Classifications

• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
  • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
  • C08G65/32—Polymers modified by chemical after-treatment
  • C08G65/329—Polymers modified by chemical after-treatment with organic compounds
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
  • C08F299/00—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers
  • C08F299/02—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
  • C08F299/00—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers
  • C08F299/02—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates
  • C08F299/022—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates from polycondensates with side or terminal unsaturations
  • C08F299/024—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates from polycondensates with side or terminal unsaturations the unsaturation being in acrylic or methacrylic groups
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
  • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
  • C08G65/32—Polymers modified by chemical after-treatment
  • C08G65/329—Polymers modified by chemical after-treatment with organic compounds
  • C08G65/331—Polymers modified by chemical after-treatment with organic compounds containing oxygen
  • C08G65/332—Polymers modified by chemical after-treatment with organic compounds containing oxygen containing carboxyl groups, or halides, or esters thereof
  • C08G65/3322—Polymers modified by chemical after-treatment with organic compounds containing oxygen containing carboxyl groups, or halides, or esters thereof acyclic
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
  • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
  • C08G65/32—Polymers modified by chemical after-treatment
  • C08G65/329—Polymers modified by chemical after-treatment with organic compounds
  • C08G65/333—Polymers modified by chemical after-treatment with organic compounds containing nitrogen
  • C08G65/33348—Polymers modified by chemical after-treatment with organic compounds containing nitrogen containing isocyanate group
  • C08G65/33351—Polymers modified by chemical after-treatment with organic compounds containing nitrogen containing isocyanate group acyclic
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
  • C09D171/00—Coating compositions based on polyethers obtained by reactions forming an ether link in the main chain; Coating compositions based on derivatives of such polymers
  • C09D171/02—Polyalkylene oxides
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
  • C09D201/00—Coating compositions based on unspecified macromolecular compounds
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
  • C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
  • C09D7/40—Additives
  • C09D7/65—Additives macromolecular
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
  • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
  • C09K23/42—Ethers, e.g. polyglycol ethers of alcohols or phenols

Definitions

• the present invention relates to a polyoxyalkylene compound, a dispersant comprising said compound or a salt thereof, a dispersion composition containing said compound, a dispersion medium, and a dispersoid, and a photocurable composition containing said compound and a photopolymerization initiator.
• Polyoxyalkylene compounds can control their polarity, viscosity, reactivity, etc. by adjusting the type of oxyalkylene units that make them up and their degree of polymerization, which gives them properties such as flexibility and three-dimensional repulsion, and they are used in a variety of applications, including cleaning agent compositions, water treatment agents, scale inhibitors, lubricants, plasticizers, and dispersants.
• laminated electronic components such as multilayer ceramic capacitors (MLCCs) and multilayer ceramic substrates are manufactured by printing a conductive paste made of metals such as silver or nickel, a solvent, and binder resin onto green sheets made of ceramics such as barium titanate, alumina, and ferrite, and binder resin, and then laminating them.
• organic components such as resin contained in the green sheets and conductive paste are removed by a heat treatment at 300°C to 600°C called the degreasing process. If residual carbon is generated during this process, it can lead to a decrease in the performance of electronic components and the generation of defective products, so the organic components to be mixed are required to have good thermal decomposition properties.
• dispersants are used to efficiently disintegrate ceramic powders and metal powders in a solvent and to stably disperse the powders after disintegration.
• dispersants containing polyoxyalkylene chains are used.
• Patent Documents 1 and 2 report a polyoxyalkylene compound having a polyethyleneimine structure as a dispersant for dispersing ceramic powder or metal powder in a solvent at a high concentration.
• Patent Document 3 reports a slurry composition for molding ceramic sheets, which contains a polymer dispersant that is an anionic copolymer (particularly, a copolymer of methacrylic acid and a methacrylic acid ester having a polyoxyalkylene group) containing a structural unit (a) having an acidic group and a structural unit (b) having a polyoxyalkylene group.
• Patent Document 4 reports a nickel paste that uses a polyoxyalkylene compound as a dispersant.
• the properties of dispersants particularly, ease of thermal decomposition in the degreasing process).
• a technique in which the powder is surface-treated in advance with a dispersant.
• the surface treatment of the dispersant is carried out, for example, by dispersing the powder in a dispersion medium in the presence of a dispersant, and then heating and drying at a temperature at which the dispersant does not thermally deteriorate.
• dispersants containing polyoxyalkylene chains are prone to thermal decomposition, so the drying temperature cannot be increased and drying can take a long time.
• the thermal decomposition of dispersants containing polyoxyalkylene chains can be accelerated.
• dispersants containing polyoxyalkylene chains have issues with their heat resistance when dried.
• polyoxyalkylene compounds having ethylenically unsaturated double bonds are used as raw materials for photocurable resin compositions used in paints, coating agents, dry film resists, color resists, inks, adhesives, etc.
• Patent Document 5 reports a photocurable resin composition for dry film resists that contains a urethane (meth)acrylate having an oxyalkylene group in the molecule.
• Dispersants containing polyoxyalkylene chains do not have sufficient heat resistance during drying. Therefore, one of the objects of the present invention is to provide a dispersant that is resistant to thermal decomposition during the drying process when surface treating powder, but is prone to thermal decomposition during the degreasing process, which is at a higher temperature than the drying process.
• one of the objects of the present invention is to provide a photocurable composition capable of forming a cured film having high adhesion to a substrate.
• a polyoxyalkylene compound having a specific substituent is a dispersant that is difficult to be thermally decomposed in the drying process when surface treating powder, but is easily thermally decomposed in the degreasing process, which is at a higher temperature than the drying process.
• the present inventors have also found that a photocurable composition containing the polyoxyalkylene compound and a photopolymerization initiator can form a cured film with high adhesion to a substrate.
• the present invention based on these findings is as follows. [1] Formula (1):
• n is a number from 1 to 4, a is a number from 1 to 40; AO represents an oxyalkylene group having 2 to 4 carbon atoms; When a is a number of 2 or more, two or more AO may be the same or different from each other; When a is a number of 2 or more and two or more AO are different from each other, the structure of a (AO) may be any one of a random copolymer structure, a block copolymer structure, or a structure having both a random copolymer portion and a block copolymer portion, R 1 to R 4 each independently represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or a group represented by formula (X1) to formula (X4):
• X is any one of the following: At least one of R 1 to R 4 is a substituent X; When two or more substituents X are present, the two or more substituents X may be the same or different from each other, and when n is a number of 2 or more, two or more R 3 are , may be the same or different.
• the polyoxyalkylene compound has a weight average molecular weight of 1,000 to 15,000.
• a photocurable composition comprising the polyoxyalkylene compound according to [1] above and a photopolymerization initiator.
• the photocurable composition according to the above [4] which is used as a coating agent.
• the present invention it is possible to obtain a dispersant which is unlikely to be thermally decomposed in the drying step when the powder is surface-treated, but which is likely to be thermally decomposed in the degreasing step which is performed at a higher temperature than the drying step. Furthermore, according to the present invention, it is possible to obtain a photocurable composition capable of forming a cured film having high adhesion to a substrate. Furthermore, according to the present invention, a photocurable composition capable of forming a cured film having a high anti-fogging effect can be obtained.
• the polyoxyalkylene compound of the present invention has the formula (1):
• a polyoxyalkylene compound represented by the formula (1) (sometimes abbreviated as “compound (1)” in this specification). Each symbol in formula (1) will be explained below in order.
• n is a number between 1 and 4.
• the nitrogen atoms in compound (1) act as adsorption sites for the dispersoids. If n exceeds 4, compound (1) may be adsorbed across the dispersoids to form a bridging structure, which may result in aggregation.
• n is preferably a number between 2 and 4, and more preferably 2 or 4.
• a is the number of repeats of AO and is a number from 1 to 40. From the viewpoint of the dispersion performance of compound (1), a is preferably a number from 3 to 30, and more preferably a number from 8 to 22.
• AO represents an oxyalkylene group having 2 to 4 carbon atoms. AO may be either linear or branched. Examples of AO include an oxyethylene group, an oxypropylene group, and an oxybutylene group.
• the carbon atom terminal of (AO) a is bonded to the nitrogen atom (N) in formula (1), and the oxygen atom terminal of (AO) a is bonded to any one of R 1 to R 4 in formula (1).
• the two or more AO may be the same as or different from each other.
• the structure of (AO) a may be any of a random copolymer structure, a block copolymer structure, or a structure having both a random copolymer portion and a block copolymer portion.
• the structure of (AO) a is preferably a homopolymer structure or a block copolymer structure, and more preferably a diblock copolymer structure.
• (AO) a is preferably a polyoxyalkylene chain formed from at least one selected from the group consisting of an oxyethylene group, an oxypropylene group, and an oxybutylene group, more preferably a polyoxyalkylene chain formed from an oxyethylene group and an oxypropylene group, and even more preferably a polyoxyalkylene chain having a diblock copolymer structure formed from a block of an oxyethylene group and a block of an oxypropylene group, from the viewpoint of the dispersibility of compound (1).
• (AO) a is a polyoxyalkylene chain having the diblock copolymer structure
• the block of the oxyethylene group is bonded to N in formula (1)
• the block of the oxypropylene group is bonded to any one of R 1 to R 4 in formula (1).
• (AO) a is a polyoxyalkylene chain formed from oxyethylene groups and oxypropylene groups
• the molar ratio of oxyethylene groups:oxypropylene groups is preferably 1:9 to 6:4, more preferably 4:6 to 6:4.
• R 1 to R 4 each independently represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or a group represented by formula (X1) to formula (X4):
• the two or more X's may be the same or different, but are preferably the same.
• n in formula (1) is a number of 2 or more, two or more R 3s may be the same or different, but are preferably the same.
• R 1 to R 4 are each independently preferably a hydrogen atom or a substituent X represented by any one of formulas (X1) to (X4), and more preferably a hydrogen atom or a substituent X represented by formula (X2).
• the ratio of the substituent X in the compound (1) is preferably 0.3 to 0.9, more preferably 0.5 to 0.9, from the viewpoint of the adhesion of the compound (1) to the substrate.
• the ratio of the substituent X in compound (1) can be calculated, for example, from the charged amounts of raw materials used to produce compound (1).
• compound (1) is produced from an intermediate that is a polyoxyalkylene compound in which R 1 to R 4 in formula (1) are hydrogen atoms, and a compound (for example, an isocyanate compound) for modifying a hydroxyl group of the intermediate and introducing a substituent X
• the ratio of the substituent X in compound (1) can be calculated from the charged amounts of the intermediate and the compound.
• Y in formulas (X1) to (X4) represents a hydrogen atom or a methyl group. From the viewpoint of the dispersion performance of compound (1) and the resistance to thermal decomposition during the drying process, Y is preferably a methyl group.
• the weight average molecular weight (sometimes abbreviated as "Mw” in this specification) of compound (1) is 1,000 to 15,000. If this Mw is less than 1,000 or exceeds 15,000, the dispersion performance of compound (1) may decrease. From the viewpoints of the dispersion performance of compound (1), the difficulty of thermal decomposition in the drying process, and the ease of thermal decomposition in the degreasing process, this Mw is preferably 4,000 to 10,000.
• the "weight average molecular weight” refers to the weight average molecular weight calculated in terms of standard polyethylene glycol by gel permeation chromatography (GPC) using N,N-dimethylformamide (DMF) as the developing solvent.
• Compound (1) can be produced by modifying the hydroxyl group of a polyoxyalkylene compound in which R 1 to R 4 in formula (1) are hydrogen atoms with an isocyanate compound, acid anhydride, halide, or the like containing an ethylenically unsaturated double bond, and introducing a substituent X.
• a polyoxyalkylene compound in which R 1 to R 4 in formula (1) are hydrogen atoms can be produced by adding an alkylene oxide to a polyethylene polyamine (e.g., diethylene triamine) having 2 to 5 nitrogen atoms.
• the addition reaction of the alkylene oxide may or may not use a catalyst.
• the catalyst used in the addition reaction of the alkylene oxide include an alkali catalyst and a Lewis acid catalyst.
• the alkali catalyst include oxides of alkali metals or alkaline earth metals, hydroxides of alkali metals or alkaline earth metals, alcoholates, alkylamines such as triethylamine, and alkanolamines such as triethanolamine.
• Examples of the Lewis acid catalyst include boron trifluoride and tin tetrachloride.
• the amount of the catalyst used is generally 0.01 to 5.0% by mass based on the mass of the reaction product after the addition reaction is completed.
• the addition reaction of alkylene oxide can be carried out, for example, in an inert gas atmosphere such as argon or nitrogen gas, at 50 to 200° C. and 0.02 to 1.0 MPa, in the presence of a catalyst as required, by adding alkylene oxide to the raw material polyethylene polyamine having 2 to 5 nitrogen atoms while continuously pressurizing the alkylene oxide.
• an alkyl group having 1 to 4 carbon atoms can be introduced into a part of the reaction product by reacting the reaction product after the addition reaction of alkylene oxide with an alkyl halide having 1 to 4 carbon atoms, in the presence of an alkali catalyst as required.
• Examples of compounds for modifying the hydroxyl groups of a polyoxyalkylene compound and introducing a substituent X include isocyanate compounds, acid anhydrides, and halides.
• Examples of isocyanate compounds include 2-isocyanatoethyl acrylate, 2-isocyanatoethyl methacrylate, 1,1-(bisacryloyloxymethyl)ethyl isocyanate, and 2-(2-methacryloyloxyethyloxy)ethyl isocyanate.
• Examples of acid anhydrides include acrylic anhydride and methacrylic anhydride.
• Examples of halides include acryloyl chloride and methacryloyl chloride.
• the present invention provides a dispersant comprising compound (1) or a salt thereof (preferably a dispersant comprising compound (1)).
• the dispersant of the present invention may be used alone or in combination of two or more kinds.
• the dispersant of the present invention may also be used in combination with other dispersants or additives.
• the acid that forms the salt of compound (1) may be either an organic acid or an inorganic acid, or may be a mixture of an organic acid and an inorganic acid.
• organic acids include acetic acid, glycolic acid, oxalic acid, citric acid, lactic acid, malic acid, acrylic acid, and methacrylic acid.
• inorganic acids include hydrochloric acid, nitric acid, sulfuric acid, and phosphoric acid. Either the organic acid or the inorganic acid may be used alone or in combination of two or more kinds.
• the present invention provides a dispersion composition containing compound (1), a dispersion medium, and a dispersoid.
• Compound (1), the dispersion medium, and the dispersoid may each be used alone or in combination of two or more.
• the content of compound (1) in the dispersion composition of the present invention is preferably 0.1 to 100 parts by mass, more preferably 0.5 to 50 parts by mass, and even more preferably 1 to 30 parts by mass, relative to 100 parts by mass of dispersoid. If the content is less than 0.1 parts by mass, the dispersoid may not be sufficiently dispersed, and even if the content exceeds 100 parts by mass, an effect commensurate with the content may not be obtained.
• dispersoids examples include organic powders and inorganic powders. Either one type of organic powder or inorganic powder may be used alone, or two or more types may be used in combination. A mixture of organic powder and inorganic powder may also be used.
• organic powders include organic pigments such as azo pigments, diazo pigments, condensed azo pigments, thioindigo pigments, indathrone pigments, quinacridone pigments, anthraquinone pigments, benzimidazolone pigments, phenylene pigments, phthalocyanine pigments, anthrapyridine pigments, and dioxazine pigments.
• organic pigments such as azo pigments, diazo pigments, condensed azo pigments, thioindigo pigments, indathrone pigments, quinacridone pigments, anthraquinone pigments, benzimidazolone pigments, phenylene pigments, phthalocyanine pigments, anthrapyridine pigments, and dioxazine pigments.
• inorganic powders include metal powders such as iron, aluminum, chromium, nickel, cobalt, zinc, tungsten, indium, tin, palladium, zirconium, titanium, copper, silver, gold, and platinum; alloy powders made of two or more metals; composite powders made of metals and non-metals; and composite powders made of metals and alloy powders.
• Inorganic powders include, for example, powders of silicate minerals, other silicate compounds, carbonate compounds, sulfate compounds, hydroxide compounds, oxide compounds, nitride compounds, carbide compounds, titanate compounds, etc.
• Specific examples include powders of kaolin, clay, talc, mica, bentonite, dolomite, calcium silicate, aluminum silicate, magnesium silicate, calcium carbonate, magnesium carbonate, barium carbonate, calcium sulfate, barium sulfate, aluminum sulfate, aluminum hydroxide, iron hydroxide, zirconium oxide, magnesium oxide, aluminum oxide, titanium oxide, iron oxide, zinc oxide, antimony trioxide, indium oxide, indium tin oxide, silicon carbide, tungsten carbide, aluminum nitride, silicon nitride, boron nitride, barium titanate, calcium titanate, strontium titanate, carbon black, glass fiber, carbon fiber, carbon nanofiber, carbon nanotubes (single-wall
• the content of the dispersoid in the dispersion composition of the present invention (when two or more types of dispersoids are used, the total content of those dispersoids) is preferably 1 to 75 mass %, more preferably 9 to 75 mass %, based on the total dispersion composition.
• the dispersion medium may be either water or an organic solvent, and is preferably an organic solvent.
• organic solvents include aromatic hydrocarbon solvents such as toluene and xylene, hydrocarbon solvents such as cyclohexane, ketone solvents such as acetone and methyl ethyl ketone, ester solvents such as ethyl acetate and n-propyl acetate, glycol ether solvents such as ethylene glycol monoethyl ether and ethylene glycol monoisopropyl ether, glycol ether ester solvents such as ethylene glycol monoethyl ether acetate and propylene glycol monomethyl ether acetate, terpene solvents such as terpineol, dihydroterpineol, and dihydroterpinyl acetate, and alcohol solvents such as methanol, ethanol, and isopropanol.
• the content of the dispersion medium in the dispersion composition of the present invention (when two or more types of dispersion medium are used, the total content of those) is preferably 10 to 1,000 parts by mass, more preferably 10 to 900 parts by mass, and even more preferably 30 to 900 parts by mass, per 100 parts by mass of the dispersoid.
• the dispersion composition of the present invention may contain various additives such as dispersants, binders, plasticizers, and defoamers other than compound (1) as long as the effects of the present invention are not impaired.
• the dispersion composition of the present invention may contain an acid that forms a salt with compound (1), and compound (1) may be present as a salt in the dispersion composition of the present invention.
• acids that form a salt of compound (1) include those mentioned above.
• the dispersion composition of the present invention can be produced, for example, by a method of adding a dispersoid to a mixture of compound (1) and a dispersion medium, and then stirring and mixing the resulting mixture at room temperature, or by a method of adding a dispersion medium and compound (1) to a dispersoid, and then stirring and mixing at room temperature.
• Known equipment can be used for stirring, mixing, or dispersion. Examples of known equipment include a hybrid mixer, a roll mill, a ball mill, a bead mill, a sand mill, a homogenizer, a disperser, and a planetary mixer.
• the dispersion composition of the present invention may also be produced by dispersing a mixture containing compound (1), a dispersion medium, and a dispersoid using an ultrasonic bath.
• the present invention provides a photocurable composition containing compound (1) and a photopolymerization initiator.
• the compound (1) and the photopolymerization initiator may each be used alone or in combination of two or more.
• the content of compound (1) in the photocurable composition of the present invention (when two or more types of compound (1) are used, the total content of those) is preferably 10 to 90% by mass, more preferably 30 to 80% by mass, and even more preferably 50 to 70% by mass, based on the total mass of the photocurable composition, from the viewpoints of coatability on a substrate and anti-fogging effect.
• the photopolymerization initiator is not particularly limited, and any known photopolymerization initiator can be used.
• known photopolymerization initiators include the following: 1-Hydroxycyclohexyl phenyl ketone, benzil dimethyl ketal, 2-hydroxy-2-methyl-1-phenylpropan-1-one, 1-[4-(2-hydroxyethoxy)phenyl]-2-hydroxy-2-methyl-1-propan-1-one, oligo[2-hydroxy-2-methyl-1-[4-1-(methylvinyl)phenyl]propanone, 2-hydroxy-1-[4-[4-(2-hydroxy-2-methylpropionyl)benzyl]phenyl]-2- Acetophenone compounds such as methylpropan-1-one, 2-methyl-1-[4-(methylthio)]phenyl]-2-morpholinopropan-1-one, 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)butan-1-one, 2-dimethylamin
• the content of the photopolymerization initiator in the photocurable composition of the present invention is preferably 0.5 to 5.0% by mass, more preferably 1.0 to 4.0% by mass, and even more preferably 1.5 to 3.0% by mass, based on the total photocurable composition, from the viewpoints of adhesion to the substrate and anti-fogging effect.
• the photocurable composition of the present invention may contain one or more solvents.
• the solvent is preferably an organic solvent.
• organic solvents include aromatic hydrocarbon solvents such as toluene and xylene, hydrocarbon solvents such as cyclohexane, ketone solvents such as acetone and methyl ethyl ketone, ester solvents such as ethyl acetate and n-propyl acetate, glycol ether solvents such as ethylene glycol monoethyl ether and ethylene glycol monoisopropyl ether, glycol ether ester solvents such as ethylene glycol monoethyl ether acetate and propylene glycol monomethyl ether acetate, terpene solvents such as terpineol, dihydroterpineol, and dihydroterpinyl acetate, and alcohol solvents such as methanol, ethanol, and isopropanol.
• its content in the photocurable composition of the present invention is preferably 10 to 90% by mass, more preferably 20 to 70% by mass, and even more preferably 30 to 50% by mass, based on the total photocurable composition, from the viewpoints of coatability on a substrate and anti-fogging effect.
• the photocurable composition of the present invention may contain additives other than compound (1), photopolymerization initiator, and solvent, as long as the effects of the present invention are not impaired.
• additives include pigments, colorants, thickeners, sensitizers, defoamers, leveling agents, antioxidants, plasticizers, antistatic agents, etc.
• Each of the additives may be used alone or in combination of two or more.
• the photocurable composition of the present invention may contain an acid that forms a salt with compound (1), and compound (1) may be present as a salt in the photocurable composition of the present invention.
• acids that form a salt of compound (1) include those mentioned above.
• the photocurable composition of the present invention can be produced by mixing compound (1) with a photopolymerization initiator.
• Known equipment can be used for mixing. Examples of known equipment include a hybrid mixer, a roll mill, a ball mill, a bead mill, a sand mill, a homogenizer, a disperser, and a rotation-revolution type mixer.
• the photocurable composition of the present invention is preferably used as a coating agent (particularly as a coating agent for forming a cured film having an anti-fogging effect).
• the generation of the target product can be confirmed by analyzing the 1 H NMR chart obtained under the above measurement conditions.
• the generation of compound 1 can be confirmed by the disappearance of the peaks ( ⁇ 5.64 ppm, 6.19 ppm) of hydrogen added to the carbon-carbon double bond of the methacryloyl group of 2-isocyanatoethyl methacrylate, and the appearance of the peaks ( ⁇ 5.59 ppm, 6.12 ppm) of hydrogen added to the carbon-carbon double bond of the methacryloyl group, which is a part of the substituent X of compound 1.
• Comparative Compound 1 (Intermediate 1)
• an adsorbent product name: Kyoward 700, manufactured by Kyowa Chemical Industry Co., Ltd.
• the molecular weight of Comparative Compound 1 (Intermediate 1) was measured by GPC, and the weight average molecular weight was 6,500.
• the 1 H NMR chart of compound 1 is shown in FIG. 1.
• the ratio of the substituent X in compound 1 was calculated to be 0.6 from the weight average molecular weight (6500) of comparative compound 1 (intermediate 1), the number of active hydrogen atoms bonded to the nitrogen atom (5), and the amount (130.0 g) of the compound, and the amount (0.06 mol) of 2-isocyanatoethyl methacrylate.
• the ratio of the substituent X in the following compounds 2 to 9 was calculated in the same manner as the ratio of the substituent X in compound 1.
• Table 1 shows n, (AO) a , R 1 to R 4 (i.e., substituent X (the type of the formula and Y), and R 1 to R 4 other than substituent X) in formula (1) of compounds 1 to 9 or comparative compound 1 (intermediate 1) obtained as described above, weight average molecular weight (Mw), and ratio of substituent X.
• Example 1 to 9 ⁇ Examples 1 to 9 and Comparative Example 1> Compounds 1 to 9 were used as dispersants in Examples 1 to 9, and Comparative Compound 1 (Intermediate 1) was used as a dispersant in Comparative Example 1. The presence or absence of sedimentation and shear viscosity were measured as follows, and the dispersing performance of these compounds was evaluated.
• thermo decomposition in the degreasing process the resistance to thermal decomposition in the drying process (hereinafter referred to as “heat resistance in the drying process”) and the ease of thermal decomposition in the degreasing process (hereinafter referred to as “thermal decomposition in the degreasing process") of the dispersants of Examples 1 to 9 (i.e., compounds 1 to 9) and the dispersant of Comparative Example 1 (i.e., comparative compound 1 (intermediate 1)) were evaluated as follows.
• a dispersion composition was prepared in the same manner as in Examples 1 to 7 or Comparative Example 1, except that no dispersant was used.
• the shear viscosity of the obtained dispersion composition at a shear rate of 10 (1/s) at 20 ° C. was measured with a rheometer and evaluated according to the following criteria. The results are shown in Table 2. (Evaluation Criteria) ⁇ : Shear viscosity is 0.60 Pa ⁇ s or less. ⁇ : Shear viscosity is more than 0.60 Pa ⁇ s and less than 1.50 Pa ⁇ s. ⁇ : Shear viscosity is more than 1.50 Pa ⁇ s.
• the dispersant of the present invention is a dispersant that has excellent dispersion performance, heat resistance in the drying process, and thermal decomposition in the degreasing process.
• Example 10 to 18 photocurable compositions containing any of Compounds 1 to 9 and a photopolymerization initiator were prepared.
• Comparative Example 2 a photocurable composition was prepared using Blemmer DA-800AU (a polyoxyalkylene compound having an ethylenically unsaturated double bond, manufactured by NOF Corporation) instead of Compounds 1 to 9.
• Blemmer DA-800AU a polyoxyalkylene compound having an ethylenically unsaturated double bond, manufactured by NOF Corporation
• the obtained photocurable composition was dropped onto either a copper substrate or an ITO substrate, and a coating film was formed using a doctor blade.
• the obtained coating film was dried at 80° C. for 5 minutes, and then the substrate on which the dried coating film was formed was placed in an inert box, and nitrogen replacement was performed for 2 minutes.
• UV irradiation was performed using a UV irradiation device (manufactured by Fusion UV Systems Co., Ltd.) under conditions of an integrated light amount of 900 mJ/cm 2 , and a cured film having a thickness of 40 ⁇ m was produced.
• the substrate on which the dried coating film obtained in ⁇ Evaluation of the coating property of the photocurable composition> was formed was placed in an inert box, and nitrogen replacement was performed for 2 minutes. Thereafter, UV irradiation was performed using a UV irradiation device (manufactured by Fusion UV Systems Co., Ltd.) under the condition of an integrated light amount of 900 mJ/ cm2 , and a cured film with a thickness of 20 ⁇ m was produced. The produced cured film was placed at a height of 6 cm from the hot water surface at 50 ° C.
• Compound (1) of the present invention is useful as a dispersant.
• the photocurable composition of the present invention containing compound (1) and a photopolymerization initiator is useful as a coating agent.

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