Hardening components, hardened substances, and machinery

Abstract

To provide a curable composition that contains an ene compound and a thiol compound, and gives a cured product having high adhesion to a resin material.SOLUTION: A curable composition contains an ene compound (A) and a thiol compound (B). The ene compound (A) contains an acryl compound (A1), and a polymerizable monomer (A2) having, in one molecule, an ether group, a methacryloyl group and a vinyl ether group. The percentage of the polymerizable monomer (A2) is 1 mass% or more and 50 mass% or less relative to the ene compound (A).SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to a curable composition, a cured product, and a device, and more particularly to a curable composition containing an ene compound and a thiol compound, a cured product obtained by curing this curable composition, and a device produced using this curable composition. [Background technology]

[0002] Patent Document 1 discloses a resin composition containing an acrylic resin, a thiol compound, a latent curing agent, a radical polymerization inhibitor, and an anionic polymerization inhibitor. [Prior art documents] [Patent documents]

[0003] [Patent Document 1] Patent No. 4976575 Summary of the Invention [Problem to be solved by the invention]

[0004] According to the inventor's research, adhesives used in camera modules, particularly in smartphones, are increasingly required to have high flexibility, and high adhesion to resin materials such as polycarbonate, which are often used in camera modules.

[0005] An object of the present invention is to provide a curable composition that contains an ene compound and a thiol compound, and that provides a cured product thereof that has high adhesiveness to resin materials; a cured product obtained by curing this curable composition; and a device manufactured using this curable composition. [Means for solving the problem]

[0006] A curable composition according to one embodiment of the present invention comprises an ene compound (A) and a thiol compound (B). The ene compound (A) comprises an acrylic compound (A1) and a polymerizable monomer (A2) having an ether group, a (meth)acryloyl group, and a vinyl ether group in one molecule. The percentage of the polymerizable monomer (A2) is 1% by mass or more and 50% by mass or less relative to the ene compound (A).

[0007] A cured product according to one embodiment of the present invention is obtained by curing the curable composition.

[0008] An apparatus according to one aspect of the present invention comprises a first component, a second component, and a cured product interposed between the first component and the second component to bond the first component and the second component, the cured product being obtained by curing the curable composition. [Effects of the Invention]

[0009] According to the present invention, there are provided a curable composition containing an ene compound and a thiol compound, the cured product of which has high adhesiveness to resin materials; a cured product obtained by curing this curable composition; and a device manufactured using this curable composition. DETAILED DESCRIPTION OF THE INVENTION

[0010] An embodiment of the present invention will be described below. Note that the embodiment described below is merely one of various embodiments of the present invention. The embodiment described below can be modified in various ways depending on the design as long as the object of the present invention can be achieved.

[0011] The curable composition according to this embodiment (hereinafter also referred to as composition (X)) contains an ene compound (A) and a thiol compound (B). The ene compound (A) contains an acrylic compound (A1) and a polymerizable monomer (A2) having an ether group, a (meth)acryloyl group, and a vinyl ether group in one molecule. The percentage of the polymerizable monomer (A2) is 1% by mass or more and 50% by mass or less relative to the ene compound (A).

[0012] Therefore, in this embodiment, the cured product of the composition (X) can have high adhesiveness to resin materials, particularly polycarbonate.

[0013] The curable composition according to this embodiment is preferably used as an adhesive, and more preferably used to bond components in precision equipment such as camera modules. When used as an adhesive, the curable composition may be used to bond any object; that is, the use of the curable composition is not limited to bonding components in precision equipment such as camera modules. Furthermore, a cured product of the curable composition according to this embodiment may have good adhesion to resin materials, particularly to polycarbonate. However, when used as an adhesive, the curable composition may also be used to bond materials other than resin materials. Furthermore, the curable composition according to this embodiment may be used for purposes other than adhesives, such as, for example, as a sealant for electronic components.

[0014] The components contained in composition (X) will be described in detail below.

[0015] The ene compound (A) and the thiol compound (B) are reaction-curable components for curing the composition (X).

[0016] In this embodiment, the ene compound (A) contains an acrylic compound (A1) and a polymerizable monomer (A2) having an ether group, a (meth)acryloyl group, and a vinyl ether group in one molecule, where the (meth)acryloyl group refers to at least one of an acryloyl group and a methacryloyl group.

[0017] The acrylic compound (A1) is a compound having at least one of an acryloyl group and a methacryloyl group, and is not included in the polymerizable monomer (A2). The acrylic compound (A1) enables the composition (X) to have good curability.

[0018] The acrylic compound (A1) contains at least one selected from the group consisting of, for example, trimethylolpropane triacrylate, 1,6-hexanediol diacrylate, dimethylol-tricyclodecane diacrylate, acryloylmorpholine, tetrahydrofurfuryl acrylate, 4-hydroxybutyl acrylate, tris-(2-acryloxyethyl)isocyanurate, bis-(2-acryloxyethyl)isocyanurate, caprolactone-modified tris-(2-acryloxyethyl)isocyanurate, isocyanuric acid EO-modified diacrylate, and isocyanuric acid EO-modified triacrylate.

[0019] The polymerizable monomer (A2) contains, for example, a compound having a structure in which a (meth)acryloyl group and a vinyl ether group are bonded to two ends of a molecular chain containing an ether group, respectively. The polymerizable monomer (A2) contains, for example, at least one of 2-(2-vinyloxyethoxy)ethyl acrylate and 2-(2-vinyloxyethoxy)ethyl methacrylate. However, the compounds that can be contained in the polymerizable monomer (A2) are not limited to these.

[0020] The percentage of the acrylic compound (A1) is, for example, 50% by mass or more and 90% by mass or less relative to the ene compound (A).

[0021] In this embodiment, the composition (X) contains the polymerizable monomer (A2), so that a cured product of the composition (X) can have good adhesion to resin materials, particularly polycarbonates.

[0022] The percentage of the polymerizable monomer (A2) is 1% by mass or more and 50% by mass or less relative to the ene compound (A). Within this range, the polymerizable monomer (A2) allows the cured product to have good adhesion to the resin material. The percentage of the polymerizable monomer (A2) is preferably 10% by mass or more, and even more preferably 15% by mass or more. Furthermore, this percentage is preferably 40% by mass or less, and even more preferably 35% by mass or less.

[0023] The ene compound (A) may contain a maleimide compound (A3). When the ene compound (A) contains a maleimide compound (A3), the adhesion between a cured product of the composition (X) and a resin material such as a polycarbonate can be further improved.

[0024] The maleimide compound (A3) contains at least one member selected from the group consisting of, for example, N-cyclohexylmaleimide, 1-maleimido-3-maleimidomethyl-3,5,5-trimethylcyclohexane, 1,5-bis(maleimide)-2-methylpentane, N-phenylmaleimide, N-laurylmaleimide, N,N'-dodecamethylenebismaleimide, and polyphenylmethanemaleimide (for example, product number BMI-2300 manufactured by Daiwa Chemical Industry Co., Ltd.).

[0025] The maleimide compound (A3) preferably contains a maleimide compound (A31) that does not have an aromatic ring. In this case, the adhesion between the cured product of the composition (X) and resin materials such as polycarbonate can be particularly improved. The maleimide compound (A31) contains, for example, at least one selected from the group consisting of N-cyclohexylmaleimide, 1-maleimido-3-maleimidomethyl-3,5,5-trimethylcyclohexane, and 1,5-bis(maleimido)-2-methylpentane.

[0026] The molecular weight of the maleimide compound (A3) is preferably 100 or more and 1,000 or less. In this case, the maleimide compound (A3) can be well dissolved or dispersed in the composition (X), which can particularly improve the adhesion between a cured product of the composition (X) and a resin material such as a polycarbonate. The molecular weight of the maleimide compound (A3) is more preferably 120 or more, and even more preferably 150 or more. The molecular weight of the maleimide compound (A3) is more preferably 600 or less, and even more preferably 400 or less.

[0027] The percentage of the maleimide compound (A3) is preferably 25% by mass or less relative to the ene compound (A). In this case, the maleimide compound (A3) can be well dissolved or dispersed in the composition (X), thereby particularly improving the adhesion between a cured product of the composition (X) and resin materials such as polycarbonate. The percentage of the maleimide compound (A3) is more preferably 20% by mass or less relative to the ene compound (A), and even more preferably 15% by mass or less. Furthermore, the percentage of the maleimide compound (A3) is preferably 1% by mass or more relative to the ene compound (A). In this case, particularly improving the adhesion between a cured product of the composition (X) and resin materials such as polycarbonate. The percentage of the maleimide compound (A3) is more preferably 5% by mass or more, and even more preferably 10% by mass or more.

[0028] The ene compound (A) may contain only the acrylic compound (A1) and the polymerizable monomer (A2). Alternatively, the ene compound (A) may contain only the acrylic compound (A1), the polymerizable monomer (A2), and the maleimide compound (A3). When the ene compound (A) contains a compound other than the acrylic compound (A1), the polymerizable monomer (A2), and the maleimide compound (A3) (hereinafter referred to as compound (A4)), the percentage of compound (A4) relative to the ene compound (A) is preferably 20 mass% or less.

[0029] When the ene compound (A) contains the compound (A4), the compound (A4) may contain various compounds having an ethylenically unsaturated bond. For example, the compound (A4) may contain at least one selected from the group consisting of compounds having a vinyl group, such as triallyl isocyanurate, allyl glycidyl ether, trimethylolpropane diallyl ether, and pentaerythritol triallyl ether, and compounds having an isocyanurate skeleton, such as tris-(2-acryloxyethyl) isocyanurate, bis-(2-acryloxyethyl) isocyanurate, caprolactone-modified tris-(2-acryloxyethyl) isocyanurate, and triallyl isocyanurate.

[0030] The molecular weight of the ene compound (A) is, for example, 80 or more and 1,000 or less.

[0031] The thiol compound (B) preferably contains a compound having at least two thiol groups in one molecule, and more preferably contains a compound having 3 to 6 thiol groups in one molecule.

[0032] The thiol compound (B) includes, for example, an ester of a polyol and a mercapto organic acid, which includes at least one of a partial ester and a complete ester.

[0033] The polyol includes at least one selected from the group consisting of, for example, ethylene glycol, trimethylolpropane, pentaerythritol, and dipentaerythritol.

[0034] The mercapto organic acid includes at least one selected from the group consisting of mercapto aliphatic monocarboxylic acids, esters containing a thiol group and a carboxy group obtained by esterification of a hydroxy acid with a mercapto organic acid, mercapto aliphatic dicarboxylic acids, and mercapto aromatic monocarboxylic acids. Examples of mercapto aliphatic monocarboxylic acids include at least one selected from the group consisting of mercaptoacetic acid, mercaptopropionic acids such as 3-mercaptopropionic acid, and mercaptobutyric acids such as 3-mercaptobutyric acid and 4-mercaptobutyric acid. The number of carbon atoms in the mercapto aliphatic monocarboxylic acids is preferably 2 to 8, more preferably 2 to 6, even more preferably 2 to 4, and particularly preferably 3. Examples of mercapto aliphatic monocarboxylic acids having 2 to 8 carbon atoms include at least one selected from the group consisting of mercaptoacetic acid, 3-mercaptopropionic acid, 3-mercaptobutyric acid, and 4-mercaptobutyric acid. The mercaptoaliphatic dicarboxylic acid includes at least one selected from the group consisting of, for example, mercaptosuccinic acid and dimercaptosuccinic acid such as 2,3-dimercaptosuccinic acid, etc. The mercaptoaromatic monocarboxylic acid includes, for example, mercaptobenzoic acid such as 4-mercaptobenzoic acid.

[0035] Partial esters of polyols and mercapto organic acids include, for example, trimethylolpropane bis(mercaptoacetate), trimethylolpropane bis(3-mercaptopropionate), trimethylolpropane bis(3-mercaptobutyrate), trimethylolpropane bis(4-mercaptobutyrate), pentaerythritol tris(mercaptoacetate), pentaerythritol tris(3-mercaptopropionate), pentaerythritol tris(3-mercaptobutyrate), pentaerythritol tris(4-mercaptobutyrate), dipentaerythritol tetrakis(mercaptoacetate), dipentaerythritol tetrakis(3-mercaptopropionate), dipentaerythritol tetrakis(3-mercaptobutyrate), and dipentaerythritol The compound contains at least one selected from the group consisting of tetrakis(4-mercaptobutyrate) and the like.

[0036] Complete esters of polyols and mercapto organic acids include, for example, ethylene glycol bis(mercaptoacetate), ethylene glycol bis(3-mercaptopropionate), ethylene glycol bis(3-mercaptobutyrate), ethylene glycol bis(4-mercaptobutyrate), trimethylolpropane tris(mercaptoacetate), trimethylolpropane tris(3-mercaptopropionate), trimethylolpropane tris(3-mercaptobutyrate), trimethylolpropane tris(4-mercaptobutyrate), pentaerythritol tetrakis(mercaptoacetate), pentaerythritol tetrakis(3-mercaptopropionate), pentaerythritol tetrakis(3-mercaptobutyrate), pentaerythritol tetrakis(4-mercaptobutyrate), and dipentaerythritol Examples of the mercaptoester include hexakis(mercaptoacetate), dipentaerythritol hexakis(3-mercaptopropionate), dipentaerythritol hexakis(3-mercaptobutyrate), dipentaerythritol hexakis(4-mercaptobutyrate), etc. Preferably, the mercaptoester contains at least one selected from the group consisting of pentaerythritol tetrakis(3-mercaptopropionate), pentaerythritol tetrakis(3-mercaptobutyrate), dipentaerythritol hexakis(3-mercaptopropionate), and trimethylolpropane tris(3-mercaptopropionate).

[0037] The thiol compound (B) may contain, for example, tris[(3-mercaptopropionyloxy)-ethyl]-isocyanurate, 1,3,5-tris(3-mercaptobutyloxyethyl)-1,3,5-triazine-2,4,6(1H,3H,5H)-trione, or the like.

[0038] The thiol compound (B) may contain compounds other than those described above. For example, the thiol compound (B) may contain at least one selected from the group consisting of 1,4-butanedithiol, 1,6-hexaneedithiol, 1,8-octanedithiol, 1,10-decanedithiol, 3,6-dioxa-1,8-octanedithiol, and bis-2-mercaptoethyl sulfide. The thiol compound (B) may contain at least one selected from the group consisting of tris(3-mercaptopropyl)isocyanurate and 1,3,4,6-tetrakis(2-mercaptoethyl)glycoluril.

[0039] The thiol compound (B) preferably contains a compound having a secondary thiol group. For example, the thiol compound (B) preferably contains at least one selected from the group consisting of pentaerythritol tetrakis(3-mercaptobutyrate), 1,4-bis(3-mercaptobutyryloxy)butane, 1,3,5-tris(2-(3-sulfanylbutanoyloxy)ethyl)-1,3,5-triazinane-2,4,6-trione, and trimethylolpropane tris(3-mercaptobutyrate). A compound having a secondary thiol group is more likely to improve the storage stability of the composition (X) than a compound having a primary thiol group.

[0040] The total percentage of the ene compound (A) and the thiol compound (B) is preferably 70% by mass or more based on the solid content of the composition (X). However, when the composition (X) contains a filler, the total percentage of the ene compound (A) and the thiol compound (B) is preferably 70% by mass or more based on the solid content of the composition (X) excluding the filler. In this case, the composition (X) can have good reactive curing properties. This percentage is more preferably 80% by mass or more, and even more preferably 90% by mass or more. Furthermore, this percentage is, for example, 97% by mass or less. The solid content refers to the components in the composition (X) excluding volatile components. The volatile components are components that volatilize during the process of curing the composition (X) to produce a cured product and do not constitute the cured product, such as solvents.

[0041] Regarding the compounding ratio of the ene compound (A) to the thiol compound (B), the thiol compound (B) / ene compound (A) equivalent ratio (i.e., the functional group equivalent ratio of the thiol compound (B) to the ene compound (A)) is preferably 0.4 to 1.0, more preferably 0.5 to 0.8, and even more preferably 0.55 to 0.7.

[0042] The reactive curable components in composition (X) may be only the ene compound (A) and the thiol compound (B). Furthermore, composition (X) may contain a reactive curable component (hereinafter referred to as component (Y)) other than the ene compound (A) and the thiol compound (B) within a range that does not excessively impair the effects of this embodiment. When composition (X) contains component (Y), the percentage of component (Y) relative to the ene compound (A) is preferably greater than 0% by mass and not more than 70% by mass. This percentage is more preferably not more than 50% by mass, and even more preferably not more than 30% by mass. Examples of compounds contained in component (Y) include epoxy compounds, oxetane compounds, phenolic compounds, and amine compounds.

[0043] The composition (X) may contain a curing catalyst (C). In this case, the curing reaction of the composition (X) is likely to proceed when the composition (X) is heated.

[0044] The curing catalyst (C) contains at least one component selected from the group consisting of imidazoles, cycloamidines, tertiary amines, organic phosphines, tetra-substituted phosphonium / tetra-substituted borates, quaternary phosphonium salts having a counter anion other than borate, and tetraphenylboron salts.

[0045] The curing catalyst (C) may contain a latent curing catalyst (C1). In this case, the reaction of the composition (X) in an unheated state is suppressed, thereby improving the storage stability of the composition (X). The latent curing catalyst (C1) may contain at least one of a liquid latent curing accelerator and a solid-dispersion latent curing accelerator. The latent curing catalyst (C1) may contain a microencapsulated latent curing catalyst (C11). The microencapsulated latent curing catalyst (C11) contains, for example, a microencapsulated imidazole containing an imidazole as a compound having catalytic activity.

[0046] The percentage of the curing catalyst (C) relative to the total of the ene compound (A) and the thiol compound (B) is preferably 0.1% by mass or more and 35% by mass or less. When this percentage is 0.1% by mass or more, the reactivity of the composition (X) can be enhanced when the composition (X) is cured by reaction. Furthermore, when this percentage is 35% by mass or less, the storage stability of the composition (X) can be enhanced. This percentage is more preferably 0.3% by mass or more, even more preferably 0.5% by mass or more, and particularly preferably 0.8% by mass or more. Furthermore, this percentage is more preferably 20% by mass or less, even more preferably 15% by mass or less, and particularly preferably 10% by mass or less.

[0047] The composition (X) may contain a photopolymerization initiator (D). The photopolymerization initiator (D) can impart photocurability to the composition (X). In particular, when the composition (X) is used as an adhesive, if the composition (X) contains a photopolymerization initiator (D), the composition (X) can be irradiated with light to cure the composition (X) to a certain extent, thereby achieving temporary adhesion, and then the composition (X) can be heated to fully cure the composition (X) and achieve final adhesion. Furthermore, by irradiating the composition (X) with light to fully cure the composition (X), the composition (X) can be cured without heating to produce a cured product.

[0048] The photopolymerization initiator (D) contains at least one compound selected from the group consisting of, for example, aromatic ketones, acylphosphine oxide compounds, aromatic onium salt compounds, organic peroxides, thio compounds (thioxanthone compounds, thiophenyl group-containing compounds, etc.), hexaarylbiimidazole compounds, ketoxime ester compounds, borate compounds, azinium compounds, metallocene compounds, active ester compounds, compounds having a carbon-halogen bond, and alkylamine compounds.

[0049] The percentage of the photopolymerization initiator (D) relative to the total of the ene compound (A) and the thiol compound (B) is preferably 0.05% by mass or more and 2.0% by mass or less. In this case, sufficient photocurability can be imparted to the composition (X). This percentage is more preferably 0.1% by mass or more, even more preferably 0.2% by mass or more, and particularly preferably 0.4% by mass or more. This percentage is more preferably 1.5% by mass or less, even more preferably 1.0% by mass or less, and particularly preferably 0.8% by mass or less.

[0050] The composition (X) may contain a stabilizer (E). The stabilizer (E) is a compound that makes it difficult for the reaction of the ene compound (A) and the thiol compound (B), which are reactive components in the composition (X), to proceed. When the composition (X) contains the stabilizer (E), the storage stability of the composition (X) can be improved.

[0051] The stabilizer (E) preferably contains at least one of a radical polymerization inhibitor and an anionic polymerization inhibitor. In this case, the storage stability of the composition (X) is likely to be improved. This is presumably because, during storage of the composition (X), the radical polymerization inhibitor makes it difficult for the radical polymerization reaction between the ene compound (A) and the thiol compound (B) and the radical polymerization reaction between molecules in the ene compound (A) to proceed, and the anionic polymerization inhibitor makes it difficult for the anionic polymerization reaction between the ene compound (A) and the thiol compound (B) to proceed.

[0052] The radical polymerization inhibitor may contain at least one compound selected from the group consisting of, for example, 4-tert-butylpyrocatechol, tert-butylhydroquinone, 1,4-benzoquinone, dibutylhydroxytoluene, 1,1-diphenyl-2-picrylhydrazyl free radical, hydroquinone, hydroquinone monomethyl ether, mequinol, phenothiazine, and N-nitroso-N-phenylhydroxylamine aluminum, etc. However, the compounds that the radical polymerization inhibitor may contain are not limited to those listed above.

[0053] An anionic polymerization inhibitor is preferably incorporated into composition (X), particularly when composition (X) contains a curing catalyst (C). In this case, the curing reaction in composition (X) is inhibited by the curing catalyst (C) during storage of composition (X). The anionic polymerization inhibitor contains, for example, at least one of an organic boric acid compound and a compound having a phenolic hydroxyl group. The organic boric acid compound contains, for example, at least one boric acid ester selected from the group consisting of triethyl borate, tributyl borate, and triisopropyl borate. The compound having a phenolic hydroxyl group contains, for example, at least one selected from the group consisting of 2,3-dihydroxynaphthalene, 4-methoxy-1-naphthol, pyrogallol, methylhydroquinone, and t-butylhydroquinone.

[0054] The percentage of the stabilizer (E) relative to the total of the ene compound (A) and the thiol compound (B) is preferably 0.01% by mass or more and 1.5% by mass or less. If this percentage is 0.01% by mass or more, the storage stability of the composition (X) can be further improved. If this percentage is 1.5% by mass or less, the curability of the composition (X) is less likely to be impaired, and high adhesive strength can be maintained when the composition (X) is cured under appropriate conditions. This percentage is more preferably 0.05% by mass or more, and even more preferably 0.10% by mass or more. Furthermore, this percentage is more preferably 1.0% by mass or less, and even more preferably 0.7% by mass or less.

[0055] Composition (X) may further contain additives other than those described above, provided that the effects of the present embodiment are not excessively impaired. The additives include, for example, at least one selected from the group consisting of silicone powder, inorganic filler, carbodiimide compound, radical scavenger, diluent, solvent, pigment, flexibility imparting agent, coupling agent, antioxidant, thixotropy imparting agent (thixotropic agent), dispersant, etc.

[0056] Composition (X) can be prepared by mixing the components of composition (X) described above.

[0057] When the composition (X) has photocurability, that is, when the composition (X) contains a photopolymerization initiator (D), the composition (X) is filled into a cylindrical cavity having an inner diameter of 3 mm and a depth of 5 mm, and the composition (X) in this cavity is irradiated with ultraviolet light having a peak wavelength of 365 nm at an integrated light dose of 500 mJ / cm. 2 When irradiated under the above conditions, it is preferable that a portion of the composition (X) having a thickness of 0.5 mm or more is cured. In this case, the composition (X) can be sufficiently cured by irradiating the composition (X) with light. Such good photocurability of the composition (X) can be achieved within the above-mentioned range of the composition (X).

[0058] In addition, when the composition (X) contains the photopolymerization initiator (D), the composition (X) is formed into a film having a thickness of 0.5 mm on the surface of a polycarbonate member, and this film is irradiated with ultraviolet light having a peak wavelength of 365 nm at an integrated light dose of 500 mJ / cm. 2 The cured product produced by irradiation under these conditions preferably has a shear adhesive strength to the member of 8.0 MPa or more. In this case, the cured product can have particularly high adhesion to resin materials such as polycarbonate. Such high adhesion of the cured product can be achieved within the range of the composition of the composition (X) described above. This shear adhesive strength is more preferably 8.0 MPa or more, and even more preferably 10.0 MPa or more. The higher the shear adhesive strength, the more desirable it is, but the shear adhesive strength is, for example, 50 MPa or less.

[0059] Furthermore, when composition (X) is thermosetting, i.e., when composition (X) contains curing catalyst (C), composition (X) is formed into a 0.5 mm thick film on the surface of a polycarbonate member, and the film is sufficiently heated and cured to produce a cured product, which preferably has a shear adhesive strength to the member of 8.0 MPa or more. This shear adhesive strength is preferably 50 MPa or less. Such high adhesiveness of the cured product can also be achieved within the above-mentioned range of composition (X).

[0060] As described above, composition (X) can be used as an adhesive. That is, a cured product can be obtained by curing composition (X), and this cured product can be used to bond, for example, two components (hereinafter also referred to as a first component and a second component) that constitute a device.

[0061] The cured product according to this embodiment is obtained by curing composition (X). As described above, this cured product can bond a first component and a second component together.

[0062] The device according to this embodiment includes a first component, a second component, and a cured product interposed between the first and second components to bond them together. This cured product is obtained by curing composition (X). As described above, the device may be, for example, a precision device such as a camera module, but is not limited to this. Examples of the device include electronic components such as semiconductor devices, integrated circuits, large-scale integrated circuits, transistors, thyristors, diodes, and capacitors. When the device is a camera module, bonding between the first and second components means bonding between the components of the camera module. Examples of bonding between the first and second components include bonding between a substrate and a camera housing, and bonding between a lens unit and a camera housing. The first and second components are not limited to these examples.

[0063] The material of each of the first component and the second component may be, for example, a resin material such as liquid crystal polymer, polycarbonate, polyester, or polyimide, a metal such as nickel or copper, ceramic, glass, or various other substrate materials, but is not limited to these.

[0064] A method for bonding a first part and a second part using composition (X) and a method for producing a device comprising the first part, the second part and the cured product will be described.

[0065] Composition (X) is interposed between the first part and the second part. In this state, composition (X) is heated to cure composition (X) and produce a cured product. The first part and the second part are bonded together by this cured product.

[0066] When the composition (X) contains a photopolymerization initiator (D), the composition (X) is interposed between the first and second components, and before heating the composition (X), the composition (X) is irradiated with light to cause the composition (X) to harden to a certain extent. This allows the first and second components to be temporarily bonded together. In this case, the wavelength of the light irradiated onto the composition (X) is appropriately selected depending on the type of the photopolymerization initiator (D) in the composition (X). This light is, for example, ultraviolet light. By temporarily bonding the first and second components in this manner, it is easy to improve alignment accuracy by appropriately adjusting the relative positions of the first and second components.

[0067] The conditions for heating composition (X) are appropriately set so that composition (X) is sufficiently cured, for example, a heating temperature of 80° C. to 120° C. and a heating time of 30 minutes to 120 minutes.

[0068] When the composition (X) contains the photopolymerization initiator (D), the composition (X) may be placed between the first and second parts and irradiated with light to sufficiently promote the curing reaction of the composition (X), thereby curing the composition (X) without heating to produce a cured product. In this case, the first and second parts are also bonded together by this cured product. [Example]

[0069] More specific examples of this embodiment will be presented below, but this embodiment is not limited to the following examples.

[0070] 1. Preparation of the Composition Compositions were prepared by mixing the raw materials shown in Table 1-3. Details of the raw materials shown in Table 1-3 are as follows.

[0071] (1) Acrylic compounds -M-313: Isocyanuric acid EO-modified di- and triacrylate. Manufactured by Toagosei Co., Ltd. Product name: Aronix M-313. -#295: Trimethylolpropane triacrylate. Manufactured by Osaka Organic Chemical Industry Co., Ltd. Product name: Viscoat #295.

[0072] (2) Polymerizable monomers having an ether group, a (meth)acryloyl group, and a vinyl ether group in one molecule -VEEA: 2-(2-vinyloxyethoxy)ethyl acrylate. Manufactured by Nippon Shokubai Co., Ltd. Product name: VEEA. -VEEM: 2-(2-vinyloxyethoxy)ethyl methacrylate. Manufactured by Nippon Shokubai Co., Ltd. Product name: VEEM.

[0073] (3) Maleimide compounds without aromatic rings - Imilex-C: N-cyclohexylmaleimide, manufactured by Nippon Shokubai Co., Ltd. Product name: Imilex-C. -IPBM: 1-maleimido-3-maleimidomethyl-3,5,5-trimethylcyclohexane. Manufactured by Kawaguchi Chemical Industry Co., Ltd. Product name: IPBM. -2MPBM: Aliphatic type bismaleimide. Manufactured by Kawaguchi Chemical Industry Co., Ltd. Product name: 2MPBM.

[0074] (4) Maleimide compounds having aromatic rings -Imilex-P: 1,5-bis(maleimido)-2-methylpentane. Manufactured by Nippon Shokubai Co., Ltd. Product name: Imilex-P.

[0075] (5) Thiol compounds PE1: Pentaerythritol tetrakis(3-mercaptobutyrate). Manufactured by Showa Denko K.K. Product name: Karenz MTPE1 (registered trademark). -NR1: 1,3,5-tris(2-(3-sulfanylbutanoyloxy)ethyl)-1,3,5-triazinane-2,4,6-trione. Manufactured by Showa Denko K.K. Product name: KarenzMTNR1 (registered trademark).

[0076] (6) Curing catalyst -HXA9322HP: Microencapsulated imidazole, manufactured by Asahi Kasei E-Materials Corporation, product name Novacure HXA9322HP.

[0077] (7) Stabilizers -Q-1301: Radical polymerization inhibitor. N-nitroso-N-phenylhydroxylamine aluminum. Manufactured by Fujifilm Wako Pure Chemical Industries, Ltd. Product name: Q-1301. -Tributyl borate: Anionic polymerization inhibitor. Tributyl borate.

[0078] (8) Photopolymerization initiator -Omnirad 184: 1-Hydroxycyclohexyl-phenyl ketone. Manufactured by IGM Resins BV. Product name: Omnirad 184. -Omnirad TPO G: 2,4,6-trimethylbenzoyl-diphenylphosphine oxide. Manufactured by IGM Resins BV. Product name: Omnirad TPO G.

[0079] (9) Curing catalyst HXA9322HP: Microencapsulated imidazole. Manufactured by Asahi Kasei E-Materials Corporation. Product name: Novacure HXA9322HP.

[0080] (10) Additives -A-187: Coupling agent. Epoxy silane. Manufactured by MOMENTIVE. Product name: Silquest A-187. -RY200: Thixotropic agent. Fumed silica. Product name: AEROSIL (registered trademark) RY200.

[0081] 2.Evaluation Test (1) Curability The composition was filled into a cylindrical cavity with an inner diameter of 3 mm and a depth of 5 mm, and the cavity was irradiated with ultraviolet light having a peak wavelength of 365 nm at an integrated irradiance of 500 mJ / cm using EXECURE-H-1VC manufactured by HOYA Corporation. 2 The irradiation was carried out under the following conditions.

[0082] The composition was then removed from the cavity, and the surface of the cured portion of the composition was wiped with paper to remove the uncured portion from the cured portion. The thickness of this cured portion was measured with a digital caliper. The results are shown in Table 1-3.

[0083] (2) Adhesive strength #1 A test piece made of polycarbonate with a smooth surface (product name: Panlite L-1225Y, manufactured by Teijin Limited) was prepared. The arithmetic mean roughness Ra (JIS B 0601) of the surface of this test piece was measured using a surface roughness measuring instrument (model number SJ-400) manufactured by Mitutoyo Corporation, and was found to be 0.26 μm.

[0084] The composition was applied to the surface of this test piece to form a film with a diameter of 5 mm and a thickness of 0.5 mm. This film was irradiated with ultraviolet light having a peak wavelength of 365 nm at an integrated irradiance of 500 mJ / cm. 2The film was cured by irradiating under the conditions shown above, producing a cured product. The shear adhesive strength of the cured product was then measured using a shear tester (Nordson Corporation, model DAGE4000 Optima) at a test temperature of 25°C, a test speed of 0.1 mm / sec, and a test height of 50 μm. The results are shown in Table 1-3.

[0085] (3) Adhesive strength #2 For Examples 11 and 12, which used a curing catalyst, the same test pieces as in "(2) Adhesion Strength #1" above were used, and the composition was applied to the surface of the test pieces to form films with a diameter of 5 mm and a thickness of 0.5 mm. This film was irradiated with ultraviolet light with a peak wavelength of 365 nm at an integrated irradiance of 500 mJ / cm. 2 After irradiating under these conditions, the coating was thermally cured by heating at 80°C for 1 hour to produce a cured product. Next, the shear adhesive strength of the cured product to the test piece was measured using a shear tester (Nordson Corporation, model DAGE4000 Optima) at a test temperature of 25°C, a test speed of 0.1 mm / sec, and a test height of 50 μm. The results are shown in Table 3.

[0086] [Table 1]

[0087] [Table 2]

[0088] [Table 3]

[0089] As is clear from the above results, in Examples 1-13, which used a polymerizable monomer having an ether group, a (meth)acryloyl group, and a vinyl ether group in one molecule and in which the percentage of this polymerizable monomer was 1% by mass or more and 50% by mass or less relative to the ene compound, the cured product had high adhesion to polycarbonate and good curability. In contrast, in Comparative Examples 1 and 2, which did not use the polymerizable monomer, and Comparative Example 3, in which the percentage of this polymerizable monomer relative to the ene compound was more than 50% by mass, the cured product had lower adhesion to polycarbonate than the Examples.

Claims

1. an ene compound (A); and a thiol compound (B), The ene compound (A) is an acrylic compound (A1); a polymerizable monomer (A2) having an ether group, a (meth)acryloyl group, and a vinyl ether group in one molecule, the percentage of the polymerizable monomer (A2) is 1% by mass or more and 50% by mass or less based on the ene compound (A); a functional group equivalent ratio of the thiol compound (B) to the ene compound (A) is 0.4 or more and 1.0 or less; Curable composition.

2. The ene compound (A) further contains a maleimide compound (A3), the percentage of the maleimide compound (A3) is 25% by mass or less relative to the ene compound (A); The curable composition of claim 1.

3. An ene compound (A), and a thiol compound (B), The ene compound (A) is an acrylic compound (A1); a polymerizable monomer (A2) having an ether group, a (meth)acryloyl group, and a vinyl ether group in one molecule, the percentage of the polymerizable monomer (A2) is 1% by mass or more and 50% by mass or less based on the ene compound (A); The ene compound (A) further contains a maleimide compound (A3), the percentage of the maleimide compound (A3) is 25% by mass or less relative to the ene compound (A); Curable composition.

4. The molecular weight of the maleimide compound (A3) is 100 or more and 1000 or less. The curable composition according to claim 2 or 3.

5. The maleimide compound (A3) does not have an aromatic ring. The curable composition according to any one of claims 2 to 4.

6. Further containing a curing catalyst (C), The curable composition according to any one of claims 1 to 5.

7. Further containing a photopolymerization initiator (D), The curable composition according to any one of claims 1 to 6.

8. The curable composition was filled into a cylindrical cavity having an inner diameter of 3 mm and a depth of 5 mm, and the curable composition in the cavity was irradiated with ultraviolet light having a peak wavelength of 365 nm at an integrated light dose of 500 mJ / cm. ２ When irradiated under the conditions of The curable composition of claim 7.

9. The curable composition is formed into a film having a thickness of 0.5 mm on the surface of a polycarbonate member, and the film is irradiated with ultraviolet light having a peak wavelength of 365 nm at an integrated light dose of 500 mJ / cm. ２ The cured product produced by irradiating under the conditions above has a shear adhesive strength to the member of 8.0 MPa or more. The curable composition according to claim 7 or 8.

10. Further containing a stabilizer (E), The curable composition according to any one of claims 1 to 9.

11. The stabilizer (E) contains at least one of a radical polymerization inhibitor and an anionic polymerization inhibitor. The curable composition of claim 10.

12. It is an adhesive, The curable composition according to any one of claims 1 to 11.

13. A composition obtained by curing the curable composition according to any one of claims 1 to 12. cured product.

14. a first component, a second component, and a cured product interposed between the first component and the second component to bond the first component and the second component; The cured product is obtained by curing the curable composition according to any one of claims 1 to 12. device.

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