Resin composition, laminate, and molded article

Abstract

To provide an active energy ray-polymerizable composition that can give a cured coat having excellent adhesion, excoriation resistance, and alcohol resistance and also having superior resistance to bacteria deposition, and an article including the cured coat.SOLUTION: An active energy ray-curable composition comprises a methacrylate (A) containing alkylene oxide, a methacrylate (B) containing no alkylene oxide but having three or more functional groups, with a radical polymerizable compound having a double bond equivalent of 5.0 mmol / g or more, and the alkylene oxide equivalent being 4.0 mmol / g or more.SELECTED DRAWING: None

Description

[Technical field]

[0001] The present invention relates to a resin composition, a laminate made of the resin composition, and a substrate having the laminate on a surface thereof. This relates to molded products such as cosmetic containers and electrical appliances. [Background technology]

[0002] The active energy ray-curable composition can be cured in a short time by irradiation with active energy rays such as ultraviolet rays. The composition has the property of being polymerized and hardened. For example, the composition is used in home electronics such as mobile phones and chemicals. It is used as a material for forming a hardened coating to modify the surface of the base material of cosmetic containers. The cured coating obtained from this composition has excellent adhesion to the substrate and scratch resistance. Furthermore, when the base material is a cosmetic container, etc., it is necessary to prevent corrosion due to the contents of the cosmetic, etc. In order to do this, alcohol resistance is required. In general, active energy ray curable compositions have improved scratch resistance and solvent resistance by increasing the crosslink density. However, curing shrinkage increases, cracks occur in the cured coating, and There is a problem in that the adhesion decreases.

[0003] On the other hand, in recent years, cleanliness is being demanded for various industrial products. The demand for cleanliness is particularly strong for industrial products that are used in close proximity to the environment. It is easy for nutrients for microorganisms such as sweat, dirt, and food debris to adhere to the surface, which can lead to explosive bacterial growth. For example, medical facilities, food factories, clothing factories, schools, stations, banks, convenience stores, etc. A. In various public facilities, products with excellent cleanliness are required, from industrial products to daily necessities. It is being done.

[0004] By introducing polyethylene glycol (PEG) into the surface of these articles, proteins It has been found to inhibit adsorption and therefore bacterial adhesion. It is known that the surface with PEG brush structure significantly suppresses the adsorption of biomolecules. It has been reported as a surface treatment technology that imparts the ability to suppress nonspecific adsorption to the substrate surface. G is a hydrophilic molecule with high molecular chain mobility, i.e., a steric exclusion effect that suppresses protein adsorption. It is believed that the combination of the nonionic properties of PEG and PEG-10001 ... It is being done. However, in order to realize such properties, it is necessary to directly introduce PEG onto the substrate surface. Therefore, there are limitations on the materials that can be used.

[0005] Patent Document 1 describes an active energy ray-curable composition containing an alkylene oxide. It has been reported that polyfunctional acrylates modified with alkylene oxide and ε-caprolactone The use of ethylene glycol gives flexibility to the laminate, reducing shrinkage that occurs during photocuring and durability testing. It is possible to achieve this by lowering the crosslink density to give it flexibility, which improves scratch resistance. There is room for improvement in terms of alcohol resistance. [Prior art documents] [Patent documents]

[0006] [Patent Document 1] JP 2011-198434 A Summary of the Invention [Problem to be solved by the invention]

[0007] The object of the present invention is to solve the above problems, and to provide a coating composition having excellent adhesion, scratch resistance, and alcohol resistance, Further, an active energy ray-polymerizable composition which can provide a cured coating film with excellent low bacterial adhesion, and The present invention provides an article having a cured coating of the above-mentioned. [Means for solving the problem]

[0008] The above problems are solved by the present inventions [1] to [7] below. [1] A (meth)acrylate containing an alkylene oxide (A) and an alkylene oxide A radical polymerizable compound containing a trifunctional or higher (meth)acrylate (B) that does not contain amide. The double bond equivalent is 5.0 mmol / g or more, and the alkylene oxide equivalent is 4.0 mmol / g or more. mol / g or more. [2] The active energy storage device according to [1], wherein the alkylene oxide is ethylene oxide. Lugie radiation curable composition. [3] The active energy ray-curable composition according to [1] or [2], further comprising a surface conditioner (C). Composition. [4] A cured product of the active energy ray-curable composition according to any one of [1] to [3]. [5] The active energy ray-curable composition according to [4], wherein the cured product is a material with low bacterial adhesion. thing. [6] A laminate having a substrate and the cured product described in [4]. [7] A (meth)acrylate containing an alkylene oxide (A) and an alkylene oxide A radical polymerizable compound containing a trifunctional or higher (meth)acrylate (B) that does not contain amide. The double bond equivalent is 5.0 mmol / g or more, and the alkylene oxide equivalent is 4.0 mmol / g or more. mol / g or more, and curing the active energy ray-curable composition. Effect of the Invention

[0009] According to the present invention, the adhesive layer has excellent adhesion, scratch resistance, and alcohol resistance, and further has low bacterial adhesion. Active energy ray polymerizable composition capable of obtaining a favorable cured film, and article having the cured film - Patents.com can be provided. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0010] The embodiment of the present invention will be described in detail below. The following description is based on the embodiment of the present invention. The following description is merely an example, and the present invention is not limited to the following description unless it exceeds the gist of the present invention. stomach.

[0011] In this specification, when the expression "~" is used, the numerical values ​​or physical properties before and after it are In the present invention, the term "(meth)acrylic" is used as an expression including the above. When the expression is used, it shall mean either or both of "acrylic" and "methacrylic". The same applies to "(meth)acrylate", "(meth)acryloyl", etc.

[0012] [Active energy ray-curable composition] The active energy ray-curable composition of the present invention (hereinafter referred to as the present composition) comprises an alkyleneoxy group. (A) (hereinafter referred to as component (A)), alkyleneoxy (B) a tri- or higher functional (meth)acrylate (not including side groups) (hereinafter referred to as component (B)) It may also contain a surface conditioner (C) (hereinafter referred to as component (C)). In addition, the composition may further contain other ingredients as long as the effects of the present invention can be obtained. Good too.

[0013] [Component (A)] The composition contains (A) an alkylene oxide-containing (meth)acrylate. Component (A) is a component that contributes to improving the adhesiveness and reducing bacterial adhesion of the present composition. The (meth)acrylate monomer (A-1) may be a (meth)acrylate o From the viewpoint of adhesion and curing property, (meth)acrylate It is more preferable that the composition contains at least one type of oligomer (A-2).

[0014] The (meth)acrylate monomer (A-1) is a polyhydric alcohol having an alkyleneoxy group. (Meth)acrylic acid esters of compounds with alkylene oxide skeletons Examples of the above compounds include (meth)acrylic esters of alcohols. Trimethylolpropane, glycerin (including polyglycerin), pentaerythritol , ditrimethylolpropane, dipentaerythritol, etc., The alkylene oxide may be, for example, an alkylene oxide having 2 to 18 carbon atoms. More preferred are alkylene oxides having 2 to 8 carbon atoms, for example: , ethylene oxide, propylene oxide, butylene oxide, isobutylene oxide, 1-Butene oxide, 2-Butene oxide, Trimethylethylene oxide, Tetramethylethylene ethylene oxide, tetramethylethylene oxide, butadiene monoxide, octylene oxide Among them, ethylene oxide, propylene oxide, styrene oxide, etc. More preferred are alkylene oxides having 2 to 4 carbon atoms, such as butylene oxide and butylene oxide. Or, ethylene oxide, propylene oxide, and ethylene oxide. is most preferred. The alkylene oxide may be one type or two or more types. This is also fine.

[0015] The number of alkylene oxides present (repeating number) in the compound (A-1) is, The average repeat number of the total amount of alkylene oxide is -1) It is preferable that the amount is 2 to 16 mol per 1 mol. It is possible to more appropriately adjust the alcohol resistance and the low bacterial adhesion of the above-mentioned. The amount of the (meth)acrylate monomer ( Specific examples of A-1) include ethyl diethylene glycol (meth)acrylate. , ethylene glycol di(meth)acrylate, diethylene glycol di(meth)acrylate acrylate, triethylene glycol di(meth)acrylate, polyethylene glycol di( Meth)acrylate, polypropylene glycol di(meth)acrylate, glycerol 1,3-Di(meth)acrylate, Neopentyl glycol di(meth)acrylate, Polypropylene glycol di(meth)acrylate, neopentyl glycol hydroxypi Valent di(meth)acrylate, alkylene oxide adduct of trimethylolpropane Tri(meth)acrylate, trimethylolpropane and ε-caprolactone adduct Tri(meth)acrylate, alkylene oxide adduct of glycerin acrylate, tri(meth)acrylate of glycerin and ε-caprolactone adduct, pentaacrylate Tetra(meth)acrylate of alkylene oxide adduct of erythritol, pentaerythritol Tetra(meth)acrylate of ε-caprolactone adduct of erythritol, dipentaerythritol Hexa(meth)acrylate of alkylene oxide adduct of tallow, dipentaerythritol hexa(meth)acrylate of ε-caprolactone adduct of glycerol; (Meth)acrylates and the like. The (meth)acrylate monomer (A-1) is preferably trifunctional or more, and more preferably tetrafunctional. It is more preferable to use the above. This makes it possible to further exert the effect of the present invention, which is to effectively exert the effect of the present invention.

[0016] Examples of the (meth)acrylate oligomer (A-2) include epoxy (meth)acrylates. acrylate, urethane (meth)acrylate, polyester (meth)acrylate, copolymer (meth)acrylate, polybutadiene (meth)acrylate, silicone (meth)acrylate Among the (A-2) components, particularly preferred are acrylate and amino resin (meth)acrylate. In terms of ease of molecular design, cost, and handling, urethane (meth)acrylate is used. The urethane (meth)acrylate is preferably a polyisocyanate (a1) and water. From an acid group-containing (meth)acrylate (a2) and an oxyalkylene group-containing compound (a3), The resulting polyisocyanate derivative is:

[0017] (Polyisocyanate (a1)) The polyisocyanate (a1) is a compound having two or more isocyanate groups. Examples of the polyisocyanate (a1) include aromatic polyisocyanates and aliphatic polyisocyanates. and alicyclic polyisocyanates. Specifically, for example, tolylene diisocyanate (TDI), diphenylmethane diisocyanate Diphenylmethane diisocyanate (MDI), hydrogenated diphenylmethane diisocyanate (H-MDI), polyphenylene Phenylmethane polyisocyanate (crude MDI), modified diphenylmethane diisocyanate nate (modified MDI), hydrogenated xylylene diisocyanate (H-XDI), xylylene Diisocyanate (XDI), hexamethylene diisocyanate (HMDI), trimethyl Tetramethylhexamethylene diisocyanate (TMXDI), Tetramethylxylylene diisocyanate diisocyanate (m-TMXDI), isophorone diisocyanate (IPDI), norbornene diisocyanate Isocyanate (NBDI), phenylene diisocyanate, lysine diisocyanate, Polyisocyanates such as lysine triisocyanate and naphthalene diisocyanate (NDI) Trimeric compounds of these polyisocyanates, biuret type polyisocyanates, Water-dispersible polyisocyanate ("Aquanate 100" manufactured by Nippon Polyurethane Industry Co., Ltd.) ", "Aquanate 110", "Aquanate 200", "Aquanate 210", etc.) Some examples include: The polyisocyanates may be used alone or in combination of two or more kinds.

[0018] The polyisocyanate (a1) is any of these polyisocyanates (however, The number of aryl groups is limited to 3 or more. The reaction product of aryl groups and polyols may also be used. Examples of the glycol include ethylene glycol, diethylene glycol, and triethylene glycol. tetraethylene glycol, polyethylene glycol, propylene glycol, dipropylene glycol Propylene glycol, polypropylene glycol, butylene glycol, 1,4-butane Diol, polybutylene glycol, 1,6-hexanediol, neopentyl glycol Cyclohexanedimethanol, hydrogenated bisphenol A, polycaprolactone, Trimethylolethane, Trimethylolpropane, Polytrimethylolpropane, Pentaethylene Lithritol, polypentaerythritol, sorbitol, mannitol, glycerin, Polyhydric alcohols such as polyglycerin and polytetramethylene glycol; polyethylene oxide Side, polypropylene oxide, ethylene oxide / propylene oxide Polyether polyol having at least one structure of block copolymerization and random copolymerization Polyhydric alcohol or polyether polyol and maleic anhydride, maleic acid, fumaric acid It is a condensation product of polybasic acids such as itaconic acid, itaconic anhydride, itaconic acid, adipic acid, and isophthalic acid. polyester polyols; caprolactone-modified polytetramethylene polyols, etc. Prolactone modified polyol; Polyolefin polyol; Hydrogenated polybutadiene polyol and polybutadiene-based polyols such as polyols.

[0019] Other polyols include, for example, 2,2-bis(hydroxymethyl)butyric acid and tartaric acid. , 2,4-dihydroxybenzoic acid, 3,5-dihydroxybenzoic acid, 2,2-bis(hydroxybenzoic acid) 2,2-bis(hydroxymethyl)propionic acid, 2,2-bis(hydroxyethyl)propionic acid, -Bis(hydroxypropyl)propionic acid, dihydroxymethylacetic acid, bis(4-hydroxypropyl)propionic acid (4-hydroxyphenyl)acetic acid, 4,4-bis(4-hydroxyphenyl)pentanoic acid, homogenate Polyols containing carboxyl groups such as thiamine acid; sodium 1,4-butanediol sulfonate Also included are sulfonic acid group or sulfonate salt group-containing polyols such as polyols containing sulfonic acid groups. The reaction product of polyisocyanate and polyol may be used alone or in combination of two or more. may be used in combination.

[0020] In the reaction of polyisocyanate with polyol, in order to promote the reaction, A catalyst can be used. Examples of the catalyst include dibutyltin dilaurate, trimethyltin dilaurate, and the like. organometallic compounds such as tetra-n-butyltin hydroxide, zinc octoate, Metal salts such as tin phosphate, cobalt naphthenate, stannous chloride, stannic chloride, triethylamine, Benzyldiethylamine, 1,4-diazabicyclo[2,2,2]octane, 1,8-di Azabicyclo[5,4,0]undecene, N,N,N',N'-tetramethyl-1,3- Amine catalysts such as butanediamine, N-ethylmorpholine, etc.; bismuth nitrate, bismuth bromide , bismuth iodide, bismuth sulfide, etc., as well as dibutyl bismuth dilaurate, dioctyl bismuth Bismuth dilaurate and other organic bismuth compounds, bismuth 2-ethylhexanoate, naphthenic acid, Bismuth phosphate, bismuth isodecanoate, bismuth neodecanoate, bismuth laurate bismuth salts, bismuth maleate salts, bismuth stearate salts, bismuth oleate salts, linoleate salts Bismuth salt of phosphate, bismuth acetate, bismuth tribisneodecanoate, bisdisalicylate bismuth salts, bismuth salts of organic acids such as bismuth digallate, etc. . Among these, dibutyltin dilaurate, 1,8-diazabicyclo[5,4,0]urethane Undecene is preferred.

[0021] (Hydroxyl group-containing (meth)acrylate (a2)) The hydroxyl group-containing (meth)acrylate (a2) is a (meth)acrylate having one or more hydroxyl groups. The hydroxyl group-containing (meth)acrylate (a2) is an acrylate having at least one hydroxyl group. There are no particular limitations as long as the (meth)acrylate contains an acid group. Examples of the hydroxyl group-containing (meth)acrylate (a2) include 2-hydroxyethyl(meth)acrylate. (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 2-hydroxybuty (meth)acrylate, 4-hydroxybutyl (meth)acrylate, 2-hydroxy Ethyl acryloyl phosphate, 2-(meth)acryloyloxyethyl-2-hydroxy Dipropyl phthalate, 2-hydroxy-3-(meth)acryloyloxypropyl (meth) ) acrylate, caprolactone modified 2-hydroxyethyl (meth)acrylate, pen Taerythritol tri(meth)acrylate, Dipentaerythritol penta(meth)acrylate acrylate, caprolactone-modified dipentaerythritol penta(meth)acrylate, Caprolactone modified pentaerythritol tri(meth)acrylate, ethylene oxide Dipentaerythritol penta(meth)acrylate modified with ethylene oxide pentaerythritol tri(meth)acrylate. The hydroxyl group-containing (meth)acrylate (a2) may be used alone or in combination of two or more kinds. may be used.

[0022] (Oxyalkylene Group-Containing Compound (a3)) The oxyalkylene group-containing compound (a3) ​​has an oxyalkylene group and further has a polyvalent Has a hydroxyl group capable of forming a urethane bond with the isocyanate group of isocyanate (a1) . The oxyalkylene group-containing compound (a3) ​​includes a compound represented by the following formula (1): In addition, the oxyalkylene group-containing compound (a3) ​​may be used alone, Two or more types may be used in combination.

[0023] H-(OX)nOY formula (1)

[0024] In the formula (1), X's are alkylene groups, and may be the same or different. The alkylene group of X preferably has 2 to 5 carbon atoms. From the viewpoint of low bacterial adhesion, the carbon number of the alkylene group of X is particularly preferably 2. I wish. In the formula (1), n ​​is 1 or more, preferably 5 to 500, and more preferably 5 to 100. , 6 to 50 is more preferable. The oxyalkylene group in formula (1) has two or more different alkylene groups. In this case, the total number of moles (n) of oxyalkylene groups added is preferably 5 to 500, and more preferably 5 to 10 0 is more preferable, and 6 to 50 is further preferable.

[0025] In formula (1), Y is a hydrogen atom, an alkyl group, a (meth)acryloyl group, an allyl group, or an aryl group. Y is preferably a hydrogen atom from the viewpoint of low bacterial adhesion, and From the viewpoint of low adhesion, allyl groups and (meth)acryloyl groups are preferred. From the viewpoint of the appearance of the coating film, As Y, a (meth)acryloyl group is particularly preferred.

[0026] When Y is a hydrogen atom, the oxyalkylene group-containing compound (a3) ​​is represented by the following formula (2): can be.

[0027] H-(OX)n-OH...Formula (2)

[0028] In formula (2), X is an alkylene group and n is 1 or more. In formula (2), details and preferred embodiments of X and n are the same as those described for formula (1). is the same as:

[0029] The oxyalkylene group-containing compound (a3) ​​represented by formula (2) is preferably polyethylene glycol. Recall, polypropylene glycol, polybutylene glycol, polytetramethylene glycol glycols such as lycol; polyethylene oxide, polypropylene oxide, ethylene At least one block copolymer of propylene oxide / propylene oxide and random copolymerization Examples of the polyether polyol include polyether polyols having one type of structure.

[0030] When Y is an alkyl group, the alkyl group of Y preferably has 1 to 5 carbon atoms, more preferably 1 to 3 carbon atoms. I wish. When Y is an alkyl group, examples of the oxyalkylene group-containing compound (a3) ​​include polyoxyalkylene groups. Triethylene glycol monomethyl ether, polyethylene glycol lauryl ether, Polyethylene glycol cetyl ether, polyethylene glycol stearyl ether, Polyethylene glycol nonylphenyl ether, polyethylene glycol tridecyl ether ether, polyethylene glycol oleyl ether, polyethylene glycol octyl ether phenyl ether, polyoxyethylene oleyl cetyl ether, polypropylene glycol monomethyl ether and the like.

[0031] When Y is a (meth)acryloyl group, the oxyalkylene group-containing compound (a3) ​​is It is expressed by equation (3).

[0032] H-(OX)nOC(=O)-CR=CH2...Formula (3)

[0033] In formula (3), X is an alkylene group, n is 1 or more, and R is a hydrogen atom or a methyl group. In addition, in formula (3), "-C(=O)-" is a carbonyl group, and "-C(O)- " is sometimes abbreviated. In formula (3), details and preferred embodiments of X and n are the same as those described for formula (1). is the same as:

[0034] The oxyalkylene group-containing compound (a3) ​​represented by the formula (3) is, for example, a polyethylene. Ethylene glycol mono(meth)acrylate, polypropylene glycol mono(meth)acrylate Acrylate, Poly(ethylene glycol-propylene glycol) mono(meth)acrylate acrylate, poly(ethylene glycol-tetramethylene glycol) mono(meth)acrylate Poly(propylene glycol-tetramethylene glycol) mono(meth)acrylate Examples include

[0035] When Y is an allyl group, examples of the oxyalkylene group-containing compound (a3) ​​include poly Ethylene glycol monoallyl ether, polypropylene glycol monoallyl ether , poly(ethylene glycol-propylene glycol) monoallyl ether, etc. do.

[0036] When Y is an acyl group, the acyl group preferably has 10 to 30 carbon atoms, and more preferably has 12 to 18 carbon atoms. For example, polyethylene glycol monolaurate, polypropylene glycol monolaurate, Nolaurate, Poly(ethylene glycol-propylene glycol) monolaurate, Poly Examples include polyethylene glycol monostearate and polyethylene glycol monooleate. Can be obtained.

[0037] The weight average molecular weight of the oxyalkylene group-containing compound (a3) ​​is preferably 100 to 20,000. It is preferably 200 to 10,000, and more preferably 400 to 4,000. When the weight average molecular weight of the sialic alkylene group-containing compound (a3) ​​is less than the lower limit, The anti-bacterial adhesion performance of the membrane tends to be difficult to exhibit. If the weight average molecular weight of 3) exceeds the upper limit, the durability of the cured coating film, such as water resistance, decreases. In addition, the hardness of the outermost coating material tends to be inferior, which is undesirable from a practical standpoint.

[0038] The weight average molecular weight of the urethane (meth)acrylate is preferably 1,000 to 100,000. The weight average molecular weight is preferably less than the lower limit, and more preferably 2,000 to 50,000. If the weight average molecular weight exceeds the upper limit, the anti-bacterial adhesion performance tends to decrease. This tends to reduce the hardness of the coating film, which is not practically preferable.

[0039] The number average molecular weight and weight average molecular weight are calculated based on the molecular weight of standard polystyrene. The weight average molecular weight was measured using a high-performance liquid chromatograph (Waters, "ACQUITY APC system) with column: ACQUITY APC XT 450 x 1, AC 1 x ACQUITY APC XT 200, 2 x ACQUITY APC XT 45 It is measured by using four in series.

[0040] The alkylene oxide in the component (A) of the present composition has the following advantages: It is preferable that the monomer is ethylene oxide. The component (A) in the present composition may be of one type, or of two or more types in combination. Component (A) in this composition can impart high scratch resistance and alcohol resistance to the cured coating. From this viewpoint, it is preferably bifunctional or more, and more preferably trifunctional or more.

[0041] [(B) Component] The composition comprises a tri- or higher functional (meth)acrylate (B) that does not contain an alkylene oxide. Component (B) contributes to improving the adhesion, scratch resistance, and alcohol resistance of the composition. Ingredients. Examples of the component (B) include trimethylolpropane tri(meth)acrylate, Pentaerythritol tri(meth)acrylate, polyurethane tri(meth)acrylate , polyepoxy tri(meth)acrylate and polyester tri(meth)acrylate, etc. tri(meth)acrylate; ditrimethylolpropane tetra(meth)acrylate, Pentaerythritol tetra(meth)acrylate, Polyepoxy tetra(meth)acrylate tetra(meth)acrylates such as tetra(meth)acrylate and polyester tetra(meth)acrylate; Dipentaerythritol penta(meth)acrylate and tripentaerythritol penta(meth)acrylate Penta(meth)acrylates such as dipentaerythritol hexa(meth)acrylate; tripentaerythritol hexa(meth)acrylate and tripentaerythritol hexa(meth)acrylate Hexa(meth)acrylate; Tripentaerythritol hepta(meth)acrylate, Poly(meth)acrylate with 7 or more functional groups such as tripentaerythritol octa(meth)acrylate Poly(meth)acrylate; Polyepoxy with 3 or more functional groups; Poly(meth)acrylate with 3 or more functional groups Examples of the ester poly(meth)acrylates include modified caprolactones. do. The component (B) is capable of imparting high scratch resistance and alcohol resistance to the cured coating of the composition. From this viewpoint, it is preferable that the copolymer is not modified with caprolactone or the like, and has four or more functional groups. It is more preferable that the functional group is 5 or more, and it is particularly preferable that the functional group is 5 or more. The component (B) may be one type, or two or more types may be used in combination.

[0042] The content of the above component (B) is such that the double bond equivalent of the radical polymerizable compound in the composition is 5. 0 mmol / g or more, and the alkylene oxide equivalent is 4.0 mmol / g or more. Although there is no particular limitation, for example, 10 to 100 parts by weight of the above component (A) may be used. The amount is preferably 900 parts by weight, more preferably 10 to 700 parts by weight, and particularly preferably The amount of the stearate used is preferably 10 to 500 parts by weight, and more preferably 10 to 300 parts by weight. This provides the cured film with excellent scratch resistance.

[0043] [(C) component] The composition may contain a surface conditioner (C) to improve the smoothness of the cured coating surface. Examples of the (C) component include acrylic leveling agents, vinyl leveling agents, and silicone leveling agents. Examples of the (C) component include a silicone-based leveling agent and a fluorine-based leveling agent. It is preferable to use a silicone-based leveling agent or a fluorine-based leveling agent, which have high tension reducing ability. When using a silicon-based leveling agent, it is particularly preferable to use an ether-modified product. It is nice.

[0044] The content of the above component (C) is 0.0 based on 100 parts by weight of the solid content in the composition. The amount is preferably 1 to 10 parts by weight, more preferably 0.05 to 5 parts by weight, and particularly preferably The content is usually 0.1 to 5 parts by mass.

[0045] [Other ingredients] The present composition may contain, as necessary, other polymerizable components other than the components (A), (B) and (C). The other polymerizable components may include the following: (Meth)acryloyl group-containing monomers are preferred. The following are examples of the monofunctional (meth)acrylate, bifunctional (meth)acrylate, and (meth)acrylic acid. Mido is an example.

[0046] Specific examples of monofunctional (meth)acrylates include methyl (meth)acrylate, ethyl (Meth)acrylate, propyl (meth)acrylate, butyl (meth)acrylate, Pentyl (meth)acrylate, hexyl (meth)acrylate, heptyl (meth)acrylate acrylate, octyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, 2-Hydroxyethyl (meth)acrylate, 2-Hydroxypropyl (meth)acrylate acrylate, 4-hydroxybutyl (meth)acrylate, benzyl (meth)acrylate, Resole (meth)acrylate, dicyclopentenyl (meth)acrylate, dicyclopentenyl phenyloxyethyl (meth)acrylate, phenyl (meth)acrylate, phenoxy Diethyl (meth)acrylate, 7-amino-3,7-dimethyloctyl (meth)acrylate acrylate, 2-ethylhexyl (meth)acrylate, ethyl diethylene glycol (meth ) acrylate, dimethylaminoethyl (meth)acrylate, diethylaminoethyl ( (meth)acrylate, lauryl (meth)acrylate, polyepoxy mono (meth)acrylate acrylate, polyester mono(meth)acrylate, etc.

[0047] A specific example of a bifunctional (meth)acrylate is 1,4-butanediol di(meth)acrylate. Acrylate, 1,6-Hexanediol di(meth)acrylate, 1,4-Cyclohexa Tricyclodecanediol di(meth)acrylate, tricyclodecanediyldimethylene di(meth)acrylate acrylate, bisphenol A di(meth)acrylate, hydrogenated bisphenol A di(meth)acrylate Acrylates, Bisphenol F di(meth)acrylate, 1,6-Hexanediol di (Meth)acrylate, polycarbonate di(meth)acrylate, or monomers thereof Polycaprolactone adducts, polycarbonate adducts, polyepoxydi(meth)acrylic acrylate, polyester di(meth)acrylate, etc.

[0048] Specific examples of (meth)acrylamide include (meth)acrylamide, isobutoxymethylene, and the like. t-octyl(meth)acrylamide, t-octyl(meth)acrylamide, diacetone(meth ) Acrylamide, etc.

[0049] The other polymerizable components may be used alone or in combination of two or more.

[0050] The amount of other polymerizable components added is not particularly limited as long as it does not impair the performance. The amount is preferably 0 to 50 parts by mass, more preferably 0 to 30 parts by mass, based on 100 parts by mass of the solid content of the composition. It is more preferable that the amount is not more than 10 parts by mass, and particularly preferably 0 to 10 parts by mass.

[0051] The present composition may contain, as necessary, a non-curable resin, a photopolymerization initiator, a diluent, etc., within the range that does not impair the performance. , additives, thermal polymerization initiators, UV absorbers, light stabilizers, silane coupling agents, inorganic fine particles , antioxidants, anti-yellowing agents, bluing agents, pigments, dyes, defoamers, thickeners, anti-settling agents , antistatic agents, antifogging agents, antibacterial agents, antifungal agents, antiviral agents, antiallergen agents, polymerization inhibitors , etc.

[0052] [Non-curing resin] Examples of non-curable resins include (meth)acrylic polymers and (meth)acrylonitrile. -based polymers, butadiene-based polymers, urethane-based polymers, polyester-based polymers, polyamide based polymers, polyamideimide based polymers and phenol based polymers.

[0053] [Photopolymerization initiator] The photopolymerization initiator is not particularly limited as long as it generates radicals by the action of light. For example, diethoxyacetophenone, 2-hydroxy-2-methyl-1-phenylpropane Propan-1-one, benzyl dimethyl ketal, 4-(2-hydroxyethoxy)phenyl 1-Hydroxycyclohexylphenyl Ketone, 1-[4-(2-hydroxyethoxy)-phenyl]-2-hydroxy-2-methyl 2-Methyl-2-morpholino(4-thiomethylphenyl ) Propan-1-one, 2-benzyl-2-dimethylamino-1-(4-morpholinophenone 2-Hydroxy-2-methyl-1-[4-(1-methylvinyl)phenyl acetophenones such as benzoin, benzoin methyl ether, Benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl Benzoins such as benzoyl ether; benzophenone, methyl o-benzoylbenzoate, 4-fluoro phenylbenzophenone, 4-benzoyl-4′-methyl-diphenyl sulfide, 3, 3',4,4'-Tetra(t-butylperoxycarbonyl)benzophenone, 2,4, 6-Trimethylbenzophenone, 4-benzoyl-N,N-dimethyl-N-[2-(1- Oxo-2-propenyloxy)ethyl]benzenemethanaminium bromide, (4-Benzene Benzophenones such as 2-isopropyl benzyl trimethyl ammonium chloride; Pilthioxanthone, 4-isopropylthioxanthone, 2,4-diethylthioxanthone thioxanthone, 2,4-dichlorothioxanthone, 1-chloro-4-propoxythioxanthone, 2 -(3-Dimethylamino-2-hydroxy)-3,4-dimethyl-9H-thioxanthone Thioxanthones such as 2,4,6-trimethylbenzoyl-di Phenylphosphine oxide, bis(2,6-dimethoxybenzoyl)-2,4,4 -Trimethyl-pentylphosphine oxide, bis(2,4,6-trimethylbenzo acylphosphine oxides such as (phenyl)-phenylphosphine oxide; These photopolymerization initiators may be used alone or in combination of two or more. It is also possible.

[0054] In addition, as an auxiliary for the photopolymerization initiator, triethanolamine, triisopropanol Amines, 4,4′-dimethylaminobenzophenone (Michler's ketone), 4,4′-diamine 2-Dimethylaminoethylbenzoic acid, 4-Dimethylaminobenzoate Ethyl 4-dimethylaminobenzoate, (n-butoxy)ethyl 4-dimethylaminobenzoate, Isoamyl benzoate, 2-ethylhexyl 4-dimethylaminobenzoate, 2,4-diethylaminobenzoate It is also possible to use thioxanthone, 2,4-diisopropylthioxanthone, etc. in combination. These auxiliary agents may be used alone or in combination of two or more.

[0055] The content of the photopolymerization initiator is 0.01 to 100 parts by mass of the solid content in the composition. The amount is preferably 1 to 10 parts by weight, more preferably 1 to 10 parts by weight, and particularly preferably If the content is too small, curing is insufficient and it is difficult to form a coating film. Too much of it tends to cause yellowing of the cured coating film, which can lead to coloring problems. There is a direction.

[0056] [Diluent] In the active energy ray-curable composition of the present invention, the viscosity at the time of coating may be appropriately adjusted as necessary. In order to make the mixture more uniform, it is preferable to use a diluent such as water or an organic solvent. It is preferred to use

[0057] Organic solvents include alcohol-based solvents, glycol-based solvents, hydrocarbon-based solvents, and ester-based solvents. Examples of the alcohol-based solvent include methacrylic acid, ... Alcohol, ethanol, isopropyl alcohol, n-butanol, isobutanol, octadecyl alcohol Examples of alcohol include ethanol, n-propyl alcohol, and acetylacetone alcohol. The alcohol solvents are ethylene glycol, ethylene glycol monomethyl ether, Ethylene glycol monoethyl ether, Ethylene glycol mono n-propyl ether, Ethylene glycol mono-n-butyl ether, diethylene glycol monomethyl ether , diethylene glycol monoethyl ether, propylene glycol monomethyl ether , propylene glycol monoethyl ether, propylene glycol monobutyl ether , Ethylene glycol monoethyl ether acetate, Ethylene glycol monomethyl ether propylene glycol monoethyl ether acetate, propylene glycol Examples of hydrocarbon solvents include benzene, ethyl ether, and ethyl ether acetate. Examples of the ester solvent include methyl acetate, methyl methacrylate ... Examples of the acetoacetate include ethyl acetate, butyl acetate, methyl acetoacetate, and ethyl acetoacetate. Ketone solvents include acetone, methyl ethyl ketone, methyl isobutyl ketone, Examples of the ether solvent include ethyl ether, butyl ether, etc. , methyl cellosolve, ethyl cellosolve, dioxane, furan, tetrahydrofuran, etc. Examples include: The organic solvents may be used alone or in combination of two or more kinds.

[0058] When the present composition contains a diluent, the coating workability when applying the present composition to a substrate and the coating quality of the formed composition are deteriorated. The smoothness and uniformity of the film and the cured film thereof, as well as the adhesion of the cured film to the substrate, are improved. When the composition contains a diluent, the concentration of non-volatile components in the composition is adjusted to suit the application method. The lower the concentration of the non-volatile components, the thinner the coating film formed. The smoothness and uniformity of the cured film (cured layer) and the adhesion between the substrate and the cured film tend to be good. The higher the concentration of non-volatile components, the greater the effect of suppressing sagging when applying the composition to a substrate. There is a tendency for it to be good.

[0059] The ratio of the dilution solvent to the entire composition is not particularly limited, but is preferably 0 to 90% by mass. More preferably, it is 10 to 90% by mass, further preferably, it is 20 to 90% by mass, and particularly preferably The range is 30 to 90% by mass, and most preferably 30 to 80% by mass. This makes it possible to obtain a composition with excellent coatability.

[0060] The double bond equivalent of the present composition is the double bond equivalent of all the radical polymerizable compounds contained in the composition. This means the total concentration of polybonds, calculated using the formula below, and added to the proportion of the compound. It can be calculated by adding them together.

[0061] Double bond equivalent of the composition (mmol / g) = Σ{((meta) Number of acryloyl groups) × 1000 × (mass fraction of each radical polymerizable compound in the composition) / ( (Molecular weight of each radical polymerizable compound)

[0062] The alkylene oxide equivalent of the composition is the total amount of alkylene oxides contained in the composition. This means the alkylene oxide modification number of a compound having an oxide moiety, and is calculated by the following formula: The calculation can be done by adding up the results calculated in the proportion of the compound.

[0063] Alkylene oxide equivalent of the composition (mmol / g) = Σ{(alkylene oxide equivalent of each compound) (Oxide modification number) × 1000 × (mass fraction of each compound in the composition) / (molecular weight of each compound amount)}

[0064] [Method of producing the composition] The composition comprises an alkylene oxide-containing (meth)acrylate (A), an alkylene oxide-containing (meth)acrylate (B), and an alkylene oxide-containing (meth)acrylate (C). (B) a trifunctional or higher (meth)acrylate that does not contain oxide, and a surface conditioner as required It can be produced by mixing (C) and other components.

[0065] [Cured product] The cured product according to one embodiment of the present invention (hereinafter also referred to as the present cured product) is a cured product of the present composition. The present cured product can be obtained by curing the present composition. The curing method may be a method of irradiating the composition with active energy rays or a method of curing the composition by heating. The method of curing using moisture in the air and the temperature applied to the substrate are important factors in determining productivity. From this viewpoint, a method of irradiating the present composition with active energy rays is preferred.

[0066] The composition can be applied by, for example, brush coating, spray coating, or dip coating. Methods such as spin coating, curtain coating, and bar coating can be used. To adjust the strength, the composition may be heated or diluted with a subcritical fluid before painting. The thickness of the coating film of the present composition is preferably 0.001 to 1.001 mm from the viewpoints of the curability and abrasion resistance of the present composition. The thickness is preferably from 0.02 mm to 0.05 mm, and more preferably from 0.002 mm to 0.05 mm. The thickness is preferably 0.004 mm or more and 0.03 mm or less.

[0067] When a coating film of the composition is irradiated with active energy rays, it hardens to give a hardened coating. Examples of active energy rays include α rays, β rays, γ rays, and ultraviolet rays. Therefore, ultraviolet rays are preferred as the active energy rays. High pressure mercury lamps, high pressure mercury lamps, ultra-high pressure mercury lamps, xenon lamps, metal halide lamps Examples of UV lamps include LEDs, magnetron-based electrodeless UV lamps, and LEDs.

[0068] The active energy rays may be irradiated in an air atmosphere or in an inert gas atmosphere such as nitrogen or argon. The irradiation may be performed in an atmosphere. The conditions for the ionization were, for example, a high-pressure mercury lamp with a wavelength of 340 to 380 nm was used, with an integrated light intensity of 10 0~3000mJ / cm 2 It is preferable to irradiate so that When the present composition contains a diluent, the diluent is removed before the present composition is irradiated with active energy rays. To remove the fluorine-containing compound, the composition may be subjected to a heat treatment. This heat treatment may be performed using a near infrared lamp. This can be achieved by irradiation with heat, circulation of hot air, etc.

[0069] [Laminate] The laminate according to one embodiment of the present invention (hereinafter also referred to as "the laminate") comprises a substrate and the above-described The laminate has a layer made of a cured material (hereinafter, also referred to as a "cured material layer"). It is preferable that the cured layer is located on the outermost surface. If another resin layer or metal layer is provided between the substrate and the cured layer, It may have.

[0070] The substrates include glass substrates, zinc-plated steel sheets, zinc alloy-plated steel sheets, stainless steel sheets, Metal substrates such as tin-plated steel sheets; polymethyl methacrylate resin, polycarbonate resin, poly Ester resin, polystyrene resin, ABS resin, AS resin, polyamide resin, polyaryl resin, polyurethane resin, polyvinyl resin, triacetyl cellulose, polymethacrylate Examples of the resin substrate include polyallyl imide resin and polyallyl diglycol carbonate resin. In addition to resin, the resin base material contains ultraviolet absorbers, light stabilizers, plasticizers, antistatic agents, flame retardants, and reinforcements. The composition may contain additives such as a binder, a filler, a colorant, a lubricant, a foaming agent, a slip agent, and a curing catalyst.

[0071] If necessary, a primer layer may be present on the substrate to improve adhesion, etc. For decoration, a colored layer or a metal thin film layer may be present. It is also possible for the adhesive layer to have a functional layer, such as an adhesive layer, on the side opposite to the adhesive side. The present laminate can be produced, for example, by applying the present composition to a substrate and curing it. Before applying the composition, a primer may be applied to the substrate, or the substrate may be coated with a primer by vacuum deposition or sputtering. A metal thin film layer may be provided by using the above method. The coating method and curing method may be the same as those for the cured product.

[0072] [Application] This composition is suitable for use in medical facilities, food factories, clothing manufacturing plants, schools, stations, banks, convenience stores, etc. Items that people may touch, from industrial products to everyday items, in offices, public facilities, etc. It is particularly suitable for use as a surface protective coating material for mobile phones, household appliances, etc. It can be suitably used in electrical appliances, cosmetic containers, automotive interior materials, decorative sheets, etc. EXAMPLES

[0073] The present invention will be described in more detail below with reference to examples and comparative examples. In the explanation, "parts" refers to "parts by mass". Measurements and evaluations are as follows. I did it in the following way.

[0074] [Measurement and evaluation methods] <Low bacterial adhesion> Staphylococcus aureus (NBRC12732) and Escherichia coli (NBRC3972) were incubated at 37°C in advance. Culture overnight and add phosphate buffered saline (PBS) until the OD600 is in the range of 0.4 to 0.6. A diluted culture solution was prepared using a pH 7.0 solution. A test piece was cut out of the cured coating film and measured The pieces were attached to the inside of a TPP cell culture flask, and 100 mL of diluted culture medium was added. After the bacteria were attached, the diluted culture medium was removed by suction, and the plate was rinsed. The inside of the flask was washed three times with 100 mL of acid buffered saline (pH 7.0). After removing any remaining droplets from the inside of the container, the ATP measuring kit was used with the tip of a cotton swab moistened with ion-exchanged water. The surface of the test piece was wiped with a Kikkoman Lucipack A3 Surface and irradiated with light. The amount of attached bacteria was measured in relative light units (RLU). (Judgment criteria) A: RLU is 2.0 × 10 3 is less than. B: RLU is 2.0 × 10 3 Above 5.0×10 3 Less than or equal to. C: RLU is 5.0 × 10 3 That's all.

[0075] <Appearance> The appearance of the evaluation sample was evaluated visually, and the judging criteria were as follows: (Judgment criteria) A: No abnormalities such as whitening, cracks, or blisters are observed, and a transparent, smooth coating film has been formed. B: Slight bleaching is observed. C: Abnormalities such as whitening, cracks, and swelling are observed.

[0076] <Adhesion> The adhesion of the evaluation sample was evaluated as follows using the cross-cut tape method according to JIS K 5400. It was evaluated based on value. (Judgment criteria) A: No peeling in the cross-cut test. B: In the cross-cut test, there are chipped grooves or peeled off squares in less than half of the test area. do. C: In the cross-cut test, more than half of the test area had chipped cuts or peeled off squares. do.

[0077] <Scratch resistance> The scratch resistance of the evaluation sample was measured by attaching it to a flat surface friction tester manufactured by Coating Tester Co., Ltd. The steel wool used was #000 from Bonstar Sales Co., Ltd., and the load was 250g / cm 2 , 10 times The paint film was rubbed under the same conditions and the scratches on the film were visually observed. The evaluation criteria are as follows: (Judgment criteria) A: 5 or less scratches B: 5 to 10 scratches C: 10 or more scratches

[0078] <Alcohol resistance> The alcohol resistance of the evaluation sample was evaluated by measuring the alcohol content of the test specimen in 80% ethanol solution adjusted to 40°C. The coating was immersed in the solution for 24 hours, and then air-dried. The appearance and adhesion of the coating were evaluated using the above method. Evaluated.

[0079] <Method of preparing polymer> The method for preparing the (meth)acrylate oligomer used in the examples and comparative examples is explained below. The (meth)acrylate oligomer (A-2-1) is a (meth)acrylate This corresponds to oligomer (A). <Synthesis Example 1: Preparation of (meth)acrylate oligomer (A-2-1)> First, add isophorone diacetate to a four-neck flask equipped with a thermometer, stirrer, and water-cooled condenser. Isocyanate (a1) (isocyanate group content 37.8%) 99.3g (0.45m ol) and 2,6-di-tert-butylcresol 1.5g, dibutyltin dilaurelate Add 0.1g of dipentaerythritol pentaacrylate (a2) at 60°C or less. (0.54 mol) was reacted at 60° C. for 2 hours. Dipentaerythritol pentaacrylate (a2) is a mixture of dipentaerythritol pentaacrylate and dipentaerythritol pentaacrylate. Mixture of thritol hexaacrylate (hydroxyl value 51.0 mg KOH / g) 590. After the reaction started, when the residual isocyanate group reached 2.2%, Polyethylene glycol (A3) (number average molecular weight 993.1, ethylene oxide adduct) Mole number 22, hydroxyl value 113 mgKOH / g) 310.7 g (0.31 mol) at 55°C The mixture was then dropped at 60°C for 4 hours, and the remaining isocyanate groups were reduced to 0.1%. The reaction is terminated by the above procedure, and a resin composition containing a (meth)acrylate oligomer (A-2-1) is obtained. (Weight average molecular weight: 3,700) The resin composition was obtained by mixing (meth)acrylate oligomers. - (A-2-1) 66.6%, (meth)acrylate monomer (B-1) diphenyl ether It contained 33.4% taerythritol hexaacrylate.

[0080] <Synthesis Example 2: (Meth)acrylate Oligomer Not Containing Alkylene Oxide (B-2 ) Adjustment > First, add isophorone diacetate to a four-neck flask equipped with a thermometer, stirrer, and water-cooled condenser. Isocyanate (a1) (isocyanate group content 37.8%) 150.0 g and 2,6- Contains 0.8g of di-tert-butyl cresol and 0.05g of dibutyltin dilaurate. Then, at 60℃ or less, react with pentaerythritol triacrylate (a2) at 60℃ for 4 hours. Here, the pentaerythritol triacrylate (a2) was reacted with pentaerythritol. A mixture of erythritol triacrylate and pentaerythritol tetraacrylate (hydroxyl group The mixture was charged with 850 g of sucrose (value: 120.0 mg KOH / g). After the reaction starts, the reaction is stopped when the remaining isocyanate groups reach 0.1%. A resin composition containing (meth)acrylate (B-2) was obtained (weight average molecular weight 1,10 0). The resin composition thus obtained was prepared by mixing urethane (meth)acrylate (B-2) in an amount of 5 1.1%, pentaerythritol triacetate as (meth)acrylate monomer (B-3) It contains 48.9% of a mixture of acrylate and pentaerythritol tetraacrylate. Ta.

[0081] [Example 1] <Adjustment of Composition> (A) Component is trimethylolpropane trimethylol modified with 15 mol of ethylene oxide. 11 parts of acrylate (MIWON, product name: Miramer M3150) and (B ) Dipentaerythritol hexaacrylate (manufactured by MIWON, product name: Miramer M600) 8 parts, and ether-modified silicone leveller as component (C) 0.34 parts of a coating agent (manufactured by BYK Japan, product name: BYK-300) and As the initiator, 1-hydroxycyclohexyl-phenyl-ketone (IGM RESIN One part of Omirad 184 (manufactured by S Company), butyl acetate, n-butanol, toluene The composition was prepared by mixing 12 parts of each of the above.

[0082] [Example 2] As the component (A), 6 parts of Miramer M3150 and the (Meta 3 parts of a resin composition containing an acrylate oligomer (A-2-1), and (B) component. A composition was prepared in the same manner as in Example 1, except that Miramer M600 was used in place of 10 parts. The evaluation samples were prepared.

[0083] [Example 3] As the component (A), 4 parts of Miramer M3150 and the (Meta 4.5 parts of a resin composition containing an acrylate oligomer (A-2-1) and 4.5 parts of a resin composition containing an acrylate oligomer (A-2-2). The same procedure as in Example 1 was repeated except that the amount of Miramer M600 was 10.5 parts. A composition was prepared and an evaluation sample was prepared.

[0084] [Example 4] As the component (A), 5 parts of Miramer M3150 and the (Meta 4.5 parts of a resin composition containing an acrylate oligomer (A-2-1) and 4.5 parts of a resin composition containing an acrylate oligomer (A-2-2). As component (C), 9.5 parts of Miramer M600 and 9.5 parts of fluorine-based leveling agent Except for the use of 0.17 parts of a coating agent (manufactured by DIC Corporation, product name: Megafac F556), In the same manner as in Example 1, a composition was prepared and an evaluation sample was produced.

[0085] [Comparative Example 1] The (A) and (C) components were not used, and the (meth) 25 parts of acrylate oligomer (B-2) and 1-[4-(2-hydroxyphenyl)-2-propanediol (1-phenylpropanediol) as a photopolymerization initiator were used. hydroxyethoxy)-phenyl]-2-hydroxy-2-methyl-1-propan-1-ol (IGM RESINS, product name: Omirad 2959) was used in part. In the same manner as in Example 1, a composition was prepared and an evaluation sample was produced.

[0086] [Comparative Example 2] As the component (A), 8 parts of Miramer M3150 and the (Meta ) 8 parts of acrylate oligomer (A-2-1) and Miramer as component (B). A composition was prepared in the same manner as in Example 1, except that 3 parts of M600 were used, and an evaluation sample was prepared. Made.

[0087] <Evaluation sample> The prepared composition was applied to a 3 mm thick ABS plate, and the cured coating thickness after drying was 0.015 mm. The coated substrate was then placed in an oven at 60°C for 3 minutes. The organic solvent was evaporated by heating. Furthermore, a high-pressure mercury lamp was used in air to evaporate the organic solvent. Peak irradiance from 100mW / cm2 to 400nm 2 , the cumulative light intensity is 1000mJ / cm 2 The ABS plate was then irradiated with ultraviolet light of 1000 ohms to obtain an ABS plate with a hardened coating.

[0088] <Evaluation> The obtained evaluation samples were evaluated for initial appearance (before durability testing), adhesion, scratch resistance, fineness, The anti-bacterial adhesion was evaluated. In addition, the appearance and adhesion after the alcohol resistance test were evaluated. Results The results are shown in Table 1. However, Comparative Example 2 had low alcohol resistance and therefore low bacterial adhesion. No testing was performed.

[0089] [Table 1]

[0090] As shown in Table 1, the compositions of Examples 1 to 4 had excellent appearance, adhesion, scratch resistance, and alcohol resistance. It has excellent antibacterial and anti-bacterial properties and satisfies the requirements for use as a coating material on the surfaces of various substrates. Ta. On the other hand, in Comparative Example 1, the alkylene oxide equivalent was low, and therefore the bacterial adhesion was low. In Comparative Example 2, the double bond equivalent was low, so the scratch resistance and alcohol resistance of the coating film were low. .

[0091] From the above examples, it can be seen that the present invention has excellent adhesion, scratch resistance, and alcohol resistance, and further has low bacterial resistance. Active energy ray polymerizable composition capable of obtaining a cured film having good adhesion, and the cured film This makes it possible to provide products that meet the needs of the customer.

Claims

1. The composition comprises an alkylene oxide-containing (meth)acrylate (A) and an alkylene oxide-free tri- or higher functional (meth)acrylate (B), The (meth)acrylate (A) contains an alkylene oxide-containing (meth)acrylate monomer (A-1) and an alkylene oxide-containing (meth)acrylate oligomer (A-2), The (meth)acrylate oligomer (A-2) is a urethane (meth)acrylate obtained from a polyisocyanate (a1), a hydroxyl group-containing (meth)acrylate (a2), and an oxyalkylene group-containing compound (a3), The alkylene oxide in the (meth)acrylate (A) is ethylene oxide, An active energy ray-curable composition, wherein the radical polymerizable compound has a double bond equivalent of 5.0 mmol / g or more and an alkylene oxide equivalent of 4.0 mmol / g or more.

2. The active energy ray-curable composition according to claim 1 , further comprising a surface conditioner (C).

3. A cured product comprising the active energy ray-curable composition according to claim 1 or 2.

4. A laminate comprising a substrate and the cured product according to claim 3.

5. A method for producing a cured product, comprising curing an active energy ray-curable composition containing an alkylene oxide-containing (meth)acrylate (A) and an alkylene oxide-free tri- or higher functional (meth)acrylate (B), The (meth)acrylate (A) contains an alkylene oxide-containing (meth)acrylate monomer (A-1) and an alkylene oxide-containing (meth)acrylate oligomer (A-2), The (meth)acrylate oligomer (A-2) is a urethane (meth)acrylate obtained from a polyisocyanate (a1), a hydroxyl group-containing (meth)acrylate (a2), and an oxyalkylene group-containing compound (a3), The alkylene oxide in the (meth)acrylate (A) is ethylene oxide, A method for producing a cured product, wherein the radically polymerizable compound has a double bond equivalent of 5.0 mmol / g or more and an alkylene oxide equivalent of 4.0 mmol / g or more.

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