Two-component curable resin composition, cured product, laminate, and method for disassembling laminate

Abstract

The present disclosure relates to a two-component curable resin composition that does not contain an epoxy compound or a radical initiator and includes following components (A) to (C): component (A), which is a polyfunctional (meth)acrylate compound; component (B), which is a polyhydrazide compound that is solid at 25°C; and component (C), which is a solvent that is liquid at 25°C and dissolves component (B), or a dispersion medium that is liquid at 25°C and disperses component (B). The present disclosure makes it possible to provide a two-component curable resin composition that, when cured, can exhibit excellent adhesive strength and ease of decomposition by an oxidizing agent.

Description

Two-component curable resin composition, cured product, laminate, and method for dismantling the laminate.

[0001] The present invention relates to a two-component curable resin composition that forms a cured product that is easily decomposable by an oxidizing agent, a cured product of the two-component curable resin composition, a laminate formed using the cured product, and a method for dismantling the laminate.

[0002] Adhesives are used to bond two or more different materials together, and generally require high adhesive strength. However, in recent years, from the perspective of resource recycling, there has been a need for easily decomposable adhesives that allow for the decomposition of the cured material after use, enabling the dismantling and reuse of the materials (Republished Patent WO2007 / 083566 (corresponding to US Patent Application Publication 2009 / 0000736)). As an example of an easily decomposable adhesive, a method is known in which a cured product obtained by Michael addition reaction between a compound having one or more (meth)acryloyl groups in one molecule and a hydrazide compound is immersed in an aqueous solution containing an oxidizing agent to decompose it and dismantle the materials (Japanese Patent Application Publication No. 2024-081845 (corresponding to US Patent Application Publication 2024 / 0191110)).

[0003] However, adhesives containing a compound with one or more (meth)acryloyl groups in a single molecule and a hydrazide compound sometimes exhibited poor storage stability due to a slow Michael addition reaction. Furthermore, since hydrazide compounds are generally solids, it was difficult to simply formulate them into a two-part adhesive.

[0004] As a result of diligent research to solve at least one of the above problems, the present inventors have found a method for obtaining a two-component curable resin composition that exhibits excellent adhesion in the cured product and is easily decomposable in the cured product.

[0005] The gist of this invention is described below.

[0006] One aspect of the present invention that can solve at least one of the above problems relates to a two-component curable resin composition described in [1] below. [1] A two-component curable resin composition comprising the following components (A) to (C), wherein the first liquid comprises component (A), and the second liquid comprises components (B) and (C), wherein the two-component curable resin composition does not contain epoxy compounds and radical initiators: Component (A): a polyfunctional (meth)acrylate compound Component (B): a polyhydrazide compound that is solid at 25°C Component (C): a solvent that is liquid at 25°C and dissolves component (B), or a dispersion medium that is liquid at 25°C and disperses component (B).

[0007] The two-component curable resin composition described in [1] above can also be described as a two-component curable resin composition comprising the following components (A) to (C), without epoxy compounds or radical initiators, with the first liquid containing component (A) and the second liquid containing components (B) and (C): (A) component: polyfunctional (meth)acrylate compound (B) component: polyhydrazide compound that is solid at 25°C (C) component: a solvent that is liquid at 25°C and dissolves component (B), or a dispersion medium that is liquid at 25°C and disperses component (B).

[0008] The present invention includes, as non-limiting examples of preferred embodiments, embodiments shown in [2] to

[19] below. [2] The two-component curable resin composition according to [1], wherein component (C) is an amine compound as component (C1) (particularly preferably at least one compound selected from the group consisting of cardanol-modified amine, trimethylolpropane poly(oxypropylene)triamine, polyaminoamide and triethylenetetramine; even more preferably cardanol-modified amine) and / or a plasticizer as component (C2) (particularly preferably at least one compound selected from the group consisting of dibutyl phthalate, diheptyl phthalate, di(2-ethylhexyl) phthalate, butyl benzyl phthalate, butyl oleate, diethylene glycol dibenzoate, triethylene glycol dibenzoate, pentaerythritol ester, polyethylene glycol, polypropylene glycol, polytetramethylene glycol, cardanol-modified plasticizer and polyester plasticizer obtained from a dibasic acid and a dihydric alcohol; even more preferably cardanol-modified plasticizer). [3] The two-component curable resin compound according to [1] or [2], wherein the viscosity of component (C) is 1 to 10,000 mPa·s. [4] The two-component curable resin composition according to any one of [1] to [3], comprising 5 to 80 parts by mass of component (B) per 100 parts by mass of component (A). [5] The two-component curable resin composition according to any one of [1] to [4], wherein the mixed mass ratio of component (B) to component (C) (component (B):component (C)) is 1:0.5 to 1:3. [6] The two-component curable resin composition according to any one of [1] to [5], wherein component (A) comprises a bifunctional (meth)acrylate compound and / or a trifunctional or more (meth)acrylate compound (particularly preferably at least one compound selected from the group consisting of polyethylene glycol di(meth)acrylate and polyethylene glycol-modified polyglycerin hexa(meth)acrylate; even more preferably polyethylene glycol diacrylate and polyethylene glycol-modified polyglycerin hexaacrylate). [7] The two-component curable resin composition according to any one of [1] to [6], wherein component (A) comprises a trifunctional or more polyfunctional (meth)acrylate compound.[8] The two-component curable resin composition according to any one of [1] to [7], wherein the component (B) is a dihydrazide compound (particularly preferably a dihydrazide compound having an aromatic ring; even more preferably isophthalic acid dihydrazide). [9] The two-component curable resin composition according to any one of [1] to [8], further comprising a filler (preferably at least one selected from the group consisting of silica powder, calcium carbonate powder, and acrylic filler; particularly preferably silica powder and acrylic filler) as component (D).

[10] The two-component curable resin composition according to [9], wherein the first liquid comprises the component (D).

[11] The two-component curable resin composition according to any one of [1] to

[10] , further comprising a monofunctional (meth)acrylate compound (particularly preferably 2-hydroxyethyl (meth)acrylate acid phosphate; even more preferably 2-hydroxyethyl methacrylate acid phosphate) as component (E).

[12] The two-component curable resin composition according to

[11] , wherein the first liquid comprises the component (E).

[13] A composition set comprising the first liquid and the second liquid separately, wherein the first liquid and the second liquid do not contain epoxy compounds and radical initiators, the two-component curable resin composition according to any one of [1] to

[12] .

[14] A mixture obtained by mixing the first liquid and the second liquid (i.e., a mixture of the first liquid and the second liquid), wherein the first liquid and the second liquid do not contain epoxy compounds and radical initiators, the two-component curable resin composition according to any one of [1] to

[13] .

[15] A method of using the two-component curable resin composition according to any one of [1] to

[12] , comprising mixing the first liquid and the second liquid.

[16] A cured product obtained by curing the two-component curable resin composition according to any one of [1] to

[14] . A laminate comprising two adherends, each having a region on one or both of the adherends on one or both of the adherends on one or both of the adherends on which the two-component curable resin composition is applied, and then bonding the two adherends together at a portion of at least one of the adherends that includes the region on which the two-component curable resin composition is applied, and then curing the two-component curable resin composition.

[18] A laminate comprising two adherends, each having a cured layer obtained by applying a two-component curable resin composition described in any of [1] to

[14] to at least one of the adherends and curing it, the two adherends being bonded together with an adhesive such that the cured layer in at least one of the adherends is in contact with an adhesive other than the two-component curable resin composition, and the adhesive being cured.

[19] A method for dismantling a laminate according to

[17] or

[18] , comprising immersing the laminate according to

[17] or

[18] in an aqueous solution containing an oxidizing agent to decompose the cured product of the two-component curable resin composition and dismantle it.

[0009] The details of the present invention will now be described. While embodiments of the present invention will be described below, the present invention is not limited to these embodiments and can be modified in various ways within the scope of the claims. The embodiments described herein can be combined in any way to form other embodiments.

[0010] 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 and upper limits, respectively, and means "X or greater and Y or less."

[0011] In this specification, unless otherwise specified, operations and measurements of physical properties shall be performed under conditions of room temperature (20°C to 25°C) and relative humidity of 45% RH to 55% RH.

[0012] In this specification, "A and / or B" means that A, B, each of them, and any combination thereof are included.

[0013] <Two-component curable resin composition> One aspect of the present invention relates to a two-component curable resin composition comprising the following components (A) to (C), but not containing epoxy compounds or radical initiators, wherein the first liquid contains component (A), and the second liquid contains components (B) and (C): (A) component: polyfunctional (meth)acrylate compound (B) component: polyhydrazide compound that is solid at 25°C (C) component: a solvent that is liquid at 25°C and dissolves component (B), or a dispersion medium that is liquid at 25°C and disperses component (B).

[0014] Here, the two-component curable resin composition according to this embodiment preferably comprises a first liquid and a second liquid separately, wherein the first liquid contains component (A), the second liquid contains component (B) and component (C), and neither the first liquid nor the second liquid contains an epoxy compound and a radical initiator, and is a composition set. In this case, the two-component curable resin composition does not contain an epoxy compound and a radical initiator. Alternatively, the two-component curable resin composition according to this embodiment may be a mixture obtained by mixing a first liquid containing component (A) and a second liquid containing component (B) and component (C) (i.e., a mixture of a first liquid containing component (A) and a second liquid containing component (B) and component (C)), and the first liquid and the second liquid do not contain an epoxy compound and a radical initiator, and is a two-component curable resin composition. In this case, the two-component curable resin composition does not contain an epoxy compound and a radical initiator.

[0015] According to the two-component curable resin composition of this embodiment, excellent adhesive strength and easy decomposition by an oxidizing agent can be achieved upon curing. For example, the two-component curable resin composition according to the preferred embodiment can exhibit excellent adhesive strength and easy decomposition by an oxidizing agent, and furthermore, it can achieve excellent pot life during use and excellent storage stability during storage, with at least one of these properties being selected from the group.

[0016] As described above, the two-component curable resin composition according to this embodiment is a two-component curable resin composition that does not contain epoxy compounds or radical initiators. Here, the two-component curable resin composition according to this embodiment includes the above components (A) to (C). The characteristics of each component and the two-component curable resin composition will be described below.

[0017] [Component (A)] Component (A) is a polyfunctional (meth)acrylate compound.

[0018] In this specification, compounds having a (meth)acryloyl group include (meth)acrylate compounds. Compounds having a (meth)acryloyl group may also have the (meth)acryloyl group in the form of a (meth)acryloyloxy group. In this specification, the term "(meth)acryloyl" includes both acryloyl and methacryloyl. Therefore, for example, the term "(meth)acryloyl group" includes the acryloyl group (H ２ C=CH-C(=O)-) and methacryloyl group (H ２ C = C(CH) ３ It encompasses both )-C(=O)-). Similarly, for example, the term "(meth)acryloyloxy group" includes the acryloyloxy group (H ２ C=CH-C(=O)-O-) and methacryloyloxy group (H ２ C = C(CH) ３ It encompasses both )-C(=O)-O-). For example, the term "(meth)acrylate" encompasses both acrylate and methacrylate, for example, the term "(meth)acrylic" encompasses both acrylic and methacrylic, for example, the term "(meth)acrylamide" encompasses both acrylamide and methacrylamide.

[0019] The polyfunctional (meth)acrylate compound of component (A) is a (meth)acrylate compound having two or more (meth)acryloyl groups. In the polyfunctional (meth)acrylate compound, at least one (meth)acrylic group ((meth)acryloyl group) is a (meth)acryloyloxy group. The polyfunctional (meth)acrylate compound of component (A) preferably contains a (meth)acrylate compound having two or more (meth)acryloyloxy groups, and more preferably contains an acrylate compound having two or more acryloyloxy groups. The polyfunctional (meth)acrylate compound of component (A) preferably is a (meth)acrylate compound having two or more (meth)acryloyloxy groups, and more preferably is an acrylate compound having two or more acryloyloxy groups. Examples of polyfunctional (meth)acrylate compounds include polyfunctional (meth)acrylate oligomers and polyfunctional (meth)acrylate monomers. In this specification, a (meth)acrylate oligomer is a polymer having one or more (meth)acrylic groups ((meth)acryloyl groups) and repeating monomer units (which may include monomer units other than (meth)acrylate monomers) in a number of 2 to several tens (for example, 2 to 10, 2 to 15, 2 to 20, or 2 to 30). The monomer units in the (meth)acrylate oligomer preferably include monomer units other than (meth)acrylate monomers, and it is particularly preferable that they be monomer units other than (meth)acrylate monomers. It is particularly preferable that the (meth)acrylate oligomer is a polymer having one or more (meth)acrylic groups ((meth)acryloyl groups) and repeating monomer units other than (meth)acrylate monomers in a number of 2 to several tens (for example, 2 to 10, 2 to 15, 2 to 20, or 2 to 30). In the (meth)acrylate oligomer, at least one (meth)acrylic group ((meth)acryloyl group) is a (meth)acryloyloxy group. The (meth)acrylate oligomer preferably has a molecular weight of less than 2000 (0.2 million). The molecular weight is expressed as the value calculated from the sum of atomic weights if it can be calculated from the sum of atomic weights, and as the weight-average molecular weight if it is difficult to calculate from the sum of atomic weights.In this specification, a polymer has a weight-average molecular weight of 2,000 (0.2 million) or more. From the viewpoint of decomposition by oxidizing agents, component (A) preferably contains a polyfunctional (meth)acrylate oligomer, and more preferably component (A) is a polyfunctional (meth)acrylate oligomer. From the viewpoint of adhesive strength of the cured product, component (A) is preferably a polyfunctional acrylate compound.

[0020] If the two-component curable resin composition according to this embodiment contains a monofunctional (meth)acrylate compound which is component (E) described later, it is preferable that the two-component curable resin composition according to this embodiment contains 80% by mass or more of component (A) relative to the total mass (parts by mass) of component (E) and component (A). It is more preferable that the two-component curable resin composition according to this embodiment contains 90% by mass or more of component (A) relative to the total mass of component (E) and component (A). It is even more preferable that the two-component curable resin composition according to this embodiment contains 95% by mass or more of component (A) relative to the total mass of component (E) and component (A). For example, the two-component curable resin composition according to this embodiment may contain 95% by mass of component (A) relative to the total mass of component (E) and component (A). By containing 80% by mass or more of component (A) relative to the total mass (parts by mass) of component (E) and component (A) in the two-component curable resin composition according to this embodiment, the adhesive strength of the cured product can be maintained more effectively. For example, the two-component curable resin composition according to this embodiment may contain 80% to 100% by mass of component (A) relative to the total mass of component (E) and component (A). For example, the two-component curable resin composition according to this embodiment may contain 90% to less than 100% by mass of component (A) relative to the total mass of component (E) and component (A). For example, the two-component curable resin composition according to this embodiment may contain 95% to 99% by mass of component (A) relative to the total mass of component (E) and component (A). For example, the two-component curable resin composition according to this embodiment may contain 97% to 100% by mass of component (A) relative to the total mass of component (E) and component (A). For example, the two-component curable resin composition according to this embodiment may contain 98% to 100% by mass of component (A) relative to the total mass of component (E) and component (A). (A) When two or more components are used, the amount of component (A) represents the sum of these components. (E) When two or more components are used, the amount of component (E) represents the sum of these components.

[0021] Examples of polyfunctional (meth)acrylate oligomers include polyfunctional ester (meth)acrylate oligomers having ester bonds (i.e., polyfunctional (meth)acrylate oligomers having ester bonds in the molecule), polyfunctional ether (meth)acrylate oligomers having ether groups (i.e., polyfunctional (meth)acrylate oligomers having ether groups in the molecule), and polyfunctional urethane (meth)acrylate oligomers having urethane bonds (i.e., polyfunctional (meth)acrylate oligomers having urethane bonds in the molecule). Examples of the main skeletons of polyfunctional (meth)acrylate oligomers include bisphenol A skeletons (i.e., skeletons containing one or more substructures derived from bisphenol A and containing repeating units), novolacphenol skeletons, polybutadiene skeletons, hydrogenated polybutadiene skeletons, polyester skeletons, polyether skeletons, polycarbonate skeletons, castor oil skeletons, isoprene skeletons, hydrogenated isoprene skeletons, polyglycerin skeletons, acrylic polymer skeletons, and skeletons consisting of two or more combinations of these. The bisphenol A skeleton is not particularly limited. Examples of the bisphenol A skeleton include the ethoxylated bisphenol A skeleton (a structure in which the hydrogen atoms of the hydroxyl groups at both ends of bisphenol A are replaced by oxyethylene groups).

[0022] Examples of polyfunctional (meth)acrylate compounds include triethylene glycol di(meth)acrylate, polyethylene glycol #200 di(meth)acrylate, polyethylene glycol #400 di(meth)acrylate, polyethylene glycol #600 di(meth)acrylate, polyethylene glycol #1000 di(meth)acrylate, tripropylene glycol di(meth)acrylate, polypropylene glycol #400 di(meth)acrylate, polypropylene glycol #700 di(meth)acrylate, and polyethylene glycol di(meth)acrylate. Lamethylene glycol di(meth)acrylate, neopentyl glycol di(meth)acrylate, 3-methyl-1,5-pentanediol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, 1,9-nonanediol di(meth)acrylate, 1,10-decanediol di(meth)acrylate, dimethylol tricyclodecane di(meth)acrylate, bisphenol A EO adduct di(meth)acrylate, bisphenol A PO adduct di(meth)acrylate, hydroxypivalate neopentyl glycol Recall (meth)acrylic acid adduct, 2-hydroxy-3-acryloyloxypropyl methacrylate, trimethylolpropane tri(meth)acrylate, ethoxylated trimethylolpropane tri(meth)acrylate, polyethylene glycol modified glycerin tri(meth)acrylate, bis(2-acryloxyethyl) isocyanurate, tris(2-acryloxyethyl) isocyanurate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, ethoxylated pentaerythritol Dimethylmethyl (meth)acrylate, ethoxylated pentaerythritol tetra(meth)acrylate, ditrimethylolpropane tetra(meth)acrylate, ethoxylated polyglycerin tetra(meth)acrylate, dipentaerythritol penta(meth)acrylate, ethoxylated dipentaerythritol penta(meth)acrylate, polyethylene glycol modified polyglycerin penta(meth)acrylate, dipentaerythritol hexa(meth)acrylate, ethoxylated dipentaerythritol hexa(meth)acrylate,Examples include polyethylene glycol-modified polyglycerin hexa(meth)acrylate. These may be used alone or in combination of two or more. Component (A): The polyfunctional (meth)acrylate compound preferably contains one or more compounds selected from the group consisting of the polyfunctional (meth)acrylate compounds exemplified above. In particular, from the viewpoint of achieving both the adhesive strength of the cured product and the degradability of the cured product, it is preferable that component (A): The polyfunctional (meth)acrylate compound contains one or more compounds selected from the group consisting of polyethylene glycol di(meth)acrylate, polyethylene glycol-modified polyglycerin hepta(meth)acrylate, and polyethylene glycol-modified polyglycerin hexa(meth)acrylate, more preferably that component (A): The polyfunctional (meth)acrylate compound contains one or more compounds selected from the group consisting of polyethylene glycol diacrylate and polyethylene glycol-modified polyglycerin hexaacrylate, and even more preferably that component (A): The polyfunctional (meth)acrylate compound contains polyethylene glycol diacrylate. For example, component (A): the polyfunctional (meth)acrylate compound may be polyethylene glycol diacrylate and / or polyethylene glycol-modified polyglycerin hexaacrylate. For example, component (A): the polyfunctional (meth)acrylate compound may be polyethylene glycol diacrylate and polyethylene glycol-modified polyglycerin hexaacrylate. For example, component (A): the polyfunctional (meth)acrylate compound may or may not contain triethylene glycol di(meth)acrylate. For example, component (A): the polyfunctional (meth)acrylate compound may or may not contain tripropylene glycol di(meth)acrylate.

[0023] Commercially available polyfunctional (meth)acrylate compounds are not particularly limited. Examples of commercially available polyfunctional (meth)acrylate compounds include Light Acrylate® 9EG-A, 14EG-A, TMP-A, DCP-A (all manufactured by Kyoeisha Chemical Co., Ltd.), NK Ester A-200, A-400, A-600, A-1000, A-DCP, A-TMPT, SA-TE6, SA-TE60 (all manufactured by Sakamoto Pharmaceutical Co., Ltd.), and others.

[0024] The number of (meth)acryloyl groups in the polyfunctional (meth)acrylate compound is preferably 2 to 10, more preferably 2 to 8, and even more preferably 2 to 6. The number of (meth)acryloyloxy groups in the polyfunctional (meth)acrylate compound is preferably 2 to 10, more preferably 2 to 8, and even more preferably 2 to 6. From the viewpoint of achieving both excellent adhesive strength and excellent decomposition properties of the cured product, component (A) preferably contains a difunctional (meth)acrylate compound and / or a trifunctional or higher (meth)acrylate compound, more preferably contains both a difunctional (meth)acrylate compound and a trifunctional or higher (meth)acrylate compound, and even more preferably contains a difunctional (meth)acrylate compound and a hexafunctional (meth)acrylate compound. (A) When component contains both a difunctional (meth)acrylate compound and a trifunctional or higher (meth)acrylate compound, from the viewpoint of achieving both excellent adhesive strength and excellent degradability of the cured product, the mixing ratio of the difunctional (meth)acrylate compound and the trifunctional or higher (meth)acrylate compound is preferably, in molar ratio, difunctional (meth)acrylate compound:trifunctional or higher (meth)acrylate compound = 9:1 to 1:9, more preferably difunctional (meth)acrylate compound:trifunctional or higher (meth)acrylate compound = 5:5 to 1:9, even more preferably difunctional (meth)acrylate compound:trifunctional or higher (meth)acrylate compound = 5:5 to 3:7, and particularly preferably difunctional (meth)acrylate compound:trifunctional or higher (meth)acrylate compound = greater than 5:less than 5 to 4:6. When two or more types of difunctional (meth)acrylate compounds are used, the amount of the difunctional (meth)acrylate compound represents the total amount of these. When two or more (meth)acrylate compounds with three or more functions are used, the amount of these (meth)acrylate compounds represents their total amount.

[0025] (A) Component preferably contains a trifunctional or more (meth)acrylate compound. Including a trifunctional or more (meth)acrylate compound enables three-dimensional crosslinking, resulting in superior adhesive strength in the cured product.

[0026] The content of component (A) in the first liquid is not particularly limited. The content of component (A) in the first liquid is preferably 10% by mass or more and 95% by mass or less, more preferably 30% by mass or more and 90% by mass or less, still more preferably 50% by mass or more and 80% by mass or less, and particularly preferably 60% by mass or more and 70% by mass or less, based on the total mass of the first liquid. When two or more kinds are used as component (A), the amount of component (A) represents the total amount thereof.

[0027] It is preferable that the second liquid does not contain component (A).

[0028] The mass of component (A) relative to the total mass of the first liquid and the second liquid is not particularly limited. The proportion of the mass of component (A) relative to the total mass of the first liquid and the second liquid is preferably 10% by mass or more and 90% by mass or less, more preferably 20% by mass or more and 70% by mass or less, still more preferably 30% by mass or more and 60% by mass or less, and particularly preferably 40% by mass or more and 45.5% by mass or less, based on the total mass of the first liquid and the second liquid. When two or more kinds are used as component (A), the amount of component (A) represents the total amount thereof.

[0029] [Component (B)] Component (B) is a polyhydrazide compound. In this specification, a polyhydrazide compound is a compound having two or more H ２ NHNC(=O)- structures in the molecule. Component (B) is solid at 25°C. That is, component (B) is a polyhydrazide compound that is solid at 25°C, that is, it can be said to represent a compound that is solid at 25°C and has two or more H ２ NHNC(=O)- structures in the molecule. The number of H ２ NHNC(=O)- structures in the molecule of the polyhydrazide compound is preferably 2 or more and 5 or less, more preferably 2 or more and 3 or less, and still more preferably 2. As component (B), from the viewpoint of exhibiting high adhesive strength of the cured product and high decomposability of the cured product, a dihydrazide compound (that is, H ２Compounds having two NHNC(=O)- structures in the molecule are preferred. Therefore, it is preferable that component (B) contains a dihydrazide compound. The (meth)acryloyl group in component (A) and the hydrazide structure in component (B) form a crosslink, thereby forming a cured product. The -NH-NH- structure formed by the cured crosslink is converted by the action of an oxidizing agent to N ２ The compound is easily decomposed and the adherends can be separated by the desorption of the compound as a gas and the cleavage breaking. (B) Component: The polyhydrazide compound that is solid at 25°C is not particularly limited. (B) Component: Examples of polyhydrazide compounds that are solid at 25°C include adipic acid dihydrazide, sebacate acid dihydrazide, dodecanediohydrazide (also known as dodecanediic acid dihydrazide), isophthalic acid dihydrazide, malonic acid dihydrazide, succinic acid dihydrazide, trimesic acid trihydrazide, and 1,2,4-butanetricarboxylic acid trihydrazide. The molecule contains an aromatic ring and / or -(CH ２ ) ｎ Dihydrazide compounds having a repeating unit of - (n = integer from 4 to 10) are more preferred, and dihydrazide compounds having an aromatic ring are even more preferred. These may be used alone or in combination of two or more. Component (B): The polyhydrazide compound that is solid at 25°C preferably contains one or more selected from the group consisting of the compounds exemplified above. Component (B): The polyhydrazide compound that is solid at 25°C preferably has an aromatic ring and / or - (CH) in its molecule. ２ ) ｎ The dihydrazide compound may have a repeating unit of - (n = integer from 4 to 10), or it may have an aromatic ring, or it may be an isophthalic acid dihydrazide. From the viewpoint of exhibiting curability and high adhesive strength, the melting point of component (B) is preferably 100 to 300°C, more preferably 150 to 280°C, and even more preferably 200 to 250°C. The melting point is a value determined by the DSC measurement method. In this specification, the melting point represents the melting point at 1 atm.

[0030] (B) Commercially available products of component (B) are not particularly limited. Examples of commercially available products of component (B) include ADH, SDH, DDH, IDH, and SAH (all manufactured by Otsuka Chemical Co., Ltd.).

[0031] The amount of component (B) contained in the two-component curable resin composition according to this embodiment is not particularly limited. For example, the two-component curable resin composition according to this embodiment may contain 5 to 80 parts by mass of component (B) per 100 parts by mass of component (A). For example, it is preferable that the two-component curable resin composition according to this embodiment contains 10 to 150 parts by mass of component (B) per 100 parts by mass of component (A). For example, it is more preferable that the two-component curable resin composition according to this embodiment contains 15 to 100 parts by mass of component (B) per 100 parts by mass of component (A). For example, it is even more preferable that the two-component curable resin composition according to this embodiment contains 20 to 50 parts by mass of component (B) per 100 parts by mass of component (A). For example, it is particularly preferable that the two-component curable resin composition according to this embodiment contains 30 to 45 parts by mass of component (B) per 100 parts by mass of component (A). If the amount of component (B) contained in the two-component curable resin composition is 10 to 150 parts by mass per 100 parts by mass of component (A) contained in the two-component curable resin composition, a two-component curable resin composition can be obtained that can form a cured product with excellent adhesive strength and degradability. When two or more types of component (A) are used, the amount of component (A) represents the total amount of these components. When two or more types of component (B) are used, the amount of component (B) represents the total amount of these components.

[0032] The first liquid preferably does not contain component (B).

[0033] The content of component (B) in the second liquid is not particularly limited. Preferably, the content of component (B) in the second liquid is 10% by mass or more and 90% by mass or less, more preferably 20% by mass or more and 80% by mass or less, even more preferably 30% by mass or more and 60% by mass or less, and particularly preferably 25% by mass or more and 45% by mass or less, based on the total mass of the second liquid. When two or more types of component (B) are used, the amount of component (B) represents the sum of these amounts.

[0034] [(C) Component] The (C) component is a solvent for dissolving the (B) component or a dispersion medium for dispersing the (B) component. The (C) component is liquid at 25°C. That is, the (C) component is a liquid at 25°C and is a solvent for dissolving the (B) component, or is a liquid at 25°C and is a dispersion medium for dispersing the (B) component. When the first liquid and the second liquid are mixed by completely dissolving the (B) component in the (C) component or uniformly dispersing the (B) component in the (C) component, better curability can be exhibited, and a cured product with higher adhesive strength and better decomposability can be obtained. Since better curability and higher adhesive strength in the cured product are exhibited, the (C) component is preferably a solvent for dissolving the (B) component.

[0035] The viscosity of the (C) component (viscosity at 25°C) is preferably more than 0 Pa·s and 100 Pa·s or less. The viscosity of the (C) component is more preferably 1 to 10,000 mPa·s, further preferably 5 to 5,000 mPa·s, further preferably 50 to 2,000 mPa·s, and particularly preferably 70 to 1,500 mPa·s. The viscosity of the (C) component may be 900 to 1,200 mPa·s. When the viscosity of the (C) component is within the above viscosity range, an increase in the viscosity of the liquid agent after dissolving or dispersing the (B) component is more suppressed, and the workability during two-component mixing is more excellent. The above viscosity is the viscosity measured by an E-type viscometer or a B-type viscometer at 25°C and 1 atm. The (C) component may, for example, have a viscosity measured by an E-type viscometer within the above range at 25°C and 1 atm.

[0036] The amount of component (C) contained in the two-component curable resin composition according to this embodiment is not particularly limited. The two-component curable resin composition according to this embodiment preferably contains 10 to 200 parts by mass of component (C) with respect to 100 parts by mass of component (A). The two-component curable resin composition according to this embodiment is more preferably contains 15 to 100 parts by mass of component (C) with respect to 100 parts by mass of component (A). The two-component curable resin composition according to this embodiment is even more preferably contains 20 to 50 parts by mass of component (C) with respect to 100 parts by mass of component (A). The two-component curable resin composition according to this embodiment is particularly preferably contains 37 to 45 parts by mass of component (C) with respect to 100 parts by mass of component (A). When the two-component curable resin composition according to this embodiment contains 10 to 200 parts by mass of component (C) with respect to 100 parts by mass of component (A), a two-component curable resin composition capable of forming a cured product excellent in adhesion strength and decomposability can be obtained. When two or more kinds are used as component (A), the amount of component (A) represents the total amount thereof. When two or more kinds are used as component (C), the amount of component (C) represents the total amount thereof.

[0037] In the two-component curable resin composition according to this embodiment, the mixing mass ratio of component (B) and component (C) is not particularly limited. In the two-component curable resin composition according to this embodiment, the mixing mass ratio of component (B) and component (C) ((B) component : (C) component) is preferably (B) component : (C) component = 1 : 0.5 to 1 : 3, more preferably (B) component : (C) component = 1 : 0.7 to 1 : 2, even more preferably (B) component : (C) component = 1 : 0.9 to 1 : 1.6, and particularly preferably (B) component : (C) component = 1 : 1.0 to 1 : 1.2. If the mixing mass ratio of component (B) and component (C) in the two-component curable resin composition according to this embodiment is (B) component : (C) component = 1 : 0.5 to 1 : 3, component (B) can be more sufficiently dissolved and / or dispersed, and the decomposability of the cured product can be maintained better. When two or more kinds are used as component (B), the amount of component (B) represents the total amount thereof. When two or more kinds are used as component (C), the amount of component (C) represents the total amount thereof.

[0038] The first liquid may or may not contain component (C), but it is preferable that the first liquid does not contain component (C).

[0039] The content of component (C) in the second liquid is not particularly limited. Preferably, the content of component (C) in the second liquid is 10% by mass or more and 90% by mass or less, more preferably 40% by mass or more and 80% by mass or less, even more preferably 45% by mass or more and 60% by mass or less, and particularly preferably 50% by mass or more and 55% by mass or less, based on the total mass of the second liquid. When two or more types of component (C) are used, the amount of component (C) represents the sum of these amounts.

[0040] As component (C), it is preferable to use an amine compound as component (C1) and / or a plasticizer as component (C2). Therefore, it is preferable that component (C) is an amine compound as component (C1) and / or a plasticizer as component (C2). When an amine compound is used as component (C1), the amine compound and component (A) react faster than component (B) to form a crosslinked structure, which has the advantage that the pot life when mixing the two-component curable resin composition can be adjusted by selecting the amine compound. On the other hand, by using a plasticizer as component (C2) which does not participate in the reaction, a sufficient pot life can be ensured. In the case of a plasticizer as component (C2), it is preferable that the molecular weight is 250 or more, as there is a possibility of outgassing if it is not incorporated into the crosslinking. Molecular weight is the sum of atomic weights. The molecular weight of component (C2) may be, for example, 250 or more and less than 1000, for example, 250 or more and 750 or less, or for example, 300 or more and 500 or less.

[0041] (C1) Component: The amine compound is not particularly limited. The (C1) component is a primary amino group (-NH ２ ) and / or secondary amino group (-NHR １ ;R １It is preferable that the amine compound has an organic group. The number of amino groups (preferably primary amino groups and / or secondary amino groups) in the amine compound is not particularly limited. When two or more types of amino groups are used, the number of amino groups in the amine compound represents the total amount of these groups. The number of amino groups in the molecule of the amine compound is not particular, but may be 1 to 5, 1 to 3, 1 to 2, or 1. The amine compound may be, for example, a monoamine having one amino group, a diamine having two amino groups, or a polyamine having three or more amino groups. The amine compound may also be a compound (oligomer or polymer) having multiple repeating units of a specific molecular structure. Component (C1) is a primary amino group (-NH ２ It is particularly preferable that the (C1) component has (meth)acryloyl groups. In component (C1), the reaction between one hydrogen of the primary amino group and the (meth)acryloyl group is more likely to occur, while the reaction between the secondary amino group and the (meth)acryloyl group may be less likely to occur. Also, the reaction between the primary amino group of (C1) and the (meth)acryloyl group is faster than the reaction between the hydrazide of component (B) and the (meth)acryloyl group. Therefore, in order to form a structure that can be decomposed by an oxidizing agent, a (meth)acryloyl group that reacts with the hydrazide of component (B) is necessary, and it is preferable that the total number of amino groups (preferably primary amino groups) in component (C1) is less than the total number of (meth)acryloyl groups in component (A).

[0042] Component (C1): The skeletal structure of the amine compound is not particularly limited. Examples of skeletal structures of amine compounds include aliphatic skeletons, alicyclic skeletons, aromatic skeletons, polyether skeletons, polyester skeletons, polyamine skeletons, and skeletons consisting of two or more combinations of these (for example, skeletons in which two or more of these skeletons are linked via ether groups or ester groups). Preferably, the skeletal structure of the amine compound includes at least one skeleton selected from the group consisting of the exemplified skeletons above. The aliphatic structure (aliphatic skeleton) may be linear or branched. Component (C1) may be an aliphatic amine having an aliphatic skeleton. Component (C1) may be an alicyclic amine having an alicyclic skeleton, or an alicyclic amine having both an aliphatic and an alicyclic skeleton. It may be an aromatic amine having an aromatic skeleton, or an aromatic amine having both an aliphatic and an aromatic skeleton, or an aromatic amine having both an alicyclic and an aromatic skeleton, or an aromatic amine having both an aliphatic, an alicyclic and an aromatic skeleton. If the amine compound is an oligomer or polymer, the repeating unit may be an aliphatic amine having an aliphatic skeleton. If the amine compound is an oligomer or polymer, it may be an alicyclic amine having at least one alicyclic group in the molecule, or an alicyclic amine whose repeating units have an alicyclic skeleton. If the amine compound is an oligomer or polymer, it may be an aromatic amine having at least one aromatic group in the molecule, or an aromatic amine whose repeating units have an aromatic skeleton. Aliphatic amines do not have alicyclic groups in the molecule and do not have aromatic groups. Alicyclic amines do not have aromatic groups in the molecule. If the amine compound is an aliphatic amine, the aliphatic structure (aliphatic skeleton) may be linear or branched, and the aliphatic structure (aliphatic skeleton) may be saturated or unsaturated.

[0043] The (C1) component is not particularly limited. Examples of the (C1) component include cardanol-modified amines obtained from cashew nut shells (amines modified with cardanol obtained from cashew nut shells and / or its derivatives; also referred to herein simply as "cardanol-modified amines"), polyaminoamides, tetraethylenepentamine, N-aminoethylpiperazine, bis(aminopropyl)piperazine, diethylenetriamine, triethylenetetramine, 4,7,10-trioxatridecane-1,13-diamine, octahydro-4,7-methano-1H-indendimethylamine, bicyclo[2.2.1]heptanebis(methylamine), meta-xylenediamine, isophoronediamine, cyclohexanediamine, trimethylolpropanepoly(oxypropylene)triamine, etc. These may be used alone or in combination of two or more. The (C1) component: The amine compound preferably contains one or more selected from the group consisting of the amine compounds exemplified above. Component (C1) may be at least one compound selected from the group consisting of cardanol-modified amine, polyaminoamide, triethylenetetramine, and trimethylolpropanepoly(oxypropylene)triamine, or it may be at least one compound selected from the group consisting of cardanol-modified amine, polyaminoamide, and trimethylolpropanepoly(oxypropylene)triamine, or it may be at least one compound selected from the group consisting of cardanol-modified amine and trimethylolpropanepoly(oxypropylene)triamine, or it may be cardanol-modified amine. It is preferable to include a cardanol-modified amine having a viscosity of 900 to 1200 mPa·s at 25°C, and more preferably a cardanol-modified amine having a viscosity of 900 to 1200 mPa·s at 25°C. The method and conditions for measuring viscosity are the same as those described for the viscosity of component (C) above.

[0044] The commercially available products of component (C1) are not particularly limited. Examples of commercially available products of component (C1) include Cardolite NX-5454, Cardolite LITE3060 (both manufactured by Tomoe Engineering Co., Ltd.), Jeffermin T-403 (manufactured by Huntsman Corporation), Tomid® 235R (manufactured by T&K TOKA Corporation), ThreeBond 2103 (manufactured by ThreeBond Corporation), and the like.

[0045] (C2) Component: The plasticizer is a compound that does not have functional groups that react with components (A) and (B). Examples of component (C2) include dibutyl phthalate, diheptyl phthalate, di(2-ethylhexyl) phthalate, butyl benzyl phthalate, butyl oleate, diethylene glycol dibenzoate, triethylene glycol dibenzoate, pentaerythritol ester, polyethylene glycol, polypropylene glycol, polytetramethylene glycol, plasticizers that are cardanol-modified compounds obtained from cashew nut shells (plasticizers that are compounds modified with cardanol obtained from cashew nut shells and / or its derivatives; hereinafter also simply referred to as "cardanol-modified plasticizers"), polyester-based plasticizers obtained from dibasic acids and dihydric alcohols, etc. These may be used alone or in combination of two or more. The dibasic acid used to obtain a polyester-based plasticizer from a dibasic acid and a dihydric alcohol is not particularly limited, but examples include sebacic acid, adipic acid, azelaic acid, and phthalic acid. These may be used alone or in combination of two or more. The dihydric alcohol used to obtain a polyester-based plasticizer from a dibasic acid and a dihydric alcohol is not particularly limited, but examples include ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol, and dipropylene glycol. These may be used alone or in combination of two or more. Component (C2): The plasticizer preferably contains one or more selected from the group consisting of the plasticizers exemplified above. Component (C2) preferably contains a cardanol-modified plasticizer, and more preferably a cardanol-modified plasticizer.

[0046] The commercially available products of component (C2) are not particularly limited. Examples of commercially available products of component (C2) include Cardolite LITE2020 (manufactured by Tomoe Engineering Co., Ltd.).

[0047] [Component (D)] The two-component curable resin composition according to this embodiment preferably further contains a filler as component (D). The filler is not particularly limited. Examples of fillers include inorganic fillers and organic fillers. By including component (D), higher adhesive strength of the cured product can be achieved. Component (D) may be included in either the first liquid or the second liquid, or in both the first liquid and the second liquid. Since the viscosity of the second liquid tends to increase due to the dissolution of component (B), depending on the combination of the first and second liquids, it cannot be said that there is absolutely no possibility that a viscosity difference will occur between the first liquid and the second liquid, reducing workability when mixing the two liquids. From the viewpoint of further reducing this possibility, it is particularly preferable to include component (D) in the first liquid. The inorganic filler is not particularly limited. Examples of inorganic fillers include powders of minerals, etc. Specific examples of mineral powders that can be used as inorganic fillers include glass powder, silica powder, alumina powder, mica powder, ceramic powder, silicone rubber powder, calcium carbonate powder, calcium oxide powder, aluminum nitride powder, carbon powder, kaolin clay powder, wollastonite powder, and aluminum powder. Organic fillers are not particularly limited as long as they are powders of organic matter. Examples of organic fillers include powders of organic matter composed of rubber, elastomers, plastics and / or polymers (or copolymers). Organic fillers may also be organic fillers having a multilayer structure such as a core-shell type. Specific examples of organic fillers include acrylic fillers made of polymers or copolymers of acrylic acid esters and / or (meth)acrylic acid esters, styrene fillers made of polymers or copolymers of styrene compounds, and urethane fillers made of polymers or copolymers having urethane bonds. The shape of the filler is not particularly limited. Examples of filler shapes include spherical and needle-shaped. These fillers may be used individually or mixed in groups of two or more. Component (D) preferably contains one or more selected from the group consisting of the fillers exemplified above.In particular, from the viewpoint of further improving the adhesive strength of the cured product without significantly, almost or completely reducing the degradability of the cured product, it is preferable that component (D) includes at least one selected from the group consisting of silica powder, calcium carbonate powder, and acrylic filler.

[0048] The commercially available products of ingredient (D) are not particularly limited. Examples of commercially available products of ingredient (D) include Aerosil 200 (manufactured by Nippon Aerosil Co., Ltd.), Whiten B (manufactured by Shiraishi Calcium Co., Ltd.), and Artpearl® G400T (manufactured by Negami Kogyo Co., Ltd.).

[0049] Component (D) preferably consists of two or more fillers. Component (D) is more preferably two or more inorganic fillers, or a combination of one or more inorganic fillers and one or more organic fillers. Component (D) is even more preferably a combination of one or more inorganic fillers and one or more organic fillers. For example, component (D) is preferably silica powder and calcium carbonate powder, or at least one selected from the group consisting of silica powder and calcium carbonate powder, and an acrylic filler. For example, component (D) is more preferably a combination of at least one selected from the group consisting of silica powder and calcium carbonate powder, and an acrylic filler. For example, component (D) is even more preferably silica powder and an acrylic filler. When component (D) contains one or more inorganic fillers and one or more organic fillers, the mass ratio of the inorganic filler content to the organic filler content in the two-component curable resin composition according to this embodiment is not particularly limited, but is preferably inorganic filler:organic filler = 1:99 to 50:50, more preferably inorganic filler:organic filler = 3:97 to 25:75, and even more preferably 5:95 to 15:85. When two or more organic fillers are used, the amount of organic fillers represents the total amount of these. When two or more inorganic fillers are used, the amount of inorganic fillers represents the total amount of these.

[0050] When the two-component curable resin composition according to this embodiment contains component (D), the amount of component (D) is not particularly limited. The two-component curable resin composition according to this embodiment preferably contains component (D) in an amount of 1 to 120 parts by mass per 100 parts by mass of component (A). That is, the content of component (D) in the two-component curable resin composition according to this embodiment is preferably 1 to 120 parts by mass per 100 parts by mass of component (A). Furthermore, the content of component (D) in the two-component curable resin composition according to this embodiment is more preferably 5 to 100 parts by mass per 100 parts by mass of component (A), and even more preferably 20 to 80 parts by mass. By having a content of component (D) in the two-component curable resin composition according to this embodiment of 1 to 120 parts by mass per 100 parts by mass of component (A), the adhesive strength of the cured product can be further improved without significantly, almost, or completely reducing the degradability of the cured product. When two or more types of component (A) are used, the amount of component (A) represents the total amount of these components. If two or more components (D) are used, the amount of component (D) represents the sum of these amounts.

[0051] From the viewpoint of reducing the viscosity difference between the first and second liquids and improving workability, it is preferable that component (D) be included in the first liquid. When component (D) is included in the first liquid, the content of component (D) in the first liquid is preferably 5 to 90% by mass, more preferably 10 to 60% by mass, and even more preferably 20 to 50% by mass, based on 100% by mass of the first liquid. That is, when component (D) is included in the first liquid, the content of component (D) in the first liquid is preferably 5 to 90% by mass, more preferably 10 to 60% by mass, and even more preferably 20 to 50% by mass, based on the total mass of the first liquid. By having a content of component (D) of 5 to 90% by mass in 100% by mass of the first liquid, the adhesive strength of the cured product can be further improved without significantly reducing, almost reducing, or not reducing the decompositionability of the cured product. When two or more types of component (D) are used, the amount of component (D) represents the total amount of these components.

[0052] The second liquid may or may not contain component (D), but it is preferable that the second liquid does not contain component (D).

[0053] [Component (E)] The two-component curable resin composition according to this embodiment may further contain a monofunctional (meth)acrylate compound as component (E). The monofunctional (meth)acrylate compound is not particularly limited. Examples of monofunctional (meth)acrylate compounds include ethyl (meth)acrylate, n-butyl (meth)acrylate, tert-butyl (meth)acrylate, isobutyl methacrylate, 2-ethylhexyl (meth)acrylate, isodecyl (meth)acrylate, butoxydiethylene glycol (meth)acrylate, methoxypolyethylene glycol (meth)acrylate, lauryl (meth)acrylate, stearyl (meth)acrylate, tetrahydrofurfuryl (meth)acrylate, caprolactone-modified tetrahydrofurfuryl (meth)acrylate, cyclohexyl (meth)acrylate, dicyclopentanyl (meth)acrylate, dicyclopentenyl (meth)acrylate, dicyclopentenyloxy (meth)acrylate, isobornyl (meth)acrylate, adamantyl (meth)acrylate, benzyl (meth)acrylate, and phenyl (meth) Examples include acrylates, phenoxyethyl (meth)acrylate, phenoxydiethylene glycol (meth)acrylate, phenoxytetraethylene glycol (meth)acrylate, nonylphenoxyethyl (meth)acrylate, butoxyethyl (meth)acrylate, 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate, glycerol (meth)acrylate, trifluoroethyl (meth)acrylate, (meth)acryloxyoxyethyl acid phosphate, 2-hydroxyethyl (meth)acrylic acid phosphate, morpholinoethyl (meth)acrylate, dimethylaminoethyl (meth)acrylate, diethylaminoethyl (meth)acrylate, N,N-dimethylaminoethyl (meth)acrylate, and N,N-dimethylaminopropyl (meth)acrylate. Examples of monofunctional (meth)acrylate compounds include monofunctional (meth)acrylate compounds having an acidic group.Examples of monofunctional (meth)acrylate compounds having an acidic group include (meth)acrylate compounds having a carboxylic acid and (meth)acrylate compounds having a phosphoric acid. Examples of (meth)acrylate compounds having a carboxylic acid include, but are not limited to, (meth)acrylic acid, 3-(meth)acryloyloxypropyl succinic acid, 4-(meth)acryloyloxybutyl succinic acid, 2-(meth)acryloyloxyethyl maleic acid, 3-(meth)acryloyloxypropyl maleic acid, 4-(meth)acryloyloxybutyl maleic acid, 2-(meth)acryloyloxyethyl hexahydrophthalic acid, 3-(meth)acryloyloxypropyl hexahydrophthalic acid, 4-(meth)acryloyloxybutyl hexahydrophthalic acid, 2-(meth)acryloyloxyethyl phthalic acid, 3-(meth)acryloyloxypropyl phthalic acid, and 4-(meth)acryloyloxybutyl phthalic acid. Examples of (meth)acrylate compounds having a phosphate group include, but are not limited to, 2-hydroxymethyl (meth)acrylate acid phosphate, 2-hydroxyethyl (meth)acrylate acid phosphate, and 2-hydroxypropyl (meth)acrylate acid phosphate. Monofunctional (meth)acrylate compounds may be used alone or in combination of two or more. Component (E) preferably contains one or more selected from the group consisting of the monofunctional (meth)acrylate compounds exemplified above. (E) Component: The monofunctional (meth)acrylate compound preferably contains a (meth)acrylate compound having a phosphate group and / or a monofunctional (meth)acrylate compound having an acidic group, more preferably contains a (meth)acrylate compound having a phosphate group, even more preferably contains one or more selected from the group consisting of the (meth)acrylate compounds having phosphate groups exemplified above, even more preferably contains 2-hydroxyethyl (meth)acrylate acid phosphate, and particularly preferably contains 2-hydroxyethyl methacrylate acid phosphate.For example, the monofunctional (meth)acrylate compound is preferably a (meth)acrylate compound having a phosphate group, more preferably one or more selected from the group consisting of the (meth)acrylate compounds having a phosphate group exemplified above, even more preferably 2-hydroxyethyl (meth)acrylate acid phosphate, and particularly preferably 2-hydroxyethyl methacrylate acid phosphate.

[0054] When the two-component curable resin composition according to this embodiment contains component (E), the amount of component (E) is not particularly limited. However, from the viewpoint of further reducing the possibility of two-dimensional or three-dimensional crosslinking between component (A) and component (B) being hindered, the content of component (E) is preferably 0.2 to 10 parts by mass, and more preferably 0.5 to 5 parts by mass, per 100 parts by mass of component (A). When two or more types of component (A) are used, the amount of component (A) represents the total amount of these. When two or more types of component (E) are used, the amount of component (E) represents the total amount of these.

[0055] The first liquid may or may not contain component (E), but it is preferable that it contains component (E). When component (E) is contained in the first liquid, the content of component (E) in the first liquid is preferably 0.01 to 30% by mass, more preferably 0.1 to 10% by mass, and even more preferably 1 to 5% by mass, based on the total mass of the first liquid. When two or more types of component (E) are used, the amount of component (E) represents the sum of these amounts.

[0056] The second liquid may or may not contain component (E), but it is preferable that component (E) is not included in the second liquid, as component (E) may reduce the storage stability of the second liquid.

[0057] (E) Component: The commercial availability of monofunctional (meth)acrylate monomers is not particularly limited. Examples of commercially available products of component (E) include Light Acrylate® IBX-A (manufactured by Kyoeisha Chemical Co., Ltd.) and ACMO® (manufactured by KJ Chemicals Co., Ltd.). Examples of commercially available monofunctional (meth)acrylate monomers having a phosphate group include Light Ester P-1M (manufactured by Kyoeisha Chemical Co., Ltd.) and Kayama PM-1 (manufactured by Nippon Kayaku Co., Ltd.). These may be used alone or in combination of two or more.

[0058] [Optional Components] The two-component curable resin composition according to this embodiment may further contain additives such as colorants, silane coupling agents, leveling agents, and rheology control agents (one or more additives other than components (A) to (E) described above), to the extent that they do not impair the properties of the present invention. The two-component curable resin composition according to this embodiment may not contain additives other than components (A) to (E) described above.

[0059] The coloring agent is not particularly limited. Examples of coloring agents include inorganic pigments and organic pigments. Inorganic pigments are not particularly limited. Examples of inorganic pigments include titanium dioxide, ultramarine, red iron oxide, lithopone, lead, cadmium, iron, cobalt, hydrochloride salts, sulfates, etc. Organic pigments are not particularly limited. Examples of organic pigments include azo pigments, phthalocyanine pigments, quinacridone pigments, quinacridonequinone pigments, dioxazine pigments, anthrapyrimidine pigments, anthancerone pigments, indanthrone pigments, flavanthrone pigments, perylene pigments, perinone pigments, diketopyrrolopyrrole pigments, quinonaphthalone pigments, anthraquinone pigments, thioindigo pigments, benzimidazolon pigments, isoindoline pigments, carbon black, etc. The amount of coloring agent is preferably 0.01 to 30 parts by mass per 100 parts by mass of component (A).

[0060] Silane coupling agents are not particularly limited. Examples of silane coupling agents include vinyl group-containing silane coupling agents, (meth)acrylic group-containing silane coupling agents, amino group-containing silane coupling agents, γ-mercaptopropyltrimethoxysilane, γ-chloropropyltrimethoxysilane, etc. Vinyl group-containing silane coupling agents are not particularly limited. Examples of vinyl group-containing silane coupling agents include 3-acryloxypropyltrimethoxysilane, vinyltris(β-methoxyethoxy)silane, vinyltriethoxysilane, vinyltrimethoxysilane, etc. (Meth)acrylic group-containing silane coupling agents are not particularly limited. Examples of (meth)acrylic group-containing silane coupling agents include 3-methacryloxypropylmethyldimethoxysilane, 3-methacryloxypropylmethyldiethoxysilane, 3-methacryloxypropyldimethylmonomethoxysilane, 3-methacryloxypropyldimethylmonoethoxysilane, 3-acryloxypropylmethyldipropyloxysilane, 3-acryloxypropylmethyldimethoxysilane, 3-acryloxypropylmethyldiethoxysilane, 3-acryloxypropylmethyldipropyloxysilane, 3-acryloxypropyldimethylmonopropyloxysilane, 3-acryloxypropyldimethylmonomethoxysilane, 3-acryloxypropyldimethylmonoethoxysilane, 3-acryloxypropyldimethylmonopropyloxysilane, γ-methacryloxypropyltrimethoxysilane, etc. The amino group-containing silane coupling agent is not particularly limited. Examples of amino group-containing silane coupling agents include N-β-(aminoethyl)-γ-aminopropyltrimethoxysilane, γ-aminopropyltriethoxysilane, and N-phenyl-γ-aminopropyltrimethoxysilane. The silane coupling agents exemplified above may be used individually or in combination of two or more. The amount of silane coupling agent is preferably 0.1 to 20 parts by mass per 100 parts by mass of component (A). If the amount of silane coupling agent is 0.1 to 20 parts by mass per 100 parts by mass of component (A), the effect of the silane coupling agent can be obtained without impairing the properties of the present invention.

[0061] [Epoxy Compounds] The two-component curable resin composition according to this embodiment does not contain epoxy resin (also referred to as epoxy compound in this specification). In this specification, epoxy resin (epoxy compound) is a compound having one or more glycidyl groups in one molecule. If epoxy compound is included, the glycidyl group reacts with the hydrogen of the secondary amino group, so an -NH-NH- bond is not formed and the cured product may not decompose with an oxidizing agent. Therefore, it is undesirable for the two-component curable resin composition according to this embodiment to contain epoxy compound. Not containing epoxy compound (in this specification, when simply stated as "not containing epoxy compound," it means substantially not containing epoxy compound) means that the epoxy compound is less than 1% by mass of the total composition. The epoxy compound content in the two-component curable resin composition according to this embodiment (the total amount if two or more epoxy compounds are used) is less than 1% by mass of the total mass of the two-component curable resin composition according to this embodiment, preferably 0% by mass (lower limit 0% by mass). The fact that the epoxy compound content in the two-component curable resin composition according to this embodiment is 0% by mass relative to the total mass of the two-component curable resin composition according to this embodiment indicates that the two-component curable resin composition according to this embodiment contains no epoxy compound at all.

[0062] [Radical Initiators] The two-component curable resin composition according to this embodiment does not contain radical initiators. A radical initiator is a compound that generates radicals when exposed to light or heat. If a radical initiator is included, the (meth)acryloyl groups that polymerize with each other and react with the hydrazide will be eliminated, which may prevent the formation of an -NH-NH- bond and the cured product from being decomposed by an oxidizing agent. Therefore, it is undesirable for the two-component curable resin composition according to this embodiment to contain radical initiators. Not containing radical initiators (in this specification, when simply stated as "not containing radical initiators," it means substantially not containing radical initiators) means that the radical initiator is less than 0.5% by mass of the total composition. The amount of radical initiator in the two-component curable resin composition according to this embodiment (the total amount if two or more types of radical initiators are used) is less than 0.5% by mass of the total mass of the two-component curable resin composition according to this embodiment, and preferably 0% by mass (lower limit 0% by mass). The fact that the radical initiator content in the two-component curable resin composition according to this embodiment is 0% by mass relative to the total mass of the two-component curable resin composition according to this embodiment indicates that the two-component curable resin composition according to this embodiment contains no radical initiator at all.

[0063] [Viscosity] In the two-component curable resin composition according to this embodiment, the viscosity of the first liquid at a 25°C environment is not particularly limited, but is preferably 1 Pa·s or more and 2000 Pa·s or less, more preferably 1 Pa·s or more and 500 Pa·s or less, and even more preferably 1 Pa·s or more and 100 Pa·s or less. In the two-component curable resin composition according to this embodiment, the viscosity of the second liquid at a 25°C environment is not particularly limited, but is preferably 1 Pa·s or more and 2000 Pa·s or less, more preferably 1 Pa·s or more and 1700 Pa·s or less, and even more preferably 1 Pa·s or more and 1500 Pa·s or less. In the two-component curable resin composition according to this embodiment, the viscosity of the first liquid and the second liquid is measured at a shear speed of 10s using a cone-plate type rotational viscometer at a 25°C environment. －１ It can be measured with [this method].

[0064] [Method for Producing a Two-Component Curable Resin Composition] The method for producing the two-component curable resin composition according to this embodiment is not particularly limited. Preferably, the method for producing the two-component curable resin composition according to this embodiment includes preparing a first liquid containing component (A) above and not containing epoxy compounds and radical initiators, and a second liquid containing components (B) and (C) above and not containing epoxy compounds and radical initiators. Preferably, the method for producing the two-component curable resin composition according to this embodiment when in use (preparation method) includes mixing the first liquid containing component (A) above and not containing epoxy compounds and radical initiators, and the second liquid containing components (B) and (C) above and not containing epoxy compounds and radical initiators. The method for producing the first liquid is not particularly limited. The method for producing the second liquid is not particularly limited. The method for mixing the first liquid and the second liquid is not particularly limited.

[0065] [Method of Use of Two-Component Curable Resin Composition] The method of use of the two-component curable resin composition according to this embodiment is not particularly limited. Preferably, the method of use of the two-component curable resin composition according to this embodiment involves mixing a first liquid containing component (A) above and not containing epoxy compounds and radical initiators, and a second liquid containing components (B) and (C) above and not containing epoxy compounds and radical initiators. The method of mixing the first liquid and the second liquid is not particularly limited.

[0066] <Application Method, Cured Product, Laminate Containing the Cured Product, and Method for Disassembling the Laminate> The two-component curable resin composition according to the above embodiment hardens under arbitrary conditions after mixing (i.e., after mixing the first and second liquids) to form a cured product. The hardening method is not particularly limited. Examples of hardening methods include room temperature hardening and heat hardening. Furthermore, if the two-component curable resin composition according to the above embodiment contains component (C1), the two-component curable resin composition according to the above embodiment can be partially hardened at room temperature by mixing the two liquids (first liquid and second liquid), but hardening by heat may be necessary to form a degradable crosslink between component (B) and component (A). Since the obtained cured product decomposes easily at low temperatures with an oxidizing agent, the two-component curable resin composition according to the above embodiment itself can be used as an adhesive, sealant and / or coating agent, and the obtained cured product can be easily disassembled using an oxidizing agent.

[0067] Another aspect of the present invention relates to a cured product obtained by curing a two-component curable resin composition according to the above aspect. Another aspect of the present invention relates to a laminate comprising two adherends and a cured layer made of one or more cured products according to the above aspect that is in contact with one or both of the two adherends. Another aspect of the present invention relates to a laminate obtained by bonding two adherends together using a two-component curable resin composition according to the above aspect and curing the two-component curable resin composition. Another aspect of the present invention relates to a laminate obtained by bonding two adherends, each having a cured layer obtained by applying and curing a two-component curable resin composition according to the above aspect to at least one of the two adherends, using an adhesive other than the two-component curable resin composition and curing the adhesive.

[0068] When the two-component curable resin composition according to the above embodiment is used as an adhesive and / or sealant, a laminate that can be disassembled can be obtained by applying the two-component curable resin composition to one or both of two adherends, bonding the two adherends, each having a region on one or both of the adherends coated with the two-component curable resin composition, at least one of the adherends including the region on which the two-component curable resin composition is applied (bonding portion), and then curing the two-component curable resin composition. In other words, a preferred embodiment can also be said to relate to a laminate obtained by applying the two-component curable resin composition according to the above embodiment to one or both of two adherends, bonding the two adherends, each having a region on one or both of the adherends coated with the two-component curable resin composition, at least one of the adherends including the region on which the two-component curable resin composition is applied (bonding portion), and then curing the two-component curable resin composition.

[0069] When the two-component curable resin composition according to the above embodiment is used as a coating agent, a laminate that is easily disassembled can be obtained by applying the two-component curable resin composition to a substrate and curing the two-component curable resin composition.

[0070] [Application Method] The application method for the two-component curable resin composition according to the above embodiment is not particularly limited, but it is preferable to apply the two-component curable resin composition according to the above embodiment after mixing the first liquid and the second liquid. The method for applying the two-component curable resin composition according to the above embodiment to the adherend is the same as the method for applying known adhesives and sealants. For example, methods such as dispensing using an automatic dispenser, spraying, inkjet printing, screen printing, gravure printing, dipping, spin coating, or brush application can be used. It is preferable that the two-component curable resin composition according to the above embodiment is liquid at 25°C from the viewpoint of applicability.

[0071] [Curing Method] The curing method for the two-component curable resin composition according to the above embodiment is not particularly limited, however, it is preferable that the two-component curable resin composition according to the above embodiment forms a decomposable cured product upon curing. The curing method is not particularly limited. Examples of curing methods include room temperature curing and heat curing. When heat curing is performed, examples of heating devices include, but are not limited to, a hot air drying oven, a far-infrared heater, and a hot plate. When heat curing is performed, the heating temperature is not particularly limited. From the viewpoint of further developing the adhesive strength of the cured product, the heating temperature is preferably 100 to 200°C. When heat curing is performed, the heating time is preferably 0.1 seconds to 5 hours, more preferably 1 second to 3 hours, and even more preferably 5 seconds to 2 hours.

[0072] [Primer Applications] The two-component curable resin composition according to the above embodiment can be used as a primer for pretreatment of an adherend, thereby imparting decomposability to laminates that further use adhesives other than the two-component curable resin composition, sealants other than the two-component curable resin composition, and / or coating agents other than the two-component curable resin composition. In this specification, "primer" refers to a treatment liquid used for surface treatment of an adherend before applying an adhesive, sealant, and / or coating agent. In this specification, "primer treatment" refers to applying the two-component curable resin composition to an adherend and curing it before applying an adhesive, sealant, and / or coating agent. The curing method is not particularly limited. Examples of curing methods include room temperature curing and heat curing. When used as a primer, the two-component curable resin composition according to the above embodiment has the advantage of not being affected by the curing form of the adhesive, sealant, and / or coating agent. Various curing modes can be used for adhesives, sealants, and / or coatings, including, for example, moisture curing, anaerobic curing, heat curing, photocuring, two-component mixture curing, and solvent volatilization curing. However, the two-component curable resin composition according to the above embodiment can be used for adhesives with various curing modes, sealants with various curing modes, and / or coatings with various curing modes. For example, the two-component curable resin composition according to the above embodiment can be suitably used for moisture-curing, heat-curing, or photocuring adhesives, and / or moisture-curing, heat-curing, or photocuring adhesives.

[0073] When using the two-component curable resin composition according to the above embodiment as a primer, and using an adhesive other than the two-component curable resin composition and / or a sealant other than the two-component curable resin composition, a laminate with decomposability can be obtained by applying the two-component curable resin composition to one or both of the two adherends, curing it (primer treatment) to obtain a cured layer, and then applying the adhesive other than the two-component curable resin composition and / or the sealant other than the two-component curable resin composition on the obtained cured layer and curing it under any conditions. Note that when the two-component curable resin composition according to the above embodiment is used as a primer and one of the two adherends is primed, the adhesive other than the two-component curable resin composition and / or the sealant other than the two-component curable resin composition only needs to be in contact with the primer-treated surface (i.e., the layer of cured material obtained by curing the two-component curable resin composition (cured layer)). Two adherends may be bonded together by a method that includes applying an adhesive other than the two-component curable resin composition according to the above embodiment and / or a sealant according to the above embodiment onto a primer-treated surface and curing it, thereby bringing the adhesive other than the two-component curable resin composition and / or the sealant other than the two-component curable resin composition into contact with the primer-treated surface. Alternatively, an adherend without a primer and an adherend with a primer may be bonded together by a method that includes applying an adhesive other than the two-component curable resin composition according to the above embodiment and / or a sealant according to the above embodiment to an adherend that has not been coated with a primer (the two-component curable resin composition according to the above embodiment) and curing it, thereby bringing the adhesive other than the two-component curable resin composition and / or the sealant other than the two-component curable resin composition into contact with the primer-treated surface. A preferred embodiment may also be described as relating to a laminate in which at least one of two adherends has a cured layer obtained by applying and curing the two-component curable resin composition according to the above embodiment, the two adherends are bonded together with an adhesive such that the cured layer in at least one of the adherends is in contact with an adhesive other than the two-component curable resin composition, and the adhesive is cured.

[0074] When using the two-component curable resin composition according to the above embodiment as a primer and using a coating agent other than the two-component curable resin composition, a laminate with decomposability can be obtained by applying the two-component curable resin composition to one adherend, curing it under arbitrary conditions (primer treatment), applying the coating agent other than the two-component curable resin composition on the primer-treated surface, and curing the coating agent under arbitrary conditions.

[0075] [Method for dismantling laminates] A laminate using the two-component curable resin composition according to the above embodiment (a laminate according to the above embodiment) can be dismantled by contact with an oxidizing agent under any conditions. Another embodiment of the present invention also relates to a method for dismantling a laminate, wherein the laminate according to the above embodiment is dismantled by immersing it in an aqueous solution containing an oxidizing agent to decompose the cured product of the two-component curable resin composition. The preferred dismantling temperature is not particularly limited, but from a safety viewpoint, 5 to 70°C is preferred, 10 to 60°C is more preferred, and 20 to 50°C is even more preferred. The contact time with the oxidizing agent required for dismantling is not particularly limited, but 10 seconds to 24 hours is preferred, 1 minute to 24 hours is more preferred, and 30 minutes to 20 hours is even more preferred.

[0076] The oxidizing agent (the oxidizing agent used for dismantling the laminate) is not particularly limited. Examples of oxidizing agents include chlorine, bromine, hydrogen peroxide, or hypochlorous acid or its salts. In the contact step with the oxidizing agent, it is preferable to use an aqueous solution containing the oxidizing agent, and more preferably to use an aqueous solution containing at least one compound selected from the group consisting of the oxidizing agents exemplified above. From the viewpoint of versatility, it is preferable to use an aqueous solution of hypochlorite in the contact step with the oxidizing agent, and more preferably to use an aqueous solution of sodium hypochlorite in the contact step with the oxidizing agent. The content of the oxidizing agent (preferably hypochlorous acid, particularly preferably sodium hypochlorite) in the aqueous solution containing the oxidizing agent (preferably an aqueous solution of hypochlorite, particularly preferably an aqueous solution of sodium hypochlorite) is not particularly limited, but for example, it may be 1% by mass or more and 10% by mass or less based on the total mass of the aqueous solution containing the oxidizing agent (preferably an aqueous solution of hypochlorite, particularly preferably an aqueous solution of sodium hypochlorite).

[0077] [Adheren] The type (material) of adherend to which the two-component curable resin composition according to the above embodiment can be applied is not particularly limited. Examples of adherend types (materials) include metals, plastics, rubber, etc. Metals are not particularly limited. Examples of metals include iron, aluminum, stainless steel, nickel, zinc, magnesium, gold, silver, copper, titanium, etc. Plastics are not particularly limited. Examples of plastics include fiber-reinforced plastics (FRP), glass fiber reinforced plastics (GFRP), carbon fiber reinforced plastics (CFRP), polyacrylic, polyester, polyamide, acrylonitrile-butadiene-styrene copolymer (ABS), nylon 6,6-nylon, polycarbonate, polyacetal, polyethylene terephthalate, polybutylene terephthalate (PBT), polyphenylene sulfide, polyphenylene ether, polyether ether ketone, polyethylene, polypropylene, etc. Rubbers are not particularly limited. Examples of rubbers include nitrile rubber, urethane rubber, silicone rubber, EPDM, etc. Among these, metals are preferred. The reason for this is that, because metals generally exhibit strong adhesive strength, laminates formed with metal as the adherend are usually difficult to dismantle. However, by using the two-component curable resin composition according to the above embodiment, it becomes possible to easily dismantle them.

[0078] <Applications> The two-component curable resin composition according to the above embodiment can be used alone. Furthermore, the two-component curable resin composition according to the above embodiment can be used in combination with various adhesives that are not dependent on the curing form, such as epoxy resins, acrylic resins and / or modified silicone resins, various sealants that are not dependent on the curing form, such as epoxy resins, acrylic resins and / or modified silicone resins, and various coating agents that are not dependent on the curing form, such as epoxy resins, acrylic resins and / or modified silicone resins. For this reason, the two-component curable resin composition according to the above embodiment can be applied to a wide variety of applications. The specific applications to which it can be applied are not particularly limited. Examples of specific applications to which it can be applied include automotive applications, electronic materials applications, battery applications, optical component applications, and infrastructure applications. Applications in the automotive sector are not particularly limited. Examples of automotive applications include bonding, sealing, casting, and coating in switch parts, headlamps, engine internal components, electrical components, drive engines, brake oil tanks, body panels and / or windows, etc. Body panels are not particularly limited. Examples of body panels include front hoods, fenders, and doors. Applications in the field of electronic materials are not particularly limited. Examples in the field of electronic materials include bonding, sealing, casting, and coating in flat panel displays, video discs, CDs, DVDs, MDs, pickup lenses, and / or hard disks. Flat panel displays are not particularly limited. Examples of flat panel displays include liquid crystal displays, organic EL displays, light-emitting diode displays, and field emission displays. Applications in the battery field are not particularly limited. Examples in the battery field include bonding, sealing, and coating in lithium batteries, lithium-ion batteries, manganese batteries, alkaline batteries, fuel cells, silicon-based solar cells, dye-sensitized batteries, and / or organic solar cells. Applications in the optical components field are not particularly limited.Examples of applications in the field of optical components include bonding, sealing, and coating in optical fiber materials around optical switches and optical connectors, optical passive components, optical circuit components, and around optoelectronic integrated circuits. Applications in the field of optical equipment are not particularly limited. Examples of applications in the field of optical equipment include bonding, sealing, and coating in camera modules, lens materials, finder prisms, target prisms, finder covers, light-receiving sensor parts, photographic lenses, and projection lenses for projection televisions. Applications in the field of infrastructure are not particularly limited. Examples of applications in the field of infrastructure include adhesives, lining materials, sealing materials, and coating materials in gas pipes and / or water pipes.

[0079] The present invention will now be described in more detail with reference to examples, but the present invention is not limited to these examples. Furthermore, the first and second liquids before mixing will be simply referred to as "compositions," and the mixture of the first and second liquids will be referred to as a "two-component curable resin composition."

[0080] [Example 1, Comparative Example 1] The following components were prepared to prepare each composition.

[0081] (A) Ingredients: (a-1) Polyethylene glycol 400# diacrylate, trade name: Light Acrylate (registered trademark) 9EG-A (manufactured by Kyoeisha Chemical Co., Ltd.), ethylene oxide number: 9, molecular weight: 538; (a-2) Polyethylene glycol modified polyglycerin hexaacrylate, trade name: SA-TE6 (manufactured by Sakamoto Pharmaceutical Co., Ltd.), ethylene oxide number: 9, molecular weight: 1000; (a-3) Trimethylolpropane triacrylate, trade name: A-TMPT (manufactured by Shin Nakamura Chemical Co., Ltd.), molecular weight: 338; (B) Ingredients: (b-1) Isophthalic acid dihydrazide, trade name: IDH (manufactured by Otsuka Chemical Co., Ltd.), solid (25℃), melting point: 220℃; (C) Ingredients: (c1-1) Cardanol modified amine, trade name: Cardolite NX-5454 (Tomoe Kogyo Co., Ltd.), viscosity: 1000 mPa·s (25℃); (D) Components: (d-1) Hydrophilic fumed silica powder, product name: Aerosil 200 (manufactured by Nippon Aerosil Co., Ltd.): (d-2) Calcium carbonate powder, product name: Whiteon B (manufactured by Shiraishi Calcium Co., Ltd.).

[0082] The viscosity of component (C) at 25°C was measured using an E-type viscometer at 1 atm. Preferably, the viscosity of component (C) at 25°C is greater than 0 Pa·s and less than or equal to 100 Pa·s.

[0083] In Example 1, to prepare the first liquid, components (A) and (D) were weighed into a stirring vessel, stirred for 3 minutes in a rotary-orbiting stirrer, and degassed for 1 minute. To prepare the second liquid, components (B) and (C) were weighed into a stirring vessel, stirred for 3 minutes in a rotary-orbiting stirrer, and degassed for 1 minute. In Comparative Example 1, components (A), (B), and (D) were weighed into a stirring vessel, stirred for 3 minutes in a rotary-orbiting stirrer, and degassed for 1 minute. Detailed preparation amounts are shown in Table 1, and all values ​​for each component are expressed in parts by mass. In Table 1, blank spaces for each component indicate that that component was not used, and blank spaces for each liquid indicate that that liquid was not used. All tests were conducted at 25°C.

[0084] [Initial Viscosity] The composition of the first liquid of Example 1, the second liquid of Example 1, and the composition of Comparative Example 1 were measured at a shear speed of 10 s in a cone-plate type rotational viscometer at 25°C. －１ The measurement was performed using the following method. There are no particular restrictions on the initial viscosity, but from the viewpoint of workability, it is preferable that the initial viscosity be 1 Pa·s or more and 2000 Pa·s or less. Here, the results for the composition of Comparative Example 1 are shown in the First Liquid column. Measurement conditions: Cone rotor: 3° × R14, Rotation speed: 5 rpm, Measurement time: 3 minutes.

[0085] [Storage Stability] The first liquid of Example 1, the second liquid of Example 1, and the composition of Comparative Example 1 were sealed in 50 ml glass bottles and left to stand for one month at 40°C. After returning to room temperature, the viscosity at 25°C was measured in the same manner as above. Evaluation Criteria (Acceptance Criteria) ○: Viscosity is less than twice that of before storage (before the start of standing at 40°C); ×: Viscosity is more than twice that of before storage (before the start of standing at 40°C), or hardening progresses during the one month of standing at 40°C, making it impossible to measure the viscosity at 25°C after one month of standing at 40°C.

[0086] Table 1 shows the evaluation results for Example 1 and Comparative Example 1. In Table 1, a "-" next to each evaluation indicates that the evaluation was not performed.

[0087]

[0088] As shown in Table 1, the first liquid and the second liquid of Example 1 are suitable for use as the respective liquids in a two-component curable resin composition. On the other hand, in Comparative Example 1, which contains components (A) and (B) in a unified system, the composition of Comparative Example 1 is not suitable for use as the respective liquids in a two-component curable resin composition. As shown in Table 1, the compositions of the first liquid and the second liquid of Example 1 have excellent storage stability. On the other hand, the composition of Comparative Example 1, which contains components (A) and (B) in a unified system, has poor storage stability because the reaction between component (A) and component (B) proceeds gradually.

[0089] [Examples 2-9, Comparative Example 2] The following components were prepared to further prepare each composition.

[0090] (C) Components: (c1-2) Cardanol-modified amine, trade name: Cardolite LITE 3060 (Tomoe Engineering Co., Ltd.), viscosity: 850 mPa·s (25℃); (c1-3) Trimethylolpropane poly(oxypropylene)triamine, trade name: Jeffermin T-403 (manufactured by Huntsman Corporation), viscosity: 70.4 mPa·s (25℃); (c1-4) Polyaminoamide, trade name: Tomid® 235R (manufactured by T&K TOKA Corporation), viscosity: 3000 mPa·s (25℃); (c1-5) Triethylenetetramine, trade name: ThreeBond 2103 (manufactured by ThreeBond Corporation), viscosity: 20 mPa·s (25℃); (c2-1) Cardanol-modified plasticizer, trade name: Cardolite LITE2020 (Tomoe Kogyo Co., Ltd.), viscosity: 72.5 mPa·s (25℃), molecular weight: 344; (D) component: (d-3) Acrylic filler, trade name: Art Pearl (registered trademark) G400T (manufactured by Negami Kogyo Co., Ltd.); (E) component: (e-1) 2-hydroxyethyl methacrylate acid phosphate, trade name: Light Ester P-1M (manufactured by Kyoeisha Chemical Co., Ltd.).

[0091] The viscosity of component (C) at 25°C was measured using an E-type viscometer at 1 atm. Preferably, the viscosity of component (C) at 25°C is greater than 0 Pa·s and less than or equal to 100 Pa·s.

[0092] In Examples 2-9 and Comparative Example 2, the first liquid was prepared by weighing components (A), (D), and (E) into a stirring vessel, stirring for 3 minutes in a rotary-orbiting stirrer, and degassing for 1 minute. The second liquid was prepared by weighing components (B) and (C) into a stirring vessel, stirring for 3 minutes in a rotary-orbiting stirrer, and degassing for 1 minute. Detailed preparation amounts are shown in Table 2, with all values ​​for each component expressed in parts by mass. In Table 2, blank spaces next to each component indicate that that component was not used.

[0093] [Method for preparing a two-component curable resin composition] After preparing the first liquid composition and the second liquid composition separately, the first and second liquids were weighed into the same container and quickly stirred to obtain a predetermined mixing ratio (mass ratio shown in Table 2) to prepare a two-component curable resin composition.

[0094] [Shear Adhesion Strength (Initial)] For each of the two-component curable resin compositions of Examples 2 to 9 and Comparative Example 2, the two-component curable resin composition was applied to an aluminum plate (A1050P) measuring 25 mm wide x 100 mm long x 1 mm thick, using a spacer so that the overlap surface (overlapping surface of the two aluminum plates) was 25 mm x 10 mm and the coating thickness was 0.1 mm. The aluminum plate coated with the two-component curable resin composition was then bonded to another aluminum plate that was not coated with the two-component curable resin composition. The resulting test specimens (test specimens before heat treatment) were heated in a hot air drying oven at 170°C for 1 hour, then returned to room temperature to be used as shear adhesion strength measurement specimens. The maximum strength (MPa) of the shear adhesion strength measurement specimens was measured at 50 mm / min using a tensile testing machine, and the obtained maximum strength (MPa) was defined as the shear adhesion strength (initial). In this evaluation, the tensile test was performed using a Tensilon tensile testing machine manufactured by A&D Co., Ltd., by pulling each of the two aluminum plates in opposite directions using separate chucks. In this evaluation, a shear bond strength of 2 MPa or higher was considered acceptable.

[0095] [Shear Adhesion Strength (After Immersion)] A shear adhesion strength measurement specimen was prepared in the same manner as the evaluation of shear adhesion strength (initial). The test specimen (shear adhesion strength measurement specimen) was immersed in a 500 mL beaker containing 400 mL of 6% (6 by mass) sodium hypochlorite aqueous solution (Kitchen Hyter, manufactured by Kao Corporation) at 50°C for 16 hours in a constant temperature bath. The immersed test specimen (shear adhesion strength measurement specimen) was removed from the beaker and allowed to stand in a fume hood under a 55% RH atmosphere at 25°C for 12 hours to dry the test specimen (shear adhesion strength measurement specimen). The maximum strength (MPa) of the dried test specimen (shear adhesion strength measurement specimen) was measured at a tensile speed of 50 mm / min using a tensile testing machine (Tensilon, manufactured by A&D Co., Ltd.), and the obtained maximum strength (MPa) was defined as the shear adhesion strength (after immersion). In this evaluation, tensile tests were performed using a Tensilon tensile testing machine manufactured by A&D Co., Ltd., by pulling each of the two aluminum plates in opposite directions using separate chucks. Tests in which the test specimen (shear bond strength measurement specimen) detached during immersion or drying were recorded as 0.0 (MPa).

[0096] [Shear Bond Strength (Change Rate)] The change rate of shear bond strength (hereinafter also simply referred to as the change rate) was calculated using the following formula: Change Rate (%) = (Shear Bond Strength (after immersion) - Shear Bond Strength (initial)) / Shear Bond Strength (initial) × 100. In this evaluation, a strength reduction of -40% or less was considered acceptable, and a strength reduction of -50% or less was particularly preferred.

[0097] [Pot Life] For Examples 2-9 and Comparative Example 2, after preparing the two-component curable resin composition, the composition was left at 25°C and its state was visually inspected. The time until it became semi-cured was summarized in Table 2 as "Pot Life (minutes)". Here, "semi-cured" refers to the time until no liquid remains on the tip of a wooden stick when touched. "-" indicates that the composition remains liquid for 24 hours or more. The composition was observed continuously for 5 minutes after being left to stand, and then checked at 5-minute intervals thereafter.

[0098] The evaluation results for Examples 2 to 9 and Comparative Example 2 are shown in Table 2.

[0099]

[0100] As shown in Table 2, the two-component curable resin compositions of Examples 2 to 9, in which the first liquid contained component (A) and the second liquid contained components (B) and (C), showed good adhesive strength, and a significant decrease in the strength of the shear adhesive strength test specimens was observed after immersion in the oxidizing agent.

[0101] Example 2 was a two-component curable resin composition in which the content of component (B) was high relative to the content of component (C), resulting in excellent adhesive strength of the cured product, yet it was easily decomposed even after impregnation.

[0102] Compared to Example 2, Example 3 has a lower content of component (B) relative to the content of component (C), which is thought to result in a greater decrease in strength and a smaller absolute value of the shear adhesive strength (rate of change).

[0103] Regarding Example 4, it is considered that the initial strength was further reduced and desorption after impregnation occurred more easily because the content of component (B) was even lower than the content of component (C).

[0104] Examples 5 to 8 differ in the type of liquid amine compound used as component (C). These results demonstrate the advantage of being able to adjust the pot life depending on the selected liquid amine.

[0105] Furthermore, if it is not necessary to provide a pot life, a plasticizer can be selected as component (C) as in Example 9 to create a heat-curable resin composition.

[0106] In the case of Comparative Example 2, although it was a two-component curable resin composition that did not contain component (B), the initial adhesive strength was almost zero. Therefore, it is thought that swelling occurred due to the water content of the aqueous solution containing the oxidizing agent, causing the test piece to detach.

[0107] The two-component curable resin composition according to the preferred embodiment can form a cured product that has excellent adhesive strength and can be easily decomposed by an oxidizing agent. Furthermore, by pre-treating the adherend with the two-component curable resin composition according to the preferred embodiment as a primer, decomposability can be imparted when using various adhesives, sealants, and coatings. For these reasons, the above two-component curable resin composition is very useful in industry.

[0108] This application is based on Japanese Patent Application No. 2024-196499, filed on November 11, 2024, and its disclosures are referenced and incorporated as a whole.

Claims

1. A two-component curable resin composition comprising the following components (A) to (C), but not containing epoxy compounds or radical initiators, wherein the first liquid contains component (A), and the second liquid contains components (B) and (C): (A) component: polyfunctional (meth)acrylate compound (B) component: polyhydrazide compound that is solid at 25°C (C) component: a solvent that is liquid at 25°C and dissolves component (B), or a dispersion medium that is liquid at 25°C and disperses component (B).

2. The two-component curable resin composition according to claim 1, wherein component (C) is an amine compound as component (C1) and / or a plasticizer as component (C2).

3. The two-component curable resin compound according to claim 1 or 2, wherein the viscosity of component (C) is 1 to 10,000 mPa·s.

4. The two-component curable resin composition according to claim 1 or 2, comprising 5 to 80 parts by mass of component (B) per 100 parts by mass of component (A).

5. The two-component curable resin composition according to claim 1 or 2, wherein the mixed mass ratio of component (B) and component (C) is 1:0.5 to 1:

3.

6. The two-component curable resin composition according to claim 1 or 2, wherein component (A) comprises a bifunctional (meth)acrylate compound and / or a trifunctional or more (meth)acrylate compound.

7. The two-component curable resin composition according to claim 1 or 2, wherein component (A) comprises a polyfunctional (meth)acrylate compound with three or more functions.

8. The two-component curable resin composition according to claim 1 or 2, wherein component (B) comprises a dihydrazide compound.

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

10. A laminate comprising two adherends, one or both of which have a region on one or both of the two adherends to which the two-component curable resin composition described in claim 1 has been applied, and the two adherends are bonded together at a portion of at least one of the adherends that includes the region on which the two-component curable resin composition has been applied, and then the two-component curable resin composition is cured.

11. A laminate comprising two adherends, each having a cured layer obtained by applying the two-component curable resin composition described in claim 1 to at least one of the adherends and curing it, and the two adherends being bonded together with the adhesive such that the cured layer in at least one of the adherends is in contact with the adhesive other than the two-component curable resin composition, and the adhesive being cured.

12. A method for dismantling a laminate, comprising immersing the laminate according to claim 10 or 11 in an aqueous solution containing an oxidizing agent to decompose and dismantle the cured product of the two-component curable resin composition.

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