TWI535484B - Pigment dispersants, pigment compositions, and pigment colorants - Google Patents

Description

Pigment dispersant, pigment composition, and pigment colorant

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

It is generally difficult to mix and disperse pigments (particles) in a stable state into a vehicle such as a coating, a gravure ink, or a lithographic ink. For example, fine pigment particles temporarily dispersed in a vehicle tend to aggregate in the medium. The pigment particles produce agglomerated agents which have a problem of increased viscosity. Further, when a vehicle in which agglomerated pigment particles are dispersed is used, various problems such as a decrease in the coloring power of the ink or the paint or a decrease in the gloss of the coating film are likely to occur.

Further, a color filter for producing a liquid crystal color display or a photographic element or the like is produced by using a pigment dispersion liquid, for example, by the following method. First, a pigment dispersion for color filters (color filter (CF)) obtained by dispersing three colors of red (R), green (G), and blue (B) into a photosensitive resin liquid Use pigment colorants). These CF pigment coloring agents are applied to the color filter substrate by a spin coating method to form a colored film. Next, the formed color film is exposed through a mask, and then developed to pattern the colored film, and a color filter can be obtained by forming a desired pixel on the substrate.

As the pigment for producing a color filter, there are a green pigment, a red pigment, and a blue pigment. As a green pigment, for example, it is usually C.I. Pigment Green (hereinafter, It is described as "PG") 36, phthalocyanine green such as PG7 or PG58. The red pigment is, for example, a diketopyrrolopyrrole red such as C.I. pigment red (hereinafter referred to as "PR") 254; an anthraquinone red such as PR177; and an azo red such as PR242. Further, as the blue pigment, for example, phthalocyanine blue such as C.I. Pigment Blue (hereinafter referred to as "PB") 15:6 is usually used.

Further, since the color tone of the pigment differs from the color characteristics required for the liquid crystal display, a pigment for complementary color is used in combination. For example, as the green pigment and the red pigment, a small amount of a yellow pigment such as C.I. Pigment Yellow (hereinafter referred to as "PY") 138, PY139 or PY150 is used as a pigment for complementary color. Further, as the blue pigment, a small amount of a violet pigment such as C.I. Pigment Violet (hereinafter referred to as "PV") 23 is used as a pigment for complementary color. Further, in order to form a good pixel of the color filter, it is preferable that the main pigment and the complementary color pigment are present in a uniform state in the pigment pigment for CF.

However, in the case of using a pigment in combination, it is of course difficult to disperse the above pigment in a dispersion medium such as a photosensitive resin liquid using a usual dispersing machine, and only a pigment dispersion liquid in which the dispersion state of the pigment is not good can be obtained. The color filter of the color filter formed using the pigment pigment for CF which is not in a good dispersion state of the pigment is insufficient in light transmittance, and the light transmittance of the pixel as the color filter is insufficient. That is, there is a case where the pigment pigment for CF obtained by dispersing a pigment using a usual dispersing machine is insufficient as a coloring agent for forming a pixel of a color filter.

On the other hand, as for the photosensitive resin for photoresist which is a dispersion medium of a pigment, an acrylic polymer having a higher acid value is mainly used so that the developed color film can be easily developed by using an alkaline aqueous solution as a developing solution. . However, a pigment coloring agent containing the above pigment and an acrylic polymer having a high acid value has problems in that the pigment is easily aggregated and the viscosity is liable to become high. Further, since the agglutination of the pigment progresses over time to cause sticking, there are also problems such as low storage stability. Furthermore, if the viscosity is high, When the pigment is agglomerated to exhibit a viscous pigment coloring agent and a color filter is to be produced, there is a case where the central portion of the coloring film before the exposure is convex. Therefore, there is a problem that unevenness or density difference occurs in the pixels located at the central portion of the substrate and the pixels located in the peripheral portion. Moreover, this problem becomes more apparent when it is desired to make a larger color filter.

Therefore, for the pigment coloring agent (photoresist) for CF, it is required that even if the pigment is contained at a high concentration, the pigment is dispersed to a photosensitive resin as a dispersion medium, and the viscosity is lower than that of a normal dry paint or a sintered paint. . In general, it is required that even if the pigment concentration is 5 to 20% by mass, the pigment does not aggregate, the viscosity is about 5 to 20 mPa·s, and the storage stability is good.

In order to satisfy the above requirements, a method of adding a pigment derivative as a dispersing agent for a pigment, a method of treating a pigment with a pigment derivative, and the like have been proposed. Specifically, when a diketopyrrolopyrrole red such as PR254 is used as a pigment, a substituted derivative of a diketopyrrolopyrrole is used as a pigment dispersant. In the case where lanthanide red such as PR177 is used as the pigment, a substituted derivative of ruthenium is used as the pigment dispersant (for example, refer to Patent Documents 1 to 3).

[Previous Technical Literature] [Patent Literature]

[Patent Document 1] Japanese Patent Laid-Open Publication No. 2001-240780

[Patent Document 2] Japanese Patent Laid-Open Publication No. 2001-174616

[Patent Document 3] Japanese Patent Laid-Open Publication No. 2009-029886

In recent years, it has been desired 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, with the conventional techniques proposed in Patent Documents 1 to 3, it is difficult to obtain a pigment coloring agent capable of producing a color filter satisfying the above properties. Further, the pigment coloring agent obtained by a conventional technique is not limited to the color filter, and is expected to be improved because a foreign matter is generated in the formed coating film (colored film).

The present invention has been made in view of the problems of the prior art, and an object thereof is to provide a fluid property which can remarkably improve an ink or a coating material containing a pigment, and can prevent aggregation of particles of a pigment, and can prevent foreign matter from being produced. A pigment dispersant that produces a colored article that exhibits excellent gloss and clarity. Further, an object of the present invention is to provide a pigment composition obtained by using the above pigment dispersant and a pigment colorant.

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

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

Further, according to the present invention, the pigment composition shown below is provided.

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

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

Further, according to the present invention, a pigment coloring agent shown below is provided.

[4] A pigment coloring agent comprising the pigment composition according to the above [2] or [3], and a film forming material.

[5] The pigment coloring agent according to [4] above, which is used for image display, image recording, printing ink, ink for writing, plastic, pigment printing, or paint.

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

The pigment dispersant of the present invention is capable of remarkably improving the fluidity of an ink or a coating material containing a pigment, and preventing aggregation of particles of the pigment, and can be manufactured to prevent generation of foreign matter, and exhibit excellent gloss and clarity. Coloring items. Therefore, the pigment dispersant of the present invention can be preferably used for printing inks such as lithographic inks or gravure inks, various coatings, plastics, pigment printing agents, dry or wet toner for electronic photographs, inks for inkjet recording, and heat transfer. A medium used for printing ink for recording, a resist for color filters, ink for writing instruments, and the like. Moreover, when the pigment dispersing agent of the present invention is used, it is possible to provide a pigment composition and a pigment coloring agent which can significantly improve the fluidity of various coating materials and the like, prevent aggregation of pigment particles, and form a coloring film which can effectively prevent the formation of foreign matter. Further, the pigment coloring agent of the present invention is difficult to produce tackiness or gelation upon storage, and can produce a coloring matter having excellent gloss and clarity. Therefore, the pigment coloring matter of the present invention is particularly preferable as a pigment coloring agent for a color filter or the like.

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

<Pigment Dispersant>

Hereinafter, the details of the present invention will be described by way of examples of preferred embodiments. One of the main features of the pigment dispersant of the present invention is that it is a compound represented by the following formula (I-1), a quaternary ammonium salt of the compound, an amine salt of the compound, or a metal salt of the compound. Further, one of the main features of the pigment dispersant of the present invention is that it is a compound represented by the following formula (II-1). The pigment dispersant of the present invention having the above characteristics has excellent affinity for various pigments, and can be preferably used as a pigment dispersant for dispersing various pigments, whether organic or inorganic. Further, the pigment dispersant of the present invention has an excellent pigment dispersion effect, and thus can be used as a material for preparing a pigment colorant for various uses.

In the formula (I-1), X represents a residue of an aromatic compound or a heterocyclic compound which may have a substituent. Further, the bonding site of "N=N-" in the formula (I-1) is an aromatic ring of the above aromatic compound or a heterocyclic ring of the above heterocyclic compound. Further, 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 formula (II-1), X represents a residue of an aromatic compound or a heterocyclic compound which may have a substituent. Further, the bonding site of "N=N-" in the formula (II-1) is an aromatic ring of the above aromatic compound or a hetero ring of the above heterocyclic compound. Further, Y in the formula (II-1) represents a reactive residue of an aliphatic amine, an alicyclic amine or a heteroalicyclic amine having a basic nitrogen atom and having 2 to 30 carbon atoms. Further, the bonding site with "O ₂ S-" in the formula (II-1) is a nitrogen atom of the above aliphatic amine, the above alicyclic amine or the above heteroalicyclic amine. Further, in the general formula (II-1), n represents a number of 0.2 to 3. The average introduction number of the general formula (II-1) are indicated with an mean of n "-SO ₂ Y 'represents a group of the formula (1) compound.

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 by using the pigment dispersant of the present invention are less likely to cause sticking or gelation during storage, and it is difficult to generate foreign matter in the coating film formed by using these. 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).

Further specific examples of the pigment dispersant of the present invention include the following formulae (I-1-1) to (I-1-8) and the following formula (II-1-1) to (II-1) -8) indicated compound Wait.

The compound (pigment dispersant) represented by the formula (I-1) can be synthesized, for example, in the following manner. First, an aromatic compound or a heterocyclic compound having an amine group such as 1-aminoindole is diazotized by a conventional method, and then coupled with 2,4-dihydroxyquinoline to obtain an intermediate. When a known sulfonating agent such as fuming sulfuric acid is used and the obtained intermediate is sulfonated by a usual method, a compound (pigment dispersing agent) represented by the formula (I-1) can be obtained. Further, the pigment dispersant of the present invention has a possibility of containing a small amount of unreacted raw materials, but may contain an unreacted original as long as the effect of the present invention can be obtained. material.

The compound (pigment dispersant) represented by the formula (II-1) can be synthesized, for example, in the following manner. First, an aromatic compound or a heterocyclic compound having an amine group such as 1-aminoindole is diazotized by a conventional method, and then coupled with 2,4-dihydroxyquinoline to obtain an intermediate. Next, in chlorosulfonic acid, the intermediate obtained at 50 to 60 ° C is chlorosulfonated, and then precipitated into ice water, filtered and washed with ice water to obtain a water paste of sulfonium chloride. When the obtained sulfonium chloride is reacted with an amine compound having a basic nitrogen atom such as N,N-diethylaminopropylamine in water at 50 to 60 ° C, a general formula (II) can be obtained. -1) a compound (pigment dispersant). Further, the pigment dispersant of the present invention may contain a small amount of unreacted raw materials and by-products such as a sulfonate. However, if the effects of the present invention are obtained, the unreacted raw materials and by-products may be slightly contained.

Specific examples of the aromatic compound and the heterocyclic compound having an amine group which can be used in the above synthesis method include aniline, toluidine (o-, m- or p-), 2,4-dimethylaniline, and 3,4. -xylamine, 2-methoxy-5-methylaniline, methoxyaniline (o-, m- or p-), aminophenol (o-, m- or p-), o-amine benzoic acid, p-aminobenzoic acid, Nitroaniline (o-, m- or p-), chloroaniline (o-, m- or p-), 2,5-dichloroaniline, 3,4-dichloroaniline, 3,5-dichloroaniline, 2,3,4 -trichloroaniline, 2,4,5-trichloroaniline, 2,4,6-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-nitrobenzonitrile, 1-naphthylamine, 3-amino-9- Ethyl carbazole, 2-aminopyridine, 3-aminopyridine, 4-aminopyridine, 2-aminothiazole, 2-amino-5-nitrothiazole, 2-aminobenzothiazole, 2- Amino-6-methoxybenzothiazole, 1-aminopurine, 2-aminopurine 5-amino-2-benzimidazolidinone, 4-aminophthalimide, 4-amino-N-methylphthalimide, o-(phenylsulfonyl) Aniline, 2-ethylsulfonyl-5-methoxyaniline, 2-ethylsulfonyl-5-trifluoromethylaniline, 4-benzylsulfonyl-o-oxyaniline, 3-amino -N,N-diethyl-4-methoxybenzenesulfonamide, 3-aminobenzamide, 3-amino-4-methylbenzamide, 3-amino-4-methyl Oxybenzamide, 4-aminobenzamide, 2-amino-4,4'-dichlorodiphenyl ether, 4-benzylideneamine-2,5-dimethoxyaniline, 9 - Amino acridine, 6-aminocarbazole, and the like. Among these, 1-aminoindole, 5-amino-2-benzimidazolidinone is preferred.

Further, examples of the amine which forms an amine salt with the sulfonic acid group in the formula (I-1) include (mono, di or tri)alkylamines, substituted or unsubstituted alkylenediamines. Classes, alkanolamines, alkyl ammonium chlorides, and the like. Among them, a quaternary ammonium salt is preferred. Further, examples of the metal forming a metal salt with the sulfonic acid group in the formula (I-1) include alkali metals such as Li, Na, and K; and polyvalent amounts of Ca, Ba, Al, Mn, Sr, Mg, and Ni. Metal, etc.

Further, specific examples of the amine compound having a basic nitrogen atom include N,N-dimethylaminomethylamine, N,N-diethylaminomethylamine, and N,N-dipropyl. Aminomethylamine, N,N-dibutylaminomethylamine, N,N-dimethylaminoethylamine, N,N-diethylaminoethylamine, N,N- Dipropylaminoethylamine, N,N-dibutylaminoethylamine, N,N-dimethylaminopropylamine, N,N-diethylaminopropylamine, N, N-dipropylaminopropylamine, N,N-dimethylaminobutylamine, N,N-diethylaminobutylamine, N,N-dipropylaminobutylamine, N,N-Dibutylaminobutylamine, N,N-dimethylamino laurylamine, N,N-diethylaminolaurylamine, N,N-dibutylamine lauryl Amine, N,N-dimethylaminostearylamine, N,N-diethylaminostearylamine, N,N-diethanolylaminoethylamine, N,N-diethanol Aminopropylamine, N-(3-aminopropyl)cyclohexylamine, N-(3-aminopropyl) phenyl, 1-(3-aminopropyl)-2-methylpiperidine, N-Aminopropylpyrrolidine, N,N-diethylaminoethoxypropylamine, N,N,N",N"-tetramethyldiethylidene Amine, N, N, N", N"-tetraethyl diethylidene triamine, N, N, N", N"-tetrakis (n-propyl) di-ethyltriamine, N, N, N ",N"-tetrakis(isopropyl)diethylideneamine, N,N,N",N"-tetrakis(n-butyl)diethylidene, N,N,N",N" -tetrakis(isobutyl)diethylideneamine, N,N,N",N"-tetrakis(t-butyl)diethylideneamine,3,3'-iminobis(N, N-dimethylpropylamine), 3,3'-iminobis(N,N-diethylpropylamine), 3,3'-iminobis(N,N-di(n-propyl) Propylamine), 3,3'-iminobis(N,N-di(n-butyl)propylamine), 3,3'-iminobis(N,N-di(isobutyl) Propylamine), 3,3'-iminobis(N,N-di(t-butyl)propylamine), 3,3'-iminobis(N,N-dimethyl Propylamine), 2,9-dimethyl-2,5,9-triazanonane, 2,10-dimethyl-2,10-triazanonane, 2,12-dimethyl -2,6,12-triazatridecane, 2,12-dimethyl-2,5,12-triazatridecane, 2,16-dimethyl-2,9,16-three Azaheptadecane, 3-ethyl-10-methyl-3,6,10-triazaundecane, 5,13-di(n-butyl)-5,9,13-triaza-deca Heptane, bis(2-pyridylmethyl)amine, bis(3-pyridylmethyl)amine, and the like. Among 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, and examples thereof include the methods of use shown below. Regardless of the method, the target pigment dispersion effect can be obtained.

(1) The pigment and the 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 into the vehicle.

(2) The pigment and the pigment dispersant are separately added to a vehicle or the like at a predetermined ratio to disperse the pigment into the vehicle.

(3) After the pigment and the pigment dispersant are separately dispersed in a vehicle or the like, the obtained dispersion liquid is mixed at a predetermined ratio to disperse the pigment into the vehicle.

(4) adding a pigment dispersant to a predetermined ratio to disperse a pigment to a vehicle or the like The dispersion is obtained to disperse the pigment into the vehicle.

In the above methods (1) to (4), it is preferred to add a counter ion group having an ionic group in the compound (pigment dispersant) represented by the formula (I-1) (relative ionic group) The polymer dispersant disperses the pigment. It is particularly preferable to use the polymer dispersant having a relatively ionic group in the method of the above (1) or (2) to disperse the pigment.

<Pigment Composition>

The pigment composition of the present invention contains a pigment and the above pigment dispersant. The blending amount of the pigment dispersant with respect to 100 parts by mass of the pigment is preferably 0.5 to 40 parts by mass, and more preferably 1 to 20 parts by mass. When the blending amount of the pigment dispersant is less than the above range, there is a case where the effect of the target dispersing agent cannot be sufficiently obtained. On the other hand, when the amount of the pigment dispersant is more than the above range, the effect of the dispersant is at the apex, and the effect of the above is not expected, and the material cost is improved, which is disadvantageous in terms of productivity. Further, in a coating or ink using a pigment composition containing such a pigment dispersant excessively, there is also a case where the physical properties of the vehicle are lowered; or the color of the pigment is large due to the color of the pigment dispersant itself. change.

Specific examples of the pigment which obtains an effective dispersing effect by using the pigment dispersant of the present invention include a soluble, insoluble azo pigment, a high molecular weight azo pigment, a phthalocyanine pigment, a quinophthalone pigment, and an anthraquinone pigment. , Diketopyrrolopyrrole pigment, quinacridone pigment, methine-azo methine pigment, perylene pigment, piconone pigment, isoindolinone pigment, isoporphyrin pigment, metal Complex pigments, etc. Among these, particularly in the case of a pigment having a reddish hue, a more remarkable effect can be obtained, which is preferable. As such a pigment having a red hue, it is preferably as two PR254 of ketopyrrolopyrrole pigment and PR177 as an anthraquinone pigment.

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

(1) A method of mixing a powder of a pigment with a powder of a pigment dispersant without using a disperser.

(2) A method of mechanically mixing a pigment and a pigment dispersant by various dispersers such as a kneader, a roll, a pulverizer, and a transverse bead mill.

(3) A method of adding and mixing a liquid in which a pigment dispersant is dissolved or finely dispersed in a suspension of a pigment aqueous or organic solvent to uniformly deposit a pigment dispersant 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 then co-precipitated by a poor solvent such as water.

The properties of the pigment dispersant for preparing the pigment composition may be any one of a solution, a slurry, a paste, and a powder. The desired effect can be obtained in the case of using a pigment dispersant of any trait.

<Pigment Colorant>

The pigment coloring agent of the present invention contains the above pigment composition and a film forming material. The pigment coloring agent of the present invention can be obtained, for example, by forming the finely divided pigment composition, a resin selected from a resin ((co)polymer), an oligomer, or a monomer selected according to the use thereof. The materials are mixed. The pigment coloring agent of the present invention can be used for image display, image recording, printing ink, ink for notes, plastic, and pigment It is used in a wide range of fields for coloring agents such as printing and dyeing. In particular, as an image display material in which the transparency of the colored pixel becomes a problem, a pigment coloring agent for a color filter is preferable. Of course, the pigment coloring agent of the present invention is also useful as a material for image recording agents such as dry or wet toner for electronic photographs, ink for inkjet recording, electroplating recording liquid, ink for thermal transfer recording, and ink for writing instruments. These materials for image recording agents are used in various image recording methods such as an inkjet recording method, a plating recording method, and an electrophotographic method. When the pigment coloring agent of the present invention is used, a material for an image recording agent which can provide a high-quality image can be prepared regardless of the image recording method.

In the following, the pigment coloring agent (color filter (CF) pigment coloring agent) as a coloring agent for image display is exemplified as a representative example, and the pigment coloring agent of the present invention will be described in further detail. When preparing a pigment dispersion liquid (photoresist) for a color filter, the above pigment composition is first added to a liquid containing a film forming material and premixed. Next, as long as the dispersion treatment is carried out, a pigment dispersion liquid for a color filter can be obtained. More specifically, a pigment composition obtained by uniformly grinding using a dispersion medium such as a vertical media disperser, a transverse media disperser, or a ball mill is added and mixed to a liquid containing a film-forming material, whereby color can be obtained. A pigment dispersion for a filter. Further, a solution obtained by dissolving a pigment and a pigment dispersant in sulfuric acid or the like and water are mixed, and a pigment composition containing a pigment and a pigment dispersant is precipitated as a solid solution or an eutectoid and separated. In other words, it is convenient to add the separated pigment composition to a liquid containing a film forming material or a polymer dispersing agent, and then mix it, and then grind and disperse it by using a horizontal wet disperser (bead mill) such as a sand mill. A pigment dispersion for a color filter can also 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. Pigment coloring agent of the invention The surface of the pigment is treated with an acidic pigment dispersant represented by the formula (1). Therefore, a pigment dispersion liquid for a color filter having a lower viscosity and a higher contrast can be obtained by containing a basic polymer dispersant. Further, when an acidic polymer dispersant is contained, the pigment aggregates and the pigment colorant tends to be viscous.

As the polymer dispersant, a known dispersant can be used. Further, specific examples of the basic polymer dispersant include the following product names: DISPERBYK-160, DISPERBYK-161, DISPERBYK-162, DISPERBYK-163, DISPERBYK-164, DISPERBYK-166, DISPERBYK-171, DISPERBYK-182, DISPERBYK-184, DISPERBYK-2000, DISPERBYK-2001, DISPERBYK-2070, DISPERBYK-2150 (above BYK-Chemie); EFKA-44, EFKA-46, EFKA-47, EFKA-48, EFKA -4010, EFKA-4015, EFKA-4020, EFKA-4050, EFKA-4055, EFKA-4060, EFKA-4300, EFKA-4330, EFKA-4400, EFKA-4406, EFKA-4510, EFKA-4800 (above BASF) Manufactured by the company; SOLSPERS-24000, SOLSPERS-32550, NBZ-4204/10 (above is Lubrizol); Hinoact T-6000, Hinoact T-7000, Hinoact T-8000 (above is manufactured by Chuanyan Precision Chemical Co., Ltd.); Ajisper PB-821, Ajisper PB-822, Ajisper PB-823 (the above is manufactured by Ajinomoto Precision Technology Co., Ltd.).

Further, specific examples of the basic polymer dispersant include the following product names: KF-10000 (manufactured by Kasei Precision Chemical Co., Ltd.); alpha resin SA-300 (manufactured by Alpha Chemical Research Co., Ltd.); DISPERBYK-110 , DISPERBYK-111, DISPERBYK-180 (above is BYK-Chemie); SOLSPERS-41000 (manufactured by Lubrizol); Ajisper PA-111 (Ajinomoto) Made by precision technology company).

The amount of the polymer dispersant to be added is preferably from 2 to 100 parts by mass, more preferably from 10 to 50 parts by mass, per 100 parts by mass of the pigment. When the 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 amount of the polymer dispersant is more than 100 parts by mass, the developability of the formed film may be lowered.

As the liquid containing the film forming material for preparing the pigment dispersion liquid for color filters, a solution of a film-forming polymer contained in a conventionally known pigment dispersion liquid for color filters can be used. Moreover, examples of the liquid medium used for the liquid containing the film forming material include an organic solvent, water, and a mixed liquid of an organic solvent and water. Further, in the pigment dispersion liquid for a color filter, a conventionally known additive such as a dispersing aid, a smoothing agent, or a blocking agent may be added as needed.

The amount of the pigment composition contained in the pigment coloring matter of the present invention is preferably 5 to 500 parts by mass, and more preferably 50 to 250 parts by mass, per 100 parts by mass of the film forming material. Moreover, 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 can be appropriately selected depending on the application. Specific examples of the liquid containing the photosensitive film forming material include a liquid containing a photosensitive film forming material such as an ultraviolet curable ink or an electron beam curable ink. Further, specific examples of the liquid containing the non-photosensitive film forming material include varnishes for printing inks such as relief ink, lithographic ink, gravure ink, and screen printing ink; varnishes for drying at room temperature or sintering paints; Varnish for electroplating; varnish for thermal transfer tape, etc.

For the pigment dispersion for color filters, it is required that even if the pigment is contained at a high concentration, the dispersion state of the pigment is good, and the viscosity is lower than that of the ordinary dry coating. Material or sintered coating. In general, it is required that even if the pigment concentration is 5 to 20% by mass, the pigment does not aggregate, the viscosity is about 5 to 20 mPa·s, and the storage stability is good. Therefore, in the case of being used as a color filter, the pigment dispersion liquid 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 leaving for 1 month at 25 ° C (after standing) is within 10%. If the viscosity is increased, it becomes difficult to form a film thickness to be fixed.

Specific examples of the photosensitive film forming material include a photosensitive cyclized rubber resin, a photosensitive phenol resin, a photosensitive polyacrylate resin, a photosensitive polyamine resin, and a photosensitive polyimide. Photosensitive resin, unsaturated polyester resin, polyester acrylate resin, polyepoxy acrylate resin, acrylic urethane resin, polyether acrylate resin, polyol acrylate resin, etc. Resin. Further, various monomers may be added as a reactive diluent to the liquid containing the photosensitive resin.

When a photopolymerization initiator such as benzoin or benzophenone is added to a pigment coloring agent containing a photosensitive resin as a film forming material and kneaded by a conventionally known method, photohardenability and photosensitivity can be obtained. Pigment dispersion. Further, when a thermal polymerization initiator is used instead of the above photopolymerization initiator, a thermosetting pigment dispersion can be obtained.

On the other hand, specific examples of the non-photosensitive film forming material include a styrene-(meth)acrylate-based (co)polymer, a soluble polyamine-based resin, and a soluble polyimide-based resin. Soluble polyamidoximine resin, soluble polyester quinone-based resin, water-soluble salt of styrene-maleate copolymer, (meth) acrylate-(meth)acrylic copolymer A resin such as a water-soluble salt or a water-soluble amine-based polyester resin and a water-soluble salt thereof.

[Examples]

Next, the present invention will be specifically described by way of examples and comparative examples. Hereinafter, the quality basis is used as long as it is not specifically determined to be "parts" and "%".

<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-amino hydrazine was diazotized by a conventional method, at 20 to 30 ° C. The next 4 hours of coupling. After filtration and washing with water, drying was carried out, thereby obtaining 24 parts of an intermediate. After 10 parts of the obtained intermediate was dissolved in 100 parts of 20% fuming sulfuric acid, the reaction was carried out at 50 to 60 ° C for 5 hours. After standing to cool, it was poured into ice water, filtered, washed with water, and dried to obtain 12 parts of a yellow-brown pigment dispersant (I-A) represented by the following formula (I-A).

(Example I-2)

50 parts of the paste of the pigment dispersant (IA) obtained in Example I-1 (amount of pigment dispersant (IA): 10 parts) was added with 120 parts of water, and stirred at 20 to 30 ° C for 1 hour. . After adding 14 parts of tetrabutylammonium bromide and stirring for 1 hour, it was filtered, washed with water, and dried to obtain a yellow-brown pigment dispersant represented by the following formula (I-B). (I-B) 14 parts.

(Example I-3)

A yellow-green color represented by the following formula (IC) was obtained in the same manner as in the above Example I-2 except that 14 parts of aluminum sulfate 14-18 hydrate was used instead of 14 parts of tetrabutylammonium bromide. The pigment dispersant (IC) was 10.3 parts.

(Example I-4)

The following formula (ID) was obtained in the same manner as in the above Example I-1 except that 10 parts of 5-amino-2-benzimidazolidinone was used instead of 14 parts of 1-aminoindole. The red pigment dispersant (ID) is represented by 12.4 parts.

(Example I-5)

In place of the pigment dispersant (IA) paste, 48 parts (the amount of the pigment dispersant (ID): 9 parts) of the pigment dispersant (ID) obtained in Example I-4 was used instead. In the same manner as in the above Example I-2, 13 parts of a red pigment dispersant (IE) represented by the following formula (IE) was obtained.

(Example I-6)

In place of the pigment dispersant (IA) paste, 48 parts (the amount of the pigment dispersant (ID): 9 parts) of the pigment dispersant (ID) obtained in Example I-4 was used instead. In the same manner as in the above Example I-3, 9.1 parts of a red pigment dispersant (IF) represented by the following formula (IF) was obtained.

By the elemental analysis of CHN and the mass analysis using MALDI (abbreviation of matrix-assisted laser desorption ionization method), it was confirmed that the prepared pigment dispersant (I-A) to (I-F) became the target composition. Further, the results of elemental analysis regarding the pigment dispersant (I-A) to (I-F) are shown in Table I-1. As shown in Table I-1, a value close to the calculated value (theoretical value) is obtained for any of C, H, and N. Further, according to the S analysis, the value of the calculated value (theoretical value) of the number of substitutions close to the sulfonic acid group was "1". Further, regarding the pigment dispersant (I-A), a peak of m/z = 475 was detected by mass analysis. Further, the purity of the pigment dispersant (I-A) measured by high performance liquid chromatography (manufactured by JASCO Corporation: MODEL860-CO, YMC Pack Pro C18) was 93%. Therefore, based on the results of the raw materials used, elemental analysis, mass analysis, and high performance liquid chromatography, it was confirmed that the compound having the target composition was obtained.

* 1: Composition formula _{= C 23 H 13 N 3 O} 7 S

* 2: Composition = C ₃₉ H ₄₈ N ₄ O ₇ S

* 3: Composition = C ₂₃ H ₁₂ N ₃ O ₇ SAl _1/3

* 4: Composition = C ₁₆ H ₁₁ N ₅ O ₆ S

* 5: Composition = C ₃₂ H ₄₆ N ₆ O ₆ S

* 6: Composition = C ₁₆ H ₁₀ N ₅ O ₆ SAl _1/3

<Preparation of Pigment Composition (I-1) to (I-12)> (Example I-7)

100 parts of PR254 (trade name "IRGAZIN RED L3660HD", manufactured by BASF Corporation), 5 parts of the pigment dispersant (IA) obtained in Example I-1, 600 parts of sodium chloride having an average particle diameter of 5 μm, and 150 parts of diethylene glycol was added to a kneading machine equipped with a pressure cap. After pre-kneading in a kneader until a block of uniform wetting was formed, the pressure cap was closed, and the contents were pressed at a pressure of 6 kg/cm ^{2 to} start kneading. The cooling temperature and the amount of cooling water were managed while the temperature of the contents was 40 to 45 ° C, and the ground material was obtained by kneading for 4 hours. The obtained ground product was placed in 3,000 parts of a 2% sulfuric acid aqueous solution heated to 80 ° C, stirred for 1 hour, and then filtered and washed with water to remove sodium chloride and diethylene glycol. The filtered 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)

A pigment composition (I-2) to (I-) was obtained in the same manner as in the above Example I-7 except that the pigment dispersant (IB) to (IF) was used instead of the pigment dispersant (IA). 6).

(Example I-13)

Use PR177 (trade name "PALIOGEN RED L4039", manufactured by BASF Corporation A pigment composition (I-7) was obtained in the same manner as in the above Example I-7 except that PR254 was used instead.

(Examples I-14 to I-18)

A pigment composition (I-8) to (I-) was obtained in the same manner as in the above Example I-13 except that the pigment dispersant (IB) to (IF) was used instead of the pigment dispersant (IA). 12).

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

<Preparation of Pigment Dispersion (Pigment Colorant for Color Filter (CF))> (Example I-19)

Acrylic resin varnish having an average molecular weight of 12,000 and a solid concentration of 40% obtained by copolymerizing methacrylic acid/benzyl acrylate/styrene/hydroxyethyl acrylate at a molar ratio of 25/50/15/10. Prepare the skin according to the method shown below Material dispersion. 50 parts of the above acrylic resin varnish, 20 parts of the pigment composition (I-1), and a basic polymer dispersant (trade name "DISPERBYK-200 1", manufactured by BYK-Chemie Co., Ltd., solid content: 46%) 17.4 And mixing and premixing 20 parts of propylene glycol-1-monomethyl ether-2-acetate as a solvent, and then performing dispersion treatment using a transverse bead mill to obtain a pigment coloring agent for CF (Example I-19) ).

(Examples I-20~I-30)

A pigment coloring agent for CF was obtained in the same manner as in the above Example I-19 except that the pigment composition (I-2) to (I-12) was used instead of the pigment composition (I-1). Example I-20~I-30).

(Comparative Example I-1)

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

(Comparative Example I-2)

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

(Comparative Example I-3)

Except that the pigment dispersant (I-A) was not used, the same procedure as in the above Example I-13 was carried out, and a composition containing PR177 which was not treated with a pigment dispersant was obtained. Further, in the same manner as in the above Example I-19, except that the composition containing PR177 obtained in the above was used instead of the pigment composition (I-1), a pigment coloring agent for CF was obtained ( Comparative Example I-3).

(Comparative Example I-4)

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

<evaluation>

Evaluation of each of the CF pigment colorants of Examples I-19 to I-30 and Comparative Examples I-1 to I-4 (1) fluidity (storage stability), (2) gloss of the color development surface, (3) ) foreign matter in the coating film, and (4) contrast. The evaluation methods of each are shown below. Further, the evaluation results are shown in Table I-3.

(1) Fluidity (storage stability)

The viscosity (mPa‧s) of the CF pigment coloring agent immediately after preparation (initial) and after being placed at 25 ° C for one month (after standing) was measured using an E-type viscometer and set as a basis for evaluation of fluidity. . Further, the measurement conditions were temperature: room temperature (25 ° C), and number of revolutions of the rotor: 6 rpm. Further, the "post-placement viscosity/initial viscosity (%)" was calculated, and the calculated value obtained was used to evaluate "storage stability" based on the basis shown below.

○: "Position after placement/initial viscosity" is 110% or less

×: "Position after placement/initial viscosity" exceeds 110%

(2) gloss of the color surface

Using a bar coater (the thickness of the winding was 0.45 mm), the pigment coloring agent for CF was developed to a polypropylene film to form a color development surface. The gloss of the formed color surface was visually observed and observed using a gloss meter, and the "gloss of the color development surface" was evaluated based on the basis shown below. Furthermore, the higher the gloss of the color development surface, the better it can be judged.

◎: Very good

○: Good

×: bad

(3) Foreign matter in the coating film

The CF pigment coating agent was applied to the glass substrate using a rotary machine, and dried at 90 ° C for 2 minutes, and then heated at 270 ° 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 times to confirm the presence or absence of foreign matter, and the "foreign matter in the coating film" was evaluated based on the criteria shown below.

◎: no foreign matter

○: A little foreign matter

×: There is a foreign object

(4) Contrast

The CF pigment coating agent was applied to the glass substrate using a rotary machine, and dried at 90 ° C for 2 minutes, and then heated at 230 ° C for 30 minutes to form a coating film. Further, the speed of the rotating machine was changed to form three coating films. Contrast (brightest brightness/darkest brightness) was calculated by measuring the brightest brightness and the darkest brightness of the formed coating film using a contrast meter (manufactured by I-system Co., Ltd.). Further, the color of the coating film was measured by a spectrophotometer (trade name "U-2000A", manufactured by Hitachi, Ltd.) to measure the chromaticity x. Contrast the color x, draw the contrast to make a graph, draw a line approximating the graph, and read the contrast of the chromaticity x=0.650. The contrast ratio (%) of each of the examples and the comparative examples was calculated by setting the contrast of Comparative Example I-2 or the contrast of Comparative Example I-4 to "100%". Then, using the obtained calculated value, "contrast" is evaluated based on the basis shown below.

◎: 110% or more

○: 90% or more and less than 110%

×: less than 90%

As shown in Table I-3, it can be seen that the pigment coloring agent for CF of the example has lower viscosity, better storage stability, good gloss of the color developing surface, and no coating film than the pigment coloring agent for CF of the comparative example. Foreign matter is produced and high contrast. From the above, it is clarified that the pigment dispersant of the examples has an excellent effect.

Further, the pigment composition of the example is used for printing inks such as lithographic inks; various coating materials such as nitrocellulose lacquer and melamine alkyd paint; and coloring agents for synthetic resins such as vinyl chloride resin. As a result, in either case, the pigment did not aggregate and exhibited good dispersibility. Further, recently, pigment dispersants of the examples have been used in the preparation of dry or wet toners for electronic photographs, inks for inkjet recording, inks for thermal transfer recording, inks for writing instruments, and the like which are particularly required for high dispersibility. . As a result, in any case, excellent dispersibility was exhibited.

<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-amino hydrazine was diazotized by a conventional method, at 20 to 30 ° C. The next 4 hours of coupling. After filtration and washing with water, drying was carried out, thereby obtaining 24 parts of an intermediate. After 10 parts of the obtained intermediate was dissolved in 100 parts of chlorosulfonic acid, 10 parts of sulfoxide was added, and the reaction was carried out at 50 to 60 ° C for 5 hours. After standing to cool, it was poured into ice water, filtered, and then washed with ice water to obtain a water paste of sulfonium chloride. The obtained water paste of sulfonium chloride was stirred and dispersed to a mixture of 200 parts of water and 100 parts of ice to obtain 7 parts of N,N-diethylaminopropylamine. After stirring at 20 to 30 ° C for 5 hours, the reaction was carried out by heating at 60 to 70 ° C for 1 hour. After completion of the reaction, the mixture was filtered, washed with water, and dried to obtain 14 parts of a yellow-brown pigment dispersant (II-A) represented by the following formula (II-A).

(Example II-2)

The same procedure as in the above Example II-1 was carried out except that 8 parts of N-(3-aminopropyl)cyclohexylamine was used instead of N,N-diethylaminopropylamine. 15 parts of a yellow-brown pigment dispersant (II-B) represented by the following formula (II-B) was obtained.

(Example II-3)

Using N, N, N", N"-tetraethyldiethylidene triamine 11 parts instead of N,N-diethylaminopropylamine 7 parts, in addition to the above Example II-1 In the same manner, 16 parts of a yellow-brown pigment dispersant (II-C) represented by the following formula (II-C) was obtained.

(Example II-4)

In the same manner as in the above Example II-1, except that 10 parts of 5-amino-2-benzimidazolidinone was used instead of 14 parts of 1-aminoindole, the following formula (II-) was obtained. D) 15 parts of the red pigment dispersant (II-D).

(Example II-5)

10 parts of 5-amino-2-benzimidazolidinone was used in place of 14 parts of 1-aminoindole, and 10 parts of N-(3-aminopropyl)cyclohexylamine was used instead of N,N-diethyl. In the same manner as in the above Example II-1, 16 parts of a red pigment dispersant (II-E) represented by the following formula (II-E) was obtained, except that 7 parts of the aminopropylamine was used.

(Example II-6)

10 parts of 5-amino-2-benzimidazolidinone was used instead of 14 parts of 1-amino hydrazine used in Example II-1, and N, N, N", N"-tetraethyl group was used. Except that 14 parts of ethyltriamine was used instead of N,N-diethylaminopropylamine, in the same manner as in the above Example II-1, the following formula (II-F) was obtained. 17 parts of the red pigment dispersant (II-F).

Confirmation of the prepared pigment dispersant (II-A) by elemental analysis of CHN and mass analysis using MALDI (abbreviation of matrix-assisted laser desorption ionization method) ~(II-F) becomes the target component. Further, the results of elemental analysis regarding the pigment dispersant (II-A) to (II-F) are shown in Table II-1. As shown in Table II-1, the value of almost any calculated value (theoretical value) is obtained for any of C, H, and N. Further, by S analysis, a value close to the calculated value (theoretical value) of the number of substitutions of the sulfonamide group "1" was obtained. Further, regarding the pigment dispersant (II-A), a peak of m/z = 587 was detected by mass analysis. Further, the purity of the pigment dispersant (II-A) measured by high performance liquid chromatography (manufactured by JASCO Corporation: MODEL860-CO, manufactured by YMC Co., Ltd.: YMCPack Pro C18) was 91%. Therefore, based on the results of the raw materials used, elemental analysis, mass analysis, and high performance liquid chromatography, it was confirmed that the compound having the target composition was obtained.

<Preparation of Pigment Composition (II-1)~(II-12)> (Example II-7)

100 parts of PR254 (trade name "IRGAZIN RED L3660HD", manufactured by BASF Corporation), 12 parts of the pigment dispersant (II-A) obtained in Example II-1, and 600 parts of sodium chloride having an average particle diameter of 5 μm. And 150 parts of diethylene glycol were added to a kneading machine equipped with a pressure cap. After pre-kneading in a kneader until a block of uniform wetting was formed, the pressure cap was closed, and the contents were pressed at a pressure of 6 kg/cm ^{2 to} start kneading. The cooling temperature and the amount of cooling water were managed while the temperature of the contents was 40 to 45 ° C, and the ground material was obtained by kneading for 4 hours. The obtained ground product was placed in 3,000 parts of a 2% sulfuric acid aqueous solution heated to 80 ° C, stirred for 1 hour, and then filtered and washed with water to remove sodium chloride and diethylene glycol. The filtered 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)

A pigment composition (II-) was obtained in the same manner as in the above Example II-7 except that the pigment dispersant (II-B) to (II-F) was used instead of the pigment dispersant (II-A). 2)~(II-6).

(Example II-13)

A pigment composition (II-7) was obtained in the same manner as in the above Example II-7 except that PR177 (trade name "PALIOGEN RED L4039", manufactured by BASF Corporation) was used instead of PR254.

(Examples II-14 to II-18)

A pigment composition (II-) was obtained in the same manner as in the above Example II-13 except that the pigment dispersant (II-B) to (II-F) was used instead of the pigment dispersant (II-A). 8)~(II-12).

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

<Preparation of Pigment Dispersion (Pigment Colorant for Color Filter (CF))> (Embodiment 19)

Acrylic resin varnish having an average molecular weight of 12,000 and a solid concentration of 40% obtained by copolymerizing methacrylic acid/benzyl acrylate/styrene/hydroxyethyl acrylate at a molar ratio of 25/50/15/10. A pigment dispersion was prepared according to the method shown below. 50 parts of the acrylic resin varnish, 20 parts of the pigment composition (II-1), and an acidic polymer pigment dispersant (trade name "DISPERBYK-110", manufactured by BYK-Chemie Co., Ltd., 52% solid content) 15.4 parts And as a solvent for propylene glycol-1-monomethyl ether 20 parts of the -2-acetate was mixed and pre-mixed, and then subjected to dispersion treatment using a transverse bead mill to obtain a pigment coloring agent for CF (Examples II-19).

(Examples II-20 to II-30)

A pigment coloring agent for CF was obtained in the same manner as in the above Example II-19 except that the pigment composition (II-2) to (II-12) was used instead of the pigment composition (II-1). Example II-20~II-30).

(Comparative Example II-1)

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

(Comparative Example II-2)

The pigment dispersant (II-G) represented by the following formula (II-G) described in Patent Document 1 is used in the same manner as in the above Example II-7 except for the pigment dispersant (II-A). The manner was carried out to obtain a pigment composition (II-13). Further, in the same manner as in the above Example II-19, except that the pigment composition (II-13) obtained in the above was used instead of the pigment composition (II-1), a pigment for CF was obtained. Colorant (Comparative Example II-2).

(Comparative Example II-3)

Except that the pigment dispersant (II-A) was not used, the same procedure as in the above Example II-13 was carried out, and a composition containing PR177 which was not treated with a pigment dispersant was obtained. Further, in the same manner as in the above Example II-19, except that the composition containing PR177 obtained in the above was used instead of the pigment composition (II-1), a pigment coloring agent for CF was obtained ( Comparative Example II-3).

(Comparative Example II-4)

The pigment dispersant (II-H) represented by the following formula (II-H) described in Patent Document 2 is used in the same manner as in the above Example II-13 except for the pigment dispersant (II-A). The manner was carried out to obtain a pigment composition (II-14). Further, in the same manner as in the above Example II-19, except that the pigment composition (II-14) obtained in the above was used instead of the pigment composition (II-1), a pigment for CF was obtained. Colorant (Comparative Example II-4).

<evaluation>

Evaluation of each of the CF pigment dyes of Examples II-19 to II-30 and Comparative Examples II-1 to II-4 (1) fluidity (storage stability), (2) gloss of the color development surface, (3) ) foreign matter in the coating film, and (4) contrast. The evaluation methods of each are shown below. Further, the evaluation results are shown in Table II-3.

(1) Fluidity (storage stability)

The viscosity (mPa‧s) of the CF pigment coloring agent immediately after preparation (initial) and after being placed at 25 ° C for one month (after standing) was measured using an E-type viscometer and set as a basis for evaluation of fluidity. . Further, the measurement conditions were temperature: room temperature (25 ° C), and number of revolutions of the rotor: 6 rpm. Further, the "post-placement viscosity/initial viscosity (%)" was calculated, and the calculated value obtained was used to evaluate "storage stability" based on the basis shown below.

○: "Position after placement/initial viscosity" is 110% or less

×: "Position after placement/initial viscosity" exceeds 110%

(2) gloss of the color surface

Using a bar coater (the thickness of the winding was 0.45 mm), the pigment coloring agent for CF was developed to a polypropylene film to form a color development surface. The gloss of the formed color surface was visually observed and observed using a gloss meter, and the "gloss of the color development surface" was evaluated based on the basis shown below. Furthermore, the higher the gloss of the color development surface, the better it can be judged.

◎: Very good

○: Good

×: bad

(3) Foreign matter in the coating film

The CF pigment coating agent was applied to the glass substrate using a rotary machine, and dried at 90 ° C for 2 minutes, and then heated at 270 ° 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 times to confirm the presence or absence of foreign matter, and the "foreign matter in the coating film" was evaluated based on the criteria shown below.

◎: no foreign matter

○: A little foreign matter

×: There is a foreign object

(4) Contrast

The CF pigment coating agent was applied to the glass substrate using a rotary machine, and dried at 90 ° C for 2 minutes, and then heated at 230 ° C for 30 minutes to form a coating film. Further, the speed of the rotating machine was changed to form three coating films. Contrast (brightest brightness/darkest brightness) was calculated by measuring the brightest brightness and the darkest brightness of the formed coating film using a contrast meter (manufactured by I-system Co., Ltd.). Further, the color of the coating film was measured by a spectrophotometer (trade name "U-2000A", manufactured by Hitachi, Ltd.) to measure the chromaticity x. Control the color x, the contrast will be The line is drawn to make a graph, draw a line approximating the graph, and read the contrast of chromaticity x=0.650. The contrast ratio (%) of each of the examples and the comparative examples was calculated by setting the contrast of Comparative Example II-2 or the contrast of Comparative Example II-4 to "100%". Then, using the obtained calculated value, "contrast" is evaluated based on the basis shown below.

◎: 110% or more

○: 90% or more and less than 110%

×: less than 90%

As shown in Table II-3, it can be seen that the pigment coloring agent for CF of the example has lower viscosity, better storage stability, good gloss of the color developing surface, and no coating film than the pigment coloring agent for CF of the comparative example. Foreign matter is produced and high contrast. From the above, it is clarified that the pigment dispersant of the examples has an excellent effect.

Further, the pigment composition of the examples is used for printing inks such as lithographic inks; various coatings such as nitrocellulose lacquer and melamine alkyd coating; vinyl chloride resin, etc. Synthetic resin coloring agent, etc. As a result, in either case, the pigment did not aggregate and exhibited good dispersibility. Further, recently, pigment dispersants of the examples have been used in the preparation of dry or wet toners for electronic photographs, inks for inkjet recording, inks for thermal transfer recording, inks for writing instruments, and the like which are particularly required for high dispersibility. . As a result, in any case, excellent dispersibility was exhibited.

(industrial availability)

The pigment dispersant of the present invention is formulated as a printing ink (lithographic ink, gravure ink, etc.), various coatings, plastics, pigment printing agents, dry or wet toner for electronic photographs, ink for inkjet recording, thermal transfer recording It is useful for dispersing agents such as inks, resists for color filters, inks for writing instruments, and the like, and the use of the pigment dispersants is expected.

Claims (6)

A pigment dispersant which is a compound represented by any one of the following formulae (IA) to (IF) and (II-A) to (II-F): A pigment composition containing a pigment and the pigment dispersant of claim 1. The pigment composition of claim 2, wherein the pigment dispersant is relative to the above The blending amount of the pigment of 100 parts by mass is 0.5 to 40 parts by mass. A pigment coloring matter comprising the pigment composition of claim 2 or 3 and a film forming material. The pigment coloring agent of claim 4, which is used for image display, image recording, printing ink, ink for notes, plastic, pigment printing or paint. A pigment colorant according to claim 4, which is for use as a color filter.