Method for producing (METH)acrylic resin solution

Abstract

Disclosed is a method for producing a (meth)acrylic resin solution. The method for producing a (meth)acrylic resin solution includes a step in which one or more monomers including a (meth)acrylate compound are polymerized in a solvent having a cyclic ether group but not having a radically polymerizable group, thereby obtaining a (meth)acrylic resin solution.

Description

Method for producing (meth)acrylic resin solution

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

[0002] (Meth)acrylic resins are used in a variety of fields because they have excellent transparency as well as excellent properties such as oil resistance and weather resistance. In general, (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).

[0003] JP 2012-184364 A

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

[0005] The present disclosure includes the following items [1] to [5]. [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 radically polymerizable group to obtain a (meth)acrylic resin solution. [2] A method for producing a (meth)acrylic resin solution according to item [1], in which the (meth)acrylate compound contains a (meth)acrylate having a fluorine-containing organic group and a (meth)acrylate having a cyclic ether group. [3] A method for producing a (meth)acrylic resin solution according to item [2], in which the (meth)acrylate having a fluorine-containing organic group is a (meth)acrylate having a fluoroalkyl group. [4] A method for producing a (meth)acrylic resin solution according to item [2], in which the (meth)acrylate having a cyclic ether group is at least one selected from the group consisting of a (meth)acrylate having an epoxy group and a (meth)acrylate having an oxetanyl group. [5] The method for producing a (meth)acrylic resin solution according to [2], wherein the (meth)acrylate having a cyclic ether group is a (meth)acrylate having an alicyclic epoxy group.

[0006] The present 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 the present disclosure has the advantage that the (meth)acrylic resin solution can be directly used for compounding in a cationic polymerization reaction or an anionic polymerization reaction without performing an isolation procedure for the (meth)acrylic resin (without performing solvent removal or replacement).

[0007] Hereinafter, embodiments of the present disclosure will be described, but the present disclosure is not limited to the following embodiments.

[0008] In this specification, a numerical range indicated using "to" indicates a range that includes the numerical values ​​before and after "to" as the minimum and maximum values, respectively. In numerical ranges described in stages in this specification, the upper or lower limit of a certain numerical range may be replaced with the upper or lower limit of another numerical range. Furthermore, in a numerical range described in this specification, the upper or lower limit of that numerical range may be replaced with a value shown in the examples. Furthermore, individually described upper and lower limits can be arbitrarily combined. In a numerical range described as "A to B," the numerical values ​​A and B at both ends are included as the lower and upper limits, respectively, in the numerical range. In this specification, for example, the term "10 or more" means "10" and "a number greater than 10," and this also applies when the numerical values ​​are different. Furthermore, for example, the term "10 or less" means "10" and "a number less than 10," and this also applies when the numerical values ​​are different.

[0009] In this specification, a (meth)acrylate compound refers to a compound having one or more (meth)acryloyl groups, and a (meth)acrylic resin refers to a (co)polymer having at least a structural unit derived from a (meth)acrylate compound. A (meth)acryloyl group refers to an acryloyl group or a corresponding methacryloyl group. The same applies to other similar expressions such as (meth)acrylate. Furthermore, "A or B" may include either A or B, or may include both.

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

[0011] Unless otherwise specified, the materials exemplified below may be used alone or in combination of two or more. When a composition contains multiple substances corresponding to each component, the amount used or content of each component means the total amount of the multiple substances present in the composition, unless otherwise specified.

[0012] [Method for producing (meth)acrylic resin solution] In one embodiment, a method for producing a (meth)acrylic resin solution includes a step of polymerizing a monomer containing a (meth)acrylate compound in a solvent having a cyclic ether group and not having a radically polymerizable group to obtain a (meth)acrylic resin solution.

[0013] <Monomer> (Meth)acrylate Compound The (meth)acrylate compound is a compound having one or more (meth)acryloyl groups. The (meth)acrylate compound may not have a functional group that exhibits reactivity with a solvent having a cyclic ether group, as described below. Examples of such functional groups include an amino group, a carboxy group, and a thiol group. In other words, the (meth)acrylate compound may be a (meth)acrylate compound that does not have an amino group, a carboxy group, or a thiol group.

[0014] Examples of the (meth)acrylate compound include a monofunctional (meth)acrylate having one (meth)acryloyl group, a polyfunctional (meth)acrylate having two or more (meth)acryloyl groups, etc. The (meth)acrylate compound may contain a monofunctional (meth)acrylate.

[0015] Examples of monofunctional (meth)acrylates include those having an alkyl group, 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. alkyl (meth)acrylates having an aromatic group such as benzyl (meth)acrylate and phenoxyethyl (meth)acrylate; (meth)acrylates having an alicyclic group such as cyclohexyl (meth)acrylate, isobornyl (meth)acrylate and dicyclopentanyl (meth)acrylate; (meth)acrylates having an alicyclic epoxy group (for example, 3,4-epoxycyclohexylmethyl (meth)acrylate, etc.), alicyclic epoxy (meth)acrylates having an epoxy group such as (meth)acrylates having an epoxy group other than a group (for example, glycidyl (meth)acrylate, etc.); (meth)acrylates having an oxetanyl group such as (3-ethyloxetan-3-yl)methyl (meth)acrylate; (meth)acrylates having a nitrogen-containing oxygen heterocyclic group such as 4-(meth)acryloylmorpholine; alkoxypolyalkylene 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 of the fluorine-containing organic group (fluoroalkyl group)-containing (meth)acrylate include trifluoromethyl (meth)acrylate, 2,2,2-trifluoroethyl (meth)acrylate, 1,1,1,3,3,3-hexafluoro-2-propyl (meth)acrylate, perfluoroethylmethyl (meth)acrylate, perfluoropropylmethyl (meth)acrylate, perfluorobutylmethyl (meth)acrylate, perfluoropentylmethyl (meth)acrylate, perfluorohexylmethyl (meth)acrylate, perfluoroheptylmethyl (meth)acrylate, perfluorooctylmethyl (meth)acrylate, perfluorononylmethyl (meth)acrylate, perfluorodecylmethyl (meth)acrylate, perfluoroundecylmethyl (meth)acrylate, perfluorododecylmethyl (meth)acrylate, perfluorotridecylmethyl (meth)acrylate, and perfluorotetradecylmethyl (meth)acrylate.

[0016] The amount of the monofunctional (meth)acrylate used may be 60% by mass or more (60 to 100% by mass), 80% by mass or more (80 to 100% by mass), or 90% by mass or more (90 to 100% by mass), or may be 100% by mass, based on the total amount of the (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, and ethoxylated trimethylolpropane tri(meth)acrylate; ethoxylated bisphenol A di(meth)acrylate, propoxylated bisphenol A di(meth)acrylate, ethoxylated propane di(meth)acrylate, and ethoxylated propane di(meth)acrylate; and aromatic poly(meth)acrylates such as propoxylated 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 di(meth)acrylate, propoxylated fluorene di(meth)acrylate, and ethoxylated propoxylated fluorene di(meth)acrylate.

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

[0019] In one embodiment, the monomer may contain, 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 (e.g., a (meth)acrylate having an alicyclic epoxy group, a (meth)acrylate having an epoxy group other than an alicyclic epoxy group, etc.) and a (meth)acrylate having an oxetanyl group. The (meth)acrylate having a cyclic ether group may be, for example, a (meth)acrylate having an alicyclic epoxy group.

[0020] By polymerizing these monomers, it is possible to obtain 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. For example, when a (meth)acrylate having a fluorine-containing organic group is used as the (meth)acrylate compound in an adhesive composition containing a (meth)acrylate compound and an epoxy compound, the (meth)acrylic resin (X) acts as a crosslinking agent, making it possible to form a cured product of the adhesive composition having sufficient adhesive strength and high infrared transmittance.

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

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

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

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

[0025] <Solvent> The solvent is a solvent having a cyclic ether group but not having a radically polymerizable group. The cyclic ether group may be an epoxy group or an oxetanyl group. Examples of the solvent include those commonly used in the field of epoxy resin diluents. Examples of the solvent include epoxy resins that are liquid at 25°C. The solvent may be, for example, an aliphatic diglycidyl ether.

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

[0027] Examples of aliphatic diglycidyl ethers include diglycidyl ethers having an alkylene group, 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 an oxyalkylene group, such as diethylene glycol diglycidyl ether, tripropylene glycol diglycidyl ether, and polyethylene glycol diglycidyl ether; and diglycidyl ethers having a cycloalkylene group, such as hydrogenated bisphenol A diglycidyl ether, 1,4-cyclohexanedimethanol diglycidyl ether, and diglycidyl-1,2-cyclohexanedicarboxylate.

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

[0029] <Polymerization Reaction> The (meth)acrylic resin solution can be obtained, for example, by polymerizing a monomer by radical polymerization using a solution polymerization method. When polymerizing the monomer, a thermal radical generator, an additive, etc. may be added as necessary.

[0030] Examples of the thermal radical generator include organic peroxides such as cumene hydroperoxide, diisopropylbenzene hydroperoxide, di-t-butyl peroxide, lauroyl peroxide, benzoyl peroxide, t-butylperoxyisopropyl carbonate, t-amylperoxy-2-ethylhexanoate, and t-butylperoxy-2-ethylhexanoate; and azo compounds such as 2,2'-azobis(isobutyronitrile), 1,1'-azobis(cyclohexanecarbonitrile), 2,2'-azobis(2,4-dimethylvaleronitrile), and dimethyl-2,2'-azobis(2-methylpropionate).

[0031] The amount of the thermal radical generator to be added may be appropriately set depending on 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 the monomers.

[0032] Examples of the additives include chain transfer agents, antioxidants, light stabilizers, weather stabilizers, ultraviolet absorbers, radical scavengers, etc. The amount of the 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 the monomers.

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

[0034] <(Meth)acrylic Resin Solution> The solids concentration of the (meth)acrylic resin solution may be, for example, 10 to 80% by mass, 20% by mass or more, 30% by mass or more, or 40% by mass or more, and may be 70% by mass or less, 65% by mass or less, or 60% by mass or less. Here, the solids content of the (meth)acrylic resin solution refers to components other than the solvent of the (meth)acrylic resin solution.

[0035] The viscosity of the (meth)acrylic resin solution at 25°C may be, for example, 1 to 100 Pa s, and may be 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, applied 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 measured by gel permeation chromatography (GPC) using a calibration curve with standard polystyrene. The weight average molecular weight (Mw) can be measured, for example, by the method described in the Examples.

[0037] The obtained (meth)acrylic resin solution contains a solvent having a cyclic ether group, and therefore has the advantage that the obtained (meth)acrylic resin solution can be used as is for compounding in a cationic polymerization reaction, an anionic polymerization reaction, etc. without performing an isolation operation of the (meth)acrylic resin (without performing removal or substitution of the solvent).

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

[0039] [Synthesis of (meth)acrylic resin solution] The following raw materials 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 (registered trademark) 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(D): neopentyl glycol diglycidyl ether (Epogose (registered trademark) NPG(D)) (manufactured by Yokkaichi Synthetic Co., Ltd.) BisF: Bisphenol F epoxy resin (EPICLON (registered trademark) 830, manufactured by DIC Corporation, liquid at 25°C)

[0040] Example 1 84.06 g of M-3F and 98.12 g of TTA-15 (molar ratio of M-3F / TTA-15 = 50% / 50%), 10.17 g of V-601, and 23.72 g of NPG (D) were mixed to prepare a mixture (a-1). Separately, 1.82 g of V-601 was dissolved in 7.29 g of NPG (D) to prepare a solution (b-1).

[0041] A flask equipped with a stirrer, dropping funnel, condenser, thermometer, and gas inlet tube was charged with 163.2 g of NPG (D), and the mixture was stirred under a nitrogen atmosphere while replacing the gas, and the temperature was raised to 85°C. Next, mixture (a-1) was added dropwise to the flask over 2 hours. After the dropwise addition was completed, the mixture was stirred at 85°C for 20 minutes, and then solution (b-1) was added and stirred for an additional 7 hours. Next, the mixture was cooled to room temperature (25°C) while continuing to stir, and a (meth)acrylic resin solution of Example 1 was obtained. The solids concentration was 50% by mass.

[0042] Example 2 141.02 g of M-3F and 41.15 g of TTA-15 (molar ratio of M-3F / TTA-15 = 80% / 20%), 10.17 g of V-601, and 23.72 g of NPG (D) were mixed to prepare a mixture (a-2). A (meth)acrylic resin solution of Example 2 was obtained by the same procedure as in Example 1, except that the mixture (a-1) was replaced with the mixture (a-2). The solids concentration was 50% by mass.

[0043] Example 3 121.43 g of M-3F and 60.75 g of TTA-15 (molar ratio of M-3F / TTA-15=70% / 30%), 10.17 g of V-601, and 23.72 g of NPG (D) were mixed to prepare a mixture (a-3). A (meth)acrylic resin solution of Example 3 was obtained by the same procedure as in Example 1, except that the mixture (a-1) was replaced with the mixture (a-3). The solids concentration was 50% by mass.

[0044] Example 4 48.63 g of M-3F and 132.44 g of TTA-15 (molar ratio of M-3F / TTA-15=30% / 70%), 10.17 g of V-601, and 23.72 g of NPG (D) were mixed to prepare a mixture (a-4). A (meth)acrylic resin solution of Example 4 was obtained by the same procedure as in Example 1, except that the mixture (a-1) was replaced with the mixture (a-4). The solids concentration was 50% by mass.

[0045] Example 5 32.01 g of M-3F and 149.45 g of TTA-15 (molar ratio of M-3F / TTA-15 = 20% / 80%), 10.17 g of V-601, and 23.72 g of NPG (D) were mixed to prepare a mixture (a-5). A (meth)acrylic resin solution of Example 5 was obtained by the same procedure as in Example 1, except that the mixture (a-1) was replaced with the mixture (a-5). The solids concentration was 50% by mass.

[0046] Example 6 144.38 g of M-3F and 42.13 g of TTA-15 (molar ratio of M-3F / TTA-15=80% / 20%), 5.78 g of V-601, and 24.11 g of NPG (D) were mixed to prepare a mixture (a-6). Separately, 1.87 g of V-601 was dissolved in 7.46 g of NPG (D) to prepare a solution (b-2).

[0047] A flask equipped with a stirrer, dropping funnel, condenser, thermometer, and gas inlet tube was charged with 162.44 g of NPG (D), and the mixture was stirred under a nitrogen atmosphere while replacing the gas, and the temperature was raised to 85°C. Next, mixture (a-6) was added dropwise to the flask over 2 hours. After the dropwise addition was completed, the mixture was stirred at 85°C for 20 minutes, and then solution (b-2) was added and stirred for an additional 7 hours. Next, while continuing to stir, the mixture was cooled to room temperature (25°C) to obtain a (meth)acrylic resin solution of Example 6. The solids concentration was 50% by mass.

[0048] Example 7 182.17 g of M-3F (molar ratio of M-3F / TTA-15 = 100% / 0%), 10.17 g of V-601, and 23.72 g of NPG (D) were mixed to prepare a mixture (a-7). A (meth)acrylic resin solution of Example 7 was obtained by the same procedure as in Example 1, except that the mixture (a-1) was replaced with the mixture (a-7). The solid content concentration was 50% by mass.

[0049] Example 8 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%), 2.28 g of V-601, and 24.42 g of NPG (D) were mixed to prepare a mixture (a-8). A (meth)acrylic resin solution of Example 8 was obtained by the same procedure as in Example 6, except that the mixture (a-6) was replaced with the mixture (a-8). The solids concentration was 50% by mass.

[0050] Example 9 A (meth)acrylic resin solution of Example 9 was obtained in the same manner as in Example 8, except that the solvent was changed from NPG (D) to BisF. The solid content concentration was 50 mass%.

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

[0052] (Measurement of weight average molecular weight (Mw)) A (meth)acrylic resin solution was dissolved in tetrahydrofuran (THF) to prepare a 0.2 mass % THF solution as a sample for Mw measurement. Mw was measured by gel permeation chromatography (GPC) and calculated by conversion using a calibration curve of standard polystyrene. The GPC conditions are shown below. The results are also shown in Table 1. Measuring apparatus: Shodex (registered trademark) GPC-101 (manufactured by Resonac Co., Ltd.) Detector: Differential refractometer Shodex RI-71S (manufactured by Resonac Co., Ltd.) Column: Shodex LF-804 + LF-804 (manufactured by Resonac Co., Ltd.) Column temperature: 40°C Eluent: tetrahydrofuran (THF) Flow rate: 1 mL / min

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

[0054]

Claims

1. A method for producing a (meth)acrylic resin solution, comprising the step of polymerizing a monomer containing a (meth)acrylate compound in a solvent having a cyclic ether group and no radically polymerizable group to obtain a (meth)acrylic resin solution.

2. The method for producing a (meth)acrylic resin solution according to claim 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.

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

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

5. The method for producing a (meth)acrylic resin solution according to claim 2, wherein the (meth)acrylate having a cyclic ether group is a (meth)acrylate having an alicyclic epoxy group.

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