Method for manufacturing (meth)acrylic resin solution

Abstract

To provide a novel method for producing (meth)acrylic resin solutions. [Solution] A method for producing a (meth)acrylic resin solution is disclosed. The method for producing the (meth)acrylic resin solution comprises the step of polymerizing a monomer containing a (meth)acrylate compound in a solvent having a cyclic ether group and not having radical polymerizable groups to obtain a (meth)acrylic resin solution.

Description

Technical Field

[0001] The present disclosure relates to a method for producing a (meth)acrylic resin solution. Background Art

[0002] (Meth)acrylic resins are excellent in transparency and have high oil resistance, weather resistance and the like, for example, so they are used in various fields. Generally, (meth)acrylic resins are produced by polymerizing a (meth)acrylate compound in a hydrocarbon solvent such as xylene or toluene (see, for example, Patent Document 1). Prior Art Literature Patent Documents

[0003] Patent Document 1 Japanese Unexamined Patent Publication No. 2012-184364 Summary of Invention Problem to be Solved by Invention

[0004] An object of the present disclosure is to provide a novel method for producing a (meth)acrylic resin solution. Means for Solving Problem

[0005] The present disclosure includes the following [1] to [4]. [1] A method for producing a (meth)acrylic resin solution, comprising a step of polymerizing a monomer containing a (meth)acrylate compound in a solvent having a cyclic ether group and no radical polymerizable group to obtain a (meth)acrylic resin solution, the method for producing a (meth)acrylic resin solution. [2] The method for producing a (meth)acrylic resin solution according to [1], wherein the (meth)acrylate compound comprises a (meth)acrylate having a fluorine-containing organic group and a (meth)acrylate having a cyclic ether group, the method for producing a (meth)acrylic resin solution according to [1]. [3] The (meth)acrylate having a fluorine-containing organic group is a (meth)acrylate having a fluoroalkyl group. [2] A method for producing the (meth)acrylic resin solution described above. [4] The (meth)acrylate having a cyclic ether group is at least one selected from the group consisting of (meth)acrylate having an epoxy group, (meth)acrylate having an alicyclic epoxy group, and (meth)acrylate having an oxetanyl group. [2] A method for producing the (meth)acrylic resin solution described above. [Effects of the Invention]

[0006] This disclosure provides a novel method for producing a (meth)acrylic resin solution. The resulting (meth)acrylic resin solution contains a solvent having a cyclic ether group. Therefore, the (meth)acrylic resin solution of this disclosure has the advantage that it can be directly used in cationic polymerization reactions or anionic polymerization without the need for isolation of the (meth)acrylic resin (without the need for removal and substitution of the solvent). [Modes for carrying out the invention]

[0007] The embodiments of this disclosure are described below. However, this disclosure is not limited to the embodiments described below.

[0008] In this specification, numerical ranges indicated using "~" represent a range that includes the numbers before and after "~" as the minimum and maximum values, respectively. In numerical ranges described in stages in this specification, the upper or lower limit of one stage of the numerical range may be replaced with the upper or lower limit of another stage of the numerical range. Also, in numerical ranges described in this specification, the upper or lower limit of that numerical range may be replaced with the values ​​shown in the examples. Furthermore, the upper and lower limits described individually can be combined in any way. In the notation "A~B" for a numerical range, the numbers A and B at both ends are included in the numerical range as the lower and upper limits, respectively. In this specification, for example, the description "10 or more" means "10" and "numbers greater than 10," and this applies even if the numbers are different. Also, for example, the description "10 or less" means "10" and "numbers less than 10," and this applies even if the numbers are different.

[0009] In this specification, (meth)acrylate compounds mean compounds having one or more (meth)acryloyl groups, and (meth)acrylic resins mean (co)polymers having at least one structural unit derived from (meth)acrylate compounds. (meth)acryloyl groups mean acryloyl groups or their corresponding methacryloyl groups. The same applies to other similar expressions such as (meth)acrylate. Furthermore, "A or B" means that either A or B may be included, or both may be included.

[0010] In this specification, a cyclic ether group means a group obtained by removing one hydrogen atom directly bonded to a carbon atom from a compound having a cyclic ether, such as an oxirane or oxetane. A cyclic ether group may be a group obtained by removing one hydrogen atom directly bonded to a carbon atom from a compound having a three-membered or four-membered cyclic ether. Examples of such cyclic ether groups include epoxy groups (oxyranyl groups), oxetanyl groups, and alicyclic epoxy groups such as epoxycyclohexyl groups (epoxy groups formed together with the two carbon atoms constituting the alicyclic ring).

[0011] The materials exemplified below may be used individually or in combination of two or more, unless otherwise specified. The amount or content of each component refers to the total amount of any multiple substances present in the composition, unless otherwise specified.

[0012] [Meth)acrylic resin solution manufacturing method] One embodiment of a method for producing a (meth)acrylic resin solution comprises the step of polymerizing a monomer containing a (meth)acrylate compound in a solvent having a cyclic ether group and no radical polymerizable groups to obtain a (meth)acrylic resin solution.

[0013] <Monomer> • (meth)acrylate compounds A (meth)acrylate compound is a compound having one or more (meth)acryloyl groups. Furthermore, a (meth)acrylate compound may not have functional groups that are reactive to solvents containing cyclic ether groups, as described later. Examples of such functional groups include amino groups, carboxyl groups, and thiol groups. In other words, a (meth)acrylate compound may be a (meth)acrylate compound that does not have amino groups, carboxyl groups, or thiol groups.

[0014] Examples of (meth)acrylate compounds include monofunctional (meth)acrylates having one (meth)acryloyl group and polyfunctional (meth)acrylates having two or more (meth)acryloyl groups. The (meth)acrylate compound may also contain monofunctional (meth)acrylates.

[0015] Examples of monofunctional (meth)acrylates include alkyl (meth)acrylates having alkyl groups such as methyl (meth)acrylate, ethyl (meth)acrylate, n-butyl (meth)acrylate, isobutyl (meth)acrylate, tert-butyl (meth)acrylate, n-hexyl (meth)acrylate, n-octyl (meth)acrylate, isooctyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, isodecyl (meth)acrylate, and dodecyl (meth)acrylate; (meth)acrylates having aromatic groups such as benzyl (meth)acrylate and phenoxyethyl (meth)acrylate; (meth)acrylates having alicyclic groups such as cyclohexyl (meth)acrylate, isobornyl (meth)acrylate, and dicyclopentanyl (meth)acrylate; (meth)acrylates having epoxy groups such as glycidyl (meth)acrylate; and 3,4-epoxy (Meth)acrylates having alicyclic epoxy groups such as cyclohexylmethyl (meth)acrylate; (meth)acrylates having oxetanyl groups such as (3-ethyloxetan-3-yl)methyl (meth)acrylate; (meth)acrylates having nitrogen-containing oxygen heterocyclic groups such as 4-(meth)acryloylmorpholine; alkoxy polyalkylene glycol (meth)acrylates such as methoxyethylene glycol (meth)acrylate, methoxytetraethylene glycol (meth)acrylate, methoxyhexaethylene glycol (meth)acrylate, and methoxyoctaethylene glycol (meth)acrylate; polyalkylene glycol mono(meth)acrylates such as tetraethylene glycol mono(meth)acrylate, hexaethylene glycol mono(meth)acrylate, and octapropylene glycol mono(meth)acrylate; (meth)acrylates having a siloxane skeleton;Examples include (meth)acrylates having fluorine-containing organic groups (fluoroalkyl groups), such as trifluoromethyl (meth)acrylate, 2,2,2-trifluoroethyl (meth)acrylate, 1,1,1,3,3,3-hexafluoro-2-propyl (meth)acrylate, perfluoroethyl methyl (meth)acrylate, perfluoropropyl methyl (meth)acrylate, perfluorobutyl methyl (meth)acrylate, perfluoropentyl methyl (meth)acrylate, perfluorohexyl methyl (meth)acrylate, perfluoroheptyl methyl (meth)acrylate, perfluorooctyl methyl (meth)acrylate, perfluorononyl methyl (meth)acrylate, perfluorodecyl methyl (meth)acrylate, perfluoroundecyl methyl (meth)acrylate, perfluorododecyl methyl (meth)acrylate, perfluorotridecyl methyl (meth)acrylate, and perfluorotetradecyl methyl (meth)acrylate.

[0016] The amount of monofunctional (meth)acrylate used may be 60% by mass or more (60-100% by mass), 80% by mass or more (80-100% by mass), or 90% by mass or more (90-100% by mass), or 100% by mass, based on the total amount of (meth)acrylate compounds.

[0017] Examples of polyfunctional (meth)acrylates include ethylene glycol di(meth)acrylate, diethylene glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, tetraethylene glycol di(meth)acrylate, polyethylene glycol di(meth)acrylate, propylene glycol di(meth)acrylate, dipropylene glycol di(meth)acrylate, tripropylene glycol di(meth)acrylate, tetrapropylene glycol di(meth)acrylate, polypropylene glycol di(meth)acrylate, ethoxylated polypropylene glycol di(meth)acrylate, 1,3-butanediol di(meth)acrylate, 1,4-butanediol di(meth)acrylate, neopentyl glycol di(meth)acrylate, 3-methyl-1,5-pentanediol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, 1,10-decanediol di(meth)acrylate Aliphatic poly(meth)acrylates such as acrylate, glycerin di(meth)acrylate, tricyclodecane dimethanol(meth)acrylate, ethoxylated 2-methyl-1,3-propanediol di(meth)acrylate, trimethylolpropane tri(meth)acrylate, ethoxylated trimethylolpropane tri(meth)acrylate; ethoxylated bisphenol A type di(meth)acrylate, propoxylated bisphenol A type di(meth)acrylate, ethoxylated Examples include aromatic poly(meth)acrylates such as bisphenol A di(meth)acrylate, ethoxylated bisphenol F di(meth)acrylate, propoxylated bisphenol F di(meth)acrylate, ethoxylated propoxylated bisphenol F di(meth)acrylate, ethoxylated fluorene type di(meth)acrylate, propoxylated fluorene type di(meth)acrylate, and ethoxylated propoxylated fluorene type di(meth)acrylate.

[0018] The amount of polyfunctional (meth)acrylate used may be 40% by mass or less (0-40% by mass), 20% by mass or less (0-20% by mass), or 10% by mass or less (0-10% by mass), based on the total amount of (meth)acrylate compounds.

[0019] In one embodiment, the monomer may comprise, as a (meth)acrylate compound (monofunctional (meth)acrylate), a (meth)acrylate having a fluorine-containing organic group and a (meth)acrylate having a cyclic ether group. The (meth)acrylate having a fluorine-containing organic group may be a (meth)acrylate having a fluoroalkyl group. The (meth)acrylate having a cyclic ether group may be, for example, at least one selected from the group consisting of a (meth)acrylate having an epoxy group, a (meth)acrylate having an alicyclic epoxy group, and a (meth)acrylate having an oxetanyl group.

[0020] By polymerizing these monomers, a (meth)acrylic resin (X) having a first structural unit derived from a (meth)acrylate having a fluorine-containing organic group and a second structural unit derived from a (meth)acrylate having a cyclic ether group can be obtained. In an adhesive composition containing, for example, a (meth)acrylate compound, an epoxy compound, and a photoacid generator, the (meth)acrylic resin (X) can act as a crosslinking agent for forming a cured product of an adhesive composition having sufficient adhesive strength and high infrared transmittance even when a (meth)acrylate having a fluorine-containing organic group is applied to the adhesive composition.

[0021] The content of the first structural unit, based on all structural units of the (meth)acrylic resin (X), may be 10 to 90 mol%, 20 to 90 mol%, 30 to 90 mol%, or 40 to 90 mol%. The content of the second structural unit, based on all structural units of the (meth)acrylic resin (X), may be 10 to 90 mol%, 10 to 80 mol%, 10 to 70 mol%, or 10 to 60 mol%.

[0022] The usage amount of the (meth)acrylate compound, based on the total amount of the monomers, may be 60 mass% or more (60 to 100 mass%), 80 mass% or more (80 to 100 mass%), or 90 mass% or more (90 to 100 mass%), and may also be 100 mass%.

[0023] Others The monomer may contain other compounds copolymerizable with the (meth)acrylate compound. Examples of other compounds include compounds having radical polymerizable groups other than the (meth)acryloyl group, such as styrene, 4-methylstyrene, vinylpyridine, vinylpyrrolidone, vinyl acetate, cyclohexylmaleimide, and phenylmaleimide.

[0024] The amount of other compounds used may be 40% by mass or less (0-40% by mass), 20% by mass or less (0-20% by mass), or 10% by mass or less (0-10% by mass), or even 0% by mass, based on the total amount of monomers.

[0025] <Solvent> The solvent is a solvent having a cyclic ether group and no radical polymerizable groups. The cyclic ether group may be an epoxy group or an oxetanyl group. Examples of solvents include those commonly used in the field of epoxy resin diluents. Another example of a solvent is an epoxy resin that is liquid at 25°C. The solvent may be, for example, an aliphatic diglycidyl ether.

[0026] In this specification, a radical polymerizable group means a group having a carbon-carbon double bond. Examples of radical polymerizable groups include (meth)acryloyl groups, vinyl groups, allyl groups, styryl groups, alkenyl groups, alkenylene groups, and maleimide groups.

[0027] Examples of aliphatic diglycidyl ethers include diglycidyl ethers having alkylene groups such as ethylene glycol diglycidyl ether, propylene glycol diglycidyl ether, neopentyl glycol diglycidyl ether, 1,4-butanediol diglycidyl ether, and 1,6-hexanediol diglycidyl ether; diglycidyl ethers having oxyalkylene groups such as diethylene glycol diglycidyl ether, tripropylene glycol diglycidyl ether, and polyethylene glycol diglycidyl ether; and diglycidyl ethers having cycloalkylene groups such as hydrogenated bisphenol A diglycidyl ether, 1,4-cyclohexanedimethanol diglycidyl ether, and diglycidyl-1,2-cyclohexanedicarboxylate.

[0028] The amount of solvent used can be appropriately determined depending on the type of monomer, reaction conditions, the proportion of solids in the (meth)acrylic resin solution, etc.

[0029] <Polymerization reaction> (Meth)acrylic resin solutions can be obtained, for example, by polymerizing monomers by radical polymerization using solution polymerization. When polymerizing monomers, thermal radical generators, additives, etc., may be added as needed.

[0030] Examples of thermal radical generators include organic peroxides such as cumene hydroperoxide, diisopropylbenzene hydroperoxide, di-t-butyl peroxide, lauroyl peroxide, benzoyl peroxide, t-butyl peroxyisopropyl carbonate, t-amyl peroxy-2-ethylhexanoate, and t-butyl peroxy-2-ethylhexanoate; and azo compounds such as 2,2'-azobis(isobutyronitrile), 1,1'-azobis(cyclohexanecarbonile), 2,2'-azobis(2,4-dimethylvaleronitrile), and dimethyl-2,2'-azobis(2-methylpropionate).

[0031] The amount of thermal radical generator added can be set appropriately according to the type of monomer, reaction conditions, etc., and is not particularly limited, but may be 100 to 200,000 ppm by mass, 1,000 to 100,000 ppm by mass, or 10,000 to 80,000 ppm by mass, based on the total amount of monomers.

[0032] Examples of additives include chain transfer agents, antioxidants, light stabilizers, weather stabilizers, UV absorbers, and radical scavengers. The amount of additives added is not particularly limited, but may be 0.001 to 2% by mass or 0.005 to 1% by mass based on the total amount of monomers.

[0033] The polymerization temperature may be 40-120°C, 50-100°C, or 60-90°C. The polymerization time may be 0.1-24 hours, 0.5-20 hours, or 1-12 hours.

[0034] <(meth)acrylic resin solution> The solid content of the (meth)acrylic resin solution may be, for example, 10 to 80% by mass, 20% or more by mass, 30% or more by mass, or 40% or more by mass, or 70% or less by mass, 65% or less by mass, or 60% or less by mass.

[0035] The viscosity of the (meth)acrylic resin solution at 25°C may be, for example, 1 to 100 Pa·s, 3 Pa·s or more, 4 Pa·s or more, or 5 Pa·s or more, and may be 90 Pa·s or less, 80 Pa·s or less, or 70 Pa·s or less. The viscosity at 25°C refers to the viscosity at 25°C measured using an E-type viscometer (manufactured by Toki Sangyo Co., Ltd., product name: VISCOMETER-TV22, applicable cone-plate rotor: 3° × R17.65).

[0036] The weight-average molecular weight (Mw) of the (meth)acrylic resin may be, for example, 1,000 to 200,000, 3,000 or more, 5,000 or more, or 10,000 or more, and may be 150,000 or less, 100,000 or less, or 60,000 or less. The weight-average molecular weight (Mw) is a polystyrene equivalent value using a calibration curve with standard polystyrene by gel permeation chromatography (GPC). The weight-average molecular weight (Mw) can be measured, for example, by the method described in the examples.

[0037] The resulting (meth)acrylic resin solution contains a solvent having a cationically polymerizable cyclic ether group. Therefore, the resulting (meth)acrylic resin solution has the advantage of being able to be directly incorporated into cationic polymerization reactions without the need for isolation of the (meth)acrylic resin (without the need for solvent removal and substitution). [Examples]

[0038] The present disclosure will be described in more detail below with reference to examples. However, the present disclosure is not limited to these examples.

[0039] [Synthesis of (meth)acrylic resin solution] The following ingredients were prepared. • (meth)acrylate compounds M-3F: Trifluoroethyl methacrylate (Light Ester M-3F, manufactured by Kyoeisha Chemical Co., Ltd.) TTA-15: 3,4-Epoxycyclohexylmethyl methacrylate (manufactured by Sun Chemical Co., Ltd.) BA: Butyl acrylate (manufactured by Toagosei Co., Ltd.) MMA: Methyl methacrylate (Acryester M, manufactured by Mitsubishi Chemical Corporation) GMA: Glycidyl methacrylate (manufactured by Mitsubishi Gas Chemical Company, Inc.) • Thermal radical generator V-601: Dimethyl-2,2'-azobis(2-methylpropionate) (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) ·solvent NPG: Neopentyl glycol diglycidyl ether (Epogosei NPG(D)) (manufactured by Yokkaichi Synthetic Co., Ltd.) BisF: Bisphenol F type epoxy resin (EPICLON® 830, manufactured by DIC Corporation, liquid at 25°C)

[0040] <Example 1> Mixture (a) was prepared by mixing 84.06 g of M-3F and 98.12 g of TTA-15 (molar ratio of M-3F / TTA-15 = 50% / 50%) with 10.17 g of V-601 and 23.72 g of NPG. Separately, solution (b) was prepared by dissolving 1.82 g of V-601 in 7.29 g of NPG.

[0041] 163.2 g of NPG was placed in a flask equipped with a stirrer, dropping funnel, condenser, thermometer, and gas inlet tube. The mixture was stirred under a nitrogen atmosphere while gas purging, and the temperature was raised to 85°C. Next, mixture (a) was added dropwise to the flask over 2 hours. After the addition was complete, the mixture was stirred at 85°C for 20 minutes, then solution (b) was added, and the mixture was stirred for a further 7 hours. Then, while continuing to stir, the mixture was cooled to room temperature (25°C) to obtain the (meth)acrylic resin solution of Example 1. The solid content concentration was 50% by mass.

[0042] <Example 2> The (meth)acrylic resin solution of Example 2 was obtained by the same procedure as in Example 1, except that 84.06 g of M-3F and 98.12 g of TTA-15 (molar ratio of M-3F / TTA-15 = 50% / 50%) were changed to 141.02 g of M-3F and 41.15 g of TTA-15 (molar ratio of M-3F / TTA-15 = 80% / 20%). The solid content concentration was 50% by mass.

[0043] <Example 3> The (meth)acrylic resin solution of Example 3 was obtained by the same procedure as in Example 1, except that 84.06 g of M-3F and 98.12 g of TTA-15 (molar ratio of M-3F / TTA-15 = 50% / 50%) were changed to 121.43 g of M-3F and 60.75 g of TTA-15 (molar ratio of M-3F / TTA-15 = 70% / 30%). The solid content concentration was 50% by mass.

[0044] <Example 4> The (meth)acrylic resin solution of Example 4 was obtained by the same procedure as in Example 1, except that 84.06 g of M-3F and 98.12 g of TTA-15 (molar ratio of M-3F / TTA-15 = 50% / 50%) were changed to 48.63 g of M-3F and 132.44 g of TTA-15 (molar ratio of M-3F / TTA-15 = 30% / 70%). The solid content concentration was 50% by mass.

[0045] <Example 5> The (meth)acrylic resin solution of Example 5 was obtained by the same procedure as in Example 1, except that 84.06 g of M-3F and 98.12 g of TTA-15 (molar ratio of M-3F / TTA-15 = 50% / 50%) were changed to 32.01 g of M-3F and 149.45 g of TTA-15 (molar ratio of M-3F / TTA-15 = 20% / 80%). The solid content concentration was 50% by mass.

[0046] <Example 6> Mixture (a) was prepared by mixing 144.38 g of M-3F and 42.13 g of TTA-15 (molar ratio of M-3F / TTA-15 = 80% / 20%) with 5.78 g of V-601 and 24.11 g of NPG. Separately, solution (b) was prepared by dissolving 1.87 g of V-601 in 7.46 g of NPG.

[0047] 162.44 g of NPG was placed in a flask equipped with a stirrer, dropping funnel, condenser, thermometer, and gas inlet tube. The flask was stirred under a nitrogen atmosphere while gas substitution was performed, and the temperature was raised to 85°C. Next, mixture (a) was added dropwise to the flask over 2 hours. After the addition was complete, the flask was stirred at 85°C for 20 minutes, then solution (b) was added, and the flask was stirred for a further 7 hours. Then, while continuing to stir, the flask was cooled to room temperature (25°C) to obtain the (meth)acrylic resin solution of Example 6. The solid content concentration was 50% by mass.

[0048] <Example 7> The (meth)acrylic resin solution of Example 7 was obtained by the same procedure as in Example 1, except that 84.06 g of M-3F and 98.12 g of TTA-15 (molar ratio of M-3F / TTA-15 = 50% / 50%) were changed to 182.17 g of M-3F (molar ratio of M-3F / TTA-15 = 100% / 0%). The solid content concentration was 50% by mass.

[0049] <Example 8> The (meth)acrylic resin solution of Example 8 was obtained by the same procedure as in Example 6, except that mixture (a) was prepared by mixing 95.41 g of BA, 82.81 g of MMA, and 11.76 g of GMA (molar ratio of BA / MMA / GMA = 45% / 50% / 5%) with 2.28 g of V-601 and 24.42 g of NPG. The solids content concentration was 50% by mass.

[0050] <Example 9> The (meth)acrylic resin solution of Example 9 was obtained by the same procedure as in Example 8, except that the solvent was changed from NPG to BisF. The solids content concentration was 50% by mass.

[0051] [Evaluation of (meth)acrylic resin solutions] (Measurement of viscosity (at 25°C)) The viscosity of (meth)acrylic resin solutions at 25°C was measured using an E-type viscometer (manufactured by Toki Sangyo Co., Ltd., product name: VISCOMETER-TV22, applicable cone-plate rotor: 3°×R17.65) with a sample volume of 0.5 to 1.0 mL, at a rotation speed of 10 rpm. The results are shown in Table 1.

[0052] (Measurement of weight-average molecular weight (Mw)) For Mw measurement, a (meth)acrylic resin solution was dissolved in tetrahydrofuran (THF) to prepare a 0.2% by mass THF solution. Mw was measured by gel permeation chromatography (GPC) and derived by conversion using a calibration curve for standard polystyrene. The GPC conditions are shown below. The results are shown in Table 1. Measuring device: Showdex® GPC-101 (manufactured by Showa Denko Corporation) Detector: Differential refractometer, Showdex RI-71S (manufactured by Showa Denko Corporation) Column: Showdex LF-804 + LF-804 (manufactured by Showa Denko Corporation) Column temperature: 40℃ Eluent: Tetrahydrofuran (THF) Flow rate: 1mL / min

[0053] (Observation of resin solution) (Meth)acrylic resin solutions were observed visually and evaluated as "A" if transparent and "B" if opaque. The results are shown in Table 1.

[0054] [Table 1]

Claims

1. The process includes a step of polymerizing a monomer containing a (meth)acrylate compound in a solvent having a cyclic ether group and no radical polymerizable groups to obtain a (meth)acrylic resin solution. A method for producing a (meth)acrylic resin solution.

2. The (meth)acrylate compound includes (meth)acrylates having a fluorine-containing organic group and (meth)acrylates having a cyclic ether group. A method for producing the (meth)acrylic resin solution according to claim 1.

3. The (meth)acrylate having a fluorine-containing organic group is a (meth)acrylate having a fluoroalkyl group. A method for producing a (meth)acrylic resin solution according to claim 2.

4. The (meth)acrylate having a cyclic ether group is at least one selected from the group consisting of (meth)acrylates having an epoxy group, (meth)acrylates having an alicyclic epoxy group, and (meth)acrylates having an oxetanyl group. A method for producing a (meth)acrylic resin solution according to claim 2.

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