using a horizontal bead mill to obtain a pigment colorant for CF (Example II-19).

(Examples II-20 to II-30)

(II-20 to II-12) were prepared in the same manner as in Example II-19 except that the pigment compositions (II-2) to 30).

(Comparative Example II-1)

A composition containing PR254 not treated with a pigment dispersant was obtained in the same manner as in Example II-7, except that the pigment dispersant (II-A) was not used. A pigment colorant for CF (Comparative Example II-1) was obtained in the same manner as in Example II-19 except that the composition containing PR254 obtained above was used in place of the pigment composition (II-1).

(Comparative Example II-2)

Except that the pigment dispersant (II-G) represented by the following formula (II-G) described in Patent Document 1 was used in place of the pigment dispersant (II-A) -13). A pigment colorant for CF (Comparative Example II-2) was obtained in the same manner as in the above Example II-19 except that the pigment composition (II-13) obtained above was used in place of the pigment composition (II-1) .

(Comparative Example II-3)

A composition containing PR177 not treated with a pigment dispersant was obtained in the same manner as in Example II-13, except that the pigment dispersant (II-A) was not used. A pigment colorant for CF (Comparative Example II-3) was obtained in the same manner as in Example II-19, except that the composition containing PR177 obtained above was used in place of the pigment composition (II-1).

(Comparative Example II-4)

Except that the pigment dispersant (II-H) represented by the following formula (II-H) described in Patent Document 2 was used in place of the pigment dispersant (II-A) -14). A pigment colorant for CF (Comparative Example II-4) was obtained in the same manner as in the above Example II-19 except that the pigment composition (II-14) obtained above was used in place of the pigment composition (II-1) .

<Evaluation>

(1) fluidity (storage stability), (2) gloss of a colored surface, (3) glossiness of the surface of a coloring sheet, (2) Foreign matter, and (4) contrast. Each evaluation method is shown below. The evaluation results are shown in Table II-3.

(1) Fluidity (storage stability)

The viscosity (mPa 占 퐏) of the pigment coloring agent for CF was measured immediately after preparation (initial) and at 25 占 폚 for one month (after standing) by using an E-type viscometer, The measurement conditions were temperature: room temperature (25 DEG C), and number of revolutions of the rotor: 6 rpm. In addition, &quot; viscosity after standing / initial viscosity (%) &quot; was calculated, and the obtained value was used to evaluate &quot; storage stability &quot; according to the following criteria.

○: "Viscosity after initialization / initial viscosity" is 110% or less

X: "Viscosity after initialization / initial viscosity" exceeds 110%

(2) Gloss of the front surface

Using a bar coater (thickness of winding wire: 0.45 mm), a pigment colorant for CF was transferred to a polypropylene film to form a colored surface. The gloss of the formed color front surface was observed with the naked eye and observed with a gloss meter, and the &quot; gloss of the front surface &quot; was evaluated according to the following criteria. Further, it can be determined that the higher the glossiness of the color surface, the better.

◎: Very good

○: Good

X: Bad

(3)

A pigment colorant for CF was applied to a glass substrate using a spinner, dried at 90 DEG C for 2 minutes, and then heated at 270 DEG C for 30 minutes to form a coating film. Using a microscope, the surface (coated surface) of the formed coating film was observed at 200-fold magnification to check the presence or absence of foreign matter, and the "foreign matter in the coating film" was evaluated according to the following criteria.

◎: No foreign matter

○: Some foreign matter

×: There is foreign matter

(4) Contrast

A pigment colorant for CF was applied to a glass substrate using a spinner, dried at 90 DEG C for 2 minutes, and then heated at 230 DEG C for 30 minutes to form a coating film. Further, the speed of the spinner was changed to form three coating films. Brightness and darkness of a coating film formed using a contrast meter (i-System Co., Ltd.) were measured, and the contrast (bright / dark brightness) was calculated. Further, the coating film was colorimetrically measured using a spectrophotometer (trade name &quot; U-2000A &quot;, manufactured by Hitachi, Ltd.), and the chromaticity x was measured. An approximate straight line was drawn on the graph prepared by plotting the contrast for the chromaticity x and the contrast of the chromaticity x = 0.650 was read. The contrast ratio (%) of each example and comparative example was calculated assuming that the contrast of the comparative example II-2 or the contrast of the comparative example II-4 was "100%". Then, using the obtained calculated values, "contrast" was evaluated according to the following criteria.

◎: 110% or more

○: 90% or more and less than 110%

×: less than 90%

[Table II-3]

As shown in Table II-3, the pigment colorants for CF of the Examples had low viscosity, good storage stability, good glossiness of the color surface, and foreign matter , And it is also understood that the contrast is high. From the above, it is apparent that the pigment dispersant of the examples has an excellent effect.

In addition, the pigment compositions of the examples may be used in combination with printing inks such as offset inks; Various paints such as nitrocellulose lacquer and melamine alkyd paint; And a coloring agent for a synthetic resin such as a vinyl chloride resin. As a result, in either case, the pigment did not aggregate and showed good dispersibility. Recently, a pigment dispersant of the examples was used for the preparation of dry or wet toner for electrophotography, ink for inkjet recording, ink for thermal transfer recording, ink for writing instrument and the like, which are particularly required to be highly dispersible. As a result, excellent dispersibility was exhibited in any case.

The pigment dispersant of the present invention can be used in various fields such as printing ink (offset ink, gravure ink and the like), various paints, plastics, pigment printing agents, dry or wet toner for electrophotography, ink for inkjet recording, ink for thermal transfer recording, , Ink for writing tools, etc., and is expected to be used.

Claims (6)

A pigment dispersant which is a compound represented by any one of the following formulas (IA) to (IF) and (II-A) to (II-F)

A pigment composition comprising a pigment and the pigment dispersant according to claim 1. 3. The method of claim 2,
Wherein the blending amount of the pigment dispersant relative to 100 parts by mass of the pigment is 0.5 to 40 parts by mass. A pigment colorant comprising the pigment composition according to claim 2 or 3 and a film-forming material. 5. The method of claim 4,
Pigment coloring agent for image display, image recording, printing ink, writing ink, plastic, pigment printing, or paint. 5. The method of claim 4,
Pigment coloring agent for color filter.