WO2025018399A1 - Method for producing (meth)acrylic resin solution - Google Patents

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

This disclosure relates to a method for producing a (meth)acrylic resin solution.

(Meth)acrylic resins are used in a variety of fields because they have excellent transparency and, for example, excellent oil resistance and weather resistance. In general, (meth)acrylic resins are produced by polymerizing (meth)acrylate compounds in a hydrocarbon solvent such as xylene or toluene (for example, Patent Document 1).

JP 2012-184364 A

The purpose of this disclosure is to provide a novel method for producing a (meth)acrylic resin solution.

The present disclosure includes the following [1] to [5].
[1] The method includes a step of polymerizing a monomer including a (meth)acrylate compound in a solvent having a cyclic ether group and not having a radical polymerizable group to obtain a (meth)acrylic resin solution.
A method for producing a (meth)acrylic resin solution.
[2] The (meth)acrylate compound contains a (meth)acrylate having a fluorine-containing organic group and a (meth)acrylate having a cyclic ether group,
A method for producing the (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 according to [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 and (meth)acrylates having an oxetanyl group.
[2] A method for producing the (meth)acrylic resin solution according to [2].
[5] The (meth)acrylate having a cyclic ether group is a (meth)acrylate having an alicyclic epoxy group.
[2] A method for producing the (meth)acrylic resin solution according to [2].

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 used as is for compounding in a cationic polymerization reaction or an anionic polymerization reaction without performing an isolation operation of the (meth)acrylic resin (without removing or replacing the solvent).

The following describes embodiments of the present disclosure. However, the present disclosure is not limited to the following embodiments.

In this specification, a numerical range indicated using "~" indicates a range that includes the numerical values before and after "~" as the minimum and maximum values, respectively. In a numerical range 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 a numerical range of another stage. In addition, in a numerical range described in this specification, the upper or lower limit of the numerical range may be replaced with a value shown in an example. In addition, the upper and lower limits described individually can be arbitrarily combined. In a numerical range "A~B", the numerical values 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 "a numerical value exceeding 10", and this also applies when the numerical values are different. In addition, for example, the description "10 or less" means "10" and "a numerical value less than 10", and this also applies when the numerical values are different.

In this specification, a (meth)acrylate compound means a compound having one or more (meth)acryloyl groups, and a (meth)acrylic resin means a (co)polymer having at least a structural unit derived from a (meth)acrylate compound. A (meth)acryloyl group means an acryloyl group or the corresponding methacryloyl group. The same applies to other similar expressions such as (meth)acrylate. In addition, "A or B" means that either A or B is included, and it may also include both.

In this specification, a 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. 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- or four-membered cyclic ether. Examples of such cyclic ether groups include an epoxy group (oxiranyl group) and an oxetanyl group. Epoxy groups include alicyclic epoxy groups (epoxy groups formed together with the two carbon atoms that constitute an alicyclic ring) such as an epoxycyclohexyl group.

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

[Method of producing (meth)acrylic resin solution]
A method for producing a (meth)acrylic resin solution in one embodiment includes 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.

<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 shows reactivity to a solvent having a cyclic ether group, which will be described later. Examples of such functional groups include an amino group, a carboxy group, and a thiol group. That is, the (meth)acrylate compound may be a (meth)acrylate compound that does not have an amino group, a carboxy group, or a thiol group.

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 contain a monofunctional (meth)acrylate.

Examples of monofunctional (meth)acrylates include alkyl (meth)acrylates 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; (meth)acrylates having an aromatic group such as benzyl (meth)acrylate and phenoxyethyl (meth)acrylate; cyclohexyl (meth)acrylate, isobornyl (meth)acrylate, and diphenyl ether (meth)acrylate. (Meth)acrylates having an alicyclic group such as cyclopentanyl (meth)acrylate; (meth)acrylates having an alicyclic epoxy group (e.g., 3,4-epoxycyclohexylmethyl (meth)acrylate, etc.), (meth)acrylates having an epoxy group other than an alicyclic epoxy group (e.g., 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; methoxyethylene glycol (meth)acrylate, methoxytetraethylene glycol (meth)acrylate, methoxy Alkoxy polyalkylene glycol (meth)acrylates such as hexaethylene 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; 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, Examples of (meth)acrylates include perfluoromethyl (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.

The amount of 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) based on the total amount of (meth)acrylate compounds, or may be 100% by mass.

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 type di(meth)acrylate, propoxylated bisphenol A type di(meth)acrylate, ethoxylated propane di(meth)acrylate, and the like; Examples of the aromatic poly(meth)acrylate include propyloxylated 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.

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.

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 (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.

By polymerizing these monomers, a (meth)acrylic resin (X) can be obtained that has 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 applied as a (meth)acrylate compound to 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 that has sufficient adhesive strength and high infrared transmittance.

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).

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) based on the total amount of monomers, or may be 100% by mass.

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.

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) based on the total amount of monomers, or may be 0% by mass.

<Solvent>
The solvent is a solvent having a cyclic ether group and not having a radical polymerizable group. The cyclic ether group may be an epoxy group or an oxetanyl group. The solvent may be, for example, a solvent generally used in the field of epoxy resin diluents. The solvent may also be, for example, an epoxy resin that is liquid at 25°C. The solvent may be, for example, an aliphatic diglycidyl ether.

In this specification, a radically polymerizable group refers to a group having a carbon-carbon double bond. Examples of radically polymerizable groups include (meth)acryloyl groups, vinyl groups, allyl groups, styryl groups, alkenyl groups, alkenylene groups, and maleimide groups.

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.

The amount of solvent used can be set appropriately depending on the type of monomer, reaction conditions, the percentage of solids in the (meth)acrylic resin solution, etc.

<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.

Examples of thermal radical generators include organic peroxides such as cumene hydroperoxide, diisopropylbenzene hydroperoxide, di-t-butyl peroxide, lauroyl peroxide, benzoyl peroxide, t-butylperoxyisopropylcarbonate, 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).

The amount of thermal radical generator added may be set appropriately 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 monomer.

Additives include chain transfer agents, antioxidants, light stabilizers, weather stabilizers, ultraviolet 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.

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.

<(Meth)acrylic resin solution>
The solid content 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 70% by mass or less, 65% by mass or less, or 60% by mass or less. Here, the solid content of the (meth)acrylic resin solution means components other than the solvent of the (meth)acrylic resin solution.

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, applicable cone-plate rotor: 3°×R17.65).

The weight average molecular weight (Mw) of the (meth)acrylic resin may be, for example, 1,000 to 200,000, or may be 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 obtained by using a calibration curve of standard polystyrene in gel permeation chromatography (GPC). The weight average molecular weight (Mw) can be measured, for example, by the method described in the Examples.

The resulting (meth)acrylic resin solution contains a solvent having a cyclic ether group. Therefore, the resulting (meth)acrylic resin solution has the advantage that it can be used as is for compounding in cationic polymerization reactions, anionic polymerization reactions, etc. without the need to isolate the (meth)acrylic resin (without removing or replacing the solvent).

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

[Synthesis of (meth)acrylic resin solution]
The following raw materials were prepared:
(Meth)acrylate compound 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 Chemical Co., Ltd.)
BisF: Bisphenol F type epoxy resin (EPICLON (registered trademark) 830, manufactured by DIC Corporation, liquid at 25°C)

Example 1
Mixture (a-1) 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%), 10.17 g of V-601, and 23.72 g of NPG (D). Separately, solution (b-1) was prepared by dissolving 1.82 g of V-601 in 7.29 g of NPG (D).

In a flask equipped with a stirrer, dropping funnel, condenser, thermometer, and gas inlet tube, 163.2 g of NPG (D) was charged and stirred while replacing the gas under a nitrogen atmosphere, and the temperature was raised to 85°C. Next, mixture (a-1) was dropped into the flask over 2 hours. After the dropping was completed, the mixture was stirred at 85°C for 20 minutes, after which solution (b-1) 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 the (meth)acrylic resin solution of Example 1. The solid content was 50% by mass.

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 changed to the mixture (a-2). The solid content concentration was 50% by mass.

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 changed to the mixture (a-3). The solid content concentration was 50% by mass.

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 changed to the mixture (a-4). The solid content concentration was 50% by mass.

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 changed to the mixture (a-5). The solid content concentration was 50% by mass.

Example 6
Mixture (a-6) 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%), 5.78 g of V-601, and 24.11 g of NPG (D). Separately, solution (b-2) was prepared by dissolving 1.87 g of V-601 in 7.46 g of NPG (D).

In a flask equipped with a stirrer, dropping funnel, condenser, thermometer, and gas inlet tube, 162.44 g of NPG (D) was charged and stirred while replacing the gas in a nitrogen atmosphere, and the temperature was raised to 85°C. Next, mixture (a-6) was dropped into the flask over 2 hours. After the dropping was completed, the mixture was stirred at 85°C for 20 minutes, after which 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 the (meth)acrylic resin solution of Example 6. The solid content was 50% by mass.

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 changed to the mixture (a-7). The solid content concentration was 50% by mass.

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 changed to the mixture (a-8). The solid content concentration was 50% by mass.

<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% by mass.

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

(Measurement of weight average molecular weight (Mw))
As a sample for Mw measurement, a (meth)acrylic resin solution was dissolved in tetrahydrofuran (THF) to prepare a 0.2 mass% THF solution. Mw was measured by gel permeation chromatography (GPC) and calculated using a calibration curve of standard polystyrene. The GPC conditions are shown below. The results are shown in Table 1.
Measuring device: Showdex (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

(Observation of resin solution)
The (meth)acrylic resin solutions were visually observed, and transparent ones were rated as "A", and opaque ones were rated as "B". The results are shown in Table 1.

Claims (5)

The method includes a step of polymerizing a monomer including a (meth)acrylate compound in a solvent having a cyclic ether group and not having a radical polymerizable group to obtain a (meth)acrylic resin solution.
A method for producing a (meth)acrylic resin solution. The (meth)acrylate compound contains a (meth)acrylate having a fluorine-containing organic group and a (meth)acrylate having a cyclic ether group.
A method for producing the (meth)acrylic resin solution according to claim 1. The (meth)acrylate having a fluorine-containing organic group is a (meth)acrylate having a fluoroalkyl group.
A method for producing the (meth)acrylic resin solution according to claim 2. 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.
A method for producing the (meth)acrylic resin solution according to claim 2. The (meth)acrylate having a cyclic ether group is a (meth)acrylate having an alicyclic epoxy group.
A method for producing the (meth)acrylic resin solution according to claim 2.