Resin composition, cured resin product, and method for producing cured resin product

Abstract

The resin composition contains compound (A) having a (meth)acryloyl group, compound (B) having an epoxy group and / or an oxetanyl group, radical polymerization initiator (C) and cationic polymerization initiator (D). The hydrogen bonding substituent value of one of compound (A) and compound (B) is 0.0001-0.1111 mol / g inclusive, and the hydrogen bonding substituent value of the other to the hydrogen bonding substituent value of the one is 2 / 3 or less. In a cured product of the resin composition, two or more peaks of loss factor tanδ are observed, the peaks including a first peak having the peak top position at a temperature of lower than 100°C and a second peak having the peak top position at a temperature of 100°C or higher, and the minimum value of loss factor tanδ at 100°C or lower is 0.1 or less.

Description

Technical Field

[0001] The present invention relates to a resin composition, a cured resin product, and a method for producing a cured resin product. More specifically, the present invention relates to a resin composition, a cured resin product which is a cured product of the resin composition, and a method for producing the cured resin product.

Background Art

[0002] Plastic substrates are used as substrates for flexible displays, and mechanical properties such as bending strength, dimensional accuracy due to temperature and humidity changes, and processing suitability such as plating solution resistance and solder heat resistance during wiring pattern formation are required.

[0003] To achieve these requirements, many resin materials have been proposed. For example, various (meth)acrylate resins having an alicyclic structure with excellent heat resistance are disclosed among molded products obtained by photocuring a photopolymerizable composition (see, for example, Patent Document 1).

[0004] In addition, a photosensitive prepolymer containing an epoxy resin with excellent heat resistance is disclosed (see, for example, Patent Document 2).

[0005] In addition, an ultraviolet curable resin composition containing an acrylate resin composition that undergoes photoradical polymerization and an epoxy resin composition that undergoes photocationic polymerization is disclosed (see, for example, Patent Document 3).

Prior Art Documents

Patent Documents

[0006]

Patent Document 1

Patent Document 2

Patent Document 3

Summary of the Invention

Problems to be Solved by the Invention

[0007] However, these disclosed technologies cannot be said to meet the required characteristics, and in particular, it is difficult to meet both the required characteristics of bending strength and heat resistance.

[0008] The present invention provides a resin composition for obtaining a resin cured product with excellent bending strength and heat resistance, a resin cured product obtained by curing the resin composition, and a method for producing the resin cured product. [Means for solving the problem]

[0009] The present invention [1] is a resin composition comprising a compound (A) having a (meth)acryloyl group, a compound (B) having an epoxy group and / or an oxetanyl group, a radical polymerization initiator (C), and a cationic polymerization initiator (D), wherein the hydrogen bonding substituent value of either compound (A) or compound (B) is 0.0001 mol / g or more and 0.1111 mol / g or less, the hydrogen bonding substituent value of the other to the hydrogen bonding substituent value of the other is 2 / 3 or less, the cured product of the resin composition has 2 or more peaks of the loss coefficient tanδ, the peaks include a first peak whose peak top position is less than 100°C and a second peak whose peak top position is 100°C or higher, and the minimum value of the loss coefficient tanδ at 100°C or less is 0.1 or less.

[0010] The present invention [2] includes the resin composition described in [1] above, wherein one of the radical polymerization initiator (C) and the cationic polymerization initiator (D) is a photopolymerization initiator and the other is a thermal polymerization initiator.

[0011] The present invention [3] comprises the resin composition described in [1] or [2] above, wherein compound (A) is urethane (meth)acrylate.

[0012] The present invention [4] includes a resin cured product which is a cured product of the resin composition described in any one of the above [1] to [3].

[0013] The present invention [5] is a method for producing a resin cured product as described in [4] above, wherein in the resin composition, the radical polymerization initiator (C) and the cationic polymerization initiator (D) are both photopolymerization initiators, the absolute value of the difference between the peak top position on the longer wavelength side of the light absorption wavelength of the radical polymerization initiator (C) and the peak top position on the longer wavelength side of the light absorption wavelength of the cationic polymerization initiator (D) is 30 nm or more, and the method includes irradiating with light having a wavelength corresponding to the relatively longer wavelength side of the peak top position of the radical polymerization initiator (C) and the peak top position of the cationic polymerization initiator (D), followed by irradiating with light having a wavelength corresponding to the relatively shorter wavelength side of the peak top position. [Effects of the Invention]

[0014] According to the resin composition of the present invention, it is possible to manufacture resin cured products with excellent bending strength and heat resistance. More specifically, because the resin composition of the present invention enables the manufacture of resin cured products with excellent bending strength and heat resistance, it is possible to easily manufacture resin cured products that satisfy dimensional accuracy under temperature and humidity changes, as well as processing suitability such as resistance to plating solutions and solder heat resistance during wiring pattern formation.

[0015] In other words, in the resin composition of the present invention, the hydrogen bonding substituent value of either compound (A) having a (meth)acryloyl group or compound (B) having an epoxy group and / or an oxetanyl group is 0.0001 mol / g or more and 0.1111 mol / g or less, and the hydrogen bonding substituent value of the other is 2 / 3 or less to the hydrogen bonding substituent value of the other. As a result, compound (A) and compound (B) are poorly miscible with each other and undergo phase separation. A cured product of the resin composition is obtained by curing in a phase-separated state. In such a cured product of the resin composition, there are two or more peaks of the loss coefficient tanδ derived from compound (A) and compound (B), with the peak top position of one of these peaks being a first peak at a temperature below 100°C and the peak top position of the other peak being a second peak at a temperature of 100°C or higher. Furthermore, the minimum value of the loss coefficient tanδ at 100°C or less is 0.1 or less. The compounds originating from the first peak form the soft segment, and those originating from the second peak form the hard segment, thus achieving both heat resistance and flexibility. Furthermore, since the minimum value of the loss coefficient tanδ below 100°C is 0.1 or less, it exhibits a high recovery rate from deformation.

[0016] The cured resin product of the present invention is a cured product of the resin composition of the present invention. Therefore, it has excellent flexural strength and heat resistance. For this reason, the cured resin product is effective as a substrate for liquid crystal displays and organic EL displays, and is particularly effective as a substrate for foldable displays.

[0017] In the method for producing a cured resin of the present invention, both the radical polymerization initiator (C) and the cationic polymerization initiator (D) are photoinitiators. The absolute value of the difference between the peak top position on the long wavelength side of the light absorption wavelength of the radical polymerization initiator (C) and the peak top position on the long wavelength side of the light absorption wavelength of the cationic polymerization initiator (D) is 30 nm or more. After irradiating with light having a wavelength corresponding to the relatively long wavelength side peak top position among the peak top position of the radical polymerization initiator (C) and the peak top position of the cationic polymerization initiator (D), light having a wavelength corresponding to the relatively short wavelength side peak top position is irradiated. Therefore, a cured resin excellent in flexural strength and heat resistance can be produced.

Brief Description of the Drawings

[0018] [Figure 1] FIG. 1 is a transmission electron micrograph of the resin composition obtained in Example 1, showing that it has a phase separation structure.

Modes for Carrying Out the Invention

[0019] 1. Resin Composition The resin composition of the present invention contains a compound (A) having a (meth)acryloyl group, a compound (B) having an epoxy group and / or an oxetanyl group, a radical polymerization initiator (C), and a cationic polymerization initiator (D).

[0020] The following substances are described by way of example. That is, each substance is not limited to the following examples. Any substance that exhibits the actions and effects of the present invention can be used as a raw material for the resin composition.

[0021] 2. Compound (A) Having a (Meth)acryloyl Group Compound (A) is not particularly limited as long as it has a (meth)acryloyl group and does not have an epoxy group and an oxetanyl group. Examples of the compound having a (meth)acryloyl group include 2-ethylhexyl (meth)acrylate, n-butyl (meth)acrylate, i-butyl (meth)acrylate, t-butyl (meth)acrylate, lauryl (meth)acrylate, alkyl (meth)acrylate, methoxyethyl (meth)acrylate, 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 2-hydroxybutyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate, benzyl (meth)acrylate, phenyl (meth)acrylate, ethylene glycol di(meth)acrylate, diethylene glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, hydroxyethyl (meth)acrylate, 1,3-butylene glycol di(meth)acrylate, 1,4-butylene glycol di(meth)acrylate, neopentyl glycol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, dicyclopentanyl (meth)acrylate, dicyclopentenyl oxyethyl (meth)acrylate, norbornene (meth)acrylate, phenoxyethyl (meth)acrylate (PO), phenoxy polyethylene glycol (meth)acrylate, 2-hydroxy-3-phenoxypropyl (meth)acrylate, cyclohexyl (meth)acrylate (CH), nonylphenol EO adduct (meth)acrylate, methoxy triethylene glycol (meth)acrylate and tetrahydrofurfuryl (meth)acrylate, polyisoprene (meth)acrylate oligomer, polybutadiene (meth)acrylate oligomer and polyurethane (meth)acrylate oligomer (urethane (meth)acrylate), and contains one or more (meth)acrylate oligomers selected from the group consisting of (meth)acrylic copolymers having a (meth)acryloyl group. More preferably, polyurethane (meth)acrylate oligomer and (meth)acrylic copolymer having a (meth)acryloyl group can be mentioned.

[0022] Polyurethane (meth)acrylate oligomers can be synthesized using various commercially available products or by reacting a compound having an isocyanate group with a (meth)acrylate having an active hydrogen group to form a urethane. Examples of commercially available products include Kyoeisha Chemical's AH-600; Phenylglycidyl ether acrylate hexamethylene diisocyanate urethane prepolymer; UA-306H; Pentaerythritol triacrylate hexamethylene diisocyanate urethane prepolymer; UA-306T; Pentaerythritol triacrylate toluene diisocyanate urethane prepolymer; UA-306I; Pentaerythritol triacrylate isophorone diisocyanate urethane prepolymer; and UA-510H; Dipentaerythritol pentaacrylate hexamethylene diisocyanate. Urethane prepolymers such as UF-8001G; non-yellowing type oligourethane acrylate (high hardness, medium elongation), DAUA-167; and carboxylic acid-containing urethane acrylate oligomers such as UV-1700B, UV-6300B, UV-7550B, UV-7600B, UV-7605B, UV-7610B, UV-7620EA, UV-7630B, UV-7640B, UV-7650B, etc., manufactured by Mitsubishi Chemical Corporation can be used.

[0023] When synthesizing urethane acrylates, compounds having isocyanate groups that can be used in the synthesis include, for example, ethylene diisocyanate, trimethylene diisocyanate, tetramethylene diisocyanate, pentamethylene diisocyanate, hexamethylene diisocyanate, octamethylene diisocyanate, nonamethylene diisocyanate, 2,2'-dimethylpentane diisocyanate, 2,2,4-trimethylhexane diisocyanate, decamethylene diisocyanate, butene diisocyanate, and 1,3-butadiene-1. 4-Diisocyanate, 2,4,4-Trimethylhexamethylene diisocyanate, 1,6,11-Undecamethylene triisocyanate, 1,3,6-Hexamethylene triisocyanate, 1,8-Diisocyanate-4-Isocyanatomethyloctane, 2,5,7-Trimethyl-1,8-Diisocyanate-5-Isocyanatomethyloctane, Bis(isocyanatoethyl)carbonate, Bis(isocyanatoethyl)ether, 1,4-Butylene glycol dipropyl ether-ω,ω'-Diisocyanate, Lysine isocyanatomethyl Luester, lysine triisocyanate, 2-isocyanatoethyl-2,6-diisocyanate hexanoate, 2-isocyanatopropyl-2,6-diisocyanate hexanoate, bis(4-isocyanate-n-butylidene)pentaerythritol, 2,6-diisocyanate methyl caproate, isophorone diisocyanate, dicyclohexylmethane diisocyanate, 1,3-bis(isocyanatomethyl)cyclohexane, 1,4-bis(isocyanatomethyl)cyclohexane, 1,3-cyclohexane diisocyanate, 1,4-Cyclohexane diisocyanate, 1,3-Bis(isocyanatoethyl)cyclohexane, 1,4-Bis(isocyanatoethyl)cyclohexane, Methylcyclohexane diisocyanate, 2,2'-Dimethyldicyclohexylmethane diisocyanate, Dimer acid diisocyanate, 2,5-Diisocyanatomethylbicyclo[2,2,1]-heptane, 2,6-Diisocyanatomethylbicyclo[2,2,1]-heptane, 2-Isocyanatomethyl 2-(3-Isocyanatopropyl)-5-Isocyanatomethylbicyclo-[2,2,1)-Heptane, 2-Isocyanatomethyl-2-(3-Isocyanatopropyl)-6-Isocyanatomethylbicyclo-[2,2,1]-Heptane, 2-Isocyanatomethyl3-(3-Isocyanatopropyl)-5-(2-Isocyanatoethyl)-Bicyclo-[2,2,1]-Heptane, 2-Isocyanatomethyl3-(3-Isocyanatopropyl)-6-(2-Isocyanatoethyl)-Bicyclo-[2,2,1]-Heptane, 2-Isocyanatomethyl2-(3-Isocyanatopropyl Examples include polyisocyanate monomers (Pyr)-5-(2-isocyanatoethyl)-bicyclo-[2,2,1]-heptane, 2-isocyanatomethyl2-(3-isocyanatopropyl)-6-(2-isocyanatoethyl)-bicyclo-[2,2,1]-heptane, tolylene diisocyanate, diphenylmethane diisocyanate, toluidine diisocyanate, paraphenylenediisocyanate, naphthalene diisocyanate, xylylene diisocyanate, and tetramethylxylylene diisocyanate. These polyisocyanate monomers can be used individually or in combination of two or more types.

[0024] Examples of polyisocyanate derivatives include modified products obtained by modifying the above-mentioned polyisocyanate monomers using known methods. More specifically, examples of polyisocyanate derivatives include polymers, isocyanurate modified products, allophanate modified products, polyol modified products, biuret modified products, urea modified products, oxadiazinetrione modified products, and carbodiimide modified products. Polymethylene polyphenylene polyisocyanate is also an example of a polyisocyanate derivative.

[0025] These polyisocyanate derivatives can be used individually or in combination of two or more types.

[0026] These polyisocyanate components can be used individually or in combination of two or more types.

[0027] These isocyanates can also be synthesized by reacting a compound having an active hydrogen group with a compound having two or more isocyanate groups, such that at least one isocyanate group remains.

[0028] Active hydrogen groups are groups capable of forming hydrogen bonds, such as hydroxyl groups, mercapto groups, and amino groups.

[0029] Examples of compounds having hydroxyl groups include ethylene glycol, trimethylpyrrole, polyether polyols, polyester polyols, polycarbonate polyols, polyurethane polyols, epoxy polyols, vegetable oil polyols, polyolefin polyols, acrylic polyols, and vinyl monomer-modified polyols.

[0030] Examples of compounds having a mercapto group include aliphatic mercaptan compounds such as 1,2,6,10,11-pentamercapto-4,8-dithiaundecane and 1,2,9,10-tetramercapto-6-mercaptomethyl-4,7-dithiadecane, aromatic mercaptan compounds such as thiophenol and mercaptotoluene, and examples of bifunctional or more polythiol compounds include aliphatic polythiol compounds such as 1,1-methanedithiol, 1,2-ethanedithiol, 1,1-propanedithiol, and 1,2-propanedithiol, and 1,2-dimercapto Aromatic polythiols such as tobenzene, 1,3-dimercaptobenzene, 1,4-dimercaptobenzene, 1,2-bis(mercaptomethyl)benzene, 1,3-bis(mercaptomethyl)benzene, 1,2-bis(mercaptoethylthio)benzene, 1,3-bis(mercaptoethylthio)benzene, 1,4-bis(mercaptoethylthio)benzene, etc., and aromatic polythiol compounds containing sulfur atoms in addition to mercapto groups, such as nuclear alkylates thereof, bis(mercaptomethyl) sulfide, bis(mercaptoethyl) sulfide, bis Aliphatic polythiol compounds containing a sulfur atom in addition to the mercapto group, such as (mercaptopropyl) sulfide and bis(mercaptomethylthio)methane, and esters of these of thioglycolic acid and mercaptopropionic acid, such as hydroxymethyl sulfide bis(2-mercaptoacetate), hydroxymethyl sulfide bis(3-mercaptopropionate), hydroxyethyl sulfide bis(2-mercaptoacetate), and hydroxyethyl sulfide bis(3-mercaptopropionate), which contain a sulfur atom in addition to the mercapto group. Aliphatic polythiol compounds containing ester bonds, heterocyclic compounds containing sulfur atoms in addition to mercapto groups such as 3,4-thiophene dithiol and 2,5-dimercapto-1,3,4-thiadiazole, compounds containing hydroxyl groups in addition to mercapto groups such as 2-mercaptoethanol, 3-mercapto-1,2-propanediol, glycerin di(mercaptoacetate), 1-hydroxy-4-mercaptocyclohexane, and 2,4-dimercaptophenol, 1,1,3,3-tetrakis(mercaptomethylthio)propane, 1,1,2,Examples include 2-tetrakis(mercaptomethylthio)ethane, 4,6-bis(mercaptomethylthio)-1,3-dithiacyclohexane, and compounds having a dithioacetal or dithioketal skeleton such as their oligomers; tris(mercaptomethylthio)methane, tris(mercaptoethylthio)methane, 1,1,5,5-tetrakis(mercaptomethylthio)-2,4-dithiapentane, and compounds having an orthocarboxylic acid trithioester skeleton such as their oligomers; 3,3'-di(mercaptomethylthio)-1,5-dimercapto-2,4-dithiapentane, 2,2'-di(mercaptomethylthio)-1,3-dithiacyclopentane, and compounds having an orthocarbonate tetrathioester skeleton such as their oligomers.

[0031] Examples of compounds containing an amino group include ethylenediamine, 1,3-propanediamine, 1,3-butanediamine, 1,4-butanediamine, 1,6-hexamethylenediamine, 1,4-cyclohexanediamine, 3-aminomethyl-3,5,5-trimethylcyclohexylamine (isophoronediamine), 4,4'-dicyclohexylmethanediamine, 2,5-bis(aminomethyl)bicyclo[2.2.1]heptane, 2,6-bis(aminomethyl)bicyclo[2.2.1]heptane, 1,3-bis(aminomethyl)cyclohexane, 1,4-bis(aminomethyl)cyclohexane, hydrazine, and tolylenediamine, triethylenetetramine, and tetraethylenepentamine.

[0032] The isocyanate-terminated prepolymer is obtained by reacting the above-mentioned polyisocyanate component and the above-mentioned compound having an active hydrogen group using a known method. Specifically, in this method, the polyisocyanate component and the compound having an active hydrogen group are mixed in a predetermined ratio and subjected to a urethane reaction.

[0033] In the urethane reaction, the equivalent ratio of isocyanate groups in the polyisocyanate component to active hydrogen groups (isocyanate groups / active hydrogen groups) is, for example, greater than 1, preferably 1.1 or more, more preferably 3 or more, even more preferably 6 or more, preferably 20, more preferably 15 or less, and even more preferably 10 or less.

[0034] In the urethane formation reaction, known polymerization methods are employed. Examples of polymerization methods include bulk polymerization and solution polymerization. In bulk polymerization, for example, the above components are mixed under a nitrogen atmosphere and reacted at a reaction temperature of 75-85°C for about 1-20 hours. In solution polymerization, for example, the above components are added to a known organic solvent under a nitrogen atmosphere and reacted at a reaction temperature of 20-80°C for about 1-20 hours.

[0035] Furthermore, during the polymerization reaction, a known urethane catalyst is added as needed. Also, if necessary, unreacted polyisocyanate is removed by a known method. This yields an isocyanate-terminated prepolymer.

[0036] The average number of functional groups of the isocyanate groups in the isocyanate-terminated prepolymer is, for example, 1.5 or more, preferably 2.0 or more. Alternatively, the average number of functional groups of the isocyanate groups in the isocyanate-terminated prepolymer is, for example, 3.0 or less, preferably 2.5 or less.

[0037] Furthermore, the above reaction yields a composition (hereinafter referred to as the crude prepolymer product) containing an isocyanate-terminated prepolymer and unreacted polyisocyanate components.

[0038] The isocyanate group concentration of the crude prepolymer product is, for example, 0.3% by mass or more, preferably 0.5% by mass or more, and more preferably 1.0% by mass or more, based on the total amount of the crude prepolymer product (on a solid content basis). Furthermore, the isocyanate group concentration of the crude prepolymer product is, for example, 15% by mass or less, preferably 12% by mass or less, and more preferably 10% by mass or less.

[0039] The crude prepolymer product is preferably purified by distillation. Distillation improves the mechanical strength and dimensional stability of the cured resin product (described later).

[0040] The distillation method is not particularly limited, but examples include batch distillation and continuous distillation. An example of a continuous distillation method is thin-film distillation (Smith thin-film distillation). Preferably, the distillation method is thin-film distillation (Smith thin-film distillation).

[0041] The distillation conditions are set according to the purpose and application. The distillation temperature is, for example, 120°C or higher, preferably 150°C or higher. Alternatively, the distillation temperature is, for example, 250°C or lower, preferably 200°C or lower. The distillation pressure (absolute pressure) is, for example, 1 Pa or higher, preferably 10 Pa or higher, more preferably 50 Pa or higher. Alternatively, the distillation pressure is, for example, 300 Pa or lower, preferably 200 Pa or lower, more preferably 100 Pa or lower.

[0042] The feed rate of the crude prepolymer product is, for example, 0.1 g / min or more, preferably 1.0 g / min or more, and more preferably 2.0 g / min or more. Alternatively, the feed rate of the crude prepolymer product is, for example, 100 g / min or less, preferably 50 g / min or less, and more preferably 10 g / min or less.

[0043] This removes unreacted polyisocyanate components from the crude prepolymer product, yielding a purified isocyanate-terminated prepolymer (hereinafter referred to as the purified prepolymer).

[0044] The purified prepolymer consists of an isocyanate-terminated prepolymer, or an isocyanate-terminated prepolymer and a trace amount (less than 10,000 ppm) of unreacted polyisocyanate component.

[0045] In the purified prepolymer, the content of isocyanate group-terminated prepolymers is, for example, 99.5% by mass or more, preferably 99.9% by mass or more, and for example, 100% by mass or less, based on the total amount of the purified prepolymer.

[0046] Furthermore, if unreacted polyisocyanate components are present, their content is, for example, 0.0001% by mass or more, preferably 0.0005% by mass or more, relative to the total amount (solid content) of the purified prepolymer. Also, the content of unreacted polyisocyanate components is, for example, 0.020% by mass or less, preferably 0.013% by mass or less, and more preferably 0.010% by mass or less, relative to the total amount (solid content) of the purified prepolymer.

[0047] Then, a radical-curable polyurethane resin is obtained by the reaction of the above-mentioned isocyanate-terminated prepolymer (preferably a purified prepolymer) with a compound having a hydroxyl-containing (meth)acroyl group.

[0048] Compounds containing a hydroxyl group (meth)acroyl group are compounds having one or more (meth)acroyl groups and one or more hydroxyl groups. (Meth)acryloyl refers to acryloyl and / or methacryloyl. (Meth)acrylic refers to acrylic and / or methacrylic. (Meth)acrylate refers to acrylate and / or methacrylate.

[0049] Examples of compounds containing a (meth)acryloyl group and a hydroxyl group include hydroxyl group-containing (meth)acrylates.

[0050] Examples of hydroxyl group-containing (meth)acrylates include monohydroxyl mono(meth)acrylate, polyhydroxyl mono(meth)acrylate, monohydroxyl poly(meth)acrylate, and polyhydroxyl poly(meth)acrylate.

[0051] Monohydroxyl mono(meth)acrylates are compounds that have one hydroxyl group and one (meth)acryloyl group in one molecule. Examples of monohydroxyl mono(meth)acrylates include 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate, 2-hydroxybutyl (meth)acrylate, 2-phenoxypropyl (meth)acrylate, 4-hydroxycyclohexyl (meth)acrylate, 3-chloro-2-hydroxypropyl (meth)acrylate, 2-hydroxy-3-phenyloxypropyl (meth)acrylate, 2-(meth)acryloyloxyethyl-2-hydroxyethyl phthalate, 2-hydroxyalkyl (meth)acryloyl phosphate, pentanediol mono(meth)acrylate, neopentyl glycol mono(meth)acrylate, polyethylene glycol mono(meth)acrylate, and polypropylene glycol mono(meth)acrylate.

[0052] Polyhydroxyl mono(meth)acrylates are compounds that have multiple hydroxyl groups and one (meth)acryloyl group in a single molecule. Examples of polyhydroxyl mono(meth)acrylates include trimethylolpropane mono(meth)acrylate, glycerin mono(meth)acrylate, and pentaerythritol mono(meth)acrylate.

[0053] Monohydroxyl poly(meth)acrylates are compounds that have one hydroxyl group and multiple (meth)acryloyl groups in one molecule. Examples of monohydroxyl poly(meth)acrylates include trimethylolpropane di(meth)acrylate, glycerin di(meth)acrylate, pentaerythritol tri(meth)acrylate, dipentaerythritol penta(meth)acrylate, and 2-hydroxy-3-(meth)acryloyloxypropyl(meth)acrylate.

[0054] Polyhydroxyl poly(meth)acrylates are compounds that have multiple hydroxyl groups and multiple (meth)acryloyl groups in a single molecule. Examples of polyhydroxyl poly(meth)acrylates include pentaerythritol di(meth)acrylate, dipentaerythritol tri(meth)acrylate, and dipentaerythritol tetra(meth)acrylate.

[0055] These hydroxyl group-containing unsaturated compounds can be used alone or in combination of two or more. Preferred hydroxyl group-containing unsaturated compounds include hydroxyl group-containing (meth)acrylates, more preferably monohydroxyl mono(meth)acrylates, monohydroxyl poly(meth)acrylates, even more preferably monohydroxyl mono(meth)acrylates, even more preferably hydroxyalkyl (meth)acrylates, and particularly preferably 2-hydroxyethyl (meth)acrylates.

[0056] In this method, for example, under an inert gas atmosphere, the above-mentioned isocyato-terminated prepolymer and a hydroxyl-containing unsaturated compound are blended in a predetermined equivalent ratio and subjected to a urethane reaction.

[0057] The equivalent ratio of isocyanate groups in the isocyanate-terminated prepolymer to hydroxyl groups in the hydroxyl-containing unsaturated compound (isocyanate group / hydroxyl group) is, for example, 0.7 or more, preferably 0.9 or more, and for example, 1.5 or less, preferably 1.2 or less.

[0058] Furthermore, the reaction conditions are not particularly limited and are set appropriately according to the purpose and application. For example, the reaction temperature may be, for example, 40°C or higher, preferably 50°C or higher, and more preferably 60°C or higher. Alternatively, the reaction temperature may be, for example, 120°C or lower, preferably 100°C or lower, and more preferably 80°C or lower. The reaction time may be, for example, 0.5 hours or more, preferably 1.0 hour or more. Alternatively, the reaction time may be, for example, 24 hours or less, preferably 10 hours or less.

[0059] Furthermore, in the above reaction, a known urethane catalyst may be added as needed. The proportion of the urethane catalyst added should be set appropriately according to the purpose and application.

[0060] This yields a radical-curable urethane resin containing reaction products with an isocyanate-terminated prepolymer and a compound having a hydroxyl-containing (meth)acroyl group.

[0061] More specifically, the radical-curable polyurethane resin is obtained by a urethane reaction between the isocyanate group of an isocyanate-terminated prepolymer and the hydroxyl group of a hydroxyl-containing (meth)acroyl compound, and is a polyurethane resin having (meth)acrylic groups derived from the hydroxyl-containing (meth)acroyl compound.

[0062] 3. Compounds having epoxy groups and / or oxetanyl groups (B) Compound (B) is a compound having an epoxy group and / or an oxetanyl group, but not a (meth)acryloyl group. Examples of compounds having an epoxy group include bisphenol-type epoxy compounds such as butyl glycidyl ether, phenyl glycidyl ether, bisphenol A-type epoxy compounds, bisphenol F-type epoxy compounds, bisphenol AD-type epoxy compounds, and bisphenol S-type epoxy compounds; naphthalene-type epoxy compounds; novolac-type epoxy compounds such as phenol novolac-type epoxy compounds and cresol novolac-type epoxy compounds; alcohol-type epoxy compounds such as hydrogenated bisphenol A-type epoxy compounds; and brominated epoxidized compounds. Examples include halogenated epoxy compounds such as compound epoxys; polyfunctional epoxy compounds. Specific examples include bisphenol A type epoxy compounds such as EPICLON 850, 850-S, and EXA-850CPR from DIC Corporation; bisphenol F type epoxy compounds such as EPICLON 830-S and EXA-830LVP from DIC Corporation; naphthalene type epoxy compounds such as HP-4032D of EPICLON from DIC Corporation; dicyclopentadiene type epoxy compounds such as HP-7200 and HP-7200HHH from DIC Corporation; and EPICLON from DIC Corporation. Examples include phenol novolac type epoxy compounds such as N-740 and N-770; cresol novolac type epoxy compounds such as EPICLON N-660, N-670, and N-655-EXP-S manufactured by DIC Corporation; flexible and tough epoxy resins such as EPICLON EXA-4850 manufactured by DIC Corporation; fluorene epoxy compounds such as PG-100 and CG-500 manufactured by Osaka Gas Chemical Co., Ltd.; polyfunctional epoxy compounds such as glycidyl ethers of tetra(hydroxyphenyl)alkanes, glycidyl ethers of tetrahydroxybenzophenone, and epoxidized polyvinylphenols.

[0063] Examples of aliphatic epoxy compounds include polyglycidyl ethers of polyhydric alcohols or their alkylene oxide adducts. Specific examples include ethylene glycol diglycidyl ether, diethylene glycol diglycidyl ether, propylene glycol diglycidyl ether, 1,4-butanediol diglycidyl ether, neopentyl glycol diglycidyl ether, 1,6-hexanediol diglycidyl ether, 1,9-nonanediol diglycidyl ether, 1,12-dodecanediol diglycidyl ether, glycerin triglycidyl lutein, trimethylolpropane triglycidyl ether (Epolite 100MF manufactured by Kyoeisha Chemical Co., Ltd.), polyethylene glycol diglycidyl ether, and the like.

[0064] Examples of alicyclic epoxy compounds include hydrogenated aromatic epoxy compounds, cyclohexane-based, cyclohexylmethyl ester-based, cyclohexylmethyl ether-based, spiro-based, and tricyclodecane-based epoxy compounds. Specific examples include hydrogenated bisphenol A type epoxy compounds such as KRM-2408 from ADEKA and YX-8034 from JER; 3',4'-epoxycyclohexylmethyl 3,4-epoxycyclohexanecarboxylate, 1,2:8,9-diepoxylimonene, 1,2-epoxy-4-vinylcyclohexane, 1,2-epoxy-4-(2-oxyranyl)cyclohexane adduct of 2,2-bis(hydroxymethyl)-1-butanol (EHPE3150 from Daicel Corporation); and alicyclic epoxy compounds such as those represented by the following formula (IV-1).

[0065] Other compounds containing epoxy groups within the molecule include heterocyclic epoxy compounds, glycidyl ether type epoxy compounds, glycidyl ester type epoxy compounds, glycidylamine type epoxy compounds, rubber-modified epoxy compounds, urethane-modified epoxy compounds, epoxidized polybutadiene, epoxidized styrene-butadiene-styrene block copolymers, epoxy group-containing polyester compounds, epoxy group-containing polyurethane compounds, and epoxy group-containing acrylic compounds.

[0066] Specific examples of compounds having an oxetanyl group in the molecule include 3-ethyl-3-hydroxymethyloxetane (oxetane alcohol) (e.g., OXT-101 from Toagosei Co., Ltd.), 2-ethylhexyloxetane (e.g., OXT-212 from Toagosei Co., Ltd.), xylylenebisoxetane (XDO: e.g., OXT-121 from Toagosei Co., Ltd.), and 3-ethyl-3{[(3-ethyloxetane-3-yl)methoxy]methyl}oxetane Examples include tan (e.g., OXT-221 from Toagosei Co., Ltd.), oxetanylsilsesquioxetane (e.g., OXT-191 from Toagosei Co., Ltd.), phenol novolac oxetane (e.g., PHOX from Toagosei Co., Ltd.), and 3-ethyl-3-phenoxymethyl oxetane (POX: e.g., OXT-211 from Toagosei Co., Ltd.), and 3-ethyl-3-allyloxymethyl oxetane (e.g., AL-EOX from Yokkaichi Gosei Co., Ltd.).

[0067] 4. Radical polymerization initiator (C) Among radical polymerization initiators, examples of thermal radical polymerization initiators that generate radicals upon heating include organic peroxides such as ketone peroxides, peroxyketals, hydroperoxides, dialkyl peroxides, diacyl peroxides, peroxyesters, and peroxydicarbonates. One or more of these organic oxides can be used. The amount of these organic oxides is preferably 0.1 to 10 parts by mass, more preferably 0.5 to 3 parts by mass, relative to the total resin composition. Naphthenate metal complexes, dimethylaniline, quaternary ammonium salts, and phosphate esters can be used as curing accelerators for the above organic peroxides.

[0068] Among radical initiators, general initiators can be used as photoradical polymerization initiators that generate radicals upon light irradiation, such as 1-[4-(2-hydroxyethoxy)phenyl]-2-hydroxy-2-methyl-1-propan-1-one, 1-hydroxycyclohexylphenyl-ketone, benzophenone, 2,2-dimethoxy-1,2-diphenylethane-1-one, 2,4,6-trimethylbenzoyldiphenylphosphine oxide, 2,4,6-trimethylbenzoylphenylethoxyphosphine oxide, and 2-ben Zyl-2-dimethylamino-1-(4-morpholinophenyl)butanone-1, 2-hydroxy-2-methyl-1-phenyl-propan-1-one, 2-methyl-1-[4-methylthio]phenyl]-2-morpholinopropan-1-one, benzoin methyl ether, benzoin ethyl ether, benzoin isobutyl ether, benzoin isopropyl ether, bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide, 2-hydroxy-2-methyl-[4-(1-methylvinyl)phenyl]propanol oligomer, 2-Hydroxy-2-methyl-[4-(1-methylvinyl)phenyl]propanol oligomer, 2-Hydroxy-2-methyl-1-phenyl-1-propanone, isopropylthioxanthone, o-benzoylmethyl benzoate, [4-(methylphenylthio)phenyl]phenylmethane, 2,4-diethylthioxanthone, 2-chlorothioxanthone, benzophenone, ethylanthraquinone, benzophenone ammonium salt, thioxanthone ammonium salt, bis(2,6-dimethoxybenzoyl)-2,4,4-trimethylpentyl phenyl Sphin oxide, bis(2,6-dimethoxybenzoyl)-2,4,4-trimethylpentylphosphine oxide, 2,4,6-trimethylbenzophenone, 4-methylbenzophenone, 4,4'-bisdiethylaminobenzophenone, 1,4-dibenzoylbenzene, 10-butyl-2-chloroacridone, 2,2'-bis(o-chlorophenyl)4,5,4',5'-tetrakis(3,4,5-trimethoxyphenyl)1,2'-biimidazole, 2,2'-bis(o-chlorophenyl)4,5,4',5'-tetraphenyl-1,Examples of photoinitiators include 2'-biimidazole, 2-benzoylnaphthalene, 4-benzoylbiphenyl, 4-benzoyldiphenyl ether, acrylic benzophenone, bis(η5-2,4-cyclopentadien-1-yl)-bis(2,6-difluoro-3-(1H-pyrrole-1-yl)-phenyl)titanium, o-methylbenzoylbenzoate, p-dimethylaminobenzoate ethyl ester, p-dimethylaminobenzoate isoamyl ethyl ester, activated tertialamine, carbazole-phenone photoinitiators, acridine photoinitiators, triazine photoinitiators, and benzoyl photoinitiators. One or more of these photoinitiators can be used.

[0069] 5. Cationic polymerization initiator (D) Examples of thermal cationic polymerization initiators that generate cations upon heating include TA-60, TA-60B, TA-100, and TA-120 from Sunapro Corporation; Adeka Opton CP-77 and Adeka Opton CP-66 from ADEKA Corporation; CI-2639 and CI-2624 from Nippon Soda Co., Ltd.; CXC-1612 and CXC-1738 from King Industries Corporation; and Sun-Aid SI-45, Sun-Aid SI-60, Sun-Aid SI-80, Sun-Aid SI-100, Sun-Aid SI-110, Sun-Aid SI-B3, Sun-Aid SI-B3A, and Sun-Aid SI-B4 from Sanshin Chemical Industry Co., Ltd.

[0070] Examples of photocationic polymerization initiators that generate cations upon light irradiation include diphenyliodonium hexafluoroarsenate, di(4-chlorophenyl)iodonium hexafluoroarsenate, di(4-bromophenyl)iodonium hexafluoroarsenate, phenyl(4-methoxyphenyl)iodonium hexafluoroarsenate, 4-methylphenyl-4-(1-methylethyl)phenyliodonium hexafluorophosphate, 4-methylphenyl-4-(1-methylethyl)phenyliodonium tri(pentafluoroethyl)trifluorophosphate (e.g., IK-1 from Sunapro), and 4-methyl Examples include phenyl-4-(1-methylethyl)phenyliodonium tetrakis(pentafluorophenyl)borate (e.g., PI-2074 from Rhodia Corporation), 4-methylphenyl-4-(2-methylpropyl)phenyliodonium hexafluorophosphate (e.g., IRGACURE® 250 from BASF), bis(C10~14-alkylphenyl)iodonium hexafluorophosphate (e.g., WPI-113 from Wako Pure Chemical Industries, Ltd.), and 4-methylphenyl-4-(1-methylethyl)phenyliodonium hexafluoroantimonate (e.g., WPI-116 from Wako Pure Chemical Industries, Ltd.). Such iodonium salts are commercially available from reagent suppliers, for example, as cationic initiators, and are readily available.

[0071] Photosensitizers are components used to increase sensitivity to light. Examples of photosensitizers include thioxanthone derivatives, carbonyl compounds, organosulfur compounds, persulfides, redox compounds, azo and diazo compounds, halogen compounds, and photoreducing dyes, with thioxanthone derivatives being preferred. Specific examples of thioxanthone derivatives include isopropylthioxanthone, 2,4-diethylthioxanthone, 2-chlorothioxanthone, 2,4-diethylthioxanthone, 2-chlorothioxanthone ammonium salts, with 2,4-diethylthioxanthone being preferred.

[0072] Furthermore, of the radical polymerization initiator (C) and the cationic polymerization initiator (D), preferably one is a photopolymerization initiator and the other is a thermal polymerization initiator.

[0073] The photosensitizer may be one type or a combination of two or more types.

[0074] 6. Other ingredients The resin composition of the present invention may contain fillers, antistatic agents, coupling agents, stabilizers, surfactants, and solvents, to the extent that it does not impair the purpose of the present invention.

[0075] [Filler] The material may contain fillers such as inorganic fillers, organic fillers, and carbon-type fillers for purposes such as imparting thixotropy, improving mechanical strength through filler addition, flame retardancy, coloring, conductivity, and / or antistatic properties.

[0076] Examples of inorganic fillers include powders of metal oxides such as silica, zirconia, beryllium, magnesium oxide, titania, and iron oxide; sols such as colloidal silica, titania sol, and alumina sol; clay minerals such as talc, kaolinite, and smectite; carbides such as silicon carbide and titanium carbide; nitrides such as silicon nitride, aluminum nitride, and titanium nitride; borides such as boron nitride, titanium boride, and boron oxide; complex oxides such as mullite; hydroxides such as aluminum hydroxide, magnesium hydroxide, and iron hydroxide; salts such as barium titanate, strontium carbonate, magnesium silicate, lithium silicate, sodium silicate, potassium silicate, and glass, lithium cobaltate, and olivine-type lithium iron phosphate.

[0077] Examples of organic fillers include acrylic resins, epoxy resins, polyimides, and cellulose particles, fibers, and flakes.

[0078] Examples of carbon-based fillers include graphite, acetylene black, and carbon nanotubes.

[0079] These fillers may be used in powder form, or in the form of aqueous-dispersible colloids such as silica sols or aluminum sols, or dispersed in organic solvents such as organosols.

[0080] The filler particles preferably have an average particle diameter of 0.005 to 500 μm, and more preferably 0.01 to 100 μm. The average particle diameter and particle size distribution can be measured using, for example, a laser diffraction / scattering particle size distribution analyzer, specifically the LA-920 manufactured by Horiba, Ltd.

[0081] The filler can be included in an amount of, for example, 4,900 parts by mass or less per 100 parts by mass of the resin composition, preferably 0.1 to 1,900 parts by mass, and more preferably 10 to 900 parts by mass.

[0082] [Antistatic agent] Examples of antistatic agents include imidazolium salt derivatives such as 1,3-dimethylimidazolium methyl sulfate, 1-ethyl-3-methylimidazolium bis(pentafluoroethylsulfonyl)imide, and 1-ethyl-3-methylimidazolium bromide; pyridinium salt derivatives such as 3-methyl-1-propylpyridimium bis(trifluoromethylsulfonyl)imide and 1-butyl-3-methylpyridinium bis(trifluoromethylsulfonyl)imide; alkylammonium derivatives such as tetrabutylammonium heptadecafluorooctanesulfonate and tetraphenylammonium methanesulfonate; phosphonium salt derivatives such as tetrabutylphosphonium methanesulfonate; and composite conductivity imparters such as polyalkylene glycol and lithium perchlorate.

[0083] The antistatic agent can be included in the resin composition in an amount of, for example, 40 parts by mass or less per 100 parts by mass, preferably 0.01 to 40 parts by mass, more preferably 0.1 to 30 parts by mass, and even more preferably 0.5 to 5 parts by mass.

[0084] [Coupling agent] As coupling agents, the following are used: (tridecafluoro-1,1,2,2-tetrahydrooctyl)triethoxysilane as a fluorine-based silane coupling agent; a coupling agent manufactured by Shin-Etsu Chemical Co., Ltd. (product name: KBM-403) as an epoxy-modified silane coupling agent; a coupling agent manufactured by Toagosei Co., Ltd. (product name: TESOX) as an oxetane-modified silane coupling agent; or vinyltrimethoxysilane, vinyltriethoxysilane, γ-chloropropyltrimethoxysilane, γ-aminopropyltriethoxysilane. Silane coupling agents such as N-(β-aminoethyl)-γ-aminopropyltrimethoxysilane, N-(β-aminoethyl)-γ-aminopropylmethyldimethoxysilane, γ-glycidoxypropyltrimethoxysilane, β-glycidoxypropylmethyldimethoxysilane, γ-methacryloxypropyltrimethoxysilane, γ-methacryloxypropylmethyldimethoxysilane, γ-mercaptopropyltrimethoxysilane, cyanohydrin silyl ether, and triethanolamine titanate, titanium ether Cetyl acetonate, titanium ethyl acetoacetate, titanium lactate, titanium lactate ammonium salt, tetrastearyl titanate, isopropyl tricumylphenyl titanate, isopropyl tri(N-aminoethyl-aminoethyl) titanate, dicumylphenyl oxyacetate titanate, isopropyl trioctanol titanate, isopropyl dimethacryisostearoyl titanate, titanium lactate ethyl ester, octylene glycol titanate, isopropyl triisostearoyl Iol titanate, triisostearyl isopropyl titanate, isopropyl toridodecylbenzenesulfonyl titanate, tetra(2-ethylhexyl) titanate, butyl titanate dimer, isopropyl isostearoyl diacrylic titanate, isopropyl tri(dioctyl phosphate) titanate, isopropyl tris(dioctyl pyrophosphate) titanate, tetraisopropyl bis(dioctyl phosphite) titanate, tetraoctyl bis(ditridecyl phosphite) titanate, tetra(2,Examples of titanium-based coupling agents include 2-diallyloxymethyl-1-butyl)bis(di-tridecyl)phosphite titanate, bis(dioctyl pyrophosphate)oxyacetate titanate, bis(dioctyl pyrophosphate)ethylene titanate, tetra-i-propyl titanate, tetra-n-butyl titanate, and diisostearoylethylene titanate. These coupling agents can be used individually or in combination of two or more as appropriate. Titanium-based coupling agents or silane coupling agents are preferred. Such coupling agents can be used to improve adhesion when molding a resin composition onto another substrate, but coating the filler surface with these coupling agents can also increase affinity with the matrix of the resin composition and improve mechanical strength.

[0085] The coupling agent can be included in the resin composition in an amount of, for example, 40 parts by mass or less per 100 parts by mass, preferably 0.01 to 40 parts by mass, more preferably 0.1 to 30 parts by mass, and even more preferably 0.5 to 5 parts by mass.

[0086] [Stabilizer] The resin composition may contain stabilizers.Such stabilizers are not particularly limited and include phenolic antioxidants such as 2,6-di-t-butylphenol, 2,4-di-t-butylphenol, 2,6-di-t-butyl-4-ethylphenol, 2,4-bis-(N-octylthio)-6-(4-hydroxy-3,5-di-t-butylanilino)-1,3,5-triazine; alkyldiphenylamine, N,N'-diphenyl-p-phenylenediamine, 6-ethoxy-2,2,4-trimethyl-1,2-dihydroquinoline, N-phenyl-N'-isopropyl-p-phenylenediamine Aromatic amine antioxidants such as dilauryl-3,3'-thiodipropionate, ditridecyl-3,3'-thiodipropionate, bis[2-methyl-4-{3-N-alkylthiopropionyloxy}-5-t-butylphenyl]sulfide, 2-mercapto-5-methylbenzimidazole, etc. Sulfide hydroperoxide decomposition agents such as tris(isodecyl)phosphite, phenyldiisooctylphosphite, diphenylisooctylphosphite, di(nonylphenyl)pentaerythritol diphosphite, 3,5- Phosphorus-based hydroperoxide decomposing agents such as di-t-butyl-4-hydroxybenzyl phosphate diethyl ester and sodium bis(4-t-butylphenyl) phosphate; salicylate-based light stabilizers such as phenyl salicylate and 4-t-octylphenyl salicylate; benzophenone-based light stabilizers such as 2,4-dihydroxybenzophenone and 2-hydroxy-4-methoxybenzophenone-5-sulfonic acid; 2-(2'-hydroxy-5'-methylphenyl)benzotriazole and 2,2'-methylenebis[4-(1,1,3,3-tetramethylbutyl) Examples include benzotriazole-based light stabilizers such as [-6-(2N-benzotriazole-2-yl)phenol]; hindered amine-based light stabilizers such as phenyl-4-piperidinyl carbonate and bis-[2,2,6,6-tetramethyl-4-piperidinyl] sebacate; Ni-based light stabilizers such as [2,2'-thio-bis(4-t-octylphenolate)]-2-ethylhexylamine-nickel(II); cyanoacrylate-based light stabilizers; oxalate-based light stabilizers; and fullerene-based light stabilizers such as fullerene, hydrogenated fullerene, and hydroxide-fullerene.These stabilizers may be used individually or in combination.

[0087] The stabilizer can be included in an amount of, for example, 10 parts by mass or less per 100 parts by mass of the resin composition, preferably 0.01 to 10 parts by mass, more preferably 0.05 to 5 parts by mass, and even more preferably 0.1 to 1 part by mass.

[0088] [Surfactants] The resin composition may contain surfactants to adjust wettability, defoaming, and / or smoothness, to the extent that it does not impair the coating properties.

[0089] Examples of surfactants include anionic surfactants, amphoteric surfactants, and nonionic surfactants.

[0090] Examples of anionic surfactants include soap, lauryl sulfate, polyoxyethylene alkyl ether sulfate, alkylbenzene sulfonate (e.g., dodecylbenzene sulfonate), polyoxyethylene alkyl ether phosphate, polyoxyethylene alkylphenyl ether phosphate, N-acyl amino acid salt, α-olefin sulfonate, alkyl sulfate ester, alkylphenyl ether sulfate ester, methyl taurate, trifluoromethanesulfonate, pentafluoroethanesulfonate, heptafluoropropanesulfonate, and nonafluorobutanesulfonate. Sodium ions and lithium ions can be used as countercations.

[0091] Examples of amphoteric surfactants include alkyldiaminoethylglycine hydrochloride, 2-alkyl-N-carboxymethyl-N-hydroxyethylimidazolinium betaine, lauryldimethylaminoacetic acid betaine, coconut oil fatty acid amidopropyl betaine, fatty acid alkyl betaine, sulfobetaine, and amine oxide.

[0092] Examples of nonionic surfactants include alkyl ester compounds of polyethylene glycol, alkyl ether compounds such as triethylene glycol monobutyl ether, ester compounds such as polyoxysorbitan esters, alkylphenol compounds, fluorine compounds, and silicone compounds.

[0093] Surfactants may be used individually or in combination.

[0094] The surfactant can be included in an amount of, for example, 50 parts by mass or less per 100 parts by mass of the resin composition, preferably 0.01 to 50 parts by mass, more preferably 0.05 to 20 parts by mass, and even more preferably 0.1 to 10 parts by mass.

[0095] [Method for producing resin compositions] The resin composition can be prepared by mixing and stirring the aforementioned components. Stirring can be carried out using stirring devices such as propeller mixers, planetary mixers, hybrid mixers, kneaders, emulsifying homogenizers, three-roll mills, bead mills, and ultrasonic homogenizers. Stirring can also be done while heating or cooling as needed.

[0096] (Heating method) For heating, various known methods such as hot air, hot plates, ovens, infrared radiation, and microwaves can be used. For cooling, various known methods such as natural cooling, cooling gas, and pressing against a heat sink can be used.

[0097] The resin composition of the present invention may further contain a solvent. The solvent may include hydrocarbons (propane, n-butane, n-pentane, isohexane, cyclohexane, n-octane, isooctane, benzene, toluene, xylene, ethylbenzene, amylbenzene, turpentine oil, pinene, etc.), halogenated hydrocarbons (methyl chloride, chloroform, carbon tetrachloride, ethylene chloride, methyl bromide, ethyl bromide, chlorobenzene, chlorobromomethane, bromobenzene, fluorodichloromethane, dichlorodifluoromethane, difluorochloroethane, etc.), alcohols (methanol, ethanol, 1-propanol, Isopropanol, 1-butanol, 1-pentanol, isoamyl alcohol, 1-hexanol, 1-heptanol, 1-octanol, 2-octanol, 1-dodecanol, nonanol, cyclohexanol, glycidol, etc.), ethers (diethyl ether, dichlorodiethyl ether, diisopropyl ether, dibutyl ether, diisoamyl ether, methylphenyl ether, ethyl benzyl ether), furans (tetrahydrofuran, furfural, 2-methylfuran, cineole, methylal), ketones (acetone, Methyl ethyl ketone, methyl-N-propyl ketone, methyl-N-amyl ketone, diisobutyl ketone, phorone, isophorone, cyclohexanone, acetophenone, etc.), esters (methyl formate, ethyl formate, propyl formate, methyl acetate, ethyl acetate, propyl acetate, n-amyl acetate, methyl cyclohexaneacetate, methyl butyrate, ethyl butyrate, propyl butyrate, butyl stearate, propylene carbonate, diethyl carbonate, ethylene carbonate, vinylene carbonate, etc.), polyhydric alcohols and their derivatives (ethylene glycol, ethylene glycol mo (Methyl ether, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether, methoxymethoxyethanol, ethylene glycol monoacetate, diethylene glycol, diethylene glycol monomethyl ether, propylene glycol, propylene glycol monoethyl ether, 2-(2-butoxyethoxy)ethanol, etc.), fatty acids and phenols (formic acid, acetic acid, acetic anhydride, propionic acid, propionic anhydride, butyric acid, isovaleric acid, phenol, cresol, o-cresol, xylenol, etc.),Examples of nitrogen compounds include nitrogen compounds (nitromethane, nitroethane, 1-nitropropane, nitrobenzene, monomethylamine, dimethylamine, trimethylamine, monoethylamine, diamylamine, aniline, monomethylaniline, o-toluidine, o-chloroaniline, diclohexylamine, dicyclohexylamine, monoethanolamine, formamide, N,N-dimethylformamide, acetamide, acetonitrile, pyridine, α-picoline, 2,4-lutidine, quinoline, morpholine, etc.), sulfur, phosphorus, other compounds (carbon disulfide, dimethyl sulfoxide, 4,4-diethyl-1,2-dithiolane, dimethyl sulfide, dimethyl disulfide, methanethiol, propanesultone, triethyl phosphate, tophenyl phosphate, diethyl carbonate, ethylene carbonate, amyl borate, etc.), inorganic solvents (liquid ammonia, silicone oil, etc.), and liquids such as water. These can be used individually or in combination of two or more types.

[0098] 4. Film manufacturing method In this method, the resin composition is prepared first.

[0099] The resin composition is not particularly limited and is prepared by mixing a compound (A) having a (meth)acryloyl group, a compound (B) having an epoxy group and / or an oxetanyl group, a radical initiator, a cationic initiator, and any other component in a known manner.

[0100] Compound (A) having a (meth)acryloyl group and compound (B) having an epoxy group and / or an oxetanyl group are appropriately selected from the viewpoint of compatibility so that a phase-separated molded article can be obtained.

[0101] From the viewpoint of adjusting the compatibility so that compound (A) having a (meth)acryloyl group and compound (B) having an epoxy group and / or an oxetanyl group separate into soft and hard segments, respectively, it is preferable that compound (A) having a (meth)acryloyl group and compound (B) having an epoxy group and / or an oxetanyl group can be selected based on the hydrogen bonding substituent value. The hydrogen bonding substituent is a group capable of forming hydrogen bonds, and examples include hydroxyl groups, mercapto groups, and amino groups.

[0102] The hydrogen bonding substituent values ​​allow for arbitrary adjustment of compatibility through hydrogen bonding. For example, by bringing the hydrogen bonding substituent values ​​of compound (A) having a (meth)acryloyl group and compound (B) having an epoxy group and / or oxetanyl group closer together, phase separation of the resin composition can be suppressed. Conversely, by moving the hydrogen bonding substituent values ​​of compound (A) having a (meth)acryloyl group and compound (B) having an epoxy group and / or oxetanyl group further apart, phase separation of the resin composition can be promoted.

[0103] Furthermore, in this resin composition, the hydrogen bonding substituent value of either compound (A) having a (meth)acryloyl group or compound (B) having an epoxy group and / or an oxetanyl group is 0.0001 mol / g or more, preferably 0.0005 mol / g or more, and 0.1111 mol / g or less, preferably 0.1000 mol / g or less.

[0104] Specifically, the hydrogen bonding substituent value of one molecule relative to the hydrogen bonding substituent value of the other molecule is 2 / 3 or less, preferably 1 / 2 or less, and for example, 1 / 100 or more, preferably 1 / 20.

[0105] More specifically, the hydrogen bonding substituent value of the other molecule is, for example, 0.000001 mol / g or more, preferably 0.000005 mol / g or more. Also, the hydrogen bonding substituent value of the other molecule is, for example, 0.0741 mol / g or less, preferably 0.0667 mol / g or less.

[0106] If the hydrogen bonding substituent value is within the above range, a phase separation structure can be formed by hydrogen bonding. The hydrogen bonding substituent value can be calculated using the following formula (1) based on the number of hydrogen bonding substituent values ​​contained in one molecule.

[0107] Hydrogen bonding substituent valency (mol / g) = Number of hydrogen-bonding substituents in one molecule ÷ Molecular weight (1)

[0108] The mixing ratio of compound (A) having a (meth)acryloyl group and compound (B) having an epoxy group and / or oxetanyl group is appropriately selected depending on the purpose and application. The contribution of the soft segment and the hard segment can be adjusted according to the volume ratio of compound (A) having a (meth)acryloyl group and compound (B) having an epoxy group and / or oxetanyl group. For example, the physical properties of the resin composition can be arbitrarily adjusted flexibly by increasing the amount of the soft segment and rigidly by decreasing it.

[0109] Furthermore, since the compatibility changes depending on the mixing ratio, the type of compound (A), and the type of compound (B), it can be arbitrarily adjusted from the perspective of generating a phase separation structure and exhibiting the desired properties.

[0110] Specifically, the content of compound (A) is, for example, 1 part by mass or more, preferably 5 parts by mass or more, more preferably 10 parts by mass or more, and also, for example, 55 parts by mass or less. Furthermore, the content of compound (B) is, for example, 45 parts by mass or more, and also, for example, 99 parts by mass or less, preferably 95 parts by mass or less, and more preferably 90 parts by mass or less, based on 100 parts by mass of the total amount of compound (A) and compound (B).

[0111] In particular, when compound (A) is a urethane (meth)acrylate and compound (B) is a naphthalene-type epoxy compound and an alicyclic epoxy compound, the content of compound (A) is, for example, 1 part by mass or more, preferably 5 parts by mass or more, more preferably 10 parts by mass or more, and for example, 50 parts by mass or less, preferably 45 parts by mass or less, based on 100 parts by mass of the total amount of compound (A) and compound (B). The content of compound (B) is, for example, 50 parts by mass or more, preferably 55 parts by mass or more, and for example, 99 parts by mass or less, preferably 95 parts by mass or less, and for example, 90 parts by mass or less, based on 100 parts by mass of the total amount of compound (A) and compound (B).

[0112] Furthermore, if compound (A) is a urethane (meth)acrylate and compound (B) is a fluorene-type epoxy compound and an alicyclic epoxy compound, the content of compound (A) is, for example, 1 part by mass or more, preferably 5 parts by mass or more, more preferably 10 parts by mass or more, and also, for example, 55 parts by mass or less. Furthermore, the content of compound (B) is, for example, 45 parts by mass or more, and also, for example, 99 parts by mass or less, preferably 95 parts by mass or less, and more preferably 90 parts by mass or less, based on 100 parts by mass of the total amount of compound (A) and compound (B).

[0113] Whether a phase separation structure has occurred can also be determined by whether the peak of the loss modulus tanδ is measured to be 2 or higher.

[0114] In this invention, as a result of diligent research, we have found that when the loss modulus derived from the soft segment is denoted as tanδ1 and the loss modulus derived from the hard segment as tanδ2, a flexible and heat-resistant film can be obtained when the peak position of tanδ1 is below 100°C (first peak), the peak position of tanδ2 is above 100°C (second peak), and the minimum value of the loss modulus tanδ3 between 100°C and below is 0.1 or less.

[0115] To achieve the above properties, the mixing ratio of compound (A) having a (meth)acryloyl group and compound (B) having an epoxy group and / or an oxetanyl group can be adjusted according to the desired physical properties.

[0116] 5. Method for manufacturing cured resin products A cured resin product is obtained by curing a resin composition.

[0117] The curing method is appropriately selected depending on the type of radical polymerization initiator (C) and cationic polymerization initiator (D).

[0118] Specifically, if the radical polymerization initiator (C) is a photo-radical polymerization initiator and the cationic polymerization initiator (D) is a photo-cationic polymerization initiator, the resin composition is cured by irradiation with active energy rays. If the radical polymerization initiator (C) is a thermal radical polymerization initiator and the cationic polymerization initiator (D) is a thermal cationic polymerization initiator, the resin composition is cured by heating. Furthermore, if the radical polymerization initiator (C) is a photo-radical polymerization initiator and the cationic polymerization initiator (D) is a thermal cationic polymerization initiator, or if the radical polymerization initiator (C) is a thermal radical polymerization initiator and the cationic polymerization initiator (D) is a photo-cationic polymerization initiator, the resin composition is cured by irradiation with active energy rays and heating.

[0119] Preferably, the resin composition is cured by irradiation with active energy rays alone, or by a combination of irradiation with active energy rays and heating.

[0120] The active energy ray is appropriately selected depending on the type of photoradical polymerization initiator and photocationic polymerization initiator, but ultraviolet light is preferred.

[0121] Furthermore, the heating conditions include a heating temperature of, for example, 30°C or higher, and 70°C or lower. The heating time is, for example, 10 minutes or more, and 120 minutes or less.

[0122] Furthermore, in particular when curing the resin composition by irradiation with active energy rays, it is preferable that the radical polymerization initiator (C) and the cationic polymerization initiator (D) are selected such that the absolute difference between the peak top position on the longer wavelength side of the photo-radical polymerization initiator's light absorption wavelength and the peak top position on the longer wavelength side of the photo-cationic polymerization initiator's light absorption wavelength is 30 nm or more.

[0123] In such cases, it is preferable to first irradiate with light having a wavelength corresponding to the relatively longer wavelength peak top position among the peak top positions of the radical polymerization initiator (C) and the cationic polymerization initiator (D), and then irradiate with light having a wavelength corresponding to the relatively shorter wavelength peak top position. This makes it possible to produce a resin cured product with even greater flexural strength and heat resistance.

[0124] This yields a cured resin product. Such cured resin products have excellent flexural strength and heat resistance, and are therefore particularly suitable for use as substrates for foldable displays used in liquid crystal displays and organic EL displays. [Examples]

[0125] Next, the present invention will be described based on examples and comparative examples, but the present invention is not limited to the following examples. Unless otherwise specified, "parts" and "%" are based on mass. Furthermore, specific numerical values ​​such as blending ratios (content), physical properties, and parameters used in the following description may be replaced with the corresponding upper limits (numerical values ​​defined as "less than or equal to" or "less than") or lower limits (numerical values ​​defined as "greater than or equal to" or "greater than") of the blending ratios (content), physical properties, and parameters described in the "Modes for Carrying Out the Invention" above.

[0126] Manufacturing Example 1 (1) Synthesis of isocyanate-terminated prepolymers Under a nitrogen atmosphere, 100 parts of polyoxypropylene polyol (Mitsui Chemicals SKC Polyurethane; DL10000, average number of functional groups 2, number average molecular weight 10000) as the polyol component were added to a glass separable flask. Next, 1,3-bis(isocyanatomethyl)cyclohexane (Mitsui Chemicals; 1,3-H6XDI) as the polyisocyanate component was added to the separable flask in an equivalent ratio (NCO / OH) of 8.0. The mixture was then heated to 80°C. Subsequently, stanoct (tin(II) ethylhexanoate) as a urethane catalyst was added in a concentration of 10 ppm relative to the mixture. The mixture was then reacted for 4 hours. This yielded a crude product containing an isocyanate-terminated prepolymer and unreacted polyisocyanate components.

[0127] (2) Purification of isocyanate-terminated prepolymer The crude product containing the isocyanate-terminated prepolymer was placed in a Smith thin-film distillation apparatus, and the isocyanate-terminated prepolymer and the unreacted polyisocyanate component were separated under the following conditions. This purified the isocyanate-terminated prepolymer. Temperature conditions: 160~170℃ Pressure conditions: 70-100 Pa Supply flow rate: 3.5-4g / min

[0128] (3) Synthesis of radical-curable polyurethane resin Under atmospheric conditions (dry air), 100 parts of the purified isocyanate-terminated prepolymer (purified prepolymer) were placed in a separable flask. Next, 2-hydroxyethyl acrylate was added to the separable flask as a hydroxyl-containing unsaturated compound in a ratio such that the equivalence ratio (NCO / OH) of the isocyanate groups of the isocyanate-terminated prepolymer to the hydroxyl groups of the hydroxyl-containing unsaturated compound was 1.0. The mixture was then heated to 70°C.

[0129] Subsequently, stanct (tin(II) ethylhexanoate) was added as a urethane catalyst at a concentration of 200 ppm relative to the isocyanate group-terminated prepolymer, and the mixture was reacted for 4 hours until the isocyanate group concentration fell to 0.01% or less. This synthesized radical-curable urethane acrylate resin 1.

[0130] Manufacturing Example 2 A radical-curable urethane acrylate resin 2 was synthesized based on the same procedure as in Production Example 1. However, in the synthesis of the isocyanate-terminated prepolymer, the polyol component was changed from polyoxypropylene polyol (Mitsui Chemicals SKC Polyurethane; DL10000, average number of functional groups 2, number average molecular weight 10000) to Actcol DL-4000 (average number of functional groups 2, number average molecular weight 4000, Mitsui Chemicals).

[0131] Manufacturing Example 3 100 parts of bisphenol A type epoxy resin (product name: EPICLON-7050) manufactured by DIC Corporation, 0.07 parts of triphenylphosphine, 0.03 parts of hydroquinone, and 100 parts of toluene were placed in a 500 ml three-necked flask. Under an argon atmosphere, 3.1 parts of acetic acid were added dropwise over 1 hour at 100°C and the mixture was heated for a further 4 hours. Then, 0.2 parts of xylene sulfonic acid were added and the mixture was stirred for a further 1 hour at 40°C. Toluene was removed by distillation using an evaporator to obtain partially esterified epoxy resin 4.

[0132] Manufacturing Example 4 100 parts of bisphenol A type epoxy resin (product name: EPICLON-850) manufactured by DIC Corporation, 0.07 parts of triphenylphosphine, 0.03 parts of hydroquinone, and 100 parts of toluene were placed in a 500 ml three-necked flask. Under an argon atmosphere, 16 parts of acetic acid were added dropwise over 1 hour at 100°C and the mixture was heated for a further 4 hours. Then, 0.2 parts of xylene sulfonic acid were added and the mixture was stirred for a further 1 hour at 40°C. Toluene was removed by distillation using an evaporator to obtain partially esterified epoxy resin 5.

[0133] Comparative Manufacturing Example 1 100 parts of bisphenol A type epoxy resin (product name: Epicote 1004, epoxy equivalent 900) manufactured by Shell Epoxy Co., Ltd., 0.07 parts of triphenylphosphine, 0.03 parts of hydroquinone, and 100 parts of toluene were placed in a 500 ml three-necked flask. Under an argon atmosphere, 4.0 parts of acetic acid were added dropwise over 1 hour at 100°C and the mixture was heated for a further 4 hours. Then, 0.2 parts of xylene sulfonic acid were added and the mixture was stirred for a further 1 hour at 40°C. Toluene was removed by distillation using an evaporator to obtain a partially acrylic epoxy resin.

[0134] Comparative Manufacturing Example 2 (1) Synthesis of isocyanate-terminated prepolymers Under a nitrogen atmosphere, 100 parts of polyester diol (Kuraray; P-1010, average number of functional groups 2, number average molecular weight 1000) as the polyol component were placed in a glass separable flask. Next, tolylene diisocyanate (Mitsui Chemicals; Cosmonate T-100) as the polyisocyanate component was added to the separable flask in an equivalent ratio (NCO / OH) of 2.0. The mixture was then heated to 80°C. Subsequently, stanoct (tin(II) ethylhexanoate) as a urethane catalyst was added in a concentration of 10 ppm relative to the mixture. The mixture was then reacted for 4 hours. This yielded a product containing an isocyanate-terminated prepolymer and unreacted polyisocyanate components.

[0135] (2) Synthesis of radical-curable polyurethane resin Under atmospheric conditions (dry air), 100 parts of the purified isocyanate-terminated prepolymer (purified prepolymer) were placed in a separable flask. Next, 2-hydroxyethyl acrylate was added to the separable flask as a hydroxyl-containing unsaturated compound in a ratio (NCO / OH) of isocyanate groups of the isocyanate-terminated prepolymer and unreacted polyisocyanate component to the hydroxyl groups of the hydroxyl-containing compound at a rate of 1.025. The mixture was then heated to 70°C.

[0136] Subsequently, stanct (tin(II) ethylhexanoate) was added as a urethane catalyst at a concentration of 200 ppm relative to the isocyanate group-terminated prepolymer, and the mixture was reacted for 4 hours until the isocyanate group concentration fell to 0.01% or less. This resulted in the synthesis of a radical-curable urethane acrylate resin.

[0137] (4) Preparation of resin composition Example 1 The following components were mixed at 25°C to obtain a resin composition. Manufacturing Example 1: 10 parts of urethane acrylate resin Epoxy resin 1 (manufactured by DIC Corporation; HP-4032D, naphthalene-type epoxy resin) 70 units Epoxy resin 2 (3',4'-epoxycyclohexylmethyl 3,4-epoxycyclohexanecarboxylate) 10 parts 10 parts of oxetane resin (OXT-212, 2-ethylhexyloxetane) Radical initiator (I'184, 1-hydroxycyclohexyl-phenyl ketone) 0.3 parts Cationic initiator (PI2074, (Tolycumyl)iodonium tetrakis(pentafluorophenyl)borate) 2 parts Sensitizer (DETX,2,4-Diethylthioxanthone) 0.1 part Radical source: Benzopinacol (part 1) Antioxidant (Inox10101, bis[3-(3-methyl-4-hydroxy-5-tert-butylphenyl)propionic acid]ethylene bisoxybisethylene) 1 part

[0138] (5) Formation of resin cured product A cured resin product was manufactured using the above resin composition by the method described below.

[0139] Using a doctor blade, the above resin composition was deposited into a PET film to obtain a coating with a thickness of 100 μm. Next, the coating was irradiated with active energy rays.

[0140] The output of the activated energy ray is 100 mW / cm². 2 (Measured using an illuminance meter (HIOKI 3664 optical power meter (measurement wavelength 405 nm)), with an integrated light intensity of 6000 mJ / cm²) 2 The device was irradiated to achieve the desired result. Next, it underwent thermal aging at 40°C for 30 minutes.

[0141] This cured (polymerized) the resin composition, yielding a cured resin product.

[0142] Example 2 A cured resin product was obtained using the same method as in Example 1, except that the proportion of urethane acrylate resin in Manufacturing Example 1 was increased.

[0143] Example 3 A cured resin product was obtained using the same method as in Example 2, except that the proportion of urethane acrylate resin in Manufacturing Example 1 was increased.

[0144] Example 4 A cured resin product was obtained using the same method as in Example 3, except that the proportion of urethane acrylate resin in Manufacturing Example 1 was increased.

[0145] Comparative Example 1 A cured resin product was obtained using the same method as in Example 4, except that the urethane acrylate resin from Manufacturing Example 1 was not incorporated.

[0146] Comparative Examples 2-7 A cured resin product was obtained using the same method as in Example 4, except that the proportion of urethane acrylate resin in Manufacturing Example 1 was increased.

[0147] Comparative Example 8 A cured resin product was obtained using the same method as in Example 4, except that the urethane acrylate resin from Manufacturing Example 1 was not incorporated, and Osaka Gas Chemical Co., Ltd., a fluorene-based epoxy resin, and OGSOL PG-100 (epoxy resin 3) were used.

[0148] Examples 5-9, Comparative Examples 9-13 Resin cured products were obtained using the same method as in Examples 1-4 and Comparative Examples 2-7, except that the epoxy resin used was changed from a naphthalene-type epoxy resin to a fluorene-based epoxy resin, OGSOL PG-100 (epoxy resin 3), manufactured by Osaka Gas Chemical Co., Ltd.

[0149] Example 10 A cured resin product was obtained using the same method as in Example 9, except that a peroxide (manufactured by NOF Corporation; Percure O, benzoyl peroxide) was used instead of a UV radical initiator, and the product was cured at 120°C for 30 minutes after UV curing.

[0150] Example 11 405nm × 1000mJ / cm 2 After UV curing, apply 365nm × 6000mJ / cm². 2 A resin cured product was obtained using the same method as in Example 9, except that it was further cured with UV light.

[0151] Example 12 A cured resin product was obtained using the same method as in Example 1, except that the urethane acrylate resin in Production Example 1 was replaced with the urethane acrylate resin in Production Example 2.

[0152] Example 13 A cured resin product was obtained in the same manner as in Example 12, except that epoxy resin 1 was replaced with epoxy resin 4 (epoxy resin from Production Example 3).

[0153] Example 14 A cured resin product was obtained in the same manner as in Example 1, except that epoxy resin 1 was replaced with epoxy resin 5 (epoxy resin from Production Example 4).

[0154] Comparative Example 14 (Based on Example 3 of Japanese Patent Publication No. 7-199359) Each component was mixed at 25°C according to the formulation below to obtain a resin composition, and a cured resin product was obtained in the same manner as in Example 1. 20 parts of partially acrylic epoxy resin from comparative manufacturing example 1 Comparative manufacturing example 2: Urethane acrylate resin (hydrogen bonding functional value (A) = 0.00268 (mol / g)) 20 parts Diethylene glycol divinyl ether 5 parts Triethylene glycol divinyl ether 3 parts Triphenylsulfonium hexafluoroantimonate 0.5 parts 1-Hydroxycyclohexylphenyl ketone 3 parts Diacrylate (manufactured by Daiichi Kogyo Seiyaku: BPE-10) 5 parts

[0155] <Rating> The properties were evaluated by dynamic viscoelasticity measurements and bending tests before and after the heat resistance test. Dynamic viscoelasticity measurements were performed using a dumbbell specimen type A, in tensile mode, at 10 Hz, -100 to 250°C, and 5°C / min. The storage modulus and tanδ were determined. For the heat resistance test, the specimen was heated in an oven at 260°C for 1 minute. The bending test was performed before and after the heat resistance test, with a bending angle of 180°, a bending diameter of 5 mm, and a bending speed of 1 Hz. The number of times the film tore was recorded. A pass was defined as 50,000 or more bending cycles both before and after the heat resistance test. The results are shown in Tables 1 and 2.

[0156] Furthermore, the resin composition of Example 1 was subjected to transmission electron microscopy. The results are shown in Figure 1.

[0157] [Table 1]

[0158] [Table 2]

[0159] The above invention is provided as an illustrative embodiment of the present invention, but this is merely illustrative and should not be interpreted restrictively. Modifications of the present invention that are obvious to those skilled in the art are included in the claims below. [Industrial applicability]

[0160] The resin composition, cured resin product, and method for producing the cured resin product of the present invention are suitably used in substrates for foldable displays used in liquid crystal displays and organic EL displays.

Claims

1. Compound (A) having a (meth)acryloyl group, Compound (B) having an epoxy group and / or an oxetanyl group, Radical polymerization initiator (C), A resin composition comprising a cationic polymerization initiator (D), The hydrogen bonding substituent value of compound (A) is 0.000753 mol / g or more and 0.000870 mol / g or less. The hydrogen bonding substituent value of compound (B) is 2 / 3 or less of the hydrogen bonding substituent value of compound (A), In the cured product of the aforementioned resin composition, the loss coefficient tanδ has two or more peaks. The aforementioned peak includes a first peak whose peak top position is less than 100°C and a second peak whose peak top position is 100°C or higher. The minimum value of the loss factor tanδ below 100℃ is 0.1 or less. The compound (A) is a urethane (meth)acrylate, which is a reaction product of an isocyanate-terminated prepolymer, which is a reaction product of a polyisocyanate component and a compound having a hydroxyl group, and a compound having a hydroxyl group-containing (meth)acroyl group. The compound having a hydroxyl group includes a polyether polyol. The compound (B) comprises 3',4'-epoxycyclohexylmethyl 3,4-epoxycyclohexanecarboxylate and 2-ethylhexyloxetane. The content ratio of compound (A) is 10 parts by mass or more and 50 parts by mass or less, based on 100 parts by mass of the total amount of compound (A) and compound (B). A resin composition in which the content of compound (B) is 50 parts by mass or more and 90 parts by mass or less, based on 100 parts by mass of the total amount of compound (A) and compound (B).

2. The resin composition according to claim 1, wherein one of the radical polymerization initiator (C) and the cationic polymerization initiator (D) is a photopolymerization initiator and the other is a thermal polymerization initiator.

3. A cured resin product which is a cured product of the resin composition according to claim 1 or 2.

4. A method for producing a cured resin product according to claim 3, In the resin composition, both the radical polymerization initiator (C) and the cationic polymerization initiator (D) are photopolymerization initiators. The difference between the peak top position on the longer wavelength side of the light absorption wavelength of the radical polymerization initiator (C) and the peak top position on the longer wavelength side of the light absorption wavelength of the cationic polymerization initiator (D) is 30 nm or more. A method for producing a cured resin product, comprising irradiating with light having a wavelength corresponding to the relatively longer wavelength peak top position among the peak top positions of the radical polymerization initiator (C) and the cationic polymerization initiator (D), and then irradiating with light having a wavelength corresponding to the relatively shorter wavelength peak top position.

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