JP5035718B2 - Pigment dispersant and use thereof - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a colorless or pale-colored pigment dispersant and its use. <P>SOLUTION: The pigment dispersant is expressed by general formula (1). The dispersant can disperse various pigments at high concentration and low viscosity into a dispersion medium such as an image displaying colorant such as coating liquid for forming color filter (CF) pixels, an image recording colorant, a coating material and printing ink. The pigment composition and pigment colorant are also used, in particular, by mixing a plurality of ultrafine particulates different in chemical structures and physical properties. They are useful as a colorant for a coating liquid for forming CF pixels requiring low viscosity and long term storage stability. <P>COPYRIGHT: (C)2008,JPO&amp;INPIT

Description

  The present invention relates to a pigment dispersant (hereinafter sometimes referred to simply as “dispersant”) and use thereof, and particularly, a dispersant useful as an organic pigment, a pigment composition containing the dispersant, a pigment colorant, particularly a color The present invention relates to a pigment colorant useful for forming a pixel of a filter (hereinafter sometimes simply referred to as “CF”).

  Generally, when a pigment is mixed and dispersed in a vehicle such as paint, gravure ink, offset ink or the like, it is difficult to stably disperse the pigment in the vehicle. Fine pigment particles once dispersed in the vehicle are There is a tendency to aggregate in the vehicle. As a result, the viscosity of the vehicle in which the pigment is dispersed is increased, or the coloring power of the ink or paint using the vehicle in which the pigment is dispersed is decreased, or the gloss of the coating film is decreased. Will occur.

  Conventionally, CF used for manufacturing liquid crystal color displays, image sensors, etc. is a CF pixel in which three color pigments of red (R), green (G) and blue (B) are dispersed in a photosensitive resin liquid, respectively. A forming pigment colorant (dispersion) is applied to a CF substrate by a spin coating method to form a colored film, and then the colored film is exposed and developed through a photomask to pattern the colored film. It is mainly created by a method of forming a desired pixel on a working substrate.

  As the main pigment used in the production of CF, the green pigment is phthalocyanine green, such as C.I. I. Pigment Green (hereinafter referred to as PG) 36, PG7, etc .: The red pigment is a diketopyrrolopyrrole (hereinafter referred to as DPP) red, for example, C.I. I. Pigment Red (hereinafter referred to as PR) 254, anthraquinone red, such as PR177, azo red, such as PR242, etc .: The blue pigment is phthalocyanine blue, such as C.I. I. Pigment Blue (hereinafter referred to as PB) 15: 6 is generally used. However, there is a difference between the hue of these pigments and the color characteristics required for the liquid crystal display, and yellow pigments such as C.I. I. Pigment Yellow (hereinafter referred to as PY) 138, PY139, PY150 and the like are used in small amounts as complementary colors, and purple pigments such as C.I. I. A small amount of pigment violet (hereinafter referred to as PV) 23 is used as a complementary color (Patent Documents 1 to 3).

Japanese Patent Laid-Open No. 2-187469 JP 2004-91497 A JP 2005-112915 A

  In particular, due to the demand for further improvement in the performance of CF, it has become necessary to improve the transparency of the colored pixels, increase the contrast of the transmitted light of the colored pixels, and increase the pigment concentration of the colored pixels. However, with ordinary pigment dispersion, it is difficult to improve the transparency of colored pixels by improving the dispersibility of the pigment, and to prevent an increase in viscosity and a decrease in storage stability due to an increase in the pigment concentration. Improvement is demanded.

  In general, in order to disperse the pigment in a fine state, a pigment derivative is used as a dispersant. However, the effect is limited to a pigment having a specific structure, and a pigment having a different structure often has no dispersion effect. Also, blue, green or purple pigment derivatives cannot be used for the dispersion of yellow pigments. Moreover, when the addition amount of a dispersing agent is increased, color dullness will occur in the colored product. From these points, a pigment derivative that can be used for any pigment and is colorless or light-colored is desired.

  Accordingly, the object of the present invention is to provide printing ink (offset ink, gravure ink, etc.), various paints, pigment printing agents, colorants for image display such as CF pixel forming colorants, electrophotographic dry toner or wet toner, ink jet recording. In the production of colorants for image recording, such as ink for printing, ink for thermal transfer recording, ink for writing instruments, etc., the above-mentioned ink has excellent fluidity and stability, preventing aggregation of pigment particles dispersed in the colorant such as these inks And the like.

The configuration of the present invention is as follows.
1. The following dispersant (A), dispersing agent (B), a pigment dispersing agent characterized and Turkey are represented by any of the formulas of the dispersing agent (C), and dispersing agent (D).

2 . A pigment composition comprising a pigment and a pigment dispersant, wherein the pigment dispersant is the pigment dispersant described in 1 above.
3 . 3. The pigment composition according to 2 above, wherein the blending ratio of the pigment dispersant is 0.05 to 40 parts by mass with respect to 100 parts by mass of the pigment.

4 . A pigment colorant comprising the pigment composition described in 2 or 3 above and a film-forming material.
5 . 5. The pigment colorant as described in 4 above, which is a colorant for image display, a colorant for image recording, printing ink, writing ink, plastic colorant, colorant for pigment printing or paint colorant.
6 . 5. The pigment colorant as described in 4 above, which is a color filter pixel forming colorant.

  The present inventors have solved the above-mentioned problems when using the dispersant as a dispersant in the preparation of a CF pixel forming coating solution having a high pigment concentration, and improving the color quality of the CF pixel forming coating solution. As a result of diligent research to develop a dispersant capable of lowering the viscosity, the colorless or slightly colored triazine compound represented by the general formula (1) can be added regardless of the type of pigment. Even if the amount is increased, there is little effect on the hue of the dispersion and the coating film, the viscosity of the CF pixel forming coating solution can be reduced, and the coating solution can be prevented from thickening and gelling during storage. As a result, it has been found that the transparency of colored pixels, which is one of the most important characteristics, is also improved.

  The dispersant of the present invention stably disperses various pigments at high concentrations and low viscosities in dispersion media such as image display colorants such as CF pixel forming coating liquids, image recording colorants, paints and printing inks. Can be made. In addition, the pigment composition and the pigment colorant of the present invention are used for the formation of CF pixels that are used in particular by mixing a plurality of ultrafine pigments having different chemical structures and physical properties, and have low viscosity and long-term storage stability. Useful as a colorant for coating solutions. For example, when it is used as a pigment in a combination of PG36 and PY138, it has an effect of giving excellent dispersion stability to both pigments. It is possible to form a green pixel having a high transparency and excellent fastness such as light resistance, heat resistance, solvent resistance, chemical resistance, and water resistance.

  Next, the present invention will be described in more detail with reference to preferred embodiments. The dispersant of the present invention is characterized by having a colorless or slightly colored triazine structure in its structure, and the dispersant of the present invention has an excellent affinity for various pigments, and has a wide range of pigments. Can be used to distribute Moreover, since the dispersing agent of this invention has the outstanding pigment dispersion effect, it can be used for manufacture of the coloring agent used in various uses. Furthermore, better results are obtained with the dispersants of the present invention in the form of quaternary ammonium salts of sulfonic acids, depending on the application.

  The compound of the general formula (1) which is a dispersant characterizing the present invention is obtained by reacting 2 mol of a heterocyclic primary amine with 1 mol of a secondary amine or thiol compound per 1 mol of cyanuric chloride. According to sulphonation of the product.

The above heterocyclic primary amine is a compound constituting the substituents R ₁ and R ₂ in the general formula (1), such as 3- or 4-aminophthalimide, 3-amino-9-ethylcarbazole, Examples thereof include 4- or 5-aminobenzimidazolone, aminoquinoline, and sulfonated products thereof. These heterocyclic primary amines can be used alone or as a mixture. Particularly preferred heterocyclic primary amines include 4-aminophthalimide, 3-amino-9-ethylcarbazole, 5-aminobenzimidazolone, aminoquinoline, and sulfonated products thereof.

  The secondary amine or thiol compound is a compound constituting the substituent X in the general formula (1). For example, dibenzylamine, diphenylamine, N-benzyl-1-naphthylamine, N-methylaniline or N- Examples thereof include benzylaniline and sulfonated products thereof, and examples of thiols include thiophenol, benzylthiol or thionaphthol, and sulfonated products thereof. Particularly preferred secondary amines or thiol compounds include dibenzylamine, thiophenol, and sulfonated products thereof.

  When at least one of the primary amine and secondary amine or thiol compound has a sulfone group, the average sulfone group in the obtained compound of the general formula (1) is 0.5 to 4 Combine reaction materials with On the other hand, when none of the primary amine and the secondary amine or the thiol compound has a sulfone group, the average sulfone group is 0.5 to 4 by sulfonation. It can be set as the compound of the said General formula (1). If the average sulfone group is less than 0.5, the effect as a dispersant is not sufficient, while if the average sulfone group exceeds 4, the water resistance of a coating film containing the dispersant is poor. The average number of introduced sulfone groups is 0.5 to 2.

  When one synthesis example of the compound represented by the general formula (1) is given, for example, 2 mol of a heterocyclic primary amine having no sulfone group and 1 mol of cyanuric chloride are inactive such as o-dichlorobenzene. Reaction in a solvent at 130 to 170 ° C. for 2 to 6 hours, addition of a secondary amine having no sulfone group, reaction at 150 to 170 ° C. for 3 to 4 hours, and then the product is known as fuming sulfuric acid or the like Can be obtained by sulfonation according to a conventional method. Moreover, the metal salt, its ammonium salt, or an amine salt can be obtained by a conventionally well-known method using the compound represented by General formula (1).

  Examples of the amine that forms an amine salt with the compound represented by the general formula (1) include, for example, (mono, di, or tri) alkylamines, substituted or unsubstituted alkylenediamines, alkanolamines, and alkylammoniums. Although a chloride etc. are mentioned, Quaternary ammonium salt is especially preferable. Examples of the metal that forms a metal salt with the compound represented by the general formula (1) include, for example, alkali metals such as Li, Na, and K, and polyvalent metals such as Ca, Ba, Al, Mn, Sr, Mg, and Ni. A metal is mentioned.

  The pigment composition of the present invention comprises a pigment and the dispersant of the present invention. The mixing ratio of the dispersant to the pigment in the pigment composition is preferably 0.05 to 40 parts by mass, more preferably 0.1 to 10 parts by mass with respect to 100 parts by mass of the pigment. If the blending ratio of the dispersant is too small, it is difficult to sufficiently obtain the effect of the intended dispersant. On the other hand, if the blending ratio of the dispersant is too large, the effect of using only a large amount cannot be obtained, and conversely, the physical properties of the paint or ink vehicle using the obtained pigment composition are deteriorated. The hue of the pigment to be dispersed may change depending on the color of the dispersant itself.

  Examples of pigments that can be dispersed by using the dispersant of the present invention include soluble / insoluble azo pigments, high molecular weight azo pigments, phthalocyanine pigments, quinacridone pigments, anthraquinone pigments, diketopyrrolopyrrole pigments, quinophthalone pigments, methine Examples thereof include azomethine pigments, azomethine azo pigments, perylene pigments, perinone pigments, isoindolinone pigments, isoindoline pigments, and metal complex pigments. Among these, a pigment selected from PR177, PR242, PR254, PY138, PY139, PY150, PG7, PG36, and poly (12-16) bromocopper phthalocyanine green pigment is particularly preferable.

Further, the method for dispersing the pigment by the dispersant of the present invention is not particularly limited, and examples thereof include the following methods.
(1) A pigment and a 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) When dispersing the pigment in the vehicle or the like, the pigment and the dispersant are separately added to the vehicle or the like at a predetermined ratio to disperse the pigment in the vehicle.
(3) After separately dispersing the pigment and the dispersant in a vehicle or the like, the obtained dispersions are mixed at a predetermined ratio to disperse the pigment.
(4) In a dispersion obtained by dispersing the pigment in a vehicle or the like, a dispersant is added at a predetermined ratio to disperse the pigment.
Any of these methods can achieve the desired pigment dispersion effect. More effectively, the method (1) or (2) is desirable.

  The pigment composition of the present invention can be produced by mixing the pigment and the dispersant of the present invention by a conventionally known method, and the production method is not particularly limited. For example, 1) A method of mixing pigment powder and dispersant powder without using a disperser, and 2) Mechanically mixing the pigment and dispersant with various dispersers such as kneaders, rolls, attritors and horizontal bead mills. 3) A method of adding and mixing a liquid in which the dispersant of the present invention is dissolved or finely dispersed into a pigment suspension such as an aqueous or organic solvent, and uniformly depositing the dispersant on the pigment surface. 4) A method in which a pigment and a dispersant are dissolved in a solvent having strong dissolving power such as sulfuric acid and then co-precipitated with a poor solvent such as water. Thus, when preparing the pigment composition, the dispersant may be used in any form of solution, slurry, paste and powder, and any form can exert the effects of the present invention.

  A pigment colorant using the pigment composition of the present invention contains a polymer, an oligomer and / or a monomer as the above-described finer pigment composition and film-forming material, and is a colorant for image display and image recording. Used in colorants, printing inks, writing inks, plastic colorants, pigment printing colorants, paints and the like. In particular, it is used in image display methods such as CF pixel forming colorants as image display materials, and image recording agents such as inkjet inks or electrodeposition recording liquids, and electrophotographic developers as inkjet recording methods or electrodeposition recordings, respectively. It is used for image recording methods such as a method and an electrophotographic method.

  A CF pixel forming dispersion will be described as an example of an image display material. When preparing the dispersion, the pigment composition of the present invention is added to an organic solvent solution containing an appropriate film-forming resin, premixed, and dispersed. For example, the above pigment composition is uniformly mixed and ground by a dispersing machine such as a vertical medium disperser, horizontal medium disperser, ball mill, etc., and this is added and mixed in a liquid containing a film-forming polymer, sulfuric acid, etc. After the pigment and the dispersant of the present invention are dissolved in the solution, the sulfuric acid solution is precipitated in water, and both are separated as a solid solution or a eutectoid. The resulting pigment composition is formed into a film-forming polymer in the same manner as described above. For example, a method of adding and mixing in a liquid containing the above, and grinding and dispersing in a horizontal wet medium disperser (bead mill) such as dyno mill.

  In the present invention, as a liquid containing a film-forming material for dispersing a pigment and a dispersant to form a pigment colorant, a film-forming polymer used in a conventionally known pigment colorant for CF pixel formation is used. . Further, an organic solvent, water, or a mixture of an organic solvent and water is used as the liquid medium. Moreover, conventionally well-known additives, for example, additives, such as a dispersion auxiliary agent, a smoothing agent, and an adhesive agent, can be added to a pigment colorant as needed.

  The mass ratio of the pigment composition to the film-forming material in the liquid containing the film-forming material is preferably in the range of 5 to 500 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 is used. Examples of the liquid containing a photosensitive film-forming material include a liquid containing a photosensitive film-forming material used for ultraviolet curable ink, electron beam curable ink, and the like, and a liquid containing a non-photosensitive film-forming material. Examples include varnishes used for printing inks such as letterpress inks, lithographic inks, gravure inks, screen inks, varnishes used for room temperature drying and baking paints, varnishes used for electrodeposition coating, varnishes used for thermal transfer ribbons, etc. Can be mentioned.

  Examples of photosensitive film forming materials include photosensitive cyclized rubber resins, photosensitive phenol resins, photosensitive polyacrylate resins, photosensitive polyamide resins, photosensitive polyimide resins, and unsaturated polyester resins and polyesters. Examples include acrylate resins, polyepoxy acrylate resins, polyurethane acrylate resins, polyether acrylate resins, polyol acrylate resins, and various monomers as reactive diluents.

  Moreover, it can be set as a photocurable photosensitive pigment coloring agent by adding photoinitiators, such as a benzoin ether and a benzophenone, to the pigment coloring agent containing photosensitive resin, and kneading by a conventionally well-known method. Moreover, it can replace with said photoinitiator and can use it as a thermosetting pigment coloring agent using a thermal polymerization initiator.

  Examples of non-photosensitive film-forming materials include styrene- (meth) acrylic acid ester (co) polymers, soluble polyamide resins, soluble polyimide resins, soluble polyamideimide resins, soluble polyesterimide resins, styrene -Water-soluble salt of maleic acid ester-based copolymer, water-soluble salt of (meth) acrylic acid ester- (meth) acrylic acid-based copolymer, water-soluble amino polyester-based resin, and the like.

  Next, the present invention will be described more specifically with reference to synthesis examples, examples and comparative examples. In the text, “part” or “%” is based on mass.

Synthesis example 1
58 parts of 4-aminophthalimide and 30 parts of cyanuric chloride are added to 1,100 parts of o-dichlorobenzene and reacted at 130 ° C. for 5 hours. After cooling, 70 parts of dibenzylamine are added and stirred at 140 ° C. for 5 hours. After cooling, the mixture was filtered, washed with alcohol, then washed with water and dried to obtain 72 parts of 2,4-bis (4-phthalimidoamino) -6-dibenzylamino-1,3,5-triazine. Subsequently, 72 parts of this compound is added to 600 parts of 5% fuming sulfuric acid at 10 ° C. or lower, and then reacted at 20 ° C. for 5 hours. After cooling, the reaction mixture was precipitated into 1,800 parts of ice water, filtered and washed with water. As a result of elemental analysis of sulfur, 79 parts of the following dispersant (A) having 1.1 sulfone groups introduced on average per molecule was obtained.

Synthesis example 2
55 parts of the following dispersant (B) was obtained in the same manner as in Synthesis Example 1 except that diphenylamine was used instead of dibenzylamine in Synthesis Example 1.

Synthesis example 3
240 parts of water was added to 90 parts (pure amount 18 parts) of the dispersant (A) paste of Synthesis Example 1 and stirred at 25 ° C. for 1 hour. To this, 11 parts of tetrabutylammonium chloride was added, stirred for 1 hour, filtered, washed with water, and dried to obtain 19 parts of the following dispersant (C).

Synthesis example 4
18 parts of the following dispersant (D) was obtained in the same manner as in Synthesis Example 3, except that the dispersant (B) was used instead of the dispersant (A) in Synthesis Example 3.

  Examples of the dispersant represented by the general formula (1) of the present invention include the following compounds as well as the following compounds, but the present invention is not limited thereto. In the following, n is in the range of 0.5 to 2.0.

Examples 1-4
In order to evaluate the effect of the dispersant of the present invention, a gravure ink having the following formulation (1) was prepared.
Formulation (1)
-Pigment 9.5 parts-Dispersants (A) to (D) 0.5 parts-Nitrified cotton varnish 16.0 parts-Polyamide varnish 20.0 parts-Thinner 54.0 parts Naphthol AS monoazo pigment (C I.PR146), the dispersants (A) (Example 1), (B) (Example 2), (C) (Example 3) and (D) obtained in Synthesis Examples 1 to 4, respectively. ) (Example 4) was used, and the above-described blended components were put in a container, glass beads were added and dispersed with a paint conditioner, and four types of gravure polyamide inks were prepared.

Comparative Example 1
C. without using a dispersant. I. Except for using 10.0 parts of PR146, the same operation as in Example 1 was performed to prepare a polyamide ink for gravure to which no dispersant was added.

The viscosity of the polyamide ink for gravure of Examples 1 to 4 and the gloss of the color development surface coated with the ink were compared with those of the ink of Comparative Example 1. The viscosity of each ink and the gloss of the color development surface were measured according to the following method and compared with the ink of Comparative Example 1.
Viscosity: Measured using a B-type viscometer under the conditions of room temperature (25 ° C.) / 30 rpm.
Gloss: A bar coater (winding thickness: 0.15 mm) was used to develop color on a polypropylene film, and the gloss of the developed surface was compared visually and with a gloss meter. In addition, the thing with high gloss was made favorable and was described with the following parameter | index.
○: Good Δ: Slightly good ×: Poor The results are shown in Table 1.

Example 5 (Pigment composition (1))
In 1000 parts of water, C.I. I. Add 19.0 parts of PR146 and disperse to make a slurry. Thereto is added a slurry of 1.0 part of the dispersant (A) obtained in Synthesis Example 1 and 0.1 part of caustic soda in 50 parts of water. The mixed slurry is heated to 70 ° C. and the pH is corrected to 4-5. After stirring for 20 minutes, it was filtered, dried and pulverized to obtain 19.9 parts of the pigment composition (1) of the present invention.
A gravure polyamide ink (1) was prepared in the same manner as in Example 1 except that 10.0 parts of the pigment composition (1) was replaced by the total amount of the pigment and dispersant in the formulation (1) of Example 1. .

Examples 6 to 8 (Pigment compositions (2) to (4))
The same operations as in Example 5 were repeated except that the dispersants (B) to (D) obtained in Synthesis Examples 2 to 4 were used in place of the dispersant (A), respectively, and the pigment compositions (2) to (2) to (4) was obtained. The total amount of the pigment and dispersant in the formulation (1) of Example 1 was replaced with 10.0 parts of the above pigment compositions (2) to (4), respectively, and the rest was the same as in Example 1 except for the polyamide for gravure Inks (2) to (4) were prepared.

  For these inks (1) to (4), the viscosity of the ink and the gloss of the color development surface were compared with those of the ink of Comparative Example 1 in the same manner as in Example 1. The results are shown in Table 1.

  As shown in Table 1, excellent pigment dispersion effects were observed in the inks (1) to (4) to which the dispersants (A) to (D) of the present invention were added. Even when the viscosity of these inks (1) to (4) was measured after standing for 1 week, almost no increase in viscosity was observed compared to the ink of Comparative Example 1. Further, not only as a pigment composition but also when a mixture of a vehicle and a pigment and a dispersant added separately was mixed and dispersed, the effect of a sufficient dispersant was obtained as described above.

Examples 9 to 12 (Pigment compositions (5) to (8))
C. I. The same procedure as in Example 5 was repeated, except that a diketopyrrolopyrrole pigment (CI PR254) was used instead of PR146 and the dispersants (A) to (D) were used, respectively, and the pigment composition (5 ) To (8) were obtained.

Examples 13 to 16 (Pigment compositions (9) to (12))
C. I. The same procedure as in Example 5 was repeated, except that copper phthalocyanine green pigment (CI PG36) was used instead of PR146, and dispersants (A) to (D) were used, respectively, and a pigment composition (9) To (12) were obtained.

Examples 17 to 20 (Pigment compositions (13) to (16))
C. I. The same procedure as in Example 5 was repeated, except that a copper phthalocyanine pigment (CI PB15: 6) was used instead of PR146 and the dispersants (A) to (D) were used, respectively, and the pigment composition (13 ) To (16) were obtained.

Examples 21 to 24 (pigment compositions (17) to (20))
C. I. The same operations as in Example 5 were repeated except that dioxazine pigment (C.I.PV23) was used instead of PR146, and dispersants (A) to (D) were used, respectively, and pigment compositions (17) to ( 20) was obtained.

Examples 25 to 28 (Pigment compositions (21) to (24))
C. I. The same procedure as in Example 5 was repeated, except that a benzimidazolone pigment (C.I.PY185) was used instead of PY146, and dispersants (A) to (D) were used. To (24) were obtained.

In order to evaluate the effect of the dispersant using the above pigment compositions (5) to (24), a gravure urethane ink having the following composition (2) was prepared.
Formula (2)
-Pigment composition (5) to (24) 10.0 parts-Nitrified cotton varnish 5.0 parts-Polyurethane varnish 35.0 parts-Thinner 50.0 parts Add the above ingredients into a container and add steel balls. It was dispersed with a paint conditioner to prepare gravure urethane inks (5) to (24).

Comparative Examples 2-6
In place of pigment compositions (5), (9), (13), (17) and (21), C.I. I. PY254 (Comparative Example 2), C.I. I. PG36 (Comparative Example 3), C.I. I. PB15: 6 (Comparative Example 4), C.I. I. PV23 (Comparative Example 5), and C.I. I. Except for using PY185 (Comparative Example 6), five types of gravure urethane inks with no dispersant added were prepared in the same manner as in Examples 9, 13, 17, 21 and 25.

  The viscosity of the inks of Examples 9 to 28 and the gloss of the color development surface were compared with those of the inks of Comparative Examples 2 to 6. The gloss of the color development surface and the viscosity of the ink were measured in the same manner as in the case of the above-described polyamide ink for gravure, and were subjected to relative evaluation as in the case of the inks of Comparative Examples 2-6. The results are shown in Table 2.

  As shown in Table 2, as in the case of the gravure polyamide ink, when any of the dispersants (A) to (D) of the present invention was added, a dispersion effect was recognized although there was a slight difference. . Even when the viscosity of the ink of the example was measured after standing for 1 week, an increase in the viscosity was hardly observed as compared with the case of the ink of the comparative example.

Examples 29 to 32 (Pigment compositions (25) to (28))
C. I. Instead of PR146, C.I. I. The same operations as in Example 5 were repeated except that PR177 was used and the dispersants (A) to (D) were used as dispersants, to obtain pigment compositions (25) to (28).

Using these pigment compositions (25) to (28), paints having the following formulation (3) were prepared in order to evaluate the effect of the dispersant.
Formula (3)
・ Pigment composition (25) to (28) 6.0 parts ・ Acrylic varnish 46.6 parts ・ Melamine varnish 20.0 parts ・ Thinner 30.0 parts Put the above ingredients in a container and add glass beads. A paint was prepared by dispersing with a paint conditioner.

Comparative Example 7
Instead of 10.0 parts of pigment composition (25), C.I. I. Except for using 10.0 parts of PR177, the same operation as in Example 29 was performed to prepare a coating material to which no dispersant was added.

The viscosity and color development of these paints and the gloss of the paint surface after baking were compared with those of the comparative paints. The viscosity of the paint and the gloss of the color development surface were measured according to the following method and compared with the paint of the comparative example.
Viscosity: Measured using a B-type viscometer under the conditions of room temperature (25 ° C.) / 30 rpm.
Gloss: Using an applicator (6 mils), the gloss of the coated surface after color development and baking on an art paper was compared visually and with a gloss meter. In addition, the thing with high gloss was made favorable and displayed with the following parameter | index.
○: Good Δ: Slightly good ×: Poor Table 3 shows the above results.

  As shown in Table 3, the effect of the dispersant of the present invention was recognized as in the above results. Although the paint of the above example was a light-colored paint diluted with a white paint made of titanium oxide to a concentration of 1/10 and observed the aggregation state of the pigment, no color separation or sedimentation of the pigment was observed. It was.

Examples 33-36
In order to evaluate the effect of the dispersant using the pigment compositions (1) to (4), a CF pixel-forming colorant having the following formulation (4) was prepared.
Formula (4)
Pigment composition (1) to (4) 20.0 parts Polyacrylic acid resin 30.0 parts Thinner 50.0 parts Add the above ingredients into a container, add zirconia beads and disperse with paint conditioner, A colorant for forming a CF pixel was produced.

Comparative Example 8
In place of 20.0 parts of pigment composition (1), C.I. I. Except for using 20.0 parts of PR146, the same operation as in Example 33 was performed to prepare a colored composition for forming a CF pixel to which no dispersant was added.

The fluidity of the colorant for forming a CF pixel of the above example and the gloss of the color development surface were compared with those in the comparative example. The flowability of the colorant and the gloss of the color development surface were measured according to the following method, and the relative evaluation was made with the comparative example.
Flowability: Measured using a B-type viscometer under the conditions of room temperature (25 ° C.) / 30 rpm. Gloss: Using a bar coater (winding thickness: 0.45 mm), the film was developed on a polypropylene film, and the gloss of the developed surface was compared visually and with a gloss meter. In addition, the thing with high gloss was made favorable and was described with the following parameter | index.
○: Good Δ: Slightly good ×: Poor Table 4 shows the above results.

  As shown in Table 4, the colorant using the dispersant of the present invention showed higher fluidity than the comparative example, and the effect of the dispersant of the present invention was recognized.

  Furthermore, the pigment added with the dispersant of the present invention was used for printing inks such as offset inks, various paints such as nitrocellulose lacquer and melamine alkyd paints, and coloring synthetic resins such as vinyl chloride resins. However, the pigment did not aggregate and showed good dispersibility. Recently, the dispersant of the present invention has been used in the production of dry or wet toners for electrophotography, ink for ink jet recording, ink for thermal transfer recording, ink for writing instruments, etc., for which high dispersibility is particularly required. Also in this case, an excellent dispersibility effect by the dispersant of the present invention was recognized.

  The dispersant of the present invention is printing ink (offset ink, gravure ink, etc.), various paints, plastic, pigment printing agent, electrophotographic dry toner or wet toner, ink jet recording ink, thermal transfer recording ink, CF pixel forming For all the vehicles in each application such as resist, ink for writing instruments, etc., in all pigments including organic pigments and inorganic pigments, the fluidity of inks and paints is remarkably improved, and aggregation of pigment particles is prevented. A colored article exhibiting excellent gloss and sharpness can be provided.

Claims (6)

The following dispersant (A), dispersing agent (B), a pigment dispersing agent characterized and Turkey are represented by any of the formulas of the dispersing agent (C), and dispersing agent (D).

A pigment composition comprising a pigment and a pigment dispersant, wherein the pigment dispersant is the pigment dispersant according to claim 1 . The pigment composition according to claim 2 , wherein a blending ratio of the pigment dispersant is 0.05 to 40 parts by mass with respect to 100 parts by mass of the pigment. A pigment colorant comprising the pigment composition according to claim 2 or 3 and a film-forming material. The pigment colorant according to claim 4 , which is an image display colorant, an image recording colorant, a printing ink, a writing ink, a plastic colorant, a pigment textile colorant or a paint colorant. The pigment colorant according to claim 4 , which is a colorant for forming a color filter pixel.