TW201141602A - Dispersant and dispersion composition - Google Patents

Abstract

Provided is a dispersant for non-aqueous dispersion media that can be used for a broad range of substances to be dispersed and which can exhibit excellent dispersion stability with small amounts added. The dispersant for non-aqueous dispersion media comprises a compound represented by Formula (1). R in Formula (1) represents a C1 to C24 alkyl group and/or alkenyl group that comprises an alkyl group and/or alkenyl group with a branched chain. AO in Formula (1) represents a C1 to C4 oxyalkylene group. n represents the mean number of moles of alkylene oxide added and is in the range of 1 to 30. X in Formula (1) is a connecting group comprising carbon atoms, hydrogen atoms and/or oxygen atoms.

Description

[Technical Field] The present invention relates to a dispersant and a dispersion composition using the dispersant. [Prior Art] An isotropic material derived from an inorganic substance or an organic substance and/or an anisotropic material is used as a host material in the following fields of use: a mixed material 'surface protectant, conductive paste, conductive ink, Sensor, precision analysis component, light δ recall, liquid crystal display component, nano magnet, heat transfer medium, fuel cell catalyst, organic solar cell, nano glass component, abrasive i carrier, environmental touch Medium, paint, printing ink, ink for inkjet, resist for color filter, ink for writing tools, etc. In this case, the above-mentioned inorganic material or organic-derived isotropic material and/or anisotropic material is used as an inorganic dispersion medium (aqueous dispersion medium) or a non-aqueous dispersion medium (non-aqueous dispersion medium). By modulating the dispersion and utilizing it, it is industrially utilized as a substance which is effective in stabilizing the quality and improving the yield at the time of manufacture as an efficient shake, treading property, product property, and material property. And shape: the two sides 'targeted by the change of the material of the dispersive material, the miniaturization of the particle size and the shape control, and the difficulty of the production of eight batches of disaster-stricken knives, decentralized and scattered in the knife media Condensation coke will occur in a short time, π t, Μ. Station disperse 2 will not only lead to reduced productivity, reduced processing characteristics, reduced handleability and reduced yield when manufacturing dispersions, the final product of the knife System 201141602 The material properties and quality of the characteristic materials are reduced. Others, it is known that appearance, such as transparency, gloss, reduction in coloring power, color separation, and occurrence of cracking # are not good. In order to suppress such dispersive agglomeration to achieve dispersion stabilization, a dispersant is used. As a proposed low molecular weight dispersant, an organic sigma having a carboxyl group, for example, except for formic acid, acetic acid, propionic acid, butyric acid, caproic acid, heptanoic acid, acid, citric acid, citric acid, undecanoic acid. , lauric acid, myristic acid, palm scorpion succinic acid, oleic acid, linoleic acid, linoleic acid, etc., saturated and unsaturated carboxylic acids with carbon number i~2〇, hydroxycarboxylic acid, carbon The number 6 to the month of the % family, aromatic carboxylic acids and the like. Examples of the alkenyl succinic anhydrides include octene succinic anhydride, undecyl succinic anhydride, and hexadecenyl succinic anhydride. Organic compounds having a thiol group, for example, are: ethanol, thiol propanol 1, sulfhydryl-2,3-propanediol, 3-mercaptopropyltrimethoxydecane, decyl amber oxime, hexylmercaptan, pentane disulfide A mercaptan such as an alcohol, dodecanethiol, undecyl mercaptan or decyl mercaptan. The organic compound having a desired ring is, for example, triphenylphosphine, tributylphosphine, trioctylphosphine, tributylphosphine or the like. An organic compound having an amine group, for example, propylamine, butylamine, hexylamine, heptylamine, octylamine, 2·ethylhexylamine, decylamine, decylamine, dodecanamine, hexadecylamine, oleylamine ( Oleylamine) and so on. In addition, the 'high molecular weight dispersant' is mainly developed as a dispersing agent for pigments and the like, and a polymer type dispersing agent having a skeleton such as a slow group, an amine group, a trans group, a self-linking member, a guanamine bond or an aromatic heterocyclic ring. It has been transferred to this application and is commercially available as: Dlsp manufactured by Byk Chemie.

Series, Ciba Café 8 series made by EFKA Mountain ves Co., Ltd., [2011]

Solsperse series, DISPARLON series of Nanben Chemical Company. Others have also proposed the use of existing surfactants as dispersants, anionic surfactants, such as: higher fatty acid salts, alkyl sulfonates, alpha olefin sulfonates, alkane sulfonates, alkyl benzene sulfonic acids Salt, sulfosuccinate salt, alkyl sulfate salt, alkyl ether sulfate salt, alkyl phosphate salt, alkyl ether phosphate salt, alkyl ether carboxylate, α-sulfo fatty acid oxime ester salt , sulfhydryl taurate and the like. Nonionic surfactants include, for example, glycerin fatty acid esters, polyglycerin fatty acid esters, sucrose fatty acid esters, sorbitan fatty acid esters, polyoxyethylene ethyl sorbitan fatty acid esters, polyoxygenated ethylene Alkyl ether, polyoxyethylene ethyl phenyl ether, polyoxyethyl ester fatty acid ester, fatty acid alkanol oxime glucoside and the like. The amphoteric surfactants include, for example, a burnt betaine, a fatty acid guanamine propyl betaine, an alkylamine oxide, and the like. The surfactants include, for example, an alkyltrimethylammonium salt, a dialkyldimethyl group, a ketone group, a methylbenzyl alcohol salt, a pyridyl group, a ruthenium salt, and the like. Others include: a surfactant such as a gas-based surfactant and a cellulose derivative, a polybasic acid salt, and a polystyrene sulfonate. - In order to suppress the aggregation of the dispersion by using the above-mentioned conventional dispersant to obtain the dispersion composition, the research is being carried out, but the dispersion of the dispersion medium is small, and the particle size of the dispersoid is miniaturized and shaped. Therefore, the quality of the final product, the improvement of productivity, and the strength of the product: : Requirements: The proposed dispersant is not fully satisfied: When the use: According to the sub- and ionic groups, for example · When the dispersing medium (dispersion medium) is the interface interaction of the hydrophobic interaction of the water agent 201141602 Electro-adsorption, and the π-electron interaction derived from the aromatic ring, and between the particles, the formation of the electric double layer The electrostatic repulsion between the particles and the dispersion stabilization effect caused by the formation of the three-dimensional barrier, and the body agent and the builder are all effective methods, and various methods capable of achieving dispersion and agglomeration inhibition can be employed. On the other hand, due to hydrophobic interactions in non-aqueous dispersion women,

The effect of the electrostatic interface adsorption and electrostatic repulsion caused by Hi bio-based is limited. Therefore, the interfacial adsorption of the dispersant on the dispersed particles is based on the acid interaction between the dispersed particles and the specific part of the dispersant. On the basis of change: the choice of dispersant system will be based on the surface characteristics of the disperse, and the dispersing agent will be in a very limited condition, together with the dispersant under the condition of eight & And the affinity for the knife media must also be combined with a dispersing medium used to select the most suitable dispersing agent. ° : Various ionic surfactants are also very limited in water systems. The scope of application is solved by the complex #dispersed particle meter, because it can be used by multiple adsorption points, and the thicker protective layer is used to design the dispersion system. The size of the dispersed particles and the dispersant molecules are: a) thus by the high molecular weight dispersant: the size is different, in other words, because the size of the molecules is limited or limited. The size of the larger high molecular weight dispersant reader is multi-point adsorption and intertwined between the dispersing agent and the dispersing agent 201141602 and the dispersing agent. Burning and sowing techniques will promote the agglutination of dispersed particles, so there is a fundamental problem in dispersing the view of females. In order to achieve the goal of dispersion stabilization, the usual method is to

The use of stronger interactions between Knife and the agent to design the dispersion system', but in addition to the division and polarity change of the I ^ bullying, to ensure the mechanical and chemical stability of the dispersion composition, Ke Yu, the female, steep, dispersed particles In addition to the removal and film formation (high gloss, low temperature and short miso bow, film formation in time), when the dispersant is removed, it is required to perform, and the coat is easy to separate from the interface of the dispersant. The special characteristics of this product are improved in the final product, processing characteristics, quality filling::: surface is an important factor. In this view, the existing dispersants have not been filled to meet the required performance. In addition, the composite material obtained by dispersing the inorganic microparticles (particle size 1 to 100 nm) or organic fillers and pigments of the semi-P ^ size in the resin is called the polybutanide, but the fish 0. The particles of the 'Ding' water size are extremely difficult to uniformly disperse in the resin due to their ease of aggregation and the affinity for the resin. In the case where the particles of the Neflon-sized particles are in the form of ..., the 'Using the aqueous dispersion is scooped in the non-limiting'. The effective method is usually to use a dispersant to make the nanoparticles in the dispersion medium to prepare the dispersion, and to make the resin. Solvent 2 ==, or the state of the solution in which the resin is dissolved in the solvent is promoted and transferred and dispersed. In addition, as a method for pre-dispersing metal particles and gold seeds, which can be easily redispersed in 八/, pigment, and each C1, and before and after treatment, there are surface modifiers and The surface protection is a technique in which a W wood-coated dispersion particle, a 201141602 surface modifier, or the like is impregnated into a dispersion particle, and the prior art is often limited by the type of the dispersion medium and the amount of the dispersion, and the utilization range is extremely limited. @Dispersants or surface modifiers and surface protectants that solve this problem have not been found. If it is found that the dispersant which solves the above problems, that is, is not limited by the type of the dispersing medium and the amount of the dispersing substance, and has a general applicability to a wide range of materials (4), obtaining (4) a non-aqueous dispersion of the dispersing agent, And in the form of a powdery, granular or syrup which is obtained by dispersing or impregnating the dispersing agent with a dispersing agent as a surface modifying agent or a surface protecting agent of a dispersing agent, such a solvent replacement and From the viewpoint of changing the polarity and mixing with the resin solution, the industrial use value is extremely large. For example, as such a prior art, the patent document discloses a metal colloidal particle composed of a metal (tetra) particle (A) and a protective colloid (B) of (4) a metal nanoparticle (A). Further, the protective gel system is composed of an organic compound having a slow base (referred to as a polymer dispersant (4). [Prior Art Document] (Patent Document) Patent Document 1: Japanese Patent Laid-Open No. 2009-74 1 7 1 Disclosure of the Invention [Problems to be Solved by the Invention] Patent Document 1 discloses a dispersant having a carboxyl group. The dispersant is useful when the dispersion medium is water, but has poor dispersibility in a non-aqueous dispersion medium. In view of the problems of the prior art, R&D 201141602 was developed to provide a dispersant for non-aqueous dispersion media, which is applicable to a wide range of dispersoids, and can exhibit excellent dispersion stability by adding a small amount. Further, it is an object of the present invention to provide a dispersion composition which is obtained by using the dispersant, and an object of the present invention is to provide an organic particle or an inorganic substance. The particle is coated with the dispersing agent or impregnated with the dispersing agent. [Technical means for solving the problem] In order to achieve the above object, the dispersing agent for a non-aqueous dispersing medium of the present invention is represented by the following formula (1) The compound shown is composed of Ο R—o—(AO)n—x—ί—0H · - • (1) However, the meaning of the symbol of formula (1) is as follows. R indicates that it contains a branch. An alkyl group and/or an alkenyl group having an alkyl group and/or an alkenyl group having 1 to 24 carbon atoms. AO represents an oxygen-extension base having a carbon number of 丨 to 4, and n represents an average addition mole number of the epoxy compound. Further, in the range of 1 to 30, βχ is a linking group composed of a carbon atom, a hydrogen atom and/or an oxygen atom. Further, the oxime of the formula (1) is preferably an alkyl group having a carbon number of 丨15. The enthalpy of (1) is preferably a substance represented by the following formula (2): Ο 〜 Q - V - · Formula (2) Υ is from the carbon number 1 to the meaning of the symbol of the formula (2) as follows Any one of 201141602 selected from the group consisting of an alkyl group, a vinyl group, a vinyl group, and a carboxyl group-containing phenyl group. Preferably, it is an organic particle and/or an inorganic particle which is subjected to the above dispersing agent. Preferably, it is formed by dispersing the above-mentioned dispersant, and is a dispersion composition which is obtained by dispersing organic particles or inorganic particles in a non-aqueous dispersion medium by using the above-mentioned dispersant. After applying a coating composition to a substrate, a physical reaction or a chemical reaction is carried out, and the coating composition comprises: the dispersion composition described above, and the dispersion composition is made of a resin. The aqueous dispersion medium is preferably a member obtained by subjecting a coating composition to a substrate to perform a physical reaction or a chemical reaction, and the coating composition comprises: The mixture is mixed with a resin, and the dispersion composition uses a solvent as a non-aqueous dispersion medium. [Embodiment of the Invention] The dispersant for a non-aqueous dispersion medium of the present invention is composed of a compound represented by the following formula (1). ' ?

R—O—(AO)n~X—C—OH w Formula (1) The dispersant for a non-aqueous dispersion medium of the present invention is represented by the formula (1), and is composed of the following sites: a dispersing medium affinity portion Further, it comprises an epoxy-bonding bond and a dispersing-affinity moiety, which is composed of a sulfhydryl group; wherein the sub-chamber affinities and the dispersing affinities are linked by a linking group X. Let the meaning of the symbol of the formula (1) be as follows. R represents an alkyl group and/or an alkenyl group having a branched group 201141602 alkyl group and/or a dilute group and having a carbon number of 1 to 24. The AO table has an oxygen-free alkyl group having 1 to 4 carbon atoms, and η represents an average addition mole number of the alkylene oxide and is in the range of 1 to 30. The cross indicates a linking group composed of a carbon atom, an argon atom and/or an oxygen atom. The preferred embodiments of the present invention are described in detail below. 1. Hydrophobic group (R) A hydrophobic group (R) which can be used in the dispersing agent of the present invention, R is a hydrocarbon group derived from an alcohol, and R is an alkyl group and/or an alkyl group having a carbon number of 1 to 24 and a branched form. base. When R is an alkyl group and/or an alkenyl group, the carbon number of the starting material alcohol which can be used may be a single one or a mixture of alcohols having different carbon numbers. Further, the starting alcohol may be derived from synthesis or derived from nature, and further, the chemical structure may be a single composition or a mixture of a plurality of isomers. The raw material alcohols which can be used may be selected from conventional ones, except for the synthesis of butanol isobutanol, pentanol and 'or its isomers, hexanol and, or its isomers, heptanol and/or Its isomer, octanol and/or its isomer, 3,5,5-trimethylbenzene 1 hexanol, 'high olefin derived from propylene or butyl or a mixture thereof and by ketone group (. Iso) alcohol, isodecyl alcohol, isodecyl alcohol, isodecyl alcohol, isotridecyl alcohol, NEODOL 23, 25, 4S, % manufactured by Shell Chemicals. a can 45 Sasol company saf〇L23, Exxoii

EXXAL 7, pyyat or L 7 EXXAL 8N, EXXAL 9, EXXAL 10, EXXAL 11 and EXXAT ” + * L 1 3 ' manufactured by Mobil are also examples of higher alcohols that can be preferably used. Alcohol, decyl alcohol, lauryl alcohol (1-t-cavity alcohol), meat and alcohol (14-fold alcohol), decyl alcohol cetyl alcohol), stearyl alcohol (octadecyl alcohol), oleyl alcohol (shun -9-octadecene, etc., is also one of the 201141602 examples of higher alcohols that can be used. In addition, a single type of Guerbet Alcohol having a chemical structure of a 2-alkyl-1-alkanol type The composition, or a mixture thereof, etc., is also an example of a higher alcohol which can be preferably used, except for 2-ethyl-1-hexanol, 2-N 5-1,3-hexanol, 2-butyl-1-hexanol, 2-ethyl-1-heptanol, 2-propylheptanol, 2 ethyl-1-octanol, 2-hexyl-1-nonanol, 2-heptyl-i-undecyl alcohol, 2 octyl In addition to certain 1-dodecanol and 2-mercapto-1-undanol, isostearyl alcohol derived from a branched alcohol, etc., may be used in combination with two or more kinds of the alcohols described herein. The dispersant of the present invention, as described above, when the preferred hydrophobic group (R) is derived When the hydrocarbon group is a hydrocarbon group having a carbon number of 3 to 24 and a branched alkyl group and/or an alkenyl group content of 70% by weight or more, it is preferably used for the purpose of the present invention. When the radical (R) is a hydrocarbon group having hydrazine or a carbon number of i 2 or 2, or a carbon number exceeding 25, and even if the carbon number of the hydrophobic group is in the range of 3 to 24, when the linear alkyl group and/or When the content of the alkenyl group exceeds 3% by weight, the dispersion f may not be stably dispersed in the non-aqueous dispersion medium t, or the range of the dispersion medium that can be used is limited, or in the preparation step of the dispersion. Displacement or mixing of the same kind of dispersing medium. As a result, the stability of the dispersion is reduced and the deposit is immediately formed, or the stability over time is significantly reduced to produce the added value of the final product, and the yak y Problems such as reduced properties, reduced processing characteristics, and degraded quality. In order to >, to avoid the problem, and to make the effect of the present invention particularly effective, the appearance of the type is better. The effective hydrophobic group (8) is carbon number Branches of bismuth 2 oxoalkyl groups (A 〇) n of the dispersant of the present invention The preferred type of alkylene oxide, in the formula (1) 12 201141602, indicates that the enemy number is from 4 to 4, and the alkylene oxide is the mountainous soil. Specifically, the carbon number is 2, and the lime number is 3 The alkylene oxide is a cation. The oxane is a nuclear oxypropane. The carbon number is tetrahydrofuran or butyl butyl. The butylene oxide is #. ^ 乂l2-butylene oxide or 2,3- fluorene. In the present invention, eight (-(AO)(I), in the granule powder, the oxygen-extended alkyl chain for the dispersing agent of the dispersing agent can be a single-armed person for the purpose of affinity, epoxy or block The average length of the random chain of the random chain of the above-mentioned oxygen-fired random polymer chain is 丨, and the formula () indicates that the η of the epoxy burned carbon is preferably in the range of 1 to 3 Å. In the range of 3 to 20, the linker (X) linker (X) can be made from the 冓 ia in the form of a gas atom and an oxygen atom. , Youde # > A non-saturated smoky group, fluorenyl group, carbonyl group, vinegar group is preferably 'having an alicyclic structure, an aromatic ring structure, and may also have a repeating unit. When the linking group X contains a nitrogen atom and/or a sulfur atom and/or a phosphorus atom or the like, it is not suitable as a structural factor of the dispersing agent of the present invention because it has an effect of lowering the affinity of a few groups for the dispersing substance. Further, X of the formula (1) is preferably a stretching group having a carbon number of i to 15, and preferably an alkyl group having a carbon number of 1 to 8. This g, the X of the formula (1) is preferably a substance represented by the following formula (2) (2)

II Gun _ 1 However, the meaning of the symbol of equation (2) is as follows. Y is any one selected from the group consisting of an alkyl group having 1 to 15 carbon atoms, a vinyl group, a vinyl group, and a carboxyl group. 13 201141602 4. More preferable dispersing agent In the present invention, a dispersing agent of the following formula (3) Q Hall § can be more preferably used. RO-fCH^HaOVcH^C-OH . « · (3) However, in the formula (3), 'R is 8 to 18 octagonal, 4, and the main-<knife-type alkyl group is preferably n. The average addition mole number of oxyethane, m ^ 为 is preferably in the range of 3 to 20. The composition of the dispersant is limited to this standard 1, and the applicability of the 重|7 〇y ancient restatement: the expansion of the preparation of the dispersion, the selection range of the non-aqueous bifurcant media used; the mixing of different kinds of dispersing media Change. In this way, the composition range of the powder is limited, and the history of the dispersion stability over time can be better. The result is that the added value of the final product can be improved, the productivity is improved, the processing characteristics are improved, and the quality is stabilized. Wait. Door 5. Method for Producing Dispersant The dispersant of the present invention can be developed by conventional methods, ±_7, and +. It can be mistaken by the following method to make 'for example: by using the formula #5 ^ woody nuclear alkane addition in alcohol, amines, mercaptans, one of the proud... sub-interface active agent The compound (iv) is a raw material which is subjected to a method of reacting with a mesogenic lower-grade tauric acid or a salt thereof, a reaction with a terminal group of an epoxy compound, or a method of opening a vincent with a hydroxyl group at the terminal of an alkylene oxide. The method of splitting-reacting is not limited thereto. 6. The dispersed particles dispersed by the agent for dispersing the particles can be selected from inorganic-derived pulls and/or organic-derived particles.粒子Inorganic particles can be used: iron, aluminum, chromium, nickel, 201141602 recording, rhetoric, crane, steel, tin, free, wrong, titanium, and these alloys; or the silver, gold, platinum, etc.; Looking for a mixture. At this time, the particles are safely removed from the medium, and the metal ruthenium is also taken out, and can be broken by the following protective substances and fatty acids, and the base is reduced by acid: thiol (tetra) anhydride, thiol, Derivatization::, = family of acid,: homopolymer, polymer surfactant 1 ^ affinity to find. Low knife interface surfactant. Others are also two talc, mica, bentonite, dolomite, Shixi acid fishing, Shixi acid town, asbestos, carbonic acid handle, 'inverse magnesium, barium carbonate, calcium sulfate, sulfuric acid,, melon, and nitrogen oxide Shao, gas iron oxide, ashes acid, oxidation, magnesium oxide, aluminum oxide, titanium oxide, iron oxide, oxidation, antimony trioxide, oxygen = indium, indium tin, carbon cutting, nitrogen cutting, nitriding Boron, titanic acid pot, Shixi stagnation black, graphite, rock wool, glass wool, glass fiber, carbon fiber, carbon nanofiber, carbon nai (four) (single-walled nanotube, double-walled nanotube, multi-walled nai Rice tube) and so on. In addition, 'organic particles derived from: organic, heavy, condensed azo-sulfur, indanthrone, quinacridone, lanthanide, benzimidazolone Organic pigments such as phthalic acid, peryiene, phthalocyanine, anthrapyridine, and di〇xazine; polyethylene resin, polypropylene resin, polyester resin, resistance resin, and brewing Amine resin, aromatic polyamide resin, acrylic resin, vinylon resin, urethane resin, melamine resin, polystyrene resin, polylactic acid, acetate fiber, cellulose, hemicellulose , lignin, chitin, chitosan, starch, polyethylene, aromatic polyamine resin, polycarbonate, polyphenylene ether, polyetheretherketone, 15 201141602 Bismuth citrate, poly-caiformic acid diacetate, poly-cai dimethyl &amp; diced vinegar, poly-Maple (p°iysu1 -, polyphenylene sulfide test, "imine, etc." The dispersant of the present invention is combined. +., Knife, which disperses the particles, may be crystalline or amorphous. In addition, the above-mentioned dispersed particles "dispersed by the isotropic aging or astigmatic particles" may also be fibrous in the present invention. The above-mentioned dispersed particles of the dispersoid can be obtained by a conventional method. The method for preparing fine particles is roughly the following two methods: a top-down manner of mechanically grinding and miniaturizing coarse particles; The bottom-up (b〇tt〇m up) manner of the particles is formed by generating a plurality of unit particles and forming a cluster state by agglutination of the particles.

It can be preferably used by a method which is modulated by any method. In addition, these may be those by the thirst method or the dry method. In addition, the bottom-up approach has physical methods and chemical methods, but it can be by any method. The agent according to the present invention may be used in the step t of the top-down method of mechanically grinding and refining coarse particles, or may be formed in a cluster state in which a plurality of unit particles are formed and agglomerated by the particles. In the step of the bottom-up manner of the particles, 'or the following particles may be used: after the particles are prepared in advance by the aforementioned method,' the surface modifying agent or surface is called for the stable removal of the dispersed particles from the medium. A conventional protective agent for a protective agent to coat or remove particles after impregnation. The protective agent can be used in place of the aforementioned conventional dispersing agent. In order to more specifically explain the bottom-up mode, the preparation method of the metal nanoparticles in the above-mentioned dispersed particles is exemplified. From the bottom up, the physical side, the representative example is: evaporating the bulk metal in an inert gas and condensing it by colliding with the emulsion to generate the vapor in the gas of the nanoparticle 16 201141602 f Bu, the chemical branch is: in the liquid tissue after the protective agent is ion-reduced, the generated μ metal is in nanometer size 液相 liquid phase reduction method; and metal complex utilization: chemical reduction method, electric W:: 4. The liquid phase reduction method may be an electrochemical reduction method, a photoreduction method, or a method in which a chemical reduction method and a light irradiation method are combined. In addition, the dispersible particles can be preferably used in the present invention as described above in any of the top-down manner and the bottom-up manner, and the like can be in an aqueous system, a non-aqueous system, or a gas phase. Modulation in either environment. 7. Dispersing medium The dispersing medium which can be used in the present invention may, for example, be a phthalic acid solvent such as toluene, xylene, an aromatic hydrocarbon solvent, Zhengjiyuan, Cyclohexanol or Zhenggeng; Methylene chloride; _hydrocarbon solvent such as dichloroethane; diethyl ether, diisopropyl ether, dioxane (ane), tetrahydrofuran, dibutyl ether, butyl ethyl ether, decyl second butyl ether, pine oil Terpinyl methyl ether, dihydroterhanyl decyl ether, diethylene glycol diglyme, 13, ethereal solvent such as dioxolane; acetone, acetophenone, anthracene Ethyl ketone, decyl propyl ketone, diethyl ketone, decyl n-butyl ketone, methyl isobutyl ketone, monopropyl ketone, diisobutyl ketone, methyl amyl ketone, acetone acetone a ketone solvent such as isophorone, cyclohexanone, nonylcyclohexanone, 2-(1-cyclohexenyl)cyclohexanone, decyl isobutyl ketone, cyclohexanone or isophorone; Ethyl ester, propyl citrate, butyl formate, isobutyl phthalate, amyl citrate, decyl acetate, ethyl acetate, n-propyl acetate, isopropyl acetate, n-butyl acetate, isobutyl δ Purpose, Acidic butyl acrylate, (iso) decyl acetate, cyclohexyl acetate, lactic acid, 3-methoxybutyl acetate, diethyl hexyl acetate, ethyl butyl acetate, 17 201141602 2-ethyl acetate Hex vinegar, phenylhydrazine acetate, propionic acid, brewing, propionic acid, ethyl acetate, methyl acetate, ethyl acetate, butyl acetate, acetic acid, acetonitrile, ethyl acetate, butyl propionate, Acid isoamyl ester, ester solvent such as butyrolactone; ethylene glycol monoethyl ether, ethylene glycol monoisopropyl (tetra), ethylene glycol monobutyl ether monoethyl alcohol monoethyl sequestration, diethylene glycol Mono-n-butyl test, propylene glycol monomethyl mystery, propylene glycol monoethyl mystery, propylene glycol mono-n-propyl scale, propylene glycol grass n-butyl ether, dipropylene glycol monomethyl bond, [propylene glycol monoethyl _, dipropylene glycol single positive Propyl shunt, dipropylene glycol mono-positive H-ethylene glycol monomethyl test, triethylene glycol monoethyl (tetra), triethylene glycol mono-n-propyl ether, triethylene di-n-butane (tetra), tripropylene glycol monoethyl I Tripropylene glycol mono-n-propyl, di-propanol-alcohol, early-butyl butyl suture, etc., 々dtei 哥 醉 ether solvent, and these monoethers? Acid I solvent; alcohol dimethyl ketone, diethylene glycol diethyl bond, dimethyl ketone ether dipropylene glycol diethyl alcohol, n-propanol, isopropanol, butanol, heptanol, n-pentane Alcohol, decyl alcohol, allyl alcohol, gaseous ethanol, 2-methyl-1-butanol, isoamyl alcohol, methyl alcohol methyl isobutyl ketone, dipropylene diether ether special secondary entertainment • basic solvent. Methanol n-butanol, isobutanol, secondary butanol, secondary pentanol, n-hexanol, tetrahydrofurfuryl octyl undecyl alcohol, 1-ethyl-1-propanol secondary pentanol, secondary isoprene Alcohol, neopentyl hydrazine, hexanol, 2-methyl-1_pentan gi, 4-methyl-2-pentanol, heptanol, n-xinxin, 2-ethylhexanol, decyl alcohol, hydrazine - alcohol, lauryl alcohol, cyclopentanol, cyclohexanol, one. 1), terpineol C, L_: terpineol alcohol ethanol, two rabbit pine oil oxyethanol '- oleyl alcohol, pine oil oxygen male - Ί 夕 τ u Japanese TerPene chemical limited stock 刁 之Ersorb MTPH, τ iersorb DT〇-2in &gt; τ ΤΗΑ-90, Tersorb ΤΗΑ-70, and μμ TerS〇rb and cyclohexanol, 3-methoxybutanol, bis 18 201141602 acetol, 1,4- Butanediol, octanediol, etc.

Alcohol solvents such as FINEOXOCOL 140N, FINEOXOCOL 1600, FINEOXOCOL 180, FINEOXOCOL 180N, FINEOXOCOL 2000, etc.; ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol, monopropyl alcohol, 13 · butanediol, A glycol solvent such as a diol, polyethylene glycol or polypropylene glycol. Further, for example, a guanamine-based solvent such as dimethylacetamide or dimethylformamide may be mentioned. In addition, the 'dispersion medium can also be used: (meth)acrylic acid, (mercapto) acrylates such as vinyl groups, vinyl monomers such as vinyl acetate, ethylene (tetra), polyallyl derivatives, etc. Ethylene unsaturated monomers. Others may be used without any particular limitation: various types of resins, oligomers, and monomers used for coating and bonding, and f-type. Examples of D include, for example, acrylic resin, polyester resin, alkyd (Senian resin, amine vinegar resin, sulphuric acid resin, fluororesin, epoxy resin, polycarbonate resin, polyvinyl chloride resin, and flat). Further, the above-mentioned dispersion medium may be used singly or in combination of two or more kinds. Further, the purpose of the dispersant of the present invention is to provide a fine particle dispersion in a non-aqueous environment, but for . , Scythe Government Media 'either deliberately or accidentally, in the steps of making fine particle dispersions, or for the intended use, or when designing the final product, there is no water mixing or mixing in the middle. Other dispersing agents of the present invention can be produced by a known method, and within the above range, the type of the hydrophobic group, the type of the alkane and the addition form thereof, the amount of the added molar amount, and the linking group are particularly characterized. Limiting the time to choose the optimum composition, and in 19 201141602 compared to the conventional dispersant, it can make the dispersion of the wider variety of the more widely dispersed types, which can make the knife mass in the wider category. Knife on m(5) In terms of dispersing and stabilizing the media, the industrial use value is quite large. In addition, the dispersant of the present invention reduces the contained ions, heavy metal ions, and ions by the conventional refining method. Ion, soil test metal (4) The content of each ion of _ 素 ion. Dispersion, ion due to dispersion stability of the dispersion, recording resistance, oxygen resistance, electrical properties of the dispersion coating film (conductive properties, insulation properties), Time: 疋 ii = thermal, low-humidity, weather resistance has a large impact, so the content of the above-mentioned sub-- can be appropriately determined, but it is preferably less than 1 in the dispersing agent. In the present invention, the preferred dispersed particles are used. The content f' in the dispersion medium is not particularly limited as long as it can be dispersed in the non-aqueous dispersion medium: it varies depending on the use, but is further dispersed in the range of 〇5 to 7〇% by mass. The average particle diameter of the particles is preferably in the range of 10 (10), preferably in the range of 10 to 100 nm. Further, the preferred use conditions of the powder of the present invention are based on the weight of the dispersed particles relative to the dispersed particles. The range of % is better. ~ In addition, this The dispersion composition of the invention can be prepared by a conventional means for imparting weight, a homogenizing means, or a dispersing means. Examples of the dispersing machine which can be used include a roll mill such as a 2-roll or a 3-roll mill, and a ball mill. Vibrating ball mills, such as grinding machines, paint shakers, continuous disc bead mills, continuous ring bead mills, bead mills, sand mills, jet mills, etc. In addition, they can also be produced in ultrasonic waves. Further, the dispersing agent of the present invention not only disperses and stabilizes the dispersion of the dispersed particles in the non-aqueous dispersion medium 20 201141602, but also has a divergent stabilization effect, and... The function of the protective agent for removing the dispersed particles from the medium t can be customized, the adsorption inhibition on the wall surface of the container, the aggregation inhibition of the contamination, the easy redispersibility, the oxidation prevention of the metal particles, the particles Surface m... Surface modification, functional surface termination, solvent replacement and polarity change day &amp; ^ ^ ^ Parental impact relaxation, powder &amp; mobility improvement, powder curing to prevent M At The dispersing agent of the present invention is superior to the above-mentioned machine in this season, and the parental protective agent is more excellent.

The form and its addition, the 簟 ear, the # 4 IAU, the type of hydrophobic base in the bucket, and the linking group, etc., can make the desired disperse in a more dispersed medium than the conventional protective agent. Decentralized stability. A substrate which is coated with a coating composition comprising the dispersion composition of the present invention and which uses a resin as a non-aqueous dispersion medium or a mixture comprising the dispersion composition of the present invention and a resin. The composition is applied and the dispersion composition is a non-aqueous dispersion medium using, for example, glass, a resin film, a glass composite material, a ceramic enamel, a metal/steel plate, or the like. According to the present invention, it is possible to provide a dispersant for a non-aqueous dispersion medium which is applicable to a wide range of dispersion f, and which exhibits excellent dispersion stability by adding a small amount. Further, a dispersion composition can be provided which is obtained by using the dispersant, and a film which is composed of the dispersion composition can be provided. Further, an organic particle or an inorganic particle may be provided which is coated with the dispersant or impregnated with the dispersant. 21 201141602 [Embodiment] Hereinafter, embodiments and comparative examples of the present invention will be described. In addition, hereinafter, "parts" indicating the amount of blending 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. &lt;Synthesis of Dispersant&gt; [Production Example 1 (Synthesis of Dispersant 1 in Toluene Solvent] Addition of isodecyl alcohol oxide oxime 0m () 1 adduct 598 g (lmol) and chloroacetic acid to the reactor Sodium 151g (1.3mol)' was mixed and homogenized. Then, after the reaction system temperature was 60 ° C, 52 g (1.3 mol) of sodium oxynitride was added, and the temperature of the reaction system was raised to 80 ° C. The reaction was carried out for 3 hours. After the reaction, a white suspension solution was obtained by dropwise addition of 98% (1.2 mol) of 98% sulfuric acid. Then, the white suspension solution was washed with distilled water, and the solvent was evaporated under reduced pressure. Dispersant 丨 (R: isodecyl, AO: ethylene bromide, n: l 〇, X: CH 2 ) [Production Example 2 (synthesis of dispersant 2)] In addition to using 2-propyl-1-heptanol The same operation as in Production Example 1 was carried out except that the ethylene oxide 10 m〇1 adduct 598 g (1 mol) was substituted for the isomeric oxime ethylene oxide 10 mol adduct 598 g (1 mol) to obtain a dispersant 2 (R). : 2-propyl-1-heptyl, AO: ethylene oxide, η: 10, X: CH2) [Production Example 3 (Synthesis of Dispersant 3 except for the use of isotridecyl alcohol oxide) M〇l adduct 640g (lmo l) The same operation as in Production Example 1 was carried out except for the substitution of isodecyl alcohol ethylene oxide 10 η η ι ADD ADD 598 g (1 mol) to obtain dispersant 3 (R: isotridecyl 'AO: ring Ethylene oxide, η: 1〇, X: CH2). 22 201141602 [Production Example 4 (synthesis of dispersant 4)] In addition to the use of iso- 12-mole ethylene oxide 20 mol adduct 1080 g (lmol) The same operation as in the production example was carried out except that the decyl alcohol ethylene oxide 1 〇 m 〇 1 adduct 598 g 〇 m 〇 1) was obtained to obtain a dispersing agent 4 (R. isododecyl, A 〇: ring Oxygen bromide, n · 2〇, X: [Production Example 5 (synthesis of dispersant 5)] In addition to the use of branched C11-14 alcohol (product name: EXXAL 13, Exxon M〇bl1 company) epoxy B Alkane 5mol / propylene oxide 5m〇i random adduct 71〇8 (1111〇1), substituted isodecyl alcohol Ethylene oxide 1〇111〇1 adduct 598^1 claw 〇 1) In the production example, the same operation was carried out to obtain a dispersant 5 (R. Branch C11-14 alkyl, A: ethylene oxide and propylene oxide, n: , X: CH2) 制造 [Production Example 6 (Dispersion) Synthesis of agent 6)] In addition to the use of branched C11 ~ η alcohol (product name: E XXAL 13, propylene oxide 2m〇i/ethylene oxide block adduct 968g (lm〇1), substituted by isodecyl alcohol ethylene oxide lOmol adduct 598g (lmol) X The same operation as in Production Example 1 was carried out to obtain a dispersant 6 (R. branched C11-14 alkyl, A: propylene oxide and ethylene oxide, n: 10, X: ch2). [4 cases of 7 (synthesis of dispersant 7)] In addition to 954 g (1 mol) of isobutanol ethylene oxide 2 〇 mol adduct, 598 g (lmol) of octahexol Ethylene Ethylene oxide addition product, The same operation was carried out for the other ones &amp; Example 1, to obtain a dispersing agent 7 (R: isobutyl group, A oxime oxirane, η: 20, X: CH 2 ). 23 201141602 [Production Example 8 (Synthesis of Dispersant 8)] In addition to using 306 g (1 mol) of an isobutanol propylene oxide 4 mol adduct, a substituted ketone ethylene oxide l〇m〇l adduct 598 g (1 mol) The same operation as in Production Example 1 was carried out except that the dispersing agent 8 (R: isobutyl group, AO: epoxy propylene, n: 4, X: CH2) was obtained. [Production Example 9 (synthesis of dispersant of dispersant 9)] obtained by reacting 954 g (lmol) of isobutanol ethylene oxide 20 mol of adduct and l56 g (lm〇l) of suberic anhydride for 2 hours at TC. Dispersant 9 (R: isobutyl, AO: ethylene oxide, n: 20, X: CO(CH2)6) [Production Example 10 (Dispersant 1〇 dispersant synthesis)] at l2〇°C 510 g (1 mol) of a 2-methyl-1-heptanol ethylene oxide 8 mol adduct and succinic anhydride i〇〇g (iniol) were reacted for 2 hours to obtain a dispersing agent 10 (R: 2-propyl-1) - heptyl group, AO: ethylene oxide, n: 8, X: COCH2CH2) [Production Example 11 (synthesis of dispersant of dispersant 11)] Isobutanol ethylene oxide 10 mol addition product at 120 ° C 598 g (1 mol) and 98 g (1 mol) of maleic acid were reacted for 2 hours to obtain a dispersing agent ll (R: isodecyl group, AO: ethylene oxide, η: 10, X: COCH=CH). 12 (synthesis of dispersant of dispersant 12)] obtained by reacting 640 g (lm〇l) of isodecyl alcohol ethidium bromide monoester and 98 g (lmol) of maleic anhydride at 120 C for 2 hours. Dispersant, 12 (R: isotridecyl, AO: ethylene oxide, η: ΐ〇, χ: COCH: =CH). [Production Example 13 (synthesis of dispersant 13)] Tridecyl alcohol (80% by weight) / lauryl alcohol (2% by weight) mixed 24 201141602 compound ethylene oxide 10mol adduct 637g (lmol), substituted isodecyl alcohol epoxy plant 10m〇l addition The same operation as in Production Example 1 was carried out except for 598 g (1 mol) to obtain a dispersant 13 (R: isotridecyl and lauryl, AO: ethylene oxide, η: 10, X: CH2). [Production Example 14 (synthesis of dispersant of dispersant 14)]. 2,000 mol of isobutanol ethylene oxide adduct 954 g (lm〇l) and trimellitic anhydride 192 g (lm〇1) at 12 Torr. The reaction was carried out for 2 hours to obtain a dispersant 14 (R: isobutyl, A: ethylene oxide, η: 2 〇, X: c〇C6H3). [Example 1] The dispersant of the present invention

/ Η 1 W 7, / 〆, y, J Dispersant 1 · 5 parts (converted in solid form), dissolved in a solvent as a dispersing medium (isopropanol or diethylene glycol monobutyl ether) In the case of 68 parts of acetic acid ester, 3 parts of magnesium oxide (Mg0) as a dispersoid and 10 〇〇 mL of cerium oxide having a diameter of 1 mm were added, and the obtained solution was subjected to micronization treatment using a ball mill. The dispersant of the present invention is composed of a compound represented by the formula (1) comprising a hydrophobic group (R), an oxygen-extension group (-(A0)n), and a linking group (8) of the composition shown in the following Table i, The dispersant of this comparative example was composed of a compound represented by a hydrophobic group (R), an oxygen-extension group (-(called _), and a linking group (X) of the composition shown in Table 2 below. After the obtained treatment liquid was transferred to a transparent trough t, the treatment liquid was observed with the naked eye, and the dispersibility of the treatment liquid in the container was evaluated by the following basis. The results of the knife decoction are shown in Tables 1 and 2. All the dispersoids are dispersed in the solution to the sediment. And at the bottom of the pirates, no 〇 is observed. Most of the disperse is placed in the bath, but at the bottom of the container. I noticed a very small deposit. -P Μ 25 201141602

The quality of the product can be dissolved in the X-ray white liquid solution or TJ 11 table [装/—V. S 5 ◎ ◎ ◎ ◎ ◎ ◎ ◎ ◎ ◎ ◎ ◎ ◎ ◎ ◎ ◎ ◎ ◎ ◎ ◎ ◎ ◎ ◎ 1 }&gt;&lt;I 1 豸1 1 ac ο 1 ί oa S t 1 ί 1 1 « 4 6 1 1 € 1 1 frj S 1 ι ί ί 1 «& 3 1 8 I 1 CM 9 i 1 1 5 II g έ ί 1 s Ϊ a;1 Y 8 1 1 S ϊ 03⁄4 ? 8 1 S 1 0 &lt; T 1 〇ί: 1 〇ω ί io Interest T { 8 3 ω τ 1 §# Ιύ 3蹿&Disc 1 w 1 «广' r off! ^ 1 s I 1 1 g ί 1 Constitution 1 1乂s τ ί ο β m Τ 1 I 1 1 ο f 'W 1 s Palace Nm*^ 1 Οί 1 -1 ci| 1'1 + Η + . Exact-A l —) ο % Φ 1 —1 ci| Η Η Μ; Η Η Η • • 1 •&gt;—1 Cvl 汾: Η ten mm iWfl jlfii 9S + blowing Mi H #Γ Τ-Ι (Μ CO to οό σ> 〇f—ii ·-« trM ca * ^Γ CO •*4 26 201141602 [Table 2] Dispersibility evaluation (dispersion) Magnesium oxide (MgO) (dispersion medium) Diethylene sulphate; Ethyl ether acetate XXXXXXXXXXXXXXXXX Isozyme X XXXXXXXXXXXXXXXX 一&quot;CH'7广1~CH2- I-C0-CH=CH- C-» !; SY ϋ 丄? 1 % 綍ο CSJ 镏〇% 〇砩〇你〇砩〇〇砩〇酸镏η: 砩0 癸Acid! 1 stupid formic acid polyethylene glycol (600) diacetate 'temperature nitroxide + CC£> \^y 〇 〇 Ί Ί -V- 镏 镏 back Ί ί 聚乙烯 嘀舸 聚 聚Hexenol partial saponification ϊ ϊ ϊ t 0 ί-4 — (AO) η - 1 «*3 § 1 1 § 1 I 1 ό i ί Pi methyl Η Η Η Η Η Η Η Η Η Η Η R-ί 堪 45 i Comparative Example 31 Comparative Example 4 LO &lt; 〇 mm 盈: Bu Jun 〇〇〇 ii 1 Comparative Example 10! mmt 1 SS* 1 i3 1 Comparative Example 13 g LO . «V* Comparative Example 16 Comparative Example 17 As is clear from Table 1, the dispersing agent of the present invention is excellent in dispersibility. 27 201141602 [Example 2] Dispersing agents of the present invention (numbered as the second end of Table 3 are designated as 2, :}, and 4 7 1〇12 13) are a predetermined amount or a dispersing agent of a comparative example (Table 3) Comparative Example 1, 2, 3, 5, 1 1 , π - 曰 1 11) pre-straightened, dissolved in methyl ethyl ketone as a dispersion medium, and then added as a dispersion of oxidation error (Zr〇^5 parts, the product was subjected to a micronization treatment for 2 hours using the product % ULTRA APEX MILL UAM-〇〇5 (using a diameter of 50 oxidized beads, a peripheral speed of 10 m/sec) manufactured by Shou Industrial Co., Ltd. The dispersant of the present invention is composed of a compound of the formula (1) comprising a hydrophobic group (R), an oxygen-expanding group (·(10) and a linking group (X) having a composition shown in the following Table 3, and this comparative example The powder &quot; powder is composed of a compound represented by the formula (1) comprising a hydrophobic group (r), an oxygen-extension group (_(ΑΟ)η·), and a linking group (χ) of the composition shown in Table 3 below. As a result, after the obtained treatment liquid was transferred into a transparent container, the treatment liquid was observed with the naked eye, and the following minimization was evaluated on the same basis as above: The dispersibility of the treatment liquid in the inside and the dispersion stability of (4) (the dispersing agent is 0.25 parts and the dispersing agent is 5 parts) in the container after 24 hours. In addition, a part of the treatment liquid (dispersing agent is 0.25 parts) And the dispersion is 5 parts of the treatment liquid), and the particle size of the oxidized hammer after the micro-treatment of the milk e-ship m〇del 9 is used. Further, the amount of methyl ethyl ketone relative to the dispersant is relatively 5 parts, Ο parts, 0.15 parts, 〇·〇 5 parts, decyl ethyl ketone are % 份, μ, 94.85 parts, 94.95 parts, respectively. The above dispersibility and dispersion stability of the naked eye; The results of the measurement of the particle size of zirconia are as shown in Table 3. - In addition, the dispersant of the present invention or the dispersant of the comparative example was used as a dispersing agent of methyl alcohol _ of 28 201141602 as a dispersing substance. The ratio of the gasification error was 0.25 wounds, 94.75 wounds, and 5 parts, and the dispersion was prepared, and 25 parts of methyl ethyl ketone of the acrylic tree sap (trade name ACRYpET VH, manufactured by Mitsubishi Rayon Co., Ltd.) was dissolved. 7 parts of the dispersion was mixed in 70 parts, and after obtaining a dispersion, it was made by Shou Industrial Co., Ltd. Product name ULTRA ΑρΕχ MiU UAM-〇〇5 (using oxidized wrong beads of 5〇(4) at a speed of 1〇111/sec), the dispersion was subjected to a refining treatment for 2 hours, and the dispersant of the present invention has the following The compound represented by the formula (1) having the composition shown in Table 3 was composed of a compound represented by the formula (1) having the composition shown in the following Table 3. As a result, the obtained treatment was carried out. After the liquid was transferred into a transparent container, the dispersibility of the treatment liquid in the container was evaluated on the same basis as described above by observing the treatment liquid with the naked eye. The results are shown in Table 3. Further, the above dispersion (micronized for 2 hours) was applied to a clean glass plate having a thickness of 10 mm, and then dried at 12 Torr.干燥 Dry for 1 hour to obtain a coating film. Next, after the paper having the letter printed in the 12th mark is placed under the glass plate, the transparency of the coating film obtained on the glass plate is evaluated from the viewpoint of whether or not the letter can be recognized through the coating film. Sex. The results are shown in Table 3. ◎: The letter text of the 12th word can be clearly recognized. 〇: The coating film produces a slight turbidity, but the letter text of the 12th word can still be recognized. χ·The film is turbid, and the letter of the 12th word cannot be recognized. [Table 3] 29 201141602

Transparency of si i coating film ◎ ◎ ◎ @ ◎ ◎ ◎ XXXXX Dispersibility I ◎ ◎ ◎ ◎ @ ◎ ◎ ◎ XXXXX Oxidation error methyl ethyl ketone dispersion evaluation particle size i__ ΙΟ 25nm ! 28tuq [25nm 45nm 60iut 30ηια 35nra 30t\a 755aa 485ara 1 1 1 Dispersion stability i (after 24 hours) Luo ◎ ◎ ◎ ◎ 0 ◎ ◎ I 1 1 I 1 . Dispersing dispersant usage (%) (relative to Zr02) g ◎ ○ ○ ○ ◎ ◎ XX ◎ ◎ ◎ ◎ ◎ ◎ ◎ ◎ ◎ ◎ ◎ ◎ ◎ ◎ ◎ ◎ ◎ ◎ ◎ ◎ ◎ ◎ ◎ XXXXX X-^CHz^ - (3⁄4广I s' 1 1 Μ s ! -CO-CHa-CHi- | -co-cH-ai- 1 _CH2— \ € 1 —CH2— -CO-CH-CH- Polyrolled Ethyl (10) Isodecyl Sodium Acetate (20%) Aqueous solution) Polyethylene glycol (600) diacetate-CAO) π.-世〇i 1 1 ο S w 1 1 i 1 1 Nest Q &amp; 1 1 s § 1 1 ca I i [ s I l 1 0 s Ά 1 1 n I 1 1 8 s ca T 1 Pi Isodecyl 1:2-propyl-1-heptylisotridecyl.isotridecyl Iisobutyl 2-propyl-1 -heptylisotridecyl.isotridecyl^;8〇3|Most% &gt; Laurel base 2〇ϋ«:?« Difficult Sr-isotridecyl 1 isotridecyl dispersant rH IN PQ Ο 2 ca ia Comparative Example 2 Comparative Example 3 Comparative Example 5 Comparative Example U 30 201141602 3 It can be seen that the dispersibility and dispersion of the dispersing agent which is excellent in the stability of the hair styling agent are not caused by + γ, and the particle size of the dispersing agent in the dispersing body of the present invention is used. ®· is much smaller than the particle size of the dispersion of the separator of the comparative example, and the dispersion of the dispersion of the present invention is also excellent, and according to the coating film of Table 3, The dispersion of the invention constitutes an excellent dispersion of the dispersion of the present invention. The dispersion of the dispersant of the comparative example is not determined, and the L&quot; is called the dispersion stability of the flash. This is a comparative example of the undetected enthalpy. 3. Comparative Example 5, Dimensional _ The particle size of zirconia of Comparative Example 11 [Example 3] The dispersing agent of the present invention (the numbers shown on the left end of Table 4 are the mouths of Bub 2, 3, 4, and 12) Parts or comparative examples (Comparative examples shown in Table 4, 2, 3, (4), a powder of 1 胄, dissolved in diethylene glycol monobutyl phthalate acetic acid as a dispersion medium _ 7 In addition, one part of the multi-walled carbon nanotubes (product name VGCF_X, manufactured by Showa Denko Co., Ltd.) was added as a dispersion, and then the coating was used to shake H (ROCKING MILL's product name RM_5 developed by SEIWA Technology, using diameter 〇5 The obtained solution was subjected to a refining treatment for 12 hours, and the dispersion #1 of the present invention was composed of a hydrophobic group (8) and an oxygen-extended alkyl group (-(A〇) having the composition shown in Table 4 below. N_) and a compound represented by the formula (χ) of the above formula, the dispersant of the comparative example is a hydrophobic group (R) and an oxygen-extended alkyl group (_(Α) having a composition shown in Table 4 below. 〇) η_) and a compound represented by the formula (1) of a linking group (χ). As a result, after the obtained treatment liquid was transferred to a transparent container, the dispersibility of the treatment liquid in the container immediately after the miniaturization treatment was evaluated by the same observation as above, and the treatment liquid was visually observed. 24 31 Dispersion stability of the treatment liquid in the container after 201141602 hours. The results are as shown in Table 4, in addition to the dispersant of the present invention or the dispersant of the comparative example, diethylene glycol monobutyl ether acetate which is not dispersible, and as a dispersing material: The rice tube (trade name VgcF_x^μμ ^ t t 制 例 例 例 例 例 例 例 例 例 例 例 例 例 例 例 例 例 例 例 例 例 例 例 例 例 例 30 30 30 30 30 30 30 30 30 30 30 30 30 昭 昭 昭 昭After the acetate, the micronization treatment was carried out for 1 hour using the above-mentioned paint shaker, which was composed of the compound represented by the formula (1) having the composition shown in Table 4 below, and the dispersant of the comparative example. It is composed of a compound represented by the formula (丨) having the composition shown in the following Table 4. The dispersion stability of the treatment liquid diluted with diethylene glycol monobutyl ether acetate is defined as dilution stability. The dilution stability was evaluated on the same basis as the dispersibility. The results are shown in Table 4. In addition, the dispersant of the present invention or the dispersant of the comparative example was used as a dispersing medium for diethylene glycol monobutyl. Ether acetate, and the same multi-walled carbon naphthalene as the above The proportion of the tube was changed to 1 part: 7 parts: i part, and the refining treatment was carried out for 12 hours using the above-mentioned paint shaker, and after the dispersion was obtained, 'acrylic resin was dissolved (manufactured by Mitsubishi Ray0n Co., Ltd., ACRYPET VH) After 70 parts of the dispersion of 70 parts of methyl ethyl ketone solution was mixed, 70 parts of the dispersion was obtained, and after the dispersion was obtained, the dispersion was applied to a clean glass plate of 10 mm thickness, and dried using a dryer at 12 (TC drying). The coating film of the present invention was composed of a compound represented by the formula (1) having the composition shown in the following Table 4, and the dispersing agent of the comparative example was as shown in Table 4 below. A composition of the compound represented by the formula (1) is formed. Next, a paper having a letter 32 201141602 printed in a 12-character print is placed under the glass plate, and the letter is recognized from the film. The transparency of the obtained coating film on the glass plate was evaluated on the same basis as above. The results are shown in Table 4. [Table 4] ◎ ◎ ◎ o ύ Cave-fh珅钕4 0-r (effect Φ) QHI-TS) si^ly^Js @ ◎ ◎ ©

X

X

X

X ◎ ◎ ◎ ◎ ◎ ◎ ◎ ◎ ◎ ◎

X

X

X

X

X

X

X

X X- US - accounted for 3| *3丨

If f?6—

Lf

If HVS. «Βΐ 丨 αονϊ 丨ί .2 畐 _g il £il k 3 - 3«丨 Η

2SS cosf iii 33 201141602 It is understood from the table that the dispersing agent, the dispersion stability, and the dilution stability of the present invention are excellent. Further, as shown in Table 4, the coating film composed of the dispersion of the present invention was excellent in transparency, and it was confirmed that the dispersion of the present invention has excellent dispersibility. Further, the transparency of the dispersant of the comparative example was not measured. [Example 4] "Preparation of oxidized hammer acrylate monomer dispersion (1)" 鍅 鍅 鍅 powder (trade name pcs manufactured by Nippon Denshi Co., Ltd. - subgranules 30 nm) 1 part and methyl group In the case where 4 parts of ethyl ketone are mixed, 10 parts of the dispersing agent of the present invention (the number shown in the left end of Table 5 is (1)-1 to (1)-6) or the dispersing agent of the comparative example is added. ((1)_Comparative Example (1) - Comparative Example ι') shown in Table 5, after using the product name ultra APEX MILL UAM-005 manufactured by Shou Industrial Co., Ltd. (using a diameter of 5 〇μηι The beads were centrifuged at a rate of 10 m/sec. for 4 hours to prepare a zirconium-zirconium sulphide. The dispersant of the invention was composed of a hydrophobic group (R) comprising the composition shown in Table 5 below. a compound of the formula (1) which is an alkylene group (-(A〇)n_) and a linking group (χ), and the dispersing agent of the comparative example is a hydrophobic group comprising the composition of the following table: A compound represented by the formula (1) of an oxygen alkyl group (-(A〇D and a linking group (X)). A phenoxyethyl acrylate is added to one part of the obtained zirconia dispersion. 10 parts of the product of the first industrial pharmaceutical company, NEW FRONTIER PHE) and pentaerythritol triacrylate (trade name NEW FRONTIER ΡΕΤ-3, manufactured by Dai-ichi Kogyo Co., Ltd.) were mixed and mixed, and the solvent was used using a rotary evaporator. The decyl ethyl ketone is removed under reduced pressure to obtain a zirconia acrylate monomer dispersion (1). 34 201141602 <<Preparation of yttrium oxide acrylate monomer dispersion (2)>> Commercially available zirconia dispersion (SZR-M, manufactured by Suga Chemical Co., Ltd., - sub-particle size 3 nm, containing 3% by weight, dispersion of alcohol, adding the dispersant of the present invention (the number shown on the left end of Table 5 is ( 2)] to (2)-13) 3 parts or a dispersing agent of a comparative example ((7) Comparative Example 2, (7) - Comparative Example 2') shown in Table 5), acetoxyphenoxy ethoxylate An industrial pharmaceutical company, trade name NE w FR (10)TIER ρΗΕ) ι $ part and quaternary tetradecyl propylene hydride (trade name NEW FRONTIER PET-3, manufactured by Industrial Pharmaceutical Co., Ltd.) 15 parts and mixed, using a rotary evaporator The methyl ethyl group of the solvent is removed under reduced pressure to obtain the acrylic acid of the zirconia. The body (7), the dispersant of the present invention is composed of a compound represented by the formula (1) having the composition shown in the following Table 5, and the dispersant of the comparative example is represented by the formula (1) having the composition shown in Table 5 below. Composition of the compound shown. <Evaluation of Characteristics of Dispersion> a. Transparency of Appearance The acrylonitrile monomer dispersion of zirconia was placed in a transparent glass container, and the number 12 was placed under the above container. After printing the paper, the transparency of the dispersion was evaluated from the viewpoint of whether or not the dispersion can recognize the letter, based on the following. The results are shown in Table 5. ◎: After the dispersion was added to a glass container of 5 cm depth, the letter of the letter n was observed. The dispersion was transparent. 〇: After the dispersion was added to a glass container of 1 cm depth, it was clearly observed that 12 The letter of the letter word. The dispersion is slightly turbid. X: After adding the dispersion to a glass container of 1 cm depth, it is not clear 35 201141602 The letter of the 12th word is found. The dispersion is turbid. b. The viscosity of the wrong acrylate monomer dispersion was measured at 25 using an E-type viscometer (trade name rE_8〇r, manufactured by Toki Sangyo Co., Ltd.). The results are shown in Table 5. c. The refractive index of the yttrium oxide acrylate monomer dispersion was measured at 25 ° C using an Abbe refractometer (trade name: NAR-1T, manufactured by ATAGO Co., Ltd.). The results are shown in Table 5. Production of Film" One part of the photopolymerization initiator (IGACURE 184) was added and mixed in 100 parts of the above-mentioned oxidized acrylate monomer dispersion (1) or (2) to obtain an oxidized error. By using an applicator (YA made by Kodaira Co., Ltd.) Type) 'Applying the oxidized misc paste to a film thickness of about 50 μm on a polyethylene terephthalate film, and using a high pressure mercury lamp to irradiate ultraviolet rays having an intensity of 8 〇 w/cm and an energy of about 200 mJ/cm 2 , Obtaining a photopolymerization cured film of an oxidized acrylate monomer dispersion. <Evaluation of characteristics of photopolymerization cured film> a. Appearance transparency is placed under the polyethylene terephthalate film and printed in a 12-character print After the paper of the mother-child, the transparency of the photopolymerization cured film obtained on the polyethylene terephthalate film was evaluated from the viewpoint of whether or not the cured film was recognizable. The results are shown in Table 5. ◎: The letter of the 12th character can be clearly recognized. 〇: The hardened film produces a little turbidity, and it is still 36 201141602. The letter of the 12th word can be recognized. χ : The hardened film is turbid, but the letter of the 12th word cannot be recognized. b. The refractive index of the refractive index to the photopolymerization cured film was measured at 25 ° C using a PRISM COUPLER (MODEL 2010/M) manufactured by Seki Technotron Co., Ltd. The results are shown in Table 5. c. Pencil hardness versus photopolymerization Hardened film pencil Hardness, according to JIS K5 400, a scratch test of the photopolymerization cured film was carried out using a pencil of a predetermined hardness. The results are shown in Table 5. [Table 5] 37 201141602 Raspberry 5 Goods w- s S; CN| 3= a: : Tongue ca S 33 i 1 J 1 Xu u&gt; to 2! CD 2ί »-»4 U) 5&&lt;〇τ-* O) 5 S CO ^hI CJ o r-4 53 φ m/^Λ tMt ίσ s — ca sr»4 CM ··&lt; C^ U&gt; M! CM κβ F-^ ·—· Cs) &lt; Kamakura 1 t ; 1 〇o Ο 〇Ο Ο @ © ◎ © ◎ ◎ ◎ ◎ ◎ @ ◎ © ◎ XXXX is poor. This SS m 苕ια inch s w-4 \Λ s 茗ΙΟ s ca S ΟΦ § »&gt;*« sm C4 U) i kis &lt;-· S tQ w&gt;-4 g 1 1 1 1 &quot;Ίϋ奶* flag| % sr*H 〇o 00 g Cft &lt;Λ § § 8 oo ^1 os 4Ω ssos IA, g %〇ό s 〇s S .^ S Ο 5 s Cn os ιίί 释 狰秭 di 〇〇〇o ο Ο ◎ ◎ ◎ ◎ ◎ ◎ ◎ m ◎ ◎ ◎ ◎ ◎ XXXX r X ί I 1 € 1 1 豸 1 ! i ii If 1 1 1 \€ ί f C2 t: I el JI T i «0 5 ί I ? 1 51 1 1 «·* s 1 \ ac Y 1 T 1 S Τ I test i € \ rf ! 1 豸 1 [ 豸1 i Y 1 νέ: u* t ! r ή ο ! &lt; 1 1 w&gt; I 1 £ I 1 1 !! a&gt;Disc 1 ^ I C6 &gt;**wg T Ί FS g II state s dish t ^ 1 us 1 1 II 15 | 1 ΐ 1 1 must /&quot;s §« vj 〇^ & dish f ^ 1 § 1 1 1 1 1 3庵2&gt;揉1 “ 1 •4 1 1 1 ο f Ό 1 1 gg \ϊ s?disc i ^ f I 1 1 § w&gt; 1 1 &lt;n 1 1 1 § ·**·»·. j 1 i 1 Ρί « l *-^1 € c!〇1 r άϊ Λν 1 ·-1 c 1 CO t^i 眸 target 1 ·—1 1 1=^ 〇!〇Λ I »—i € » C^3, % 1 •—I 1 (Nl t^{ 眸: '丨丨+ '丨丨4~ 眸'•1 4~ 眸-S3* Τ ·—t *~H s φ ^-1 i «—1 »—1 ϊ φ ·——1 ! ^-1 Φ Seeking mm « Ss •s^· Sr-· III BC Winter K a- t^i Φ- »- 1^i Φ- 珑 υ υ ίφ T-&lt; 1 rH 1 A [ fi -w 1 rH •w** i〇1 &lt;0 l rH r4 I 03⁄4 I &lt;*^N to lc^ 1 «k&lt;&gt; to 1 &lt;NI iO i C5 v^· ¢^ 1 V—/ 00 J 〇, &lt;^5 Φ 1 s«^ ο 1 ο FK rt 1 ci •w^ CH r4 f &lt;MP〇I—« 1 03 1 I Ϊ i i? 丄»-JM sfwa (M ia λ From Table 5, the dispersion system of the present invention Excellent dispersibility (transparency in appearance) and Refractive index, and the light dispersion polymerization of the present invention the hard film based 38201141602 have excellent transparency, a high refractive index and good pencil hardness. However, in the dispersion of the comparative example ((1) - Comparative Example (Comparative Example r, (7) - Comparative Example 2, (7), Comparative Example 2)), since the aggregation occurred, the viscosity and the refractive index could not be measured, and the turbidity was observed. Further, the photopolymerization hardened film of the dispersion of the comparative example was turbid, and the refractive index and pencil hardness could not be measured. In Tables 1 to 5, ΕΟ矣千搜7 a 辰不呵氧乙院, P〇 indicates epoxy propylene. Further, the transmittance of the dispersion composed of the dispersant of the comparative example could not be measured. Further, the refractive index and pencil hardness of the photopolymerization cured film of the dispersion composed of the dispersant of the comparative example could not be measured. The dispersion composition of the present invention can be used in the following fields: a mixed material f, 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 Neil magnet , guiding medium, high performance catalyst for fuel cell, organic solar cell, nano glass element, agent* drug carrier, environmental catalyst, paint, printing ink, resist for inkjet film, ink for writing instruments , an optical film, the above-mentioned I" film hard coating film, etc. The dispersing agent of the present invention can effectively make the nano-size of the in-process product and its manufacturing step derived from inorganic substances or derived from organic substances/, The non-aqueous dispersion dispersing technique/or the anisotropic material is coagulated, and the dispersing mass in the dispersing medium is suppressed to achieve long-term dispersion stabilization, and the processing characteristics, quality stability, and productivity are improved. The invention has been described in detail and with reference to specific embodiments. - The technical field of the invention is generally known as the two stone yang. It can be used without departing from 39 201141602. In the case of the spirit and scope of the present invention, it is easy to know. "And this application is based on the application of the date of May 26, 2010 on the date of the application of the Japanese rabbits. Japanese Patent Application No. 2010-286489, the entire disclosure of which is incorporated herein by reference. [Simple description of the diagram] None [Main component symbol description]

Claims (1)

201141602 VII. Scope of application for patents: Composition of compounds: a dispersant for non-aqueous dispersion media, which is obtained by the following formula #photo &amp; . (1) R~0~(A〇)rr 仁疋, R of the formula (1) represents an alkyl group and/or an alkenyl group having a branched alkyl group and/or having a carbon number of 1 to 24, and AO of the formula (1) represents an oxygen-exane having a carbon number of from 4 to 4. The average addition molar number of the n-oxane is in the range of 丨 to 3 ,, and the χ of the uncoated (1) is composed of a carbon atom, a hydrogen atom and/or an oxygen atom = as in the scope of the patent application 帛i In the non-aqueous dispersion medium, X of the formula (1) is an alkylene group having 1 to 15 carbon atoms. 0 II • C· = Dispersion of the non-aqueous dispersion medium as described in the item (4), (g), where X of the formula (1) is a substance represented by the following formula (2), and the body (2) However, γ of the formula (2) is any one selected from the group consisting of a carbon number of 丄 to a stretching group of a carbon number of 15, a stretched ethylene group, a phenylene group, and a carboxyl group-containing phenyl group. 4 • An organic particle and/or an inorganic particle 'It is formed by breaking the non-aqueous dispersion dispersant described in Patent Application No. 4, Item 2 or Item 3 or impregnating the above dispersant. 5 - a dispersion composition which is obtained by dispersing organic particles or inorganic particles in a non-aqueous dispersion using the non-aqueous fraction (4) of the application of the scope of the patent, i.e., 201141602, item 2 or item 3. Made in the media. A coating composition comprising: a dispersion composition according to claim 5, wherein the dispersion composition uses a resin as a non-aqueous dispersion medium. A coating composition comprising: a mixture of a slurry composition and a resin as described in claim 5, wherein the dispersion composition uses a solvent as a non-aqueous dispersion medium. 8. A member obtained by applying a coating composition according to the above-mentioned claim or item 7 to a substrate, and then performing a physical reaction or a chemical reaction. 42 201141602 IV. Designation of Representative Representatives (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: