TW201226049A - Dispersant and dispersion composition - Google Patents

Abstract

Provided is a dispersant for nonaqueous dispersion media which is applicable to a wide range of dispersoids and which can achieve excellent dispersion stability even when added in a small amount. This dispersant consists essentially of a compound represented by formula (1) [wherein R is a hydrocarbon group having at least one aromatic ring; AO is C1-4 oxyalkylene; n represents the average number of moles of alkylene oxide added and is a number of 1 to 30; X is a connecting group composed of O, S and/or -NR1- (wherein R1 is a H atom or a group composed of C, H and/or O); and Y is a connecting group composed of C, H and/or O].

Description

201226049 VI. Description of the Invention: [Technical Field of the Invention] The present invention relates to a dispersant and a dispersion composition using the dispersant. [Prior Art] An isotropic material derived from inorganic substances or derived from organic matter and/or an anisotropic material is used as a host material in the following fields of use: a hybrid material, a surface protective agent, a conductive paste 1 electrical ink , sensor precision analysis components, optical memory, liquid crystal display components, nano magnets, heat transfer media, high performance catalysts for fuel cells, organic solar cells, nano glass components, abrasives, drug carriers, environmental catalysts, Coatings, printing inks, inkjet inkjets, color filters, resists for tablets, inks for writing instruments, etc. In this case, the above-mentioned inorganic material or organic-derived isotropic material and/or anisotropic material is used as an inorganic dispersion (aqueous dispersion medium) or a non-aqueous dispersion medium (non-aqueous dispersion medium) as fine particles. By using the medium dispersion dispersion, it is industrially utilized as a substance which contributes to the improvement of the processing characteristics, the product characteristics, and the physical properties of the material, contributes to the quality stabilization, and improves the yield at the time of production. On the other hand, in order to change the material of the dispersoid, to miniaturize the particle size, and to control the shape, it is difficult to stabilize the dispersion of the dispersoid and to cause agglomeration of the disperse in the dispersion medium in a short period of time. Dispersion = agglomeration not only results in reduced productivity, reduced processing characteristics, reduced handleability, and reduced yield in the manufacture of dispersions, but also results in a reduction in the properties, material properties and quality of the final product. Others, it is known that appearance, such as transparency, flowering, puerarin, reduction in color strength, color separation, and cracking, are also caused. In order to know π A, both disperse agglomerates are suppressed to achieve dispersion stabilization, and a dispersant is used. As a proposed low molecular weight dispersant, an organic compound having a carboxyl group 'e.g., except for tannic acid, acetic acid, propionic acid, butyric acid, caproic acid, heptanoic acid, caprylic acid, capric acid, capric acid, deca-alkanoic acid, In addition to saturated, unsaturated carboxylic acids such as lauric acid, self-derived acid, palmitic acid, stearic acid, oleic acid, linoleic acid, and linoleic acid, there are also hydroxycarboxylic acids and carbon numbers. 6 to 34 of the alicyclic family 'aromatic reading acid and so on. The alkenyl number (iv) needles are: octyl succinic anhydride, undecyl succinic anhydride, hexadecenyl boroic anhydride and the like. Organic compounds having a thiol group, for example, mercaptoethanol, thiol-2-propanol, 1-mercapto-2,3-propanediol, %mercaptopropyltrimethoxy decane, decyl succinic acid, hexyl mercaptan An alkanethiol such as pentanedithiol, dodecanethiol, undecylmercaptan or decyl mercaptan. The organic compound having a phenol ring may, for example, be triphenylphosphine, tributylphosphine, trioctylphosphine, tributylphosphine or the like. Organic compounds having an amine group, such as: propylamine, butylamine, hexylamine, heptylamine, octylamine, 2-ethylhexylamine 'decalamine, decylamine, dodecylamine, hexadecylamine, oleylamine )Wait. In addition, a high molecular weight dispersing agent is mainly developed as a dispersing agent for a pigment or the like, and a polymer type dispersing agent having a skeleton such as a carboxyl group, an amine group, a hydroxyl group, an ester bond, a guanamine bond, an aromatic ring or a hetero ring. Used in this application, it is commercially available as: DISPERBYK series manufactured by Byk Chemie's Ciba EFKA series manufactured by EFKa Additives, and 201226049 manufactured by Lubrizol.

Solsperse series, mspARX〇N series of Nanben Chemical Company. Others also propose to use existing surfactants as dispersants, anionic surfactants, such as: higher fatty acid salts, alkyl sulfonates, α-olefin sulfonates, alkane sulfonates, alkyl benzene sulfonates Acid salt, sulfosuccinate salt, alkyl sulfate salt, alkyl ether sulfate salt, alkyl phosphate salt, alkyl cyanoic acid S sulfonium salt, decyl sulfonate, α _ zeaphthyl Fatty acid methyl ester salt, methyl bovine acid, and the like. Nonionic surfactants include, for example, glycerol fatty acid esters, polyglycerol fatty acid esters, sucrose fatty acid esters, sorbitan fatty acid esters, polyoxyethyl sorbitan fatty acid esters, polyoxygen Alkyl ether, polyoxyethylene ethyl phenyl ether, polyoxyethyl alcohol ester, fatty acid alkanolamine, alkyl glucoside, and the like. The amphoteric surfactants are, for example, alkylbetaine, fatty acid amidinopropyl betaine, alkylamine oxide and the like. The cation surfactant [e.g.] is an alkyltrimethylammonium salt, a dialkyldimethylammonium salt, a H-methylbenzyl group (tetra), a pyridinium salt or the like. Others include a surfactant such as a fluorine-based surfactant and a cellulose derivative, a polyvalent (tetra) salt, and a polystyrene sulfonate. In order to suppress the aggregation of the dispersion by using the above-mentioned conventional dispersant to obtain a stable dispersion composition, research is being carried out, but in sub-(4), diversification of dispersoids, miniaturization of particle size of dispersoids, and various shapes. The quality of the final product, the improvement of productivity, and the enhancement of the characteristics: The requirements, etc., the dispersant that has been proposed cannot fully meet the requirements: Time, use: Based on dispersion, ionic basis, for example: When the dispersing medium (dispersion medium) is the hydrophobic interaction of the aqueous agent, the interface adsorption 201226049, and the fragrant Jf-derived particles, between the particles formed by the electric double layer, Use, and the formation of three-dimensional barrier scorpion electrostatic repulsion as a protective agent and thickener, are all functions, and add a variety of methods of stabilization and agglutination inhibition, the method 'can be used to achieve dispersion, on the other hand, due to The electrostatic interface caused by the non-aqueous ionic group is 'hydrophobic interaction, the fruit is extremely limited, so the dispersant disperses (4) electrostatic repulsion The effect of dispersing the particles and the dispersing agent ~ 'surface adsorption' is largely determined. In fact, the acid-base interaction between the two groups is selected. Change the optimization, and divide _=' = ^ mass ^ surface characteristics and the actual situation is together with the dispersion eight: in the extremely limited situation, with the dispersion used:! The affinity of the media must also be - and ^ (d) to choose the most suitable dispersant. It is effective to describe various ionic interface activities, but it is extremely limited as a dispersing agent in non-aqueous systems. Most of the knives are difficult to dissolve. 'The scope of application: In addition, when the size of the dispersed particles is micro*multiple adsorption points to adopt multi-point adsorption, and the protective layer with thick barriers is used to design the dispersion system, Compared with: = agent, but when the dispersion is clear, the Q-knife is scattered in the summer, because the small size of the dispersed particles is nanometer size and sub-nano (Sub·110), therefore, by the size of the high molecular weight and dispersant molecules... +^^1 to design the dispersion system has _ or limited. ,...If the size of the molecule is significantly larger, the size of the polymer is as large as the size of the particle, and the powder is dispersed and bridged between the dispersion plasmid 201226049 and the dispersant. There are many points of adsorption and collection, so there is a fundamental problem in the aggregation between the molecules of the dispersion and the dispersant, which promotes the aggregation of the dispersed particles. Furthermore, 'in order to achieve the goal of dispersion stabilization, the usual / knife-split particles and dispersant', using the stronger interaction between the design 1 to design the distribution of the 糸 疋 疋 疋 分散 分散 分散 分散 分散In addition to the substitution and polarity change, the mechanical and chemical stability, the removal of the dispersed particles, the film formation, and the film formation at low temperatures and in time, when the dispersant is removed, the performance is required. It is required to have a characteristic that is easy to be detached from the interface of the dispersant, and this performance is improved in productivity and processing characteristics of the final product. The aspect of quality stability is an important factor. In this view, the existing: fully meets the required performance. In addition, a composite material in which nanometer-sized inorganic fine particles (particle size 1 to io 〇 nm) or organic fillers and pigments are finely dispersed in a resin is called a poly "nano composite material", and it is desired to The composite material is used to improve the refractive index and the like, and is used in optical materials. However, particles having a nanometer size are easily aggregated and have low affinity for the resin, so that it is extremely difficult to uniformly disperse in the resin. When the particle size of the rice is dispersed in the resin, it is difficult or limited to use the aqueous dispersion medium. The effective method is to disperse the nanoparticle uniformly in the non-aqueous dispersion medium by using a dispersant to prepare the dispersion and dissolve the resin. An example in which the solution is mixed in the dispersion or the solution in which the resin is dissolved in a solvent is mixed with the dispersion, and the slurry is dissolved and knives are dispersed as described in the above patent. Polyoxyalkyleneethylphosphoric acid, polyoxyethylene ethyl carboxylate (Patent Document 201226049 1). It is used to make metal particles, metal oxides, pigments, various fillers easy. The technique of re-dispersing in a dispersion medium and a resin, and having been coated with a surface modifying agent and a surface protecting agent to disperse the particles, or to immerse the surface modifying agent or the like in the dispersed particles, has been used, but the prior art Often limited by the type of dispersing medium and the amount of dispersing material added, the scope of use is extremely limited, and % have not found dispersing agents or surface modifiers and surface materials which can solve this problem. If it is found that the dissolving agent can be solved (4) " That is, a dispersing agent which has/supplements to a wide range of materials without the limitation of the kind of the dispersing medium and the amount of dispersing substances, and obtains a non-aqueous component using the dispersing agent and a surface which uses the dispersing agent as a dispersing substance. a modifier or a surface protecting agent for coating a powder or impregnating the dispersing agent into a powdery, granular or paste-like substance, which is mixed with a resin or a resin solution in a solvent replacement and a polarity change. In view of the above, 'industrial use value is extremely large. For example, as such a prior art, Patent Document 2 discloses that a metal steroid particle 'a system' consists of metal nanoparticles (A) and covers the gold. The protective colloid (B) of the nanoparticle (A) is composed of the protective colloid (8) composed of an organic compound (B1) having an octacarboxy group and a polymer dispersant (7) 2). Further, 'the application is not disclosed at the time of application.曰 曰 曰 ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ G A wide range of dispersoids' and a small amount of added can exert excellent dispersion stability. However, it is expected to develop a dispersant which can disperse a larger amount of dispersoids such as inorganic fine particles and fillers. 201226049 [Previous Technical Paper [Patent Document] Patent Document 1: Japanese Laid-Open Patent Publication No. 2004-354568 (Patent Document 2) Japanese Patent Application Publication No. Hei No. Hei. No. Hei. The polyoxyalkyleneethylphosphoric acid and the polyoxyalkylene carbazate may sometimes fail to obtain the desired dispersibility due to the electrical contact of the inorganic fine particles or the filler with the resin. For example, a dispersion prepared from a combination of a polyoxyalkylene decanoic acid and an aromatic versatile photocurable resin material, that is, a phenoxy acetoacetate (PHE), can be remarkably Loss of transparency was observed, and a decrease in dispersibility was observed. For this reason, it is required to disperse the inorganic fine particles in various resins. The present invention has been developed in the light of the problems of the prior art: it is intended to provide a dispersing agent for dispersing media which can be applied to a wide range of dispersing substances, and can exhibit excellent dispersion stability by adding a small amount. It is suitable for dispersing a large amount of dispersoids. Further, it is an object of the present invention to provide a dispersion composition which is obtained by using the dispersant. Further, it is an object of the present invention to provide an organic particle or an inorganic particle which is coated with the dispersing agent or impregnated with the dispersing agent. [Technical means for solving the problem] 201226049 In order to achieve the above object, the dispersing agent of the present invention is composed of the compounds shown by the following formula:

II (1)

R — X—^AO^· Y — C —OH However, R of the formula (1) represents a fluorenyl group containing at least one eight-membered scented ring, and A0 of the formula (1) represents an oxygen having a carbon number of 1 to 4. Hole 1 is a sinking group, η represents the average addition mole number of the epoxy burn and is a value in the range of 丨 to ", X of the formula is 0 atom, S atom, -NR^Ri is a ruthenium atom or by c The hydrazine of the formula (1) which is composed of any one of the atom, the argon atom, the genus, and the genus of the genus, is a conjugate group composed of any of C, H, and 0 atoms. Here, R of the formula (1) is a styrene phenyl group represented by the following formula (2), preferably k3Η (2) k However, k of the formula (2) is an average value and is in the range of i to 5. Further, Y of the formula (1) is preferably an alkyl group having 1 to 15 carbon atoms or a functional group represented by the following formula (3). Ο (3)

II

—C— Z 201226049 However, Z of the formula (3) is any one selected from the group consisting of an alkyl group having a carbon number of 丨 to 丨$, a phenyl group and a phenyl group having a carboxyl group. The inorganic particles ' of the present invention are coated with either of the above dispersing agents or impregnated with the dispersing agent. Further, the dispersion composition which is not known is obtained by dispersing inorganic particles in a non-aqueous dispersion medium using any of the above dispersants. Further, the coating composition of the present invention contains the above-described dispersion composition. The sub-fourth composition is a non-aqueous dispersion medium using a resin. Further, the coating composition of the present invention comprises a mixture of the above dispersion composition and a resin, and the dispersion composition uses a solvent as a non-aqueous dispersion medium. The coating composition is applied to the member of the present invention by subjecting any of the above substrates to a reaction. [Embodiment] [Preferred Embodiment of the Invention] The dispersant of the present invention is contained in the formula (1), and is composed of the following components. , having a scent of at least one aromatic fragrant, and a dispersion of the ... furnace ... part of the system is composed of an oxygen-extension base and a sulfhydryl group, wherein the private part of the position is # AY media affinity The sexual site and the dispersing affinity site are linked by a linking group, an alpha group X. Below, the β Α form. Illustrative Embodiments of the Invention 1. Hydrophobic Group (R) 201226049 In the hydrophobic group (R) which can be used in the dispersant of the present invention, r is a hydrocarbon group containing at least one aromatic ring. Specifically, in addition to the styrenated phenyl group which is not represented by the above formula (;), for example, a functional group including the following group, an octylphenyl group, a nonylphenyl group, a cumylphenylene group may be mentioned. Styrene phenyl, p-phenyl phenyl, and the like. Further, for example, a functional group containing a polycyclic aromatic hydrocarbon such as naphthalene, anthracene, benzQpyran, chrysene, t (c〇r〇nene), or a bowl of thin ( C〇rannuiene), thick tetraphenyl, piperazine, benzophenanthrene (8) phenylene#. Further, in the present case, for example, Tsai is considered to contain two aromatic rings, and the tether is considered to contain three aromatic rings. In the dispersant of the present invention, the musk ring contributes considerably to the improvement of dispersibility. For the purpose of the present invention, a compound containing the present ethoxylated phenyl group represented by the formula (7) can be preferably used. 2. Linker (X) The linker (X) is a linker composed of any of a ruthenium atom, an S atom, and _NR, and R is a ruthenium atom or a C atom or a H atom. A functional group composed of any of the atoms. R! may be, for example, a saturated linear group having a carbon number of i to 18 such as n-hexyl or n-octyl group; a saturated branched alkyl group having a carbon number of 1 to 18 such as 2-ethylhexyl or isodecyl; An unsaturated long-chain alkyl group such as Hn〇leyl, nn〇ienyl, oleyl, coconut alkyl, tallow alkyl or hardened tallow alkyl. 3. Oxyalkylene (AO) n The preferred class of alkylene oxide in the dispersant of the present invention, in the formula (1), 'AO means the carbon number is! To the oxygen alkyl group of 4, specifically, the epoxy oxime of carbon number 2 is epoxy epoxide. Carbon number 3 is burned to epoxy propylene. "Charcoal number 12 201226049 4% oxane is tetrahydrofuran or cyclohexane bromide 4 coat butane to 込2-% oxybutane or 2,3- ((A 〇;;-...In the dispersant of Ming, the oxygen-expanding-based bond oxygen VJt has the purpose of adjusting the dispersing agent affinity of the dispersant, and the ring =;: Γ chain 'or two or more kinds of epoxy' random polymerization The average addition of the burned molars is η, and the range of the epoxy represented by ί(1) is preferably 隹·3 to Sichuan 4. The linking group (Υ) 2 group 00 can be composed of carbon atoms, hydrogen atoms, and oxygen atoms. In the t structure, it is selected that 'the composition of the remaining nicotine, unsaturated hydrocarbon group, sulfhydryl group, ruthenium group, and Sg group' may have an alicyclic structure, an aromatic ring structure, and also two (four) complex single heart The linking group "containing a gas atom and/or a sulfur atom and a % atom or the like" is not suitable as a structural factor of the dispersing agent of the present invention because it has an affinity effect of a reducing group on a dispersing substance. Further, the formula (_Y) Preferably, the alkyl group having a carbon number of 1 to 15 is preferably an alkyl group having a carbon number of 1 to 8. The oxime of the formula (1) is preferably a substance represented by the above formula (3). In the formula (3), hydrazine is selected from the group consisting of a stretching group having a carbon number of 5, a stretching group, a stretching phenyl group, and a carboxyl group-containing phenyl group. 5. Dispersing the particles from the source It is selected from the particles of the dispersed particle material dispersed by the dispersant of the present invention and/or the particles derived from the organic substance. Aluminum, chromium, nickel, for example, particles derived from inorganic substances can be used: iron, zinc, tungsten indium Tin 'Ji, wrong, Chin, copper, silver, gold, turn, etc. 13 201226049 and the alloy of the special; or the broken stem + human 岚 * work 4 of this compound. At this time, 4 will be the aforementioned gold ^ nt Bottom-side Baoyuan agent is covered: alkane oximes and fatty acids, hydroxycarboxylic acid-forming #*上△ Fangxiang carboxylic acids, dilute bases, thiols, sputum, drunk chewing phenol, biologicals, and parents The carrier polymer, 咼 molecular surfactant, 侗 工 工 w, low knife interface surfactant, etc. Others: kaolin, clay, talc, mica, bentonite, dolomite, Shixi acid office, Shixi acid lock , asbestos, calcium carbonate, magnesium carbonate, barium carbonate, calcium sulfate 'sulfate lock, sulfuric acid, hydrogen peroxide, iron hydroxide, materials, Oxidation error, oxidized money, alumina, titanium oxide, iron oxide, zinc oxide, antimony trioxide 'indium oxide, copper oxide tin, carbon cut, nitrogen cut, nitrided shed, barium titanate, rare earth, carbon" ', graphite, asbestos, glass wool, glass fiber, carbon fiber, carbon nanofiber, carbon nanotube (single-walled nanotube, double-walled nanotube, multi-walled nanotube), etc. In addition, derived from organic matter The particles are: azo, diazo, condensed azo, sulphur, indanthrone, 啥α丫, quinacrid〇ne, 蒽醌-benzimidazole Organic pigments such as ketone, perylene, anphthalapyridine, di〇xazine, etc.; polyethylene resin, polypropylene resin, polyester resin, nylon resin, poly Amidoxime resin, aromatic polyamide resin, acrylic resin, vynyon resin, urethane resin, melamine resin, polystyrene resin, polylactic acid, acetate fiber, cellulose, semi-fiber , lignin, chitin, chitosan, starch, Acetylene, aromatic polyamine-resin, polycarbonate, polyphenylene ether, polyetheretherketone, polyetherketone, polybutylene terephthalate, polyethylene naphthalate, polybutylene naphthalate Second S, poly sul fone, polyphenylene sulfide, polyimine, and the like. 14 201226049 The above-mentioned dispersed particle "dispersed by a sputum or sputum agent" may be a crystal chew, and the above-mentioned displacing particles dispersed in the dispersing agent of the present invention, oxygen-permeable particles or anisotropic particles may also be fibers. shape. In the middle of the month, as the dispersion medium, the above-mentioned dispersed particles can be obtained by using the method. There are two methods for preparing the fine particles: the coarse particles are mechanically ground and miniaturized. Top-down causes several unit particles to be generated and the agglomerates are formed by the particles. The bottom-up (b〇ttGm-up) method of forming particles can be preferably prepared by any method. Further, these can be modulated by any method of wet method or dry method. In addition, the bottom-up method has a physical method, but can be modulated by any method. The knife of the present invention can be used for mechanically grinding and miniaturizing coarse particles. The following steps can be used to form a particle in a clustered state in which a plurality of unit particles are formed and agglomerated by the particles to form a particle in a bottom-up manner: 'or use the following particles: 胄Firstly, the particles are removed by the above method, and the particles are removed after the microparticles are used to remove the dispersed particles from the medium and are used as a surface modifying agent or a surface protecting agent. The aforementioned conventional dispersing agent is used instead of In order to more specifically describe the bottom-up mode, the preparation method of the metal nanoparticles in the above-mentioned dispersed particles is exemplified. From the bottom-up manner +, the physical side, representative examples are: making a bulk metal in an inert gas Evaporating in a medium and condensing it by collision with a gas to generate a vaporization method in a gas of a nanoparticle. Further, the chemical method includes: reducing a metal ion in the presence of a protective agent in a liquid phase, and then The produced valence metal is stabilized by nanometer size 15 201226049 liquid phase reduction method; and thermal decomposition method of metal complex compound, etc. Liquid phase reduction method can be utilized: chemical reduction method, electrochemical reduction*, photoreduction method, Or a method of combining a chemical reduction method with a light irradiation method, etc. Further, the dispersion medium which can be preferably used in the present invention can be obtained by any of the methods of the top-down manner and the bottom-up manner as described above. These may be prepared in any of an aqueous system, a non-aqueous system, or a gas phase. 6. Dispersing Medium The dispersing medium which can be used in the present invention may, for example, be toluene, xylene, a square aromatic hydrocarbon solvent, or the like. , aid p_. m a hydrocarbon-based solvent such as % hexane or n-heptane; - a halogenated hydrocarbon solvent such as chloroform or chloroform; diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran, Dibutyl ether, butyl ethyl ether, μ tertiary n terpinyl methyi ether, dihydroterpine methyl ether, diethylene glycol diglyme, hydrazine晨晨(di〇x〇lane) 荨趟 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, acetonyl acetone, isophorone, cyclohexanone, methylcyclohexanone, 2_(1_cyclohexenyl)cyclohexanone, A Ketone solvents such as isobutyl ketone, cyclohexanone and isophorone; ethyl decanoate, propyl citrate, butyl formate, isobutyl formate, amyl citrate, methyl acetate, ethyl acetate , n-propyl acetate, isopropyl acetate, n-butyl acetate, isobutyl acetate, butyl acetate, isoamyl acetate, cyclohexyl acetate, acetaminophen, 3-methoxybutyl acetate Ester, secondary hexyl acetate 2-ethylbutyl acetate, 2-ethylhexyl acetate, phenyl decyl acetate, methyl propionate, ethyl propionate, decyl chloroacetate, ethyl chloroacetate, butyl acetate, acetonitrile Ethyl ester, B 16 201226049 Ethyl acetate, propionate; Ethylene glycol monoethyl ether, Ethyl acetate, γ_Τ internal material, Ether ether, Diethylene glycol monoethyl ether, Dibuyiyiyi Early butyl methyl ether, propylene glycol mono-alcohol early n-butyl ether, propylene glycol mono-saponin ethyl ether, and _. Butyl butyl ether, dipropylene glycol mono-|propyl ether, propylene glycol mono-alcohol mono-n-methyl ether, dipropylene glycol monoethyl ether $ s? early n-propyl ether 'two soil 飐 Μ Μ, - / ^ Alcohol early n-butyl hydrazine, triethylene glycol monomethyl isopropyl ether, diethylene glycol monoethyl ether, _ 転 転 基 « « — G — alcohol mono-propenyl M, - r early n-butyl sulphate, tripropylene glycol oxime Diethylene glycol tripropylene glycol mono-n-butyl ether dipropylene glycol mono-n-propyl ether, early butyl ether-polyglycol ether solvent ester solvent; diethylene glycol _ ~ and other early detection of ethylene glycol Among them, a dialkyl ether solvent such as an alcohol diethyl fluorene, an alcohol methyl isobutyl hydrazine or a dipropylene glycol di-ethyl ether. The earth-and-propylene glycol may, for example, be, for example, methyl n-butanol, isobutanol, secondary butanol, n-propanol, isopropanol, secondary sterol, n-hexanol, tetrahydroanthracene, butanol , heptanol, n-pentanol, octyldodecanol, "ethyl propanol," A: propanol, gaseous ethanol, tertiary pentanol, secondary isoamyl alcohol, neopentyl butanol, sterol, Heptanol, n-octanol 2-methylpentanol, deca-alkanol, lauryl alcohol, cyclopentanol, decyl alcohol, decyl alcohol, fen. Tian 1 (terpine〇1), terpineol C, L-a_terpineol, bis-'terpineol-based ethanol, dihydroterpineol oxyethanol, and taitai^' made of alcohol, pine oil company Tersorb MTPH, T 'ene Chemicals Limited

Ters〇rb DTO-210 . τ. u THA-9〇.TersorbTHA.7〇^jt^ 3 _ Ters〇rb Acebutol such as acetol, 1,4-butanediol, octanediol, etc. Nissan Chemical Industry Co., Ltd. 17 201226049 Company's FINEOXOCOL 140N, FINEOXOCOL 1600, FINEOXOCOL 180, FINEOXOCOL 180N, FINEOX〇c〇l 2000 and other alcohol solvents, ethylene glycol 'diethylene glycol, triethylene glycol, propylene glycol, A glycol-based solvent such as dipropylene glycol, 1,3-butanediol, hexanediol, polyethylene glycol, or polypropylene glycol. Further, for example, a guanamine-based solvent such as dimercaptoacetamide or dimercaptocarbamide may be mentioned. Further, as the dispersion medium, ethylene such as a (meth)acrylic acid, a (meth)acrylic acid ester or a vinyl monomer such as vinyl acetate, a vinyl ether derivative or a polyallyl derivative may be used. Is an unsaturated monomer. Others may be used without any particular limitation: various types of resins, polymerized materials, and monomers used for coating, bonding, and molding. Specific examples thereof include an acrylic resin, a polyester resin, an alkyd resin, an amine ester resin, a silicone resin, a fluororesin, an epoxy resin, a polycarbonate resin, a polyethylene resin, and a polyethylene. Alcohol, etc. Further, the above-mentioned dispersion medium may be used singly or in combination of two or more kinds as appropriate. Furthermore, the purpose of the dispersing agent of the present invention is to provide a dispersion of microparticles in a non-aqueous environment, but for the above-mentioned dispersing medium, either intentionally or accidentally, in the manufacturing step of the microparticle dispersion, or for the intended use, or When designing the final product, there is no denying that water will mix in and mix. 7. The other dispersant of the present invention can be produced by a known method, and the type of the hydrophobic group, the type of the alkylene oxide and the addition form thereof, the amount of the added molar amount, the linking group, and the like are specifically defined within the above range. To choose the most suitable group: and in the comparison with the conventional dispersing agent 'can make a wider variety of butterflies> disperse dispersion, can be 201226049 to make the dispersion in a wider variety of scattered sister VIII eight knife joyful dispersion In terms of the point of view, the value of utilization in the industry is quite large. Further, the dispersing agent of the present invention can be used by reducing the content of the ionic species contained by the conventional refining method, and specifically, the content of each ion of the metal ion, the soil metal ion 'heavy metal ion, and the i element ion. The ionic species in the dispersant, due to dispersion stability to the dispersion, recording resistance, oxidation resistance, electrical properties of the dispersed coating film (conductive properties, insulating properties), stability over time, heat resistance, low humidity, weather resistance The content of the above ions may be appropriately determined, but it is preferably determined in the dispersant. In the present invention, the content of the dispersant preferably used is such that the dispersing amount can be made in the non-aqueous dispersion medium. The sentence dispersion '% is not particularly limited, although it varies depending on the use, etc.', but the entire dispersion composition is 1% by weight, preferably in the range of 0.1 to 20% by weight, and the content of the dispersed particles is 】 ~90 weight $% range is better. Further, the content of the dispersing agent is preferably in the range of 300 mg with respect to the dispersed particles. The content of the dispersion medium is such that the total amount of the dispersion and the composition is 1 () (% by weight), which is preferably within the weight range. The average particle diameter of the dispersed particles is preferably in the range of (4) nm, preferably in the range of 1 G to (10). The dispersant ' of the present invention can be produced by a known method. It can be produced by the following method: For example, a nonionic surfactant compound obtained by adding an alkylene oxide to an alcohol, an amine or a mercaptan is used as a raw material, and a simplex m is used. a method in which an acid or a salt thereof is subjected to a ring-forming reaction with an epoxy-fired terminal in the presence of a test, or a method of performing a ring-opening reaction with a hydroxyl group at the terminal of an epoxy compound by using an acid anhydride, but is not limited thereto. method. 201226049 Further, the dispersion composition of the present invention can be prepared by a homogenization means or a dispersing means using a conventional hand-mixing means. Examples of the dispersing machine that can be used include, for example, a roll mill such as a 2-roll or a 3-roll mill, a ball mill, a ball mill for a vibrating ball mill, a paint shaker, and a continuous disc type bead mill. Such as bead mill, sand mixer, jet mill, etc. In addition, dispersion treatment can also be carried out in an ultrasonic generation bath. Further, the dispersant of the present invention not only stabilizes the dispersion of the dispersed particles in the non-aqueous dispersion medium, but also exerts a superior sub-government stabilization effect than the conventional technique' and can also serve as a dispersion-dispersing particle. Use a protective agent that is removed from the media. The function of the protective agent for removing the dispersed particles from the medium in a stable manner is, for example, inhibition of aggregation of the generated particles, inhibition of adsorption on the wall surface of the container, prevention of contamination, and prevention of oxidation of the metal particles by easy redispersibility. The surface modification of the particle surface, the deterioration of the functional surface, the relaxation of the solvent and the change of the polarity, the improvement of the fluidity of the powder, and the prevention of the curing of the powder. The dispersant of the present invention is more excellent than the conventional protective agent, and the desired dispersion can be achieved by selecting the optimum addition form of the alkylene oxide, the amount of addition molybdenum, the type of the hydrophobic group, and the linking group. The quality is dispersed and stabilized in a dispersion medium which is more widely known than a protective agent. a substrate to which a coating composition comprising the dispersion composition of the present invention is applied and which is used as a non-aqueous dispersion medium, or a dispersion composition comprising the present invention and a resin The coating composition of the mixture and the dispersion composition use a solvent as a non-aqueous dispersion medium; for example, a glass, a resin film, a glass composite 20 201226049 material, a ceramic, a metal/steel plate, or the like can be used. According to the present invention, it is possible to provide a dispersion composition which can disperse inorganic fine particles or fillers in a dispersion medium and which has high transparency and stability. The dispersion medium is difficult to disperse by a conventional dispersant. Further, a dispersing agent can be provided which is capable of stably dispersing a large amount of dispersoids by adding a small amount. Further, a dispersion composition can be provided which is formed using the dispersant and which can provide a coating composition which contains the dispersion composition. [Examples] Examples and comparative examples of the present invention will be described below. In addition, the following indicates the "parts" of the blending amount, which means "parts by weight", and "%" means "weight %". Of course, the present invention is not limited to the following embodiments, and may be appropriately modified and modified without departing from the technical scope of the present invention. <Synthesis of Dispersant> [Production Example (Synthesis of Stupidated Vinyl Phenol (k = 3) Ethylene Oxide 8 mol Adduct)] In a autoclave, styrene phenol (k = 3) 415 g was placed. (lm〇1), potassium hydroxide lg (0.018 mol)' and mixed until homogeneous. Then, 352 g (8 mol) of ethylene bromide was added dropwise to the reaction system under the condition that the reaction system had a star rating of 130 °C. After the completion of the dropwise addition of ethylene oxide, at this temperature, the pressure was maintained at 0.1 MPa, and the mixture was aged for 1 hour to obtain an ethylene phenol 8EO (Ethylene Oxide 'ethylene oxide) adduct. [Production Example 2 (Synthesis of 14 mol of an ethylene epoxide (k=3) epoxy Ethylene bake product)] 21 201226049 In addition to the production example, the amount of ethylene oxide added was changed to 616 g (14 m). 〇l), the rest with the manufacturing example! The same method was carried out, « while obtaining a phenylethylated phenol 14EO adduct. _ [Production Example 3 (Synthesis of Dispersant 1)] In a toluene solvent, a styrenated phenol (k=3) ethylene oxide 8 mol hydrazine adduct 767 obtained in Production Example was added to a reactor ( Lm〇1) and sodium chloroacetate 152g (1.3m〇l)' and stirred to be uniform. Then, 52 g of sodium hydroxide (i 3 m〇i) was added under the conditions of a reaction system temperature of 60 C, and then the temperature of the reaction system was raised to 8 (TC 'make it for 3 hours. After the ripening, it was cooled to 50 C, and 117 g (1.2 m 〇l) of 98% sulfuric acid was added dropwise at 50 ° C to obtain a white suspension solution. Then, the white suspension solution was washed by using distilled water and the solvent was distilled off under reduced pressure. The dispersant 1 described in Example 1 (R: styrenated leather (k=3), AO: epoxy epoxide, 11:8, y: y, y: (: 112;) was obtained. [Production Example 4 (Synthesis of Dispersant of Example 2)] In the production example 3, a styrene-substituted phenol (k=3) ethylene oxide 14 mol adduct 10 g (1 mol) was used instead of styrene. The same procedure as in Production Example 1 was carried out except that the phenol (k = 3) ethylene oxide 8 mol addition product was obtained, and the dispersant described in Example 2 was obtained (R: styrenated stupid. k = 3), AO: Ethylene bromide, η: 14, Χ: 〇, γ: CH2). [Production Example 5 (Synthesis of Dispersant of Example 3)] Styrene-forming phenol at 120 ° C (k=2) Ethylene oxide 8 mol of the adduct 654 g (1 mol) and succinic anhydride l〇〇g (im〇i) were reacted for 2 hours to obtain the dispersing agent described in Example 3 (R: styrenated phenyl group (k== 2), AO : 22 201226049 Ethylene oxide, 11:8, again: 〇, 丫: (: 112 € 112 (: 112). [Manufacturing Example 6 (Synthesis of Dispersant of Example 4)] Except in Production Example 3 'Use of 654 g (1 mol) of 8 mol of adduct of styrene (k = 2) ethylene oxide, and substituted 8 mol of adduct of styrenated phenol (k = 3) ethylene oxide. 1) The dispersant 4 described in Example 4 was obtained by the same method (R: phenylethylated phenyl (k=2), AO: ethylene oxide, η: 8, X: 〇, Y [Production Example 7 (Synthesis of Dispersant of Comparative Example 1)] In addition to the use of the isotridecyl alcohol oxide 丨〇m〇1 adduct 640 g (1 mol) in Production Example 3, In the same manner as in Production Example 3 except that the styrene phenol (k==3) ethylene oxide 8 mol adduct was used as the raw material E 〇 adduct, the results described in Comparative Example 1 were obtained. Dispersant (R: isotridecyl, AO: ethylene oxide) η : 1 〇, X : 〇, γ : CH2). Further, each of the materials shown in the above, and the materials used in the examples and the comparative examples are all commercially available materials. Preparation of Oxidized Dissolved Acrylate Monomer Dispersion> Commercially available oxidative dispersion (trade name SZR-M' manufactured by Seiko Chemical Co., Ltd., primary particle size 3 nm, containing 3% by weight of sterol dispersion) 1 part of the dispersant shown in Table 1 below, and phenoxy acrylate acrylate (trade name new FRONTIER PHE, manufactured by Daiichi Kogyo Co., Ltd.) or phenylthioethyl acrylate (DAELIN) Manufactured by Chemical Co. Ltd., trade name: Electromer HRI-01) or 28.5 parts of o-phenylphenoxyethyl acrylate and 12 parts of 3-methoxyl-3 methylbutanol, and mixed, using a rotary evaporator The methanol was removed under reduced pressure to obtain a cerium oxide acrylate single 23 201226049 bulk dispersion. Acrylic acid phenoxy phenoxyacetate is prepared as a dispersion using commercially available materials.

T. <Evaluation of Characteristics of Dispersion> a. Transparency of Appearance The acrylate monomer dispersion of zirconia was placed in a transparent glass container, and the letters printed in the 12th letter were placed under the above container. After the paper, the transparency of the dispersion was evaluated by recognizing the letter across the dispersion. The evaluation criteria are as follows. 〇 After the dispersion was added to a lcm deep glass container, the letter of the 12th letter was clearly observed. The dispersion is transparent. X. After the dispersion was added to a glass container of A lcm depth, the letter of the 12th word could not be clearly observed. The dispersion was cloudy. The results are as shown in Table 1. The viscosity of the β b. dispersion was evaluated for the viscosity of the acrylate monomer dispersion having good dispersibility, and an E-type viscometer (trade name re_8〇r manufactured by Toki Sangyo Co., Ltd.) was used. The measurement was carried out at 25 °C. The results are shown together in Table 1. c. Evaluation of the refractive index of the dispersion' The refractive index of the dispersion of the acrylate monomer having good dispersibility was measured using an Abbe refractive index measuring machine (trade name NAR-1T, manufactured by ATAG Co., Ltd.) at 25 ° C. The measurement was carried out. The results are shown together in Table t. 24 201226049 [Table i] Dispersant Structure (RX-(AO)nYQ) Monomer Subscript Body Characteristics (R) AO Surface AO Average Force Number (π) Linkage (X) Linkage (Y) (Q) Recording Viscosity (mPa.sec) Refractive Index Miscellaneous 1 Phenylethylene (k=3)*1} Ethylene Ethylene 8 〇03⁄4 COOH Cingxiang Treading Ethyl Ester 6400 1.611 Pour 2 Stupid Ethylene >(t» (k=3)*I} Ethylene Ethylene 14 0 (3⁄4 COOH propyl; Ethyl Ester 〇16910 1.607 丨 J3 phenylethylene (k=2)*1} Epoxy 8 0 OCHiH 2 C00H 154 mesh 〇 〇 600 600 600 600 600 600 600 600 600 600 600 600 600 600 600 600 600 600 600 600 600 600 600 600 600 600 600 600 600 600 600 600 600 0 0 0 0 0 0 0 0 0 0 0 0 0 480 480 480 480 480 480 480 480 480 480 480 480 480 480 COOH 甲纲〇〇1410 1.638 Case 6 styrene (4))*1) Ethylene bromide 8 0 (3⁄4 COOH propyl mm ethyl ester 〇60000 1.645 isotrifluoroethylene bromide 10 0 (3⁄4 COOH propyl; oxygen Ethyl ethyl ester X cannot be evaluated. Cannot be evaluated. Column 2 Isotrixe Ethylene 10 0 (3⁄4 COOH Μ·Ethyl X can not be evaluated cannot be evaluated (column 3 different thirteen epoxy bakes 10 0 (3⁄4 COOH propyl mm base B) Ester X can not be assessed for shame evaluation tb^J4 styrene 〇 c= 2)*]) Ethylene oxide 10 0 (3⁄4 COONa Ethyl Ester X can not be evaluated cannot be evaluated _ to 5 Phenylethylene (k=2f) Epoxy 8 8 ch2 OH Bingxiang sister ethyl ester X cannot be evaluated Unable to evaluate the t-column 6 Lauryl Ethylene Ethylene 4 0 (3⁄4 COONa Ester Ethyl X cannot be evaluated 无法1) The styrenated phenyl material is a benzene obtained by introducing k styrene monomers into phenol. Ethylene phenol. 25 201226049 From the table, it can be seen that Example 6 uses a dispersing agent in which a hydrophobic group contains an aromatic ring and a terminal group is a carboxylic acid, and is excellent in dispersing matter containing an aromatic acid vinegar monomer. When the amount of the dispersant is the same as that of the examples 1 to 6 in the case where the hydrophobic group does not contain the aromatic ring, the dispersibility is poor, and even if it is hydrophobic, The base contains an aromatic ring, and when it is a sodium salt of the terminal group, it is a comparative example 4, or the terminal group is an alcohol, and the dispersibility of the solvent is rather poor. , the ring of the ring and the carboxylic acid system of the terminal group play an important role in dispersibilityIn the dispersions shown in Examples 1 to 6, the combination of the dispersant and the acrylic acid acrylate monomer type was as low as 1400 to 4000 mPa·sec in the absence of the diluent solvent. If the viscosity of the dispersion is low, it is easy to apply to the substrate, so it is industrially valuable. Further, the dispersions of the dispersions shown in Examples 1 to 6 have a refractive index of 16 to 1 645, respectively, which is more improved than the original acrylate monomer type, and the dispersion composition is obtained by using the dispersant of the present invention and zirconia. Then, using the dispersion composition ', a dispersion composition excellent in transparency and high refractive index and a coating material can be provided. The dispersion composition of the present invention can be used in the following fields: a hybrid material, a surface protective agent, a conductive paste, a conductive ink, a sensor, a precision separation element, a light sigma, a liquid crystal display element, and a nematic Rice magnet, heat transfer medium, functional catalyst for fuel cell, organic solar cell, nano glass element, abrasive, drug carrier, environmental catalyst, paint, printing ink, ink for inkjet, resist for color filter Ink, optical film, adhesive 26 201226049 agent, anti-reflection film, hard coating film, etc. ^ The monthly dispersant can effectively make the product in the description and its manufacturing steps more in .β ώ , Λ τ τ as the main component of the nanometer size: from inorganic or organic-derived isotropic materials and / or anisotropic material is dispersed and stabilized in a non-aqueous dispersion medium, and inhibits agglomeration of dispersoids in the dispersion medium to achieve long-term dispersion stabilization to obtain desired product characteristics, processing characteristics, quality stability, and productivity improvement. . The present invention has been described in detail and with reference to the specific embodiments of the present invention, and various modifications and changes can be made without departing from the spirit and scope of the invention. Easy to know. The present application is based on Japanese Patent Application No. 2010-28648, filed on Dec. 22, 2010, which is incorporated herein by reference. [Simple description of the diagram] None [Key component symbol description] None 27

Claims (1)

201226049 VII. Patent application scope: A kind of dispersing agent' is composed of the compound of the formula (1): Ο II R —X Αθ γ — C —OH —— · (1) However, R of the formula (1) Contain at least! More than one aromatic ring of smog, AO of formula (1) represents an oxygen (tetra) group having a carbon number of i to 4, and ^ represents an average addition mole number of alkylene oxide and is a value in the range of 1 to 3 Å. X in the formula (1) is a linking group composed of any one of a ruthenium atom, an s atom, and NR1_ (wherein R1 is a ruthenium atom or a group consisting of a C atom, a ruthenium atom or a ruthenium atom), The Υ of 1) is a linking group composed of any one of λ χ 0 atoms. 2. The dispersant according to claim 1, wherein R\ of the formula (1) is a benzene group represented by the following formula (2), Or CI Η Ί 3 , -ό (2) k value but 疋 ( 2) k is the average value, and is the number of the range from i to $. 3. As claimed in the first item of the patent scope, +. , ^ .. 'dispersant, where . (1) Y is a C 1 to a non-15 alkyl group, or a functional group of the following formula (3) 28 201226049, Ο II λ — ό — ζ — (3) However, the enthalpy of the formula (3) is a carbon number Any one selected from the group consisting of a stretching group of J to 15, a vinyl group, a phenyl group, and a phenyl group having a carboxyl group. 4. An inorganic particle obtained by coating a dispersing agent according to any one of the above-mentioned claims to the third aspect or impregnating the dispersing agent. A dispersion composition obtained by dispersing inorganic particles in a non-aqueous dispersion medium using the dispersant according to any one of the above-mentioned items. A 6' coating composition comprising: the dispersion composition described in claim 5, wherein the dispersion composition uses a resin as a non-aqueous dispersion medium. A coating composition comprising: a mixture of a dispersion composition and a resin as described in claim 5, wherein the dispersion composition uses a solvent as a non-aqueous dispersion medium. A member obtained by applying the coating composition described in claim 6 or 7 to a substrate, and then reacting the composition. 29 201226049 IV. Designated representative map: (1) The representative representative of the case is: None. (2) A brief description of the symbol of the representative figure: None. 5. If there is a chemical formula in this case, please disclose the chemical formula that best shows the characteristics of the invention: