Curable composition, anti-fog coating agent, and cured film

A curable composition with specific (meth)acrylate compounds and surfactants addresses the inadequacy of conventional anti-fogging compositions by forming a low-surface-tension water film, enhancing anti-fogging performance in high humidity conditions.

JP7706253B2Active Publication Date: 2025-07-11TOKYO OHKA KOGYO CO LTD
View PDF 8 Cites 0 Cited by

Patent Information

Application Number
JP2021059661
Authority / Receiving Office
JP · JP
Patent Type
Patents
Current Assignee / Owner
Filing Date
2021-03-31
Publication Date
2025-07-11
Estimated Expiration
2041-03-31

AI Technical Summary

Technical Problem

Conventional anti-fogging compositions do not provide satisfactory anti-fogging properties, especially in high humidity environments.

Method used

A curable composition containing a (meth)acrylate compound with an HLB value of 15.2 or more and a surfactant content of 0.1 to 20 parts by mass, which forms a water film with low surface tension to enhance anti-fogging properties.

Benefits of technology

The composition achieves a cured film with excellent anti-fogging properties by absorbing moisture and forming a low-surface-tension water film, effectively preventing fogging.

✦ Generated by Eureka AI based on patent content.

Smart Images

  • Figure 0007706253000001
    Figure 0007706253000001
  • Figure 0007706253000002
    Figure 0007706253000002
  • Figure 0007706253000003
    Figure 0007706253000003
Patent Text Reader

Abstract

To provide a curable composition that provides a cured film excellent in antifogging properties, an antifogging coating agent containing the composition, and a cured film formed from a cured product of the composition.SOLUTION: A curable composition according to an embodiment of the invention contains a (meth)acrylate compound (A), and a surfactant (B). The component (A) contains a (meth)acrylate compound (A1) having an HLB value of 15.2 or more. The content of the component (B) is 0.1-20 pts.mass with respect to 100 pts.mass of the component (A).SELECTED DRAWING: None
Need to check novelty before this filing date? Find Prior Art

Description

Technical Field

[0001] The present invention relates to a curable composition, an anti-fog coating agent comprising the composition, and a cured film comprising a cured product of the composition.

Background Art

[0002] In places with a lot of moisture, dew condensation may occur on the surface of articles. In particular, in the case of transparent articles such as window glass and lenses, and reflective articles such as mirrors, if the progress of light is hindered by fogging caused by dew condensation, a normal field of view cannot be provided to the user. Therefore, such articles preferably have a function for preventing fogging.

[0003] In order to solve the above problems, in recent years, anti-fogging compositions that are cured by active energy rays such as ultraviolet rays and electron beams have been proposed. Specifically, anti-fogging agents composed of a hydrophilic group-containing photocurable ethylenically unsaturated compound, a hydrophilic group-free photocurable ethylenically unsaturated compound, and a photoinitiator have been proposed (Patent Document 1).

Prior Art Documents

Patent Documents

[0004]

Patent Document 1

Summary of the Invention

Problems to be Solved by the Invention

[0005] However, conventional anti-fogging compositions have not provided satisfactory anti-fogging properties, such as not exhibiting anti-fogging properties in an environment under high humidity.

[0006] The present invention has been made in view of the above problems, and an object thereof is to provide a curable composition that gives a cured film excellent in anti-fogging properties, an anti-fog coating agent comprising the composition, and a cured film comprising a cured product of the composition.

Means for Solving the Problems

[0007] The inventors of the present invention have conducted intensive studies to solve the above problems. As a result, they have found that the above problems can be solved by a curable composition containing a (meth)acrylate compound (A1) having an HLB value within a predetermined range and a predetermined amount of a surfactant (B), and have completed the present invention. Specifically, the present invention provides the following.

[0008] A first aspect of the present invention is a curable composition containing a (meth)acrylate compound (A) and a surfactant (B), wherein the component (A) contains a (meth)acrylate compound (A1) having an HLB value of 15.2 or more, and the content of the component (B) is 0.1 to 20 parts by mass with respect to 100 parts by mass of the component (A).

[0009] A second aspect of the present invention is an anti-fogging coating agent comprising the curable composition.

[0010] A third aspect of the present invention is a cured film comprising a cured product of the curable composition.

Advantages of the Invention

[0011] According to the present invention, it is possible to provide a curable composition that gives a cured film excellent in anti-fogging properties, an anti-fogging coating agent comprising the composition, and a cured film comprising a cured product of the composition.

Modes for Carrying Out the Invention

[0012] ≪Curable Composition≫ The curable composition according to the present invention contains a (meth)acrylate compound (A) and a surfactant (B), wherein the component (A) contains a (meth)acrylate compound (A1) having an HLB value of 15.2 or more, and the content of the component (B) is 0.1 to 20 parts by mass with respect to 100 parts by mass of the component (A).

[0013] In the cured film composed of the cured product of the curable composition according to the present invention, since the HLB value of the component (A1) is 15.2 or more, the component derived from the component (A1) exhibits antifogging properties by adsorbing moisture on the surface of the cured film and simultaneously absorbing moisture. Further, after the moisture absorption limit of the component derived from the component (A1), usually, water droplets adhere and the surface of the cured film becomes cloudy. However, in the cured film of the present invention, the component (B) dissolved in the absorbed moisture elutes to the surface of the cured film, and antifogging properties are exhibited by forming a water film with a low surface tension. In this way, the curable composition according to the present invention can provide a cured film excellent in antifogging properties.

[0014] In this specification, “(meth)acrylate” means both acrylate and methacrylate, “(meth)acrylic” means both acrylic and methacrylic, and “(meth)acryloyl” means both acryloyl and methacryloyl. Further, in this specification, “polyfunctional (meth)acrylate compound” means a compound containing two or more (meth)acryloyl groups in one molecule.

[0015] Hereinafter, the essential or optional components contained in the curable composition will be described.

[0016] <Component (A)> The curable composition according to the present invention contains a (meth)acrylate compound (A), and the component (A) contains a (meth)acrylate compound (A1) having an HLB value of 15.2 or more. Thereby, in the cured film composed of the cured product of the above composition, the moisture adsorbed on the surface of the cured film is absorbed, and excellent antifogging properties are obtained.

[0017] The HLB value of the (meth)acrylate compound (A1) is preferably 15.5 or more, more preferably 16.0 or more. The upper limit of the HLB value is not particularly limited.

[0018] In this specification, the HLB value of the (meth)acrylate compound (A1) is a value obtained by the following formula based on the Griffin method. HLB value = 20 × total formula weight of hydrophilic functional groups / molecular weight In this specification, the hydrophilic functional group is a sulfone group (-SO3-), a phosphono group (-PO3-), a carboxyl group (-COOH), an amide group (-CONH-), an imide group (-CON-), an aldehyde group (-CHO), a hydroxyl group (-OH), an amino group (-NH2), an acetyl group (-COCH3), an ethyleneamine group (-CH2CH2N-), an ethyleneoxy group (-CH2CH2O-), an alkali metal ion, an alkaline earth metal ion, an ammonium ion, a halide ion, or an acetate ion.

[0019] Examples of the (meth)acrylate compound (A1) include a polyfunctional (meth)acrylate compound having an alkyleneoxy group with 2 to 4 carbon atoms, specifically, a polyfunctional (meth)acrylate compound having an ethyleneoxy group.

[0020] As the (meth)acrylate compound (A1), a polyfunctional (meth)acrylate compound represented by the following formula (a1) and / or a bifunctional (meth)acrylate compound represented by the following formula (a2) is preferable, and a polyfunctional (meth)acrylate compound represented by the following formula (a1) is more preferable. [Chemical formula] (In formula (a1), n is a number of 4 or more. A 1 each independently represents an alkylene group having 2 to 4 carbon atoms. k, l, and m are numbers of 0 or more, and the total is 50 or more. R 1 each independently represents a hydrogen atom or a (meth)acryloyl group, and at least three are (meth)acryloyl groups.) [Chemical formula] (In formula (a2), A 2 represents an alkylene group having 2 to 4 carbon atoms. p is a number of 10 or more. R 2 each independently represents a (meth)acryloyl group.)

[0021] In formula (a1), n is a number of 4 or more, preferably a number from 4 to 10, more preferably a number from 4 to 6. A 1 is each independently an alkylene group having 2 to 4 carbon atoms, and may be linear or branched. A 1 is preferably an ethylene group. k, l, and m are each independently a number of 0 or more, preferably a number from 1 to 40, more preferably a number from 1 to 30. The sum of k, l, and m is 50 or more, preferably 50 to 100, more preferably 55 to 80. R 1 each independently represents a hydrogen atom or a (meth)acryloyl group, at least three are (meth)acryloyl groups, preferably at least four are (meth)acryloyl groups, and more preferably at least six are (meth)acryloyl groups.

[0022] In formula (a2), A 2 is an alkylene group having 2 to 4 carbon atoms, and may be linear or branched. A 2 is preferably an ethylene group. p is a number of 10 or more, preferably a number from 10 to 30, more preferably a number from 12 to 20. R 2 are each independently a (meth)acryloyl group.

[0023] The content of the (meth)acrylate compound (A1) in 100% by mass of the component (A) is preferably 35 to 99% by mass, more preferably 40 to 90% by mass, and even more preferably 50 to 80% by mass. When within the above numerical range, a good anti-fogging property tends to be obtained.

[0024] The component (A) preferably contains a polyfunctional (meth)acrylate compound (A2) other than the component (A1). This makes it easier to improve the curability of the cured film.

[0025] Examples of the polyfunctional (meth)acrylate compound (A2) include ethylene glycol di(meth)acrylate, diethylene glycol di(meth)acrylate, tetraethylene glycol di(meth)acrylate, propylene glycol di(meth)acrylate, polypropylene glycol di(meth)acrylate, butylene glycol di(meth)acrylate, neopentyl glycol di(meth)acrylate, 1,6 - hexanediol di(meth)acrylate, trimethylolpropane tri(meth)acrylate, glycerin di(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa(meth)acrylate, pentaerythritol di(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa(meth)acrylate, ethylene glycol diglycidyl ether di(meth)acrylate, diethylene glycol diglycidyl ether di(meth)acrylate, phthalic acid diglycidyl ester di(meth)acrylate, glycerin tri(meth)acrylate, glycerin polyglycidyl ether poly(meth)acrylate, and the like.

[0026] The content of the polyfunctional (meth)acrylate compound (A2) in 100% by mass of the component (A) is preferably 1 to 65% by mass, more preferably 10 to 60% by mass, and still more preferably 20 to 50% by mass. When within the above numerical range, it is easy to achieve both an improvement in the hardness of the cured film and antifogging properties.

[0027] The content of the (meth)acrylate compound (A) is preferably 40% by mass or more, more preferably 60% by mass or more, and still more preferably 80% by mass or more, based on the mass of the curable composition (total solid content) excluding the mass of the solvent (E) described later. The above content is preferably 99% by mass or less. When within the above numerical range, there is a tendency to obtain good antifogging properties.

[0028] <(B) component> The curable composition according to the present invention contains a surfactant (B), and the content of the (B) component is 0.1 to 20 parts by mass with respect to 100 parts by mass of the (A) component. As a result, in the cured film composed of the cured product of the above composition, after the moisture absorption limit of the component derived from the (A1) component, the (B) component dissolved in the absorbed moisture elutes to the surface of the cured film, and by forming a water film with low surface tension, excellent antifogging properties can be obtained.

[0029] As the surfactant (B), a water-soluble surfactant can be preferably used. As the water-soluble surfactant, there is no particular limitation as long as it is a surfactant that dissolves in water, but it is preferably soluble at 0.01% by mass or more. As the surfactant (B), any of a nonionic surfactant, a cationic surfactant, an anionic surfactant, and an amphoteric surfactant can be used. The surfactant may be silicone-based. These may be used alone or in combination of two or more.

[0030] Examples of the nonionic surfactant include polyoxyethylene octyl ether, polyoxyethylene decyl ether, polyoxyethylene lauryl ether, polyoxyethylene laurylamine, polyoxyethylene oleylamine, polyoxyethylene polystyryl phenyl ether, polyoxyalkylene polystyryl phenyl ether, etc., polyoxyalkylene primary alkyl ether or polyoxyalkylene secondary alkyl ether, etc. Examples of the cationic surfactant include oleylamine acetate, lauryl pyridinium chloride, cetyl pyridinium chloride, lauryl trimethyl ammonium chloride, stearyl trimethyl ammonium chloride, behenyl trimethyl ammonium chloride, didecyldimethyl ammonium chloride, didecyldimethyl ammonium bromide, etc. Examples of anionic surfactants include coconut fatty acid salts, castor oil sulfate salts, lauryl sulfate salts, polyoxyalkylene allyl phenyl ether sulfate salts, alkylbenzene sulfonic acids, alkylbenzene sulfonate salts, alkyldiphenyl ether disulfonate salts, alkylnaphthalene sulfonate salts, dialkyl sulfosuccinate salts, isopropyl phosphate, polyoxyethylene alkyl ether phosphate salts, polyoxyethylene allyl phenyl ether phosphate salts, dialkyl sulfosuccinate salts, and the like. Examples of amphoteric surfactants include coconut alkyl dimethylamine oxide, fatty acid amidopropyl dimethylamine oxide, alkyl polyaminoethyl glycine hydrochloride, amide betaine type surfactants, alanine type surfactants, lauryliminodipropionic acid, and the like.

[0031] The content of the surfactant (B) is 0.1 to 20 parts by mass, preferably 0.5 to 15 parts by mass, and more preferably 1 to 10 parts by mass with respect to 100 parts by mass of the component (A). When within the above numerical range, there is a tendency to obtain good anti-fogging properties.

[0032] <(Component D)> The curable composition according to the present invention preferably contains an initiator (D). The initiator (D) is not particularly limited, and conventionally known photopolymerization initiators, thermal polymerization initiators, etc. can be used. However, a photopolymerization initiator is preferred in terms of easily curing the polymerizable composition well in a short time and the like.

[0033] Specific examples of the photoinitiator include 1-hydroxycyclohexyl phenyl ketone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, 1-[4-(2-hydroxyethoxy)phenyl]-2-hydroxy-2-methyl-1-propan-1-one, 1-(4-isopropylphenyl)-2-hydroxy-2-methylpropan-1-one, 1-(4-dodecylphenyl)-2-hydroxy-2-methylpropan-1-one, 2,2-dimethoxy-1,2-diphenylethan-1-one, bis(4-dimethylaminophenyl) ketone, 2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one, 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butan-1-one, 1,2-octanedione, 1-[4-(phenylthio)phenyl]-, 2-(O-benzoyloxime) (Irgacure OXE01), ethanone-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-1-(O-acetoxyoxime) (Irgacure OXE02), 2,4,6-trimethylbenzoyldiphenylphosphine oxide (Omnirad TPO H), bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide (Omnirad 819), 4-benzoyl-4'-methyldimethyl sulfide, 4-dimethylaminobenzoic acid, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, butyl 4-dimethylaminobenzoate, 4-dimethylamino-2-ethylhexyl benzoate, 4-dimethylamino-2-isoamyl benzoic acid, benzyl-β-methoxyethyl acetal, benzyl dimethyl ketal, 1-phenyl-1,2-propanedione-2-(O-ethoxycarbonyl)oxime, methyl O-benzoylbenzoate, 2,4-diethylthioxanthone, 2-chlorothioxanthone, 2,4-dimethylthioxanthone, 1-chloro-4-propoxythioxanthone, thioxanthene, 2-chlorothioxanthene, 2,4-diethylthioxanthene, 2-methylthioxanthene, 2-isopropylthioxanthene, 2-ethylanthraquinone, octamethylanthraquinone, 1,2-benzanthraquinone, 2,3-Diphenylanthraquinone, azobisisobutyronitrile, benzoyl peroxide, cumene hydroperoxide, 2-mercaptobenzimidazole, 2-mercaptobenzoxazole, 2-mercaptobenzothiazole, 2-(O-chlorophenyl)-4,5-di(m-methoxyphenyl)-imidazolyl dimer, benzophenone, 2-chlorobenzophenone, p,p'-bisdimethylaminobenzophenone, 4,4'-bisdiethylaminobenzophenone, 4,4'-dichlorobenzophenone, 3,3-dimethyl-4-methoxybenzophenone, benzyl, benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin-n-butyl ether, benzoin isobutyl ether, benzoin butyl ether, acetophenone, 2,2-diethoxyacetophenone, p-dimethylacetophenone, p-dimethylaminopropiophenone, dichloroacetophenone, trichloroacetophenone, p-tert-butylacetophenone, p-dimethylaminoacetophenone, p-tert-butyltrichloroacetophenone, p-tert-butyldichloroacetophenone, α,α-dichloro-4-phenoxyacetophenone, thioxanthone, 2-methylthioxanthone, 2-isopropylthioxanthone, dibenzosuberone, pentyl-4-dimethylaminobenzoate, 9-phenylacridine, 1,7-bis-(9-acridinyl)heptane, 1,5-bis-(9-acridinyl)pentane, 1,3-bis-(9-acridinyl)propane, p-methoxy triazine, 2,4,6-tris(trichloromethyl)-s-triazine, 2-methyl-4,6-bis(trichloromethyl)-s-triazine, 2-[2-(5-methylfuran-2-yl)ethenyl]-4,6-bis(trichloromethyl)-s-triazine, 2-[2-(furan-2-yl)ethenyl]-4,6-bis(trichloromethyl)-s-triazine, 2-[2-(4-diethylamino-2-methylphenyl)ethenyl]-4,6-bis(trichloromethyl)-s-triazine, 2-[2-(3,4-dimethoxyphenyl)ethenyl]-4,6-bis(trichloromethyl)-s-triazine, 2-(4-methoxyphenyl)-4,6-bis(trichloromethyl)-s-triazine, 2-(4-ethoxystyryl)-4,6-bis(trichloromethyl)-s-triazine, 2-(4-n-butoxyphenyl)-4,6-bis(trichloromethyl)-s-triazine, 2,4-bis-trichloromethyl-6-(3-bromo-4-methoxy)phenyl-s-triazine, 2,4-bis-trichloromethyl-6-(2-bromo-4-methoxy)phenyl-s-triazine, 2,4-bis-trichloromethyl-6-(3-bromo-4-methoxystyryl)phenyl-s-triazine, 2,4-bis-trichloromethyl-6-(2-bromo-4-methoxystyryl)phenyl-s-triazine and the like can be mentioned. These photoinitiators can be used alone or in combination of two or more kinds.,

[0034] Specific examples of the thermal polymerization initiator include organic peroxides such as ketone peroxides (such as methyl ethyl ketone peroxide and cyclohexanone peroxide), peroxyketals (such as 2,2-bis(tert-butylperoxy)butane and 1,1-bis(tert-butylperoxy)cyclohexane), hydroperoxides (such as tert-butyl hydroperoxide and cumene hydroperoxide), dialkyl peroxides (such as di-tert-butyl peroxide (Perbutyl (registered trademark) D (manufactured by NOF Corporation), and di-tert-hexyl peroxide (Perhexyl (registered trademark) D (manufactured by NOF Corporation))), diacyl peroxides (such as isobutyryl peroxide, lauroyl peroxide and benzoyl peroxide), peroxydicarbonates (such as diisopropyl peroxydicarbonate), peroxy esters (such as tert-butyl peroxyisobutyrate and 2,5-dimethyl-2,5-di(benzoylperoxy)hexane), etc., and azo compounds such as 1,1'-azobis(cyclohexane-1-carbonitrile), 2,2'-azobisisobutyronitrile, 2,2'-azobis(2,4-dimethyl-4-methoxyvaleronitrile), 2,2'-azobis(2-methylpropionamidine) dihydrochloride, 2,2'-azobis[2-methyl-N-(2-propenyl)propionamidine] dihydrochloride, 2,2'-azobis(2-methylpropionamide), 2,2'-azobis[2-methyl-N-(2-hydroxyethyl)propionamide], 2,2'-azobis(2-methylpropane), 2,2'-azobis(2,4,4-trimethylpentane) and dimethyl 2,2'-azobis(2-methylpropionate), etc. These thermal polymerization initiators can be used alone or in combination of two or more kinds.

[0035] The content of the initiator (D) is preferably 0.1 to 20 parts by mass, more preferably 1 to 15 parts by mass, and still more preferably 3 to 12 parts by mass with respect to 100 parts by mass of the component (A). When within the above numerical range, good anti-fogging properties tend to be obtained.

[0036] <Solvent (E)> The curable composition according to the present invention preferably contains a solvent (E) for the purpose of adjusting coatability and viscosity. The type of the solvent (E) is not particularly limited, but is typically an organic solvent. The type of the organic solvent is not particularly limited as long as the components contained in the curable composition can be uniformly dissolved or dispersed.

[0037] Examples of the organic solvent include (poly)alkylene glycol monoalkyl ethers such as ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol - n - propyl ether, ethylene glycol mono - n - butyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol mono - n - propyl ether, diethylene glycol mono - n - butyl ether, triethylene glycol monomethyl ether, triethylene glycol monoethyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol mono - n - propyl ether, propylene glycol mono - n - butyl ether, dipropylene glycol monomethyl ether, dipropylene glycol monoethyl ether, dipropylene glycol mono - n - propyl ether, dipropylene glycol mono - n - butyl ether, tripropylene glycol monomethyl ether, tripropylene glycol monoethyl ether; (poly)alkylene glycol monoalkyl ether acetates such as ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, diethylene glycol monomethyl ether acetate, diethylene glycol monoethyl ether acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate; other ethers such as diethylene glycol dimethyl ether, diethylene glycol methyl ethyl ether, diethylene glycol diethyl ether, tetrahydrofuran; ketones such as methyl ethyl ketone, cyclohexanone, 2 - heptanone, 3 - heptanone; alkyl lactates such as methyl 2 - hydroxypropionate, ethyl 2 - hydroxypropionate;Ethyl 2-hydroxy-2-methylpropionate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, ethyl ethoxyacetate, ethyl hydroxyacetate, methyl 2-hydroxy-3-methylbutyrate, 3-methoxybutyl acetate, 3-methyl-3-methoxybutyl acetate, 3-methyl-3-methoxybutyl propionate, ethyl acetate, n-propyl acetate, isopropyl acetate, n-butyl acetate, isobutyl acetate, n-pentyl formate, isopentyl acetate, n-butyl propionate, ethyl butyrate, n-propyl butyrate, isopropyl butyrate, n-butyl butyrate, methyl pyruvate, ethyl pyruvate, n-propyl pyruvate, methyl acetoacetate, ethyl acetoacetate, ethyl 2-oxobutyrate and other esters; aromatic hydrocarbons such as toluene and xylene; amides such as N-methylpyrrolidone, N,N-dimethylformamide and N,N-dimethylacetamide; alcohols such as ethanol, isopropyl alcohol and butanol, etc. These may be used alone or in combination of two or more.;

[0038] The content of the solvent (E) is not particularly limited as long as it does not inhibit the object of the present invention. From the viewpoint of film-forming property, when the mass of the curable composition excluding the mass of the solvent (E) is defined as the solid content, the solvent is used such that the solid content concentration is preferably 0.1 to 100% by mass, more preferably 1 to 50% by mass.;

[0039] <Other components> The curable composition according to the present invention may contain various additives conventionally blended in curable compositions in addition to the components described above, as long as the object of the present invention is not inhibited. Preferred additives to be blended in the curable composition include dispersants, adhesion promoters such as silane coupling agents, antioxidants, anti-aggregation agents, defoaming agents and the like.;

[0040] <Method for producing curable composition> The components described above are each mixed in a predetermined amount, and then the mixture is uniformly stirred to obtain a curable composition.;

[0041] <Use of the curable composition> Since the curable composition according to the present invention can form a cured product having excellent antifogging properties, it can be suitably used as an antifogging coating agent or the like. Examples of the application of the antifogging coating agent are not particularly limited as long as they are articles that require antifogging properties. For example, glasses, protective glasses, goggles, inner walls of bathrooms, members around the kitchen, and glass and plastic used for headlamp covers and rear lamp covers of automobiles, motorcycles, etc.

[0042] ≪Cured film≫ The cured film composed of the cured product of the curable composition described above has excellent antifogging properties. The thickness of the cured film is not particularly limited, but for example, it is 0.1 to 100 μm, and preferably 1 to 50 μm. Examples of the application of the cured film are the same as those of the above-mentioned antifogging coating agent.

Examples

[0043] Hereinafter, the present invention will be described in more detail with reference to examples, but the present invention is not limited to these examples.

[0044] Hereinafter, various chemicals used in the examples and comparative examples will be collectively described. <Component (A1)> A-11: An acrylate compound represented by the following formula (total of m: 60, n: 4, HLB value: 16.11)

Chemical formula

[0045] <Component (B)> B-1: Sodium di-2-ethylhexyl sulfosuccinate (manufactured by Tokyo Chemical Industry Co., Ltd., cationic surfactant, compound represented by the following formula) [Chemical formula] B-2: Polyethylene glycol monooleyl ether (manufactured by Tokyo Chemical Industry Co., Ltd., nonionic surfactant, compound represented by the following formula (b) (n = about 2)) B-3: Polyethylene glycol monooleyl ether (manufactured by Tokyo Chemical Industry Co., Ltd., nonionic surfactant, compound represented by the following formula (b) (n = about 7)) B-4: Polyethylene glycol monooleyl ether (manufactured by Tokyo Chemical Industry Co., Ltd., nonionic surfactant, compound represented by the following formula (b) (n = about 10)) C 18 H 35 (CH2CH2O) n OH (b) B-5: Surfron S-242 (manufactured by AGC Seimi Chemical Co., Ltd., nonionic surfactant, 100% by mass of active ingredient) B-6: Didecyldimethylammonium bromide (manufactured by Tokyo Chemical Industry Co., Ltd., cationic surfactant)

[0046] <Component (A2)>[[]] A-21: KAYARAD DPHA (manufactured by Nippon Kayaku Co., Ltd., mixture of dipentaerythritol hexaacrylate (a = 6, b = 0) / dipentaerythritol pentaacrylate (a = 5, b = 1) represented by the following formula, HLB value: 0.65 or less) [Chemical formula] A-22: M-309 (manufactured by Toagosei Co., Ltd., compound represented by the following formula, trimethylolpropane triacrylate, HLB value: 0) (CH2=CHCOOCH2)3-CCH2CH3 A-23: Acrylate compound represented by the following formula (total of m: 6, n: 4, HLB value: 5.85) [Chemical formula] A-24: Acrylate compound represented by the following formula (HLB value: 15.17) CH2=CH-C(=O)-O-(CH2CH2O)9-C(=O)-CH=CH2

[0047] <(Component (D))> D-1: IRGACURE 651 (manufactured by IGM Resins, compound represented by the following formula (Ph represents a phenyl group)) Ph-C(=O)-C(OCH3)2-Ph

[0048] <(Component (E))> E-1: Propylene glycol monomethyl ether (PGME) E-2: Isopropyl alcohol (IPA)

[0049] (Examples and Comparative Examples) The chemicals of the types and amounts shown in Tables 1 and 2 were uniformly mixed to obtain the curable compositions of the examples and comparative examples. Each of the obtained curable compositions was spin-coated on a polycarbonate (PC) plate and heated at 80 °C for 5 minutes. Then, using an ultra-high pressure mercury lamp, exposure was carried out at an irradiation dose of 3000 mJ / cm 2 to produce a cured film with a film thickness of 5 μm. For each of the obtained cured films, the antifogging property was evaluated according to the following method. The results are shown in Tables 1 and 2.

[0050] (Antifogging Property) After wiping the surface of the produced substrate with a cloth wet with water, 50 mL of water at 50 °C was added to a 100 mL beaker, and the produced cured film was exposed 5 cm away from the water surface for 3 minutes. The fogging state of the cured film at that time was visually evaluated according to the following criteria. 〇: Does not fog for 3 minutes or more ×: Fogs in less than 3 minutes

[0051]

Table 1

[0052]

Table 2

[0053] As shown in Tables 1 and 2, it was found that the anti-fogging property of the examples was good, while that of the comparative examples was poor. Therefore, it was confirmed that the curable composition according to the present invention gives a cured film excellent in anti-fogging property.

Claims

1. A curable composition containing a (meth)acrylate compound (A) and a surfactant (B), wherein the component (A) contains a (meth)acrylate compound (A1) having an HLB value of 15.5 or more, the component (A1) includes a polyfunctional (meth)acrylate compound represented by the following formula (a1), and the content of the component (B) is 0.1 to 20 parts by mass with respect to 100 parts by mass of the component (A). 【Chemical 1】 (In formula (a1), n is a number of 4 or more. A 1 each independently represents an alkylene group having 2 carbon atoms. k, l, and m are numbers of 0 or more, and the total is 50 or more. R 1 each independently represents a hydrogen atom or a (meth)acryloyl group, and at least three are (meth)acryloyl groups.)

2. Furthermore, the component (A) contains a polyfunctional (meth)acrylate compound (A2) other than the component (A1), and the content of the component (A2) in 100% by mass of the component (A) is 1 to 65% by mass. The curable composition according to Claim 1.

3. Furthermore, it contains an initiator (D), and the content of the component (D) is 0.1 to 20 parts by mass with respect to 100 parts by mass of the component (A). The curable composition according to Claim 1 or 2.

4. An anti-fogging coating agent comprising the curable composition according to any one of Claims 1 to 3.

5. A cured film comprising a cured product of the curable composition according to any one of Claims 1 to 3.

Citation Information

Patent Citations

  • Antiifogging agent

    JP1980069678A

  • Ultraviolet-curing type antifogging composition

    JP2005239832A

  • Conductive composition for electrophotographic equipment, conductive crosslinked material for electrophotographic equipment and conductive member for electrophotographic equipment

    JP2009075434A

  • Anti-fogging glass

    JP2009102208A

  • Photosensitive polyorganosiloxane composition, polyorganosiloxane-cured relief pattern and method for forming the same, and semiconductor device and method for producing the same

    JP2010006982A