Two-component curing resin composition

Abstract

Provided are a two-component curable resin composition that can be cured at room temperature, has excellent curing properties, and has high adhesive strength, and a cured product thereof. [Solution] A two-component curable resin composition in which the first component contains component (A), and the second component contains components (B), (C), and (D), with a mass ratio of component (B):component (C) of 99:1 to 26:74. (A) Component: Bisphenol epoxy resin (excluding hydrogenated bisphenol epoxy resin) Component (B): A mono- to tri-functional thiol curing agent having a polyether skeleton and no disulfide bond in the main chain Component (C): Thiol curing agent with a disulfide bond in the main chain Component (D): Curing accelerator

Description

[Technical Field]

[0001] The present invention relates to a two-component curable resin composition that can be cured at room temperature and has excellent curability and high adhesive strength. [Background technology]

[0002] Compositions using epoxy resins have been widely used in various fields due to their excellent heat resistance, chemical resistance, and adhesive properties. Furthermore, two-component curing epoxy resin adhesives that do not require a heat source have been attracting attention in recent years from the perspective of carbon neutrality. Patent Document 1 discloses a two-component curing epoxy resin composition that consists of a base agent containing a polyepoxide and a curing agent using dicyandiamide and an aliphatic polyamine. [Prior art documents] [Patent documents]

[0003] [Patent Document 1] Patent Publication No. 2024-18983 Summary of the Invention [Problem to be solved by the invention]

[0004] However, because amine-based curing agents have a slow curing rate, it is desirable to improve the curing rate of two-component curing epoxy resin compositions. Thiol-based curing agents are generally used to improve the curing rate of epoxy resins, but they have the problem of low adhesiveness. It has been particularly difficult to improve the adhesiveness of poorly adhesive resin materials. [Means for solving the problem]

[0005] As a result of intensive research to solve the above problems, the present inventors have discovered a two-component curable resin composition that does not require heat or a light source, can be cured at room temperature, and has excellent curability and high adhesive strength.

[0006] The gist of the present invention will now be described. [1] A two-component curable resin composition, wherein a first component contains the (A) component, and a second component contains the (B), (C) and (D) components, and the mass ratio of the (B) component:(C) component is 99:1 to 26:74. (A) Component: Bisphenol epoxy resin (excluding hydrogenated bisphenol epoxy resin) Component (B): A mono- to tri-functional thiol curing agent having a polyether skeleton and no disulfide bond in the main chain Component (C): Thiol curing agent with a disulfide bond in the main chain Component (D): Curing accelerator

[0007] [2] The two-component curable resin composition according to [1], wherein the component (A) is a bisphenol A type epoxy resin and / or a bisphenol F type epoxy resin.

[0008] [3] The two-component curable resin composition according to either [1] or [2], wherein the component (A) does not have a disulfide skeleton, a urethane skeleton, or an acrylonitrile-butadiene skeleton.

[0009] [4] The two-component curable resin composition according to either [1] or [2], wherein the component (B) is a trifunctional thiol curing agent.

[0010] [5] The two-component curable resin composition according to any one of [1] and [2], wherein the total amount of the components (B) and (C) is 50 to 170 parts by mass per 100 parts by mass of the component (A).

[0011] [6] The two-component curable resin composition according to any one of [1] and [2], comprising 30 to 100 parts by mass of the component (B) per 100 parts by mass of the component (A).

[0012] [7] The two-component curable resin composition according to either [1] or [2], wherein the component (D) is an amine compound.

[0013] [8] A cured product obtained by curing the two-component curing resin composition according to either [1] or [2]. [Effects of the Invention]

[0014] To provide a two-component curable resin composition which can be cured at room temperature without requiring heat or a light source, has excellent curability and high adhesive strength. DETAILED DESCRIPTION OF THE INVENTION

[0015] The present invention will be described in detail below. In this specification, "X to Y" is used to mean that the numerical values ​​(X and Y) before and after it are included as the lower limit and upper limit, and means "at least X and at most Y."

[0016] The component (A) used in the present invention is a bisphenol-type epoxy resin (excluding component (E)). Examples include bisphenol A-type epoxy resins, bisphenol F-type epoxy resins, bisphenol S-type epoxy resins, bisphenol AD-type epoxy resins, and brominated bisphenol A-type epoxy resins. From the viewpoint of excellent adhesive strength, bisphenol A-type epoxy resins and / or bisphenol F-type epoxy resins are preferred, and bisphenol A-type epoxy resins are more preferred. Hydrogenated bisphenol-type epoxy resins are not included in component (A) because of their poor curability. When an epoxy resin other than component (A) (excluding component (E)) is included, from the viewpoint of curability, the epoxy resin containing component (A) preferably contains 50% by mass or more of component (A), more preferably 65% ​​by mass or more, even more preferably 80% by mass or more, and most preferably 100% by mass of component (A). Furthermore, because of the risk of reduced curability, component (A) preferably does not contain a disulfide skeleton, a urethane skeleton, or an acrylonitrile-butadiene skeleton.

[0017] From the viewpoint of curability, the epoxy equivalent of the component (A) is preferably 50 g / eq to 400 g / eq, more preferably 100 g / eq to 300 g / eq. From the viewpoint of workability when mixing the two components, the viscosity of the component (A) at 25°C is preferably 0.1 Pa·s to 300 Pa·s, more preferably 1 Pa·s to less than 100 Pa·s, and most preferably 5 Pa·s to 20 Pa·s.

[0018] Commercially available products of the component (A) include, but are not limited to, jER828, 1001, 806, 807, and 152 (manufactured by Mitsubishi Chemical Corporation), Epiclon 830, EXA-830LVP, EXA-850CRP, and EXA-835LV (manufactured by DIC Corporation), and EP-4100, EP-4100G, EP-4100E, EP-4100TX, EP-4300E, EP-4400, EP-4520S, EP-4530, EP-4901, and EP-4901E (manufactured by ADEKA Corporation). These may be used alone or in combination of two or more.

[0019] The component (B) of the present invention is a mono- to tri-functional thiol curing agent having a polyether skeleton and no disulfide bond in the main chain. A thiol curing agent refers to a compound having an SH group. The number of SH groups may be one to three, but from the viewpoint of curing properties, a trifunctional thiol curing agent is preferred. Examples of the polyether skeleton include polymethylene oxide, polyethylene oxide, polypropylene oxide, and polybutylene oxide. From the viewpoint of excellent adhesive strength, a polypropylene oxide skeleton is preferred. Furthermore, from the viewpoint of excellent adhesive strength, the polyether skeleton preferably has one to five hydroxyl groups, more preferably one to three, and particularly preferably three. Commercially available products of the component (B) include, but are not limited to, polythiol QE-340M (manufactured by Toray Fine Chemicals Co., Ltd.).

[0020] The (B) component is preferably contained in an amount of 30 to 100 parts by mass, more preferably 50 to 90 parts by mass, and most preferably 60 to 85 parts by mass, per 100 parts by mass of the (A) component. When the amount is 30 parts by mass or more, excellent curability can be obtained, and when the amount is 100 parts by mass or less, excellent adhesive strength can be obtained.

[0021] The component (C) of the present invention is a thiol curing agent having a disulfide bond in its main chain. The disulfide bond refers to an S-S bond. The number of SH groups is not particularly limited, but is preferably monofunctional to tetrafunctional, more preferably difunctional to trifunctional, and most preferably difunctional. From the viewpoint of excellent adhesive strength, the component (C) preferably has a polyether skeleton. Examples of the polyether skeleton include polymethylene oxide, polyethylene oxide, polypropylene oxide, and polybutylene oxide. The component (C) preferably has a polymethylene oxide and / or polyethylene oxide skeleton, and more preferably a polymethylene oxide and polyethylene oxide skeleton. Commercially available products of the component (C) include, but are not limited to, the Thiokol LP series (manufactured by Toray Fine Chemicals Co., Ltd.).

[0022] The (C) component is preferably contained in an amount of 5 to 90 parts by mass, more preferably 10 to 70 parts by mass, and most preferably 15 to 65 parts by mass, per 100 parts by mass of the (A) component. When the amount is 5 parts by mass or more, excellent adhesive strength can be obtained, and when the amount is 90 parts by mass or less, excellent curability can be obtained.

[0023] The total amount of the (B) and (C) components is preferably 50 to 170 parts by mass, more preferably 70 to 160 parts by mass, and most preferably 90 to 150 parts by mass, per 100 parts by mass of the (A) component. If it is 50 parts by mass or more, excellent adhesive strength can be obtained, and if it is 170 parts by mass or less, excellent curability can be obtained.

[0024] The present invention is characterized in that the mass ratio of the (B) component to the (C) component is 99:1 to 26:74. By being within this range, a two-component curable resin composition that combines curability and adhesive strength can be obtained. Furthermore, from the viewpoint of achieving excellent curability and adhesive strength, the mass ratio is preferably 80:20 to 50:50, more preferably 90:10 to 60:40, and most preferably 80:20 to 70:30.

[0025] The present invention further includes a curing accelerator as component (D). The curing accelerator is not particularly limited as long as it can accelerate the curing of component (B). From the viewpoint of achieving room-temperature curing, it is preferable to include one or more compounds selected from the group consisting of imidazole compounds and amine compounds, more preferably amine compounds, and most preferably tertiary amine compounds. Specific examples of tertiary amine compounds include N,N,N',N'-tetramethyl-1,3-diaminopropane, N,N,N',N'-tetramethyl-1,6-diaminohexane, N,N-dimethylbenzylamine, N-methyl-N-(dimethylaminopropyl)aminoethanol, (dimethylaminomethyl)phenol, 2,4,6-tris(dimethylaminomethyl)phenol, tripropylamine, diazabicycloundecene, and diazabicyclononene. These may be used alone or in combination of two or more.

[0026] The amount of component (D) is preferably 0.1 to 20 parts by mass, more preferably 0.5 to 15 parts by mass, and most preferably 1 to 10 parts by mass, per 100 parts by mass of the total of components (B) and (C). When the amount is 0.1 to 20 parts by mass, room temperature curing can be achieved without reducing storage stability.

[0027] In the present invention, it is preferable to further include a silane coupling agent as component (E), which can improve adhesive strength. Examples of component (E) include glycidyl group-containing silane coupling agents such as 3-acryloxypropyltrimethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, 3-glycidoxypropylmethyldiethoxysilane, 3-glycidoxypropylmethyldipropyloxysilane, 3-glycidoxypropyldimethylmonomethoxysilane, 3-glycidoxypropyldimethylmonoethoxysilane, 3-glycidoxypropyldimethylmonopropyloxysilane, 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, 3-glycidoxypropyltriethoxysilane, 3-glycidoxypropyltrimethoxysilane, and 3-glycidoxypropylmethyldiethoxysilane; vinyl group-containing silane coupling agents such as vinyltris(β-methoxyethoxy)silane, vinyltriethoxysilane, and vinyltrimethoxysilane; 3-methacryloxypropylmethyldimethoxysilane, 3-methacryloxypropylmethyldiethoxysilane, and 3-methacryloxypropyl Examples of the silane coupling agents include (meth)acrylic group-containing silane coupling agents such as dimethyl monomethoxysilane, 3-methacryloxypropyl dimethyl monoethoxysilane, 3-acryloxypropyl methyl dipropyloxysilane, 3-acryloxypropyl methyl dimethoxysilane, 3-acryloxypropyl methyl diethoxysilane, 3-acryloxypropyl methyl dipropyloxysilane, 3-acryloxypropyl dimethyl monopropyloxysilane, 3-acryloxypropyl dimethyl monomethoxysilane, 3-acryloxypropyl dimethyl monoethoxysilane, 3-acryloxypropyl dimethyl monopropyloxysilane, and γ-methacryloxypropyl trimethoxysilane; amino group-containing silane coupling agents such as N-β-(aminoethyl)-γ-aminopropyl trimethoxysilane, γ-aminopropyl triethoxysilane, and N-phenyl-γ-aminopropyl trimethoxysilane; and γ-mercaptopropyl trimethoxysilane and γ-chloropropyl trimethoxysilane. Among these, a glycidyl group-containing silane coupling agent is more preferred from the viewpoint of excellent adhesive strength.These may be used alone or in combination of two or more. The preferred range of the blend amount of the silane coupling agent is 0.1 to 10 parts by mass per 100 parts by mass of the component (A) of the present invention.

[0028] In the present invention, it is preferable to further include an inorganic filler as component (F). Examples of the inorganic filler include alumina powder, calcium carbonate powder, talc powder, silica powder, fumed silica powder, silver powder, nickel powder, palladium powder, carbon powder, tungsten powder, and plating powder. From the viewpoint of adhesive strength, however, component (A) is preferably calcium carbonate powder. Furthermore, from the viewpoint of good compatibility with component (A), component (F) is preferably a surface-treated inorganic filler, more preferably an inorganic filler surface-treated with a fatty acid, and most preferably calcium carbonate powder surface-treated with a fatty acid. From the viewpoints of workability and adhesive strength, the blending amount of component (F) is preferably 5 to 80 mass% of each liquid formulation, more preferably 10 to 70%, and most preferably 20 to 60 mass%.

[0029] Furthermore, the composition may further contain appropriate amounts of additives such as organic fillers, pigments, dyes, leveling agents, rheology control agents, and storage stabilizers, within the range that does not impair the characteristics of the present invention.

[0030] The organic filler may be hollow or solid particles of organic materials composed of rubber, elastomer, plastic, polymer (or copolymer), etc. Organic fillers having a multilayer structure such as a core-shell type may also be used. The average particle size of the organic filler is preferably in the range of 0.05 to 50 μm. The preferred amount of the organic filler to be added is preferably 1 to 50 parts by mass, more preferably 5 to 30 parts by mass, per 100 parts by mass of (A).

[0031] The storage stabilizer may be boric acid ester, phosphoric acid, alkyl phosphate ester, or p-toluenesulfonic acid. Examples of boric acid ester include, but are not limited to, tributyl borate, trimethoxyboroxine, and ethyl borate. Examples of alkyl phosphate ester include, but are not limited to, trimethyl phosphate and tributyl phosphate. The storage stabilizers may be used alone or in combination. Considering the effect on curability, one or more selected from the group consisting of phosphoric acid, alkyl phosphate ester, boric acid ester, trimethoxyboroxine, and methyl p-toluenesulfonate are preferred, with phosphoric acid and boric acid ester being most preferred. From the viewpoints of curability and storage stability, the preferred amount of storage stabilizer is 0.1 to 10 parts by mass per 100 parts by mass of component (A) of the present invention.

[0032] <Application method> The two-component curable resin composition of the present invention can be applied to an adherend by a known method for applying a sealant or adhesive, such as dispensing using an automatic coater, spraying, inkjet printing, screen printing, gravure printing, dipping, or spin coating.

[0033] <Curing method> The two-component curable resin composition of the present invention can be cured at room temperature. In the present invention, room temperature refers to a temperature of 20° C. or higher and 30° C. or lower. The curing time is not particularly limited, but when cured at room temperature, it is preferably 1 minute or higher and 24 hours or lower, and more preferably 30 minutes or higher and 2 hours or lower, until adhesive strength is developed.

[0034] <Two-component curable resin composition> The two-component curable resin composition of the present invention is composed of two components from the viewpoints of carbon neutrality and storage stability. The two-component curable resin composition of the present invention is composed of a first component (main component) and a second component (curing agent), where the first component contains component (A), and the second component contains components (B), (C), and (D). From the viewpoint of workability, the mixing ratio of the first component (mass):second component (mass) is preferably 40:60 to 60:40.

[0035] When component (E), other than the essential components, is added to the first liquid of the two-component curable resin composition of the present invention, it is preferably added in an amount of 0.1 to 10 parts by mass per 100 parts by mass of component (A). Furthermore, when component (F) is added, it is preferably added in an amount of 1 to 200 parts by mass, more preferably 10 to 90 parts by mass, per 100 parts by mass of component (A). By keeping the amount within the above range, a first liquid that is easy to work with and free from the risk of separation can be obtained.

[0036] Furthermore, when component (F), other than the essential components, is added to the second liquid of the two-component curable resin composition of the present invention, the amount added is preferably 1 to 200 parts by mass, and more preferably 10 to 90 parts by mass, per 100 parts by mass of the total amount of components (B) and (C). By keeping the amount within the above range, a second liquid that is excellent in workability and does not separate can be obtained.

[0037] <Application> The curable resin composition of the present invention can be used in various applications. Specific examples include adhesives, seals, castings, coatings, etc. for automotive switches, headlamps, engine internal parts, electrical components, drive engines, brake oil tanks, front hoods, fenders, body panels such as doors, windows, etc., and Li-ion batteries; adhesives, seals, castings, coatings, etc. for flat panel displays (liquid crystal displays, organic EL displays, light-emitting diode displays, field emission displays), video discs, CDs, DVDs, MDs, pickup lenses, hard disks, etc. in the electronic materials field; adhesives, seals, castings, coatings, etc. for lithium batteries, lithium-ion batteries, manganese batteries, alkaline batteries, fuel cells, silicon solar cells, dye-sensitized batteries, organic solar cells, etc. in the battery field. In the optical components field, it is used for adhesives, sealing, and coatings for optical fiber materials around optical switches and optical connectors, optical passive components, optical circuit components, and optoelectronic integrated circuits. In the optical equipment field, it is used for adhesives, sealing, and coatings for camera modules, lens materials, viewfinder prisms, target prisms, viewfinder covers, light-receiving sensors, photographic lenses, and our company's lenses for projection televisions. In the infrastructure field, it can be used for adhesives, linings, seals, and coatings for gas pipes, water pipes, etc. However, because it has excellent adhesive strength between difficult-to-bond resin materials and aluminum and can be cured at room temperature, it is also suitable for use in heat-sensitive Li-ion batteries, which use PET / aluminum materials. [Example]

[0038] The present invention will now be described in more detail with reference to examples, but the present invention is not limited to these examples.

[0039] [Examples 1 to 3, Comparative Examples 1 to 11] The following components were prepared to prepare a two-component curable resin composition.

[0040] Component (A) (a-1): Bisphenol A epoxy resin. Product name: jER828 (manufactured by Mitsubishi Chemical Corporation). Functional groups: 2. Epoxy equivalent: 189 g / eq. Viscosity (25°C): 13.5 Pa·s. Component (A') (a'-1): Hydrogenated bisphenol type epoxy resin. Product name: Rikaresin HBE-100 (manufactured by New Japan Chemical Co., Ltd.). Functional group number: 2. Epoxy equivalent: 215 g / eq. Viscosity (25°C): 2 Pa·s. (a'-2): A polymer with a disulfide bond and polyether skeleton in the main chain and epoxy groups at the terminals (manufactured by Toray Industries, Inc.). Product name: FLEP-50. Number of functional groups: 2. Epoxy equivalent: 320 g / eq. Viscosity (20°C): 26 Pa·s (a'-3): Urethane-modified epoxy resin. Product name: EPU-73B (ADEKA Corporation). Epoxy equivalent: 245 g / eq. Viscosity (25°C): 130 Pa·s. (a'-4): NBR-modified epoxy resin. Product name: EPR-2007 (ADEKA Corporation). Epoxy equivalent: 310 g / eq. Viscosity (25°C): 120 Pa·s. ·(B) Component (b-1): A thiol curing agent (manufactured by Toray Industries, Inc.) that has a polypropylene oxide skeleton without a disulfide bond in the main chain and three hydroxyl groups in the side chain. SH functionality: 3. SH equivalent: 275 g / eq. Product name: Polythiol QE-340M ·(B') component (b'-1): Pentaerythritol tetrakis(3-mercaptobutyrate) (Showa Denko K.K.) SH functional group number: 4 SH equivalent: 136 g / eq Product name: Karenz MT PE-1 (b'-2): 1,3,5-tris(3-mercaptobutyryloxyethyl)-1,3,5-triazine-2,4,6(1H,3H,5H)-trione (Showa Denko K.K.) SH functional group number: 4 SH equivalent: 189 g / eq Product name: Karenz MT NR-1 (b'-3): Polyaminoamide compound (manufactured by T&K TOKA Corporation) Product name: TOMAID 235-R (b'-4): Liquid acrylonitrile-polybutadiene copolymer (manufactured by Ube Industries, Ltd.) Product name: ATBN1300X16 (b'-5): Polyaminoamide compound (manufactured by T&K TOKA Corporation) Product name: TOMAID TXA-525-EL (b'-6): Dicyandiamide (manufactured by Mitsubishi Chemical Corporation) Product name: DICY7 ·(C) component (c-1): A curing agent (manufactured by Toray Industries, Inc.) with a disulfide bond in the main chain, a polymethylene oxide skeleton, and a polyethylene oxide skeleton, and a thiol group at the end. SH functionality: 2. SH equivalent: 500 g / eq. Functionality: 2. Average molecular weight: 1000. Product name: Thiokol LP-3. ·(D) Component (d-1): 2,4,6-tris(dimethylaminomethyl)phenol (manufactured by Evonik Japan Co., Ltd.) Viscosity (25°C): 200 mPa·s Product name: Ancamine K54 ·(E) Component (e-1): 3-glycidoxypropyltrimethoxysilane (Shin-Etsu Chemical Co., Ltd.) Product name: KBM-403 (e-2): N-2-(aminoethyl)-3-aminopropyltriethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd.) Product name: KBM-603 Component (F) (f-1): Calcium carbonate surface-treated with fatty acid (manufactured by Shiraishi Kogyo Co., Ltd.) Product name: Hakuenka CCR (f-2): Calcium carbonate surface-treated with fatty acid (manufactured by Maruo Calcium Co., Ltd.) Product name: Calfine 500

[0041] The components (A) or (A'), (E), and (F) were weighed into a mixing vessel and stirred for 30 minutes in a mixer to obtain a first liquid. Then, components (B) or (B'), (C), (D), (E), and (F) were added, and the mixture was stirred for 10 minutes in a mixer to obtain a second liquid. The components were then mixed so that the ratio of the epoxy equivalent of the first liquid to the SH equivalent of the second liquid remained constant. The detailed amounts prepared are shown in Table 1. The total weight listed for the first liquid was mixed with the total weight listed for the second liquid. All values ​​are expressed in parts by mass. All tests were performed at 25°C. Note that hereinafter, the term "resin composition" refers to the mixture of the first and second liquids.

[0042] [Cureability test] Iron test pieces (SPCC-SD steel plates, 25 mm x 100 mm x 1.6 mm) were bonded together using the following procedure. The resin composition was applied to one test piece and spread evenly, and then the other test piece was attached to it so that the bonding surface was 25 mm in the width direction and 10 mm in the length direction. The test piece was left in a fixed position in a 25°C environment for 1 hour to cure. The prepared test piece was measured using a tensile tester at a tensile speed of 10 mm / min, and the "cure property" (MPa) was recorded. Test details were in accordance with JIS K6850:1999. [Evaluation criteria] 5.0MPa or more: Excellent Less than 5.0 MPa 3.0 MPa or more: Excellent Less than 3.0 MPa: Inferior

[0043] [Adhesion test] A 90° peel test was performed using an L-shaped aluminum plate (A1050P) measuring 25 mm wide x 150 mm long x 1 mm thick and a polyethylene terephthalate (PET) plate measuring 25 mm wide x 100 mm long x 2 mm thick. The resin composition was applied to the PET plate, and the 25 mm x 80 mm adhesive surface was fixed to the aluminum plate with a lamination jig. This was then left at 25°C for 24 hours to create a test piece. The aluminum plate side of the test piece was fixed in the chuck of a tensile tester, and the aluminum plate was pulled perpendicular to the PET plate at a speed of 50 mm / min, and the "adhesion strength" (kN / m) was measured. Test details were in accordance with JIS K6854:1999. [Evaluation criteria] 1.0kN / m or more: Excellent Less than 1.0 kN / m: Poor

[0044] [Table 1]

[0045] As shown in Table 1, Examples 1 to 3 were curable at room temperature and had excellent curability and adhesive strength. In particular, the curable resin composition of Example 1 exhibited superior curability and adhesive strength compared to Examples 2 and 3. On the other hand, Comparative Examples 1 to 3, which did not contain component (B) or component (C) or in which the blending ratio of component (B):(C) was outside the range of 99:1 to 26:74, exhibited poor adhesive strength, and Comparative Example 3 in particular did not cure. Comparative Examples 4 and 5 used a tetrafunctional thiol curing agent instead of component (B), but exhibited low adhesive strength. Comparative Examples 6 to 9 used an epoxy resin other than a bisphenol-type epoxy resin instead of component (A), but all exhibited poor curability. Comparative Examples 10 and 11 used an amine-based curing agent instead of components (B) and (C), but exhibited very poor curability. From the above, by combining components (A) to (D) in a predetermined ratio, a two-component curable resin composition that can be cured at room temperature and exhibits excellent curability and adhesive strength can be obtained. [Industrial Applicability]

[0046] The two-component curable resin composition of the present invention can be cured at room temperature and has excellent curability and adhesive strength, and is therefore useful in a variety of fields as an adhesive, coating agent, or potting agent.

Claims

1. A two-component curable resin composition comprising a first component (A) and a second component (B), (C), and (D), wherein the mass ratio of the component (B):the component (C) is 99:1 to 26:

74. Component (A): Bisphenol epoxy resin (excluding hydrogenated bisphenol epoxy resin) Component (B): A mono- to tri-functional thiol curing agent having a polyether skeleton and no disulfide bond in the main chain Component (C): a thiol curing agent having a disulfide bond in the main chain Component (D): Curing accelerator

2. 2. The two-component curable resin composition according to claim 1, wherein the component (A) is a bisphenol A type epoxy resin and / or a bisphenol F type epoxy resin.

3. 3. The two-component curable resin composition according to claim 1, wherein the component (A) does not have a disulfide skeleton, a urethane skeleton, or an acrylonitrile-butadiene skeleton.

4. The two-component curing resin composition according to claim 1 or 2, wherein the component (B) is a trifunctional thiol curing agent.

5. 3. The two-component curing resin composition according to claim 1, wherein the total amount of the components (B) and (C) is 50 to 170 parts by mass relative to 100 parts by mass of the component (A).

6. 3. The two-component curable resin composition according to claim 1, comprising 30 to 100 parts by mass of the component (B) relative to 100 parts by mass of the component (A).

7. The two-component curable resin composition according to claim 1 or 2, wherein the component (D) is an amine compound.

8. A cured product obtained by curing the two-component curing resin composition according to claim 1 or 2.

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