Acidic dispersant, dispersion, molding, and method for producing acidic dispersant

Abstract

To provide an acidic dispersant which has heat resistance, has compatibility with a plurality of resin kinds, is usable for dispersing an object to be dispersed in applications of ink and a molding, and has good productivity.SOLUTION: An acidic dispersant has a first polymer part, a second polymer part, and an acid dianhydride residue, wherein the first polymer part contains a cyclic ester polymer, and the second polymer part contains a vinyl polymer. The acid value of the acidic dispersant is preferably 10 to 200 mgKOH / g.SELECTED DRAWING: None

Description

[Technical field]

[0001] The present invention relates to an acidic pigment dispersant, a dispersion or a molded product, and a method for producing the acidic dispersant. [Background technology]

[0002] In ink applications such as printing inks and inkjet inks, pigments are finely dispersed using resin-type dispersants to enhance color development. Usually, resin-type dispersants are stored in a solution state because they are synthesized by solution polymerization or the like. Therefore, when used to disperse pigments in resin molded bodies (hereinafter referred to as molded bodies) produced in a solvent-free atmosphere, the synthesis solvent of the resin-type dispersant solution becomes an obstacle. However, performing a process of removing the solvent after the synthesis of the resin-type dispersant increases manufacturing costs, which is a productivity problem. Patent Document 1 discloses a polycaprolactone-based dispersant that can be synthesized without using a solvent. [Prior art documents] [Patent documents]

[0003] [Patent Document 1] JP 2008-029901 A Summary of the Invention [Problem to be solved by the invention]

[0004] However, conventional dispersants have the problem that the polycaprolactone chain has high crystallinity, limiting the types of resins with which they are compatible, and also have low heat resistance, which can lead to decomposition during molding.

[0005] An object of the present invention is to provide an acidic dispersant which is heat resistant, compatible with a plurality of resin types, and has good productivity and can be used to disperse materials in ink and molded product applications. [Means for solving the problem]

[0006] The present invention provides an acidic dispersant having a first polymer portion, a second polymer portion, and an acid dianhydride residue, the first polymer portion comprises a cyclic ester polymer, The second polymer portion is an acidic dispersant that includes a vinyl polymer. Effect of the Invention

[0007] According to the present invention, it is possible to provide an acidic dispersant having heat resistance, compatibility with a plurality of resin types, and good productivity that can be used for dispersing a substance to be dispersed in ink and molded body applications, and a method for producing the acidic dispersant.The present invention also provides a dispersion and a molded body. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0008] The terms used in this specification are defined below. When "(meth)acryloyl", "(meth)acrylic", "(meth)acrylic acid", "(meth)acrylate", or "(meth)acrylamide" is written, it means "acryloyl and / or methacryloyl", "acrylic and / or methacrylic", "acrylic acid and / or methacrylic acid", "acrylate and / or methacrylate", or "acrylamide and / or methacrylamide", respectively, unless otherwise specified. In addition, in this specification, "CI" means color index (CI). A vinyl monomer is an ethylenically unsaturated monomer. An acid dianhydride is a compound having two acid anhydride groups.

[0009] The acidic dispersant of the present invention is an acidic dispersant having a first polymer portion, a second polymer portion, and an acid dianhydride residue, wherein the first polymer portion contains a cyclic ester polymer, and the second polymer portion contains a vinyl polymer. The acidic dispersant of the present invention is preferably used for dispersing colorants such as pigments and dyes for applications such as inks, paints, molded bodies, color filters, etc., and for dispersing particles such as metal particles, etc. Among these applications, the application to color filters is preferred.

[0010] In the acidic dispersant of the present invention, the first polymer portion contains a cyclic ester polymer and has a steric repulsion portion with a narrow molecular weight distribution derived from the cyclic ester polymer, which contributes to dispersion stability. The second polymer portion contains a vinyl polymer having excellent heat resistance, and the affinity of the vinyl polymer to the resin type and the dispersion solvent can be controlled by appropriately selecting the vinyl monomer unit. In addition, since the vinyl polymer has high heat resistance, the heat resistance of the entire dispersant can be further improved. In addition, the heat resistance of the vinyl polymer can be further improved by introducing, for example, a crosslinking group. The acidic dispersant of the present invention is capable of suppressing unbound cyclic ester polymers and vinyl polymers, since the first polymer portion and the second polymer portion, which are different in composition, are bonded to the acid dianhydride residue. This allows the acidic dispersant to suppress the decrease in heat resistance caused by the presence of low molecular weight components, and also contributes to suppressing residues in applications in which photolithography is performed, for example. In addition, the acid dianhydride residue has carboxyl groups bonded at the ends of the first polymer portion and the second polymer portion, so that the carboxyl groups are regularly arranged and become strong adsorbents for the dispersed material. This allows the acidic dispersant to adsorb to and stably disperse a wide range of materials, regardless of whether they are organic or inorganic particles.

[0011] <Acidic dispersant> The acidic dispersant of the present invention is an acidic dispersant having a first polymer portion, a second polymer portion, and an acid dianhydride residue, wherein the first polymer portion contains a cyclic ester polymer, and the second polymer portion contains a vinyl polymer.

[0012] <First polymer portion> The cyclic ester polymer forming the first polymer portion has a hydroxyl group at its terminal portion that can react with an acid dianhydride. The cyclic ester polymer can be synthesized by ring-opening polymerization of a cyclic ester using an active hydrogen compound as an initiator to obtain a cyclic ester polymer having a hydroxyl group at one terminal. The polymerization reaction of the cyclic ester is controlled by using the initiator, so that a cyclic ester polymer having a narrow molecular weight distribution can be obtained.

[0013] The cyclic ester polymer preferably contains a polymer (polylactone) of lactone, which is a cyclic ester. Examples of lactone include 3- to 16-membered cyclic esters such as α-acetolactone, β-propiolactone, γ-butyrolactone, δ-valerolactone, ε-caprolactone, ζ-enantholactone, η-caprylolactone (=8-hydroxyoctanoic acid lactone), 12-hydroxydodecanoic acid lactone, 13-hydroxytridecanoic acid lactone, 14-hydroxytetradecanoic acid lactone, and 15-hydroxypentadecanoic acid lactone. Among these, δ-valerolactone and ε-caprolactone are preferred, and ε-caprolactone is more preferred, from the viewpoint of reaction control. Note that, as long as the problem of the present application can be solved, the cyclic ester polymer may be a compound other than lactone.

[0014] In addition to lactones, copolymerizable cyclic compounds can be used to synthesize the cyclic ester polymer. Examples of the cyclic compound include lactide, trimethylene carbonate, glycolide, and lactam. In the mass of the cyclic ester polymer, the polylactone is preferably 50% by mass or more, and more preferably 70% by mass or more. The mass is preferably 90% by mass or more, and more preferably 100% by mass.

[0015] The cyclic esters can be used alone or in combination of two or more kinds.

[0016] <Synthesis of the first polymer segment> <Active hydrogen compounds> The active hydrogen compound used for synthesizing the cyclic ester polymer is not limited as long as it can provide the active hydrogen that contributes to the polymerization of the cyclic ester to the polymerization site.In this specification, the active hydrogen compound is preferably a compound having at least one functional group selected from hydroxyl group, carboxyl group, phosphoric acid group, amino group, and thiol group.Among these, a compound having a hydroxyl group is preferred in terms of excellent reactivity, and a monoalcohol is more preferred in terms of reaction control.

[0017] Examples of monoalcohols include methanol, ethanol, 1-propanol, isopropanol, 1-butanol, isobutanol, tert-butanol, 1-pentanol, isopentanol, 1-hexanol, cyclohexanol, 4-methyl-2-pentanol, 1-heptanol, 1-octanol, isooctanol, 2-ethylhexanol, 1-nonanol, isononanol, 1-decanol, 1-dodecanol, 1-myristyl alcohol, cetyl alcohol, 1-stearyl alcohol, isostearyl alcohol, 2-octyl alcohol, and the like. aliphatic monoalcohols such as dodecanol, 2-octyldodecanol, 2-hexyldecanol, behenyl alcohol, and oleyl alcohol; aromatic ring-containing monoalcohols such as benzyl alcohol, phenoxyethyl alcohol, and paracumylphenoxyethyl alcohol; ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, ethylene glycol monohexyl ether, ethylene glycol mono-2-ethylhexyl ether, propylene glycol glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monopropyl ether, propylene glycol monobutyl ether, propylene glycol monohexyl ether, propylene glycol mono-2-ethylhexyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monopropyl ether, diethylene glycol monobutyl ether, diethylene glycol monohexyl ether, diethylene glycol mono-2-ethylhexyl ether, dipropylene glycol monomethyl ether, dipropylene glycol monoethyl ether, dipropylene glycol monopropyl ether, dipropylene glycol monobutyl ether, dipropylene glycol monohexyl ether, dipropylene glycol mono-2-ethylhexyl ether, triethylene glycol monomethyl ether, triethylene glycol monoethyl ether, triethylene glycol monopropyl ether, triethylene glycol monobutyl ether, triethylene glycol monohexyl ether,Examples of the alkylene glycol monoalkyl ethers include triethylene glycol mono-2-ethylhexyl ether, tripropylene glycol monomethyl ether, tripropylene glycol monoethyl ether, tripropylene glycol monopropyl ether, tripropylene glycol monobutyl ether, tripropylene glycol monohexyl ether, tripropylene glycol mono-2-ethylhexyl ether, tetraethylene glycol monomethyl ether, tetraethylene glycol monoethyl ether, tetraethylene glycol monopropyl ether, tetraethylene glycol monobutyl ether, tetraethylene glycol monohexyl ether, tetraethylene glycol mono-2-ethylhexyl ether, tetrapropylene glycol monomethyl ether, tetrapropylene glycol monoethyl ether, tetrapropylene glycol monopropyl ether, tetrapropylene glycol monobutyl ether, tetrapropylene glycol monohexyl ether, tetrapropylene glycol mono-2-ethylhexyl ether, and tetradiethylene glycol monomethyl ether; and reactive alcohols such as 3-ethyl-3-oxetane methanol and 3-ethyl-3-(4-hydroxybutyloxymethyl)oxetane. The monoalcohols can be used alone or in combination of two or more kinds.

[0018] For the ring-opening polymerization, it is preferable to use a monoalcohol having a molecular weight of 100 to 300. By making the molecular weight 300 or less, a first polymer portion having a sharp molecular weight distribution is obtained, and the dispersibility of the acidic dispersant is improved. In addition, by making the molecular weight 100 or more, ring-opening polymerization of the cyclic ester becomes possible at high temperatures, and the yield is improved.

[0019] The amount of the initiator used is preferably 0.1 to 100 mol, more preferably 0.5 to 100 mol, and even more preferably 1 to 100 mol, relative to 100 mol of the cyclic ester. By controlling the molar ratio of the cyclic ester to the initiator, the molecular weight of the cyclic ester polymer can be adjusted.

[0020] A polymerization catalyst can be used for the ring-opening polymerization. The use of a polymerization catalyst can lower the reaction temperature and shorten the reaction time. Examples of the polymerization catalyst include quaternary ammonium salts such as tetramethylammonium chloride, tetrabutylammonium chloride, tetramethylammonium bromide, tetrabutylammonium bromide, tetramethylammonium iodide, tetrabutylammonium iodide, benzyltrimethylammonium chloride, benzyltrimethylammonium bromide, and benzyltrimethylammonium iodide; tetramethylphosphonium chloride, tetrabutylphosphonium chloride, tetramethylphosphonium bromide, tetrabutylphosphonium bromide, tetramethylphosphonium iodide, tetrabutylphosphonium iodide, benzyltrimethylphosphonium chloride, and benzyltrimethylphosphonium bromide; quaternary phosphonium salts such as tetraphenylphosphonium bromide, benzyltrimethylphosphonium iodide, tetraphenylphosphonium chloride, tetraphenylphosphonium bromide, and tetraphenylphosphonium iodide; phosphorus compounds such as triphenylphosphine; organic tin compounds such as monomethyltin oxide, monobutyltin oxide, monooctyltin oxide, dibutyltin oxide, and dioctyltin dilaurate; organic carboxylates such as potassium acetate, sodium acetate, potassium benzoate, and sodium benzoate; alkali metal alcoholates such as sodium alcoholate and potassium alcoholate, as well as tertiary amines, organic aluminum compounds, organic titanate compounds, and zinc compounds such as zinc chloride.

[0021] The amount of the polymerization catalyst used is preferably 0.1 ppm to 3000 ppm, more preferably 1 ppm to 1000 ppm, based on 100 parts by mass of the cyclic ester. When used within this range, a colorless cyclic ester polymer is easily obtained at a polymerization rate suitable for production.

[0022] The polymerization temperature of the cyclic ester is preferably 100° C. to 220° C., more preferably 110° C. to 210° C. When the polymerization is carried out within the above range, a cyclic ester polymer with less by-products can be easily obtained at a polymerization rate suitable for production.

[0023] The weight average molecular weight of the cyclic ester polymer is preferably 500 to 10,000, more preferably 1,000 to 8,000, and even more preferably 1,000 to 5,000. When the molecular weight is 500 or more, the pigment dispersibility can be further improved due to the steric repulsion effect. When the molecular weight is 10,000 or less, appropriate crystallinity and solvent solubility are obtained, so that the dispersibility is further improved.

[0024] <Second polymer portion> The vinyl polymer forming the second polymer portion has a hydroxyl group at its terminal that can react with an acid dianhydride. A vinyl polymer having a hydroxyl group at one terminal can be synthesized by polymerizing a vinyl monomer in the presence of a thiol group-containing alcohol compound.

[0025] Examples of vinyl monomers include methyl (meth)acrylate, ethyl (meth)acrylate, propyl (meth)acrylate, isopropyl (meth)acrylate, butyl (meth)acrylate, isobutyl (meth)acrylate, tert-butyl (meth)acrylate, isoamyl (meth)acrylate, octyl (meth)acrylate, isooctyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, cetyl (meth)acrylate, decyl (meth)acrylate, isodecyl (meth)acrylate, lauryl (meth)acrylate, and the like. ) acrylate, tridecyl (meth)acrylate, isomyristyl (meth)acrylate, stearyl (meth)acrylate, or isostearyl (meth)acrylate, methoxyethyl (meth)acrylate, methoxypolyethylene glycol (meth)acrylate, methoxypolypropylene glycol (meth)acrylate, methoxypolytetramethylene glycol (meth)acrylate, or methoxypolyethylene glycol polypropylene glycol (meth)acrylate, or other linear or branched alkyl (meth)acrylates; cyclic alkyl (meth)acrylates such as cyclohexyl (meth)acrylate, tert-butylcyclohexyl (meth)acrylate, dicyclopentanyl (meth)acrylate, dicyclopentanyloxyethyl (meth)acrylate, dicyclopentenyl (meth)acrylate, dicyclopentenyloxyethyl (meth)acrylate, or isobornyl (meth)acrylate; Fluoroalkyl (meth)acrylates such as trifluoroethyl (meth)acrylate, octafluoropentyl (meth)acrylate, perfluorooctylethyl (meth)acrylate, or tetrafluoropropyl (meth)acrylate; (Meth)acryloxy-modified polydimethylsiloxane (silicone macromer); (meth)acrylates having a heterocycle, such as tetrahydrofurfuryl (meth)acrylate, glycidyl (meth)acrylate, 3-methyl-3-methacryloyloxymethyloxetane, 3-methyl-3-acryloyloxymethyloxetane, 3-ethyl-3-methacryloyloxymethyloxetane, 3-ethyl-3-acryloyloxymethyloxetane, 3-methyl-3-methacryloyloxyethyloxetane, 3-methyl-3-acryloyloxyethyloxetane, 3-ethyl-3-methacryloyloxyethyloxetane, 3-ethyl-3-acryloyloxyethyloxetane, and 3-ethyl-3-acryloyloxyethyloxetane; (meth)acrylates having an aromatic ring, such as benzyl (meth)acrylate, phenoxyethyl (meth)acrylate, phenoxypolyethylene glycol (meth)acrylate, paracumylphenoxyethyl (meth)acrylate, paracumylphenoxypolyethylene glycol (meth)acrylate, or nonylphenoxypolyethylene glycol (meth)acrylate; (meth)acrylates having a carboxyl group, such as (meth)acrylic acid, acrylic acid dimer, 2-(meth)acryloyloxyethyl phthalate, 2-(meth)acryloyloxypropyl phthalate, 2-(meth)acryloyloxyethyl hexahydrophthalate, 2-(meth)acryloyloxypropyl hexahydrophthalate, ethylene oxide-modified succinic acid (meth)acrylate, β-carboxyethyl (meth)acrylate, or ω-carboxypolycaprolactone (meth)acrylate; Vinyl such as styrene, α-methylstyrene, vinyl acetate, vinyl (meth)acrylate, or allyl (meth)acrylate; N-substituted (meth)acrylamide such as (meth)acrylamide, N,N-dimethyl(meth)acrylamide, N,N-diethyl(meth)acrylamide, N-isopropyl(meth)acrylamide, diacetone(meth)acrylamide, or acryloylmorpholine; Amino group-containing (meth)acrylates such as N,N-dimethylaminoethyl (meth)acrylate or N,N-diethylaminoethyl (meth)acrylate; Nitriles such as (meth)acrylonitrile; (meth)acrylates having a blocked isocyanate group, such as 2-[(3,5-dimethylpyrazolyl)carbonylamino]ethyl (meth)acrylate and 2-[0-(1'-methylpropylideneamino)carboxyamino]ethyl (meth)acrylate, are examples.

[0026] The vinyl polymer preferably contains a thermal crosslinking group such as a vinyl monomer having a t-butyl group, a vinyl monomer having an oxetane group, or a vinyl monomer having a blocked isocyanate group. Specifically, vinyl monomers having a t-butyl group such as t-butyl methacrylate and t-butyl acrylate, vinyl monomers having an oxetane group such as 3-ethyl-3-methacryloyloxymethyloxetane and 3-ethyl-3-acryloyloxymethyloxetane, and vinyl monomers having a blocked isocyanate group such as 2-[(3,5-dimethylpyrazolyl)carbonylamino]ethyl(meth)acrylate and 2-[0-(1'-methylpropylideneamino)carboxyamino]ethyl(meth)acrylate are preferred. By having these thermal crosslinking groups, the heat resistance of the acidic dispersant is improved.

[0027] The amount of the vinyl monomer having a thermal crosslinking group used is preferably 5 to 90% by weight, more preferably 20 to 60% by weight, of the monomers used in the synthesis of the vinyl polymer. When used in an appropriate amount, the crosslinking effect can be obtained without impairing the polymerization stability.

[0028] <Thiol group-containing alcohol compound> The thiol group-containing alcohol compound is preferably a compound having one or more hydroxyl groups and a thiol group in the molecule, more preferably a compound having two hydroxyl groups and one thiol group in the molecule, which allows the vinyl polymer to form a second polymer portion by reaction with the acid dianhydride.

[0029] Examples of compounds having two hydroxyl groups and one thiol group in the molecule include 1-mercapto-1,1-methanediol, 1-mercapto-1,1-ethanediol, 3-mercapto-1,2-propanediol (thioglycerol), 2-mercapto-1,2-propanediol, 2-mercapto-2-methyl-1,3-propanediol, 2-mercapto-2-ethyl-1,3-propanediol, 1-mercapto-2,2-propanediol, 2-mercaptoethyl-2-methyl-1,3-propanediol, and 2-mercaptoethyl-2-ethyl-1,3-propanediol. Examples of compounds having one hydroxyl group and one thiol group in the molecule include mercaptomethanol, 2-mercaptoethanol, 3-mercapto-1-propanol, 1-mercapto-2-butanol, 2-mercapto-3-butanol, etc. Among these, compounds having two hydroxyl groups and one thiol group in the molecule are preferred, and 3-mercapto-1,2-propanediol is more preferred from the viewpoints of polymerization control and odor.

[0030] The amount of the compound having two hydroxyl groups and one thiol group used is preferably 1 to 10 parts by mass, more preferably 2 to 9% by mass, and even more preferably 3 to 8% by mass, based on 100 parts by mass of the total vinyl monomers. When an appropriate amount is used, a vinyl polymer of an appropriate molecular weight that functions as a steric repulsion site of the dispersant is easily obtained, and viscosity stability is improved.

[0031] The polymerization temperature is preferably 40 to 150° C., more preferably 50 to 110° C. If the polymerization is carried out at a moderate temperature, it is easy to control the polymerization reaction and adjust the molecular weight.

[0032] A polymerization initiator is used for the polymerization of the vinyl monomer. The amount of the polymerization initiator used is preferably 0.001 to 5 parts by mass based on 100 parts by mass of the monomer. Examples of the polymerization initiator include an azo compound and an organic peroxide.

[0033] Examples of azo compounds include 2,2'-azobisisobutyronitrile, 2,2'-azobis(2-methylbutyronitrile), 1,1'-azobis(cyclohexane-1-carbonitrile), 2,2'-azobis(2,4-dimethylvaleronitrile), 2,2'-azobis(2,4-dimethyl-4-methoxyvaleronitrile), dimethyl 2,2'-azobis(2-methylpropionate), 4,4'-azobis(4-cyanovaleric acid), 2,2'-azobis(2-hydroxymethylpropionitrile), and 2,2'-azobis[2-(2-imidazolin-2-yl)propane].

[0034] Examples of organic peroxides include benzoyl peroxide, tert-butyl perbenzoate, cumene hydroperoxide, diisopropyl peroxydicarbonate, di-n-propyl peroxydicarbonate, di(2-ethoxyethyl)peroxydicarbonate, t-butyl peroxyneodecanoate, tert-butyl peroxypivalate, (3,5,5-trimethylhexanoyl)peroxide, dipropionyl peroxide, and diacetyl peroxide.

[0035] The polymerization initiators can be used alone or in combination of two or more kinds.

[0036] The weight-average molecular weight of the vinyl polymer is preferably from 1,000 to 20,000. When it is within this range, the heat melt viscosity of the acidic dispersant is low, and the productivity is improved without impairing the heat resistance.

[0037] <Acid dianhydride residue> The acidic dispersant of the present invention has an acid dianhydride residue. The acid dianhydride residue is generated by reacting a terminal hydroxyl group of the first polymer portion or the second polymer portion with an acid dianhydride.

[0038] <Acid dianhydride> Examples of the acid dianhydride include aliphatic tetracarboxylic dianhydrides, aromatic tetracarboxylic dianhydrides, and polycyclic tetracarboxylic dianhydrides.

[0039] Examples of the aliphatic tetracarboxylic dianhydride include 1,2,3,4-butane tetracarboxylic dianhydride, 1,2,3,4-cyclobutane tetracarboxylic dianhydride, 1,3-dimethyl-1,2,3,4-cyclobutane tetracarboxylic dianhydride, 1,2,3,4-cyclopentane tetracarboxylic dianhydride, 2,3,5-tricarboxycyclopentylacetic dianhydride, 2,3,5,6-tetracarboxycyclohexane dianhydride, 2,3,5,6-tetracarboxynorbornane dianhydride, 3,5,6-tricarboxynorbornane-2-acetic dianhydride, 2,3,4,5-tetrahydrofuran tetracarboxylic dianhydride, 5-(2,5-dioxotetrahydrofural)-3-methyl-3-cyclohexene-1,2-dicarboxylic dianhydride, and bicyclo[2,2,2]-oct-7-ene-2,3,5,6-tetracarboxylic dianhydride.

[0040] Examples of the aromatic tetracarboxylic dianhydride include pyromellitic dianhydride, ethylene glycol ditrimellitic anhydride, propylene glycol ditrimellitic anhydride, butylene glycol ditrimellitic anhydride, 3,3',4,4'-benzophenone tetracarboxylic dianhydride, and 2,2',3,3'-benzophenone tetracarboxylic dianhydride. Carboxylic acid dianhydrides, 3,3',4,4'-biphenylsulfone tetracarboxylic dianhydride, 2,2',3,3'-biphenylsulfone tetracarboxylic dianhydride, 1,4,5,8-naphthalene tetracarboxylic dianhydride, 2,3,6,7-naphthalene tetracarboxylic dianhydride, 3,3',4,4'-biphenyl ether tetracarboxylic dianhydride, 3,3',4,4'-dimethyldiphenylsilane tetracarboxylic dianhydride, 3,3',4,4'-tetraphenylsilane tetracarboxylic dianhydride, 1,2,3,4-furan tetracarboxylic dianhydride, 4,4'-bis(3,4-dicarboxyphenoxy)diphenyl sulfide dianhydride, 4,4'-bis(3,4-dicarboxyphenoxy)diphenyl sulfone dianhydride, 4,4 Examples of suitable dianhydrides include 3,3',4,4'-bis(3,4-dicarboxyphenoxy)diphenylpropane dianhydride, 3,3',4,4'-perfluoroisopropylidenediphthalic dianhydride, 3,3',4,4'-biphenyltetracarboxylic dianhydride, bis(phthalic acid)phenylphosphine oxide dianhydride, p-phenylene-bis(triphenylphthalic acid) dianhydride, M-phenylene-bis(triphenylphthalic acid) dianhydride, bis(triphenylphthalic acid)-4,4'-diphenyl ether dianhydride, bis(triphenylphthalic acid)-4,4'-diphenylmethane dianhydride, 9,9-bis(3,4-dicarboxyphenyl)fluorene dianhydride, and 9,9-bis[4-(3,4-dicarboxyphenoxy)phenyl]fluorene dianhydride.

[0041] Examples of the polycyclic tetracarboxylic dianhydride include 3,4-dicarboxy-1,2,3,4-tetrahydro-1-naphthalene succinic dianhydride and 3,4-dicarboxy-1,2,3,4-tetrahydro-6-methyl-1-naphthalene succinic dianhydride.

[0042] Among these, from the viewpoints of reactivity and adsorption to pigments, aliphatic tetracarboxylic acid dianhydrides and aromatic tetracarboxylic acid dianhydrides are more preferred, and aromatic tetracarboxylic acid dianhydrides are even more preferred. In other words, the acid anhydride residue is preferably a residue having an aromatic ring.

[0043] <Method of manufacturing acidic dispersant> As described above, the acidic dispersant used in this specification may be any dispersant having a first polymer portion, a second polymer portion, and an acid dianhydride residue, and the synthesis method thereof is not limited. In the present specification, the method for producing an acidic dispersant includes the steps of: (1) reacting a thiol group-containing alcohol with a vinyl monomer in the presence of a polymer containing a cyclic ester polymer having a hydroxyl group at one end to synthesize a vinyl polymer having a hydroxyl group at one end; It is preferable to then have a step (2) of reacting these polymers with an acid dianhydride to synthesize an acidic dispersant having a first polymer portion containing a cyclic ester polymer, a second polymer portion containing a vinyl polymer, and an acid dianhydride residue.

[0044] In the step (1), a vinyl polymer having a hydroxyl group at one end is synthesized by reacting a thiol group-containing alcohol with a vinyl monomer in the presence of a cyclic ester polymer synthesized as described above. The cyclic ester polymer functions as a reaction solvent during polymerization of the vinyl monomer, so that the polymerization can be performed without using an organic solvent. Note that the above description does not exclude the use of an organic solvent during the polymerization. The synthesis of the vinyl polymer is as described above.

[0045] The acid dianhydride used in the step (2) is as already explained.

[0046] The amount of the acid dianhydride used is preferably 0.5 to 1.5 mol, more preferably 0.6 to 1.2 mol, and even more preferably 0.7 to 1.0 mol, when the total amount of hydroxyl groups in the cyclic ester polymer and the vinyl polymer is taken as 1 mol. By reacting an appropriate amount, an acidic dispersant in which the acid dianhydride residue in the pigment adsorption site and the first polymer site and the second polymer site in the steric repulsion site are appropriately bonded can be obtained.

[0047] In the step (2), an esterification catalyst can be used. The esterification catalyst is preferably a tertiary amine. Examples of the tertiary amine include triethylamine, triethylenediamine, N,N-dimethylbenzylamine, N-methylmorpholine, 1,8-diazabicyclo-[5.4.0]-7-undecene, and 1,5-diazabicyclo-[4.3.0]-5-nonene.

[0048] The reaction temperature in the step (2) is preferably 40 to 150° C., more preferably 50 to 120° C. If the reaction is carried out at a moderate temperature, the reaction can be easily controlled.

[0049] During the reaction in step (2), the acid anhydride groups can be reacted with an end-capping material (e.g., monoalcohol, monoamine) to form capping sites, which improves the storage stability of the acidic dispersant.

[0050] The blocked portion can be formed by adding and reacting a terminal blocking material when 70 to 98% of the acid anhydride groups have reacted. The terminal blocking material is more preferably added when 75 to 95% of the acid anhydride groups have reacted.

[0051] The amount of the terminal blocking agent used is preferably an amount corresponding to 40 to 90 mol %, more preferably an amount corresponding to 50 to 90 mol %, and even more preferably an amount corresponding to 60 to 85 mol %, when the acid anhydride groups present at the time of adding the terminal blocking agent are taken as 100 mol %. Adding an appropriate amount can suppress unreacted acid anhydride groups, thereby further improving the storage stability of the acidic dispersant itself and the dispersion.

[0052] Examples of monoalcohols include monoalcohols such as methanol, ethanol, 1-butanol, 2-butanol, isobutanol, tert-butanol, 1-pentanol, isopentyl alcohol, tert-pentyl alcohol, cyclopentanol, 1-hexanol, cyclohexanol, 1-heptanol, 1-octanol, 2-ethyl-1-hexanol, isononyl alcohol, 1-nonyl alcohol, amyl alcohol, lauryl alcohol, n-butyl alcohol, isobutyl alcohol, cyclohexanol, benzyl alcohol, and methylcyclohexanol; monoalcohols having an ether group, such as 3-methoxy-3-methyl-1-butanol, 3-methoxybutanol, ethylene glycol monoisopropyl ether, ethylene glycol monoethyl ether, ethylene glycol monotertiary butyl ether, ethylene glycol monobutyl ether, ethylene glycol monopropyl ether, ethylene glycol monohexyl ether, ethylene glycol monomethyl ether, diethylene glycol monoisopropyl ether, diethylene glycol monobutyl ether, diethylene glycol monomethyl ether, dipropylene glycol monoethyl ether, dipropylene glycol monobutyl ether, dipropylene glycol monopropyl ether, dipropylene glycol monomethyl ether, tripropylene glycol monobutyl ether, tripropylene glycol monomethyl ether, propylene glycol monophenyl ether, propylene glycol monoethyl ether, propylene glycol monobutyl ether, propylene glycol monopropyl ether, and propylene glycol monomethyl ether; Examples of the lactate include monoalcohols having a carbonyl group, such as methyl lactate, ethyl lactate, and diacetone alcohol.

[0053] The monoalcohol is preferably a compound having an ether group or a carbonyl group. The acidic dispersant can have an ether group or a carbonyl group at the acid dianhydride residue, and the affinity with various solvents contained in the dispersion, such as acetate-based solvents such as propylene glycol monomethyl ether acetate, is improved, and the dispersibility of the acidic dispersant is improved. Among these, the monoalcohol is preferably 3-methoxybutanol, propylene glycol monomethyl ether, or diacetone alcohol.

[0054] From the viewpoint of reaction control, the monoamine is preferably a secondary amine. By using a secondary amine, side reactions such as a crosslinking reaction with an acid dianhydride can be suppressed. Examples of secondary amines include aliphatic secondary amines such as dimethylamine, diethylamine, ethylmethylamine, di-n-propylamine, diisopropylamine, di-n-butylamine, diisobutylamine, di-s-butylamine, di-tert-butylamine, N-methylbutylamine, N-ethylbutylamine, di-n-pentylamine, di-n-hexylamine, di-n-heptylamine, di-n-octylamine, di-2-ethylhexylamine, di-n-decylamine, di-n-undecylamine, di-n-dodecylamine (dilaurylamine), di-n-tridecylamine, di-n-tetradecylamine (dimyristylamine), di-n-hexadecylamine (dipalmitylamine), di-n-stearylamine, and diisostearylamine; Alicyclic secondary amines such as N-methylcyclopentylamine, N-ethylcyclopentylamine, N-propylcyclopentylamine, N-methylcyclohexylamine, N-ethylcyclohexylamine, N-propylcyclohexylamine, and N-isopropylcyclohexylamine; Examples of the aromatic secondary amines include N-methylaniline, N-ethylaniline, N-propylaniline, N-isopropylaniline, N-butylaniline, N-isobutylaniline, N-methylbenzylamine, N-ethylbenzylamine, N-propylbenzylamine, N-isopropylbenzylamine, N-butylbenzylamine, 1-(methylaminomethyl)naphthalene, and 9-(methylamino)methylanthracene.

[0055] The end-capping material is preferably a monoalcohol. This makes it easier to control the reaction during synthesis of the acidic dispersant. It also improves dispersibility and solubility in PGMAc.

[0056] The acidic dispersant preferably contains 20 to 80% by mass of the first polymer moiety, more preferably 30 to 70% by mass, and even more preferably 40 to 65% by mass. By containing 20% ​​or more by mass of the first polymer moiety, the balance between thermal melting property and crystallinity is excellent, and reaction control during polymerization and handling property of the acidic dispersant at room temperature are improved. By controlling the content of the first polymer moiety to 80% by mass or less, an acidic dispersant having excellent viscosity stability and heat resistance can be obtained.

[0057] The acidic dispersant contains the second polymer moiety in an amount of preferably 5 to 70% by mass, more preferably 10 to 65% by mass, and even more preferably 20 to 60% by mass. By containing 5% or more by mass of the second polymer moiety, an acidic dispersant having excellent viscosity stability and heat resistance can be obtained. By controlling the content of the second polymer moiety to 70% by mass or less, the viscosity of the acidic dispersant during heat melting is reduced, and the productivity of the acidic dispersant is improved.

[0058] The ratio of the first polymer moiety to the second polymer moiety in the acidic dispersant is preferably 0.3 to 5.0, more preferably 0.4 to 4.0, and most preferably 0.5:1 to 3.0, when the second polymer moiety is taken as 1. By setting the ratio within the above range, a dispersant with further improved viscosity stability and heat resistance can be obtained. [Molecular weight] The weight average molecular weight of the acidic dispersant of the present invention is preferably 2,000 to 35,000, more preferably 2,000 to 30,000, and even more preferably 3,000 to 20,000. When the molecular weight is 2,000 or more, the dispersion stability of the pigment is further improved due to the steric repulsion effect of the first polymer portion and the second polymer portion, and the heat resistance is further improved. When the molecular weight is 35,000 or less, the viscosity of the acidic dispersant when heated and melted is reduced, and the moldability is further improved in the application of molded bodies.

[0059] [Acid value] The acid value of the acidic dispersant of the present invention is preferably 10 to 200 mgKOH / g, more preferably 20 to 150 mgKOH / g, even more preferably 30 to 120 mgKOH / g, and most preferably 30 to 110 mgKOH / g. When the acid value is 10 mgKOH / g or more, the pigment adsorption ability is improved and the pigment dispersibility is further improved. On the other hand, when the acid value is 200 mgKOH / g or less, there is no excessive interaction between resins, and for example, the viscosity of the pigment dispersion can be kept low.

[0060] <Dispersion> The dispersion of the present invention preferably contains an acidic dispersant and a substance to be dispersed. The substance to be dispersed is dispersible particles including organic particles such as colorants and inorganic particles such as metals.

[0061] The content of the acidic dispersant in the dispersion is preferably 0.01 to 100 parts by mass, more preferably 0.01 to 60% by mass, and even more preferably 5 to 40% by mass, based on the mass of the colorant. When an appropriate amount is contained, a good dispersing effect can be obtained and the viscosity of the dispersion can be suppressed.

[0062] The dispersion of the present invention can be used in applications that use pigment dispersions, such as color filters, offset inks, inkjet inks, etc. Hereinafter, the application to color filters will be described as an example.

[0063] <Coloring agent> The colorant includes a pigment. Examples of the pigment include organic pigments and inorganic pigments. The pigment is preferably an organic pigment having high color development and high resistance to thermal decomposition. Specific examples of organic pigments are shown below with their color index numbers.

[0064] Red pigments include, for example, CI Pigment Red 1, 2, 3, 4, 5, 6, 7, 8, 9, 12, 14, 15, 16, 17, 21, 22, 23, 31, 32, 37, 38, 41, 47, 48, 48:1, 48:2, 48:3, 48:4, 49, 49:1, 49:2, 50:1, 52:1, 52:2, 53, 53:1, 53:2, 53:3, 57, 57:1, 57:2 , 58:4, 60, 63, 63:1, 63:2, 64, 64:1, 68, 69, 81, 81:1, 81:2, 81:3, 81:4, 83, 88, 90:1, 101, 101:1, 104, 108, 108:1, 109, 112, 113, 114, 122, 123, 144, 146, 147, 149, 151, 166, 168, 169, 170, 172, 173, 174, 175, 176, 177, 178, 179, 181, 184, 185, 187, 188, 190, 193, 194, 200, 202, 206, 207, 208, 209, 210, 214, 216, 220, 221, 224, 230, 231, 232, 233, 235, 236, 237, 238, 239, 242, 243, 245, 247, 249, 2 50, 251, 253, 254, 255, 256, 257, 258, 259, 260, 262, 263, 264, 265, 266, 267, 268, 269, 270, 271, 272, 273, 274, 275, 276, 277, 278, 279, 280, 281, 282, 283, 284, 285, 286, 287, 291, 295, 296, etc. Among these, from the viewpoints of heat resistance, light resistance, and transmittance of the filter segment, CI Pigment Red 48:1, 122, 177, 224, 242, 269, 254, 291, 295, and 296 are preferred, and CI Pigment Red 177, 254, 291, 295, and 296 are more preferred.

[0065] Examples of orange pigments include CI Pigment Orange 36, 38, 43, 51, 55, 59, 61, 71, and 73.

[0066] Examples of blue pigments include CI Pigment Blue 1, 1:2, 9, 14, 15, 15:1, 15:2, 15:3, 15:4, 15:6, 16, 17, 19, 25, 27, 28, 29, 33, 35, 36, 56, 56:1, 60, 61, 61:1, 62, 63, 66, 67, 68, 71, 72, 73, 74, 75, 76, 78, and 79. Among these, from the viewpoints of heat resistance, light resistance, and transmittance of the filter segment, CI Pigment Blue 15, 15:1, 15:2, 15:3, 15:4, or 15:6 is preferred, and CI Pigment Blue 15:6 is more preferred.

[0067] Examples of purple pigments include CI Pigment Violet 1, 1:1, 2, 2:2, 3, 3:1, 3:3, 5, 5:1, 14, 15, 16, 19, 23, 25, 27, 29, 31, 32, 37, 39, 42, 44, 47, 49, and 50. Among these, from the viewpoints of heat resistance, light fastness, and transmittance of the filter segment, CI Pigment Violet 19 or 23 is preferred, and CI Pigment Violet 23 is more preferred.

[0068] Examples of green pigments include CI Pigment Green 1, 2, 4, 7, 8, 10, 13, 14, 15, 17, 18, 19, 26, 36, 37, 45, 48, 50, 51, 54, 55, 58, 59, 62, and 63. Among these, CI Pigment Green 36, 58, 59, 62, and 63 are preferred from the viewpoint of transmittance.

[0069] Yellow pigments include, for example, CI Pigment Yellow 1, 2, 3, 4, 5, 6, 10, 12, 13, 14, 15, 16, 17, 18, 24, 31, 32, 34, 35, 35:1, 36, 36:1, 37, 37:1, 40, 42, 43, 53, 55, 60, 61, 62, 63, 65, 73, 74, 77, 81, 83, 93, 94, 95, 97, 98, 100, 101, 104, 106, 108, 109, 110, 113, 114, 115, 116, 117, 118 , 119, 120, 123, 126, 127, 128, 129, 138, 139, 147, 150, 151, 152, 153, 154, 155, 156, 161, 162, 164, 166, 167, 168, 169, 170, 171, 172, 173, 174, 175, 176, 177, 179, 180, 181, 182, 185, 187, 188, 192, 193, 194, 196, 198, 199, 213, 214, 231, 233, etc. Among these, CI Pigment Yellow 138, 139, 150, 185, 231, 233 are preferable.

[0070] Examples of blue pigments include CI Pigment Blue 15:1, 15:2, 15:4, 15:3, 15:6, 16, 81, and the like.

[0071] Examples of purple pigments include CI Pigment Violet 1 and 19, and CI Pigment Red 144, 146, 177, 169, and 81.

[0072] Examples of inorganic pigments include barium sulfate, zinc oxide, lead sulfate, yellow lead, zinc yellow, red iron oxide (red iron (III) oxide), cadmium red, ultramarine, Prussian blue, chromium oxide green, cobalt green, amber, titanium black, synthetic iron black, titanium oxide, iron tetroxide, and other metal oxide powders, metal sulfide powders, or metal powders. Inorganic pigments are used in combination with organic pigments to ensure good coatability, sensitivity, developability, and the like while maintaining a balance between saturation and brightness.

[0073] The dispersion herein may contain a dye within a range that does not decrease the heat resistance.

[0074] <Solvent> The dispersion of the present invention may contain a solvent. The solvent may be, for example, 1,2,3-trichloropropane, 1,3-butanediol, 1,3-butylene glycol, 1,3-butylene glycol diacetate, 1,4-dioxane, 2-heptanone, 2-methyl-1,3-propanediol, 3,5,5-trimethyl-2-cyclohexen-1-one, 3,3,5-trimethylcyclohexanone, 3-ethoxyethylpropionate, 3-methyl-1,3-butanediol, 3-methoxy-3-methyl-1-butanol, 3-methoxy-3-methylbutyl acetate, 3-methoxybutanol, 3-methoxyethyl butylacetate ... Butyl acetate, 4-heptanone, m-xylene, m-diethylbenzene, m-dichlorobenzene, N,N-dimethylacetamide, N,N-dimethylformamide, n-butyl alcohol, n-butylbenzene, n-propyl acetate, N-methylpyrrolidone, o-xylene, o-chlorotoluene, o-diethylbenzene, o-dichlorobenzene, p-chlorotoluene, p-diethylbenzene, sec-butylbenzene, tert-butylbenzene, γ-butyrolactone, isobutyl alcohol, isophorone, ethylene glycol diethyl ether ethyl ether, ethylene glycol dibutyl ether, ethylene glycol monoisopropyl ether, ethylene glycol monoethyl ether, ethylene glycol monoethyl ether acetate, ethylene glycol monotertiary butyl ether, ethylene glycol monobutyl ether, ethylene glycol monobutyl ether acetate, ethylene glycol monopropyl ether, ethylene glycol monohexyl ether, ethylene glycol monomethyl ether, ethylene glycol monomethyl ether acetate, diisobutyl ketone, diethylene glycol diethyl ether, diethylene glycol dimethyl ether, diethylene glycol monoisopropyl ether, diethylene glycol monoethyl ether acetate, diethylene glycol monobutyl ether, diethylene glycol monobutyl ether acetate, diethylene glycol monomethyl ether, cyclohexanol, cyclohexanol acetate, cyclohexanone, dipropylene glycol dimethyl ether, dipropylene glycol methyl ether acetate, dipropylene glycol monoethyl ether,Examples of the solvent include dipropylene glycol monobutyl ether, dipropylene glycol monopropyl ether, dipropylene glycol monomethyl ether, diacetone alcohol, triacetin, tripropylene glycol monobutyl ether, tripropylene glycol monomethyl ether, propylene glycol diacetate, propylene glycol phenyl ether, propylene glycol monoethyl ether, propylene glycol monoethyl ether acetate, propylene glycol monobutyl ether, propylene glycol monopropyl ether, propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether propionate, benzyl alcohol, methyl isobutyl ketone, methylcyclohexanol, n-amyl acetate, n-butyl acetate, isoamyl acetate, isobutyl acetate, propyl acetate, and dibasic acid esters. The solvent can be used alone or in a mixture of two or more.

[0075] The dispersion of the present invention may contain, in addition to the acidic dispersant, colorant, and solvent, a binder resin, a polymerizable compound, a photopolymerization initiator, and the like.

[0076] <Binder resin> The binder resin is a resin that, when a coating film having a thickness of 2 μm is formed, has a transmittance of preferably 80% or more, more preferably 95% or more in the entire wavelength region of 400 to 700 nm in the visible light region. Examples of the resin include thermoplastic resins and photosensitive resins.

[0077] Examples of the thermoplastic resin include butyral resin, styrene-maleic acid copolymer, chlorinated polyethylene, chlorinated polypropylene, polyvinyl chloride, vinyl chloride-vinyl acetate copolymer, polyvinyl acetate, polyurethane resin, polyester resin, acrylic resin, alkyd resin, polystyrene, polyamide resin, rubber resin, cyclized rubber resin, cellulose, polyethylene, polybutadiene, and polyimide resin. Examples of the thermosetting resin include epoxy resin, benzoguanamine resin, rosin-modified maleic acid resin, rosin-modified fumaric acid resin, melamine resin, urea resin, and phenol resin.

[0078] The photosensitive resin is preferably a resin obtained by reacting a polymer having a reactive substituent such as a hydroxyl group, a carboxyl group, or an amino group with a (meth)acrylic compound having a reactive substituent such as an isocyanate group, an aldehyde group, or an epoxy group, or cinnamic acid to introduce a photocrosslinkable group such as a (meth)acryloyl group or a styryl group into the polymer. Also preferred is a resin obtained by half-esterifying a polymer containing an acid anhydride such as a styrene-maleic anhydride copolymer or an α-olefin-maleic anhydride copolymer with a (meth)acrylic compound having a hydroxyl group such as a hydroxyalkyl (meth)acrylate.

[0079] Considering pattern formation by photolithography, the binder resin is preferably an alkali-soluble resin. The alkali-soluble resin is a resin that dissolves in an alkaline aqueous solution, and is, for example, a resin having an acidic functional group such as a carboxyl group or a sulfonic group and a weight average molecular weight of 1,000 to 500,000, preferably 5,000 to 100,000. Examples of the alkali-soluble resin include acrylic resins having an acidic functional group, α-olefin / maleic acid (anhydride) copolymers, styrene / maleic acid (anhydride) copolymers, styrene / styrenesulfonic acid copolymers, ethylene / (meth)acrylic acid copolymers, isobutylene / maleic acid (anhydride) copolymers, etc. Among these, acrylic resins having an acidic functional group, α-olefin / maleic acid (anhydride) copolymers, styrene / maleic acid (anhydride) copolymers, and styrene / styrenesulfonic acid copolymers are preferred.

[0080] The content of the binder resin is preferably 20 to 400 parts by mass, more preferably 50 to 250 parts by mass, based on 100 parts by mass of the colorant. When an appropriate amount is contained, a coating can be easily formed and good color characteristics can be easily obtained.

[0081] <Polymerizable compound> The polymerizable compound is a monomer or oligomer having a polymerizable unsaturated group. The polymerizable unsaturated group may be a vinyl group, a (meth)acryloyl group, a (meth)allyl group, or the like. The number of polymerizable unsaturated groups in the polymerizable compound is 1 or more, and preferably 2 to 20.

[0082] Examples of the polymerizable compound include linear or branched alkyl (meth)acrylates such as methyl (meth)acrylate, ethyl (meth)acrylate, propyl (meth)acrylate, isopropyl (meth)acrylate, butyl (meth)acrylate, isobutyl (meth), tertiary butyl (meth)acrylate, isoamyl (meth)acrylate, octyl (meth)acrylate, isooctyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, cetyl (meth)acrylate, decyl (meth)acrylate, isodecyl (meth)acrylate, lauryl (meth)acrylate, tridecyl (meth)acrylate, isomyristyl (meth)acrylate, stearyl (meth)acrylate, or isostearyl (meth)acrylate; cyclic alkyl (meth)acrylates such as cyclohexyl (meth)acrylate, tertiary butyl cyclohexyl (meth)acrylate, dicyclopentanyl (meth)acrylate, dicyclopentanyloxyethyl (meth)acrylate, dicyclopentenyl (meth)acrylate, dicyclopentenyloxyethyl (meth)acrylate, or isobornyl (meth)acrylate; Fluoroalkyl (meth)acrylates such as trifluoroethyl (meth)acrylate, octafluoropentyl (meth)acrylate, perfluorooctylethyl (meth)acrylate, or tetrafluoropropyl (meth)acrylate; (Meth)acryloxy-modified polydimethylsiloxane (silicone macromer); (meth)acrylates having a heterocycle, such as tetrahydrofurfuryl (meth)acrylate or 3-methyl-3-oxetanyl (meth)acrylate; (meth)acrylates having an aromatic ring, such as benzyl (meth)acrylate, phenoxyethyl (meth)acrylate, phenoxypolyethylene glycol (meth)acrylate, paracumylphenoxyethyl (meth)acrylate, paracumylphenoxypolyethylene glycol (meth)acrylate, or nonylphenoxypolyethylene glycol (meth)acrylate; (poly)alkylene glycol monoalkyl ether (meth)acrylates such as 2-methoxyethyl (meth)acrylate, 2-ethoxyethyl (meth)acrylate, 3-methoxybutyl (meth)acrylate, 2-methoxypropyl (meth)acrylate, diethylene glycol monomethyl ether (meth)acrylate, diethylene glycol monoethyl ether (meth)acrylate, triethylene glycol monomethyl ether (meth)acrylate, triethylene glycol monoethyl ether (meth)acrylate, diethylene glycol mono-2-ethylhexyl ether (meth)acrylate, dipropylene glycol monomethyl ether (meth)acrylate, tripropylene glycol mono(meth)acrylate, polyethylene glycol monolauryl ether (meth)acrylate, or polyethylene glycol monostearyl ether (meth)acrylate; (meth)acrylates having a carboxyl group, such as (meth)acrylic acid, acrylic acid dimer, 2-(meth)acryloyloxyethyl phthalate, 2-(meth)acryloyloxypropyl phthalate, 2-(meth)acryloyloxyethyl hexahydrophthalate, 2-(meth)acryloyloxypropyl hexahydrophthalate, ethylene oxide-modified succinic acid (meth)acrylate, β-carboxyethyl (meth)acrylate, or ω-carboxypolycaprolactone (meth)acrylate; (meth)acrylates having a hydroxyl group, such as 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 2-hydroxybutyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate, 2-acryloyloxyethyl-2-hydroxyethyl (meth)phthalate, diethylene glycol mono(meth)acrylate, dipropylene glycol mono(meth)acrylate, polyethylene glycol mono(meth)acrylate, propylene glycol mono(meth)acrylate, polypropylene glycol mono(meth)acrylate, polytetramethylene glycol mono(meth)acrylate, poly(ethylene glycol-propylene glycol) mono(meth)acrylate, poly(ethylene glycol-tetramethylene glycol) mono(meth)acrylate, poly(propylene glycol-tetramethylene glycol) mono(meth)acrylate, or glycerol (meth)acrylate; Ethylene glycol di(meth)acrylate, diethylene glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, polyethylene glycol di(meth)acrylate, propylene glycol di(meth)acrylate, dipropylene glycol di(meth)acrylate, tripropylene glycol di(meth)acrylate, polypropylene glycol di(meth)acrylate, poly(ethylene glycol-propylene glycol) di(meth)acrylate, poly(ethylene glycol-tetramethyl (poly)alkylene glycol di(meth)acrylates such as poly(propylene glycol-tetramethylene glycol) di(meth)acrylate, polytetramethylene glycol di(meth)acrylate, 1,3-butanediol di(meth)acrylate, neopentyl glycol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, 1,9-nonanediol di(meth)acrylate, or 2-ethyl,2-butyl-propanediol di(meth)acrylate; di(meth)acrylates such as dimethylol dicyclopentane di(meth)acrylate, hydroxypivalic acid neopentyl glycol di(meth)acrylate, stearic acid modified pentaerythritol di(meth)acrylate, ethylene oxide modified bisphenol A di(meth)acrylate, propylene oxide modified bisphenol A di(meth)acrylate, tetramethylene oxide modified bisphenol A di(meth)acrylate, ethylene oxide modified bisphenol F di(meth)acrylate, propylene oxide modified bisphenol F di(meth)acrylate, tetramethylene oxide modified bisphenol F di(meth)acrylate, zinc diacrylate, ethylene oxide modified phosphate triacrylate, or glycerol di(meth)acrylate; (meth)acrylates having a tertiary amino group, such as dimethylaminoethyl (meth)acrylate, diethylaminoethyl (meth)acrylate, dimethylaminopropyl (meth)acrylate, or diethylaminopropyl (meth)acrylate; trifunctional or higher polyfunctional (meth)acrylates such as glycerol tri(meth)acrylate, trimethylolpropane tri(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol penta(meth)acrylate, and dipentaerythritol hexa(meth)acrylate; Glycerol triglycidyl ether-(meth)acrylic acid adduct, glycerol diglycidyl ether-(meth)acrylic acid adduct, polyglycerol polyglycidyl ether-(meth)acrylic acid adduct, 1,6-butanediol diglycidyl ether, alkyl glycidyl ether-(meth)acrylic acid adduct, allyl glycidyl ether-(meth)acrylic acid adduct, phenyl glycidyl ether-(meth)acrylic acid adduct, styrene oxide-(meth)acrylic acid adduct, bisphenol A diglycidyl ether-(meth)acrylic acid adduct, propylene oxide modified bisphenol A diglycidyl ether-(meth)acrylic acid adduct, bisphenol F diglycidyl ether-(meth)acrylic acid adduct ) acrylic acid adduct, epichlorohydrin-modified phthalic acid-(meth)acrylic acid adduct, epichlorohydrin-modified hexahydrophthalic acid-(meth)acrylic acid adduct, ethylene glycol diglycidyl ether-(meth)acrylic acid adduct, polyethylene glycol diglycidyl ether-(meth)acrylic acid adduct, propylene glycol diglycidyl ether-(meth)acrylic acid adduct, polypropylene glycol diglycidyl ether-(meth)acrylic acid adduct, phenol novolac type epoxy resin-(meth)acrylic acid adduct, cresol novolac type epoxy resin-(meth)acrylic acid adduct, or other epoxy resin-(meth)acrylic acid adducts, and other epoxy (meth)acrylates; (meth)acryloyl-modified resin oligomers such as (meth)acryloyl-modified isocyanurate, (meth)acryloyl-modified polyurethane, (meth)acryloyl-modified polyester, (meth)acryloyl-modified melamine, (meth)acryloyl-modified silicone, (meth)acryloyl-modified polybutadiene, or (meth)acryloyl-modified rosin; Vinyl such as styrene, α-methylstyrene, vinyl acetate, vinyl (meth)acrylate, or allyl (meth)acrylate; vinyl ethers such as hydroxyethyl vinyl ether, ethylene glycol divinyl ether, or pentaerythritol trivinyl ether; Examples of the monomer include amides such as (meth)acrylamide, N-hydroxymethyl(meth)acrylamide, and N-vinylformamide; and acrylonitrile. The polymerizable compounds may be used alone or in combination of two or more kinds.

[0083] The content of the polymerizable compound is preferably 2 to 50 parts by mass, and more preferably 2 to 30 parts by mass, based on 100 parts by mass of the colorant. When an appropriate amount is added, photocurability and developability are further improved.

[0084] <Photopolymerization initiator> Examples of the photopolymerization initiator include acetophenone-based photopolymerization initiators such as 4-phenoxydichloroacetophenone, 4-tert-butyl-dichloroacetophenone, diethoxyacetophenone, 1-(4-isopropylphenyl)-2-hydroxy-2-methylpropan-1-one, 1-hydroxycyclohexyl phenyl ketone, 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butan-1-one, and 2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one; Benzoin-based photopolymerization initiators such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, or benzil dimethyl ketal; Benzophenone-based photoinitiators such as benzophenone, benzoylbenzoic acid, methyl benzoylbenzoate, 4-phenylbenzophenone, hydroxybenzophenone, acrylated benzophenone, or 4-benzoyl-4'-methyldiphenyl sulfide; Thioxanthone-based photopolymerization initiators such as thioxanthone, 2-chlorothioxanthone, 2-methylthioxanthone, isopropylthioxanthone, and 2,4-diisopropylthioxanthone; triazine-based photopolymerization initiators such as 2,4,6-trichloro-s-triazine, 2-phenyl-4,6-bis(trichloromethyl)-s-triazine, 2-(p-methoxyphenyl)-4,6-bis(trichloromethyl)-s-triazine, 2-(p-tolyl)-4,6-bis(trichloromethyl)-s-triazine, 2-piperonyl-4,6-bis(trichloromethyl)-s-triazine, 2,4-bis(trichloromethyl)-6-styryl-s-triazine, 2-(naphth-1-yl)-4,6-bis(trichloromethyl)-s-triazine, 2-(4-methoxy-naphth-1-yl)-4,6-bis(trichloromethyl)-s-triazine, 2,4-trichloromethyl-(piperonyl)-6-triazine, or 2,4-trichloromethyl(4'-methoxystyryl)-6-triazine; Examples of the photopolymerization initiator include a borate-based photopolymerization initiator, a carbazole-based photopolymerization initiator, an imidazole-based photopolymerization initiator, etc. The photopolymerization initiator may be used alone or in combination of two or more kinds.

[0085] The content of the photopolymerization initiator is preferably from 5 to 200 parts by mass, and more preferably from 10 to 150 parts by mass, relative to 100 parts by mass of the pigment.

[0086] The dispersion of the present invention can use a sensitizer together with the photopolymerization initiator. This improves the photoreactivity. Examples of the sensitizer include α-acyloxyester, acylphosphine oxide, methylphenyl glyoxylate, benzyl, 9,10-phenanthrenequinone, camphorquinone, ethyl anthraquinone, 4,4'-diethylisophthalophenone, 3,3',4,4'-tetra(tert-butylperoxycarbonyl)benzophenone, and 4,4'-diethylaminobenzophenone.

[0087] The content of the sensitizer is preferably 0.1 to 60 parts by mass with respect to 100 parts by mass of the photopolymerization initiator.

[0088] The dispersion of the present invention is prepared by dispersing a pigment, an acidic dispersant, a solvent, and the like. When the pigment is an organic pigment, the organic pigment can be dispersed more finely by using a dispersing aid such as a dye derivative during the dispersion process. When the pigment has high solubility in the solvent, the dispersion process may not be necessary. When two or more types of pigments are used in combination, a dispersion can be prepared for each pigment and then mixed. A dispersion can also be prepared by using a plurality of pigments at once. Next, a polymerizable compound, a photopolymerization initiator, and the like are further mixed and mixed to obtain a photosensitive dispersion. It goes without saying that the timing of mixing each material is arbitrary.

[0089] The dispersion treatment can be carried out using a dispersion device such as a kneader, a two-roll mill, a three-roll mill, a ball mill, a horizontal sand mill, a vertical sand mill, an annular bead mill, or an attritor.

[0090] After preparation of the dispersion, it is preferable to remove coarse particles of 5 μm or more, preferably coarse particles of 1 μm or more, more preferably coarse particles of 0.5 μm or more, and mixed dust by means of centrifugation, a sintered filter, a membrane filter or the like.

[0091] <Other dispersants> In the present specification, in addition to the acidic dispersant, other dispersants can be used in combination. Examples of the other dispersants include resin-type dispersants other than the acidic dispersant of the present invention, surfactants, etc.

[0092] Examples of resin-type dispersants other than the acidic dispersant of the present invention include anionic resin-type pigment dispersants such as styrene-maleic anhydride copolymers, olefin-maleic anhydride copolymers, poly(meth)acrylates, styrene-(meth)acrylic acid copolymers, (meth)acrylic acid-(meth)acrylic acid alkyl ester copolymers, (meth)acrylic acid-polyvinyl macromer copolymers, phosphate group-containing acrylic resins, aromatic carboxyl group-containing acrylic resins, polystyrene sulfonates, acrylamide-(meth)acrylic acid copolymers, carboxymethyl cellulose, polyurethanes having carboxyl groups, formalin condensates of naphthalene sulfonates, and sodium alginate; nonionic resin-based pigment dispersants such as polyvinyl alcohol, polyalkylene polyamines, polyacrylamides, or polymeric starches; or Examples of the pigment dispersant include polyethyleneimine, aminoalkyl(meth)acrylate copolymers, polyvinylimidazoline, polyurethanes having amino groups, reaction products of poly(lower alkyleneimine)s with polyesters having free carboxyl groups, and cationic resin-type pigment dispersants such as Satokinsan.

[0093] Commercially available resin-type dispersants include Disperbyk-101, 103, 107, 108, 110, 111, 116, 130, 140, 154, 161, 162, 163, 164, 165, 166, 170, 171, 174, 180, 181, 182, 183, 184, 185, 190, 2000, 2001, 2020, 2025, 2050, 2070, 2095, 2150, and 2155 manufactured by BYK Japan Co., Ltd. Anti-Terra-U, 203, 204, BYK-P104, P104S, 220S, 6919, Lactimon, Lactimon-WS, Bykumen, etc. SOLSPERSE-3000, 9000, 13000, 13240, 13650, 13940, 16000, 17000, 18000, 20000, 21000, 24000, 26000, 27000, 28000, 31845, 32000, 32500, 32550, 33500, 32600, 34750, 35100, 36600, 38500, 41000, 41090, 53095, 55000, 76500, etc., EFKA-46, 47, 48, 452, 4008, 4009, 4010, 4015, 4020, 4047, 4050, 4055, 4060, 4080, 4400, 4401, 44 02, 4403, 4406, 4408, 4300, 4310, 4320, 4330, 4340, 450, 451, 453, 4540, 4550, 4560, 4800, 5010, 5065, 5066, 5070, 7500, 7554, 1101, 120, 150, 1501, 1502, 1503, etc., and Ajisper PA111, PB711, PB821, PB822, PB824, etc. manufactured by Ajinomoto Fine-Techno Co., Ltd.

[0094] The surfactant may be an anionic surfactant such as polyoxyethylene alkyl ether sulfate, sodium dodecylbenzene sulfonate, alkali salt of styrene-acrylic acid copolymer, sodium alkyl naphthalene sulfonate, sodium alkyl diphenyl ether disulfonate, monoethanolamine lauryl sulfate, triethanolamine lauryl sulfate, ammonium lauryl sulfate, monoethanolamine stearate, sodium stearate, sodium lauryl sulfate, monoethanolamine of styrene-acrylic acid copolymer, or polyoxyethylene alkyl ether phosphate; nonionic surfactants such as polyoxyethylene oleyl ether, polyoxyethylene lauryl ether, polyoxyethylene nonylphenyl ether, polyoxyethylene alkyl ether phosphate ester, polyoxyethylene sorbitan monostearate, or polyethylene glycol monolaurate; cationic surfactants such as alkyl quaternary ammonium salts and their ethylene oxide adducts; or Examples of the dispersing agent include alkyl betaines such as alkyl dimethyl amino acetic acid betaines, and amphoteric surfactants such as alkyl imidazolines. The dispersing agents can be used alone or in combination of two or more kinds.

[0095] The amount of the other dispersant used is preferably 0.1 to 40 parts by mass, and more preferably 0.1 to 30 parts by mass, based on 100 parts by mass of the pigment. Using an appropriate amount of the other dispersant further improves dispersibility.

[0096] <Dye derivatives> A dye derivative can be used in the dispersion as necessary. This further improves the dispersibility of the pigment. The dye derivative is a compound having an acidic group, a basic group, a neutral group, or the like in the organic dye residue. Examples of the dye derivative include compounds having an acidic substituent such as a sulfo group, a carboxy group, or a phosphoric acid group (hereinafter referred to as an acidic derivative), as well as amine salts thereof, sulfonamide groups, or compounds having basic substituents such as a tertiary amino group at the terminal (hereinafter referred to as a basic derivative), and compounds having a neutral substituent such as a phenyl group or a phthalimidoalkyl group. Examples of organic dyes include diketopyrrolopyrrole pigments, anthraquinone pigments, quinacridone pigments, dioxazine pigments, perinone pigments, perylene pigments, thiazineindigo pigments, triazine pigments, benzimidazolone pigments, indole pigments such as benzoisoindole, isoindoline pigments, isoindolinone pigments, quinophthalone pigments, naphthol pigments, threne pigments, metal complex pigments, azo pigments such as azo, disazo, polyazo, etc. Among these, basic derivatives are preferred.

[0097] In the dispersion of the present invention, the amount of the dye derivative is preferably 1 to 50 parts by mass, more preferably 3 to 30 parts by mass, and even more preferably 5 to 25 parts by mass, relative to 100 parts by mass of the pigment. When the amount of the dye derivative is 1% by mass or more, the effect of adding the dye derivative is obtained and the pigment dispersibility is improved, and when the amount is 50% by mass or less, adverse effects on heat resistance and light resistance are unlikely to appear.

[0098] Specific examples of the dye derivative having a basic group that can be used in the present invention are shown below, but are not limited to these.

[0099] Dye derivative 1 [ka]

[0100] Dye derivative 2 [ka]

[0101] Dye derivative 3 [ka]

[0102] Dye derivative 4 [ka]

[0103] Dye derivative 5 [ka]

[0104] <Color filters> The color filter preferably has filter segments formed from the above dispersion on a base material (also called a substrate). The color filter preferably has a red filter segment, a green filter segment, and a blue filter segment by appropriately selecting the type of colorant used. The color filter may have a magenta filter segment, a cyan filter segment, and a yellow filter segment instead of or in addition to the color filter segments. The substrate may be a transparent substrate or a reflective substrate. The transparent substrate may be, for example, a glass substrate. The reflective substrate may be, for example, a substrate using an aluminum electrode or a metal thin film as a reflective surface.

[0105] It is preferable to form a color filter by first forming a black matrix on a substrate and then forming filter segments. It is also possible to form a thin film transistor (TFT) on the substrate before forming the black matrix. Examples of the black matrix include a multilayer film of chromium or chromium / chromium oxide, an inorganic film such as titanium nitride, and a resin film in which a light-shielding agent is dispersed.

[0106] The filter segments can be formed by, for example, a printing method, an electrodeposition method, a transfer method, an inkjet method, a photolithography method, etc. In this specification, the most preferred method is the photolithography method.

[0107] Examples of the substrate include a glass plate having a high transmittance to visible light, and a resin plate such as polycarbonate, polymethyl methacrylate, or polyethylene terephthalate.

[0108] In the photolithography method, for example, a coloring composition having a colorant of a certain color tone is applied onto a transparent substrate so that the dry film thickness is about 0.2 to 5 μm to form a coating. The obtained coating (hereinafter referred to as the first coating) is exposed (irradiated with light) through a mask having a predetermined pattern. Then, the coating is developed by immersing in a solvent or an alkaline developer or spraying the developer with a spray or the like, and the uncured parts are removed to obtain a desired pattern. This process can be similarly carried out using a photosensitive coloring composition having a colorant of another color tone to produce a color filter having filter segments of each color. In addition, a second coating (oxygen barrier film) can be formed on the first coating before exposure using polyvinyl alcohol or a water-soluble acrylic resin. This prevents the first coating from coming into contact with oxygen, thereby further improving the exposure sensitivity. In addition, the color filter can be heated (post-baked) to cure the uncured polymerizable compound in the filter segment.

[0109] Examples of the coating device include a spray coater, a spin coater, a slit coater, and a roll coater. A drying step can be carried out during coating. Examples of the drying device include a hot air oven and an infrared heater.

[0110] The developer may be an alkaline developer, for example, an inorganic alkali such as sodium carbonate or sodium hydroxide, or an organic alkali such as dimethylbenzylamine or triethanolamine. A defoaming agent or a surfactant may be added to the developer.

[0111] The post-bake temperature is preferably about 80 to 230° C. In recent years, in order to address environmental issues, low-temperature curing at 150° C. or less is more preferred. The low-temperature curing post-bake time is about 30 minutes to 1 hour.

[0112] The color filters obtained from the dispersions of the present invention can be used to manufacture image display devices. To manufacture an image display device, a liquid crystal display device, which is a type of image display device, is obtained by laminating the opposing substrate with a sealant, injecting liquid crystal through an injection port provided in the seal, sealing the injection port, and laminating a polarizing film or a retardation film on the outside of the substrate as necessary. This liquid crystal display device can be used in liquid crystal display modes that use color filters such as twisted nematic (TN), super twisted nematic (STN), in-plane switching (IPS), vertically aligned (VA), and optically convencive bend (OCB).

[0113] The image display device can be used for applications such as organic EL display devices, quantum dot display devices, electronic paper, and head-mounted displays in addition to liquid crystal display devices.

[0114] <Molded body> The molded article of the present invention is a melt-kneaded mixture of an acidic dispersant, a dispersed substance, and a resin. The dispersed substance may be a colorant, metal particles, etc. The resin is preferably a thermoplastic resin.

[0115] The content of the acidic dispersant is preferably 0.01 to 1 mass %, more preferably 0.05 to 1 mass %, and even more preferably 0.1 to 0.8 mass %, relative to 100 parts by mass of the dispersed material. When an appropriate amount is used, dispersibility is further improved, and compatibility with the resin is further improved.

[0116] <Coloring agent> Among the dispersed materials, the colorant may be the inorganic pigment described below in addition to the organic pigments already described.

[0117] Examples of inorganic pigments include white inorganic pigments such as zinc oxide, barium sulfate, titanium oxide, zinc sulfide, calcium carbonate, etc., yellow inorganic pigments such as chrome yellow, nickel titanium yellow, bismuth yellow, etc., red inorganic pigments such as iron oxide, blue inorganic pigments such as cobalt blue, ultramarine, etc., green inorganic pigments such as cobalt green, brown inorganic pigments such as chrome titanium yellow, black inorganic pigments such as carbon black, black iron oxide, pearl pigments, etc. Among these, barium sulfate, zinc sulfide, calcium carbonate, nickel titanium yellow, bismuth yellow, iron oxide, ultramarine, and pearl pigments are preferred in terms of not reducing the impact strength of the molded product.

[0118] The average particle size of the inorganic pigment is preferably 0.05 to 200 μm, more preferably 0.2 to 100 μm, and even more preferably 0.3 to 100 μm. A suitable average particle size can achieve high compatibility between dispersibility and surface smoothness of the molded product. The average particle size can be measured using a dynamic light scattering particle size distribution measuring device. For example, a particle size distribution measuring device ("UPA-EX150" manufactured by Nikkiso Co., Ltd.) can be used.

[0119] The content of the colorant in the dispersed materials is preferably 0.01 to 1 mass %, and more preferably 0.3 to 0.8 mass %, in the molded product.

[0120] <Thermoplastic resin> Examples of the thermoplastic resin include polyolefins such as polyethylene and polypropylene, polycarbonate, polyacrylics such as polymethyl (meth)acrylate, polyesters, cycloolefin resins, polystyrene, polyphenylene ether, acrylonitrile-butadiene-styrene copolymers (ABS resins), polyamides, polyacetals, polycarbonates, polyvinyl chloride, polyvinylidene chloride, and polyetherimides. Among these, polyolefins, polycarbonates, polyacrylics, polyesters, and cycloolefin resins are preferred because they provide good moldability and mechanical strength of the molded product. In addition, the thermoplastic resin preferably has a number average molecular weight of 30,000 or more from the viewpoint of mechanical strength and moldability of the molded product.

[0121] The melting point of the thermoplastic resin is preferably from 120 to 330°C, and more preferably from 150 to 300°C.

[0122] The molded article of the present invention may contain wax, antioxidant, light stabilizer, etc., as required, in addition to the acidic dispersant, colorant, and thermoplastic resin.

[0123] <Wax> The molded article of the present invention may contain a wax, which makes it easier to adjust the flowability during molding and improves processability. The waxes include natural waxes and synthetic waxes. Examples of natural waxes include vegetable waxes such as carnauba wax, rice wax, and Japan wax; animal waxes such as beeswax, lanolin, and spermaceti; mineral waxes such as montan wax, ozokerite, and ceresin; and petroleum waxes such as paraffin wax, microcrystalline wax, and petrolatum. Synthetic waxes include semi-synthetic waxes and fully synthetic waxes. Semi-synthetic waxes are natural waxes or natural wax-like materials that have been modified by chemical treatments such as esterification, amidation, and neutralization with an acidic wax. Examples of synthetic waxes include polyethylene-based waxes, polypropylene-based waxes, and polystyrene-based waxes.

[0124] Among these, the wax is preferably a low molecular weight (number average molecular weight less than 30,000) polyolefin. The wax is a polymer of an olefin monomer such as ethylene, propylene, or butylene, and may be a block or random copolymer or terpolymer. Specifically, it is a polymer of α-olefins such as low density polyethylene (LDPE), high density polyethylene (HDPE), or polypropylene (PP). These may be used alone or in combination of two or more kinds.

[0125] The number average molecular weight of the wax is preferably 1,000 to 30,000, and more preferably 2,000 to 25,000. Within this range, the wax migrates appropriately to the surface of the molded article, resulting in an excellent balance between sliding properties and bleed-out suppression.

[0126] The melting point of the wax is preferably 60 to 150° C., more preferably 70 to 140° C. Within this range, the processability when the thermoplastic resin and the wax are melt-kneaded is good.

[0127] The melt flow rate (MFR) of the wax determined in accordance with JIS K-7210 is preferably greater than 100 g / 10 min.

[0128] The blending amount of the wax is preferably 0.1 to 10 parts by mass with respect to 100 parts by mass of the thermoplastic resin contained in the molded article.

[0129] The molded article of the present invention can be produced in the composition ratio of the molded article, or can be produced using a colored resin composition, via a masterbatch containing a high concentration of a dispersed substance (e.g., a colorant), and then further diluted with a thermoplastic resin.

[0130] The melt kneading may be performed, for example, using a single screw kneading extruder, a twin screw kneading extruder, a tandem type twin screw kneading extruder, etc. The melt kneading temperature varies depending on the type of polyolefin, but is usually about 150 to 250°C.

[0131] The molding temperature is usually 160 to 280° C. depending on the softening point of the diluent resin. Before melt kneading, a composition containing an acidic dispersant, a dispersed substance, and a resin is processed into a master batch, and then the master batch and the resin are melt kneaded to produce a molded body. This allows the dispersed substance to be more finely dispersed. A master batch is a composition in which a dispersed substance such as a colorant is blended at a high concentration. For example, the master batch is preferably prepared by melt-kneading a thermoplastic resin, an acidic dispersant, and a colorant, and then molding the mixture into an arbitrary shape. Next, the master batch and a diluting resin (for example, the thermoplastic resin used in the master batch) are melt-kneaded to mold a molded body of a desired shape. Examples of the shape of the master batch include pellets, powder, and plates. The thermoplastic resin used to prepare the master batch is preferably the same thermoplastic resin as the diluting resin, but other thermoplastic resins may be used as long as there is no problem with compatibility.

[0132] Examples of the molding method include extrusion molding, injection molding, blow molding, etc. Examples of the extrusion molding method include compression molding, pipe extrusion molding, laminate molding, T-die molding, inflation molding, melt spinning, etc.

[0133] The molded article of the present invention can be used in a wide range of applications, such as containers for medical drugs, cosmetics, and foods, packaging materials, miscellaneous goods, textile products, containers for pharmaceuticals, various industrial coating materials, automobile parts, home appliances, building materials for houses, toiletries, etc. The molded article includes molded articles molded using a mold and molded articles molded without using a mold, such as plastic films. EXAMPLES

[0134] The present invention will be described below based on examples. However, the present invention is not limited to the examples. In addition, "parts" means "parts by mass" and "%" means "% by mass".

[0135] (Polymerization average molecular weight (Mw)) Weight average molecular weight (Mw) was measured by gel permeation chromatography (GPC) equipped with an RI detector. The instrument used was an HLC-8320GPC (manufactured by Tosoh Corporation), with two separation columns connected in series, and both packings were "TSK-GEL SUPER HZM-N" connected in series. The oven temperature was 40°C, THF solution was used as the eluent, and the flow rate was 0.35 ml / min. The sample was dissolved in a solvent consisting of 0.1 wt% of the above eluent, and 20 microliters were injected. All molecular weights are polystyrene equivalent values.

[0136] (Acid value) 40 ml of pyridine and 5 ml of water were added to 0.5 to 1.0 parts of the sample, and the mixture was stirred to dissolve uniformly. The acid value was measured by titrating the sample with an automatic titrator ("COM-555" manufactured by Hiranuma Sangyo Co., Ltd.) using a 0.1 mol / L potassium hydroxide-ethanol aqueous solution as the titrant. The acid value per unit of non-volatile content of the measured sample was calculated from the calculated acid value and the concentration of non-volatile content of the sample.

[0137] The acid value (mgKOH / g) of the dry sample was calculated using the following formula: Acid value (mgKOH / g) = {(5.611 × α × F) / S} / (non-volatile matter concentration / 100) Where S is the amount of sample taken (g) α: Consumption of 0.1 mol / L potassium hydroxide ethanol solution (ml) F: Potency of 0.1 mol / L potassium hydroxide in ethanol

[0138] (Reaction rate of acid dianhydride groups) 30 ml of a mixed solution of 1,4-dioxane and water (10:1) was added to 0.5 to 1.0 g of sample, and the mixture was stirred to dissolve uniformly. Then, 10 ml of the hexylamine adjustment solution described below was added, and the mixture was stirred for 5 minutes to obtain a measurement sample solution. Next, a 0.02 mol / L perchloric acid (1,4-dioxane) solution was used as the titrant, and titration was performed using an automatic titrator ("COM-555" manufactured by Hiranuma Sangyo Co., Ltd.) to determine the titration amount (B ml). Similarly, only 10 ml of the hexylamine adjustment solution was titrated to determine the blank titration amount (C ml). Then, the reaction rate of the acid dianhydride group of the resin was calculated using the following formula. Hexylamine adjustment solution: A mixture of 0.79g of hexylamine and 400g of 1,4-dioxane S: Amount of sample collected (g) A: Amount of amine compound contained in sample (mmol / g) = Amount of amine in resin solids (%) / Molecular weight of amine Measured resin dianhydride value (mmol / g) = {(blank titration C x 0.02) - (sample titration B x 0.02 - S x non-volatile content x A)} / (S x non-volatile content) Charged acid dianhydride value (mmol / g) = Charged acid dianhydride amount in acidic dispersant (wt%) / Molecular weight of acid dianhydride × Number of acid dianhydride groups in acid dianhydride Reaction rate of acid dianhydride group (mol%) = {1-(actual acid dianhydride value / charged acid dianhydride value)} x 100

[0139] (Non-volatile content) The non-volatile content was calculated from the weight ratio before and after drying in an electric oven at 170°C for 10 minutes by weighing 1.0 g of the sample into an aluminum container. Non-volatile content % = (weight of sample after drying) / (weight of sample before drying) x 100

[0140] <Example 1> (Production of Acid Dispersant 1) In a reaction vessel equipped with a gas inlet tube, a thermometer, a condenser, and a stirrer, 11.2 parts of benzyl alcohol, 88.8 parts of ε-caprolactone, and 0.1 parts of monobutyltin oxide as a catalyst were charged, and after replacing with nitrogen gas, the mixture was heated and stirred at 120°C for 4 hours. It was confirmed by measuring the non-volatile content that 98% or more had reacted, and a cyclic ester polymer was obtained.

[0141] Next, the reaction product was cooled to 40°C, and 50.0 parts of tert-butyl acrylate, 45.0 parts of methyl methacrylate, 5.0 parts of methacrylic acid, and 7.1 parts of 3-mercapto-1,2-propanediol (1-thioglycerol) were added and thoroughly stirred. Furthermore, 0.12 g of dimethyl 2,2'-azobis(2-methylpropionate) was added as an initiator, and the mixture was heated to 85°C and reacted for 7 hours. It was confirmed that the non-volatile content reached 95% or more, and a vinyl polymer was obtained (although it was a mixture with a cyclic ester polymer).

[0142] Next, 19.2 parts of pyromellitic dianhydride were added to the reaction product while keeping the internal temperature at 85°C, and the temperature was raised to 100°C while stirring. Then, 0.13 parts of N,N-dimethylbenzylamine were added, and the mixture was reacted at 120°C for 3 hours, and then at 100°C for 2 hours. It was confirmed that 95% or more of the acid anhydride was half-esterified by measuring the reaction rate of the acid dianhydride group, and an acidic dispersant 1 (dispersant 1) was obtained. The obtained dispersant was a resin that became a waxy solid at room temperature (25°C) and had fluidity at 80°C. The weight average molecular weight was 4,900, and the acid value was 68 mgKOH / g.

[0143] (Manufacture of acidic dispersants 2-9, 11-16, and 18) Acidic Dispersants 2 to 9, 11 to 16, and 18 were obtained by synthesizing in the same manner as in Production Example of Acidic Dispersant 1, except that the raw materials and the amounts charged were shown in Tables 1 and 2.

[0144] (Acidic Dispersant 10) In a reaction vessel equipped with a gas inlet tube, a thermometer, a condenser, and a stirrer, 17.9 parts of 1-dodecanol, 82.1 parts of ε-caprolactone, and 0.1 parts of monobutyltin oxide as a catalyst were charged, and after replacing with nitrogen gas, the mixture was heated and stirred at 120°C for 4 hours. It was confirmed by measuring the nonvolatile content that 98% had reacted, and a cyclic ester polymer was obtained.

[0145] Next, the reaction product was cooled to 40°C, and 50.0 parts of tert-butyl acrylate, 15.0 parts of methyl methacrylate, 5.0 parts of methacrylic acid, 30.0 parts of methyl methacrylate (3-ethyloxetan-3-yl), and 7.1 parts of 3-mercapto-1,2-propanediol (1-thioglycerol) were added and thoroughly stirred. Furthermore, 0.12 g of dimethyl 2,2'-azobis(2-methylpropionate) was added as an initiator, and the mixture was heated to 85°C and reacted for 7 hours. It was confirmed that the non-volatile content reached 95% or more, and a vinyl polymer was obtained (although it was a mixture with a cyclic ester polymer).

[0146] Next, 18.6 parts of pyromellitic dianhydride was added to the reaction product while keeping the internal temperature at 85°C, and the mixture was thoroughly stirred. Then, 0.13 parts of N,N-dimethylbenzylamine was added, and the mixture was reacted at 100°C for 6 hours. Measurement of the reaction rate of the acid dianhydride group confirmed that 95% or more of the acid anhydride was half-esterified, and acidic dispersant 10 (dispersant 10) was obtained. The obtained dispersant was a thermoplastic resin that became a waxy solid at room temperature and had fluidity at 80°C. The weight average molecular weight was 5,000, and the acid value was 67 mgKOH / g.

[0147] (Production Example of Acid Dispersant 17) A mixture of cyclic ester polymer and vinyl polymer was obtained by the same procedure as in the manufacturing example of acidic dispersant 1. Next, 30.8 parts of pyromellitic dianhydride was added to the above reaction product while keeping the internal temperature at 85 ° C., and the temperature was raised to 100 ° C. while stirring. Then, 0.13 parts of N,N-dimethylbenzylamine was added and reacted at 120 ° C. for 3 hours, and then, by measuring the reaction rate of the acid anhydride group, it was confirmed that 75% had reacted. Next, 20.6 g of 3-methoxybutanol as a terminal blocking material (the amount used was such that the amount of blocking material charged was 70 mol% relative to the remaining acid anhydride group of 100 mol%) was added and reacted at 120 ° C. for 3 hours. It was confirmed that 97% or more had reacted by measuring the reaction rate of the acid anhydride group, and the reaction was terminated. The resulting dispersant was a resin that was a waxy solid at room temperature and had fluidity at 80° C. The weight average molecular weight was 4,700 and the acid value was 100 mgKOH / g.

[0148] (Production Example of Dispersant 19, Comparative Example 1) In a reaction vessel equipped with a gas inlet tube, a thermometer, a condenser, and a stirrer, 11.2 parts of benzyl alcohol, 88.8 parts of ε-caprolactone, and 0.1 parts of monobutyltin oxide as a catalyst were charged, and after replacing with nitrogen gas, the mixture was heated and stirred at 120°C for 4 hours. It was confirmed by measuring the non-volatile content that 98% had reacted, and a cyclic ester polymer was obtained.

[0149] Next, 11.3 parts of pyromellitic dianhydride were added to the reaction product while keeping the internal temperature at 85°C, and the temperature was raised to 100°C while stirring. Then, 0.13 parts of N,N-dimethylbenzylamine were added, and the mixture was reacted at 120°C for 3 hours, and then at 100°C for 2 hours. The reaction rate of the acid anhydride group was measured to confirm that 95% or more of the acid anhydride was half-esterified, and acidic dispersant 19 (dispersant 19) was obtained. The obtained dispersant was a thermoplastic resin that became a waxy solid at room temperature and had fluidity at 80°C. The weight average molecular weight was 3,500, and the acid value was 62 mgKOH / g.

[0150] (Production Example of Dispersant 20, Comparative Example 2) In a reaction vessel equipped with a gas inlet tube, a thermometer, a condenser, and a stirrer, 50.0 parts of tert-butyl acrylate, 45.0 parts of methyl methacrylate, 5.0 parts of methacrylic acid, 7.1 parts of 3-mercapto-1,2-propanediol (1-thioglycerol), and 70.0 parts of propylene glycol monomethyl ether acetate (hereinafter referred to as PGMAc) were charged and thoroughly stirred. Furthermore, 0.12 g of dimethyl 2,2'-azobis (2-methylpropionate) was charged as an initiator, and the temperature was raised to 85°C and reacted for 7 hours to synthesize a vinyl polymer. It was confirmed that 95% or more had reacted by measuring the non-volatile content. Next, 10.8 parts of pyromellitic dianhydride (manufactured by Daicel Chemical Industries, Ltd.), 35.2 parts of PGMAc, and 0.13 parts of N,N-dimethylbenzylamine were added and reacted at 120°C for 3 hours, and then at 100°C for 2 hours. The reaction rate of the acid anhydride group was measured to confirm that 97% or more had reacted, and the reaction was terminated. After the reaction was completed, the resin solution was taken out and the PGMAc was removed using a vacuum dryer, resulting in a dispersant 20 with a weight average molecular weight of 4,000 and an acid value of 82 mgKOH / g. Separately, we attempted to synthesize Dispersant 20 without using PGMAc, but the synthesis failed due to problems in controlling the reaction heat and an increase in viscosity during polymerization.

[0151] (Productivity) The productivity of the obtained acidic dispersants was evaluated as follows. When the dispersants were produced without using a solvent, the controllability of reaction heat and the increase in viscosity during polymerization were comparatively evaluated. The evaluation of dispersants 1 to 19 was based on dispersant 20, which has poor productivity. ○: Compared to Dispersant 20, the reaction heat is easier to control, and the melt viscosity when heated to 80°C is significantly lower (productivity is very good). △: Compared to Dispersant 20, it is slightly easier to control the reaction heat, and the melt viscosity when heated to 80°C is low (productivity is in the practical range). ×: Compared to Dispersant 20, the reaction heat control is equivalent, and the melt viscosity when heated to 80°C is also equivalent or higher (productivity is not stable).

[0152] [Table 1]

[0153] [Table 2]

[0154] The abbreviations in the table are as follows. [Monoalcohol] BzA: Benzyl alcohol DGME: Carbitol (diethylene glycol monoethyl ether) ·DA: 1-dodecanol [Cyclic ester] ·ε-CL: ε-caprolactone δ-VL: δ-valerolactone · M-LA: meso-lactide [Vinyl Monomer] t-BA: tert-butyl acrylate MMA: Methyl methacrylate ·EA: Ethyl acrylate ·MAA: Methacrylic acid · 2-MTA: Methoxyethyl acrylate OXMA: (3-ethyloxetan-3-yl)methyl methacrylate

[0155] [Chain transfer agent] 1-TG: 1-thioglycerol [Acid dianhydride] PMA: Pyromellitic dianhydride BPDA: 3,3′,4,4′-biphenyltetracarboxylic dianhydride BTA: 1,2,3,4-butanetetracarboxylic dianhydride

[0156] <Production method of binder resin> (Preparation of acrylic resin solution 1) A separable 4-neck flask was fitted with a thermometer, a cooling tube, a nitrogen gas inlet tube, and a stirrer. 70.0 parts of propylene glycol monomethyl ether acetate was charged into the reaction vessel, which was then heated to 80°C and replaced with nitrogen in the reaction vessel. A mixture of 13.3 parts of n-butyl methacrylate, 4.6 parts of 2-hydroxyethyl methacrylate, 4.3 parts of methacrylic acid, 7.4 parts of paracumylphenol ethylene oxide modified acrylate (Toagosei Co., Ltd.'s "Aronix M110"), and 0.4 parts of 2,2'-azobisisobutyronitrile was added dropwise over 2 hours from the dropping tube. After the dropwise addition was completed, the reaction was continued for another 3 hours to obtain a solution of an acrylic resin with a weight average molecular weight (Mw) of 26,000. After cooling to room temperature, approximately 2 g of the resin solution was sampled and dried by heating at 180°C for 20 minutes to measure the non-volatile content. Propylene glycol monoethyl ether acetate was added so that the non-volatile content became 20 mass %, thereby preparing acrylic resin solution 1.

[0157] <Method of manufacturing pigment dispersion> (Production of Pigment Dispersion 1, Example 19-1) The mixture below was stirred and mixed until homogenous, and then dispersed in an Eiger mill (Mini Model M-250MKII, manufactured by Eiger Japan) using zirconia beads with a diameter of 0.5 mm for 3 hours. The mixture was then filtered through a filter with a pore size of 5.0 μm to produce Pigment Dispersion 1 with a non-volatile content of 20% by mass. PR254 (CI Pigment Red 254 "Irgaphor Red B-CF" manufactured by BASF Japan): 15.2 parts Dye derivative 1:0.8 parts Acidic dispersant 1 (dispersant 1): 4.0 parts Propylene glycol monomethyl ether acetate (PGMAc): 80.0 parts

[0158] (Production of Pigment Dispersions 2 to 24, Examples 20-1 to 40-1, and Comparative Examples 3-1 to 4-1) Pigment Dispersions 2 to 24 were obtained in the same manner as in Example 1 of Pigment Dispersion 1, except that the raw materials and amounts charged were used as shown in Table 3.

[0159] Dye derivative 1: [ka]

[0160] Dye derivative 2: [ka]

[0161] Dye derivative 3: [ka]

[0162] [Table 3]

[0163] [Example 19-2] (Coloring composition 1) The mixture having the following composition was stirred and mixed to be homogeneous, and then filtered through a filter having a pore size of 1 μm to prepare colored composition 1 having a nonvolatile content of 15%. Pigment dispersion 1:50.0 parts Acrylic resin solution 1:7.5 parts Polymerizable compound ("Aronix M-402" manufactured by Toagosei Co., Ltd.): 2.0 parts Photopolymerization initiator (BASF Japan "Irgacure OXE02": 1.2 parts Sensitizer (Hodogaya Chemical Co., Ltd. "EAB-F"): 0.3 parts Propylene glycol monomethyl ether acetate (PGMAc): 39.0 parts

[0164] [Polymerizable compound] M-402: Aronix M-402: A mixture of dipentaerythritol pentaacrylate and dipentaerythritol hexaacrylate (manufactured by Toagosei Co., Ltd.)

[0165] [Photopolymerization initiator] Irgacure OXE02: Ethan-1-one, 1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl], 1-(O-acetyloxime) (BASF Japan)

[0166] [Sensitizer] EAB-F: 4,4'-bis(diethylamino)benzophenone (manufactured by Hodogaya Chemical Co., Ltd.)

[0167] [Examples 20-2 to 40-2, Comparative Examples 3-2 to 4-2] (Production Examples of Coloring Compositions 2 to 24) Colored compositions 2 to 24 were obtained in the same manner as in the production example of colored composition 1, except that the pigment dispersions shown in Table 4 were used instead of the pigment dispersion 1 of Example 19-2.

[0168] (Heat resistance) The heat resistance of the obtained acidic dispersants was evaluated as follows. Using a differential thermal and thermogravimetric simultaneous analyzer (TG-DTA8122 type manufactured by Rigaku Corporation), the temperature was raised from 40°C to 500°C at a heating rate of 10°C / min in air to measure the TG-DTA curve. The temperature at which the measured sample loses 50% weight was taken as Td50 and compared. The higher the Td50 temperature, the better the heat resistance is, and the more the acidic dispersant can be suppressed from decomposing or volatilizing in a high-temperature heated state in the dispersion or molded body. The evaluation of dispersants 1 to 18 and dispersant 20 was based on dispersant 19, which has low heat resistance. 〇: Td50 is 30℃ higher than Dispersant 19 (very good) △: Td50 is 10℃ or more higher than Dispersant 19 (good) ×: The difference in Td50 compared to Dispersant 19 is less than 10°C, or is equal to or less than that (poor)

[0169] (viscosity stability) The viscosity stability of the obtained colored composition was evaluated by the following method. The initial viscosity on the day after the preparation of the colored composition and the viscosity over time after aging at 13°C for one month were measured using an E-type viscometer (TOKI SANGYO CO., LTD.'s "ELD type viscometer") at 25°C and a rotation speed of 50 rpm. From the initial viscosity and the viscosity over time values, the viscosity change rate over time was calculated using the following formula, and the viscosity stability was evaluated on a three-level scale. [Change rate of viscosity over time] = |([Initial viscosity] - [Viscosity over time]) / [Initial viscosity]| x 100 ○: Viscosity change rate less than 5% (good) △: Viscosity change rate is 5% or more but less than 10% (practical range) ×: Viscosity change rate 10% or more (bad)

[0170] (Foreign matter evaluation) The obtained colored composition was applied to a glass substrate on which a black matrix had been formed in advance by spin coating, and then dried in a clean oven at 70°C for 20 minutes. Next, the substrate was cooled to room temperature, and then exposed to ultraviolet light through a photomask using an ultra-high pressure mercury lamp. Then, the substrate was spray-developed with a 0.2% by mass aqueous solution of sodium carbonate at 23°C for 30 seconds, washed with ion-exchanged water, and dried. Further, a heat treatment was performed in a clean oven at 230°C for 30 minutes to form a stripe-shaped pattern on the substrate. The pattern was formed so that the film thickness was 2.0 μm after heat treatment at 230°C. The number of foreign particles in the colored pixels was counted using the obtained substrate. The surface was observed using an Olympus Systems metallurgical microscope (BX60) for evaluation. The magnification was set to 500x, and the number of foreign particles observable in any five fields of view was counted in transmission. The fewer the number of foreign particles, the better the dispersibility and compatibility. ◎: The number of foreign objects is less than 3 (very good) ○: The number of foreign objects is 3 or more and less than 20 (good) △: The number of foreign objects is 21 or more and less than 100 (practical) ×: 100 or more foreign objects (defective)

[0171] (Solvent resistance) The obtained colored composition was applied onto an aluminum plate using a #5 bar coater and baked at 200° C. for 1 hour to obtain a colored coating film. The obtained colored coating film was immersed in tetrahydrofuran for 1 hour, and the appearance was visually evaluated. ○: No particular change in appearance (good) △: Slight changes in appearance (still usable) ×: Significant changes in appearance, such as loss of surface gloss, are observed (poor)

[0172] [Table 4]

[0173] <Production of Molded Product> The materials used for the molded body are listed below. [Polyolefin resin] Novatec HD HJ362N (manufactured by Japan Polyethylene Corporation, MFR: 5g / 10min, HDPE). Note that PE is polyethylene. [Inorganic pigments] Calcium carbonate NS#100 (manufactured by Nitto Funka Kogyo Co., Ltd., average particle size 2.1 μm, calcium carbonate)

[0174] [Melt viscosity of polyolefin resin] MFR was measured according to JIS (Japanese Industrial Standards) K-7210. [Average particle size of inorganic pigment] The average particle size was measured using "UPA-EX150" manufactured by Nikkiso Co., Ltd.

[0175] [Example 41] (Molded body 1) 99.74 parts of polyolefin resin, 0.25 parts of inorganic pigment, and 0.01 parts of acidic dispersant were mixed, melt-kneaded in a twin-screw extruder (manufactured by Japan Steel Works), extruded at 200° C., and granulated to obtain a pellet-shaped colored resin composition. Subsequently, 100 parts of the obtained colored resin composition was molded at 200° C. in an injection molding machine (manufactured by Toshiba Machine Co., Ltd.) to obtain a multipurpose test piece (molded body) having a length of 80 mm, a width of 10 mm, and a thickness of 4 mm.

[0176] [Comparative Examples 5 and 6] A pellet-shaped colored resin composition was obtained in the same manner as in Example 41, except that the materials and blending amounts (parts by mass) were changed to those shown in Table 5. Subsequently, multipurpose test pieces were obtained in the same manner as in Example 41 using 100 parts of the obtained colored resin composition.

[0177] The obtained multipurpose test specimen was used to evaluate the Charpy impact strength and dispersibility by the following methods.

[0178] <Impact strength measurement> The notched Charpy impact strength was measured using the obtained multipurpose test specimen in accordance with JIS K7171:2016. In addition, from each measured value obtained, the property retention rate for each measured value was calculated according to the following formula (1) and evaluated according to the following criteria. Note that the higher the property retention rate, the better the strength. Equation (1) Property retention rate (%) = [Measured value of multipurpose test piece containing colored resin composition / measured property value of multipurpose test piece of polyolefin resin alone] x 100 〇: Physical property retention rate of 70% or more (good) ×: Property retention rate less than 70% (defective)

[0179] <Dispersibility> The obtained multipurpose test piece was observed at a magnification of 1000 times using an optical microscope "Digital Microscope VHX-100" (manufactured by Keyence Corporation), and the dispersibility was evaluated according to the following criteria. ○: The number of pigment aggregates with a size of 20 μm or more observed in the field of view is 10 or less (good dispersibility) △: 11 to 30 pieces (practical range) ×: 31 or more (defective)

[0180] [Table 5]

[0181] From the results of Tables 4 and 5, the acidic dispersants of the Examples have good productivity, are heat resistant, and are compatible with resins having different polarities, namely acrylic resin and polyolefin, and can be used as dispersants. Therefore, they can be used to disperse materials in a wide range of applications, such as inks and molded products. On the other hand, in the Comparative Examples, the dispersants with good productivity had low heat resistance and compatibility. In addition, the dispersants with good heat resistance had low compatibility and productivity, and could not solve the problems of the present invention.

Claims

1. An acidic dispersant having a first polymer portion, a second polymer portion, and an acid dianhydride moiety, the first polymer portion comprises a cyclic ester polymer, The second polymer portion comprises a vinyl polymer.

2. 2. The acidic dispersant according to claim 1, having an acid value of 10 to 200 mg KOH / g.

3. 2. The acidic dispersant according to claim 1, wherein the acid dianhydride residue is a residue having an aromatic ring.

4. The acidic dispersant according to claim 1 , wherein the cyclic ester polymer is a polymer containing polylactone.

5. The acidic dispersant according to claim 1, wherein the acidic dispersant contains 20 to 80% by mass of the first polymer portion.

6. A step (1) of synthesizing a vinyl polymer having a hydroxyl group at one end by reacting a thiol group-containing alcohol with a vinyl monomer in the presence of a polymer containing a cyclic ester polymer having a hydroxyl group at one end; Next, the method for producing an acidic dispersant includes a step (2) of reacting these polymers with an acid dianhydride to synthesize an acidic dispersant having a first polymer portion containing a cyclic ester polymer, a second polymer portion containing a vinyl polymer, and an acid dianhydride residue.

7. A dispersion comprising the acidic dispersant according to any one of claims 1 to 5 and a substance to be dispersed.

8. A molded article which is a melt-kneaded mixture of the acidic dispersant according to any one of claims 1 to 5, a dispersed substance, and a resin.

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