Polyoxyalkylene compound, dispersant, dispersion composition, and photocurable composition

Abstract

Provided are: a polyoxyalkylene compound represented by formula (1) and having a weight-average molecular weight of 1,000-15,000 (wherein the symbols in formula (1) are as defined in the description); a dispersant comprising the compound or a salt thereof; a dispersion composition containing the compound, a dispersion medium and a dispersoid; and a photocurable composition containing the compound and a photopolymerization initiator.

Description

TECHNICAL FIELD

[0001] The present application relates to a polyoxyalkylene compound, a dispersant composed of the compound or a salt thereof, a dispersion composition containing the compound, a dispersing medium and a dispersed substance, and a photocurable composition containing the compound and a photopolymerization initiator. BACKGROUND

[0002] The polyoxyalkylene compound can control its polarity, viscosity, reactivity, etc. by adjusting the kind of the oxyalkylene unit constituting it or its polymerization degree, thereby imparting it with softness, steric hindrance repellency, etc. characteristics, and can be used for various purposes such as detergent compositions, water treatment agents, scale inhibitors, lubricants, plasticizers, dispersants, etc.

[0003] On the other hand, laminated electronic components such as multilayer ceramic capacitors (MLCC) and multilayer ceramic substrates are manufactured by a process in which a green sheet composed of barium titanate, alumina, ferrite and the like ceramics and a binder resin, and a conductive paste composed of a metal such as silver or nickel and a solvent and a binder resin are printed and laminated. The organic components such as resins contained in the green sheet and the conductive paste are removed by a heating treatment at 300°C to 600°C called a debinding process after the green sheets are laminated. At this time, if carbon residue is generated, it can cause a decrease in performance of the electronic component and generation of defective products, and thus it is required that the organic components to be compounded have good thermal decomposability.

[0004] In the paste composition for green sheet formation and the conductive paste, a dispersant is used in order to efficiently disperse the ceramic powder and the metal powder in the solvent and to stably disperse the powders after the dispersion. From the viewpoint of the dispersibility of the powders and the thermal decomposability of the dispersant, a dispersant containing a polyoxyalkylene chain can be used.

[0005] For example, a polyoxyalkylene compound having a polyethyleneimine structure is reported in Patent Literature 1 and Patent Literature 2 as a dispersant for dispersing ceramic powder and metal powder in a solvent at a high concentration. A ceramic sheet formation paste composition containing a high molecular dispersant which is an anionic copolymer containing a structural unit (a) having an acidic group and a structural unit (b) having a polyoxyalkylene group (particularly, a copolymer of methacrylic acid and a methacrylate having a polyoxyalkylene group) is reported in Patent Literature 3. A nickel paste using a polyoxyalkylene compound as a dispersant is reported in Patent Literature 4. In addition, in recent years, along with the high performance of electronic components, the performance of the dispersant (particularly, easy thermal decomposability in the debinding process) is increasingly required.

[0006] On the other hand, in order to improve the dispersibility of the powder, a method of previously performing surface treatment of the powder with a dispersant is often used. The surface treatment of the dispersant is performed, for example, by dispersing the powder in a dispersing medium in the presence of the dispersant and then heating and drying at a temperature at which the dispersant does not undergo thermal degradation. However, since the dispersant containing a polyalkylene oxide chain as described above is prone to thermal decomposition, the drying temperature cannot be increased, and thus the drying takes time. In addition, other inorganic powder added at the time of surface treatment promotes the thermal decomposition of the dispersant containing a polyalkylene oxide chain. Thus, the dispersant containing a polyalkylene oxide chain has a problem of heat resistance at the time of drying.

[0007] In addition, a polyalkylene oxide compound having an ethylenic unsaturated double bond is used as a raw material of a photocurable resin composition used in paints, coating agents, dry film resists, color resists, inks, adhesives, and the like. For example, Patent Literature 5 reports a photocurable resin composition for a dry film resist, which contains a polyurethane (meth) acrylate having an alkylene oxide group in the molecule. Prior Art Documents Patent Literature

[0008]

Patent Literature 1

Patent Literature 2

Patent Literature 3

Patent Literature 4

Patent Literature 5

[0009] The dispersant containing a polyalkylene oxide chain has insufficient heat resistance at the time of drying. Therefore, one of the objects of the present application is to provide a dispersant which is not easily thermally decomposed in a drying step at the time of surface treatment of a powder, but is easily thermally decomposed in a post-baking step at a higher temperature than the drying step.

[0010] In addition, when a cured film formed from the composition described in Patent Literature 5 is used as a dry film resist for forming a fine line, the adhesion of the cured film to a substrate such as copper or indium tin oxide (ITO) is not sufficient. Therefore, one of the objects of the present application is to provide a photocurable composition which can form a cured film having high adhesion to a substrate. TECHNICAL SOLUTION

[0011] The present inventors have conducted intensive studies in order to achieve the above object, and as a result, have found that a dispersant having a polyoxyalkylene compound having a specific substituent is less likely to thermally decompose in a drying step when surface-treating a powder, and is likely to thermally decompose in a post-curing step at a higher temperature than the drying step. In addition, the present inventors have found that a photocurable composition containing the polyoxyalkylene compound and a photopolymerization initiator can form a cured film having high adhesion to a substrate. Based on these findings, the present invention is as described below. [1] A polyoxyalkylene compound represented by formula (1) and having a weight average molecular weight of 1,000 to 15,000,

[0012] [Chemical Formula 1]

[0013] In formula (1), n represents a number of 1 to 4, a represents a number of 1 to 40, AO represents an oxyalkylene group having a carbon atom number of 2 to 4, when a is a number of 2 or more, 2 or more of the AO are the same as or different from each other, when a is a number of 2 or more and 2 or more of the AO are different from each other, (AO) a has any one of the following structures: a structure of a random copolymer, a structure of a block copolymer, 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 a carbon atom number of 1 to 4, or a substituent X represented by any one of formulae (X1) to (X4),

[0014] [Chemical Formula 2]

[0015] In formulae (X1) to (X4), * represents a bonding site, and Y represents a hydrogen atom or a methyl group, R 1 to R 4 at least one of R when 2 or more of the substituents X are present, 2 or more of the substituents X are the same as or different from each other, and when n is a number of 2 or more, 2 or more of the R 3 are the same as or different from each other. [2] A dispersant composed of the polyoxyalkylene compound or a salt thereof according to the above [1]. [3] A dispersion composition, which is a dispersion composition containing the polyoxyalkylenated compound described in the above [1], a dispersion medium, and a dispersed substance, wherein the content of the dispersion medium is 10 to 1000 parts by mass and the content of the polyoxyalkylenated compound is 0.1 to 100 parts by mass, with respect to 100 parts by mass of the dispersed substance. [4] A photocurable composition characterized by containing the polyoxyalkylenated compound described in the above [1] and a photopolymerization initiator. [5] The photocurable composition described in the above [4], characterized by being used as a coating agent. Effects of the Invention

[0016] According to the present application, a dispersant which is not easily thermally decomposed in a drying step when surface treating a powder, and is easily thermally decomposed in a higher temperature gum removal step than the drying step, can be obtained. Further, according to the present application, a photocurable composition which can form a cured film having high adhesion to a substrate can be obtained. Further, according to the present application, a photocurable composition which can form a cured film having high antifogging effect can be obtained. BRIEF DESCRIPTION OF DRAWINGS

[0017] Figure 1 1 H NMR chart of the compound 1 obtained in Synthesis Example 1. DETAILED DESCRIPTION

[0018] (Polyoxyalkylenated compound) The polyoxyalkylenated compound of the present application is a polyoxyalkylenated compound represented by formula (1):

[0019] [Chemical Formula 3]

[0020] (hereinafter, sometimes referred to simply as "compound (1)") in the present specification. Hereinafter, each symbol in formula (1) will be described in order.

[0021] In formula (1), n represents a number of 1 to 4. The nitrogen atom in compound (1) functions as an adsorption site for the dispersed substance. When n is greater than 4, compound (1) can form a crosslinked structure by adsorbing across the dispersed substance, and as a result, aggregation can occur. n is preferably a number of 2 to 4, and more preferably 2 or 4.

[0022] In formula (1), a is the number of repetitions of AO, and is a number of 1 to 40. From the viewpoint of the dispersing performance of compound (1), a is preferably a number of 3 to 30, and more preferably a number of 8 to 22.

[0023] When compound (1) adsorbs to the dispersed substance, (AO) a ​​function as a steric-hindrance repulsion site, allowing the dispersoid to be dispersed well.

[0024] In formula (1), AO represents an oxyalkylene group having 2 to 4 carbon atoms. AO can be either linear or branched. As AO, for example, an oxyethylene group, an oxypropylene group, an oxybutylene group, or the like can be given. Note that 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).

[0025] When a is a number of 2 or more, 2 or more of AO can be the same or different. When a is a number of 2 or more, and 2 or more of AO are different, the structure of (AO) a can be any one of the following structures: a structure of a random copolymer, a structure of a block copolymer, or a structure having both a random copolymer portion and a block copolymer portion.

[0026] When a is a number of 2 or more, the structure of (AO) a is preferably a structure of a homopolymer or a structure of a block copolymer, more preferably a structure of a diblock copolymer.

[0027] When a is a number of 2 or more, from the viewpoint of dispersing performance of the compound (1), (AO) a is preferably a polyoxyalkylene chain formed of 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 of an oxyethylene group and an oxypropylene group, further preferably a polyoxyalkylene chain having a structure of a diblock copolymer formed of a block of an oxyethylene group and a block of an oxypropylene group. When (AO) a is a polyoxyalkylene chain having the structure of the diblock copolymer, the block of the oxyethylene group is preferably bonded to N in formula (1), and the block of the oxypropylene group is preferably bonded to any one of R 1 to R 4 in formula (1).

[0028] When (AO) a is a polyoxyalkylene chain formed of an oxyethylene group and an oxypropylene group, the molar ratio of the oxyethylene group : the oxypropylene group is preferably 1 : 9 to 6 : 4, more preferably 4 : 6 to 6 : 4.

[0029] In formula (1), R 1 to R 4 each independently represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or a substituent X represented by any one of formula (X1) to formula (X4):

[0030] [Chemical 4]

[0031] * indicates a bonding position, and Y represents a hydrogen atom or a methyl group. Y represents a hydrogen atom or a methyl group. R 1 R 4 at least one of R

[0032] When there are two or more X, the two or more X can be the same as or different from each other, but are preferably the same as each other. When n in formula (1) is two or more, two or more R 3 can be the same as or different from each other, but are preferably the same as each other.

[0033] R 1 R 4 are each independently preferably a hydrogen atom or a substituent represented by any one of formulae (X1) to (X4), more preferably a hydrogen atom or a substituent X represented by formula (X2).

[0034] From the viewpoint of adhesion to a substrate of the compound (1), the proportion of the substituent X in the compound (1) is preferably 0.3 to 0.9, more preferably 0.5 to 0.9. Note that the "proportion of the substituent X" herein means the proportion calculated from the following formula: Proportion of substituent X = (number of substituents X in compound (1)) / (number of R 1 R 4 in the compound (1)).

[0035] The proportion of the substituent X in the compound (1) can be calculated, for example, based on the amount of a raw material used to produce the compound (1). For example, when the compound (1) is produced from an intermediate of a polyoxyalkylene compound in which R 1 R 4 is a hydrogen atom, and a compound (e.g., an isocyanate compound) used for modification of the hydroxyl group of the intermediate and introduction of the substituent X, the proportion of the substituent X in the compound (1) can be calculated from the amounts of the intermediate and the compound added.

[0036] Y in formulae (X1) to (X4) represents a hydrogen atom or a methyl group. From the viewpoints of dispersing properties of the compound (1) and ease of thermal decomposition in a drying step, Y is preferably a methyl group.

[0037] The weight average molecular weight (sometimes referred to simply as "Mw" in the present specification) of the compound (1) is 1,000 to 15,000. If the Mw is less than 1,000 or more than 15,000, the dispersing properties of the compound (1) can decrease. From the viewpoint of the dispersing properties of the compound (1), ease of thermal decomposition in the drying step, and ease of thermal decomposition in the gum removal step, the Mw is preferably 4,000 to 10,000. Note that, in the present specification, the "weight average molecular weight" refers to the weight average molecular weight converted using a standard polyethylene glycol by gel permeation chromatography (GPC) using N,N-dimethylformamide (DMF) as the eluent.

[0038] The compound (1) can be produced by modifying the hydroxyl group of a polyoxyalkylene compound in which R 1 ~R 4 in formula (1) is a hydrogen atom with an isocyanate compound, an acid anhydride, or a halide, etc. containing an olefinically unsaturated double bond to introduce a substituent X.

[0039] The compound (1) can be produced by modifying the hydroxyl group of a polyoxyalkylene compound in which R 1 ~R 4 in formula (1) is a hydrogen atom with an isocyanate compound, an acid anhydride, or a halide, etc. containing an olefinically unsaturated double bond to introduce a substituent X. As the catalyst that can be used for the addition reaction of the alkylene oxide, for example, an alkaline catalyst, a Lewis acid catalyst can be given. As the alkaline catalyst, for example, an oxide of an alkali metal or an alkaline earth metal, a hydroxide of an alkali metal or an alkaline earth metal, an alkoxide, an alkylamine such as triethylamine, an alkanolamine such as triethanolamine can be given. As the Lewis acid catalyst, for example, boron trifluoride, tin tetrachloride can be given. The amount of the catalyst used is usually 0.01 to 5.0% by mass with respect to the mass of the reaction product after the addition reaction. The addition reaction of the alkylene oxide can be performed, for example, by continuously pressurizing the alkylene oxide and adding it to the polyethylene polyamine having 2 to 5 nitrogen atoms as the raw material, in an inert atmosphere of argon or nitrogen, etc., at 50 to 200°C and 0.02 to 1.0 MPa, as necessary in the presence of a catalyst. Alternatively, the reaction product after the addition reaction of the alkylene oxide can be reacted with an alkyl halide having 1 to 4 carbon atoms in the presence of an alkaline catalyst, as necessary, to introduce an alkyl group having 1 to 4 carbon atoms into a part of the reaction product.

[0040] As the compound which modifies the hydroxyl group of the polyoxyalkylenated compound and introduces the substituent X, for example, isocyanate compounds, acid anhydrides, halides can be given. As the isocyanate compounds, for example, 2-isocyanatoethyl acrylate, 2-isocyanatoethyl methacrylate, 1,1-(bisacryloyloxymethyl)ethyl isocyanate, and 2-(2-methylacryloyloxyethoxy)ethyl isocyanate, and the like can be given. As the acid anhydrides, for example, acrylic anhydride, methacrylic anhydride, and the like can be given. As the halides, for example, acryloyl chloride, methacryloyl chloride, and the like can be given.

[0041] (Dispersant) The present application provides a dispersant composed of the compound (1) or a salt thereof (preferably a dispersant composed of the compound (1)). The dispersant of the present application can be used singly or in combination of two or more. In addition, the dispersant of the present application can be used in combination with other dispersants or additives.

[0042] The acid which forms the salt of the compound (1) can be any of an organic acid or an inorganic acid, or a mixture of an organic acid and an inorganic acid. As the organic acid, for example, acetic acid, glycolic acid, oxalic acid, citric acid, lactic acid, malic acid, acrylic acid, methacrylic acid, and the like can be given. As the inorganic acid, for example, hydrochloric acid, nitric acid, sulfuric acid, phosphoric acid, and the like can be given. Any of the organic acid or the inorganic acid can be used singly or in combination of two or more.

[0043] (Dispersion composition) The present application provides a dispersion composition containing the compound (1), a dispersion medium, and a dispersed substance. Any of the compound (1), the dispersion medium, and the dispersed substance can be used singly or in combination of two or more.

[0044] The content of the compound (1) in the dispersion composition of the present application (the total content when two or more compounds (1) are used) with respect to 100 parts by mass of the dispersed substance is preferably 0.1 to 100 parts by mass, more preferably 0.5 to 50 parts by mass, and further preferably 1 to 30 parts by mass. If the content is less than 0.1 parts by mass, the dispersed substance can not be sufficiently dispersed, and even if the content is more than 100 parts by mass, an effect commensurate with the content can not be obtained.

[0045] As the dispersed substance, for example, organic powders, inorganic powders can be given. Any of the organic powders and the inorganic powders can be used singly or in combination of two or more. In addition, a mixture of the organic powders and the inorganic powders can be used.

[0046] As the organic powder, for example, organic pigments such as azo pigments, heavy azo pigments, condensed azo pigments, thioindigo pigments, indanthrone pigments, quinacridone pigments, anthraquinone pigments, benzimidazolone pigments, perylene pigments, phthalocyanine pigments, anthrapyridine pigments, and dioxazine pigments can be given.

[0047] As the inorganic powder, for example, metal powders such as iron, aluminum, chromium, nickel, cobalt, zinc, tungsten, indium, tin, palladium, zirconium, titanium, copper, silver, gold, and platinum; alloy powders composed of two or more kinds of metals; powders of composites composed of a metal and a non-metal; and powders of composites composed of a metal and an alloy powder can be given.

[0048] Further, as the inorganic powder, for example, powders of silicate minerals, other silicate compounds, carbonate compounds, sulfate compounds, hydroxide, oxide, nitride, carbide, titanate compounds, and the like can be given. As specific examples, 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 fibers, carbon fibers, carbon nanofibers, carbon nanotubes (single-walled nanotubes, double-walled nanotubes, multi-walled nanotubes), and the like can be given.

[0049] The content of the dispersoid in the dispersion composition of the present application (the total content when two or more kinds of dispersoids are used) with respect to the entire dispersion composition is preferably 1 to 75% by mass, more preferably 9 to 75% by mass.

[0050] As the dispersion medium, either water or an organic solvent can be used, and an organic solvent is preferred. As the organic solvent, for example, aromatic hydrocarbon-based solvents such as toluene and xylene, hydrocarbon-based solvents such as cyclohexane, ketone-based solvents such as acetone and methyl ethyl ketone, ester-based solvents such as ethyl acetate and n-propyl acetate, glycol ether-based solvents such as ethylene glycol monoethyl ether and ethylene glycol monoisopropyl ether, glycol ether ester-based solvents such as ethylene glycol monoethyl ether acetate and propylene glycol monomethyl ether acetate, terpene-based solvents such as terpineol, dihydroterpineol, and dihydroterpineol acetate, and alcohol-based solvents such as methanol, ethanol, and isopropyl alcohol can be given.

[0051] The content of the dispersion medium in the dispersion composition of the present application (the total content when two or more kinds of dispersion media are used) with respect to 100 parts by mass of the dispersoid is preferably 10 to 1000 parts by mass, more preferably 10 to 900 parts by mass, and further preferably 30 to 900 parts by mass.

[0052] The dispersion composition of the present application can contain various additives other than the dispersant of compound (1), such as a binder, a plasticizer, an antifoaming agent, and the like, within a range not impairing the effects of the present application.

[0053] The dispersion composition of the present application can contain an acid that forms a salt with compound (1), and compound (1) can exist in the dispersion composition of the present application as a salt. As the acid that forms a salt with compound (1), the above-mentioned substances can be given.

[0054] The dispersion composition of the present application, for example, can be produced by a method in which a dispersoid is added to a mixture of compound (1) and a dispersion medium, and the resulting mixture is stirred and mixed at room temperature; or a method in which the dispersion medium and compound (1) are added to a dispersoid, and stirred and mixed at room temperature. The stirring, mixing, or dispersing can use a publicly known device. As the publicly known device, for example, a mixing stirrer, a roll mill, a ball mill, a bead mill, a sand mill, a homogenizer, a disperser, a planetary stirrer, and the like can be given. In addition, an ultrasonic bath can also be used to perform a dispersion treatment of a mixture containing compound (1), a dispersion medium, and a dispersoid, to produce the dispersion composition of the present application.

[0055] (Photo-curable composition) The present application provides a photo-curable composition containing compound (1) and a photopolymerization initiator. Compound (1) and the photopolymerization initiator can each be used only one kind, or two or more kinds can be used in combination.

[0056] From the viewpoint of the coating properties on a substrate and the antifogging effect, the content of compound (1) in the photo-curable composition of the present application (the total content when two or more kinds of compound (1) are used) is preferably 10 to 90% by mass, more preferably 30 to 80% by mass, and further preferably 50 to 70% by mass, relative to the total photo-curable composition.

[0057] The photopolymerization initiator is not particularly limited, and a publicly known photopolymerization initiator can be used. As the publicly known photopolymerization initiator, for example, the following substances can be given: 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-methylpropanoyl)benzyl]phenyl]-2-methylpropan-1-one, 2-methyl-1-[4-(methylthio)]phenyl]-2-morpholinopropan-1-one, 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)butan-1-one, 2-dimethylamino-2-(4-methylbenzyl)-1-(4-morpholin-4-ylphenyl)butan-1-one, 3,6-bis(2-methyl-2-morpholinopropanoyl)-9-n-octylcarbazole, and the like benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether, and the like benzoin compounds; benzoin, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether, and the like benzoin compounds; benzophenone, 2-methylbenzophenone, 3-methylbenzophenone, 4-methylbenzophenone, 2,4,6-trimethylbenzophenone, 4-phenylbenzophenone, methyl-2-benzophenone, 1-[4-(4-benzoylphenylsulfanyl)phenyl]-2-methyl-2-(4-methylphenylsulfonyl)propan-1-one, 4,4'-bis(dimethylamino)benzophenone, 4,4'-bis(diethylamino)benzophenone, and 4-methoxy-4'-dimethylaminobenzophenone, and the like benzophenone compounds; bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide, 2,4,6-trimethylbenzoyldiphenylphosphine oxide, bis(2,6-dimethoxybenzoyl)-2,4,4-trimethylpentylphosphine oxide, and the like acylophosphine oxide compounds; thioxanthone, 2-chlorothioxanthone, 2,4-diethylthioxanthone, isopropylthioxanthone, 1-chloro-4-propylthioxanthone, 3-[3,4-dimethyl-9-oxo-9H-thioxanthen-2-yl-oxy]-2-hydroxypropyl-N,N,N-trimethylammonium chloride, and fluorothioxanthone, and the like thioxanthone compounds.

[0058] From the viewpoint of adhesion to a substrate and antifogging effect, the content of the photopolymerization initiator in the photocurable composition of the present application (the total content when two or more kinds of photopolymerization initiators are used) is preferably 0.5 to 5.0% by mass, more preferably 1.0 to 4.0% by mass, and further preferably 1.5 to 3.0% by mass, relative to the total photocurable composition.

[0059] The photocurable composition of the present application can contain one or two or more solvents. The solvent is preferably an organic solvent. As the organic solvent, for example, aromatic hydrocarbon-based solvents such as toluene, xylene and the like, hydrocarbon-based solvents such as cyclohexane and the like, ketone-based solvents such as acetone, methyl ethyl ketone and the like, ester-based solvents such as ethyl acetate, n-propyl acetate and the like, glycol ether-based solvents such as ethylene glycol monoethyl ether, ethylene glycol monoisopropyl ether and the like, glycol ether ester-based solvents such as ethylene glycol monoethyl ether acetate, propylene glycol monomethyl ether acetate and the like, terpene-based solvents such as terpineol, dihydromyrcenol, dihydromyrcenol acetate and the like, alcohol-based solvents such as methanol, ethanol, isopropyl alcohol and the like can be mentioned.

[0060] When a solvent is used, from the viewpoint of the coatability to a substrate and the antifogging effect, the content of the solvent in the photocurable composition of the present application (when two or more solvents are used, the total content of these) is preferably 10 to 90% by mass, more preferably 20 to 70% by mass, and further preferably 30 to 50% by mass, based on the total photocurable composition.

[0061] The photocurable composition of the present application can contain an additive other than the compound (1), the photopolymerization initiator and the solvent, within a range not impairing the effects of the present application. As the additive, for example, pigments, colorants, thickeners, sensitizers, defoaming agents, leveling agents, antioxidants, plasticizers, antistatic agents and the like can be mentioned. Each of the additives can be used alone or two or more of them can be used in combination.

[0062] The photocurable composition of the present application can contain an acid forming a salt with the compound (1), and the compound (1) can exist as a salt in the photocurable composition of the present application. As the acid forming a salt with the compound (1), the above-mentioned substances can be mentioned.

[0063] The photocurable composition of the present application can be prepared by mixing the compound (1) and the photopolymerization initiator. The mixing can be carried out using a publicly known device. As the publicly known device, for example, mixing stirrers, roll mills, ball mills, bead mills, sand mills, homogenizers, dispersers, planetary stirrers and the like can be mentioned.

[0064] The photocurable composition of the present application is preferably used as a coating agent (particularly, a coating agent for forming a cured film having an antifogging effect). EXAMPLE

[0065] The present application will be more specifically described below by way of Examples, but the present application is not limited to the following Examples, and can be appropriately modified within the scope of the above or below-mentioned gist, and these are also included in the technical scope of the present application. In addition, "%" described below means "mass %".

[0066] The identification of compounds 1-9 obtained from the following synthetic examples 1-9 was performed using gel permeation chromatography (GPC) and nuclear magnetic resonance spectrometry (NMR). 1 The H NMR was performed.

[0067] The following shows the determination conditions for gel permeation chromatography (GPC). Device: HLC-8420GPC manufactured by Tosoh Corporation Column: TSKgel SuperAW3000+2500 manufactured by Tosoh Corporation Eluent: DMF containing 30 mmol / L LiBr and 50 mmol / L triethylamine Flow rate: 1.0 mL / min Detector: Differential refractometer (RI) Temperature: 40℃ Standard: Polyethylene Glycol Sample: Inject 100 μL of a 0.1% by mass DMF solution.

[0068] The following shows 1 Measurement conditions for H NMR. Device: JNM-ECA-600 manufactured by Nippon Electronics Co., Ltd. Solvent: Deuterated chloroform Standard: Tetramethylsilane Temperature: 25℃

[0069] The results obtained by analyzing the above measurement conditions 1 The formation of the target product can be confirmed by the ¹H NMR spectrum. For example, in the case of compound 1, the formation of compound 1 can be confirmed by the disappearance of the hydrogen addition peak (δ5.64ppm, 6.19ppm) on the carbon-carbon double bond of the methacryloyl group of 2-isocyanoethyl methacrylate, and the formation of the hydrogen addition peak (δ5.59ppm, 6.12ppm) on the carbon-carbon double bond of the methacryloyl group, which is part of substituent X of compound 1.

[0070] (Synthetic Example 1: Comparison of the synthesis of compound 1 (intermediate 1) and compound 1) To a 5 liter stainless steel pressure vessel equipped with a stirrer, pressure gauge, thermometer, safety valve, gas inlet tube, gas outlet tube, cooling coil, and steam jacket, was added diethylenetriamine: 51.6 g (0.5 mol), and the system was replaced with nitrogen. After warming to 80°C with stirring, ethylene oxide: 110 g (2.5 mol, 1 mol per 1 mol of active hydrogen atoms bonded to nitrogen atoms in diethylenetriamine) was added from another pressure vessel by pressurizing with nitrogen gas through the gas inlet tube at 80 to 100°C and 0.05 to 0.5 MPa (gauge pressure). After the addition was completed, the reaction was continued under the same conditions until the internal pressure reached a constant value. After cooling to 40°C, potassium hydroxide: 12.1 g was added, and the system was replaced with nitrogen. After warming to 100°C with stirring, propylene oxide: 2400 g (41.3 mol, 13 mol per 1 mol of active hydrogen atoms bonded to nitrogen atoms in diethylenetriamine) was added from another pressure vessel by pressurizing with nitrogen gas through the gas inlet tube at 100 to 120°C and 0.05 to 0.5 MPa. After the addition was completed, the reaction was continued under the same conditions until the internal pressure reached a constant value. After cooling to 30°C, the reaction product was removed from the pressure vessel and placed in a 5 liter flask. To this was added 40 g of an adsorbent (trade name: Kyowaad 700, manufactured by Kyowa Chemical Industries, Ltd.), and the resulting salt and adsorbent were separated by filtration under a nitrogen atmosphere at 90 to 100°C and 0.05 MPa or less to obtain comparative compound 1 (intermediate 1). The molecular weight of comparative compound 1 (intermediate 1) was measured by GPC, and the result was that the weight average molecular weight was 6500.

[0071] Subsequently, to a 0.3 liter flask equipped with a stirrer, thermometer, and air inlet tube was added comparative compound 1 (intermediate 1): 130.0 g, 1,4-naphthoquinone: 0.02 g, dibutyltin dilaurate: 0.01 g, and 2-isocyanatoethyl methacrylate: 9.3 g (0.06 mol), and stirred for 4 hours. Thus, substituent X was introduced into comparative compound 1 (intermediate 1) to obtain compound 1. The molecular weight of compound 1 was measured by GPC, and the result was that the weight average molecular weight was 6700. The molecular weight distribution of compound 1 was measured by GPC, and the result was that the polydispersity index was 1.2. 1 The H NMR spectrum was as shown in Figure 1The ratio of the substituent X of 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 (5) bonded to the nitrogen atom thereof, the amount of charge (130.0 g), and the amount of charge of 2-isocyanatoethyl methacrylate (0.06 mol). The ratio of the substituent X of the following compounds 2 to 9 was also calculated in the same manner as the ratio of the substituent X of compound 1.

[0072] (Synthetic Example 2: Synthesis of compound 2) To a 0.3 liter flask equipped with a stirrer, a thermometer, and an air inlet tube were added comparative compound 1 (intermediate 1): 130.0 g, 1,4-naphthoquinone: 0.02 g, dibutyltin dilaurate: 0.01 g, and 2-isocyanatoethyl methacrylate: 12.4 g (0.08 mol), and stirred for 4 hours to obtain compound 2. The molecular weight of compound 2 was measured by GPC, and the result was that the weight average molecular weight thereof was 6800.

[0073] (Synthetic Example 3: Synthesis of intermediate 2 and compound 3) To a 5 liter stainless steel pressure vessel equipped with a stirrer, a pressure gauge, a thermometer, a safety valve, a gas inlet tube, a gas outlet tube, a cooling coil, and a steam jacket, tetraethylenepentamine: 94.7 g (0.5 mol) was charged, and the inside of the system was replaced with nitrogen. After the temperature was raised to 80°C with stirring, ethylene oxide: 154 g (3.5 mol, 1 mol per 1 mol of active hydrogen atoms bonded to the nitrogen atoms of tetraethylenepentamine) was added from another pressure vessel prepared beforehand through the gas inlet tube by pressurizing with nitrogen at 80 to 100°C and 0.05 to 0.5 MPa (gauge pressure). After the addition was completed, the reaction was continued under the same conditions until the internal pressure reached a constant value. After cooling to 40°C, potassium hydroxide: 10.0 g was added, and the inside of the system was replaced with nitrogen. After the temperature was raised to 100°C with stirring, propylene oxide: 1130 g (25.7 mol, 8 mol per 1 mol of active hydrogen atoms bonded to the nitrogen atoms of tetraethylenepentamine) was added from another pressure vessel prepared beforehand through the gas inlet tube by pressurizing with nitrogen at 100 to 120°C and 0.05 to 0.5 MPa. After the addition was completed, the reaction was continued under the same conditions until the internal pressure reached a constant value. Subsequently, propylene oxide: 1980 g (41.3 mol, 13 mol per 1 mol of active hydrogen atoms bonded to the nitrogen atoms of tetraethylenepentamine) was added from another pressure vessel prepared beforehand through the gas inlet tube by pressurizing with nitrogen at 100 to 120°C and 0.05 to 0.5 MPa. After the addition was completed, the reaction was continued under the same conditions until the internal pressure reached a constant value. After cooling to 30°C, the reaction product was taken out of the pressure vessel and put into a 5 liter flask. To this was added 34 g of an adsorbent (trade name: Kyowaad 700, manufactured by Kyowa Chemical Industries, Ltd.), and the resulting salt and adsorbent were separated by filtration under a nitrogen atmosphere at 90 to 100°C and 0.05 MPa or less to obtain intermediate 2. The molecular weight of intermediate 2 was measured by GPC, and the result was that the weight average molecular weight thereof was 5500.

[0074] Subsequently, to a 0.3 liter flask equipped with a stirrer, a thermometer, and an air inlet tube, intermediate 2: 110.0 g, 1,4-naphthoquinone: 0.02 g, dibutyltin dilaurate: 0.01 g, and 2-isocyanatoethyl methacrylate: 8.7 g (0.06 mol) were added, and stirring was performed for 4 hours to obtain compound 3. The molecular weight of compound 3 was measured by GPC, and the result was that the weight average molecular weight thereof was 5700.

[0075] (Synthesis Example 4: Synthesis of compound 4) To a 0.3 liter flask equipped with a stirrer, thermometer, air introducing tube, was added intermediate 2: 110.0 g, 1,4-naphthoquinone: 0.02 g, dibutyl tin dilaurate: 0.01 g, 2-isocyanatoethyl methacrylate: 13.0 g (0.08 mol), and stirred for 4 hours to obtain compound 4. The molecular weight of compound 4 was measured by GPC, and the result was that the weight average molecular weight thereof was 5900.

[0076] (Synthetic Example 5: Synthesis of compound 5) To a 0.3 liter flask equipped with a stirrer, thermometer, air introducing tube, was added intermediate 2: 110.0 g, 1,4-naphthoquinone: 0.02 g, dibutyl tin dilaurate: 0.01 g, 2-isocyanatoethyl methacrylate: 17.4 g (0.11 mol), and stirred for 4 hours to obtain compound 5. The molecular weight of compound 5 was measured by GPC, and the result was that the weight average molecular weight thereof was 6100.

[0077] (Synthetic Example 6: Synthesis of intermediate 3 and compound 6) To a 5 liter stainless steel pressure vessel equipped with a stirrer, a pressure gauge, a thermometer, a safety valve, a gas inlet tube, a gas outlet tube, a cooling coil, and a steam jacket, was added diethylenetriamine: 51.6 g (0.5 mol), and the system was replaced with nitrogen. After the temperature was raised to 80°C with stirring, ethylene oxide: 110 g (2.5 mol, 1 mol per 1 mol of active hydrogen atoms bonded to the nitrogen atoms of diethylenetriamine) was added from another pressure vessel prepared beforehand through the gas inlet tube by pressurizing with nitrogen at 80 to 100°C and 0.05 to 0.5 MPa (gauge pressure). After the addition was completed, the reaction was continued under the same conditions until the internal pressure reached a constant value. After cooling to 40°C, potassium hydroxide: 7.8 g was added, and the system was replaced with nitrogen. After the temperature was raised to 100°C with stirring, propylene oxide: 240 g (5.4 mol, 2 mol per 1 mol of active hydrogen atoms bonded to the nitrogen atoms of diethylenetriamine) was added from another pressure vessel prepared beforehand through the gas inlet tube by pressurizing with nitrogen at 100 to 120°C and 0.05 to 0.5 MPa. After the addition was completed, the reaction was continued under the same conditions until the internal pressure reached a constant value. Subsequently, propylene oxide: 2210 g (38.0 mol, 13 mol per 1 mol of active hydrogen atoms bonded to the nitrogen atoms of diethylenetriamine) was added from another pressure vessel prepared beforehand through the gas inlet tube by pressurizing with nitrogen at 100 to 120°C and 0.05 to 0.5 MPa. After the addition was completed, the reaction was continued under the same conditions until the internal pressure reached a constant value. After cooling to 30°C, the reaction product was taken out of the pressure vessel and put into a 5 liter flask. To this was added 26 g of an adsorbent (trade name: Kyowaad 700, manufactured by Kyowa Chemical Industries, Ltd.), and the resulting salt and adsorbent were separated by filtration under a nitrogen atmosphere at 90 to 100°C and 0.05 MPa or less to obtain intermediate 3. The molecular weight of intermediate 3 was measured by GPC, and the result was that the weight average molecular weight thereof was 4300.

[0078] Subsequently, to a 0.3 liter flask equipped with a stirrer, a thermometer, and an air inlet tube was added intermediate 3: 86.0 g, 1,4-naphthoquinone: 0.02 g, dibutyltin dilaurate: 0.01 g, and 2-isocyanatoethyl methacrylate: 12.4 g (0.08 mol), and stirring was performed for 4 hours to obtain compound 6. The molecular weight of compound 6 was measured by GPC, and the result was that the weight average molecular weight thereof was 4400.

[0079] (Synthesis Example 7: Synthesis of intermediate 4 and compound 7) To a 5 liter stainless steel pressure vessel equipped with a stirrer, a pressure gauge, a thermometer, a safety valve, a gas inlet tube, a gas outlet tube, a cooling coil, and a steam jacket, tetraethylenepentamine: 56.8 g (0.3 mol) was charged, and the inside of the system was replaced with nitrogen. After the temperature was raised to 80°C with stirring, 1,2-epoxybutane: 150 g (2.1 mol, 1 mol per 1 mol of active hydrogen atom bonded to the nitrogen atom of tetraethylenepentamine) was added from another pressure vessel prepared beforehand through the gas inlet tube by pressurizing with nitrogen at 80 to 100°C and 0.05 to 0.5 MPa (gauge pressure). After the addition was completed, the reaction was continued under the same conditions until the internal pressure reached a constant value. After cooling to 40°C, potassium hydroxide: 8.5 g was added, and the inside of the system was replaced with nitrogen. After the temperature was raised to 100°C with stirring, 1,2-epoxybutane: 2630 g (36.5 mol, 14 mol per 1 mol of active hydrogen atom bonded to the nitrogen atom of tetraethylenepentamine) was added through the gas inlet tube by pressurizing with nitrogen at 100 to 120°C and 0.05 to 0.5 MPa. After the addition was completed, the reaction was continued under the same conditions until the internal pressure reached a constant value. After cooling to 30°C, the reaction product was taken out of the pressure vessel and put into a 5 liter flask. To this was added 29 g of an adsorbent (trade name: Kyowaad 700, manufactured by Kyowa Chemical Industries, Ltd.), and the resulting salt and adsorbent were separated by filtration under a nitrogen atmosphere at 90 to 100°C and 0.05 MPa or less to obtain intermediate 4. The molecular weight of intermediate 4 was measured by GPC, and the result was that the weight average molecular weight thereof was 5800.

[0080] Subsequently, to a 0.3 liter flask equipped with a stirrer, a thermometer, and an air inlet tube, intermediate 4: 156.0 g, 1,4-naphthoquinone: 0.02 g, dibutyltin dilaurate: 0.01 g, and 2-isocyanatoethyl methacrylate: 17.6 g (0.11 mol) were added, and stirring was performed for 4 hours to obtain compound 7. The molecular weight of compound 7 was measured by GPC, and the result was that the weight average molecular weight thereof was 6200.

[0081] (Synthetic Example 8: Synthesis of Compound 8) Subsequently, to a 0.3 liter flask equipped with a stirrer, a thermometer, and an air inlet tube, intermediate 4: 156.0 g, 1,4-naphthoquinone: 0.02 g, dibutyltin dilaurate: 0.01 g, and 2-isocyanatoethyl methacrylate: 17.6 g (0.11 mol) were added, and stirring was performed for 4 hours to obtain compound 7. The molecular weight of compound 7 was measured by GPC, and the result was that the weight average molecular weight thereof was 6200.

[0082] (Synthetic Example 9: Synthesis of Compound 9) To a 0.3 liter flask equipped with a stirrer, thermometer, air inlet tube, comparative compound 1 (intermediate 1) : 130.0 g, 1,4-naphthoquinone: 0.02 g, dibutyltin dilaurate: 0.01 g, 2-isocyanatoethyl acrylate: 11.3 g (0.08 mol) were added, and stirring was carried out for 4 hours to obtain compound 9. The molecular weight of compound 9 was measured by GPC, and the result was that the weight average molecular weight thereof was 6800.

[0083] The n, (AO) a , R 1 ~ R 4 in the formula (1) of the compounds 1 to 9 or comparative compound 1 (intermediate 1) obtained above, the kind of the formula of the substituent X (and Y), and R 1 ~ R 4 other than the substituent X, the weight average molecular weight (Mw), and the proportion of the substituent X are shown in Table 1.

[0084] [Table 1]

[0085] <Examples 1 to 9 and Comparative Example 1> The compounds 1 to 9 were used as dispersants of Examples 1 to 9, and comparative compound 1 (intermediate 1) was used as a dispersant of Comparative Example 1, and whether or not there was sedimentation and shear viscosity was measured, and their dispersing properties were evaluated as follows.

[0086] In addition, the easiness of thermal decomposition in the drying step (hereinafter, referred to as "heat resistance in the drying step") and the easiness of thermal decomposition in the gum removal step (hereinafter, referred to as "thermal decomposition in the gum removal step") 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.

[0087] <Evaluation of dispersing properties> (Shear viscosity) In Examples 1 to 9 or Comparative Example 1, to a 50 mL sample bottle, silver powder (manufactured by Toho Zinc Co., Ltd., product name: SPQ03R) 2.0 g, liquid mixture containing α-terpineol (manufactured by Obayashi Chemical Industries, Ltd., product name: α-terpineol (deer first grade)) 0.67 g, and dispersant 0.02 g were added, and using a mixing blender, the powder was pulverized for 5 minutes at a rotation speed of 2000 rpm to prepare a dispersed composition. In Reference Example 1, in addition to not using a dispersant, a dispersed composition was prepared in the same manner as in Examples 1 to 7 or Comparative Example 1. The shear viscosity of the obtained dispersed composition at 20°C at a shear rate of 10 (1 / s) was measured using a rheometer, and evaluation was carried out according to the following criteria. The results are shown in Table 2. (Evaluation criteria) ◎: Shear viscosity is 0.60 Pa-s or less O: Shear viscosity is more than 0.60 Pa-s, 1.50 Pa-s or less X: Shear viscosity is more than 1.50 Pa-s.

[0088] (Sedimentation) In Examples 1 to 9 or Comparative Example 1, to a 50 mL sample bottle, silver powder (manufactured by Mitsui Mining Co., Ltd., product name: SPQ03R) 1.0 g, a liquid mixture containing a-terpineol (manufactured by Kanto Chemical Co., Inc., product name: a-terpineol (deer first class), containing a small amount of β-terpineol and γ-terpineol) 9.0 g, and a dispersant 0.03 g were added, and the powder was pulverized by mixing with a mixing blender at a rotation speed of 2000 rpm for 5 minutes to prepare a dispersion composition. In Reference Example 1, the same dispersion composition as in Examples 1 to 7 or Comparative Example 1 was prepared except that no dispersant was used. After the obtained dispersion composition was left to stand for 30 minutes, the presence or absence of sedimentation of the silver powder in the dispersion composition was visually confirmed, and the evaluation was performed according to the following criteria. The results are shown in Table 2. (Evaluation Criteria) O: No sedimentation X: Sedimentation

[0089] <Thermal resistance in drying step> The thermal resistance of the dispersants of Examples 1 to 9 (i.e., Compounds 1 to 9) and Comparative Example 1 (i.e., Comparative Compound 1 (Intermediate 1)) in the drying step was evaluated as follows. In the thermogravimetric (TG) measurement, the weight loss of the dispersant when kept at 200°C in air for 30 minutes was measured. Based on the initial weight before the thermogravimetric measurement and the weight loss, the following formula was used: Weight loss rate (%) = (weight loss (g) / initial weight (g)) x 100 The weight loss rate was calculated, and the evaluation was performed according to the following criteria. The results are shown in Table 2. The smaller the weight loss rate, the better the thermal resistance in the drying step. (Evaluation Criteria) ◎: 10% or less O: More than 10%, 75% or less X: More than 75%

[0090] <Thermal decomposition in gum removal step> The thermal decomposition of the dispersants of Examples 1 to 9 (i.e., Compounds 1 to 9) and Comparative Example 1 (i.e., Comparative Compound 1 (Intermediate 1)) in the gum removal step was evaluated as follows. In the thermogravimetric (TG) measurement, the weight loss of the dispersant when kept at 400°C in air for 30 minutes was measured. Based on the initial weight before the thermogravimetric measurement and the weight loss, the following formula was used: Weight reduction rate (%) = (weight reduction (g) / initial weight (g)) x 100 The weight reduction rate was calculated, and evaluated according to the following criteria. The results are shown in Table 2. The greater the weight reduction rate, the better the thermal decomposability in the gum removal step. (Evaluation Criteria) O: 95% or more X: less than 95%

[0091]

Table 2

[0092] As shown in Table 2, the dispersing performance, the heat resistance in the drying step, and the thermal decomposability in the gum removal step of the dispersants of Examples 1 to 9 (i.e., compounds 1 to 9) were excellent. On the other hand, the dispersant of Comparative Example 1 (i.e., comparative compound 1 (intermediate 1)) was insufficient in the heat resistance in the drying step.

[0093] As apparent from the above Examples 1 to 9 and Comparative Example 1, the dispersant of the present application is a dispersant excellent in the dispersing performance, the heat resistance in the drying step, and the thermal decomposability in the gum removal step.

[0094] <Examples 10 to 18 and Comparative Example 2> In Examples 10 to 18, a photocurable composition containing any one of compounds 1 to 9 and a photopolymerization initiator was prepared. In Comparative Example 2, instead of compounds 1 to 9, Blemmer DA-800AU (manufactured by Nippon Oil & Fats Corporation, a polyoxyalkylenated compound having an ethylenic unsaturated double bond) was used to prepare a photocurable composition.

[0095] Specifically, in a 50 mL sample bottle, 5.0 g of any one of compounds 1 to 9 or Blemmer DA-800AU, 0.15 g of 1-hydroxycyclohexyl phenyl ketone (manufactured by BASF Corporation, Irgacure 184) as a photopolymerization initiator, and 2.5 g of propylene glycol monomethyl ether acetate as a solvent were weighed, mixed until the system became uniform, and a solution-like photocurable composition was prepared.

[0096] <Evaluation of Adhesion of Cured Film> 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 the substrate on which the dried coating film was formed was put into an inert gas tank, and nitrogen gas was replaced for 2 minutes. Then, using a UV irradiation device (manufactured by Fusion UV Systems Corporation), irradiation was performed at a cumulative light amount of 900 mJ / cm 2The obtained photocurable composition was dropped on a glass substrate of 5 cm x 5 cm, and a coating film was formed on the entire surface of the glass substrate using a spin coater. After drying the obtained coating film at 80°C for 5 minutes, the occurrence of shrinkage cavity in the coating film was visually confirmed, and the coatability was evaluated by the following criteria. The results are shown in Table 3. (Evaluation Criteria) ◎: 10 or more of the remaining cured film O: 5 or more and less than 9 of the remaining cured film X: less than 4 of the remaining cured film

[0097] <Coatability of photocurable composition> The obtained photocurable composition was dropped on a glass substrate of 5 cm x 5 cm, and a coating film was formed on the entire surface of the glass substrate using a spin coater. After drying the obtained coating film at 80°C for 5 minutes, the occurrence of shrinkage cavity in the coating film was visually confirmed, and the coatability was evaluated by the following criteria. The results are shown in Table 3. (Evaluation Criteria) O: no shrinkage cavity was generated in the coating film, and a uniform coating film was formed on the entire surface of the substrate X: shrinkage cavity was generated in the coating film, and a part of the substrate was exposed

[0098] <Evaluation of antifogging effect of cured film> The substrate on which the dried coating film was formed obtained in the <Evaluation of coatability of photocurable composition> was put in an inert gas tank, and nitrogen gas was replaced for 2 minutes. Then, using a UV irradiation device (manufactured by Fusion UV Systems), UV irradiation was performed under conditions of an accumulated light amount of 900 mJ / cm 2 A cured film having a thickness of 20 μm was produced. The produced cured film was set at a height of 6 cm from the surface of warm water at 50°C with the cured film facing downward, and the occurrence of fogging in the cured film after 1 minute was visually confirmed, and the antifogging effect was evaluated according to the following criteria. The results are shown in Table 3. Note that the same evaluation of antifogging effect was performed using a glass substrate on which no photocurable composition was coated, and as a result, fogging occurred. (Evaluation Criteria) O: fogging occurred X: no fogging occurred

[0099] [Table 3]

[0100] As is clear from the results shown in Table 3, the photocurable composition of the present application has excellent coatability, and a cured film having high adhesion to a substrate and having an antifogging effect can be formed using the composition. [Industrial Applicability]

[0101] The compound (1) of the present application is useful as a dispersant. In addition, the photocurable composition of the present application containing the compound (1) and a photopolymerization initiator is useful as a coating agent.

[0102] This application is based on Japanese Patent Application No. 2023-053387 filed in Japan, the contents of which are incorporated herein in its entirety.

Claims

1. A polyoxyalkylene compound, characterized by, which is represented by formula (1), and has a weight average molecular weight of 1,000 to 15,000, in formula (1), n represents a number of 1 to 4, a represents a number of 1 to 40, AO represents an oxyalkylene group having 2 to 4 carbon atoms, when a is a number of 2 or more, 2 or more AO's are the same or different from each other, a is a number of 2 or more, and when 2 or more of AO are not the same as each other, (AO) a the structure of the copolymer is any one of the following structures: a structure of a random copolymer, a structure of a block copolymer, or a structure having both a random copolymer portion and a block copolymer portion, R 1 ~R 4 each independently represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or a substituent group X represented by any one of formulae (X1) to (X4): in formula (X1) to formula (X4), * indicates a bonding position, and Y represents a hydrogen atom or a methyl group; R 1 ~R 4 at least one of R is a substituent X, when 2 or more X's are present, 2 or more X's are the same or different from each other, and n is a number of 2 or more, 2 or more R 3 are the same as or different from each other.

2. A dispersant characterized by, consisting of the polyoxyalkylene compound or a salt thereof according to claim 1.

3. A dispersion composition which is a dispersion composition containing the polyoxyalkylenated compound according to claim 1, a dispersion medium, and a dispersed substance, wherein, The content of the dispersing medium is 10 to 1,000 parts by mass, and the content of the polyoxyalkylene compound is 0.1 to 100 parts by mass, with respect to 100 parts by mass of the dispersoid.

4. A photocurable composition, characterized by comprising: containing the polyoxyalkylene compound according to claim 1 and a photopolymerization initiator.

5. The photocurable composition according to claim 4, characterized by for use as a coating agent.

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