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

Abstract

Provided are: a resin composition which is capable of providing an adhesive having excellent heat resistance and moisture resistance; and a cured product obtained using the resin composition. Also provided are a laminate using the cured product, and a method for producing the laminate. A resin composition containing 1, 1-dicyanoethylene (A) and a polymerizable monomer (B) represented by general formula (I), the resin composition being characterized in that the content of the 1, 1-dicyanoethylene (A) in the total of the 1, 1-dicyanoethylene (A) and the polymerizable monomer (B) is 2.0-99.9 mass%. CHR1-CR2R3 (I)

Description

Technical Field

[0001] The present invention relates to a resin composition containing 1,1-dicyanoethylene and a specific polymerizable monomer, a cured product, a laminate, and a method for producing the laminate. Background Art

[0002] In the application of fast-curing adhesives, alkyl 2-cyanoacrylates that undergo anionic polymerization even with weak Lewis basic compounds such as water and alcohol are used as main raw materials. In the above applications, heat resistance and moisture resistance are required in addition to adhesive strength. For example, Patent Documents 1 and 2 propose adhesives that are imparted with heat resistance and moisture resistance by adding various additives.

[0003] Prior art literature

[0004] Patent Literature

[0005] Patent Document 1: Japanese Patent Application Laid-Open No. 52-78933

[0006] Patent Document 2: International Publication No. 2016 / 133166 Summary of the invention

[0007] Problems to be solved by the invention

[0008] The adhesives described in Patent Documents 1 and 2 have improved heat resistance and moisture resistance compared to conventional adhesives, but these are still insufficient, and further improvements are desired.

[0009] The present invention aims to provide a resin composition capable of providing an adhesive having excellent heat resistance and moisture resistance and a cured product using the resin composition. In addition, the present invention aims to provide a laminate using the cured product and a method for producing the laminate.

[0010] Methods used to solve problems

[0011] The present inventors have conducted research and found that highly reactive alkyl 2-cyanoacrylates have a property of being difficult to copolymerize with other monomers, but are easily copolymerized with 1,1-dicyanoethylene. Further research based on this finding has led to the discovery that a cured product obtained from a resin composition containing 1,1-dicyanoethylene and a polymerizable monomer having a specific structure at a specific ratio has excellent adhesion as well as excellent heat resistance and moisture resistance, thereby completing the present invention.

[0012] That is, the present invention provides the following [1] to [6].

[0013] [1] A resin composition comprising 1,1-dicyanoethylene (A) and a polymerizable monomer (B) represented by the following general formula (I), characterized in that:

[0014] The content of the 1,1-dicyanoethylene (A) in the total of the 1,1-dicyanoethylene (A) and the polymerizable monomer (B) is 2.0 to 99.9% by mass.

[0015] CHR 1 =CR 2 R 3 (I)

[0016] (In the general formula (I), R 1 is one or more selected from a hydrogen atom, an alkyl group, an alkenyl group and an alkoxy group,

[0017] R 2 is selected from cyano, carboxyl, -COOR 4 (R 4 is an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 20 carbon atoms), and one or more of an ester group and an acid anhydride group,

[0018] R 3 is selected from carboxyl, -COOR 5 (R 5 It is one or more of an ester group and an acid anhydride group represented by an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a divalent or higher linking group.

[0019] [2] The resin composition according to [1] above, wherein the polymerizable monomer (B) is at least one selected from the group consisting of alkyl 2-cyanoacrylates, alkyl 2-cyanopentadienoates, and dialkyl methylenemalonates.

[0020] [3] The resin composition according to [1] or [2], further comprising a Bronsted acid compound.

[0021] [4] A cured product obtained by curing the resin composition according to any one of [1] to [3] above with a Lewis basic compound.

[0022] [5] A laminate having a layer comprising the cured product according to [4] above.

[0023] [6] A method for producing a laminate, comprising a bonding step of bonding a first adherend and a second adherend using the resin composition according to any one of [1] to [3] above.

[0024] Effects of the Invention

[0025] According to the present invention, a resin composition capable of providing an adhesive having excellent heat resistance and moisture resistance and a cured product using the resin composition can be provided. In addition, a laminate using the cured product and a method for producing the laminate can be provided. DETAILED DESCRIPTION

[0026] [Resin composition]

[0027] The resin composition of the present invention is a resin composition containing 1,1-dicyanoethylene (A) and a polymerizable monomer (B) represented by the following general formula (I), characterized in that the content of the 1,1-dicyanoethylene (A) in the total of the 1,1-dicyanoethylene (A) and the polymerizable monomer (B) is 2.0 to 99.9% by mass.

[0028] CHR 1 =CR 2 R 3 (I)

[0029] (In the general formula (I), R 1 is one or more selected from a hydrogen atom, an alkyl group, an alkenyl group and an alkoxy group,

[0030] R 2 is selected from cyano, carboxyl, -COOR 4 (R 4 is an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 20 carbon atoms), and one or more of an ester group and an acid anhydride group,

[0031] R 3 is selected from carboxyl, -COOR 5 (R 5 It is one or more of an ester group and an acid anhydride group represented by an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a divalent or higher linking group.

[0032] <1,1-Dicyanoethylene(A)>

[0033] The resin composition of the present invention uses 1,1-dicyanoethylene (A). 1,1-dicyanoethylene (A) is preferably used as a raw material for a fast-curing adhesive due to its excellent reactivity, and can be used in combination with a polymerizable monomer (B) described below to obtain an adhesive resin composition having excellent heat resistance and moisture resistance.

[0034] 1,1-Dicyanoethylene can be obtained by the production methods described in J. Am. Chem. Soc., 1989, 111, 9078-9081 and US Pat. No. 2,476,270.

[0035] <Polymerizable monomer (B)>

[0036] The polymerizable monomer (B) is a monomer represented by the following general formula (I).

[0037] CHR 1 =CR 2 R 3 (I)

[0038] In the general formula (I), R 1 It is one or more selected from the group consisting of a hydrogen atom, an alkyl group, an alkenyl group and an alkoxy group.

[0039] As R 1 The alkyl group is preferably an alkyl group having 1 to 12 carbon atoms, and examples thereof include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl and n-hexyl.

[0040] As R 1 The alkenyl group is preferably an alkenyl group having 2 to 12 carbon atoms, and examples thereof include vinyl, allyl, propenyl, isopropenyl, butenyl, isobutenyl, pentenyl, isopentenyl, hexenyl (such as cis-3-hexenyl) and cyclohexenyl.

[0041] As R 1 The alkoxy group is preferably an alkoxy group having 1 to 10 carbon atoms, and examples thereof include methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy and tert-butoxy.

[0042] Among these, R 1 Preferred are a hydrogen atom, an alkyl group and an alkenyl group, and more preferred is a hydrogen atom.

[0043] In the general formula (I), R 2 is selected from cyano, carboxyl, -COOR 4 (R 4 It is one or more of an ester group and an acid anhydride group represented by an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 20 carbon atoms.

[0044] R 2 Can be made by -COOR 4 In this case, R 4 It is an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 20 carbon atoms.

[0045] As R 4 Examples of the alkyl group having 1 to 10 carbon atoms include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl and n-hexyl.

[0046] As R 4The aryl group having 6 to 20 carbon atoms includes, for example, phenyl, tolyl, xylyl and naphthyl.

[0047] R 2 The acid anhydride group may be an acid anhydride group, for example, an acid anhydride group derived from phthalic anhydride, maleic anhydride, trimellitic anhydride, pyromellitic anhydride, hexahydrophthalic anhydride, tetrahydrophthalic anhydride, methyl nadic anhydride, nadic anhydride, glutaric anhydride, dimethylglutaric anhydride, diethylglutaric anhydride, succinic anhydride, methylhexahydrophthalic anhydride, methyltetrahydrophthalic anhydride and the like.

[0048] Among these, R 2 Preferred are cyano, carboxyl and -COOR 4 (R 4 It is an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 20 carbon atoms), and is more preferably a cyano group.

[0049] R 3 is selected from carboxyl, -COOR 5 (R 5 It is one or more of an ester group and an acid anhydride group represented by an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a divalent or higher linking group.

[0050] In R 3 -COOR 5 In the case of R 5 It is an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a divalent or higher linking group.

[0051] As R 5 Examples of the alkyl group having 1 to 10 carbon atoms include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl and n-hexyl.

[0052] As R 5 The aryl group having 6 to 20 carbon atoms includes, for example, phenyl, tolyl, xylyl and naphthyl.

[0053] As R 5 Examples of divalent or higher-valent linking groups include linking groups derived from divalent or higher-valent alcohols such as ethylene glycol and glycerol. 5 Specific compounds in the case of a divalent or higher linking group include compounds obtained by esterification reaction of ethylene glycol with two 2-cyanoacrylic acids (so-called "difunctional cyanoacrylates") and compounds obtained by esterification reaction of glycerol with three 2-cyanoacrylic acids (so-called "trifunctional cyanoacrylates").

[0054] Examples of the compound constituting the linking group include diols such as ethylene glycol, 1,3-propylene glycol, 1,2-butylene glycol, 1,4-butylene glycol, 1,6-hexanediol, 1,8-octanediol, 1,9-nonanediol, 1,10-decanediol and 1,12-dodecanediol; and trivalent or higher polyols such as glycerol, pentaerythritol, trimethylolpropane and sorbitol.

[0055] In the present invention, the divalent or higher valent linking group is preferably a di- to trivalent linking group from the viewpoint of availability.

[0056] R 3 The acid anhydride group may be an acid anhydride group, for example, an acid anhydride group derived from phthalic anhydride, maleic anhydride, trimellitic anhydride, pyromellitic anhydride, hexahydrophthalic anhydride, tetrahydrophthalic anhydride, methyl nadic anhydride, nadic anhydride, glutaric anhydride, dimethylglutaric anhydride, diethylglutaric anhydride, succinic anhydride, methylhexahydrophthalic anhydride, methyltetrahydrophthalic anhydride and the like.

[0057] From the perspective of improving adhesion, R 3 Preferably, the carboxyl group, -COOR 5 (R 5 is an ester group represented by an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a divalent or higher linking group, and more preferably -COOR 5 (At this time, R 5 An ester group represented by an alkyl group having 1 to 6 carbon atoms or a di- to tri-valent linking group).

[0058] From the viewpoint of improving the adhesive strength when the resin composition is used as an adhesive, the polymerizable monomer (B) is preferably at least one selected from alkyl 2-cyanoacrylates, alkyl 2-cyanopentadienoates and dialkyl methylenemalonates, and more preferably ethyl 2-cyanoacrylate.

[0059] The method for producing the polymerizable monomer (B) is not particularly limited, and the polymerizable monomer (B) may be produced by using a single method or a combination of known methods. In addition, commercially available products may be used as the polymerizable monomer (B), for example, ethyl 2-cyanoacrylate (manufactured by Aldrich Co.) may be mentioned.

[0060] <Content of each ingredient>

[0061] In the resin composition of the present invention, the content of the 1,1-dicyanoethylene (A) in the total of the 1,1-dicyanoethylene (A) and the polymerizable monomer (B) is 2.0 to 99.9% by mass. When the content of 1,1-dicyanoethylene (A) is above the above lower limit, the heat resistance and moisture resistance of the cured product obtained from the resin composition are improved. On the other hand, when the content of 1,1-dicyanoethylene (A) is below the above upper limit, the rapid curing property of the resin composition is improved.

[0062] From the above viewpoints, the content of the 1,1-dicyanoethylene (A) in the total of 1,1-dicyanoethylene (A) and the polymerizable monomer (B) is preferably 7.0 to 99.9% by mass, more preferably 30.0 to 99.9% by mass, further preferably 50.0 to 99.9% by mass, and further preferably 70.0 to 99.9% by mass.

[0063] The content of the polymerizable monomer (B) in the total of 1,1-dicyanoethylene (A) and the polymerizable monomer (B) is preferably 0.1 to 93.0% by mass, more preferably 0.1 to 70.0% by mass, further preferably 0.1 to 50.0% by mass, and further preferably 0.1 to 30.0% by mass.

[0064] The total content of 1,1-dicyanoethylene (A) and the polymerizable monomer (B) in the resin composition of the present invention is not particularly limited, but is preferably 80% by mass or more, more preferably 90% by mass or more, further preferably 95% by mass or more, and further preferably substantially 100% by mass.

[0065] <Brønsted acid compounds>

[0066] The resin composition of the present invention preferably further contains a Bronsted acidic compound. When the resin composition of the present invention contains a Bronsted acidic compound, the reactivity of 1,1-dicyanoethylene (A) can be controlled, and the storage stability is improved. More specifically, 1,1-dicyanoethylene (A) solidifies in a trace amount of water, so it is preferred to completely remove the water during the manufacturing process, but since it is difficult to completely remove the water in reality, it is preferred to suppress the curing (inhibit the initiation of polymerization) by protonating water using a Bronsted acidic compound.

[0067] As the Bronsted acidic compound that can be used in the present invention, from the viewpoint of improving reactivity and easy availability, inorganic acids, carboxylic acids and organic sulfonic acids can be listed, among which one or more selected from sulfuric acid, hydrochloric acid, nitric acid, acetic acid, benzenesulfonic acid, p-toluenesulfonic acid and methanesulfonic acid are preferred, and it may also be a compound that reacts with water to generate a compound showing Bronsted acidity, such as sulfur dioxide and phosphorus pentoxide.

[0068] When the resin composition of the present invention contains a Bronsted acidic compound, the content thereof is preferably 0.0001 to 2.0 mass %, more preferably 0.001 to 1.0 mass %, and further preferably 0.001 to 0.05 mass % of the total amount of the resin composition. When the content of the Bronsted acidic compound is within the above range, the storage stability becomes good and a high tensile shear adhesive strength can be obtained.

[0069] From the viewpoint of storage stability, the content of the 1,1-dicyanoethylene (A) in the total amount of the resin composition is preferably 80% by mass or less, more preferably 50% by mass or less, further preferably 30% by mass or less, and further preferably 10% by mass or less.

[0070] <Other ingredients>

[0071] The resin composition of the present invention may contain, in addition to the above-mentioned components, a solvent, a filler, a tackifier, an antioxidant, a plasticizer, a flame retardant, a stabilizer, an antioxidant and the like as other components.

[0072] When the resin composition of the present invention contains other components, the content thereof is preferably 0.001% by mass or more and preferably 10% by mass or less, and more preferably 3% by mass or less in the total amount of the resin composition.

[0073] <Method for producing resin composition>

[0074] The method for producing the resin composition of the present invention is not particularly limited, and for example, the resin composition can be produced by a production method including a mixing step of mixing 1,1-dicyanoethylene (A), the polymerizable monomer (B) and other components as required, but when mixed in air, the polymerization reaction proceeds due to moisture in the air, so it is preferably produced in a dry atmosphere. It should be noted that the method for mixing the components is not particularly limited, and the components can be mixed by a known method.

[0075] [cured material]

[0076] The cured product of the present invention is a cured product obtained by curing the resin composition of the present invention described above with a Lewis basic compound, and more specifically, is a copolymer obtained by copolymerizing the components in the resin composition described above with a Lewis basic compound as a catalyst.

[0077] <Lewis basic compounds>

[0078] The Lewis basic compound used in the present invention is not particularly limited. For example, one or more selected from water, alcohols and alkylamines can be used. Examples of the alcohol include methanol, ethanol and propanol.

[0079] Examples of the alkylamine include tertiary amines such as trimethylamine, triethylamine, tripropylamine, triisopropylamine, N,N-dimethylethylamine, N,N-dimethylpropylamine, and N,N-dimethylisopropylamine.

[0080] <Method for producing cured product>

[0081] The method for producing the cured product is not particularly limited, and the cured product can be obtained by mixing the resin composition of the present invention with a Lewis basic compound at room temperature (23° C.), but can usually be obtained by reacting the resin composition of the present invention with moisture (Lewis basic compound) in the air.

[0082] The amount of the Lewis basic compound is not particularly limited, but is preferably 0.001 to 1.0 parts by mass, more preferably 0.01 to 0.5 parts by mass, relative to 100 parts by mass of the resin composition. When the content of the Lewis basic compound is within the above range, the resin composition reacts rapidly.

[0083] [Laminate and method for producing the same]

[0084] The laminate of the present invention is a laminate having a layer containing the above-mentioned cured product. The laminate structure is not particularly limited, but preferably the above-mentioned cured product is present between two adherends. By having the above-mentioned cured product between the two adherends, the adherends can be firmly bonded to each other.

[0085] The adherend used in the laminate of the present invention is not particularly limited, and examples thereof include synthetic resins, metals, ceramics, and fabrics.

[0086] Examples of synthetic resins include polyethylene, polypropylene, copolymers of ethylene and one or more α-olefins having 3 to 20 carbon atoms (e.g., propylene, 1-butene, 1-pentene, 1-hexene, etc.), ethylene-propylene-diene copolymers (EPDM), ethylene-vinyl acetate copolymers, ethylene-acrylic acid copolymers and other polyolefin resins, polyurethane resins, polyamide resins, polyester resins, polycarbonate resins and the like.

[0087] Examples of the metal include steel sheets such as stainless steel sheets, cold-rolled steel sheets, and alloyed galvanized steel sheets.

[0088] The thickness of the adherend constituting the laminate is not particularly limited. On the other hand, from the viewpoint of firmly bonding the adherends to each other, the thickness of the layer containing the cured product is preferably 0.01 to 2.0 mm, more preferably 0.015 to 1.5 mm, and even more preferably 0.02 to 1.2 mm.

[0089] The method for producing the laminate is not particularly limited, but the laminate is preferably produced by the method for producing the laminate of the present invention including a bonding step of bonding a first adherend and a second adherend with the resin composition.

[0090] The method for bonding the first adherend and the second adherend using the resin composition is not particularly limited. For example, the resin composition may be applied to one adherend, and the other adherend may be stacked thereon and cured to achieve bonding.

[0091] The method for coating the above-mentioned resin composition on the adherend is not particularly limited, and examples thereof include spin coating, spray coating, rod coating, knife coating, roll coating, roll knife coating, blade coating, die coating and gravure coating.

[0092] The coating amount of the resin composition on the adherend is not particularly limited, but is preferably 0.01 to 3.0 μL / mm 2 , more preferably 0.05 to 2.5 μL / mm 2 , more preferably 0.1 to 2.0 μL / mm 2 When the coating amount is equal to or greater than the lower limit, adherends can be firmly bonded to each other. On the other hand, when the coating amount is equal to or less than the upper limit, both can be bonded with an appropriate amount.

[0093] Example

[0094] Hereinafter, the present invention will be described in detail by way of examples, but the present invention is not limited to these examples.

[0095] The compounds used in Examples and Comparative Examples are as follows.

[0096] <1,1-Dicyanoethylene(A)>

[0097] 1,1-Dicyanoethylene

[0098] <Polymerizable monomer (B)>

[0099] Ethyl 2-cyanoacrylate (manufactured by Aldrich)

[0100] 2-Butyl cyanoacrylate (manufactured by United States Biological Co., Ltd.)

[0101] Diethyl methylenemalonate (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.)

[0102] <Brønsted acid compounds>

[0103] Methanesulfonic acid

[0104] <Material of laminate>

[0105] ·Steel plate (produced by Standard Test Piece Co., Ltd., 25 mm in length, 100 mm in width, 1.6 mm in thickness)

[0106] <Example 1>

[0107] Under dry nitrogen, 0.02 g of 1,1-dicyanoethylene (A) and 0.98 g of ethyl 2-cyanoacrylate (polymerizable monomer (B)) were mixed. A Bronsted acid compound (methanesulfonic acid) was further added to the mixture in such a manner that its content was 0.01% by mass in the total amount of the resin composition, thereby preparing a resin composition. The resin composition was evaluated in accordance with JIS K6861:1995. Specifically, 100 μL of the obtained resin composition was applied to a steel plate within a range of 12.5 mm × 25 mm, and other steel plates were overlapped on the coated surface. Then, it was allowed to stand for 1 day at room temperature (23°C) and humidity 50% RH to mix water as a Lewis basic compound, thereby curing the resin composition, thereby bonding the two steel plates to obtain a laminate. Next, the tensile shear bonding strength of each laminate was measured under each of the following conditions. The results are shown in Table 1.

[0108] <Normal bonding test>

[0109] The tensile shear bond strength of the laminate was measured at 25% RH and 25° C. using a universal material testing machine Model 5969 (manufactured by Instron Corporation) at a tensile speed of 20 mm / min.

[0110] <Heat-resistant bonding test>

[0111] The laminate was left to stand in a constant temperature and humidity chamber at 25% RH and 120°C for 3 days, and then the tensile shear bond strength of the laminate was measured at 25% RH and 25°C using a universal material testing machine Model 5969 (manufactured by Instron) at a tensile speed of 20 mm / min.

[0112] <Wet adhesion test>

[0113] The laminate was left to stand in a constant temperature and humidity chamber at 90% RH and 40°C for 1 day, and then the tensile shear bond strength of the laminate was measured at 25% RH and 25°C using a universal material testing machine Model 5969 (manufactured by Instron) at a tensile speed of 20 mm / min.

[0114] <Evaluation method of storage stability>

[0115] The resin compositions prepared according to the formulations described in Examples and Comparative Examples were left to stand for 3 hours in a test environment at a temperature of 50° C. and a humidity of 50% to confirm the presence or absence of precipitates, thereby evaluating storage stability.

[0116] <Examples 2 to 16, Comparative Examples 1 to 4>

[0117] A laminate was prepared in the same manner as in Example 1, except that the resin composition was prepared according to the formulation described in Tables 1 to 3, and the tensile shear adhesive strength was measured in the same manner. The results are shown in Tables 1 to 3.

[0118] <Examples 17 to 22>

[0119] The resin composition prepared according to the formulation described in Table 4 was left to stand for 3 hours in a test environment of a temperature of 50° C. and a humidity of 50%, and the presence or absence of precipitates generated when moisture mixed in the air was evaluated. The results are shown in Table 4.

[0120] [Table 1]

[0121]

[0122] [Table 2]

[0123]

[0124] [Table 3]

[0125]

[0126] [Table 4]

[0127]

[0128] As can be seen from the results in Table 1, the resin composition of the present invention exhibits excellent heat resistance and moisture resistance when used as an adhesive.

[0129] Furthermore, as can be seen from the results of Table 4, the resin composition of the present invention is also excellent in storage stability.

Claims

1. A resin composition comprising 1,1-dicyanoethylene (A) and a polymerizable monomer (B) represented by the following general formula (I), characterized in that: The content of the 1,1-dicyanoethylene (A) in the total of the 1,1-dicyanoethylene (A) and the polymerizable monomer (B) is 2.0 to 99.9% by mass. CHR 1 =CR 2 R 3 (I) In the general formula (I), R 1 is one or more selected from a hydrogen atom, an alkyl group, an alkenyl group and an alkoxy group, R 2 is selected from cyano, carboxyl, -COOR 4 One or more of an ester group and an anhydride group represented by 4 is an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 20 carbon atoms, R 3 is selected from carboxyl, -COOR 5 One or more of an ester group and an anhydride group represented by 5 It is an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a divalent or higher linking group.

2. The resin composition according to claim 1, wherein The polymerizable monomer (B) is at least one selected from the group consisting of alkyl 2-cyanoacrylate, alkyl 2-cyanopentadienoate, and dialkyl methylenemalonate.

3. The resin composition according to claim 1 or 2, wherein It also contains Bronsted acid compounds. 4 . A cured product obtained by curing the resin composition according to claim 1 with a Lewis basic compound. 5 . A laminate comprising a layer comprising the cured product according to claim 4 . 6 . A method for producing a laminate, comprising a bonding step of bonding a first adherend and a second adherend using the resin composition according to claim 1 .

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