JP5139707B2 - Pigment dispersant, pigment composition and pigment colorant - Google Patents

Description

  The present invention relates to a pigment dispersant, a pigment composition, and a pigment colorant. The pigment colorant is used as a colorant for image display, image recording, printing ink, writing ink, plastic, pigment textile printing, paint, etc., particularly for inkjet ink or electrophotographic developer. It is useful as a color filter colorant.

  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, color filters (hereinafter referred to as CF) used for manufacturing liquid crystal color displays, imaging devices, etc., are three-color pigments of red (R), green (G) and blue (B) in a photosensitive resin liquid. Each of the above pigment dispersions for CF 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 desired pixels on a CF 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 blue pigments include 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.

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 color filters, it has become necessary to improve the transparency of colored pixels, increase the contrast of transmitted light of colored pixels, and increase the pigment concentration of 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.

  Accordingly, the object of the present invention is to display images such as printing inks (offset inks, gravure inks, etc.), various paints, pigment printing agents, color filter colorants, electrophotographic dry toners or wet toners, and ink jet recording inks. In the production of colorants for image recording such as ink for thermal transfer recording and ink for writing instruments, the aggregation of pigment particles dispersed in the colorant such as these inks is prevented, and the above-mentioned inks having excellent fluidity and stability It is to provide a pigment dispersant that enables manufacture.

The above object is achieved by the present invention described below. That is, the present invention provides a pigment dispersant characterized by being selected from a compound represented by the following general formula (1), a quaternary ammonium salt thereof, an amine salt thereof and a metal salt thereof.

(Wherein, M is hydrogen, copper, nickel, zinc, cobalt, aluminum or iron, X is an oxygen atom or -NH-, Ar is a phenyl group or a naphthyl group, and Y is different. a good chlorine or bromine, b is a number from 8 to 15, c represents the number of Yes 1 or 2 in the introduction the number of sulfonic acid groups into the Ar.)

  The present invention also provides a pigment composition comprising a pigment and the pigment dispersant of the present invention. In the pigment dispersant, the blending ratio of the pigment dispersant is preferably 0.05 to 40 parts by mass with respect to 100 parts of the pigment.

The present invention also provides a pigment colorant comprising the above-described pigment composition of the present invention and a film-forming material. Pigment colorant, image display, image recording, printing inks, for writing inks are useful for plastics, pigment printing, or coating, useful as colorants for color filters, especially.

  The present inventors have solved the above-mentioned problems when preparing a color filter colorant (coating liquid) having a high pigment concentration, and are capable of improving the color quality and reducing the viscosity of the color filter coating liquid. As a result of diligent research to develop a dispersant, a specific phthalocyanine compound acts as an excellent pigment dispersant in a smaller amount, can achieve a low viscosity of a color filter coating solution, and can be applied during storage. It has been found that, while preventing liquid thickening and gelation, it also improves the transparency of colored pixels, which is one of the most important characteristics of a color filter.

  The pigment dispersant of the present invention is a high-concentration and low-viscosity stable dispersion of various organic pigments in a dispersion medium such as an image display colorant such as a color filter coating liquid, an image recording colorant, a paint, or a printing ink. Can be dispersed.

  The pigment composition of the present invention is used as a dispersant for a mixture of a plurality of ultrafine pigment pigments having different chemical structures and physical properties, and the resulting dispersion has a low viscosity and is required for long-term storage stability. Useful as a colorant for coating solutions. For example, when it is used for dispersion of a mixed pigment 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 pigment dispersant of the present invention is characterized in that it is a pigment derivative in which a sulfonic acid group is introduced into a halogenated phthalocyanine compound, and the pigment dispersant of the present invention has an excellent affinity for various pigments, It can be used for a wide range of pigments. Moreover, since the pigment dispersant of this invention has the outstanding pigment dispersion effect, it can be used for manufacture of the coloring agent used in various uses.

  The pigment dispersant represented by the general formula (1) and having a sulfonic acid group can be obtained, for example, by reacting a halogenated phthalocyanine and p-phenolsulfonic acid in N-methylpyrrolidone. Further, a compound obtained by reacting a halogenated phthalocyanine and phenol in N-methylpyrrolidone may be sulfonated with a known sulfonating agent such as fuming sulfuric acid according to a conventional method. As the halogenated phthalocyanine, phthalocyanine having 8 to 16 chlorine or bromine which may be different is preferable, and PG7 and PG36 are particularly preferable.

  Examples of the aryl or aralkyl compound having a sulfonic acid group to be introduced into the halogenated phthalocyanine include o-phenolsulfonic acid, m-phenolsulfonic acid, p-phenolsulfonic acid, 4-hydroxy-3-methoxybenzenesulfonic acid, 3 , 5-dichloro-2-hydroxybenzenesulfonic acid, 4-hydroxy-1,3-benzenedisulfonic acid, 5-hydroxy-1,3-benzenedisulfonic acid, 2-hydroxy-7-naphthalenesulfonic acid, 6-hydroxy- 2-naphthalenesulfonic acid, 4-hydroxy-1-naphthalenesulfonic acid, 7-hydroxy-1-naphthalenesulfonic acid, 1-hydroxy-2-naphthalenesulfonic acid, 2-hydroxy-1-naphthalenesulfonic acid, 5-hydroxy- 1-naphthalenesulfonic acid, 4 Hydroxy-2-naphthalenesulfonic acid, 5-hydroxy-2-naphthalenesulfonic acid, 8-hydroxy-2-naphthalenesulfonic acid, 8-hydroxy-1-naphthalenesulfonic acid, 3-hydroxy-2-naphthalenesulfonic acid, 3- Hydroxy-1-naphthalenesulfonic acid, 6-hydroxy-1-naphthalenesulfonic acid, 7-anilino-1-naphthol-3-sulfonic acid, phenyl J acid, 2,4-dinitro-1-naphthol-7-sulfonic acid, 2,4-dinitro-1-naphthol-7-sulfonic acid, 2-hydroxy-4-methoxybenzophenone-5-sulfonic acid, 2,4-dinitro-1-naphthol-7-sulfonic acid, 4-hydroxy-1, 5-Naphthalenedisulfonic acid, 7-hydroxy-1,3-naphthalenedisulfonic acid, 2-hydride Xi-3,6-naphthalenedisulfonic acid, 1-hydroxy-2,3-naphthalenedisulfonic acid, 4-hydroxy-1,3-naphthalenedisulfonic acid, 1-hydroxy-2,5-naphthalenedisulfonic acid, 1-hydroxy- 2,6-naphthalenedisulfonic acid, 1-hydroxy-2,7-naphthalenedisulfonic acid, 8-hydroxy-1,7-naphthalenedisulfonic acid, 4-hydroxy-1,2-naphthalenedisulfonic acid, 5-hydroxy-1, 7-naphthalenedisulfonic acid, 1-hydroxy-3,6-naphthalenedisulfonic acid, 4-hydroxy-2,6-naphthalenedisulfonic acid, 1-hydroxy-3,8-naphthalenedisulfonic acid, 4-hydroxy-1,8- Naphthalenedisulfonic acid, 4-hydroxy-1,7-naphthalenedisulfonic acid, 4- Hydroxy-1,6-naphthalenedisulfonic acid, 5-hydroxy-1,2-naphthalenedisulfonic acid, 8-hydroxy-2,4-naphthalenedisulfonic acid, 5-hydroxy-1,4-naphthalenedisulfonic acid, 5-hydroxy- 2,3-naphthalenedisulfonic acid, 8-hydroxy-1,3-naphthalenedisulfonic acid, 8-hydroxy-1,2-naphthalenedisulfonic acid, 2-hydroxy-1,3-naphthalenedisulfonic acid, 2-hydroxy-1, 4-Naphthalenedisulfonic acid, 2-hydroxy-1,5-naphthalenedisulfonic acid, 2-hydroxy-1,6-naphthalenedisulfonic acid, 2-hydroxy-1,7-naphthalenedisulfonic acid, 2-hydroxy-1,8- Naphthalenedisulfonic acid, 3-hydroxy-1,2-naphthalenedisulfonic acid 6-hydroxy-1,7-naphthalenedisulfonic acid, 3-hydroxy-2,6-naphthalenedisulfonic acid, 7-hydroxy-1,6-naphthalenedisulfonic acid, 3-hydroxy-1,8-naphthalenedisulfonic acid, 3- Hydroxy-1,7-naphthalenedisulfonic acid, 3-hydroxy-1,6-naphthalenedisulfonic acid, 3-hydroxy-1,5-naphthalenedisulfonic acid, 6-hydroxy-1,2-naphthalenedisulfonic acid, 6-hydroxy- 1,3-naphthalenedisulfonic acid, 6-hydroxy-1,4-naphthalenedisulfonic acid, 6-hydroxy-2,3-naphthalenedisulfonic acid, 7-hydroxy-1,2-naphthalenedisulfonic acid, o-aminobenzenesulfonic acid , M-aminobenzenesulfonic acid, sulfanilic acid, o-toluidi -4-sulfonic acid, m-toluidine-4-sulfonic acid, p-toluidine-2-sulfonic acid, o-anisidine-5-sulfonic acid, 3-amino-6-methoxybenzenesulfonic acid, 2-amino-5 Methoxybenzenesulfonic acid, 4-amino-3-methoxybenzenesulfonic acid, 2-amino-4-methoxybenzenesulfonic acid, 3-nitroaniline-4-sulfonic acid, 4-chloroaniline-3-sulfonic acid, 2,5 -Dichlorosulfanilic acid, 4,5-dichloroaniline-2-sulfonic acid, 4-acetamido-2-aminobenzenesulfonic acid, 4-amino-2-chlorotoluene-5-sulfonic acid, 5-amino-2-chlorotoluene -4-sulfonic acid, 3-amino-6-chloro-4-sulfobenzoic acid, 2-amino-1,4-benzenedisulfonic acid, 2-amino-1,5-benzenedisulfonic acid, 3-amino-1,2-benzenedisulfonic acid, 4-amino-1,2-benzenedisulfonic acid, 2-amino-1,3-benzenedisulfonic acid, 5- Amino-1,3-benzenedisulfonic acid, 2-amino-1-naphthalenesulfonic acid, 6-amino-1-naphthalenesulfonic acid, 1-amino-2-naphthalenesulfonic acid, 8-amino-1-naphthalenesulfonic acid, 6-amino-2-naphthalenesulfonic acid, 4-amino-1-naphthalenesulfonic acid, 5-amino-1-naphthalenesulfonic acid, 8-amino-2-naphthalenesulfonic acid, 5-amino-2-naphthalenesulfonic acid, 2-amino-7-naphthalenesulfonic acid, 2-amino-8-naphthalenesulfonic acid, 4-amino-2-naphthalenesulfonic acid, -Amino-2-naphthalenesulfonic acid, 3-amino-1-naphthalenesulfonic acid, 2-amino-1,5-naphthalenedisulfonic acid, 4-amino-1,7-naphthalenedisulfonic acid, 4-amino-1,6 -Naphthalenedisulfonic acid, 1-amino-2,7-naphthalenedisulfonic acid, 3-amino-1,5-naphthalenedisulfonic acid, 7-amino-1,3-naphthalenedisulfonic acid, 4-amino-2,5-naphthalene Disulfonic acid, 1-amino-3,6-naphthalenedisulfonic acid, 3-amino-2,7-naphthalenedisulfonic acid, 6-amino-1,3-naphthalenedisulfonic acid, 4-amino-1,5-naphthalenedisulfonic acid 1-amino-2,3-naphthalenedisulfonic acid, 4-amino-1,3-naphthalenedisulfonic acid, 1-amino-2,5 Naphthalenedisulfonic acid, 1-amino-2,6-naphthalenedisulfonic acid, 8-amino-1,7-naphthalenedisulfonic acid, 4-amino-1,2-naphthalenedisulfonic acid, 4-amino-2,8-naphthalenedisulfonic acid Acid, 4-amino-2,6-naphthalenedisulfonic acid, 4-amino-1,8-naphthalenedisulfonic acid, 5-amino-1,2-naphthalenedisulfonic acid, 5-amino-1,3-naphthalenedisulfonic acid, 5-amino-1,4-naphthalenedisulfonic acid, 5-amino-2,3-naphthalenedisulfonic acid, 8-amino-1,3-naphthalenedisulfonic acid, 8-amino-1,2-naphthalenedisulfonic acid, 2- Amino-1,3-naphthalenedisulfonic acid, 2-amino-1,4-naphthalenedisulfonic acid, 2-amino-1,6-naphtha Rangesulfonic acid, 2-amino-1,7-naphthalenedisulfonic acid, 2-amino-1,8-naphthalenedisulfonic acid, 3-amino-1,2-naphthalenedisulfonic acid, 6-amino-1,7-naphthalenedisulfonic acid Acid, 3-amino-2,6-naphthalenedisulfonic acid, 3-amino-2,5-naphthalenedisulfonic acid, 3-amino-1,8-naphthalenedisulfonic acid, 3-amino-1,7-naphthalenedisulfonic acid, 3-amino-1,6-naphthalenedisulfonic acid, 6-amino-1,2-naphthalenedisulfonic acid, 6-amino-1,4-naphthalenedisulfonic acid, 6-amino-2,3-naphthalenedisulfonic acid, 7- Amino-1,2-naphthalenedisulfonic acid, 4- (aminomethyl) benzenesulfonic acid, 4- (aminomethyl) -2-methylben Such as Nsuruhon acid, and the like.

  Examples of the aryl or aralkyl compound having no sulfonic acid group introduced into the halogenated phthalocyanine include phenol, o-cresol, m-cresol, p-cresol, 2,3-dimethylphenol, 2,4-dimethylphenol, 2,5-dimethylphenol, 2,6-dimethylphenol, 3,4-dimethylphenol, 3,5-dimethylphenol, 2-ethylphenol, 3-ethylphenol, 4-ethylphenol, 2-methoxyphenol, 3- Methoxyphenol, 4-methoxyphenol, 2,6-dimethoxyphenol, 2-chlorophenol, 3-chlorophenol, 4-chlorophenol, 2,3-dichlorophenol, 2,4-dichlorophenol, 2,5-dichlorophenol 2,6-jik Rophenol, 3,4-dichlorophenol, 3,5-dichlorophenol, 1-naphthol, 2-naphthol, 4-chloro-1-naphthol, 2,4-dichloro-1-naphthol, aniline, o-toluidine, m -Toluidine, p-toluidine, 2,4-xylidine, 3,4-xylidine, p-cresidine, o-anisidine, m-anisidine, p-anisidine, anthranilic acid, p-aminobenzoic acid, o-nitroaniline, m -Nitroaniline, p-nitroaniline, o-chloroaniline, m-chloroaniline, p-chloroaniline, 2,5-dichloroaniline, 3,4-dichloroaniline, 3,5-dichloroaniline, 2,4,5 -Trichloroaniline, 2-chloro-4-nitroaniline, 5-chloro-2-nitroaniline, 2,6- Chloro-4-nitroaniline, o-fluoroaniline, 2,4-difluoroaniline, m-trifluoromethylaniline, 2-chloro-5-trifluoromethylaniline, 1-naphthylamine, 2-naphthylamine, 1-amino-2 -Methylnaphthalene, 1-amino-4-bromonaphthalene, 4-nitro-1-naphthylamine, 1-amino-4-nitronaphthalene, benzyl alcohol, 2-methylbenzyl alcohol, 3-methylbenzyl alcohol, 4-methylbenzyl alcohol 1-naphthalenemethanol, 2-naphthalenemethanol, benzylamine, 2-methylbenzylamine, 3-methylbenzylamine, 4-methylbenzylamine, 1-naphthylmethylamine, 2-naphthylmethylamine and the like.

  The reaction between the halogenated phthalocyanine and the aryl or aralkyl compound can be carried out by dehydrohalogenation condensation, and any method capable of dehydrohalogenation is effective. Particularly preferred methods are N- It is obtained by dissolving or suspending in methylpyrrolidone and reacting at a temperature of 130 to 200 ° C. for 3 to 24 hours in the presence of sodium carbonate. If the aryl or aralkyl compound does not have a sulfonic acid group, the product can be obtained by sulfonation with a sulfonating agent such as fuming sulfuric acid.

  Examples of the amine that forms an amine salt with the compound represented by the general formula (1) include (mono, di, or tri) alkylamines, substituted or unsubstituted alkylenediamines, alkanolamines, and alkylammoniums. Although 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 mixing ratio of the pigment dispersant of the present invention to the pigment 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. When the blending ratio of the pigment dispersant is too small, it is difficult to sufficiently obtain the effect of the intended dispersant. In addition, if the blending ratio of the pigment dispersant is too large, the effect of using only a large amount cannot be obtained. On the contrary, as a result, the physical properties of the paint or ink vehicle using the obtained pigment composition are lowered. In addition, the hue of the pigment to be dispersed greatly changes depending on the color of the pigment dispersant itself.

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

The method for using the pigment dispersant of the present invention is not particularly limited, and examples thereof include the following methods.
(1) A pigment and a pigment dispersant are mixed in advance by a known method, and the obtained pigment composition is added to a vehicle or the like and dispersed in the vehicle.
(2) When dispersing the pigment in the vehicle or the like, the pigment and the pigment dispersant are separately added to the vehicle or the like at a predetermined ratio and dispersed in the vehicle.
(3) The pigment and the pigment dispersant are separately dispersed in a vehicle or the like, and then the obtained dispersions are mixed and dispersed at a predetermined ratio.
(4) A pigment dispersant is added to a dispersion obtained by dispersing the pigment in a vehicle or the like at a predetermined ratio to disperse the pigment.
Any of these methods can achieve the desired pigment dispersion effect. Further, in the above methods (1) to (4), a method of adding and dispersing a polymer (polymer dispersing agent) having an ionic group (counter ionic group) of the ionic group counter of the pigment dispersant. Is preferred. More effectively, a dispersion method using the method (1) or (2) in combination with a polymer having a counterionic group is desirable.

  The pigment composition containing the pigment dispersant of the present invention can be produced by mixing the pigment and the pigment dispersant by a conventionally known method, and the production method is not particularly limited. For example, a method of mixing pigment powder and pigment dispersant powder without using a disperser: mechanically mixing the pigment and pigment dispersant with various dispersers such as kneaders, rolls, attritors and horizontal bead mills Method of adding: Mixing or mixing a solution in which the pigment dispersant of the present invention is dissolved or finely dispersed in a pigment suspension such as water-based or organic solvent-based, and uniformly depositing the pigment dispersant on the pigment surface: sulfuric acid, etc. There is a method in which a pigment and a pigment dispersant are dissolved in a solvent having strong dissolving power and then co-precipitated with a poor solvent such as water. Thus, when preparing a pigment composition, the pigment 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 used for image display, image recording, and printing. Used as a colorant for inks, writing inks, plastics, pigment printing, paints, etc. In particular, it is used as a color filter colorant as an image display material, and as an image recording agent, for example, an inkjet ink or an electrodeposition recording liquid, and as an electrophotographic developer, an inkjet recording method, an electrodeposition recording method, an electrophotographic method, It is used for the image recording method.

  A color filter dispersion (colorant) will be described as an example of the image display material. When preparing the dispersion, the pigment composition of the present invention is premixed as necessary, for example, by adding a cationic polymer dispersant to an organic solvent solution containing an appropriate film-forming resin, Distributed processing. For example, the pigment composition and the cationic polymer dispersant are uniformly mixed and ground by a dispersion machine such as a vertical medium disperser, a horizontal medium disperser, or a ball mill, and this is a liquid containing a film-forming polymer. The pigment, the pigment dispersant of the present invention and the cationic polymer dispersant are dissolved in sulfuric acid and the like, and then the sulfuric acid solution is precipitated in water, so that the pigment and the pigment dispersant are mixed into a solid solution or a co-solution. In the same manner as above, the obtained pigment composition was added to and mixed with a liquid containing a film-forming polymer, a cationic polymer dispersant, etc., and a horizontal wet medium disperser (bead mill) such as Dino Mill. ) And the like.

  In the present invention, as a liquid containing a film-forming material for making a pigment dispersion, a film-forming polymer used in a conventionally known pigment dispersion for color filters 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 dispersing aid, a smoothing agent, and an adhesive agent, can be added to a pigment dispersion as needed.

  The addition 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.

  Further, a photo-curable photosensitive pigment dispersion can be obtained by adding a photopolymerization initiator such as benzoin ether or benzophenone to a pigment dispersion containing a photosensitive resin, and carrying out a brickwork by a conventionally known method. Moreover, it can replace with said photoinitiator and can use it as a thermosetting pigment dispersion liquid 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 examples and comparative examples. In the text, “part” or “%” is based on mass unless otherwise specified.
Example 1
20 parts of PG36, 4.5 parts of p-phenolsulfonic acid and 17 parts of potassium carbonate are added to 100 parts of N-methylpyrrolidone and stirred at 180-185 ° C. for 8 hours. After cooling, the mixture was filtered, washed with methanol, washed with water, and dried at 80 ° C. to obtain 18.5 parts of the following pigment dispersant (A).

Reference example 2
20 parts of PG36, 3.7 parts of 1-naphthol and 17 parts of potassium carbonate are added to 100 parts of N-methylpyrrolidone and stirred at 180-185 ° C. for 8 hours. After cooling, it was filtered, washed with methanol and water, and dried at 80 ° C. to obtain 18.5 parts of a reaction product. 10 parts of this reaction product was dissolved in 50 parts of 20% fuming sulfuric acid and reacted at 20-25 ° C. for 6 hours. After cooling, the reaction mixture was precipitated in ice water, filtered and washed with water to obtain 56 parts (pure amount 11 parts) of the following pigment dispersant (B). This paste was dried, and 11 parts of a pigment dispersant (B) having an average of one sulfonic acid group introduced per molecule was obtained by elemental analysis.

Example 3
18.5 parts of the following pigment dispersant (C) was obtained in the same manner as in Example 1 except that sulfanilic acid was used in place of the p-phenolsulfonic acid of Example 1.

Reference example 4
Except using 1-naphthylamine in place of 1-naphthol Example 2 to give the following pigment dispersant (D) 11 parts In the same manner as in Reference Example 2.

Example 5
240 parts of water was added to 90 parts (pure amount: 18 parts) of the pigment dispersant (A) paste of Example 1, and the mixture was stirred at 25 ° C. for 1 hour. To this was added 7 parts of tetrabutylammonium chloride, stirred for 1 hour, filtered, washed with water and dried to obtain 17 parts of the following pigment dispersant (E).

Reference Example 6
18 parts of the following pigment dispersant (F) was obtained in the same manner as in Example 5 except that the pigment dispersant (B) was used instead of the pigment dispersant (A) in Example 5.

Example 7 (Preparation of pigment composition (1))
Add 19.0 parts of PG36 to 1000 parts of water and disperse to make a slurry. Thereto is added a slurry obtained by dispersing 1.0 part of the pigment dispersant (A) obtained in 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 adjusted 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.

Reference Example 8 (Preparation of pigment composition (2))
Add 19.0 parts of PG36 to 1000 parts of water and disperse to make a slurry. Thereto is added a slurry of 1.0 part of the pigment dispersant (B) obtained in Reference Example 2, 0.9 part of tetrabutylammonium chloride 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, filtered, dried, and pulverized to obtain Pigment composition (2) 20 parts.

Example 9 (Preparation of pigment composition (3))
A pigment composition (3) was obtained in the same manner as in Example 7, except that the pigment dispersant (C) obtained in Example 3 was used instead of the pigment dispersant (A).

Reference Example 10 (Preparation of pigment composition (4))
A pigment composition (4) was obtained in the same manner as in Example 7, except that the pigment dispersant (D) obtained in Reference Example 4 was used instead of the pigment dispersant (A).

Example 11 (Preparation of pigment composition (5))
A pigment composition (5) was obtained in the same manner as in Example 7, except that the pigment dispersant (E) obtained in Example 5 was used instead of the pigment dispersant (A).

Reference Example 12 (Preparation of pigment composition (6))
A pigment composition (6) was obtained in the same manner as in Example 7, except that the pigment dispersant (F) obtained in Reference Example 6 was used instead of the pigment dispersant (A).

Examples 13 , 15, and 17, Reference Examples 14, 16, and 18
In order to evaluate the effect of the pigment dispersant using the pigment compositions (1) , (3), and (5 ), color filter colorants having the following composition (1) were prepared (Examples 13 and 15, 17) . Similarly, using the pigment compositions (2), (4), and (6), color filter colorants having the following formulation (1) were prepared (Reference Examples 14, 16, and 18).
Formulation (1)
-Any of pigment compositions (1) to (6) 20.0 parts-Polyacrylic acid resin 30.0 parts-Thinner 50.0 parts Add the above ingredients into a container, add zirconia beads, and paint conditioner Dispersed to prepare a color filter colorant.

Examples 19 , 21, 23, Reference Examples 20, 22, 24
In order to evaluate the effect of combined use of the cationic polymer dispersant using the pigment compositions (1) , (3), (5) and the cationic polymer dispersant, respectively, for the color filter of the following formulation (2) Colorants were prepared (Examples 19, 21, and 23) . Similarly, a color filter colorant having the following composition (1) was prepared using the pigment compositions (2), (4), (6) and the cationic polymer dispersant (Reference Examples 20, 22, 24). .
Formula (2)
-Any of pigment compositions (1) to (6) 20.0 parts-Cationic polymer dispersant 4.0 parts-Polyacrylic acid resin 30.0 parts-Thinner 46.0 parts Then, zirconia beads were added and dispersed with a paint conditioner to prepare a colorant for a color filter.

Comparative Example 1
Pigment composition (1) Instead of 20.0 parts, the same procedure as in Example 19 was carried out except that 20.0 parts of PG36 was used, and a color filter colorant to which no pigment dispersant was added was obtained. Produced.

The fluidity of the colorant for color filter and the gloss of the color development surface of the examples and comparative examples were compared with those of 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 (viscosity change)>
The viscosity (mPa · s) of the color filter colorant in Examples and Comparative Examples immediately after production and after 7 days at 25 ° C. was measured using an E-type viscometer at room temperature (25 ° C.) and a rotor rotation speed of 6 rpm. It was measured.
<Gloss>
Using a bar coater (winding thickness: 0.45 mm), color was developed on a polypropylene film, and the gloss of the color development surface was compared visually and with a gloss meter. In addition, the thing with high gloss was made favorable, and the evaluation result was displayed as follows.
○: Good Δ: Slightly good ×: Poor The results are shown in Table 1.

  As shown in Table 1, the color filter colorant using the pigment dispersant of the present invention exhibits higher fluidity than the comparative example, and when the cationic polymer dispersant is used in combination. Further, it exhibited high fluidity, good gloss, and the effect of the pigment dispersant of the present invention was recognized.

  Furthermore, the pigment added with the pigment dispersant of the present invention was used for printing inks such as offset inks, various paints such as nitrocellulose lacquers and melamine alkyd paints, and coloring synthetic resins such as vinyl chloride resins. In this case, the pigment did not aggregate and showed good dispersibility. In addition, recently, the pigment dispersant of the present invention was used for the production of dry toner or wet toner for electrophotography, ink for ink jet recording, ink for thermal transfer recording, ink for writing instruments, etc., for which high dispersibility is particularly required. Even in these cases, the effect of excellent dispersibility by the pigment dispersant of the present invention was recognized.

  The pigment dispersant of the present invention is a high-concentration and low-viscosity stable dispersion of various organic pigments in a dispersion medium such as an image display colorant such as a color filter coating liquid, an image recording colorant, a paint, or a printing ink. Can be dispersed.

Claims (6)

A pigment dispersant characterized by being a compound represented by the following general formula (1), a quaternary ammonium salt thereof, an amine salt thereof or a metal salt thereof.

(Wherein, M is hydrogen, copper, nickel, zinc, cobalt, aluminum or iron, X is an oxygen atom or -NH-, Ar is a phenyl group or a naphthyl group, and Y is different. a good chlorine or bromine, b is a number from 8 to 15, c represents the number of Yes 1 or 2 in the introduction the number of sulfonic acid groups into the Ar.)   A pigment composition comprising a pigment and the pigment dispersant according to claim 1.   The pigment composition according to claim 2, wherein the blending ratio of the pigment dispersant is 0.05 to 40 parts by mass with respect to 100 parts of the pigment.   A pigment colorant comprising the pigment composition according to claim 2 and a film-forming material.   The pigment colorant according to claim 4, which is used for image display, image recording, printing ink, writing ink, plastic, pigment printing or paint. Pigment colorant of claim 5 which is a color filter for coloring agent.