JP2001031900A - Dispersion composition and method for producing the same - Google Patents

Abstract

PROBLEM TO BE SOLVED: To improve dispersion stability and solve the problem of sedimentation, to widen the range of organic solvents and insoluble particulate matter, and to be widely used, especially for liquid developers and jet inks utilizing electrostatic force. The present invention provides a dispersion composition useful for: A dispersion composition comprising a particulate material dispersed in an organic solvent contains at least a polymer compound having an acidic group and a polymer compound having a basic group, and at least a part of the polymer compound is an organic compound. A dispersion composition that is insoluble in a solvent and that a polymer compound is adsorbed on at least a part of the particulate matter.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a technical field in which particulate matter insoluble in an organic solvent is dispersed and used, for example, a paint, a printing ink, and a liquid developer in which a pigment or dye as a particulate substance is dispersed and used. The present invention relates to a dispersion composition and a method for producing the same, which can be used in the field of (liquid toner) and ink-jet ink, in the field of dispersing and using pharmaceuticals as granular substances, and in the field of dispersing and using catalysts and polymerization initiators as particulate substances. Things. Further, the present invention relates to a dispersion composition which can be used in the field of a coloring material containing a particulate substance in a polymer compound by drying, for example, a dry toner, a powder coating, a plastic, and the like, and a method for producing the same.

[0002]

2. Description of the Related Art Hitherto, in the field of dispersing and using pigments and dyes insoluble in organic solvents, various attempts have been made to make the dispersed particle size finer and to improve the storage stability. For example, in British Patent No. 20010883, a specific polyesteramine is used as a pigment dispersant in paints and inks, and in JP-A-10-265728, a pigment coated with a thin film of a thermosetting polymer having a methylol group is used for inkjet. It has been proposed as a coloring composition. Further, Japanese Unexamined Patent Publication No.
No. 30040 proposes a liquid developer in which urethane-based microencapsulated colored resin particles containing a pigment or a dye are dispersed in a non-aqueous solvent. Furthermore, JP-T-11-501353 proposes a dispersant for an inkjet printer containing a dispersant containing a basic group or an acidic group and a neutralizing agent for the group in a non-destabilizing amount. .

[0003]

However, in a dispersion composition using a general dispersion stabilizer or the above-mentioned pigment dispersant, types of organic solvents and pigments are limited. Although the dispersion of the pigment is stabilized by the steric repulsion of the resin, the amount of charge generation on the pigment surface is small, so if stored in a dilute pigment dispersion for a long time, sedimentation will occur and the dispersion stability will be lacking. I was Furthermore, when used in a liquid developer, the coloring composition of the pigment covered with the thermosetting polymer or the coloring resin particles of the urethane-based microcapsule have a particle size of 0.5 μm or more, and are used for long-term storage. Has settling problems. On the other hand, in the case of a dispersion ink for an inkjet printer using a dispersant containing a basic group or an acidic group and a neutralizing agent thereof, the amount of adsorption is small because the dispersant is dissolved in the solution, and the storage stability is not necessarily satisfied. It was not a thing.
Further, since the adsorption and desorption of the dispersant are repeated, the charge stability is also unstable.

An object of the present invention is to improve the dispersion stability of particulate matter and solve the problem of sedimentation, solve the problem of charge stability, and widen the types of organic solvents and insoluble particulate matter.
It is an object of the present invention to provide a dispersion composition useful for a liquid developer or a jet ink which uses a wide range of applications, particularly, an electrostatic force.

[0005]

Means for Solving the Problems The inventors of the present invention have conducted intensive studies to solve the above-mentioned problems, and as a result, it has been found that, in a dispersion obtained by dispersing a particulate material in an organic solvent, a polymer compound having at least an acidic group is contained. And a high molecular compound having a basic group, wherein at least one of the high molecular compounds is insoluble in the organic solvent, and the high molecular compound is adsorbed on the particulate matter. By providing the dispersion composition, the steric repulsion between the particulate matter is increased by a large amount of the polymer compound adsorbed, and the sedimentation of the particulate matter is prevented by being finely divided, thereby improving the dispersion stability, Further, they have found that charges can be generated on the surface of the granular material and can be stably maintained, and the present invention has been accomplished.

[0006] Further, a method for producing the dispersion composition of the present invention includes a dispersion in which a granular substance is dispersed in an organic solvent using a polymer compound having an acidic group, and an organic solvent in which the polymer compound having an acidic group is not dissolved. A polymer compound having an acidic group and / or a polymer compound having a basic group is adsorbed on a granular substance by mixing with a dispersion liquid in which a polymer compound having a basic group is dissolved or dispersed, or A dispersion in which a granular substance is dispersed in an organic solvent using a polymer compound having an acidic group, and a polymer compound having an acidic group are dissolved or dispersed in an organic solvent in which the polymer compound having a basic group does not dissolve. The dispersion composition is formed by adsorbing the polymer compound having a basic group and / or the polymer compound having an acidic group on the particulate matter by mixing with the dispersion. To provide things.

[0007]

BEST MODE FOR CARRYING OUT THE INVENTION The dispersion composition of the present invention comprises a particulate substance, a high molecular compound having an acidic group and a high molecular compound having a basic group, and an organic solvent used in the dispersion composition. It is essential that some of the polymer compounds be insoluble. Further, the amount of the polymer compound having an acidic group and the polymer compound having a basic group adsorbed on the granular material is preferably in the range of 20 to 10000 parts by weight, more preferably 40 to 10,000 parts by weight, based on 100 parts by weight of the granular material.
5000 parts by weight is more preferred. If the amount adsorbed is less than 20 parts by weight, the dispersion stability is exerted. If the amount exceeds 10,000 parts by weight, the content of the particulate matter in the dispersion composition is reduced, and the particulate matter sufficient for use in paints, inks, toners and the like is reduced. It is difficult to obtain a concentration of

[0008] In the dispersion composition of the present invention, the more preferable range of the adsorption amount of the high molecular compound having an acidic group and the high molecular compound having a basic group with respect to the granular material is 30 parts by weight with respect to 100 parts by weight of the granular material. The range is from 1 to 10,000 parts by weight.

The number average molecular weight of the high molecular compound having an acidic group is preferably in the range of 1,000 to 50,000. If the number average molecular weight is less than 1,000, the acid strength of the acidic group becomes strong, and it takes a salt structure with the polymer compound having a basic group, causing no charge generation or causing aggregation of dispersed particulate matter. On the other hand, when the molecular weight exceeds 50,000, it is difficult to dissolve in a solvent, and the viscosity of the dispersion composition becomes extremely high. A more preferred range is 3,000 to 30,000.

The number average molecular weight of the high molecular compound having a basic group is preferably in the range of 1,000 to 50,000. If the number average molecular weight is less than 1,000, the basic strength of the basic group is increased, the salt has a salt structure with the polymer compound having an acidic group, and no charge is generated or aggregation of dispersed particulate matter is caused. On the other hand, when the molecular weight exceeds 50,000, it is difficult to dissolve in a solvent, and the viscosity of the dispersion composition becomes extremely high. A more preferred range is 3,000 to 30,000.

The acidic group is not particularly limited, but includes a carboxyl group, a sulfonic acid group, a phosphonic acid group, and the like. In particular, a carboxyl group having a weak acid strength is more preferable since aggregation of the dispersion composition hardly occurs. .

The acid value of the polymer having an acidic group is preferably in the range of 5 to 200 KOH mg / g. If the acid value is less than 5 KOHmg / g, a sufficient zeta potential cannot be obtained, resulting in poor stability of the dispersion, or a beautiful image cannot be obtained when used for a toner. Also, 2
If it exceeds 00 KOH mg / g, the acid strength becomes strong, it takes a salt structure with the polymer compound having a basic group, and does not generate electric charge or causes aggregation of dispersed particulate matter. A more preferred range is 10 to 150 KOHmg / g.
It is.

The basic group is not particularly restricted but includes primary, secondary, tertiary and quaternary amino groups.
Particularly, a tertiary amino group is more preferable from the viewpoint of easy ionization. The amine value of the polymer compound having a basic group is preferably in the range of 5 to 200 KOHmg / g. When the amine value is 5 KOHmg / g or less, a sufficient zeta potential is not obtained, and the stability of the dispersion is poor, and when used in a toner, a beautiful image cannot be obtained. On the other hand, if it exceeds 200, the strength of the base becomes too strong to form a salt structure with the polymer compound having a basic group, so that no charge is generated or aggregation of dispersed particulate matter is caused.
A more preferred range is from 10 to 150 KOHmg / g.

The particle size of the particulate matter in the dispersion composition of the present invention is preferably in the range of 1.0 to 0.01 μm, more preferably 0.5 to 0.01 μm.
The range of 0.01 μm is more preferable, and the range of 0.3 to 0.01 μm is most preferable from the viewpoint of the sedimentation of the particulate matter.

As described above, in the present invention, a particulate material is adsorbed on a polymer compound having an acidic group or an insoluble solvent in an organic solvent in a polymer compound having a basic group, and the particulate material is dispersed. Although it is to stabilize, from the viewpoint of dispersion stability to various solvents, if the polymer compound is crosslinked in the adsorption step and adsorbed to the particulate matter, it is possible to further improve the dispersion stability. it can.

The method of crosslinking is not particularly limited, and examples thereof include an ester bond, an amino bond, a urethane bond, an ether bond, and a C—C bond by a radical reaction. From the viewpoint of stability at the time, an ester bond and an amino bond are particularly preferable.

As a method for crosslinking a polymer compound having an acidic group and a polymer compound having a basic group, a method using a crosslinking agent, a polymer compound having an acidic group and a polymer compound having a basic group, A method of introducing a cross-linking functional group into one of them is mentioned. The crosslinking agent is not particularly limited as long as it reacts with an acidic group or a basic group in the polymer compound.For example, a melamine resin, an amino resin such as a benzoguanamine resin or a urea resin, a tolylene diisocyanate prepolymer, Isocyanate resins such as polyfunctional aromatic polyisocyanate, diphenylmethane diisocyanate, hexamethylene diisocyanate prepolymer, xylene diisocyanate prepolymer and lysine isocyanate prepolymer, acrylic resins having bisphenol A and glycidyl groups, etc. And chelate compounds such as Ti, Al, and Zr. Among these, amino resins and epoxy resins are particularly preferred in terms of reaction rate, reaction temperature and the like.

Examples of the cross-linking functional group introduced into the polymer compound having an acidic group and the polymer compound having a basic group include an amino group, a hydroxyl group, a methoxy group, and a glycidyl group. Among them, a hydroxyl group and a glycidyl group are particularly preferable in terms of reaction rate and reaction temperature.

As a method for introducing a functional group for crosslinking, a known general method can be used. For example, when a polymer compound having an acidic group or a polymer compound having a basic group is synthesized, A method of polymerizing or condensing using a monomer containing a functional group, a polyhydric alcohol, hydroxyamine, polyamine, or the like, or crosslinking after synthesizing a prepolymer of a polymer compound having an acidic group or a polymer compound having a basic group. Examples of the method include a method of introducing a functional group by polymerization, condensation or addition reaction.

Examples of the monomer having a crosslinking functional group used in synthesizing a polymer compound having an acidic group and a polymer compound having a basic group include 2-hydroxyethyl acrylate, 2-hydroxyethyl methacrylate, and acrylic acid. Hydroxyl-containing monomers such as hydroxypropyl acrylate, hydroxypropyl methacrylate, glycerol monomethacrylate, polyethylene glycol monomethacrylate, propylene glycol monomethacrylate, glycidyl groups such as glycidyl acrylate and glycidyl methacrylate; Monomer containing methoxy group such as methoxy polyethylene glycol acrylate and methoxy polyethylene glycol methacrylate , Acrylamide, amino group-containing monomers such as methacrylic amide. Examples of polyhydric alcohols include ethylene glycol, propylene glycol, neopentin glycol, dihydric alcohols such as decanediol and dodecanediol, trihydric alcohols such as trimethylolpropane, pentaerthritol and glycerin, and polyester polyols. Polymer polyols such as polyether polyol, polyamide diol, and polycaprolactone diol are exemplified. Examples of the hydroxyamine include amino alcohol, diethanolamine, triethanolamine, trihydroxymethylaminomethane, and polyamines such as aminophenol.
Diethylenetriamine, triethylenetetramine, tetraethylenepentamine, metaphenylenediamine, metaphenylenediamine, diaminodiphenylmethane, diaminodiphenylsulfone, metaxylenediamine, metaminobenzylamine, benzidine, bis (3,4-diaminophenyl) sulfone, , 6-diaminopyridine and the like.

In a method of synthesizing a prepolymer of a polymer compound having an acidic group or a polymer compound having a basic group and then introducing a functional group for crosslinking by polymerization, condensation or addition reaction, Compounds having a functional group for crosslinking to be introduced by reaction include:
Although it is not particularly limited, it is only necessary to have two or more reactive groups, and examples thereof include polyhydric alcohol, polyamine, hydroxyamine, bisphenol A, and polyisocyanate.

The method for measuring the amount of polymer compound adsorbed on the particulate matter can be determined by a known general method. The dispersion composition is subjected to centrifugation until the supernatant is transparent, and the resin concentration in the supernatant is determined. By measuring, it can be measured indirectly.

The particulate matter is not limited to inorganic pigments, organic pigments, dyes that do not dissolve in a solvent, fillers, medicines, polymerization initiators, catalysts, ultraviolet absorbers, etc., unless they are dissolved in an organic solvent.

Examples of the inorganic pigments include carbon black, titanium oxide, zinc white, zinc oxide, tripon, iron oxide, aluminum oxide, silicon dioxide, kaolinite,
Montmorillonite, talc, barium sulfate, calcium carbonate, silica, alumina, cadmium red, red iron oxide, molybdenum red, chrome vermillion, molybdate orange, graphite, chrome yellow, cadmium yellow, yellow iron oxide, titanium yellow, chromium oxide, pyridian , Cobalt green, titanium cobalt green,
Examples thereof include cobalt chrome green, ultramarine blue, ultramarine blue, navy blue, cobalt blue, cerulean blue, manganese violet, cobalt violet, and mica.

Examples of the organic pigment include azo, azomethine, polyazo, phthalocyanine, quinacridone, anthraquinone, indigo, thioindigo, quinophthalone, benzimidazolone, isoindoline, and isoindolinone. And the like.

Examples of the dye which does not dissolve in a solvent include, for example,
Examples include azo-based, anthraquinone-based, indigo-based, phthalocyanine-based, carbonyl-based, quinone-imine-based, methine-based, quinoline-based, and nitro-based ones, and among these, disperse dyes are particularly preferred.

The types of the high molecular compound having an acidic group and the high molecular compound having a basic group are not particularly limited, but include acrylic, polyester, polyurethane, and the like.
Epoxy type, amino type and the like can be mentioned, and these may be used in combination. Among these types, an acrylic type and a polyester type are particularly preferable because of ease of synthesis and ease of introduction of an acidic group and a basic group. Further, there is no problem even if the amphoteric polymer compound has both an acidic group and a basic group.

The method for producing the acrylic polymer compound having an acidic group is not particularly limited. For example, a monomer having an acidic group and another polymerizable monomer are mixed in a non-reactive solvent.
Examples thereof include those obtained by reacting in the presence or absence of a catalyst, and among them, those obtained by polymerizing a monomer having an acidic group and a C8 or higher (meth) acrylate monomer as essential components are preferable.

The method for producing the acrylic polymer compound having a basic group is not particularly limited. For example, a monomer having a basic group and another polymerizable monomer may be prepared in a non-reactive solvent in the presence or absence of a catalyst. And a monomer obtained by reacting in the presence of an acid group.
A polymer obtained by polymerizing the above (meth) acrylate monomer as an essential component is preferable.

Examples of the acrylic monomer having an acidic group used herein include acrylic acid, methacrylic acid, crotonic acid, ethacrylic acid, propylacrylic acid, isopropylacrylic acid, itaconic acid, fumaric acid, acroyloxyethyl phthalate, and acroyloxyethyl phthalate. Monomers having a carboxyl group such as yloxysuccinate; monomers having a sulfonic acid group such as ethyl acrylate 2-ethyl sulfonic acid, ethyl methacrylate 2-ethyl sulfonic acid; butyl acrylamide sulfonic acid; ethyl methacrylate 2-ethyl phosphonate And monomers having a phosphonic acid group, such as ethyl 2-phosphonate and acrylic acid. Among them, acrylic acid and methacrylic acid are preferable.

The monomer having a basic group has a primary amino group such as acrylamide, aminoethyl acrylate, aminopropyl acrylate, methacrylamide, aminoethyl methacrylate and aminopropyl methacrylate. Monomers, methylaminoethyl acrylate, methylaminopropyl acrylate, ethylaminoethyl acrylate, ethylaminopropyl acrylate, methylaminoethyl methacrylate, methylaminopropyl methacrylate, ethylaminoethyl methacrylate, ethylaminopropyl methacrylate, etc. Monomers having a secondary amino group such as dimethylaminoethyl acrylate, diethylaminoethyl acrylate, dimethylaminopropyl acrylate, diethylaminopropyl acrylate, methacryl Monomers having a tertiary amino group, such as dimethylaminoethyl, diethylaminoethyl methacrylate, dimethylaminopropyl methacrylate, diethylaminopropyl methacrylate, etc., dimethylaminoethyl methyl acrylate acrylate, dimethylaminoethyl methyl methacrylate, Monomers having a quaternary amino group such as dimethylaminoethyl benzyl acrylate chloride salt and dimethylaminoethyl benzyl methacrylate chloride salt are exemplified.

Examples of C8 or higher (meth) acrylate monomers include 2-ethylhexyl acrylate, 2-ethylhexyl methacrylate, octyl acrylate, octyl methacrylate, lauryl acrylate, lauryl methacrylate, cetyl acrylate, Examples include cetyl methacrylate, stearyl acrylate, stearyl methacrylate, behenyl acrylate, and behenyl methacrylate.

Other polymerizable monomers include, for example, methyl acrylate, ethyl acrylate, isopropyl acrylate, n-propyl acrylate, and n-acrylic acid.
-Butyl, t-butyl acrylate, benzyl acrylate, methyl methacrylate, ethyl methacrylate, isopropyl methacrylate, n-propyl methacrylate, n-butyl methacrylate, isobutyl methacrylate, t-butyl methacrylate (Meth) acrylic esters such as, tridecyl methacrylate and benzyl methacrylate; styrene, α-methylstyrene, o-methylstyrene, m-methylstyrene, p-methylstyrene, pt
styrene-based monomers such as tert-butylstyrene;
Itaconic esters such as benzyl itaconate; maleic esters such as dimethyl maleate; fumaric esters such as dimethyl fumarate; acrylonitrile, methacrylonitrile, vinyl acetate;
-Hydroxyl-containing monomers such as hydroxyethyl, 2-hydroxyethyl methacrylate, hydroxypropyl acrylate, hydroxypropyl methacrylate; aminoethyl ethyl acrylate, aminopropyl acrylate, methacrylamide, aminoethyl methacrylate, aminopropyl methacrylate And amino group-containing monomers such as dimethylaminoethyl acrylate and dimethylaminoethyl methacrylate; and α-olefins such as ethylene.

Examples of the catalyst include peroxides such as t-butyl peroxybenzoate, di-t-butyl peroxide, cumene hydroxide, acetyl peroxide, benzoyl peroxide, lauroyl peroxide and the like; azobisisobutyl nitrile , Azobis-2,4-
Known polymerization initiators such as azo compounds such as dimethylvaleronitrile and azobiscyclohexanecarbonitrile can be used.

As the non-reactive solvent, for example, hexane,
Aliphatic hydrocarbon solvents such as mineral spirits; aromatic hydrocarbon solvents such as benzene, toluene and xylene; ester solvents such as butyl acetate; alcohol solvents such as methanol and butanol; methyl ethyl ketone and isobutyl methyl Ketone solvents such as ketones; dimethylformamide, dimethylsulfoxide, N
Aprotic polar solvents such as -methylpyrrolidone and pyridine; water; Further, these solvents may be used in combination.

As the reaction method, known general methods such as bulk polymerization, solution polymerization, suspension polymerization, emulsion polymerization, redox polymerization and the like can be mentioned. Among them, solution polymerization is preferred because the reaction method is simple.

The reaction conditions vary depending on the polymerization initiator and the solvent, but the reaction temperature is 180 ° C. or lower, preferably 3 ° C.
The reaction time is 0 to 150 ° C., and the reaction time is 30 minutes to 40 hours, preferably 2 hours to 30 hours.

The polyester-based polymer compound having an acidic group is not particularly limited in its production method. For example, a polyhydric alcohol and a polybasic acid, or an acid-alcohol compound such as 12-hydroxystearic acid may be used. ,
In a non-reactive solvent, dehydration esterification in the presence or absence of a catalyst, or those obtained by esterification of a compound having a glycidyl group and a polybasic acid, and the like, among which C8 or more And a polybasic acid or a polyhydric alcohol are essential components for the esterification reaction.

The method for preparing the polyester polymer having a basic group is not particularly limited. Examples thereof include a polyhydric alcohol and a polyhydric organic acid, a compound having a glycidyl group and an organic acid, or 12-hydroxystearic acid. After esterification by a known general method in the presence or absence of a non-reactive solvent and a catalyst with a combination of acid-alcoholic compounds such as above, amidation or esterification of amines or alcoholamines. And the like obtained by such a method.

Examples of the polyhydric alcohol include ethylene glycol, propylene glycol, neopentine glycol, dihydric alcohols such as decanediol and dodecanediol, trihydric alcohols such as trimethylolpropane, pentaerthritol and glycerin, Polymer diols such as polyester polyol, polyether polyol, polyamide diol, and polycaprolactone diol are exemplified.

Examples of polybasic acids include terephthalic acid,
Isophthalic acid, naphthalenedicarboxylic acid, diphenic acid,
Tribasic or higher such as dibasic acids such as sulfoterephthalic acid, succinic acid, adipic acid, azelaic acid, sebacic acid, decane diacid, dodecane diacid, dimer acid, trimellitic acid, trimesic acid, and pyromellitic acid And the like.

Examples of the compound having a glycidyl group include ethylene glycol diglycidyl ether, propylene glycol diglycidyl ether, glycerol polyglycidyl ether, sorbitol polyglycidyl ether, 1,6 hexanediol diglycidyl ether, glycerin polyglycidyl ether, and trimethylolpropane. Examples thereof include polyglycidyl ether, diglycidyl phthalate, and bisphenol A type epoxy resin.

As the acid-alcoholic compound, 12-
Hydroxystearic acid, P-hydroxyethoxybenzoic acid and the like.

Examples of the amines include ethylenediamine, diethylenetriamine, triethylenetetramine, metaphenylenediamine, pyridine, dimethylaminopropylamine, diethylaminopropylamine, and polyethyleneimine.

Examples of alcohol amines include monoethanolamine, diethanolamine, triethanolamine, dimethylaminoethanol, diethylaminoethanol, dimethylaminomethylphenol and the like.

As the non-reactive solvent, for example, hexane,
Aliphatic hydrocarbon solvents such as mineral spirits; aromatic hydrocarbon solvents such as benzene, toluene and xylene; ester solvents such as butyl acetate; alcohol solvents such as methanol and butanol; methyl ethyl ketone and isobutyl methyl Ketone solvents such as ketones; dimethylformamide, dimethylsulfoxide, N
Aprotic polar solvents such as -methylpyrrolidone, pyridine and the like; and these solvents may be used in combination. Among these solvents, in view of dehydration of the esterification reaction, aliphatic hydrocarbon solvents and aromatic hydrocarbon solvents are preferable.

The organic solvent which can be used in the dispersion composition of the present invention includes, for example, aliphatic hydrocarbon solvents such as hexane and mineral spirit; series corn oils such as dialkylpolysiloxane and cyclic polydialkylsiloxane. Vegetable oils such as olive oil, safflower oil, sunflower oil, soybean oil, linseed oil, etc .; aromatic hydrocarbon solvents such as benzene, toluene, xylene, etc .; ester solvents such as butyl acetate, etc .; Alcohol solvents; ketone solvents such as methyl ethyl ketone and isobutyl methyl ketone; aprotic polar solvents such as dimethylformamide, dimethyl sulfoxide, N-methylpyrrolidone, pyridine and the like; and these solvents may be used in combination. . Among these solvents, in consideration of charge generation, for example, hexane, mineral spirit, aliphatic hydrocarbons such as Isopar series manufactured by Exxon Chemical Co., and series cones such as dialkylpolysiloxane and cyclic polydialkylsiloxane Non-protic organic solvents such as oil, olive oil, safflower oil, sunflower oil, vegetable oils such as soybean oil and linseed oil, and more preferably a non-polar organic solvent having an electric resistivity of 10 ⁹ Ω · cm or more are more preferable.

The proportion of the above organic solvent is preferably in the range of 50 to 10,000 based on 100 parts by weight of the particulate material.
The range of 0 to 3000 parts by weight is more preferable. The dispersion composition of the present invention may contain, for example, surfactants, preservatives, deodorants, anti-peeling agents, fragrances, pigment dispersants, pigment derivatives, and the like other than those described above. The method for producing the dispersion composition of the present invention is not particularly limited, but is preferably produced by the following method.

(1) A dispersion step A in which a granular substance is dispersed in an organic solvent in which a polymer compound having an acidic group is dissolved by using a polymer compound having an acidic group, and the dispersion obtained in the dispersion step A is mixed with an acidic solution. A polymer having an acidic group and / or a polymer having a basic group are mixed with a dispersion in which a polymer having a basic group is dissolved or dispersed in an organic solvent in which the polymer having a group is not dissolved. Production of a dispersion composition comprising a mixing step B for adsorbing the compound to the particulate matter, a crosslinking step C for immobilizing the polymer compound by crosslinking if necessary, and a concentrating step D for distilling off the solvent if necessary. Method, (2) Dispersion step E of dispersing a particulate substance in an organic solvent dissolving a polymer compound having a basic group using a polymer compound having basicity, and a dispersion obtained in dispersion step E and a base Nature group A high molecular compound having an acidic group and / or a high molecular compound having a basic group is mixed with a dispersion obtained by dissolving or dispersing a high molecular compound having an acidic group in an organic solvent in which the high molecular compound does not dissolve. A method for producing a dispersion composition comprising a mixing step F for adsorbing to a substance, a crosslinking step G for immobilizing the polymer compound by crosslinking if necessary, and a concentrating step H for distilling off the solvent as necessary. Is mentioned. In the dispersing steps A and E, a polymer compound having an acidic group or a polymer compound having a basic group is dissolved in an organic solvent, and a particulate substance is added. Then, if necessary, glass beads, steel beads, zirconia beads, etc. Using a dispersing medium, a dispersion is obtained by a dispersing machine such as a bead mill such as a Dyno mill or a DSP-mill, a roll mill, a sand mill, an attritor, a high-pressure injection mill such as a kneader or a nanomizer, or the like. Further, if necessary, various additives such as a surfactant, a pigment dispersant, a pigment derivative, and a charge generating agent may be added.

The conditions for dispersion by the dispersing machine depend on the type of the granular material and the type of the dispersing machine.
In the temperature range of 0 ° C. to 150 ° C., the shorter the dispersion time, the better. However, the range of 0.1 to 10 hours / kg is preferable in terms of productivity. The particle size after dispersion is 1.0 to
The range of 0.01 μm is preferable, and 0.5 to 0.01 μm
Is more preferable, and the range of 0.3 to 0.01 μm is most preferable from the viewpoint of the sedimentation of the particulate matter.

The method of measuring the particle size is not particularly limited, but a known general method is used, for example, a particle size distribution measuring device of a laser scattering system or a centrifugal sedimentation system. Further, a crosslinking agent for crosslinking the polymer compound is mixed before or after dispersion. In particular, it is preferable to mix after dispersion since there is no influence of the reaction or the like during dispersion. The ratio of the crosslinking agent is not particularly limited as long as the polymer compound can be fixed to the particulate material by crosslinking, but is preferably in the range of 2 to 100 parts by weight, and more preferably 5 to 50 parts by weight, based on 100 parts by weight of the polymer compound. The range of parts is more preferable.

Next, in the mixing step B or F, a high molecular compound having a basic group or a high molecular compound having an acidic group is added, if necessary, to a simple stirrer such as a three-one motor, a magnetic stirrer, a disper, a homogenizer, or the like. Is used to dissolve or disperse in an organic solvent in which the polymer compound used in the dispersion step is not dissolved. This solution or the high molecular compound having a basic group or the high molecular compound having an acidic group is directly used in the dispersion prepared in the dispersion step A or E, or the dispersion obtained in the dispersion step A or E. The solution or the polymer compound having a basic group and the polymer compound having an acidic group are slowly added and mixed. In this case, at or after the addition, the dispersion is uniformly mixed using a simple stirrer such as a disper. The type and conditions of the stirrer are not particularly limited because they do not significantly affect the size, viscosity and surface charge density of the particles in the dispersion composition to be formed.

The organic solvent in which the high molecular compound does not dissolve is not particularly limited as long as the high molecular compound does not dissolve, but an organic solvent having a solubility parameter of 7.8 or less is particularly preferable. Examples of the organic solvent having a solubility parameter of 7.8 or less include aliphatic hydrocarbons such as hexane, mineral spirit, and Isopar series manufactured by Exxon Chemical Co., and silicone oils such as dialkylpolysiloxane and cyclic polydialkylsiloxane. Examples include oils, olive oil, safflower oil, sunflower oil, vegetable oils such as soybean oil and linseed oil, and diethyl ether.

In particular, the point of the solvent used here is that the polymer compound having a basic group or the polymer compound having an acidic group used in the dispersion steps A and E is insoluble in the organic solvent having the solubility parameter of 7.8 or less. That is. Therefore, by the addition steps B and F, a polymer compound having a basic group or a polymer compound having an acidic group can be precipitated and adsorbed on the surface of the granular material.

Another point is that a polymer compound having an acidic group or a polymer compound having a basic group which acts as a protective colloid is added. By adding these polymer compounds, the polymer compound used in the dispersing steps A and E and the polymer compound used in the adding steps B and F become counter ions, and large particles are produced as a protective colloid even in a poor solvent. And fine particles can be produced. The proportion of the organic solvent used here is preferably in the range of 0 to 10000 parts by weight with respect to 100 parts by weight of the polymer compound in order to increase the concentration of the particulate matter in the dispersion composition to be produced. In the crosslinking steps C and G in which the polymer compound is fixed by crosslinking, the crosslinking method is not particularly limited, and examples thereof include a crosslinking method using heating, ultraviolet rays, an electron beam, or the like. In particular, a method by heating is preferred because of the reactivity and the fact that the reaction can be carried out with a simple apparatus. The temperature of the crosslinking by heating is not particularly limited as long as the temperature does not destroy the dispersed state of the particulate matter, but is preferably 200 ° C. or lower, more preferably 180 ° C. or lower. The concentration step D or H is performed depending on the use of the particulate matter. Further, the concentration step may be performed before the crosslinking steps C and G.

As a method for concentrating the solvent, a general normal pressure or reduced pressure distillation method can be used. For example, when a dispersion composition is used in an aliphatic hydrocarbon solvent, a boiling point of an organic solvent in which a polymer compound is dissolved is lower than that of the aliphatic hydrocarbon solvent, and normal pressure or reduced pressure distillation is used. To concentrate. On the other hand, when the dispersion composition is used with an organic solvent that dissolves the polymer compound, the boiling point of the aliphatic hydrocarbon solvent is lower than that of the organic solvent that dissolves the polymer compound, and the pressure is reduced to normal pressure. Alternatively, it is concentrated by distillation under reduced pressure. Further, if necessary, all of them can be distilled or replaced with water and dried to be used for powder coatings, toners, plastics and the like.

The use of the dispersion composition is not particularly limited, but may be paints such as automobiles and constructions, PCM, printing inks such as gravure inks, inks for ink jet printers, ink jet printers using a wet electrophotographic printing machine or electrostatic force. Printer (for example, JP-A-8-29126)
No. 7, Patent No. 2735030, JHC'98FA
(Shown in high-density inkjet recording during LL Meeting, etc.). In particular, in the field of the liquid toner, there is no need to use a special charge generating agent, and the charge is stably fixed on the surface of the granular material, so that the long-term use stability is excellent. In order to use the dispersion composition of the present invention in these applications, a binder, an organic solvent, and various additives are added to each of the applications to adjust the concentration of the particulate material or the binder to a predetermined concentration. As the binder, for example, natural proteins, celluloses, polyvinyl alcohol, polyacrylamide, aromatic amide, polyacrylic acid, polyvinyl ether, polyvinylpyrrolidone, acrylic, polyester,
Known synthetic polymers such as alkyd, urethane, amide resin, melamine resin, ether resin, fluororesin, styrene acrylic resin, styrene maleic resin, etc., photosensitive resin, thermosetting resin, ultraviolet curable resin or electron beam curable resin However, the present invention is not particularly limited thereto. As the various additives, known general substances such as anionic, cationic and nonionic surfactants, anti-peeling agents, leveling agents, charge adjusting agents such as metal soaps and lecithin can be used. It is not limited to. The method of adding the binder, the organic solvent and various additives to the dispersion composition of the present invention to adjust the final paint, printing ink, and wet toner can be achieved by using a simple stirrer such as a disper. This eliminates the need for a dispersing machine, etc., which has been required, saves energy, and enables low-cost production.

[0058]

The present invention will be described below in detail with reference to Examples and Comparative Examples. In the following, “parts” and “%” use “parts by weight” and “% by weight” unless otherwise specified. In addition, as a reagent without precautionary notes, a reagent grade 1 manufactured by Wako Pure Chemical Industries, Ltd. was used.

<Synthesis Example 1> High-molecular compound having acidic group n-butyl acrylate 20.0 parts n-butyl methacrylate 5.0 parts lauryl methacrylate 40.0 parts styrene 15.0 parts methacrylic acid 20.0 parts perbutyl O (Peroxyester manufactured by Nippon Yushi Co., Ltd.) 8.0 parts was mixed to prepare a solution.

Next, 100 ml of methyl ethyl ketone (Wako Pure Chemical Industries, Ltd. reagent grade 1) was placed in a reaction vessel equipped with a nitrogen inlet tube.
Then, the temperature was raised to the boiling point while sealing with nitrogen. The solution was added dropwise over 2 hours, and after the completion of the addition, the mixture was reacted for 14 hours while refluxing. The solution after the reaction was a polymer compound having an acidic group having a nonvolatile content of 52.7%, an acid value of 130.6 KOH mg / g, and a number average molecular weight of 9,900. One part of this polymer compound was diluted with Isopar G. When 2.3 parts of Aiasoper G was added, it became cloudy.
It did not dissolve in Isopar G.

<Synthesis Example 2> Polymer compound having an acidic group n-butyl methacrylate 15.3 parts Lauryl methacrylate 50.0 parts Styrene 15.0 parts Methacrylic acid 10.8 parts Glycidyl methacrylate 12.0 parts Perhexyl O (Japan A solution was prepared by mixing 8.0 parts of a dialkyl peroxide (manufactured by Yushi Co., Ltd.). Next, 100 parts of methyl ethyl ketone was weighed into a reaction vessel equipped with a nitrogen inlet tube, and the temperature was raised to the boiling point while sealing with nitrogen. The solution was added dropwise over 2 hours, and after the completion of the addition, the mixture was reacted for 6 hours while refluxing. The solution after the reaction had a nonvolatile content of 51.3.
%, Acid value 50.2 KOHmg / g, number average molecular weight 860
It was a polymer compound having 0 reactive group and acidic group.
One part of this polymer compound was diluted with Isopar G. When 7.7 parts of Iasoper G was added, it became cloudy and did not dissolve in Isopar G.

<Synthesis Example 3> High-molecular compound having an acidic group n-butyl methacrylate 18.4 parts Lauryl methacrylate 50.0 parts Styrene 15.0 parts Methacrylic acid 4.6 parts Glycidyl methacrylate 12.0 parts Perbutyl O (Japan A solution was prepared by mixing 8.0 parts of a peroxyester manufactured by Yushi Corporation. Next, 100 parts of methyl ethyl ketone was weighed into a reaction vessel equipped with a nitrogen inlet tube, and the temperature was raised to the boiling point while sealing with nitrogen. The solution was added dropwise over 2 hours, and after the completion of the addition, the mixture was reacted for 6 hours while refluxing. The solution after the reaction had a nonvolatile content of 52.3.
%, Acid value 29.7 KOHmg / g, number average molecular weight 140
It was a high molecular compound having a reactive group of 00 and an acidic group. One part of this polymer compound was diluted with Isopar G.
When 15 parts of Aiasoper G was added, it became cloudy and did not dissolve in Isopar G.

<Synthesis Example 4> Polymer Compound Having Acid Group n-butyl methacrylate 21.4 parts Lauryl methacrylate 20.0 parts Styrene 45.0 parts Methacrylic acid 1.6 parts Glycidyl methacrylate 12.0 parts Perbutyl O (Japan A solution was prepared by mixing 8.0 parts of a peroxyester manufactured by Yushi Corporation. Next, 100 parts of methyl ethyl ketone was weighed into a reaction vessel equipped with a nitrogen inlet tube, and the temperature was raised to the boiling point while sealing with nitrogen. The solution was added dropwise over 2 hours, and after the completion of the addition, the mixture was reacted for 6 hours while refluxing. The solution after the reaction had a nonvolatile content of 50.3.
%, Acid value 10.2 KOHmg / g, number average molecular weight 800
It was a polymer compound having 0 reactive group and acidic group.
One part of this polymer compound was diluted with Isopar G. When 3.8 parts of Aiasoper G was added, it became cloudy and did not dissolve in Isopar G.

<Synthesis Example 5> Polymer compound having an acidic group n-butyl methacrylate 10.7 parts Lauryl methacrylate 50.0 parts 2-ethylhexyl acrylate 30.0 parts Methacrylic acid 9.3 parts Perbutyl O (manufactured by NOF Corporation) A peroxyester) of 8.0 parts was mixed to prepare a solution. Next, 100 parts of Isopar G (aliphatic hydrocarbon solvent manufactured by Exxon Chemical Co., Ltd.) was weighed into a reaction vessel equipped with a nitrogen inlet tube, and the temperature was raised to 105 ° C. while sealing with nitrogen. The solution was added dropwise over 2 hours, and after the completion of the addition, the mixture was reacted for 14 hours while maintaining a temperature of 105 ° C. The solution after the reaction has a nonvolatile content of 5
It was a polymer compound having an acidic group having an acid value of 0.5%, an acid value of 60.2 KOH mg / g, and a number average molecular weight of 6,300.

<Synthesis example 6> Polymer compound having basic group Ethyl methacrylate 10.0 parts n-butyl methacrylate 32.0 parts Lauryl methacrylate 50.0 parts Dimethylaminoethyl methacrylate 8.0 parts Azobisisobutylnitrile 1. A solution was prepared by mixing 0 parts. Next, 100 parts of Isopar G was weighed into a reaction vessel equipped with a nitrogen inlet tube, and the temperature was raised to 90 ° C. while sealing with nitrogen. The above solution, 2
The mixture was dropped over a period of time, and the reaction was continued for 14 hours while maintaining the temperature of 90 ° C. at the end of the dropping. The solution after the reaction was a polymer compound having a non-volatile content of 48.1%, an amine value of 28.3 KOH mg / g, and a basic group having a number average molecular weight of 23,000.

<Synthesis Example 7> Polymer Compound Having Basic Group n-butyl acrylate 10.0 parts n-butyl methacrylate 10.0 parts lauryl methacrylate 20.0 parts styrene 30.0 parts dimethylaminoethyl methacrylate 30.0 A solution was prepared by mixing 2.0 parts of perhexyl O (peroxyester manufactured by NOF Corporation). Next, 100 parts of methyl ethyl ketone was weighed into a reaction vessel equipped with a nitrogen inlet tube, and the temperature was raised to the boiling point while sealing with nitrogen. The solution was added dropwise over 2 hours, and after the completion of the addition, the mixture was reacted for 14 hours while refluxing. The solution after the reaction had a non-volatile content of 51.
The polymer was a high molecular compound having a basic group of 2%, an amine value of 106.4 KOH mg / g, and a number average molecular weight of 13,300. One part of this polymer compound was diluted with Isopar G.
When 10 parts of Aiasoper G was added, it became cloudy and did not dissolve in Isopar G.

<Synthesis Example 8> High-molecular compound having acidic group n-butyl methacrylate 26.7 parts Lauryl methacrylate 50.0 parts Styrene 5.0 parts Methacrylic acid 10.8 parts β-hydroxyethyl methacrylate 7.5 parts Perhexyl A solution was prepared by mixing 8.0 parts of O. Next, 100 parts of methyl ethyl ketone was weighed into a reaction vessel equipped with a nitrogen inlet tube, and the temperature was raised to the boiling point while sealing with nitrogen. The solution was added dropwise over 2 hours, and after the completion of the addition, the mixture was reacted for 14 hours while refluxing. The solution after the reaction had a nonvolatile content of 50.
8%, acid value 69.5 KOHmg / g, number average molecular weight 76
00 was a polymer compound having a hydroxyl group and an acidic group as reactive groups. One part of this polymer compound was diluted with Isopar G. When 6.5 parts of Iasoper G was added, it became cloudy and did not dissolve in Isopar G.

Table 1 summarizes the structures and characteristics of Synthesis Examples 1 to 8.

[0069]

[Table 1]

Example 1 As an acrylic polymer compound having an acidic group in a 100 cc plastic bottle Synthesis Example 1 7.6 parts Cyanine blue 4973 as a particulate material (copper phthalocyanine blue pigment manufactured by Dainichi Seika) 4 2.0 parts Methyl ethyl ketone 2.4 parts Isopar G 6.0 parts 3 mmφ zirconia beads 100 parts are weighed and dispersed with a paint shaker (manufactured by Aishin) for 2 hours, and methyl ethyl ketone 16.0 parts Isopar G 24.0 parts are added. To obtain a dispersion slurry.

Next, 3.75 parts of Solsperse 13940 (manufactured by Zeneca) as a polyester polymer compound having a basic group is measured in a beaker and stirred with a magnetic stirrer. Under stirring, 15.0 parts of the above-mentioned dispersion slurry was slowly added dropwise to precipitate a polymer compound having an acidic group on the surface of the granular material.

After the dropwise addition, the solvent was removed from the methyl ethyl ketone by distillation under reduced pressure to obtain a dispersion composition having a pigment concentration of 4.1%.
The obtained dispersion composition had a dispersed particle diameter of 132 nm (a laser Doppler type particle size distribution meter N manufactured by Coulter, Inc.).
4 PLUS), and 33
A centrifugal force of 500 G was applied for 5 hours to measure the amount of resin adsorbed by centrifugal sedimentation from the non-volatile content of the supernatant.
The adsorption amount of 78 parts was shown with respect to 00 parts.

Further, 73.2 parts of the above dispersion composition and 26.8 parts of Isopar G were mixed to prepare an oil-based inkjet ink having a pigment content of 3%. The zeta potential of this ink-jet ink is -27 mV (LA from Penchem).
(Measured by ZER ZEE METER Model 501), and the particle diameter was 133 nm. Furthermore, when this ink-jet ink was subjected to a storage test in a thermostat at 60 ° C. for 14 days, the dispersion particle diameter was 130 nm, no aggregation occurred, and the ζ potential did not change to −26 mV. showed that.

Comparative Example 1 A pigment concentration of 4.75 was obtained in the same manner as in Example 1 except that 3.75 parts of Isopar G was used in place of Solsperse 13940, a polymer compound having a basic group, used in Example 1. A 2% dispersion composition was obtained.
The resulting dispersion composition had a dispersed particle diameter of 3169 nm.
(Measured with a laser Doppler type particle size distribution meter N4 PLUS manufactured by Coulter Co., Ltd.), and settled out after several hours, and the stability was higher than that of Example 1.

Example 2 In place of Solsperse 13940, a polymer having a basic group used in Example 1, 3.1 parts of a polymer having a basic group of Synthesis Example 6 and 0.65 of Isopar G were used. A dispersion composition having a pigment concentration of 4.3% was obtained in the same manner as in Example 1 except that parts were used. The obtained dispersion composition had a dispersed particle diameter of 141 nm (a laser Doppler type particle size distribution meter N4 manufactured by Coulter, Inc.).
PLUS) and 335
A centrifugal force of 00 G was applied for 5 hours to measure the amount of resin adsorbed by centrifugal sedimentation from the non-volatile content of the supernatant.
An adsorption amount of 82 parts was shown with respect to 0 parts. 69.7 parts of the above dispersion composition and 30.3 parts of Isopar G were mixed,
An oil-based inkjet ink having a pigment content of 3% was prepared.
The zeta potential of this inkjet ink was 14 mV (LAZER ZEE METERMode manufactured by Penchem).
The particle size was 140 nm.
Further, when this ink-jet ink was subjected to a storage test in a thermostat at 60 ° C. for 14 days, the dispersion particle diameter was 142 n.
No aggregation occurred, and the ζ potential did not change to 15 mV, indicating extremely excellent storage stability.

Example 3 As an acrylic polymer compound having an acidic group in a 100 cc plastic bottle, Synthesis Example 2 7.8 parts As a particulate material, Fastgen Blue TGR (Copper manufactured by Dainippon Ink and Chemicals, Inc.) 3.8 parts Copper phthalocyanine pigment derivative Solsperse 5000 0.2 parts Isopar G 8.2 parts 3 mmφ zirconia beads 100 parts Weigh and measure with a paint shaker (manufactured by AISIN Co., Ltd.) for 2 hours, and methyl ethyl ketone 6.0. In addition, 24.0 parts of Isopar G was added and mixed to obtain a dispersion slurry.

As a polyester polymer compound having a basic group, Solsperse 13940 5.0 parts Isopar G 45.0 parts is measured in a beaker and stirred with a magnetic stirrer. Under stirring, 50.0 parts of the dispersion slurry was slowly dropped, and a polymer having an acidic group was precipitated on the surface of the granular material. After the dropwise addition, methyl ethyl ketone and Isopar G were distilled under reduced pressure, and the dispersion composition was concentrated. In addition, 1
A cross-linking reaction between the glycidyl group of the reactive group and the carboxyl group of the acidic group was performed at a temperature of 20 ° C. for 5 hours under normal pressure. Before and after the reaction, the acid value decreased by 14.5 KOH mg / g, and crosslinking of the polymer compound was confirmed. The resulting dispersion composition had a pigment concentration of 4.62% and a dispersed particle size of 171 nm.
(Measured with a laser Doppler type particle size distribution meter N4 PLUS manufactured by Coulter Co., Ltd.) Further, the dispersion composition was subjected to a centrifugal force of 33,500 G for 5 hours to measure the amount of resin adsorbed by centrifugal sedimentation from the non-volatile content of the supernatant. The amount of adsorption was 58 parts per 100 parts of the substance.

By mixing 64.9 parts of the above dispersion composition and 35.1 parts of Isopar G, an oil-based inkjet ink having a pigment content of 3% was prepared. The zeta potential of this ink-jet ink is 22.4 mV (Laz manufactured by Penchem)
(Measured with ER ZEE METER Model 501)
And the particle diameter was 170 nm. Further, when the inkjet ink was subjected to a storage test for 14 days in a thermostat at 60 ° C., the dispersion particle diameter was 168 nm, no aggregation occurred, and the ζ potential did not change to 21.6 mV. Showed sex.

Comparative Example 2 A pigment concentration of 4. was obtained in the same manner as in Example 1 except that 5.0 parts of Isopar G was used instead of Solsperse 13940, a polymer compound having a basic group, used in Example 3. A 3% dispersion composition was obtained. The obtained dispersion composition has a dispersed particle diameter of 2563 nm (a laser Doppler type particle size distribution meter N manufactured by Coulter, Inc.).
4 PLUS), and settled out after several hours, and the stability was higher than that of Example 3.

Example 4 As an acrylic polymer compound having an acidic group in a 100 cc plastic bottle, Synthesis Example 2 7.8 parts As a particulate material, Fastgen Super Magenta RG (manufactured by Dainippon Ink and Chemicals, Inc.) 4.0 parts Isopar G 8.2 parts 3 mmφ zirconia beads 100 parts Weigh and dispense with a paint shaker (manufactured by Aishin) for 2 hours, add methyl ethyl ketone 6.0 parts Isopar G 24.0 parts. To obtain a dispersion slurry.

As a polyester polymer compound having a basic group, Solsperse 13940 5.0 parts Isopar G 45.0 parts is measured in a beaker and stirred with a magnetic stirrer. Under stirring, 50.0 parts of the dispersion slurry was slowly dropped, and a polymer having an acidic group was precipitated on the surface of the granular material. After the dropwise addition, methyl ethyl ketone and Isopar G were distilled under reduced pressure, and the dispersion composition was concentrated. In addition, 1
A cross-linking reaction between the glycidyl group of the reactive group and the carboxyl group of the acidic group was performed at a temperature of 20 ° C. for 5 hours under normal pressure. Before and after the reaction, the acid value decreased by 14.2 KOH mg / g, and crosslinking of the polymer compound was confirmed. The resulting dispersion composition had a pigment concentration of 4.59% and a dispersed particle size of 198 nm.
(Measured with a laser Doppler type particle size distribution meter N4 PLUS manufactured by Coulter Co., Ltd.) Further, the dispersion composition was subjected to a centrifugal force of 33,500 G for 5 hours to measure the amount of resin adsorbed by centrifugal sedimentation from the non-volatile content of the supernatant. The adsorption amount was 56 parts per 100 parts of the substance.

65.4 parts of the above dispersion composition, 28.7 parts of Isopar G, and 5.9 parts of the acrylic resin of Synthesis Example 5 as a charge generating agent were mixed to prepare an oil-based inkjet ink having a pigment content of 3%. . The zeta potential of this inkjet ink is 66 mV (LAZER Z manufactured by Penchem).
EE METER Model 501) and the particle size was 193 nm. Furthermore, when this ink-jet ink was subjected to a storage test for 14 days in a thermostat at 60 ° C., the dispersion particle diameter was 195 nm, no aggregation occurred, and the ζ potential did not change to 62 mV. It showed charge stability.

Comparative Example 2 3.75 parts of Solsperse 13940 as a polyester polymer compound having a basic group in a 100 cc plastic bottle As a granular material, Fastgen Super Magenta RG (dimethyl manufactured by Dainippon Ink and Chemicals, Inc.) Quinacridone pigment) 4.0 parts Isopar G 12.25 parts 3 mmφ zirconia beads 100 parts Weigh and measure with paint shaker (manufactured by Aishin).
After time dispersion, 20.0 parts of Isopar G was added to obtain a dispersion composition. The resulting dispersion composition has a pigment concentration of 10.
At 0%, the dispersion particle diameter is 195 nm (measured with a laser Doppler type particle size distribution analyzer N4 PLUS manufactured by Coulter Co., Ltd.). Further, the dispersion composition is subjected to a centrifugal force of 33,500 G for 5 hours by centrifugal sedimentation from the supernatant nonvolatile matter. When the resin adsorption amount was measured, the amount
It showed an adsorption amount of 3 parts and was a normal pigment dispersion to which the resin was adsorbed. 30.0 parts of the above dispersion composition, Isopar G
64.1 parts and 5.9 parts of the acidic acrylic resin of Synthesis Example 5 as a neutralizing agent were mixed to prepare an oil-based inkjet ink having a pigment content of 3%. The zeta potential of this ink is 78 mV
(LAZER ZEE METER M manufactured by Penchem
odel 501), and the particle size was 197 m. Further, when this inkjet ink was subjected to a storage test in a thermostat at 60 ° C. for 7 days, the dispersed particle diameter was 225.
nm, sedimentation occurs, and the ζ potential is 23
mV, which was inferior to Example 4 in storage stability and charge stability.

Example 4 As an acrylic polymer compound having an acidic group in a 100 cc plastic bottle, Synthesis Example 3 7.6 parts As a particulate material, Fastgen Super Magenta RG (manufactured by Dainippon Ink and Chemicals, Inc.) (Dimethyl quinacridone pigment) 4.0 parts Methyl ethyl ketone 8.4 parts 3 mmφ 100 parts of zirconia beads were weighed out, dispersed for 2 hours with a paint shaker (manufactured by Aisin Co.), and mixed with 46.7 parts of methyl ethyl ketone to obtain a dispersion slurry. .

As a polyester polymer having a basic group, 3.75 parts of Solsperse 13940 parts and 32.9 parts of Isopar G are weighed into a beaker and stirred with a magnetic stirrer. Under stirring, 25.0 parts of the dispersion slurry was slowly dropped, and a polymer compound having an acidic group was precipitated on the surface of the granular material. After the dropwise addition, the solvent was removed from the methyl ethyl ketone by distillation under reduced pressure, and a cross-linking reaction between a glycidyl group as a reactive group, a carboxyl group as an acidic group, and a carboxyl group as an acidic group was performed under a normal pressure at a temperature of 120 ° C. for 5 hours. Before and after the reaction, the acid value was 10.1
KOH mg / g was reduced, and cross-linking of the polymer compound was confirmed. The resulting dispersion composition had a pigment concentration of 3.84%.
The dispersion particle size is 225 nm (measured with a Coulter laser Doppler type particle size distribution meter N4 PLUS), and the centrifugal force of 33500 G is applied to the dispersion composition for 5 hours to determine the amount of resin adsorbed by centrifugal sedimentation from the non-volatile content of the supernatant. As a result of measurement, the amount of adsorption was 66 parts with respect to 100 parts of the particulate matter. 78.1 parts of the above dispersion composition, Synthesis Example 5
Was mixed with 5.9 parts of Isopar G to prepare a wet toner having a pigment content of 3%. The zeta potential of this wet toner is 40 mV (LAZER ZE manufactured by Penchem).
E METER Model 501), and the particle size was 223 nm. Furthermore, when the inkjet ink was subjected to a storage test for 7 days in a thermostat at 60 ° C., the dispersion particle diameter was 223 nm, no aggregation occurred, and
The ζ potential did not change to 42 mV, indicating very excellent storage stability.

Comparative Example 3 3.75 parts of Solsperse 13940 as a polyester-based polymer compound having a basic group in a 100 cc plastic bottle As a particulate material, Fastgen Super Magenta RG (dimethyl manufactured by Dainippon Ink and Chemicals, Inc.) Quinacridone pigment) 4.0 parts Isopar G 12.25 parts 3 mmφ zirconia beads 100 parts Weigh and measure with paint shaker (manufactured by Aishin).
After time dispersion, 20.0 parts of Isopar G was added to obtain a dispersion composition. The resulting dispersion composition has a pigment concentration of 10.
At 1%, the dispersed particle diameter is 197 nm (measured with a Coulter laser Doppler type particle size distribution analyzer N4 PLUS), and the dispersion composition is subjected to a centrifugal force of 33,500 G for 5 hours by centrifugal sedimentation from the supernatant nonvolatile matter. When the resin adsorption amount was measured, the amount
It showed an adsorption amount of 3 parts and was a normal pigment dispersion to which the resin was adsorbed. 29.7 parts of the above dispersion composition and 70.3 parts of Isopar G were mixed to prepare a wet toner having a pigment content of 3%. The zeta potential of this wet toner is 12 mV (LAZER ZEE METER Mode manufactured by Penchem).
The particle size was 198 nm.
Further, when this ink-jet ink was subjected to a storage test for 7 days in a thermostat at 60 ° C., the dispersion particle diameter was 210 nm.
, The sedimentation occurred, and the ζ potential also dropped to 4 mV, which was inferior to the storage stability in Example 4.

Example 5 3.8 parts of # 4000 (Carbon Black manufactured by Mitsubishi Chemical Corporation) and 0.2 parts of Solsperse 5000 are used instead of the granular material Fastgen Super Magenta RG used in Example 4. Except having used, it carried out similarly to Example 4, and obtained the dispersion liquid composition. Before and after the crosslinking reaction, the acid value decreased by 9.9 KOH mg / g, and crosslinking of the polymer compound was confirmed. The resulting dispersion composition had a pigment concentration of 3.92% and a dispersed particle size of 196 nm.
(Measured with a laser Doppler type particle size distribution meter N4PLUS manufactured by Coulter Co., Ltd.).
A centrifugal force of 3500 G was applied for 5 hours to measure the amount of resin adsorbed by centrifugal sedimentation from the nonvolatile matter in the supernatant. As a result, the adsorbed amount was 62 parts per 100 parts of the particulate matter. 76.5 parts of the dispersion composition, 5.9 parts of Synthesis Example 5, and 17.6 parts of Isopar G were mixed to prepare a wet toner having a pigment content of 3%. The zeta potential of this wet toner is 35 mV (LAZER ZEE METER Mode manufactured by Penchem).
The particle size was 205 nm.
Further, when this ink-jet ink was subjected to a storage test for 14 days in a thermostat at 60 ° C., the dispersed particle diameter was 203 n.
No aggregation occurred, and the ζ potential did not change to 34 mV, indicating extremely excellent storage stability.

{Comparative Example 4} # 4000 (Mitsubishi Chemical Corporation carbon black) instead of Fasten Super Magenta RG which is the granular substance used in Comparative Example 3
A dispersion composition was obtained in the same manner as in Comparative Example 3 except that 3.8 parts and Solsperse 5000 / 0.2 part were used. The obtained dispersion composition had a pigment concentration of 10.3%, a dispersion particle diameter of 198 nm (measured by a laser Doppler type particle size distribution meter N4 PLUS manufactured by Coulter, Inc.). The amount of resin adsorbed by centrifugal sedimentation was measured from the non-volatile content of the supernatant by applying a centrifugal force for 5 hours. As a result, the adsorbed amount of the resin was 8 parts per 100 parts of the granular substance, and it was a normal pigment dispersion. The above dispersion composition 2
By mixing 9.1 parts and 70.9 parts of Isopar G, a wet toner having a pigment content of 3% was prepared. The zeta potential of this wet toner is 6 mV (LAZER ZEE manufactured by Penchem).
METER Model 501) and the particle size was 202 nm. Furthermore, when this inkjet ink was subjected to a storage test for 14 days in a constant temperature bath at 60 ° C.,
The dispersed particle diameter increases to 230 nm, sedimentation occurs,
Also, the も potential was lowered to −28 mV, and the storage stability was inferior to that of Example 5.

Example 6 As an acrylic polymer compound having an acidic group in a 100 cc plastic bottle, Synthesis Example 4 8.0 parts As a particulate material, Fastgen Blue TGR (Copper manufactured by Dainippon Ink and Chemicals, Inc.) 3.8 parts Copper phthalocyanine pigment derivative Solsperse 5000 5000 parts Isopar G 8.0 parts 3 mmφ zirconia beads 100 parts Weigh and measure with a paint shaker (manufactured by Aisin Co., Ltd.) for 2 hours, and dissolve methyl ethyl ketone 9.3 37.3 parts of Isopar G were added and mixed to obtain a dispersion slurry.

As a polyester polymer compound having a basic group, 3.75 parts of Solsperse 13940 parts, 21.25 parts of Isopar G, 3.3 parts of methyl ethyl ketone are measured in a beaker and stirred with a magnetic stirrer. Under stirring, 25.0 parts of the dispersion slurry was slowly dropped, and a polymer compound having an acidic group was precipitated on the surface of the granular material. After the dropwise addition, the solvent was removed from the methyl ethyl ketone by distillation under reduced pressure, and a cross-linking reaction between a glycidyl group as a reactive group, a carboxyl group as an acidic group, and a carboxyl group as an acidic group was performed under a normal pressure at a temperature of 120 ° C. for 5 hours. Before and after the reaction, the acid value is 6.1K
OH mg / g was reduced, and crosslinking of the polymer compound was confirmed. The resulting dispersion composition had a pigment concentration of 3.3%, a dispersed particle diameter of 227 nm (measured with a Coulter Co., Ltd. laser Doppler type particle size distribution analyzer N4 PLUS). The amount of resin adsorbed by centrifugal sedimentation was measured from the nonvolatile content of the supernatant by applying a centrifugal force for 5 hours. 90.9 parts of the above dispersion composition, Synthesis Example 5
Was mixed with 5.9 parts of Isopar G to prepare a wet toner having a pigment content of 3%. The zeta potential of this wet toner is 52 mV (LAZER ZEE manufactured by Penchem).
METER Model 501) and the particle size was 225 nm. Further, when the inkjet ink was subjected to a storage test in a thermostat at 60 ° C. for 14 days, the dispersion particle diameter was 228 nm, no aggregation occurred, and
The ζ potential did not change to 55 mV, indicating very excellent storage stability.

Comparative Example 5 Instead of the granular material Fastgen Super Magenta RG used in Comparative Example 3, Fasten Blue T
A dispersion composition was obtained in the same manner as in Comparative Example 3 except that 3.8 parts of GR and 0.2 parts of Solsperse 5000 were used. The resulting dispersion composition had a pigment concentration of 10.2%,
The dispersion particle diameter is 152 nm (measured with a Coulter laser Doppler type particle size distribution meter N4 PLUS). The dispersion adsorbed on the dispersion composition by centrifugal force of 33500 G for 5 hours from the non-volatile content of the supernatant by centrifugal sedimentation. As a result of measurement, the amount of adsorption was found to be 15 parts with respect to 100 parts of the particulate material, and it was a normal pigment dispersion. 29.4 parts of the above dispersion composition and 70.6 parts of Isopar G were mixed to prepare a wet toner having a pigment content of 3%. The zeta potential of this wet toner is 13 mV (LAZER manufactured by Penchem).
(Measured with ZEE METER Model 501)
And the particle diameter was 163 nm. Further, when the inkjet ink was subjected to a storage test for 14 days in a constant temperature bath at 60 ° C., the dispersed particle diameter was slightly increased to 170 nm and no sedimentation was observed, but the Δ potential was reduced to 5 mV,
The storage stability was inferior to that of Example 6.

Example 7 As an acrylic polymer compound having a basic group in a 100 cc plastic bottle, Synthesis Example 7 7.8 parts As a particulate material, Fastgen Super Magenta RG (manufactured by Dainippon Ink and Chemicals, Inc.) 4.0 parts Methyl ethyl ketone 8.2 parts 3 mmφ zirconia beads 100 parts were weighed out, dispersed with a paint shaker (manufactured by Aishin) for 2 hours, and methyl ethyl ketone 30.0 parts Isopar G 30.0 parts were added. Further, the mixture was dispersed with a paint shaker for 10 minutes to obtain a dispersion slurry. As an acrylic polymer compound having an acidic group, Synthesis Example 5 4.0 parts Isopar G 36.0 parts was weighed into a beaker and stirred with a magnetic stirrer. Under stirring, 10.0 parts of the above dispersion slurry was slowly added dropwise to precipitate a polymer compound having a basic group on the surface of the granular material. After the dropwise addition, the solvent was removed from the methyl ethyl ketone and Isopar G by distillation under reduced pressure to obtain a dispersion composition. The obtained dispersion composition had a pigment concentration of 3.73%, a dispersed particle diameter of 214 nm (measured with a laser Doppler type particle size distribution meter N4 PLUS manufactured by Coulter, Inc.). A centrifugal force was applied for 5 hours to measure the amount of resin adsorbed by centrifugal sedimentation from the non-volatile content of the supernatant. 80.4 parts of the above dispersion composition and Isopar G
20.6 parts were mixed to prepare a wet toner having a pigment content of 3%. The zeta potential of this wet toner is 37 mV (LAZERZE METER Model, manufactured by Penchem).
501 (measured at 501), and the particle size was 215 nm. Further, the inkjet ink was placed in a thermostat at 60 ° C. for 14 hours.
After a storage test for a day, the dispersion particle diameter was 213 nm, no aggregation occurred, and the ζ potential did not change to 35 mV.
It showed very good storage stability.

Example 8 As an acrylic polymer compound having an acidic group in a 100 cc plastic bottle, 8.2 parts of Synthesis Example 8 As a particulate material, Fastgen Super Magenta RG (manufactured by Dainippon Ink and Chemicals, Inc.) 4.0 parts Methyl ethyl ketone 7.8 parts 3 mmφ zirconia beads 100 parts Weigh and measure with a paint shaker (manufactured by AISIN Co., Ltd.) for 2 hours. Superbecamine L-117-60 (Dainippon Ink & Chemicals, Inc.) (Melamine resin manufactured) 1.4 parts Methyl ethyl ketone 30.0 parts Isopar G 30.0 parts were added, and further dispersed with a paint shaker for 10 minutes to obtain a dispersed slurry. As a polyester polymer having a basic group, 5.0 parts of Solsperse 13940 parts and 35.0 parts of Isopar G are weighed into a beaker and stirred with a magnetic stirrer. Under stirring, 40.0 parts of the dispersion slurry was slowly added dropwise to precipitate a polymer compound having an acidic group on the surface of the granular material. After dropping, add methyl ethyl ketone and Isopar G
Was removed by distillation under reduced pressure.
A cross-linking reaction between a melamine resin and a hydroxyl group as a reactive group in a polymer compound having an acidic group under normal pressure for a time,
A dispersion composition was obtained. The resulting dispersion composition had a pigment concentration of 4.23% and a dispersed particle size of 248 nm (a laser Doppler type particle size distribution meter N4PL manufactured by Coulter, Inc.).
US) and 33500 G
The amount of resin adsorbed by centrifugal sedimentation was measured from the nonvolatile content of the supernatant by centrifugal force for 5 hours. Dispersion composition 7
0.9 parts and 29.1 parts of Isopar G were mixed to prepare a wet toner having a pigment content of 3%. The zeta potential of this wet toner is 29 mV (LAZER ZEE manufactured by Penchem).
METER Model 501) and the particle size was 249 nm. Furthermore, when this ink-jet ink was subjected to a storage test in a thermostat at 60 ° C. for 14 days, the dispersion particle diameter was 245 ”nm, no aggregation occurred, and the ζ potential did not change to 29 mV. Showed sex.

Example 9 The dispersion composition prepared in Example 6 was diluted with isopropyl alcohol, and its application to a polar solvent was confirmed. As a result, the dispersed particle diameter was 225 N
It was a dispersion composition that did not aggregate with M and could be applied to, for example, printing inks and paints using isopropyl alcohol.

Comparative Example 6 The dispersion composition prepared in Comparative Example 5 was diluted with isopropyl alcohol, and its application to a polar solvent was confirmed. As a result, the dispersed particle diameter was 1567.
It aggregated with NM and could not be expected to be applied to, for example, printing inks or paints using isopropyl alcohol.

Example 10 As an acrylic polymer compound having an acidic group in a 100 cc plastic bottle, Synthesis Example 9 12.0 parts As a particulate material, Cinqualia Magnetna RT-355-D (manufactured by Ciba Specialty Chemicals Co., Ltd.) 6.0 parts Methyl ethyl ketone 12.0 parts 3 mmφ zirconia beads 100 parts Weigh and dispense with a paint shaker (manufactured by Aishin) for 2 hours. 13.5 parts of methyl ethyl ketone 16.5 parts of Isopar G

As a polyester polymer compound having a basic group, Solsperse 13940 11.25 parts Isopar G 63.75 parts Methyl ethyl ketone 5.0 parts are measured in a beaker and stirred with a magnetic stirrer. Under stirring, a mixture of 45 parts of the dispersion slurry, 13.5 parts of methyl ethyl ketone, and 16.5 parts of Isopar G was slowly added dropwise to precipitate a polymer compound having an acidic group on the surface of the granular material. After the dropwise addition, the solvent was removed from the methyl ethyl ketone by distillation under reduced pressure, and a cross-linking reaction between a glycidyl group as a reactive group, a carboxyl group as an acidic group, and a carboxyl group as an acidic group was performed at 130 ° C. for 5 hours under normal pressure. Before and after the reaction, the acid value decreased by 5.4 KOH mg / g, and crosslinking of the polymer compound was confirmed. The resulting dispersion composition had a pigment concentration of 4.16% and a dispersed particle size of 192 nm (a laser Doppler type particle size distribution meter N4PL manufactured by Coulter, Inc.).
US) and 33500 G
The centrifugal force was applied for 5 hours, and the amount of resin adsorbed by centrifugal sedimentation was measured from the non-volatile content of the supernatant. Dispersion composition 7
2.1 parts, 5.9 parts of Synthesis Example 5 and Isopar G22.
0 parts were mixed to prepare an oil-based inkjet ink having a pigment content of 3%. The zeta potential of this ink is 43 mV
(LAZER ZEE METERMo manufactured by Penchem)
(measured by del 501), the particle diameter was 198 nm, and the viscosity was 2.4 mPa · s. In addition, 60
When a storage test was performed for 7 days in a constant temperature bath at ℃, the dispersion particle diameter was 196 nm, no aggregation occurred, and the viscosity was 2.4 m.
The change in Pa · s and ζ potential was as small as 41 mV, indicating very excellent storage stability.

Comparative Example 7 3.75 parts of Solsperse 13940 as a polyester-based polymer compound having a basic group in a 100 cc plastic bottle As a granular substance, Cinquasia Magnetna RT-355-D (manufactured by Ciba Specialty Chemicals) Quinacridone pigment) 4.0 parts Isopar G 12.25 parts 3 mmφ zirconia beads 100 parts Weigh and measure with paint shaker (manufactured by Aishin).
After time dispersion, 20.0 parts of Isopar G was added to obtain a dispersion composition. The resulting dispersion composition has a pigment concentration of 10.
At 0%, the dispersion particle diameter is 198 nm (measured with a Coulter laser Doppler type particle size distribution analyzer N4 PLUS), and the dispersion composition is subjected to a centrifugal force of 33,500 G for 5 hours by centrifugal sedimentation from the supernatant nonvolatile matter. When the resin adsorption amount was measured, the amount
The amount of adsorption was 1 part, and it was a normal pigment dispersion in which the resin was adsorbed. 30.0 parts of the above dispersion composition, 5.9 parts of Synthesis Example 5, 0.8 parts of acetic acid and 63.3 parts of Isopar G as a neutralizing agent were mixed, and an oil-based inkjet having a pigment content of 3% was mixed. The ink was adjusted. The zeta potential of this ink is -2.5 mV (LAZER ZEEM manufactured by Penchem).
(Measured with ETER Model 501)
At 99 nm, the viscosity was 1.6 mPa · s, and no ζ potential was generated. Further, the inkjet ink is heated at 60 ° C.
When a storage test was conducted for 7 days in a constant temperature bath, the dispersion particle size was increased to 195 nm, sedimentation occurred, and the viscosity was increased, and the storage stability was inferior to Example 10.

Table 2 shows the properties of the dispersion compositions of Examples 1 to 10 and Comparative Examples 1 to 7, and Table 3 shows the properties of the jet ink and the wet toner.

[0100]

[Table 2]

[0101]

[Table 3]

[0102]

The dispersion composition of the present invention can improve the dispersion stability of particulate matter, solve the problem of sedimentation, and can maintain charge for a long period of time. Further, it is possible to provide a dispersion composition which is useful for liquid developers and jet inks which utilize a wide range of applications, particularly electrostatic force, by expanding the types of organic solvents and insoluble particulate substances.

──────────────────────────────────────────────────続 き Continued on the front page (51) Int.Cl. ⁷ Identification symbol FI Theme coat ゛ (Reference) C08J 3/24 CER C08J 3/24 CERZ CEZ CEZ C08K 7/16 C08K 7/16 C08L 61/20 C08L 61 / 20 101/02 101/02 C09B 47/08 C09B 47/08 48/00 48/00 Z 67/02 67/02 A 67/20 67/20 L 67/46 67/46 B C09D 11/00 C09D 11 / 00 G03G 9/13 G03G 9/12 321

Claims (22)

[Claims] 1. A dispersion composition comprising a particulate material dispersed in an organic solvent, the dispersion composition comprising at least a polymer compound having an acidic group and a polymer compound having a basic group, wherein at least a part of the polymer compound is used. A dispersion composition which is insoluble in an organic solvent, and wherein a polymer compound is adsorbed on at least a part of the particulate matter. 2. The dispersion composition according to claim 1, wherein the high molecular compound is adsorbed on the particulate matter in an amount of 20 to 10,000 parts by weight based on 100 parts by weight of the particulate matter. 3. The dispersion composition according to claim 1, wherein the high molecular compound having an acidic group has a number average molecular weight of 1,000 to 50,000. 4. The dispersion composition according to claim 1, wherein the polymer compound having a basic group has a number average molecular weight in the range of 1,000 to 50,000. 5. The dispersion composition according to claim 1, wherein the acidic group comprises a carboxyl group. 6. The polymer compound having an acidic group has an acid value of:
The dispersion composition according to claim 1, wherein the composition is in the range of 5 to 200 KOHmg / g. 7. The dispersion composition according to claim 1, wherein the basic group comprises a tertiary amino group. 8. The dispersion composition according to claim 1, wherein the amine value of the polymer compound having a basic group is in the range of 5 to 200 KOH mg / g. 9. The dispersion composition according to claim 1, wherein the polymer compound is cross-linked and adsorbed on the particulate matter. 10. The dispersion composition according to claim 9, wherein the cross-linking is an ester bond or an amide bond. 11. The dispersion composition according to claim 9, further comprising a crosslinking agent. 12. The dispersion composition according to claim 9, wherein the crosslinking agent is an amino resin or an epoxy resin. 13. The polymer compound having an acidic group and / or the polymer compound having a basic group has two or more crosslinking functional groups capable of performing a crosslinking reaction with the acidic group. The dispersion composition according to any one of the preceding claims. 14. The dispersion composition according to claim 13, wherein the crosslinking functional group is a glycidyl group or a hydroxyl group. 15. The dispersion composition according to claim 1, wherein the high molecular compound having an acidic group and the high molecular compound having a basic group are composed of acrylic and / or polyester high molecular compounds. object. 16. The dispersion composition according to claim 1, wherein the particulate material comprises a pigment or a dye. 17. The dispersion composition according to claim 1, wherein the organic solvent comprises an aprotic organic solvent. 18. The method according to claim 17, wherein the aprotic organic solvent has an electric resistivity of 109 Ω · cm or more.
The dispersion composition according to any one of the preceding claims. 19. A dispersion obtained by dispersing a particulate substance in an organic solvent using a polymer compound having an acidic group, and a polymer compound having a basic group in an organic solvent in which the polymer compound having an acidic group does not dissolve. A method for producing a dispersion composition, comprising mixing a polymer compound having an acidic group and / or a polymer compound having a basic group with a particulate substance by mixing with a dispersion in which is dissolved or dispersed. 20. A dispersion in which a granular substance is dispersed in an organic solvent using a polymer compound having a basic group, and a polymer having an acidic group in an organic solvent in which the polymer compound having a basic group does not dissolve. By mixing with a dispersion in which the compound is dissolved or dispersed, a polymer compound having a basic group and / or
Alternatively, a method for producing a dispersion composition, wherein a polymer compound having an acidic group is adsorbed on a granular substance. 21. The method for producing a dispersion composition according to claim 19, wherein crosslinking is performed after the polymer compound is adsorbed on the granular substance. 22. The method for producing a dispersion composition according to claim 19, wherein the organic solvent is concentrated by distillation.