Photocurable composition

Abstract

To provide a photocurable composition having heat-resistant oil resistance after curing and showing low rates of mass change and volume change after curing.SOLUTION: The present invention can provide a photocurable composition comprising (A) a difunctional polyester-based urethane (meth)acrylate oligomer, (B) a monofunctional (meth)acrylate monomer, (C) a difunctional (meth)acrylate monomer, (D) a trifunctional or higher (meth)acrylate monomer, and (E) a photopolymerization initiator. The present invention can also provide a cured product of the photocurable composition. Furthermore, the present invention can provide a filter component comprising a filter for filtering fuel or oil, and the cured product of the photocurable composition fixed to the filter.SELECTED DRAWING: None

Description

Technical Field

[0001] The present invention relates to a photocurable composition, a cured product of the photocurable composition, and parts and products including the cured product.

Background Art

[0002] Curable compositions are used in various products and parts and are widely used in a wide range of fields as adhesives and fixing agents. Furthermore, cured products of curable compositions are widely used in various products and industrial parts provided thereon as sealing materials, fixing materials, support materials, and the like. Curable compositions are used, for example, in filter parts for removing impurities from fluids (e.g., gases, liquids) such as metal scraps, dust, and dirt, and various devices equipped with such parts.

[0003] Filter parts and filter devices including cured products obtained by curing curable compositions are used in a wide range of fields such as automobiles (passenger cars, motorcycles, etc.), airplanes (light airplanes, jet planes, etc.), ships (merchant ships (cargo ships, passenger ships, etc.), small ships (cruisers, fishing boats, etc.), etc.), trains, and trams; combustion devices and hydraulic devices having internal combustion engines or hydraulic engines. For example, filter parts for lubricating oil are provided in a filter device for lubricating oil in order to remove impurities in lubricating oil such as engine oil or hydraulic oil for operating a device. In addition, in combustion engines (engines; combustion devices such as stoves and fan heaters using oil such as petroleum; large combustion devices such as boilers; etc.), before burning fuel oil (fossil fuel oil such as gasoline, kerosene, and light oil, biofuel oil, etc.), fuel oil filter parts are provided in a filter device for fuel oil in order to remove impurities such as metal scraps, dust, and dirt contained in the fuel oil.

[0004] For example, conventionally, a two-component heat-curable composition using epoxy has been used for the support part or mounting part of filter parts used in automobile engines. For example, in order to have good durability and strength in contact with various oils such as engine oil, brake fluid, and transmission oil, a resin composition comprising 5 to 85% by weight of polyamide resin (a) and 95 to 15% by weight of polyphenylene sulfide resin (b) is formed into 100 parts by weight of a resin component, and an oil-related part characterized by being obtained by molding a resin composition comprising 0.5 to 200 parts by weight of an inorganic filler (c) has been proposed (see Patent Document 1).

Prior Art Documents

Patent Documents

[0005]

Patent Document 1

Summary of the Invention

Problems to be Solved by the Invention

[0006] In the case of an epoxy-based two-component thermosetting composition such as that in Patent Document 1, since it is a two-component type and further thermosetting, the workability is not very good. For this reason, the present inventors examined a (meth)acrylate-based photocurable composition in order to improve the workability. However, since generally (meth)acrylate-based photocurable compositions are said to have low heat and oil resistance after curing, the present inventors examined a composition that can obtain a (meth)acrylate-based photocurable composition having good heat and oil resistance after curing. Furthermore, since the cured product used in contact with oil is required to have a small mass change rate and little concern about oil absorption and component elution into the oil, and also to have a small volume change rate and little concern about shape deformation, the present inventors also examined these aspects.

[0007] Based on the above, the main object of the present invention is to provide a photocurable composition having heat and oil resistance after curing and having small mass change rate and volume change rate after curing.

Means for Solving the Problems

[0008] As a result of intensive studies, the present inventors have found that by making the photocurable composition have a specific composition, a cured product having heat and oil resistance can be formed after curing. That is, the present invention is as follows.

[0009] The present invention provides a photocurable composition containing (A) a bifunctional polyester-based urethane (meth) acrylate oligomer, (B) a monofunctional (meth) acrylate monomer, (C) a bifunctional (meth) acrylate monomer, (D) a trifunctional or higher functional (meth) acrylate monomer, and (E) a photopolymerization initiator. The present invention can also provide the above composition used as a fixing agent or an adhesive. The present invention can also provide a cured product of the above photocurable composition. The present invention can also provide a filter part containing a cured product of the above photocurable composition. The present invention can also provide a product containing a cured product of the above photocurable composition. The present invention can also provide a filter part including a filter for filtering fuel or oil and a cured product of the above photocurable composition fixed to the filter.

[0010] The above photocurable composition may have a mass change rate within the range of -10 to +10% before and after the heat and oil resistance test, and / or a volume change rate within the range of -10 to +10% before and after the heat and oil resistance test. The above (E) photopolymerization initiator may be a benzyl ketal-based compound or an acetophenone-based compound. The above (B) monofunctional (meth) acrylate monomer may have a substituted or unsubstituted aryl group. The above (B) monofunctional (meth) acrylate monomer may be 2-phenoxyethyl acrylate. The above (C) bifunctional (meth) acrylate monomer may be alkylene glycol di(meth)acrylate. The (C) difunctional (meth)acrylate monomer may be 1,6 - hexanediol diacrylate. The (D) trifunctional or higher - functional (meth)acrylate monomer may be trimethylol C2 - C10 alkane alkoxy triacrylate. The (D) trifunctional or higher - functional (meth)acrylate may be trimethylolpropane ethoxy triacrylate. The cured product of the photocurable composition may have a hardness of 50 - 80 in the normal state and 50 - 80 after oil immersion. The composition may be used for fixing an oil filter. The composition may be used as a heat - resistant oil - resistant cured product after curing. The cured product of the photocurable composition may be one or more selected from a sealing material, a fixing material, and a supporting material, and / or the product may be one or more selected from an automobile, an airplane, a ship, a combustion device, and a dust collector.

Advantages of the Invention

[0011] The present invention can provide a photocurable composition capable of forming a cured product having heat - resistant oil resistance after curing.

Brief Description of the Drawings

[0012]

Figure 1

Figure 2

Modes for Carrying Out the Invention

[0013] Hereinafter, the embodiments for carrying out the present invention will be described in detail. It should be noted that the embodiments described below show an example of typical embodiments of the present invention, and the present invention is not limited only to these embodiments.

[0014] 1. Photocurable composition The photocurable composition according to the present invention preferably contains a polyester-based urethane (meth) acrylate oligomer, a monofunctional (meth) acrylate monomer, and a polyfunctional (meth) acrylate monomer. The polyfunctionality may be bifunctional, trifunctional, or more. The (meth) acrylate may contain a hydrocarbon in its molecular structure, and the hydrocarbon can be classified into aliphatic or aromatic, and the aliphatic can be classified into acyclic (for example, linear, branched) or cyclic (for example, alicyclic) non-aromatic. The hydrocarbon may be either saturated or unsaturated, and may be either chain (linear or branched) or cyclic (alicyclic, aromatic).

[0015] In the present invention, “(meth) acrylate” means acrylate, methacrylate, or a mixture thereof. In the present invention, a monofunctional (meth) acrylate monomer means that one molecule has one photopolymerizable carbon-carbon double bond, that is, it means having one acryloyl group or methacryloyl group (hereinafter also referred to as “(meth) acryloyl group”). Further, a polyfunctional (meth) acrylate means a (meth) acrylate having two or more (meth) acryloyl groups.

[0016] The polyester-based urethane (meth) acrylate oligomer is preferably a polyester-based urethane (meth) acrylate, more preferably a polyfunctional polyester-based urethane (meth) acrylate, and still more preferably a bifunctional polyester-based urethane (meth) acrylate.

[0017] In addition, the photocurable composition according to the present invention preferably contains a photocurable acrylic resin component. The photocurable acrylic resin component is not particularly limited, and for example, it is preferably one or more selected from a photocurable oligomer, a monofunctional (meth)acrylate monomer, a polyfunctional (meth)acrylate monomer, etc. The photocurable acrylic resin component used can be manufactured by a known production method, and a commercially available product can also be used.

[0018] As a preferred embodiment of the present invention, it is preferable to provide a photocurable composition, a cured product thereof, and a component containing the cured product, which at least contain a bifunctional polyester-based urethane (meth)acrylate oligomer as component (A), a monofunctional (meth)acrylate monomer as component (B), a bifunctional (meth)acrylate monomer as component (C), and a (meth)acrylate monomer having three or more functional groups as component (D). More preferably, it is more suitable for the photocurable composition to further contain a photoinitiator as component (E).

[0019] 1-1. Each component of the photocurable composition according to the present invention

[0020] <Bifunctional polyester-based urethane (meth)acrylate oligomer (component (A))> It is preferable for the photocurable composition according to the present invention to contain or use a photocurable oligomer from the viewpoint of improving the toughness of the cured product.

[0021] As the photocurable oligomer, a (meth)acrylate oligomer containing one or several (meth)acryloyl groups in the oligomer molecular structure is preferable. The (meth)acrylate oligomer is preferably a copolymer of a (meth)acrylate monomer and a monomer or oligomer other than the (meth)acrylate. Examples of the monomer or oligomer other than the (meth)acrylate include, but are not limited to, carbamate, etc.

[0022] The backbone of the (meth)acrylate oligomer used in the present invention is not particularly limited, but the (meth)acrylate oligomer preferably has a urethane backbone. By using the (meth)acrylate oligomer as a raw material of the photocurable composition, the toughness and the like of the cured product can be improved.

[0023] The number of (meth)acryloyl groups in the oligomer molecular structure of the (meth)acrylate oligomer used in the present invention is preferably 1 or more, more preferably 1 to 5, still more preferably 1 to 4, even more preferably 2 to 3, and even more preferably 2 (that is, bifunctional).

[0024] Examples of the (meth)acrylate oligomer used in the present invention include, but are not particularly limited to, polyether-based urethane (meth)acrylate oligomers, polyurethane-based (meth)acrylate oligomers, polyester-based urethane (meth)acrylate oligomers, etc. Among these, from the viewpoint of improving the toughness of the cured product, polyester-based urethane (meth)acrylate is preferable, and more preferably, polyester urethane-based acrylate.

[0025] The (meth)acrylate oligomer used in the present invention is preferably a bifunctional polyester-based urethane (meth)acrylate oligomer, and more preferably, a bifunctional polyester-based urethane acrylate oligomer, from the viewpoint of improving the toughness of the cured product.

[0026] In the present invention, it is preferable to use a mixture obtained by mixing the above-described (meth)acrylate oligomer (preferably a bifunctional polyester-based urethane (meth)acrylate oligomer) and the monofunctional (meth)acrylate monomer described below. In the present invention, a composition obtained by further mixing a mixture containing a (meth)acrylate oligomer and a monofunctional (meth)acrylate monomer with components other than these components (for example, a bifunctional (meth)acrylate, a trifunctional (meth)acrylate, etc.) is more preferable. The molecular weight of the (meth)acrylate oligomer (preferably a bifunctional polyester urethane acrylate oligomer) used in the present invention is preferably from 1,000 to 20,000, more preferably from 5,000 to 15,000, and still more preferably from 8,000 to 10,000. The viscosity of the (meth)acrylate oligomer (BM viscometer, 60 °C) is preferably from 10,000 to 50,000 mPa·s, more preferably from 20,000 to 40,000 mPa·s, and still more preferably from 25,000 to 35,000 mPa·s.

[0027] <Mono-functional (meth)acrylate monomer (component (B))> The photocurable composition in the present invention preferably contains or uses a mono-functional (meth)acrylate monomer. The total number of carbon atoms of the mono-functional (meth)acrylate monomer used in the present invention is 7 or more as a suitable lower limit value, 16 or less as a suitable upper limit value, and more preferably from 10 to 14.

[0028] The mono-functional (meth)acrylate monomer used in the present invention is not particularly limited, but a mono-functional (meth)acrylate monomer having an aromatic ring is preferred. The mono-functional (meth)acrylate monomer having the aromatic ring is a monomer containing only one (meth)acrylate group and having an aromatic ring in the monomer structure. The "aromatic ring" is not particularly limited, and examples thereof include aromatic monocyclic hydrocarbons such as benzene rings and condensed polycyclic hydrocarbons such as naphthyl. The aromatic ring may be located in any part of the structure. The aromatic group may not have a substituent, and may have a substituent as long as the effects of the present invention are not impaired.

[0029] The mono-functional (meth)acrylate monomer used in the present invention preferably has an aryl group, and the aryl group is preferably unsubstituted or has a substituent. The aryl group may have a substituent as long as the effects of the present invention are not impaired, and an aryl group having a substituent (preferably an aromatic monocyclic hydrocarbon group such as a benzene ring) is preferred.

[0030] The monofunctional (meth)acrylate monomer having an aromatic ring used in the present invention is not particularly limited. For example, benzyl (meth)acrylate, phenoxyethyl (meth)acrylate, ethoxylated o-phenylphenol (meth)acrylate, phenoxydiethylene glycol (meth)acrylate, phenoxypolyethylene glycol (meth)acrylate, 3-phenoxybenzyl (meth)acrylate, phenoxyethyl (meth)acrylate, neopentyl glycol-(meth)acrylic acid-benzoic acid ester, and the like can be mentioned.

[0031] The monofunctional (meth)acrylate monomer having an aromatic ring used in the present invention is more preferably a monomer having a phenoxy group. Examples of the monomer having a phenoxy group include phenoxyethyl (meth)acrylate, 2-hydroxy-3-phenoxypropyl (meth)acrylate, methylphenoxyethyl (meth)acrylate, phenoxydiethylene glycol (meth)acrylate, phenoxypolyethylene glycol (meth)acrylate, etc. Among these, acrylate-based ones are preferred. Furthermore, it is preferably phenoxyethyl (meth)acrylate, and more preferably phenoxyethyl acrylate (also referred to as 2-phenoxyethyl acrylate).

[0032] One or more selected from the group consisting of compounds such as the above-mentioned "monofunctional (meth)acrylate monomer" may be used.

[0033] <Polyfunctional (meth)acrylate monomer> The photocurable composition in the present invention preferably contains or uses a polyfunctional (meth)acrylate monomer. Thereby, the workability before curing or the toughness of the cured product can be improved. Also, by using a polyfunctional (meth)acrylate, the hardness and toughness of the cured product of the photocurable composition of the present invention after curing can be more favorably exhibited. In the present invention, the polyfunctional (meth)acrylate monomer means that one molecule has two or more photopolymerizable carbon-carbon double bonds, that is, it means having two or more (meth)acryloyl groups. The number of (meth)acryloyl groups in the “polyfunctional” of the polyfunctional (meth)acrylate monomer is preferably, for example, two or more, preferably 2 to 10, more preferably 2 to 6, and even more preferably 2 or 3.

[0034] Among the polyfunctional (meth)acrylate monomers used in the present invention, difunctional (meth)acrylate monomers and (meth)acrylates having three or more functions are preferred, and more preferably, a combination of difunctional (meth)acrylate and trifunctional (meth)acrylate. More preferably, it is a difunctional (meth)acrylate monomer which is an ester compound of two or more (meth)acrylic acids and a polyhydric alcohol (more preferably a dihydric alcohol).

[0035] <Difunctional (meth)acrylate (Component (C))> The photocurable composition of the present invention preferably contains or uses a difunctional (meth)acrylate monomer. Thereby, the workability before curing can be improved.

[0036] As the difunctional (meth)acrylate, although not particularly limited, those having a substituted or unsubstituted chain aliphatic group are preferred, and the chain may be linear or branched, and linear is more preferred. The number of carbon atoms of the chain aliphatic group (preferably an alkylene group) is preferably 3 to 12, more preferably 3 to 9, and even more preferably 5 to 7.

[0037] The difunctional (meth)acrylate used in the present invention is not particularly limited. For example, (mono)alkylene glycol di(meth)acrylates such as 1,4-butanediol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, 1,9-nonanediol di(meth)acrylate, propylene glycol di(meth)acrylate, 1,3-butylene glycol di(meth)acrylate, neopentyl glycol di(meth)acrylate; bisphenol alkylene oxide adduct di(meth)acrylates such as di(meth)acrylate of ethylene oxide adduct of bisphenol A, di(meth)acrylate of ethylene oxide adduct of bisphenol F, di(meth)acrylate of ethylene oxide adduct of bisphenol S, di(meth)acrylate of ethylene oxide adduct of thiobisphenol, di(meth)acrylate of ethylene oxide adduct of brominated bisphenol A; polyalkylene glycol di(meth)acrylates such as polyethylene glycol di(meth)acrylate, polypropylene glycol di(meth)acrylate; di(meth)acrylate of neopentyl glycol hydroxy pivalate and the like can be mentioned. The "alkylene (group)" in the di(meth)acrylate is preferably chain-like (preferably linear), and / or the alkylene group is not particularly limited, and examples thereof include ethylene, propylene, butylene, butane, hexane, nonane, etc., and one or more selected from these can be used. The "alkylene" in the "polyalkylene" and "alkylene oxide adduct" in the di(meth)acrylate is preferably ethylene or propylene. Examples of the difunctional (meth)acrylate include, but are not limited to, 1,6-hexanediol diacrylate, tripropylene glycol diacrylate, and ethylene glycol diacrylate.

[0038] Among the difunctional (meth)acrylates used in the present invention, alkylene glycol di(meth)acrylate is preferred. The chain of the "alkylene (group)" in the alkylene glycol di(meth)acrylate is preferably linear, and / or the number of carbon atoms of the "alkylene (group)" is preferably 2 to 9, more preferably 5 to 7. The difunctional (meth)acrylate is preferably 1,6-hexanediol di(meth)acrylate, and more preferably 1,6-hexanediol diacrylate. 1,6-Hexanediol diacrylate has better compatibility with the (meth)acrylate oligomer, and thus can better improve the aesthetic property (beauty of appearance) such as better suppressing the generation of wavy patterns after curing.

[0039] <Trifunctional or higher (meth)acrylate (component (D))> The photocurable composition in the present invention preferably contains or uses a trifunctional or higher (meth)acrylate monomer, and a trifunctional or higher acrylate monomer is preferred. Thereby, the hardness and toughness of the cured product can be improved. In the trifunctional or higher (meth)acrylate monomer, the number of (meth)acryloyl groups in the molecular structure is preferably 3 or more as this suitable lower limit value, and preferably 10 or less, more preferably 8 or less, still more preferably 6 or less, even more preferably 5 or less as this suitable upper limit value. The suitable numerical range is preferably 3 to 6, and more preferably 3 (that is, trifunctional). The trifunctional or higher (meth)acrylate oligomer may have a substituent.

[0040] The trifunctional or higher functional (meth)acrylate monomer used in the present invention is not particularly limited, but preferably one or more selected from trimethylolalkane-based (preferably trimethylolpropane-based), pentaerythritol-based, dipentaerythritol-based, and glycerin-based monomers. When it has an alkylene oxide, those of ethylene oxide and / or propylene oxide are preferred. Among these, trimethylolpropane-based (meth)acrylate monomers are preferred, and as a more preferred embodiment, trimethylolpropane alkoxylate (meth)acrylate is more preferred.

[0041] The 3- to 6-functional (meth)acrylate monomer is not particularly limited. For example, trimethylol C2-C10 alkane tri(meth)acrylates such as trimethylolpropane tri(meth)acrylate and trimethylol octane tri(meth)acrylate; trimethylol C2-C10 alkane alkoxy tri(meth)acrylates such as trimethylolpropane ethoxytri(meth)acrylate, trimethylolpropane polypropoxytri(meth)acrylate, and trimethylolpropane polyethoxypolypropoxytri(meth)acrylate; pentaerythritol-based (meth)acrylates such as pentaerythritol tri(meth)acrylate, pentaerythritol tri(meth)acrylate, and pentaerythritol EO-modified tetra(meth)acrylate (e.g., PE(EO)TTA); dipentaerythritol-based (meth)acrylates such as dipentaerythritol tri(meth)acrylate, dipentaerythritol tetra(meth)acrylate, dipentaerythritol penta(meth)acrylate, and dipentaerythritol hexa(meth)acrylate (e.g., DPHA); glycerin propoxytri(meth)acrylate (e.g., GPTA); and ditrimethylolpropane tetra(meth)acrylate (e.g., DTMPTTA), etc.

[0042] In the trimethylol C2-C10 alkane alkoxytri(meth)acrylate, "C2-C10 alkane" is preferably propane, and the "alkoxy" may be either monoalkoxy or polyalkoxy. Further, examples of the "alkoxy" in the trimethylol C2-C10 alkane alkoxytri(meth)acrylate include propoxy, ethoxy, and ethoxypropoxy, among which propoxy and ethoxy are preferred, and propoxy is more preferred.

[0043] The trifunctional (meth)acrylate monomer used in the present invention is not particularly limited, and examples thereof include pentaerythritol tri(meth)acrylate; pentaerythritol tri(meth)acrylate; trimethylol C2-C10 alkane tri(meth)acrylate such as trimethylolpropane tri(meth)acrylate and trimethylol octane tri(meth)acrylate; trimethylol C2-C10 alkane alkoxytri(meth)acrylate such as trimethylolpropane ethoxytri(meth)acrylate, trimethylolpropane polypropoxytri(meth)acrylate, and trimethylolpropane polyethoxypolypropoxytri(meth)acrylate.

[0044] Examples of suitable 3-6 functional acrylate monomers include trimethylolpropane triacrylate (TMPTA), trimethylolpropane ethoxytriacrylate (TMPEOTA), glycerin propoxylated triacrylate (GPTA), pentaerythritol tetraacrylate (PETA), or dipentaerythritol hexaacrylate (DPHA).

[0045] Among the trifunctional or higher (meth)acrylates used in the present invention, trimethylol C2-C10 alkane polyalkoxytri(meth)acrylate is preferred, among which trimethylolpropane ethoxytri(meth)acrylate is more preferred, and trimethylolpropane ethoxytriacrylate (TMPEOTA: C21H32O9) is even more preferred.

[0046] The polyfunctional (meth)acrylate monomer contained in the photocurable composition of the present invention may be one or more selected from the group consisting of compounds such as the above-described "polyfunctional (meth)acrylate monomer". In addition, the polyfunctional (meth)acrylate monomer etc. may have a polar group within a range not impairing the effects of the present invention.

[0047] <Monomers or oligomers other than the above> The photocurable acrylic resin component may contain a monofunctional or polyfunctional (meth)acrylate monomer other than the above, or a photocurable oligomer etc. within a range not impairing the effects of the present invention. As the monofunctional or polyfunctional (meth)acrylate monomer other than the above, for example, a (meth)acrylate monomer having at least one or more functional groups selected from the group consisting of a vinyl ether group, an epoxy group, and an oxetanyl group may be included.

[0048] <Photopolymerization initiator (component (E))> The photocurable composition of the present invention preferably further contains a photopolymerization initiator, and a radical photopolymerization initiator is more preferable. The compounds used for these may be commercial products or may be produced by known production methods. The photopolymerization initiator used in the present invention is not particularly limited, and examples thereof include acetophenone-based (for example, benzyl ketal-based, α-hydroxyacetophenone-based), phosphine oxide-based, aminoalkylphenone-based, benzoylformate-based, oxime ester-based, etc., and one or more selected from these can be used. Among the photopolymerization initiators used in the present invention, the acetophenone-based is preferable, more preferably the benzyl ketal-based and / or α-hydroxyacetophenone-based, and even more preferably the benzyl ketal-based. It is even more preferable to select one or more from the following examples of the benzyl ketal-based and α-hydroxyacetophenone-based. By using an acetophenone-based photopolymerization initiator, a cured product excellent in heat and oil resistance can be obtained more favorably.

[0049] The photoinitiator used in the present invention preferably contains at least a benzyl ketal-based photoinitiator. Among benzyl ketal-based photoinitiators, more preferably, it is 2,2-dimethoxy-2-phenylacetophenone. By selecting such a photoinitiator, the photocurable composition of the present invention can be cured better without tackiness, and has an excellent advantage that it can provide a cured product that is more excellent in heat and oil resistance, and has a smaller mass change rate and volume change rate.

[0050] The benzyl ketal-based compound is not particularly limited, but preferably has a benzyl ketal skeleton structure in the molecule. For example, 2,2-dimethoxy-2-phenylacetophenone, 2,2-diethoxy-2-phenylacetophenone, etc. can be mentioned. Among these, 2,2-dimethoxy-2-phenylacetophenone is preferable. In addition, as commercially available products of benzyl ketal-based compounds, for example, Omnirad (former Irgacure) 651 (IGM Resins B.V.) and the like can be mentioned.

[0051] The α-hydroxyacetophenone-based compound is not particularly limited, but preferably has an α-hydroxyacetophenone skeleton structure in the molecule. For example, 1-hydroxycyclohexyl phenyl ketone, 2-hydroxy-2-methyl-1-phenyl-1-propanone, 2-hydroxy-1-{4-[4-(2-hydroxy-2-methyl-propionyl)-benzyl]phenyl}-2-methyl-1-propanone, and 1-[4-(2-hydroxyethoxy)-phenyl]-2-hydroxy-2-methyl-1-propan-1-one and the like can be mentioned. Among these, 2-hydroxy-1-{4-[4-(2-hydroxy-2-methyl-propionyl)-benzyl]phenyl}-2-methyl-1-propanone is preferable. In addition, as commercially available products of α-hydroxyacetophenone-based compounds, for example, Omnirad184, Omnirad127 and the like can be mentioned.

[0052] Although not particularly limited, the phosphine oxide-based compound preferably has a phosphine oxide skeleton structure in the molecule, and examples thereof include bis(2,4,6-trimethylbenzoyl)-phenylphosphine oxide and 2,4,6-trimethylbenzoyl-diphenyl-phosphine oxide. Commercially available products of the phosphine oxide-based compound include, for example, Omnirad819, SB-PI718, and the like.

[0053] Although not particularly limited, the α-aminoalkylphenone-based compound preferably has an α-aminoalkylphenone skeleton structure in the molecule, and examples thereof include 2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one and 2-benzyl-2-(dimethylamino)-4´-morpholinobutyrophenone. Commercially available products of this compound include, for example, Omnirad 907, Omnirad 369, Omnirad 369E, and the like.

[0054] Although not particularly limited, the aminoalkylphenone-based compound preferably has an aminoalkylphenone skeleton structure in the molecule, and examples thereof include 2-dimethylamino-2-(4-methylbenzyl)-1-(4-morpholin-4-yl-phenyl)-butan-1-one and 2-dimethylamino-2-(4-methyl-benzyl)-1-(4-morpholin-4-yl-phenyl)-butan-1-one. Commercially available products of this compound include, for example, Omnirad907, Omnirad379EG, and the like.

[0055] Although not particularly limited, the benzoylformate-based compound preferably has a benzoylformate skeleton structure in the molecule, and examples thereof include methyl benzoylformate. Commercially available products of this compound include Omnirad MBF and the like.

[0056] One or more selected from the group consisting of compounds such as the above-mentioned "photoinitiator" may be used.

[0057] 1-2. Content or usage ratio of each component in the photocurable composition <Ratio of photocurable oligomer and monofunctional (meth)acrylate monomer> The content mass ratio or usage mass ratio (hereinafter also referred to as "ratio") of [photocurable oligomer and monofunctional (meth)acrylate monomer] in 100 parts by mass of the photocurable acrylic resin component contained in the photocurable composition of the present invention is not particularly limited, but is preferably 60 to 95 parts by mass, more preferably 65 to 90 parts by mass, still more preferably 70 to 90 parts by mass, and even more preferably 75 to 85 parts by mass.

[0058] The ratio of [bifunctional polyester-based urethane (meth)acrylate oligomer and monofunctional (meth)acrylate monomer (preferably 2-phenoxyethyl acrylate)] in 100 parts by mass of the photocurable acrylic resin component contained in the photocurable composition of the present invention is not particularly limited, but the preferred lower limit is preferably 60 parts by mass or more, more preferably 65 parts by mass or more, still more preferably 70 parts by mass or more, and more preferably 75 parts by mass or more. Also, the preferred upper limit is preferably 95 parts by mass or less, more preferably 90 parts by mass or less, still more preferably 85 parts by mass or less, and the preferred numerical range is more preferably 70 to 90 parts by mass, and still more preferably 75 to 85 parts by mass.

[0059] The ratio of [curable oligomer (preferably bifunctional polyester-based urethane (meth)acrylate oligomer) and monofunctional (meth)acrylate monomer] is preferably 45 to 75:55 to 25, more preferably 50 to 70:50 to 30, and still more preferably 55 to 65:45 to 35. As a preferred embodiment, the ratio of [bifunctional polyester-based urethane (meth)acrylate oligomer and 2-phenoxyethyl acrylate] is preferably 45 to 75:55 to 25, more preferably 50 to 70:50 to 30, and still more preferably 55 to 65:45 to 35.

[0060] <Ratio of bifunctional (meth)acrylate> The proportion of [bifunctional (meth)acrylate] in 100 parts by mass of the photocurable acrylic resin component contained in the photocurable composition of the present invention is not particularly limited, but is preferably 5 to 40 parts by mass, more preferably 10 to 35 parts by mass, still more preferably 10 to 30 parts by mass, and even more preferably 15 to 25 parts by mass.

[0061] The proportion of [phenoxyethyl (meth)acrylate (preferably 1,6 - hexanediol diacrylate)] in 100 parts by mass of the photocurable acrylic resin component contained in the photocurable composition of the present invention is not particularly limited. As the preferred lower limit, it is preferably 5 parts by mass or more, more preferably 10 parts by mass or more, still more preferably 15 parts by mass or more. As the preferred upper limit, it is preferably 40 parts by mass or less, more preferably 35 parts by mass or less, still more preferably 30 parts by mass or less, and even more preferably 25 parts by mass or less. The preferred numerical range is more preferably 10 to 40 parts by mass, and still more preferably 15 to 25 parts by mass.

[0062] In addition, based on the total amount of [curable oligomer, monofunctional (meth)acrylate monomer, and bifunctional (meth)acrylate] contained in the photocurable composition of the present invention, various components can be blended. For example, the proportion of bifunctional (meth)acrylate with respect to 100 parts by mass of the total amount is preferably 10 to 40 parts by mass, more preferably 15 to 35 parts by mass, and still more preferably 20 to 30 parts by mass. When the unit of the total amount is 100% by mass, the unit of the proportion of various components may be% by mass.

[0063] [[ID=eleven]] <Ratio of (meth)acrylate having three or more functional groups> The proportion of [trifunctional or higher (preferably 3 - 6 functional) (meth)acrylate] in 100 parts by mass of the photocurable acrylic resin component contained in the photocurable composition of the present invention is not particularly limited, but is preferably 0.5 to 7 parts by mass, more preferably 1 to 6 parts by mass, still more preferably 2 to 5 parts by mass, even more preferably 3 to 5 parts by mass, and more preferably 3.5 to 4.5 parts by mass.

[0064] The proportion of [trimethylolalkane-based (preferably trimethylolpropane-based)] in 100 parts by mass of the photocurable acrylic resin component contained in the photocurable composition of the present invention is not particularly limited, but is preferably 0.5 to 7 parts by mass, more preferably 1 to 6 parts by mass, still more preferably 2 to 5 parts by mass, even more preferably 3 to 5 parts by mass, and even more preferably 3.5 to 4.5 parts by mass.

[0065] The proportion of [trimethylolpropane ethoxytri(meth)acrylate (preferably trimethylolpropane ethoxytriacrylate)] in 100 parts by mass of the photocurable acrylic resin component contained in the photocurable composition of the present invention is not particularly limited, but the preferable lower limit thereof is preferably 0.5 part by mass or more, more preferably 1 part by mass or more, still more preferably 2 parts by mass or more, even more preferably 3 parts by mass or more, and even more preferably 3.5 parts by mass or more. Also, the preferable upper limit thereof is preferably 7 parts by mass or less, more preferably 6 parts by mass or less, still more preferably 5 parts by mass or less, even more preferably 4.5 parts by mass or less. The preferable numerical range is more preferably 1 to 7 parts by mass, and still more preferably 3 to 5 parts by mass.

[0066] The proportion of [polyfunctional (meth)acrylate having 3 or more functional groups (preferably 3 to 6 functional groups)] with respect to 100 parts by mass of [curable oligomer, monofunctional (meth)acrylate monomer, and bifunctional (meth)acrylate] contained in the photocurable composition of the present invention is preferably 0.5 to 7 parts by mass, more preferably 1 to 6 parts by mass, still more preferably 2 to 5 parts by mass, even more preferably 3 to 5 parts by mass, and even more preferably 3.5 to 4.5 parts by mass.

[0067] <Amount or proportion of photoinitiator> The amount or ratio of the photoinitiator (preferably an acetophenone-based one) is preferably 0.01 part by mass to 10 parts by mass, more preferably 0.1 part by mass to 8 parts by mass, still more preferably 0.5 to 5 parts by mass, even more preferably 1 to 3 parts by mass, and even more preferably 0.9 to 2.5 parts by mass, based on 100 parts by mass of the photocurable acrylic resin component. It is preferable that the total amount of 100 parts by mass of the photocurable acrylic resin component is the total amount of 100 parts by mass of the photocurable oligomer, the monofunctional monomer, the difunctional monomer, and the monomer having three or more functional groups.

[0068] The amount or ratio of the photoinitiator (preferably an acetophenone-based one) is preferably 0.01 to 10 parts by mass, more preferably 0.1 to 8 parts by mass, still more preferably 0.5 to 5 parts by mass, even more preferably 1 to 3 parts by mass, and even more preferably 1 to 2.5 parts by mass, based on 100 parts by mass of [the photocurable oligomer, the monofunctional monomer, and the difunctional monomer].

[0069] The amount or ratio of the benzyl ketal-based photoinitiator (preferably 2,2-dimethoxy-2-phenylacetophenone) is preferably at least 0.01 part by mass, more preferably at least 0.1 part by mass, still more preferably at least 0.5 part by mass, and even more preferably at least 0.9 part by mass as the preferred lower limit, based on 100 parts by mass of the photocurable acrylic resin component. Also, as the preferred upper limit, it is preferably at most 10 parts by mass, more preferably at most 8 parts by mass, still more preferably at most 5 parts by mass, even more preferably at most 3 parts by mass, even more preferably at most 2.5 parts by mass, and even more preferably at most 2 parts by mass. It is preferably 0.01 part by mass to 10 parts by mass, more preferably 0.1 part by mass to 8 parts by mass, still more preferably 0.5 to 5 parts by mass, even more preferably 1 to 3 parts by mass, and even more preferably 1 to 2.5 parts by mass. It is preferable that the total amount of 100 parts by mass of the photocurable acrylic resin component is the total amount of 100 parts by mass of the photocurable oligomer, the monofunctional monomer, the difunctional monomer, and the monomer having three or more functional groups.

[0070] The amount or proportion of the benzyl ketal-based photoinitiator (preferably 2,2-dimethoxy-2-phenylacetophenone) is, based on 100 parts by mass of [the photocurable oligomer, the monofunctional monomer, and the bifunctional monomer], preferably at least 0.01 part by mass, more preferably at least 0.1 part by mass, still more preferably at least 0.5 part by mass, even more preferably at least 1 part by mass as the preferred lower limit. Also, as the preferred upper limit, it is preferably at most 10 parts by mass, more preferably at most 8 parts by mass, still more preferably at most 5 parts by mass, even more preferably at most 3 parts by mass, more preferably at most 2.5 parts by mass, and more preferably at most 2 parts by mass. The preferred numerical range may be more preferably a content ratio of 1 to 3 parts by mass, still more preferably 1 to 2.5 parts by mass.

[0071] The amount or proportion of the photocurable oligomer described above may preferably be the amount or proportion of a bifunctional polyester-based (meth)acrylate oligomer, and more preferably the amount or proportion of a bifunctional polyester-based urethane (meth)acrylate oligomer (preferably a bifunctional polyester-based urethane acrylate oligomer). Also, the amount or proportion of the monofunctional (meth)acrylate monomer may preferably be the amount or proportion of a monofunctional (meth)acrylate monomer having an aryl group, and more preferably the amount or proportion of phenoxyethyl (meth)acrylate (preferably phenoxyethyl acrylate). Also, the amount or proportion of the bifunctional (meth)acrylate monomer may preferably be the amount or proportion of (mono)alkylene glycol di(meth)acrylate, and more preferably the amount or proportion of 1,6-hexanediol di(meth)acrylate (preferably 1,6-hexanediol diacrylate). In addition, the amount or ratio of the trifunctional or higher-functional (preferably trifunctional to hexafunctional) (meth)acrylate may preferably be the amount or ratio of a trimethylolalkane-based (preferably trimethylolpropane-based) compound, more preferably the amount or ratio of a trimethylol C2-C10 alkane alkoxytri(meth)acrylate, and even more preferably the amount or ratio of trimethylolpropane ethoxytri(meth)acrylate (preferably trimethylolpropane ethoxytriacrylate). In addition, the amount or ratio of the photopolymerization initiator may preferably be the amount or ratio of an acetophenone-based photopolymerization initiator, more preferably the amount or ratio of an α-hydroxyacetophenone-based photopolymerization initiator, and even more preferably the amount or ratio of 2,2-dimethoxy-2-phenylacetophenone.

[0072] 1-3. Optional Components The photocurable composition of the present invention may contain, for example, optional components used in photocurable compositions such as defoaming agents, antioxidants, adhesion-imparting agents, surfactants, curing agents, flame retardants, etc., within a range that does not impair the effects of the present invention, and one or more selected from these can be used.

[0073] Examples of the defoaming agent include, but are not limited to, silicone-based defoaming agents such as dimethyl silicone, alkyl-modified silicone, phenyl-modified silicone, and fluorine-modified silicone, and polyacrylate-based defoaming agents. Among these, silicone-based defoaming agents are preferred, and more specifically, defoaming polysiloxane-based defoaming agents are preferred. The content of the defoaming agent is preferably 0.1 to 5 parts by mass, more preferably 0.5 to 3 parts by mass, and even more preferably 0.5 to 1.5 parts by mass with respect to 100 parts by mass of the total amount. Examples of the surfactant include, but are not limited to, fluorine-based surfactants, silicone-based surfactants, alkyl-based surfactants, and polyacrylate-based surfactants. Among these, polyacrylate-based surfactants are preferred.

[0074] Examples of the antioxidant include phenolic and non-phenolic ones. The phenolic antioxidants are not particularly limited, and examples thereof include hindered phenolic, semi-hindered phenolic, and res-hindered phenolic antioxidants. The non-phenolic antioxidants are not particularly limited, and examples thereof include sulfur-based, phosphorus-based, and amine-based ones. Among these, hindered phenolic antioxidants are preferred, and these are not particularly limited, and examples thereof include pentaerythritol tetrakis(3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate), octadecyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)-propionate benzene propanoic acid, 3,5-bis(1,1-dimethylethyl)-4-hydroxy-C7-C9 branched alkyl ester, 4,6-bis(octylthiomethyl)-o-cresol, and the like. Examples of the commercially available products include IRGANOX1010, IRGANOX1076, IRGANOX1135, IRGANOX1520L, and the like.

[0075] From the viewpoint of antioxidant properties, the antioxidant may be blended. However, from the viewpoint of reducing the hardness variation of the cured product during production, it is preferably not contained at 0.2% by mass or more, more preferably not contained at 0.1% by mass or more, still more preferably not contained at 0.05% by mass or more or 0.01% by mass or more, and more preferably not blended with the antioxidant in 100% of the total amount.

[0076] 1-4. Uses of the photocurable composition and the cured product of the present invention

[0077] Conventional (meth)acrylate-based photocurable compositions were considered to have lower heat and oil resistance compared to thermosetting compositions containing epoxy. However, as shown in the following [Examples], the cured product obtained by curing the (meth)acrylate-based photocurable composition of the present invention was excellent in heat and oil resistance. Therefore, the composition of the present invention can be used for parts that require heat resistance, oil resistance, or heat and oil resistance, and can also be used, for example, as a fixing agent or an adhesive. And the composition of the present invention can be used as a heat and oil resistant cured product after curing. The cured product is not particularly limited, and examples include sealing materials, fixing materials, support materials, and molds. After the composition of the present invention is used and cured on a part, it can also be used as a member having heat and oil resistance contained in the part (for example, a sealing material, a fixing material, a support material, etc.). One or more of these can be used. And it is also possible to further include or incorporate the parts obtained using the composition of the present invention into a product. In addition, the composition and cured product of the present invention are not limited to the applications of parts and products that require heat resistance and / or oil resistance, and can be widely used in other parts, products, or applications.

[0078] Furthermore, the photocurable composition of the present invention can be selected as a one-component type compared to the conventional two-component thermosetting composition using epoxy. When the photocurable composition of the present invention is used as a one-component type, operations such as metering and mixing can be omitted or shortened, so the labor of the operation can be reduced and the workability becomes better. In the case of thermosetting, it becomes a cured product by heating for about ten minutes (for example, about 10 minutes), but the photocurable composition of the present invention becomes a cured product by light irradiation for about several minutes or less (for example, about 10 to 40 seconds), so the curing time can be shortened and the workability becomes better. In addition, even when the photocurable composition of the present invention is brought into contact with a filter, it does not impregnate widely, and it is possible to avoid a decrease in filter performance due to the photocurable composition impregnating and curing outside the applied portion.

[0079] Since the hardness of the cured product of the present invention after immersion is good, the cured product of the present invention is excellent in heat and oil resistance. Also, the mass change rate (%) of the cured product of the present invention before and after the heat and oil resistance test is small, and the cured product of the present invention has little concern about oil absorption and elution of components, is good, and is excellent in low oil absorption and oil resistance (low elution property with respect to oil). Also, since the volume change rate (%) of the cured product of the present invention before and after the heat and oil resistance test is small, there is little or no expansion or contraction of the cured product of the present invention, and the sealing property can be maintained as good as the initial state even after long-term use, which is good. The cured product of the present invention is excellent in low expansibility and low shrinkage, and in particular, it is excellent in maintaining the sealing property of the cured product and low deformability of the cured product (especially in maintaining the shape of the support or the fixed object (maintaining the sealing property, low peelability, etc.)). Since the tensile strength tends to increase as it becomes harder and decrease as it becomes easier to stretch, it is preferable that the change in the tensile strength of the cured product of the present invention before and after the heat and oil resistance test is small.

[0080] Also, the cured product of the present invention can be appropriately applied to any shape or any part by known molding techniques of photocurable resins (for example, mold molding, cutting, etc.). In the present invention, a cured product having a desired shape can be obtained by pouring a liquid and fluid photocurable composition into a mold frame so as to have a desired shape and photocuring it. Further, the cured product after curing may be cut into a desired shape using a cutting device such as a NC lathe. In the present invention, since it can be cured into a desired shape using a mold frame, there is also an advantage that the material loss is less. Also, since the photocurable composition of the present invention easily obtains a cured product having a small volume change rate, there is an advantage that it is easy to obtain a part within dimensional tolerances.

[0081] <Properties of the composition and cured product of the present invention>

[0082] <Viscosity of the photocurable composition> The viscosity of the photocurable composition of the present invention is not particularly limited, but in a sol state, from the viewpoint of suppressing immersion in a filter, the preferred lower limit is preferably 5,000 mPa·s or more, more preferably 10,000 mPa·s or more, still more preferably 30,000 mPa·s or more, and even more preferably 50,000 mPa·s or more. Also, as the preferred upper limit, it is preferably 150,000 mPa·s or less, more preferably 100,000 mPa·s or less, still more preferably 80,000 mPa·s or less, 70,000 mPa·s or less, and the preferred numerical range is preferably 10,000 to 100,000 mPa·s. This measurement can be performed with a BH type viscometer (23°C, 10 revolutions). <Method for measuring viscosity> After charging each raw material and kneading until uniform, the defoamed composition can be measured with a No. 7 rotor of a BH type viscometer. Measurement conditions: JIS K 7117-1, K 7117-2 and JIS K 1557-5, viscometer B type series BH type viscometer 10 revolutions, No. 7 rotor, measurement time 1 minute, measurement temperature 23°C.

[0083] <Mass change rate (%)> The mass change rate (%) is not particularly limited, but is preferably -10% to +10%, more preferably -5% to +5%, still more preferably -4% to +4%, even more preferably -3% to +3%, and even more preferably -2% to +2%. Regarding after the heat resistance test, it was carried out according to <Test method (heat-resistant oil test)> described in [Examples] below. Also, the "mass change rate before and after the heat-resistant oil test" in this specification refers to the "mass change rate" obtained by <Mass change rate (%)>.

[0084] <Method for measuring mass [g] and method for calculating mass change rate [%]> The mass of the cured product test piece was measured with an electronic balance before and after the heat-resistant oil test. Regarding the heat-resistant oil test, it was carried out according to <Test method (heat-resistant oil test)> described in [Examples] below. Based on the mass before the heat-resistant oil test, the mass change rate was calculated using the following formula. · Mass change rate [%] = (mass after heat-resistant oil test × 100 / mass before heat-resistant oil test) - 100

[0085] <Volume change rate [%]> The volume change rate indicates how much the volume has changed after the heat-resistant oil test, based on the volume before the heat-resistant oil test. In addition, the "volume change rate before and after the heat-resistant oil test" in this specification refers to the "volume change rate" obtained by <Volume change rate [%]>. The volume change rate of the cured product of the present invention is not particularly limited, but is preferably ±10%, more preferably -5% to +5%, still more preferably -4% to +4%, more preferably -3% to +3%, more preferably -2% to +2%, still more preferably -1% to +1%, more preferably -0.5% to +0.5%, more preferably -0.25% to +0.25%, and more preferably -0.1% to +0.1%. The heat-resistant oil test was conducted according to the <Test method (heat-resistant oil test)> described in the following [Examples].

[0086] <Volume [g / cm 3 Measurement method and calculation method of volume change rate [%]> The mass of the cured product test piece in air and water was measured before and after the heat-resistant oil test. The volume of the cured product test piece before and after the heat-resistant oil test was calculated respectively from the following formula. · Volume [cm^3] = (ms,a - ms,il) / ρil ms,a: Mass of the test piece measured in air [g] ms,il: Mass of the test piece measured in the immersion liquid (water) [g] ρil: Density of the immersion liquid (water) [g / cm^3] Next, based on the volume before the heat-resistant oil test, the volume change rate was calculated by the following formula. · Volume change rate [%] = (volume after heat-resistant oil test × 100 / volume before heat-resistant oil test) - 100

[0087] <Tensile strength change [MPa]> The tensile strength change indicates how much the tensile strength has changed after the heat-resistant oil test, based on the tensile strength before the heat-resistant oil test. The change in the tensile strength of the cured product of the present invention is not particularly limited, but is preferably -20 MPa to +20 MPa, more preferably -18 MPa to +18 MPa, still more preferably -15 MPa to +15 MPa, and even more preferably -10 MPa to +10 MPa. Regarding the heat-resistant oil test, it was carried out according to the <Test Method (Heat-Resistant Oil Test)> described in the following [Examples].

[0088] <Measurement Method of Tensile Strength [MPa] and Calculation Method of Change in Tensile Strength> A tensile test was performed on the cured product test pieces before and after the heat-resistant oil test, and the tensile strength [MPa] was measured (conforming to JIS K6251). The tensile speed was 200 mm / min. Based on the tensile strength before the heat-resistant oil test, the change in tensile strength was calculated using the following formula. ·Change in tensile strength [MPa] = Tensile strength after heat-resistant oil test - Tensile strength before heat-resistant oil test

[0089] <Elongation Change Rate [%]> The elongation change rate indicates how much the elongation has changed after the heat-resistant oil test, based on the elongation before the heat-resistant oil test. The elongation change rate [%] of the cured product of the present invention after the heat-resistant oil test is not particularly limited, but is preferably -22% to +22%, more preferably -20% to +20%, and still more preferably -18% to +18%. Regarding the heat-resistant oil test, it was carried out according to the <Test Method (Heat-Resistant Oil Test)> described in the following [Examples].

[0090] <Measurement Method of Elongation [%] and Calculation Method of Elongation Change Rate [%]> A tensile test was performed on the cured product test pieces before and after the heat-resistant oil test, and the elongation [%] was measured (conforming to JIS K6251). The tensile speed was 200 mm / min. Based on the elongation before the heat-resistant oil test, the elongation change rate [%] was calculated using the following formula. ·Elongation change rate [%] = (Elongation after heat-resistant oil test × 100 / Elongation before heat-resistant oil test) - 100

[0091] <Hardness of Cured Product in Normal State> The normal hardness of the cured product of the present invention is not particularly limited. The preferred lower limit is preferably 50 or more, more preferably 55 or more. The preferred upper limit is preferably 75 or less, more preferably 70 or less, still more preferably 65 or less, and even more preferably 60 or less. The preferred numerical range is preferably 55 to 65.

[0092] <Measurement method for normal hardness and hardness after immersion> The normal hardness and the hardness after immersion were measured according to JIS K 6253, Type D.

[0093] <Hardness of the cured product after immersion> The hardness of the cured product of the present invention after immersion is not particularly limited. The preferred lower limit is preferably 50 or more, more preferably 55 or more. The preferred upper limit is preferably 75 or less, more preferably 70 or less, still more preferably 65 or less, and even more preferably 60 or less. The preferred numerical range is preferably 55 to 65. In addition, the difference between the normal hardness and the hardness after immersion in the cured product of the present invention is preferably small, preferably within 15, more preferably within 10, and still more preferably within 8. Note that "after immersion" means after the heat-resistant oil test, and for after the heat-resistant test, it was carried out according to <Test method (heat-resistant oil test)> described in [Examples] below.

[0094] As described above, from the viewpoint of good oil resistance and / or heat resistance of the cured product, the photocurable composition of the present invention can be used to obtain a wide variety of products and components provided therein, and is also preferable from the viewpoints of shortening the curing time and improving workability. Therefore, the photocurable composition of the present invention can be used for various products and the components and industrial parts provided therein, etc., and is not particularly limited thereto, but is preferably used for components that require oil resistance and / or heat resistance, or for obtaining components for oil resistance and / or heat resistance. Further, the photocurable composition is preferably for use in one or more selected from applications such as sealing materials, fixing, and adhesion. Further, the photocurable composition is preferably for use in a filter or filter parts.

[0095] The photocurable composition and cured product of the present invention can be used for various products or parts of the products, and the cured product of the present invention can be included in various products or parts of the products. The products that can use the composition and cured product of the present invention are not particularly limited, but for example, automobiles (ordinary cars, light automobiles, trucks, special vehicles, motorcycles, etc.), airplanes (light airplanes, jet airplanes, etc.), ships (merchant ships such as cargo ships and passenger ships, small ships such as cruisers and fishing boats, etc.), combustion equipment (stoves for fuel oil, heaters, etc.), air purifiers, dust collectors, etc. can be mentioned. Further, among these, products including components that require oil resistance and / or heat resistance (for example, seal components, support components, filter components, etc.) are preferred. Among the said components, components that come into contact with fluids (liquids, gases) are preferred, and more preferably components for oil.

[0096] As a preferred embodiment of the present invention, filter parts containing the cured product of the present invention and products containing the said parts are preferred, and the said filter parts are more preferably those that filter fluids (liquids, gases), more preferably for liquids (for example, water and / or oil), and even more preferably for oil. For a product containing a cured product of a preferred photocurable composition, it is preferred that the cured product is one or more selected from a sealing material, a fixing material, and a support material, and / or the said product is one or more selected from an automobile, an airplane, a ship, a combustion device, and a dust collector.

[0097] Therefore, the present invention can provide a photocurable composition used as a fixing agent or an adhesive. Further, the present invention can provide a photocurable composition used for a filter, preferably a photocurable composition for fixing a filter or adhering a filter, and more preferably a photocurable composition used for fixing an oil filter. In addition, the present invention can provide a cured product that can be used as a component for sealing, fixing, or supporting an object even in an environment where heat resistance, oil resistance, or heat and oil resistance is required. Examples of the component obtained from the cured product of the present invention include, but are not particularly limited to, a sealing material, a fixing material, a supporting material, etc., and one or more selected from these are preferable. Further, it is more preferable that the cured product is included in or used in a product including industrial parts that require oil resistance, heat resistance, or heat and oil resistance.

[0098] Also, as described above, by using the photocurable composition of the present invention, it is possible to significantly shorten the production time required for filter parts by shortening the curing time and improving workability. In addition, the cured product obtained by using the photocurable composition of the present invention has good heat and oil resistance, and the mass change rate and volume change rate before and after the heat and oil resistance test are small, so it is suitable as a cured product for use in oil. Further, the photocurable composition of the present invention has low impregnability with respect to the filter and can be fixed to the filter by a simple operation, so it is excellent in workability. Therefore, the cured product of the present invention is preferably used as a sealing material or a support for parts that come into contact with oil or are used in oil, such as oil filter parts. For this reason, the photocurable composition of the present invention is preferably used for one or more selected from forming an oil filter, forming an oil-resistant part or member, or fixing these filters and parts. Since the photocurable composition of the present invention is excellent in oil resistance, it is preferably used for oil filters and their parts. For example, the oil filter is not particularly limited, and includes lubricating oil filters, fuel oil filters, etc. as described in the above [Background Art], and these examples described above can be appropriately adopted.

[0099] The photocurable composition and the cured product of the present invention can be used, for example, as parts used for a filter or filter parts provided in a filter device. The cured product is preferably used as a part for fixing or supporting a filter, and more preferably used as a fixing member or a supporting part of a filter part. The cured product may be formed or disposed on any surface such as the side surface of the filter, and in the case of a cylindrical filter, the cured product may be formed or disposed on the upper surface and / or the lower surface thereof. Thereby, the filter part of the present invention can be fixed or supported to a filter device.

[0100] The photocurable composition and the cured product of the present invention can be used for filters (for example, oil filters, fuel oil filters, lubricating oil filters) that filter oils such as fuel oil or lubricating oil. More specifically, the fuel oil filter is not particularly limited, but a filter that removes impurities contained in the fuel oil before fuel is preferred. Further, as the lubricating oil filter, a filter that removes sludge, wear powder, dust, etc. contained in oils such as hydraulic fluid, engine oil, transmission oil (ATF, etc.), lubricating oil, etc. is preferred. Furthermore, in the present invention, it is preferably used for filters for lubricating oil and / or fuel oil. More specifically, as for lubricating oil, it is more preferably used for automotive lubricating oil and / or industrial lubricating oil, and more preferably for engine oil that requires heat-resistant oiliness due to high temperature. Since the cured product of the photocurable composition of the present invention is excellent in heat-resistant oiliness, it is more preferably for engine oil and / or fuel oil.

[0101] <Filter> The material of the filter used in the present invention is not particularly limited, and a material that can filter fluids (for example, gases such as air; liquids such as water and / or oil, etc.) is preferred. For example, filter paper (cellulose fiber, synthetic fiber, glass fiber, etc.) can be mentioned, and one or more selected from these can be used. The shape of the filter used in the present invention is preferably a shape configured to be able to filter fluids. The shape of the filter is not particularly limited, and examples include one or more selected from a chrysanthemum shape, an MW method (density type), a spiral shape, a laminated type, a sponge type, a cabin, etc., and it is possible to process and use them into a shape according to the purpose. Further, the filter used in the present invention is not particularly limited, and examples include one or more selected from an air filter (such as an air filter for an automobile cabin, an air conditioner filter, etc.), an oil filter (such as an engine oil filter for an automobile), etc.

[0102] <Method for curing a photocurable composition> In the present invention, a photocurable composition is a composition having the property of curing when irradiated with light. The light irradiated to cure the photocurable composition of the present invention is not particularly limited, and examples include radiation in a broad sense such as ultraviolet rays, electron beams (beta rays), gamma rays, or alpha rays, more preferably ultraviolet rays and / or electron beams, and even more preferably ultraviolet rays. In the present invention, light generally used when curing a photocurable composition may be used.

[0103] The apparatus for irradiating light can be appropriately selected by those skilled in the art depending on the type of light to be irradiated. A commercially available one may be used as the apparatus. For example, to irradiate an electron beam, an accelerated electron beam usually taken out from an electron beam accelerator of 20 to 2000 kV is irradiated. The irradiation dose of the electron beam is, for example, 1 to 300 kGy, and may preferably be 5 to 200 kGy. Further, the integrated light amount of ultraviolet rays is not particularly limited, but can be appropriately set, for example, in the range of 10 to 3000 mJ / cm 2 and is preferably 500 to 2000 mJ / cm 2 and the integrated light amount (mJ / cm 2 ) can be obtained by UV illuminance (milliwatts (mW) / cm 2 ) × irradiation time (seconds). The UV illuminance (intensity) is not particularly limited, but is preferably 10 to 300 mW / cm 2, more preferably 50 to 200 mW / cm 2 . In addition, for irradiating ultraviolet rays, UV irradiation devices such as germicidal lamps, ultraviolet fluorescent lamps, carbon arcs, xenon lamps, low-pressure mercury lamps, medium-pressure mercury lamps, high-pressure mercury lamps, ultra-high-pressure mercury lamps, metal halide lamps, and electrodeless lamps may be used. The wavelength of the ultraviolet rays to be irradiated is, for example, 200 nm to 450 nm, or 200 nm to 400 nm, etc., and light including such ultraviolet wavelengths may also be used.

[0104] [Photocurable Composition and Method for Producing Cured Product of the Same]

[0105] The photocurable composition in the present invention may be produced using stirring means known in the technical field to which the present invention pertains. For example, the photocurable composition can be produced by stirring the photocurable composition of the present invention or the photocurable acrylic resin component contained therein in a container with a stirrer. As the stirrer, a device known in the art may be used. For example, stirring conditions such as stirring time and temperature during stirring may also be appropriately set by those skilled in the art.

[0106] The photocurable composition used in the present invention can be applied to an object such as a filter and cured so as to be fixed to the object by photocuring. The cured product of the photocurable composition may be used as a support of the filter, or may be used as an adhesive for fixing the filter and other parts, and its use is not particularly limited.

[0107] Examples of the use of the photocurable composition for an object are not particularly limited, and one example is given below, but the present invention is not limited thereto.

[0108] As an example, it includes pouring the fluid photocurable composition in the present invention into a mold of a desired shape; disposing an object (such as a filter) to be fixed in the mold containing the photocurable composition and bringing it into contact with the photocurable composition at a desired position of the object; irradiating with light after contact, etc. Thereby, the composition hardens, adheres to the filter, etc., and a cured product of a desired shape is obtained, and if necessary, the cured product can be removed from the mold. Furthermore, by repeating these steps, a cured product may be obtained at a necessary location or part. The mold is preferably made of a material (such as a plastic resin) that allows light (such as ultraviolet light) for curing to pass through. Also, the photocurable composition of the present invention has the advantage that it can be cured even in a short time and can be adjusted to have low impregnability even for filters, etc. Also, as an example, it includes bringing the photocurable composition of the present invention into contact with an object or a component to be provided on the object; fixing and irradiating with light the object and the component in a state of being in contact with each other via the photocurable composition, etc. Thereby, the cured product is photocured, and a product in a state where the object and the component are fixed can be obtained.

[0109] [Examples of the manufacturing method of the photocurable composition and its cured product]

[0110] An example of the usage method of the photocurable composition of the present invention will be described below with reference to FIGS. 1 and 2, but the filter component and the manufacturing method of the present invention are not limited thereto, nor are they limited to FIGS. 1 and 2. The manufacturing method of the filter component of the present invention preferably includes pouring the photocurable composition 1 into the mold 2 (FIG. 1A), inserting a part (for example, an end) of the filter 3 into the mold 2 (FIG. 1B), irradiating with light from the light irradiation device 4 to cure (FIG. 1C), and demolding the filter component 100 provided with the cured product 10 (FIG. 1D). Furthermore, more preferably, in order to provide a cured product in the remaining other parts as necessary, the above steps 1 to 4 are repeated (for example, FIG. 2, filter component 101). Thereby, filter components 100 and 101 provided with a cured product in the required filter part can be obtained. A light-transmissive container such as a donut-shaped mold having a convex portion at the center may be employed. During curing, a predetermined light (e.g., ultraviolet light) may be irradiated for a certain period of time (e.g., about 1 to 30 seconds).

[0111] Thereby, a filter component including a filter and a cured product of the photocurable composition can be manufactured. The cured product is preferably fixed to the filter. The cured product is preferably formed as a fixing portion or a support portion of the filter. And, in the filter component, a member of the cured product is formed on a part of the filter, and by providing this member, the attachment and detachment of the filter component to the filter device become easier, and it becomes easier to fix the filter component to the filter device. Further, the cured product of the present invention has the advantage of having heat-resistant oiliness, and even in a device that generates heat, it becomes easier to maintain the fixing of the filter component during operation.

[0112] Thereby, heat-resistant oiliness cured products can be provided on both bottom surfaces of the filter, a circular space is formed on the bottom surface of the filter, and the space forms a substantially cylindrical hollow along the longitudinal direction. Due to this substantially cylindrical hollow, the dirty oil on the outer periphery is filtered by the chrysanthemum-shaped filter in the direction of the center of the substantially cylindrical hollow, and thus the oil from which impurities have been removed flows along the longitudinal direction of the filter and circulates through the filter device. Such a filter component can be applied to a filter component for general engine oil such as an automobile, but the present invention is not particularly limited to such a shape. Since the photocurable composition in the present invention can be used in a liquid state, it has the advantage that the shape of the cured product can be freely changed, and also the fixing portion to the filter and the shape of the support of the filter can be freely designed and changed.

[0113] 2. This technology can appropriately adopt the following configurations or other aspects. · [1] (A) A bifunctional polyester-based urethane (meth) acrylate oligomer, (B) A monofunctional (meth) acrylate monomer, (C) A bifunctional (meth) acrylate monomer, (D) A (meth)acrylate monomer having a functionality of 3 or more, and (E) A photoinitiator, A photocurable composition containing the same. · [2] The photocurable composition according to [1] above, wherein the mass change rate before and after the heat-resistant oil test is in the range of -10 to +10%, and / or the volume change rate before and after the heat-resistant oil test is in the range of -10 to +10%. · [3] The photocurable composition according to [1] or [2] above, wherein the (E) photoinitiator is a benzyl ketal-based compound. · [4] The photocurable composition according to any one of [1] to [3] above, wherein the (E) photoinitiator is an acetophenone-based compound. · [5] The photocurable composition according to any one of [1] to [4] above, wherein the (B) monofunctional (meth)acrylate monomer has a substituted or unsubstituted aryl group. · [6] The photocurable composition according to any one of [1] to [5] above, wherein the (B) monofunctional (meth)acrylate monomer is 2-phenoxyethyl acrylate. · [7] The photocurable composition according to any one of [1] to [6] above, wherein the (C) difunctional (meth)acrylate monomer is alkylene glycol di(meth)acrylate. · [8] The photocurable composition according to any one of [1] to [7] above, wherein the (C) difunctional (meth)acrylate monomer is 1,6-hexanediol diacrylate. · [9] The photocurable composition according to any one of [1] to [8] above, wherein the (D) (meth)acrylate monomer having a functionality of 3 or more is trimethylol C2-C10 alkane alkoxy triacrylate. ·

[10] The photocurable composition according to any one of [1] to [9] above, wherein the (D) (meth)acrylate having a functionality of 3 or more is trimethylolpropane ethoxy triacrylate. ·

[11] The cured product of the photocurable composition has a hardness of 50 to 80 in the normal state and 50 to 80 after oil immersion, and is the photocurable composition according to any one of [1] to

[10] above. ·

[12] The viscosity of the photocurable composition is 10,000 to 100,000 mPa·s, and is the photocurable composition according to any one of [1] to

[11] above. ·

[13] The photocurable composition is used as a fixing agent or an adhesive, and is the photocurable composition according to any one of [1] to

[12] above. ·

[14] The composition is used for fixing a filter (preferably a filter for oil), and is the photocurable composition according to any one of [1] to

[13] above. The oil filter is preferably a filter for lubricating oil or fuel oil. ·

[15] The composition is used as a heat-resistant oil-resistant cured product after curing, and is the photocurable composition according to any one of [1] to

[14] above. ·

[16] The cured product of the photocurable composition according to any one of [1] to

[15] above. ·

[17] A product containing the cured product of the photocurable composition according to any one of [1] to

[16] above. Preferably, the cured product is one or more selected from a sealing material, a fixing material, and a supporting material, and / or the product is one or more selected from an automobile, an airplane, a ship, a combustion device, and a dust collector. ·

[18] An oil filter part containing the cured product of the photocurable composition according to any one of [1] to

[16] above. ·

[19] A filter for filtering oil (preferably lubricating oil or fuel oil), and the cured product of the photocurable composition according to any one of [1] to

[18] above fixed to the filter, or a filter device or an engine lubrication device provided with the filter part, or an automobile or a combustion device provided with these devices.

Examples

[0114] Hereinafter, the present technology will be described in more detail based on examples and the like. Note that the examples and the like described below show an example of typical examples of the present technology, and the scope of the present technology is not construed narrowly thereby.

[0115] 〔Test Example 1: Examination of (meth)acrylate-based photocurable composition〕 (1) Manufacturing method Each component shown in Tables 1 and 2 was weighed so as to have the composition shown in Tables 1 and 2 below, and stirred until they became uniform to obtain a photocurable composition. The unit of the numerical values in the table is parts by mass in all cases. The compound names of the materials shown in this example are as follows. Note that the molecular weights of oligomers and polymers can be measured and calculated by GPC analysis (weight average molecular weight), and the molecular weights of low molecules can be calculated by calculation from the composition.

[0116] The compounds used in Tables 1 and 2 are shown below. · [Mixed composition 1] A mixture obtained by mixing a mixed oligomer component (bifunctional polyester-based urethane acrylate; molecular weight 9,000; viscosity (BM viscometer at 60 ° C) 33,000 mPa·s) and a monofunctional monomer component (2-phenoxyethyl acrylate; molecular weight 192) at 65%:35% (concentration / concentration) (RUA-074, manufactured by Asahi Chemical Industry Co., Ltd.) The bifunctional polyester-based urethane acrylate is a polybutadiene-based urethane acrylate resin having (meth)acrylic groups at both ends of hydrogenated polybutadiene via urethane bonds. · [Bifunctional monomer] 1,6-Hexanediol diacrylate · [Trifunctional monomer] Trimethylolpropane ethoxy triacrylate · [Photopolymerization initiator] Photoinitiator A (α-hydroxyacetophenone type): 2-hydroxy-1-(4-(4-(2-hydroxy-2-methylpropionyl)benzyl)phenyl)-2-methylpropan-1-one Photoinitiator B (benzyl ketal type): 2,2-dimethoxy-2-phenylacetophenone (benzoyldimethyl ketal) Photoinitiator C (phosphine oxide type): 2,4,6-trimethylbenzoyldiphenylphosphine oxide

[0117] [Others] Defoaming polysiloxane-based defoamer Defoamer Curing accelerator (acrylated amine (bifunctional) (amino acrylate)) Hindered phenol-based antioxidant (4,6-bis(octylthiomethyl)-o-cresol)

[0118] <Test method (heat-resistant oil test)> · Immerse the test pieces of each test specimen in the engine oil in an explosion-proof container. Arrange them so that the entire test specimen is immersed. · Cover the explosion-proof container with the test specimens set inside and set it in an oil bath. · Immerse for a specified temperature and time. · After immersion, take out and allow to cool to room temperature (23 °C). Then, conduct each measurement. · Test conditions (immersion conditions) Test time: 135 °C × 96 h × 2 cycles Engine oil used: 10W-30 · Curing conditions Metal halide lamp (including ultraviolet wavelengths of 200 to 450 nm, with high output at 360 to 380 nm) 110 mW / cm^2, 1,000 mJ / cm^2

[0119] According to the <Measurement method of mass change rate [%]>, <Measurement method of volume change rate [%]>, <Measurement method of change in tensile strength [MPa]>, <Measurement method of change in elongation [%]>, <Measurement method of hardness in the normal state>, and <Measurement method of hardness after immersion> described above, each composition was evaluated, and the results are shown in Table 1 and Table 2. It can be said that the closer these evaluation points are to 0, the better the evaluation. Furthermore, Table 2 shows the total value of the absolute value of the value obtained by the <Measurement method of mass change rate [%]> and the absolute value of the value obtained by the <Measurement method of volume change rate [%]>. The smaller the total score of this is, the better it is judged. In the case of the same score, the one with the smaller change rate of tensile strength is judged to be better.

[0120] And, the smaller the mass change rate before and after the heat-resistant oil test, the less concern there is about oil absorption and elution of components, and the better it is. Therefore, the better this evaluation is, the more excellent the oil resistance of the cured product can be said to be. Also, the smaller the volume change rate before and after the heat-resistant oil test, the less or no expansion and contraction can be said, and the sealing property can be maintained as it is at the initial stage and is good. Therefore, the better this evaluation is, the more excellent the oil resistance and heat resistance of the cured product can be said to be. Furthermore, the less the change in tensile strength before and after the heat-resistant oil test, the more it is an item where both hardness and elongation are affected. The tensile strength before and after the heat-resistant oil test tends to be larger as it becomes harder and smaller as it becomes easier to stretch. Also, after hardness immersion, as shown by the · test conditions (immersion conditions), since it is immersed in high-temperature oil for a long time, the oil resistance can be evaluated by this. The higher the value, the better it is. If it is 55 or more and generally around 60, it can be said to pass as far as oil resistance is concerned.

[0121] From the results in Table 1, it was judged that the composition of Comparative Example 1, which had some cracks and did not contain a trifunctional monomer, was not preferable. Examples 1 and 2 contained an oligomer, a monofunctional monomer, a bifunctional monomer, and a trifunctional monomer, and further contained a photoinitiator, so they were excellent in oil resistance and heat-resistant oiliness, had a small mass change rate and volume change rate, and good cured products could be obtained. Furthermore, from the results in Table 2, Examples 9, 8, 3, 6, 5, and 7 were more excellent in that order, and Example 7 was the most excellent. Note that Example 3 has the same composition as Example 1, and Example 4 has the same composition as Example 2. For Example 3 in Table 2, the measured values of Example 1 in Table 1 are used, and for Example 4 in Table 2, the measured values of Example 2 in Table 1 are used.

[0122]

Table 1

[0123]

Table 2

[0124] 〔Test Example 2: Examination of filter parts for engine oil using (meth)acrylate-based photocurable compositions〕

[0125] Filter parts for engine oil were manufactured using the (meth)acrylate-based photocurable compositions of Example 7 and Example 3 according to the manufacturing methods shown in FIGS. 1 and 2 (「1-4.」[Examples of manufacturing methods]). The curing conditions were the same as in Test Example 1. The appearance of the composition of Example 7 was pale yellow and transparent, and its viscosity was 60,000 mPa·s at a BH-type viscometer (23 °C, 10 revolutions). The composition of Example 3 also had almost the same appearance and viscosity. For the composition of Example 7, almost no impregnation such as capillary action was observed even when a chrysanthemum-shaped engine oil filter was immersed, and it could be cured by light irradiation. For the composition of Example 3, almost no capillary action of the filter was observed either, and it could be cured.

[0126] Furthermore, the cured products of Example 7 and Example 3 each had a thickness of 20 mm or less, the appearance of the cured products was colorless and transparent, and as shown in the results of Table 2 above, they had appropriate hardness and were good as a support. As is clear from the results in Table 2 above, the properties (such as heat and oil resistance) of these cured products are excellent, and it is considered preferable to apply them in places where heat such as engine oil exists and oil is present or in contact with oil (for example, filter parts for engine oil, filter parts for fuel oil, etc.).

[0127] In addition, as a conventional product of parts for an engine oil filter, there is a cured product using a two-component thermosetting composition based on an epoxy resin. In contrast, the photocurable compositions of Example 7 and Example 3 are one-component types, so weighing and mixing operations are not required as compared with the epoxy-based two-component thermosetting composition, and thus the workability is good. In the case of the epoxy-based composition, it takes about 10 minutes for thermosetting, but the photocurable compositions of Example 7 and Example 3 can be cured in a much shorter time of about 30 seconds by UV irradiation. Further, these photocurable compositions can be easily peeled off from the mold after being put in a liquid state in a mold of a desired shape and photocured to obtain a desired shape, so that the material loss is small. Thus, the (meth)acrylate-based photocurable composition of the present invention has a great merit from the viewpoint of industrial production because the curing time is particularly short, leading to a short production time required.

Explanation of Symbols

[0128] 1 Photocurable composition; 3 Filter; 10 Cured product of photocurable composition; 101, 100 Filter parts

Claims

1. (A) A bifunctional polyester-based urethane (meth)acrylate oligomer, (B) A monofunctional (meth)acrylate monomer, (C) A bifunctional (meth)acrylate monomer, (D) A trifunctional or higher functional (meth)acrylate monomer, and (E) A photoinitiator, A photocurable composition comprising the same.

2. The photocurable composition according to claim 1, wherein the mass change rate before and after the heat-resistant oil test is in the range of -10 to +10%, and / or the volume change rate before and after the heat-resistant oil test is in the range of -10 to +10%.

3. The photocurable composition according to claim 1 or 2, wherein the (E) photoinitiator is a benzyl ketal-based compound.

4. The photocurable composition according to claim 1 or 2, wherein the (E) photoinitiator is an acetophenone-based compound.

5. The photocurable composition according to claim 1 or 2, wherein the (B) monofunctional (meth)acrylate monomer has a substituted or unsubstituted aryl group.

6. The photocurable composition according to claim 1 or 2, wherein the (B) monofunctional (meth)acrylate monomer is 2-phenoxyethyl acrylate.

7. The photocurable composition according to claim 1 or 2, wherein the (C) bifunctional (meth)acrylate monomer is alkylene glycol di(meth)acrylate.

8. The photocurable composition according to claim 1 or 2, wherein the (C) bifunctional (meth)acrylate monomer is 1,6-hexanediol diacrylate.

9. The photocurable composition according to claim 1 or 2, wherein the (D) trifunctional or higher functional (meth)acrylate monomer is trimethylol C2-C10 alkane alkoxy triacrylate.

10. The photocurable composition according to claim 1 or 2, wherein the (D) trifunctional or higher functional (meth)acrylate is trimethylolpropane ethoxy triacrylate.

11. The photocurable composition according to claim 1 or 2, wherein the cured product after curing of the photocurable composition has a hardness of 50 to 80 in the normal state and 50 to 80 after oil immersion.

12. The photocurable composition according to claim 1 or 2, wherein the composition is used as a fixing agent or an adhesive.

13. The photocurable composition according to claim 1 or 2, wherein the composition is used for fixing an oil filter.

14. The composition according to claim 1 or 2, which is used as a heat-resistant oil-cured product after curing.

15. A cured product of the photocurable composition according to claim 1 or 2.

16. A product comprising a cured product of the photocurable composition according to claim 1 or 2, wherein the cured product is one or more selected from a sealing material, a fixing material, and a supporting material, and the product is one or more selected from an automobile, an airplane, a ship, a combustion device, and a dust collector.

17. A filter component comprising a cured product of the photocurable composition according to claim 1 or 2.

18. A filter component comprising a filter for filtering fuel or oil and a cured product of the photocurable composition according to claim 1 or 2 adhered to the filter.

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