WO2012086213A1 - Agent dispersant et composition de dispersion - Google Patents

Agent dispersant et composition de dispersion Download PDF

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Publication number
WO2012086213A1
WO2012086213A1 PCT/JP2011/050897 JP2011050897W WO2012086213A1 WO 2012086213 A1 WO2012086213 A1 WO 2012086213A1 JP 2011050897 W JP2011050897 W JP 2011050897W WO 2012086213 A1 WO2012086213 A1 WO 2012086213A1
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Prior art keywords
group
dispersant
formula
dispersion
atom
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PCT/JP2011/050897
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English (en)
Japanese (ja)
Inventor
和幸 加藤
恭輝 齊藤
真徳 大本
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第一工業製薬株式会社
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Application filed by 第一工業製薬株式会社 filed Critical 第一工業製薬株式会社
Priority to KR1020137015994A priority Critical patent/KR101472700B1/ko
Priority to CN201180062579.9A priority patent/CN103282110B/zh
Publication of WO2012086213A1 publication Critical patent/WO2012086213A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
    • C09D7/40—Additives
    • C09D7/45—Anti-settling agents
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D201/00—Coating compositions based on unspecified macromolecular compounds
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
    • C09K23/42—Ethers, e.g. polyglycol ethers of alcohols or phenols

Definitions

  • the present invention relates to a dispersant and a dispersion composition using the dispersant.
  • Isotropic materials and / or anisotropic materials derived from inorganic or organic materials include hybrid materials, surface protective agents, conductive pastes, conductive inks, sensors, precision analysis elements, optical memories, liquid crystal display elements, nanomagnets, heat transfer materials.
  • hybrid materials surface protective agents, conductive pastes, conductive inks, sensors, precision analysis elements, optical memories, liquid crystal display elements, nanomagnets, heat transfer materials.
  • As a main material in application fields such as media, high-performance catalysts for fuel cells, organic solar cells, nano glass devices, abrasives, drug carriers, environmental catalysts, paints, printing inks, inkjet inks, resists for color filters, inks for writing instruments, etc. in use.
  • the isotropic material and / or anisotropic material derived from the inorganic or organic material is efficiently processed by preparing a dispersion as fine particles in an aqueous dispersion medium or a non-aqueous dispersion medium. It is used industrially as a substance that improves properties, product characteristics and material properties, and contributes to quality stabilization and yield improvement during production.
  • organic compound having a carboxyl group as the proposed low molecular weight dispersant, for example, formic acid, acetic acid, propionic acid, butanoic acid, hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid, decanoic acid, undecanoic acid, lauric acid
  • carboxylic acids having 1 to 20 carbon atoms such as myristic acid, palmitic acid, stearic acid, oleic acid, linoleic acid, linolenic acid, hydroxycarboxylic acids, alicyclic having 6 to 34 carbon atoms.
  • aromatic carboxylic acids for example, formic acid, acetic acid, propionic acid, butanoic acid, hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid, decanoic acid, undecanoic acid, lauric acid
  • alkenyl succinic anhydrides include octenyl succinic anhydride, dodecenyl succinic anhydride, hexadecenyl succinic anhydride, and the like.
  • organic compounds having a thiol group include mercaptoethanol, mercapto-2-propanol, 1-mercapto-2, 3-propanediol, 3-mercaptopropyltrimethoxysilane, mercaptosuccinic acid, hexanethiol, pentanedithiol, and dodecanethiol.
  • alkanethiols such as undecanethiol and decanethiol.
  • Examples of the organic compound having a phenol ring include triphenylphosphine, tributylphosphine, trioctylphosphine, and tributylphosphine.
  • Examples of the organic compound having an amino group include propylamine, butylamine, hexylamine, heptylamine, octylamine, 2-ethylhexylamine, nonylamine, decylamine, dodecylamine, hexadecylamine, and oleylamine.
  • a polymer type dispersion having a skeleton such as a carboxyl group, an amino group, a hydroxyl group, an ester bond, an amide bond, an aromatic ring, and a heterocyclic ring which was mainly developed as a dispersant for pigments and the like.
  • the agent has also been diverted to this application, the DISPERBYK series manufactured by BYK Chemie, the Ciba EFKA series manufactured by Fuka Additives, the Solsper series manufactured by Lubrizol, and the Lubrizol series.
  • the Dispalon series manufactured by Enomoto Kasei is available on the market.
  • anionic surfactants include higher fatty acid salts, alkyl sulfonates, alpha olefin sulfonates, alkane sulfonates, and alkylbenzenes. Sulfonates, sulfosuccinates, alkyl sulfates, alkyl ether sulfates, alkyl phosphates, alkyl ether phosphates, alkyl ether carboxylates, alpha sulfo fatty acid methyl esters, methyl taurates and so on.
  • Nonionic surfactants include, for example, glycerin fatty acid ester, polyglycerin fatty acid ester, sucrose fatty acid ester, sorbitan fatty acid ester, polyoxyethylene sorbitan fatty acid ester, polyoxyethylene alkyl ether, polyoxyethylene alkylphenyl ether, polyoxy Examples include ethylene fatty acid esters, fatty acid alkanolamides, and alkyl glucosides.
  • Examples of amphoteric surfactants include alkyl betaines, fatty acid amidopropyl betaines, and alkylamine oxides.
  • cationic surfactant examples include alkyl trimethyl ammonium salt, dialkyl dimethyl ammonium salt, alkyl dimethyl benzyl ammonium salt, and alkyl pyridinium salt.
  • polymer surfactants such as fluorine-based surfactants, cellulose derivatives, polycarboxylates, and polystyrene sulfonates.
  • the interfacial adsorption action based on the hydrophobic interaction of the dispersant the electroadsorption action due to the ionic group, the ⁇ -electron interaction derived from the aromatic ring, and between the particles
  • Use of electrostatic repulsion between particles by formation of multi-layers, dispersion stabilization by formation of steric barriers, and addition of protective colloids and thickeners as stabilizers are also effective, stabilizing dispersion and suppressing aggregation. A variety of measures that can achieve this can be adopted.
  • the various ionic surfactants described above are extremely effective as aqueous dispersants, but many of them cannot be dissolved in a non-aqueous dispersion medium, and their application range is extremely limited.
  • the size of the dispersoid particles is a micrometer size
  • the size of the dispersoid particles is nanometer size or sub-nanometer size
  • the dispersion system design with a high molecular weight dispersant is considered due to the difference between the size of the dispersoid particles and the size of the dispersant molecules. Can be difficult or limited.
  • nanometer-sized inorganic fine particles particle size: 1 to 100 nm
  • polymer nanocomposites nanometer-sized inorganic fine particles or composite materials in which organic fillers and pigments are finely dispersed in a resin
  • nanometer-sized particles tend to aggregate and have a low affinity for the resin, so that it is extremely difficult to uniformly disperse in the resin.
  • an aqueous dispersion medium In order to uniformly disperse nanometer-sized particles in a resin, it is difficult or limited to use an aqueous dispersion medium.
  • a nanoparticle is uniformly dispersed in a non-aqueous dispersion medium using a dispersant.
  • Patent Document 1 polyoxyethylene alkyl phosphoric acid and polyoxyethylene alkyl carboxylate as mentioned in the above patent are used (Patent Document 1).
  • the dispersoid particles are coated with a surface modifier or a surface protective agent or dispersed.
  • Technology is known to impregnate the surface particles with a surface modifier, etc., but in the prior art, the type of dispersion medium and the amount of dispersoid added are often limited, and the range of use is extremely limited. No dispersant, surface modifier or surface protective agent has been found that can solve this problem.
  • Dispersants that can solve the above problems, that is, without being limited by the type of dispersion medium and the amount of dispersoid added, find a dispersant that is versatile for a wide range of materials, and non-aqueous using the dispersant Using the dispersion or the dispersant as a surface modifier or surface protective agent for a dispersoid, a powdery, granular or pasty substance coated with or impregnated with the dispersant is obtained. If they are used, they are of great industrial utility in terms of solvent substitution, polarity change, mixing with resins and resin solutions.
  • Patent Document 2 discloses metal colloidal particles composed of metal nanoparticles (A) and protective colloids (B) covering the metal nanoparticles (A), Metal colloidal particles in which the protective colloid (B) is composed of an organic compound (B1) having a carboxyl group and a polymer dispersant (B2) are disclosed.
  • Japanese Patent Application No. 2010-120122 which has not been disclosed at the time of filing of the present application, discloses a dispersant for a non-aqueous dispersion medium containing a branched alkyl group and / or alkenyl group. If this dispersant is used, it can be applied to a wide range of dispersoids, and excellent dispersion stability can be exhibited with a small amount of addition. However, development of a dispersant capable of dispersing a larger amount of dispersoids such as inorganic fine particles and fillers is desired.
  • polyoxyethylene alkyl phosphoric acid and polyoxyethylene alkyl carboxylate may not provide desired dispersibility depending on the combination of inorganic fine particles or filler and resin.
  • a dispersion prepared by combining polyoxyethylene alkyl carboxylic acid and phenoxyethyl acrylate (PHE), which is an aromatic general-purpose photo-curing resin material is remarkably unclear and shows a decrease in dispersibility.
  • PHE phenoxyethyl acrylate
  • the present invention has been made in view of such problems of the prior art, and its purpose is applicable to a wide range of dispersoids, and exhibits excellent dispersion stability with a small amount of addition. It is another object of the present invention to provide a dispersing agent for dispersion medium suitable for dispersing a large amount of dispersoid. In addition, an object of the present invention is to provide a dispersion composition using the dispersant. Another object of the present invention is to provide organic particles or inorganic particles that are coated with or impregnated with the dispersant.
  • the dispersant of the present invention is a dispersant comprising a compound represented by the following formula (1).
  • R represents a hydrocarbon group containing at least one aromatic ring
  • AO in the formula (1) represents an oxyalkylene group having 1 to 4 carbon atoms
  • n represents an alkylene oxide.
  • a numerical value in the range of 1 to 30 indicating the average number of added moles, wherein X in the formula (1) is an O atom, S atom, —NR1- (R1 is an H atom or a C atom, an H atom, or an O atom.
  • Y is a linking group composed of any one of C, H, and O atoms.
  • R in the formula (1) is preferably a styrenated phenyl group represented by the following formula (2).
  • k in the formula (2) is an average value and is a numerical value in the range of 1 to 5.
  • Y in the formula (1) is preferably an alkylene group having 1 to 15 carbon atoms or a functional group represented by the following formula (3).
  • Z in the formula (3) is any selected from an alkylene group having 1 to 15 carbon atoms, a vinylene group, a phenylene group, and a carboxyl group-containing phenylene group.
  • the inorganic particles of the present invention are either coated with the dispersant described above or impregnated with the dispersant.
  • the dispersion composition of the present invention is obtained by dispersing inorganic particles in a non-aqueous dispersion medium using any of the dispersants described above.
  • the coating composition of the present invention contains the above dispersion composition using a resin as a non-aqueous dispersion medium.
  • the dispersion composition of the present invention contains a mixture of the above dispersion composition and resin using a solvent as a non-aqueous dispersion medium.
  • the member of the present invention is obtained by applying any of the above coating compositions on a substrate and then reacting them.
  • inorganic fine particles or fillers can be dispersed in a dispersion medium that has been difficult with conventional dispersants, and a highly transparent and stable dispersion composition can be provided.
  • the dispersing agent which can disperse
  • the dispersion composition using the dispersing agent and the coating composition containing the dispersion composition can be provided.
  • the dispersant of the present invention has a dispersion medium affinity part comprising a hydrocarbon group containing at least one aromatic ring, and a dispersoid affinity part comprising an oxyalkylene group and a carboxyl group.
  • the dispersion medium affinity part and the dispersoid affinity part are connected by a linking group X.
  • R is a hydrocarbon group containing at least one aromatic ring, specifically, the above-described formula (2)
  • functional groups containing an octylphenyl group, a nonylphenyl group, a cumylphenyl group, an o-phenyl-phenyl group, a p-phenyl-phenyl group, and the like can be given.
  • naphthalene includes two aromatic rings and anthracene includes three aromatic rings.
  • anthracene includes three aromatic rings.
  • the aromatic ring greatly contributes to the improvement of dispersibility.
  • the styrenated phenyl group-containing compound represented by the formula (2) can be suitably used to achieve the object of the present invention.
  • the linking group (X) is a linking group composed of any one of an O atom, an S atom, and —NR1-, and R1 is a functional group composed of an H atom, or a C atom, an H atom, or an O atom. It is.
  • R1 include saturated linear alkyl groups having 1 to 18 carbon atoms such as n-hexyl and n-octyl groups, saturated branched alkyl groups having 1 to 18 carbon atoms such as 2-ethylhexyl and isodecyl groups, and linole groups. And unsaturated long chain alkyl groups such as linolenic group, oleyl group, coconut alkyl group, beef tallow alkyl group, and cured beef tallow alkyl group.
  • Oxyalkylene group (AO) n For the alkylene oxide species suitably selected for the dispersant of the present invention, in formula (1), AO represents an oxyalkylene group having 1 to 4 carbon atoms, specifically, the alkylene oxide having 2 carbon atoms is ethylene oxide. The alkylene oxide having 3 carbon atoms is propylene oxide. The alkylene oxide having 4 carbon atoms is tetrahydrofuran or butylene oxide, and is preferably 1,2-butylene oxide or 2,3-butylene oxide.
  • the oxyalkylene chain (-(AO) n-) is a random polymerization of two or more alkylene oxides even if the alkylene oxide is a homopolymer chain for the purpose of adjusting the dispersion medium affinity of the dispersant. It may be a chain, a block polymer chain, or a combination thereof.
  • N which shows the average added mole number of the alkylene oxide of Formula (1) is in the range of 1 to 30, but is preferably in the range of 3 to 20.
  • Linking group (Y) The linking group (Y) can be selected from known structures comprising a carbon atom, a hydrogen atom, and an oxygen atom, but preferably comprises a saturated hydrocarbon group, an unsaturated hydrocarbon group, an ether group, a carbonyl group, and an ester group. It may have an alicyclic structure or an aromatic ring structure, and may have a repeating unit.
  • the linking group Y contains a nitrogen atom and / or a sulfur atom and / or a phosphorus atom, the linking group Y is not suitable as a structural factor of the dispersant of the present invention because it has an action of weakening the affinity effect of the carboxyl group on the dispersoid. .
  • Y in the formula (1) is preferably an alkylene group having 1 to 15 carbon atoms, and more preferably an alkylene group having 1 to 8 carbon atoms.
  • Y in the formula (1) is preferably a substance represented by the above formula (3).
  • Z is either selected from an alkylene group having 1 to 15 carbon atoms, a vinylene group, a phenylene group, and a carboxyl group-containing phenylene group.
  • the dispersoid particles dispersed by the dispersant of the present invention can be selected from inorganic particles and / or organic particles.
  • the inorganic substance-derived particles include iron, aluminum, chromium, nickel, cobalt, zinc, tungsten, indium, tin, palladium, zirconium, titanium, copper, silver, gold, platinum, and alloys thereof, or a mixture thereof. Can be used.
  • alkanoic acids and fatty acids alkanoic acids and fatty acids, hydroxycarboxylic acids, alicyclic, aromatic carboxylic acids, alkenyl succinic anhydrides, thiols, phenol derivatives
  • protective agents such as an amphiphilic polymer, a high molecular surfactant, and a low molecular surfactant.
  • organic particles azo, diazo, condensed azo, thioindigo, indanthrone, quinacridone, anthraquinone, benzimidazolone, perylene, phthalocyanine, anthrapyridine, dioxazine, etc.
  • Organic pigment polyethylene resin, polypropylene resin, polyester resin, nylon resin, polyamide resin, aramid resin, acrylic resin, vinylon resin, urethane resin, melamine resin, polystyrene resin, polylactic acid, acetate fiber, cellulose, hemicellulose, lignin, chitin , Chitosan, starch, polyacetal, aramid resin, polycarbonate, polyphenylene ether, polyether ether ketone, polyether ketone polybutylene terephthalate, polyethylene naphthalate, poly Chi naphthalate, polysulfone, polyphenylene sulfide, polyimides or the like.
  • the dispersoid particles dispersed by the dispersant of the present invention may be crystalline or amorphous. Further, the dispersoid particles dispersed by the dispersant of the present invention may be isotropic particles, anisotropic particles, or may be fibrous.
  • dispersoid particles that become a dispersoid in the present invention those obtained by a known method can be used.
  • a method for preparing fine particles a top-down method in which coarse particles are mechanically pulverized and refined, and a bottom in which particles are formed through a cluster state in which several unit particles are generated and aggregated.
  • any one prepared by any method can be suitably used. Further, they may be either a wet method or a dry method.
  • the bottom-up method includes a physical method and a chemical method, and any method may be used.
  • the dispersant of the present invention may be used in a top-down process in which coarse particles are mechanically pulverized and refined to form a number of unit particles that pass through the agglomerated cluster state. May be used in a bottom-up process in which particles are formed, or after preparing fine particles in advance by the above-described method, a surface modifier or surface protection is used to stably remove the dispersoid particles from the medium. It is also possible to use particles taken out after being coated or impregnated with a known protective agent called an agent. As the protective agent, the above-mentioned known dispersants can be substituted.
  • a method for preparing metal nanoparticles among the dispersoid particles will be exemplified.
  • a representative example of a physical method is an in-gas evaporation method in which bulk metal is evaporated in an inert gas and cooled and condensed by collision with the gas to generate nanoparticles.
  • Chemical methods include a liquid phase reduction method in which metal ions are reduced in the liquid phase in the presence of a protective agent, and the generated zero-valent metal is stabilized at the nanosize, and a metal complex thermal decomposition method. is there.
  • a chemical reduction method an electrochemical reduction method, a photoreduction method, a method combining a chemical reduction method and a light irradiation method, or the like can be used.
  • the dispersoid particles that can be suitably used in the present invention may be those obtained by any of the top-down method and the bottom-up method, and they are aqueous, non-aqueous, and in the gas phase. It may be prepared in any environment.
  • Dispersion medium which can be used in the present invention includes toluene, xylene, aromatic hydrocarbon solvents, hydrocarbon solvents such as n-hexane, cyclohexane and n-heptane, and halogenated carbonization such as methylene chloride, chloroform and dichloroethane.
  • Ether solvents such as hydrogen solvents, ethyl ether, isopropyl ether, dioxane, tetrahydrofuran, dibutyl ether, butyl ethyl ether, methyl-t-butyl ether, terpinyl methyl ether, dihydroterpinyl methyl ether, diglyme 1,3-dioxolane Solvent, acetone, acetophenone, methyl ethyl ketone, methyl propyl ketone, diethyl ketone, methyl n-butyl ketone, methyl isobutyl ketone, dipropyl ketone, diisobutyl ketone, methyl amyl ketone, aceto Ketone solvents such as nilacetone, isophorone, cyclohexanone, methylcyclohexanone, 2- (1-cyclohexenyl) cyclohexanone methyl iso
  • glycol ether solvents of these monoethers and dialkyl ether solvents such as acetate solvents of diethers, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl isobutyl ether, dipropylene glycol dimethyl ether, and dipropylene glycol diethyl ether.
  • Alcohol solvents such as Coal 180N and Fine Oxocol 2000, glycol solvents such as ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol, dipropylene glycol, 1,3-butylene glycol, hexylene glycol, polyethylene glycol and polypropylene glycol Is mentioned.
  • glycol solvents such as ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol, dipropylene glycol, 1,3-butylene glycol, hexylene glycol, polyethylene glycol and polypropylene glycol Is mentioned.
  • amide solvents such as dimethylacetamide and dimethylformamide.
  • (meth) acrylic acid having a reactive group as a dispersion medium (meth) acrylic acid esters, vinyl monomers such as vinyl acetate, vinyl ether derivatives, and ethylenically unsaturated monomers such as polyallyl derivatives can also be used.
  • various resins, oligomers, and monomers used for ordinary paints, adhesives, and moldings can be used without any particular limitation. Specific examples include acrylic resins, polyester resins, alkyd resins, urethane resins, silicone resins, fluororesins, epoxy resins, polycarbonate resins, polyvinyl chloride resins, and polypinyl alcohols.
  • the said dispersion medium can be used suitably individually or in mixture of 2 or more types.
  • the dispersant of the present invention is intended to provide a fine particle dispersion in a non-aqueous environment, whether intentionally or accidentally with respect to the dispersion medium, during the production process of the fine particle dispersion, Or, for the purpose of use or in the final product design, mixing or mixing of water is not denied.
  • the dispersant of the present invention can be produced by a known method, and the composition is optimally selected by specifically limiting the type of the hydrophobic group, the alkylene oxide type and its addition form, the added molar amount, the linking group, etc. within the above range. By doing so, a wider variety of dispersoids can be dispersed than in known dispersants, and the industrial utility value is great in that the dispersoids can be dispersed and stabilized in a wider variety of dispersion media.
  • the dispersant of the present invention can be used by reducing the content of ionic species, particularly alkali metal ions, alkaline earth metal ions, heavy metal ions, and halogen ions contained by a known purification method.
  • the ionic species in the dispersant is greatly affected by the dispersion stability, touch resistance, oxidation resistance, electrical properties (conductive properties, insulation properties), aging stability, heat resistance, low humidity, and weather resistance of the dispersion.
  • it is desirable that the content of the ions is less than 10 ppm in the dispersant.
  • the content of the dispersant suitably employed in the present invention is not particularly limited as long as the dispersoid can be uniformly dispersed in the non-aqueous dispersion medium, and varies depending on the application, etc.
  • the total body composition is preferably in the range of 0.1 to 20% by weight, based on 100% by weight, and the content of the dispersoid particles is preferably in the range of 1 to 90% by weight. Further, the content of the dispersant is preferably in the range of 1 to 300% by weight with respect to the dispersoid particles.
  • the content of the dispersion medium is preferably in the range of 1 to 99% by weight with respect to 100% by weight of the total dispersion composition.
  • the average particle size of the dispersoid particles is preferably in the range of 1 to 500 nm, more preferably in the range of 1 to 100 nm.
  • the dispersant of the present invention can be produced by a known method.
  • a general nonionic surfactant compound in which alkylene oxide is added to alcohol, amine, or thiol is used as a raw material, and a monohalogenated lower carboxylic acid or a salt thereof is used to react with a hydroxyl group at the end of alkylene oxide in the presence of a base.
  • a monohalogenated lower carboxylic acid or a salt thereof is used to react with a hydroxyl group at the end of alkylene oxide in the presence of a base.
  • it can manufacture by the method or the method by a ring-opening reaction with the hydroxyl group of the alkylene oxide terminal using an acid anhydride, it does not limit to these methods.
  • the dispersion composition of the present invention can be prepared using known stirring means, homogenizing means, and dispersing means.
  • dispersers that can be used include roll mills such as two rolls and three rolls, ball mills such as ball mills and vibration ball mills, paint shakers, continuous disk type bead mills, bead mills such as continuous annular type bead mills, sand mills, and jets. Mill etc. are mentioned.
  • the dispersion treatment can be performed in an ultrasonic wave generation bath.
  • the dispersant of the present invention not only exhibits an excellent dispersion stabilization effect compared to known techniques for the dispersion stabilization of dispersoid particles in a non-aqueous dispersion medium, but also disperses the dispersoid particles as a medium. It can be used as a protective agent for taking out from inside stably.
  • Functions of the protective agent for stably taking out the dispersoid particles from the medium include suppression of aggregation of the generated particles, suppression of adsorption to the container wall surface and prevention of contamination, provision of easy redispersibility, oxidation of metal particles, prevention of particle surface Examples include surface modification, prevention of functional surface deterioration, solvent replacement and shock mitigation during polarity change, powder flowability improvement, and powder solidification prevention.
  • the dispersant of the present invention is superior to the known protective agents in terms of the above functions, and is more suitable than the known protective agents by optimally selecting the addition form of alkylene oxide and the addition molar amount thereof, the type of hydrophobic group, the linking group, and the like. A desired dispersoid can be dispersed and stabilized in a wide range of dispersion media.
  • Coating composition containing the dispersion composition of the present invention using a resin as a non-aqueous dispersion medium or coating composition containing a mixture of the dispersion composition of the present invention and a resin using a solvent as a non-aqueous dispersion medium As a base material on which the coating is applied, for example, glass, resin film, glass composite, ceramics, metal / steel plate and the like can be used.
  • Example 5 Synthesis of dispersant of Example 3
  • a phenyl group (k 2), AO: ethylene oxide, n: 8, X: O, Y: COCH 2 CH 2 ) was obtained.
  • Production Example 6 (Synthesis of dispersant of Example 4)
  • Electromer HRI-01 Electromer HRI-01
  • o-phenylphenoxyethyl acrylate 28.5 And 12 parts of 3-methoxy-3-methylbutanol were added and mixed, and then methanol was removed under reduced pressure using a rotary evaporator to obtain an acrylate monomer dispersion of zirconium oxide.
  • dispersions were made using commercially available materials.
  • the evaluation criteria are as follows. ⁇ : When the dispersion is placed in a glass container having a depth of 1 cm, 12-point alphabet characters are clearly visible. The dispersion is transparent. X: When the dispersion is put in a glass container having a depth of 1 cm, 12-point alphabet characters cannot be clearly seen. The dispersion is turbid. The results are shown in Table 1.
  • Examples 1 to 6 using a dispersant having an aromatic ring in the hydrophobic group and a terminal group of carboxylic acid are very excellent for a dispersoid containing an aromatic acrylate monomer.
  • FIG. On the other hand, in Comparative Examples 1 to 3 and 6 in which the hydrophobic group did not contain an aromatic ring, dispersibility was poor with the same amount of dispersant added as in Examples 1 to 6. Furthermore, even in the case where the hydrophobic group contains an aromatic ring, in the case of Comparative Example 4 in which the terminal group is a carboxylic acid sodium salt, or in Comparative Example 5 in which the terminal group is an alcohol, the dispersibility in the solvent is greatly inferior. As a result. From this, it can be seen that in the present invention, the carboxylic acid of the terminal group together with the aromatic ring has an important role in dispersibility.
  • Some of the dispersions shown in Examples 1 to 6 have a low viscosity of 1400 to 4000 mPa ⁇ sec, depending on the combination of the dispersant and the acrylate monomer, regardless of the condition of not containing a diluent solvent. When the viscosity of the dispersion is low, coating on the substrate becomes easy, and thus it can be said that the industrial value is high.
  • the refractive indexes of the dispersions shown in Examples 1 to 6 are 1.6 to 1.645, which are improved as compared with the original acrylate monomer species, respectively.
  • the dispersion composition of the present invention includes a hybrid material, a surface protective agent, a conductive paste, a conductive ink, a sensor, a precision analysis element, an optical memory, a liquid crystal display element, a nanomagnet, a heat transfer medium, a high-performance catalyst for a fuel cell, Organic solar cells, nano glass devices, abrasives, drug carriers, environmental catalysts, paints, printing inks, inkjet inks, color filter resists, writing instrument inks, optical thin films, adhesives, antireflection films, hard coat films, etc.
  • the dispersant of the present invention stabilizes dispersion of the isotropic material and / or anisotropic material derived from a nano-sized inorganic substance or organic substance, which is a main component in the above-mentioned product and its production process, in a non-aqueous dispersion medium. It is effective for obtaining desired product characteristics, processing characteristics, quality stabilization, and productivity improvement by suppressing dispersoid aggregation in the dispersion medium and achieving long-term dispersion stabilization.

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
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  • Polyethers (AREA)

Abstract

L'invention concerne un agent dispersant pour des milieux de dispersion non aqueux qui est applicable à une grande plage de dispersoïdes et qui permet d'obtenir une excellente stabilité de dispersion même lorsqu'il est ajouté dans une petite quantité. Cet agent dispersant consiste essentiellement en un composé représenté par la formule (1) [dans laquelle R représente un groupe hydrocarboné ayant au moins un noyau aromatique ; AO représente oxyalkylène en C1-4 ; n représente le nombre moyen de moles d'oxyde d'alkylène ajoutées et est un nombre de 1 à 30 ; X représente un groupe de liaison composé de O, S et/ou -NR1- (où R1 représente un atome de H ou un groupe composé de C, H et/ou O) ; et Y représente un groupe de liaison composé de C, H et/ou O].
PCT/JP2011/050897 2010-12-22 2011-01-19 Agent dispersant et composition de dispersion WO2012086213A1 (fr)

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CN201180062579.9A CN103282110B (zh) 2010-12-22 2011-01-19 分散剂和分散体组合物

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JP6604475B2 (ja) * 2015-02-06 2019-11-13 日油株式会社 非水系分散剤および非水系分散体組成物
CN104865359A (zh) * 2015-05-11 2015-08-26 刘俊平 餐渣液再生油染色剂
US10287448B2 (en) * 2016-07-08 2019-05-14 Evonik Degussa Gmbh Universal pigment preparation
CN112105680A (zh) 2018-05-11 2020-12-18 株式会社三养社 固体分散体、其制备方法、使用其的扩链聚氨酯和包含其的环氧树脂组合物
US20220403106A1 (en) * 2019-09-20 2022-12-22 Basf Se Polyalkyleneimine-based polymer containing polyether chains

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2000262883A (ja) * 1999-03-19 2000-09-26 Kao Corp 無機粉末用油中分散剤
JP2001276596A (ja) * 2000-04-04 2001-10-09 Kao Corp 無機粉末用水系分散剤
JP2007007648A (ja) * 2005-06-30 2007-01-18 Samsung Electronics Co Ltd 分散剤、それを含むペースト組成物、及びそれを使用して製造される無機素子、並びにそれを含むディスプレイ装置
WO2010129662A1 (fr) * 2009-05-08 2010-11-11 Croda, Inc. Tensioactifs dans des formulations agrochimiques

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE602005023088D1 (de) * 2004-03-26 2010-10-07 Toyota Motor Co Ltd Dispergiermittel oder ein die Beschichtungsfähigkeit verbesserndes Mittel

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2000262883A (ja) * 1999-03-19 2000-09-26 Kao Corp 無機粉末用油中分散剤
JP2001276596A (ja) * 2000-04-04 2001-10-09 Kao Corp 無機粉末用水系分散剤
JP2007007648A (ja) * 2005-06-30 2007-01-18 Samsung Electronics Co Ltd 分散剤、それを含むペースト組成物、及びそれを使用して製造される無機素子、並びにそれを含むディスプレイ装置
WO2010129662A1 (fr) * 2009-05-08 2010-11-11 Croda, Inc. Tensioactifs dans des formulations agrochimiques

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TW201226049A (en) 2012-07-01
KR20130096307A (ko) 2013-08-29
KR101472700B1 (ko) 2014-12-12
JP5727215B2 (ja) 2015-06-03
TWI461238B (zh) 2014-11-21
CN103282110A (zh) 2013-09-04
CN103282110B (zh) 2015-08-26

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