Classifications

• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
  • C08F2/00—Processes of polymerisation
  • C08F2/46—Polymerisation initiated by wave energy or particle radiation
  • C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
  • C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
  • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
  • C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
  • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
  • C08G59/68—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
  • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
  • C08G65/04—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers only
  • C08G65/06—Cyclic ethers having no atoms other than carbon and hydrogen outside the ring
  • C08G65/16—Cyclic ethers having four or more ring atoms
  • C08G65/18—Oxetanes

Definitions

• the present invention relates to a composition containing an acrylic compound, an epoxy compound, and a cationic polymerization initiator.
• compositions containing an acrylic compound and an epoxy compound and containing a cationic polymerization initiator are used in the fields of inks, paints, various coating agents, adhesives, optical members, etc.
• Various reports have been made on improvements to such curable compositions.
• Patent Document 1 describes a composition containing a radical polymerizable component (A) and a cationic polymerizable component (B), in which the radical polymerizable component (A) contains 70 to 100 parts by mass of a radical polymerizable compound (A1) having a crosslinked condensed ring per 100 parts by mass of the radical polymerizable component (A), and the cationic polymerizable component (B) contains 10 to 50 parts by mass of a cationic polymerizable compound (B1) having a crosslinked condensed ring per 100 parts by mass of the cationic polymerizable component (B).
• Patent Document 1 also describes that the composition described in the same document is excellent in adhesive strength and water resistance.
• Patent Document 1 has a high viscosity and poor coatability when attempting to improve the adhesiveness and moist heat resistance of the cured product, and that there is room for improvement in terms of the balance between adhesiveness, moist heat resistance, and viscosity.
• the problem that the present invention aims to solve is to provide a composition that has excellent adhesive properties and moist heat resistance of the cured product, and also has low viscosity.
• composition that contains a polyfunctional acrylic compound (A) having a condensed ring, a monofunctional acrylate compound (B), an epoxy compound (C), an oxetane compound (D), a cationic polymerization initiator (E) and a radical polymerization initiator (F), in which the epoxy compound (C) contains a predetermined amount of an epoxy compound (C1) having a condensed ring.
• a composition comprising a polyfunctional acrylic compound having a condensed ring (A), a monofunctional acrylate compound (B), an epoxy compound (C), an oxetane compound (D), a cationic polymerization initiator (E) and a radical polymerization initiator (F),
• the epoxy compound (C) contains an epoxy compound (C1) having a condensed ring, A composition in which the content of the epoxy compound (C1) relative to the epoxy compound (C) is 1 to 30 mass%.
• the polyfunctional acrylic compound (A) having a condensed ring is a compound (A1) having a tricyclodecane skeleton.
• An adhesive comprising the composition according to any one of [1] to [9].
• a method for producing a cured product comprising at least one of the steps of irradiating the composition according to any one of [1] to [10] with active energy rays and heating the composition according to any one of [1] to [10].
• the composition of the present invention is a composition containing a polyfunctional acrylic compound (A) having a condensed ring, a monofunctional acrylate compound (B), an epoxy compound (C), an oxetane compound (D), a cationic polymerization initiator (E) and a radical polymerization initiator (F), in which the epoxy compound (C) contains an epoxy compound (C1) having a condensed ring, and the content of the epoxy compound (C1) relative to the epoxy compound (C) is 1 to 30 mass%.
• the composition of the present disclosure also has excellent storage stability. As described in each of the examples below, the composition of the present disclosure has excellent curing properties, and the amount of polymerization initiator used can be kept below a certain amount. In addition, by containing a certain amount of a compound having a condensed ring, the cured product is less likely to be thermally denatured, and has excellent heat resistance.
• the polyfunctional acrylic compound (A) having a condensed ring means a compound having one or more condensed rings and a total number of acrylic and methacrylic groups of two or more in the molecule.
• condensed rings that open when cured and become a single ring such as alicyclic epoxy groups, are not counted as condensed rings. This is because condensed rings that become a single ring after curing cannot be expected to improve resistance to moist heat.
• the condensed rings include those that contain heteroatoms and those that do not (the same applies to the condensed rings of compounds (B1) and (C1) described below).
• the alicyclic epoxy group may also be called a cycloalkene oxide structure.
• the condensed ring of the compound (A) is preferably a bridged condensed ring in terms of improving the resistance to moist heat.
• the bridged condensed ring means a condensed ring sharing a hydrocarbon group having 3 or more carbon atoms, and is preferably an aliphatic ring.
• the bridged condensed ring is preferably a bridged condensed ring having a structure represented by the general formula (I) or an adamantane ring, and is particularly preferably a bridged condensed ring having a structure represented by the general formula (I).
• the hydrogen atoms on these rings can be substituted with any substituent.
• examples of monovalent substituents include halogen atoms, cyano groups, nitro groups, hydroxyl groups, thiol groups, -COOH, -SO 3 H, isocyanate groups, and alkyl groups having 1 to 4 carbon atoms.
• bridged fused rings in compound (A) is a bridged fused ring
• suitable examples of the bridged fused ring include bridged fused rings No. 1 to 12 shown below.
• a composition containing a compound (A1) having at least one condensed ring selected from bridged condensed rings No. 2 and No. 3 is preferred in that it has low viscosity and storage stability while also providing adhesive strength and resistance to moist heat.
• composition containing a compound (A1) (hereinafter also referred to as compound (A1)) having a tricyclodecane skeleton as compound (A) is preferred because it has excellent resistance to moist heat.
• Having a tricyclodecane skeleton means having a tricyclodecane ring in the structure, for example, having bridged condensed ring No. 2.
• the number of fused rings in compound (A) is preferably 5 or less, more preferably 3 or less, even more preferably 2 or less, and most preferably 1.
• the number of fused rings in the following formula (II) is 1.
• the total number of acrylic and methacrylic groups in compound (A) is preferably 2 to 5, more preferably 2 to 4, even more preferably 2 to 3, and most preferably 2.
• compound (A) be represented by the following formula (II).
• ring A is any one of the above bridged condensed rings No. 1 to 12, L1 and L2 are each independently a direct bond or an alkylene group having 1 to 3 carbon atoms, and R1 and R2 are each independently a hydrogen atom or a methyl group.
• the molecular weight of compound (A) is preferably 150 or more and less than 600, more preferably 200 or more and 400 or less, and even more preferably 250 or more and 350 or less.
• Examples of the compound (A) include tricyclodecane dimethanol di(meth)acrylate.
• the term "(meth)acrylate” refers to both the corresponding methacrylate and acrylate.
• tricyclodecane dimethanol di(meth)acrylate refers to both tricyclodecane dimethanol diacrylate and tricyclodecane dimethanol dimethacrylate.
• the compound (A1) commercially available products can be used, such as KAYARAD R-684 (both manufactured by Nippon Kayaku Co., Ltd.) and A-DCP (both manufactured by Shin-Nakamura Chemical Co., Ltd.).
• the content of compound (A) is preferably 5 to 70 parts by mass, more preferably 10 to 60 parts by mass, and particularly preferably 15 to 50 parts by mass, per 100 parts by mass of the solid content of the composition.
• the content of compound (A) is within the above range, a composition having a good balance between moist heat resistance and adhesiveness is obtained.
• the solid content of the composition means the components contained in the composition excluding the solvent.
• the content of compound (A1) is preferably 30 to 100 parts by mass, more preferably 40 to 100 parts by mass, and particularly preferably 50 to 100 parts by mass, per 100 parts by mass of compound (A).
• the content of compound (A1) is within the above range, a composition having a good balance between moist heat resistance and adhesiveness can be obtained.
• composition of the present invention may contain a polyfunctional acrylic compound that does not have a condensed ring (hereinafter also referred to as compound (A')).
• compound (A') examples include aliphatic polyfunctional acrylic compounds and polyfunctional acrylic compounds that have an isocyanurate ring.
• Aliphatic polyfunctional acrylic compounds are compounds that do not have an aromatic ring or a heterocyclic ring and have a total number of acrylic and methacrylic groups of 2 or more, and examples of such compounds include esters of unsaturated monobasic acids and polyhydric alcohols or polyhydric phenols, such as ethylene glycol di(meth)acrylate, diethylene glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, polyethylene glycol di(meth)acrylate, propylene glycol di(meth)acrylate, 1,4-butanediol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, 1,10-decanediol diacrylate, neopentyl glycol diacrylate, trimethylolethane tri(meth)acrylate, trimethylolpropane tri(meth)acrylate, dipentaerythritol hexa(meth)acrylate, pentaery
• polyfunctional acrylic compounds having an isocyanurate ring examples include tris[(meth)acryloxyalkyl]isocyanurates such as ⁇ -caprolactone-modified tris[2-(meth)acryloxyethyl]isocyanurate, tri[(meth)acryloylethyl]isocyanurate, and tris[3-(meth)acryloxypropyl]isocyanurate, as well as di[(meth)acryloylethyl]-2-hydroxyethyl isocyanurate and tri(acryloylethyl)isocyanurate.
• tris[(meth)acryloxyalkyl]isocyanurates such as ⁇ -caprolactone-modified tris[2-(meth)acryloxyethyl]isocyanurate, tri[(meth)acryloylethyl]isocyanurate, and tris[3-(meth)acryloxypropyl]isocyanurate, as well as di[
• aliphatic polyfunctional acrylic compounds include Kayarad DPHA, DPEA-12, PEG400DA, THE-330, RP-1040, NPGDA, and PET30 (all manufactured by Nippon Kayaku); NK Ester A-DOD-N, A-DPH, A-TMPT, A-HD-N, TMPT, A-NPG, and A-HD-N (all manufactured by Shin-Nakamura Chemical).
• polyfunctional acrylic compounds that have an isocyanurate ring but no condensed ring include Aronix M-215 and M-315 (both manufactured by Toagosei); NK Ester A-9300, A-9300-1CL, and A-9300-3CL (all manufactured by Shin-Nakamura Chemical Co., Ltd.); and Taik (manufactured by Mitsubishi Chemical).
• the content of compound (A') is preferably 50 mass % or less, more preferably 20 mass % or less, and may be 3 mass % or less, based on the solid content of the composition.
• the proportion of compound (A) in the entire polyfunctional acrylic compound is preferably 30% by mass or more, and more preferably 50% by mass or more.
• the monofunctional acrylate compound (B) (hereinafter also referred to as compound (B)) means a compound having one acrylic group or one methacrylic group.
• Examples of the compound (B) include a monofunctional acrylate compound (B1) having a condensed ring (hereinafter also referred to as compound (B1)), a monofunctional acrylate compound (B2) having a hydroxyl group (hereinafter also referred to as compound (B2)), and another monofunctional acrylate compound (B3) (hereinafter also referred to as compound (B3)).
• composition of the present invention contains compounds (A) and (C) to (F), and when (C1)/(C) is a specific ratio, the composition contains a monofunctional acrylate compound (B) to exhibit good adhesion, moist heat resistance, and low viscosity.
• the above compound (B1) refers to all monofunctional acrylate compounds having a condensed ring
• the above compound (B2) refers to monofunctional acrylates having no condensed ring and a hydroxyl group
• the above compound (B3) refers to monofunctional acrylate compounds other than compounds (B1) and (B2).
• Compositions containing compound (B1) are preferred because they have excellent resistance to moist heat.
• Compound (B1) refers to a compound that has one or more condensed rings in the molecule and has one acrylic or methacrylic group.
• condensed rings that open to become a single ring when cured such as alicyclic epoxy groups, are not counted as condensed rings. This is because condensed rings that become a single ring after curing are not expected to improve the moist heat resistance of the cured product.
• the fused ring in compound (B1) is preferably a bridged fused ring, in order to achieve a balance between low viscosity, moisture heat resistance, and adhesiveness.
• Suitable examples of the bridged fused ring include bridged fused rings having a structure represented by the above general formula (I).
• Examples of compound (B1) include dicyclopentanyloxyethyl (meth)acrylate, dicyclopentenyl (meth)acrylate, dicyclopentanyl (meth)acrylate, dicyclopentenyloxyethyl (meth)acrylate, isobornyl (meth)acrylate, norbornyl (meth)acrylate, dimethylol-tricyclodecane di(meth)acrylate, adamantane (meth)acrylate, 2-isopropyl-2-adamantyl (meth)acrylate, etc.
• commercially available products can also be used as compound (B1).
• Examples of commercially available products include DCP (all manufactured by Shin-Nakamura Chemical Co., Ltd.); FA-511AS, FA-512AS, FA-513AS, FA-512M, FA-512MT, and FA-513M (all manufactured by Hitachi Chemical Co., Ltd.).
• the fused ring contained in the compound (B1) may be the same as or different from that of the compound (A). In the case where it is different, a compound having a smaller number of rings constituting the fused ring than that of the compound (A) may be used.
• the number of rings constituting the fused ring referred to here means the number of rings contained in the fused ring, and if it is the bridged fused ring No. 1, it is 3, and if it is the bridged fused ring No. 2, it is 4.
• the fused ring contained in compound (B1) is preferably a norbornyl skeleton or a tricyclodecane skeleton, and more preferably at least one selected from bridged fused rings No. 1 and No. 2, and particularly preferably a compound having at least one selected from bridged fused rings No. 1 and No. 2, and particularly preferably bridged fused ring No. 1, with an isobornyl ring being most preferred.
• compound (B1) preferably has an acrylic group in terms of curability.
• a composition containing compound (B2) as the monofunctional acrylate compound (B) is preferred because it has excellent heat resistance.
• Compound (B2) means a compound that has no condensed rings in the molecule, has one acrylic or methacrylic group, and has one or more hydroxyl groups. The number of hydroxyl groups is preferably one, because it has low viscosity and good coatability.
• Examples of compound (B2) include hydroxyl group-containing acrylic esters such as hydroxyethyl (meth)acrylate, hydroxypropyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 2-hydroxyethyl (meth)acrylate, and 4-hydroxybutyl (meth)acrylate; hydroxyl group-containing acrylamides such as N-2-hydroxyethyl (meth)acrylamide; mono(meth)acrylate of ethylene glycol diglycidyl ether, diethylene glycol diglycidyl ether, and the like, which are produced by reacting an epoxy compound with (meth)acrylic acid.
• acrylic esters such as hydroxyethyl (meth)acrylate, hydroxypropyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 2-hydroxyethyl (meth)acrylate, and 4-hydroxybutyl (meth)acrylate
• hydroxyl group-containing acrylamides such as N-2-hydroxyethyl (
• epoxy (meth)acrylates include mono(meth)acrylates of ethylene glycol diglycidyl ether, mono(meth)acrylates of triethylene glycol diglycidyl ether, mono(meth)acrylates of polyethylene glycol diglycidyl ether, mono(meth)acrylates of propylene glycol diglycidyl ether, mono(meth)acrylates of tripropylene glycol diglycidyl ether, mono(meth)acrylates of polypropylene glycol diglycidyl ether, and mono(meth)acrylates of neopentyl glycol diglycidyl ether.
• composition of the present invention may contain compound (B3) as compound (B).
• Examples of compound (B3) include glycidyl (meth)acrylate, the following compounds No. 1 to No. 4, and (3-ethyloxetan-3-yl)methyl acrylate.
• Other compounds (B3) include, for example, (meth)acrylic acid; unsaturated succinic acid mono[2-(meth)acryloyloxyethyl], phthalic acid mono[2-(meth)acryloyloxyethyl]; methyl (meth)acrylate, butyl (meth)acrylate, isobutyl (meth)acrylate, t-butyl (meth)acrylate, cyclohexyl (meth)acrylate, n-octyl (meth)acrylate, isooctyl (meth)acrylate, isononyl (meth)acrylate, stearyl (meth)acrylate, lauryl (meth)acrylate, methoxyethyl (meth)acrylate, dimethylaminomethyl (meth)acrylate, di(meth)acrylate,
• esters include esters of unsaturated monobasic acids and monohydric alcohols or monohydric phenols such as methylamino
• Other compounds B3 may also be commercially available.
• Examples of commercially available products include NK Ester AM-90G, AM-90G, AM-130G, AM-230G, and AMP-20GY (all manufactured by Shin-Nakamura Chemical Co., Ltd.), ⁇ -CEA, EBECRYL 110, and EBECRYL 110 (all manufactured by Daicel Ornix), and THFA (all manufactured by Osaka Organic Chemicals).
• the compound (B) preferably contains at least one selected from the compounds (B1) and (B2).
• the content of compound (B) is preferably 3 to 70 parts by mass, more preferably 5 to 60 parts by mass, and particularly preferably 8 to 50 parts by mass, per 100 parts by mass of the solid content of the composition.
• the content of compound (B) is within the above range, a composition having a good balance between moist heat resistance and adhesiveness is obtained.
• the solid content of the composition means the components contained in the composition excluding the solvent.
• the content of compound (B1) is preferably 30 to 100 parts by mass, more preferably 40 to 90 parts by mass, and particularly preferably 50 to 80 parts by mass, per 100 parts by mass of compound (B).
• the content of compound (B1) is within the above range, a composition having a good balance between moist heat resistance and adhesiveness can be obtained.
• the mass ratio of the content of compound (A) to compound (B1) is preferably 2 parts by mass or more and 200 parts by mass or less of compound (B1) per 100 parts by mass of compound (A), and from the viewpoint of a balance between low viscosity, storage stability, adhesion, and moist heat resistance, and particularly from the viewpoint of excellent curing properties and particularly excellent adhesion, it is more preferably 3 parts by mass or more and 80 parts by mass or less, and even more preferably 5 parts by mass or more and 30 parts by mass or less.
• the content of compound (B2) is preferably 5 to 100 parts by mass, more preferably 10 to 80 parts by mass, and particularly preferably 30 to 60 parts by mass, per 100 parts by mass of compound (B).
• the content of compound (B2) is within the above range, a composition having a good balance of low viscosity, moist heat resistance, and adhesiveness can be obtained.
• the present disclosure relates to a composition in which compound (C) contains an epoxy compound (C1) (hereinafter also referred to as compound (C1)) having a condensed ring, which provides a composition with a good balance between moist heat resistance and adhesion.
• compound (C1) an epoxy compound (hereinafter also referred to as compound (C1)) having a condensed ring
• Compound (C1) is an epoxy compound having a condensed ring.
• a bridged condensed ring having a structure represented by the above general formula (I) is preferred because it has excellent resistance to moist heat.
• the compound (C1) is preferably a compound represented by any one of the following formulas (IV-1) to (IV-3).
• Ring C is any one of the above bridged fused rings No. 1 to 12, and L4 and L5 each independently represent a direct bond or an alkylene group having 1 to 3 carbon atoms.
• ring D is any one of the above bridged fused rings No. 1 to 12, and L6 is a direct bond or an alkylene group having 1 to 3 carbon atoms.
• the alkylene group having 1 to 3 carbon atoms includes a methylene group, an ethylene group, and a propylene group.
• ring E is any one of the bridged fused rings No. 1 to 12 described above.
• Specific examples of the compound (C1) represented by any of formulas (IV-1) to (IV-3) include the following compounds (C1) No. 1 to No. 14.
• ADEKA RESIN EP-4088L and 4088S both manufactured by ADEKA
• XD-1000 manufactured by Nippon Kayaku
• HP-7200 manufactured by DIC
• KRM-408 manufactured by ADEKA
• the epoxy group of compound (C1) is preferably a glycidyl ether group, from the viewpoint of high curability and excellent adhesive strength.
• composition containing the compound (C1) having the above bridged condensed ring No. 2 or No. 3 is preferred because it has low viscosity, high adhesive strength, and moist heat resistance, and the composition containing the compound (C1) containing the bridged condensed ring No. 2 is preferred.
• the compound (C2) include monofunctional epoxy compounds such as glycidyl ethers of aliphatic alcohols and glycidyl esters of alkylcarboxylic acids, and polyfunctional epoxy compounds such as polyglycidyl ethers of aliphatic polyhydric alcohols or their alkylene oxide adducts, and polyglycidyl esters of aliphatic long-chain polybasic acids.
• linear epoxy compound examples include glycidyl ethers of polyhydric alcohols such as 1,4-butanediol diglycidylate, allyl glycidyl ether, butyl glycidyl ether, 2-ethylhexyl glycidyl ether, C12-13 mixed alkyl glycidyl ether, 1,4-butanediol diglycidyl ether, 1,6-hexanediol diglycidyl ether, glycerin triglycidyl ether, trimethylolpropane triglycidyl ether, sorbitol tetraglycidyl ether, dipentaerythritol hexaglycidyl ether, polyethylene glycol diglycidyl ether, and polypropylene glycol diglycidyl ether; polyglycidyl ethers of polyether polyols obtained by adding one or more al
• Further examples include monoglycidyl ethers of higher aliphatic alcohols, glycidyl esters of higher fatty acids, epoxidized soybean oil, epoxy octyl stearate, epoxy butyl stearate, epoxidized soybean oil, and epoxidized polybutadiene.
• compound (C2) commercially available products can be used, for example, Denacol EX-121, Denacol EX-171, Denacol EX-192, Denacol EX-211, Denacol EX-212, Denacol EX-313, Denacol EX-314, Denacol EX-321, Denacol EX-411, Denacol EX-421, Denacol EX- 512, Denacol EX-521, Denacol EX-611, Denacol EX-612, Denacol EX-614, Denacol EX-622, Denacol EX-810, Denacol EX-811, Denacol EX-850, Denacol EX-851, Denacol EX-821, Denacol EX-830, Denacol EX-832, Denacol EX-841, Denacol Denacol EX-861, Denacol EX-911, Denacol EX-941, Denacol EX-920, Denacol EX-931 (all manufactured by
• the chain of the compound (C2) is a branched chain.
• the compound (C2) is a compound having a structure in which a branched chain alcohol is glycidyl etherified.
• the linear epoxy compound (C2) is a compound having a structure obtained by glycidyl etherifying a linear alcohol
• the linear alcohol is preferably one having 3 to 10 carbon atoms, and more preferably one having 3 to 8 carbon atoms.
• a compound having a structure obtained by glycidyl etherifying a branched linear alcohol having the above number of carbon atoms is particularly preferred.
• the epoxy group of compound (C2) is preferably a glycidyl ether group, from the viewpoint of high curability and excellent adhesive strength.
• Compound (C) may be any other epoxy compound other than compound (C1) and compound (C2).
• other epoxy compounds include aromatic epoxy compounds.
• Aromatic epoxy compounds refer to compounds that have an aromatic ring and do not have an alicyclic epoxy group. Examples of aromatic epoxy compounds include those described in WO 2020/045358, and bisphenol A type epoxy compounds, bisphenol F type epoxy compounds, bisphenol E type epoxy compounds, or phenol novolac type epoxy compounds are preferred because of their excellent adhesive strength.
• compound (C) does not contain an epoxy compound having an alicyclic epoxy group, since the adhesive strength is better.
• epoxy compounds having an alicyclic epoxy group include those exemplified in WO 2020/045358.
• the content of the epoxy compound having an alicyclic epoxy group in compound (C) is preferably 1 mass% or less.
• an epoxy compound has a molecular weight of more than 2,000, the compound is treated as an epoxy polymer that does not fall under any of compound (C1), compound (C2), aromatic epoxy compounds, and alicyclic epoxy compounds.
• the molecular weight referred to here is the weight average molecular weight, which will be explained later.
• the content of the epoxy polymer in the composition is preferably less than 5 mass%, more preferably less than 4 mass%, and particularly preferably less than 3 mass%.
• the content of compound (C) is preferably 5 to 70 parts by mass, more preferably 10 to 60 parts by mass, and particularly preferably 20 to 50 parts by mass, per 100 parts by mass of the solid content of the composition.
• the content of compound (C) is within the above range, a composition having a good balance between moist heat resistance and adhesiveness can be obtained.
• the content of compound (C1) is 1 to 30% by mass relative to compound (C).
• the content of compound (C1) is more preferably 5 to 30% by mass relative to compound (C), and particularly preferably 10 to 30% by mass.
• the mass ratio of the content of compound (A) to compound (C1) is preferably 2 parts by mass or more and 200 parts by mass or less of compound (C1) per 100 parts by mass of compound (A), more preferably 3 parts by mass or more and 80 parts by mass or less, and particularly preferably 5 parts by mass or more and 30 parts by mass or less.
• the content of compound (C1) is preferably 0.1 to 20 parts by mass, more preferably 0.5 to 20 parts by mass, and particularly preferably 1 to 10 parts by mass, per 100 parts by mass of the solid content of the composition.
• the content of compound (C2) is preferably 15 to 90 parts by mass, more preferably 30 to 80 parts by mass, and particularly preferably 50 to 70 parts by mass, per 100 parts by mass of compound (C).
• the content of compound (C2) is within the above range, a composition having a good balance between moist heat resistance and adhesiveness can be obtained.
• the content of compound (C2) is preferably 180 to 1200 parts by mass, more preferably 200 to 1000 parts by mass, and particularly preferably 250 to 900 parts by mass, per 100 parts by mass of compound (C1).
• Oxetane compound (D) (hereinafter also referred to as compound (D)) is a compound that does not have an acrylic group, a methacrylic group, or an epoxy group in the molecule, but has an oxetanyl group.
• the composition of the present invention contains compounds (A) to (C), (E), and (F), and by containing oxetane compound (D) under the condition that (C1)/(C) is a specific ratio, the initial curing property is enhanced and a good balance of low viscosity, adhesion, and moist heat resistance is achieved.
• oxetane compound examples include 3,3'-[oxybis(methylene)]bis(3-ethyloxetane), (3,7-bis(3-oxetanyl)-5-oxa-nonane, 1,4-bis[(3-ethyl-3-oxetanylmethoxy)methyl]benzene, 1,2-bis[(3-ethyl-3-oxetanylmethoxy)methyl]ethane, 1,3-bis[(3-ethyl-3-oxetanylmethoxy)methyl]propane, ethylene glycol bis(3-ethyl-3-oxetanylmethyl)ether, triethylene glycol bis(3-ethyl-3-oxetanylmethyl)ether, tetraethylene glycol bis(3-ethyl-3-oxetanyl bifunctional oxetane compounds such as 1,4-bis(3-ethyl-3-oxetanylme
• oxetane compound commercially available products can be used, and examples thereof include ARON OXETANE OXT-121, OXT-101, OXT-221, EXOH, POX, PHO, OXA, XDO, OXT-101, OXT-211, and OXT-212 (manufactured by Toagosei Co., Ltd.), Ethanacole OXBP, and OXTP (manufactured by Ube Industries, Ltd.).
• Compound (D) may be a compound containing a hydroxyl group or a compound not containing a hydroxyl group. It may also be a compound having an aromatic ring or a compound not having an aromatic ring. Compound (D) is preferably a compound in which the hydrogen atom in an aliphatic hydrocarbon compound which may have an oxygen atom in the group is replaced with an oxetanyl group. The molecular weight of compound (D) is preferably 100 or more and less than 1,000, more preferably 150 or more and 400 or less.
• the number of oxetanyl groups in compound (D) is usually 1 to 3, but compositions in which compound (D) has two or more oxetanyl groups are particularly preferred because of their excellent adhesive properties.
• the content of compound (D) is preferably 0.1 to 30 parts by mass, more preferably 1 to 20 parts by mass, and particularly preferably 3 to 15 parts by mass, per 100 parts by mass of the solid content of the composition.
• the content of compound (D) is within the above range, a composition having a good balance between moist heat resistance and adhesiveness can be obtained.
• the content of compound (D) is preferably 20 parts by mass or more and 200 parts by mass or less, and more preferably 50 parts by mass or more and 150 parts by mass or less, per 100 parts by mass of compound (C1).
• the cationic polymerization initiator (E) (hereinafter also referred to as component (E)) is a material that generates an acid by active energy rays or heat. Both a photocationic polymerization initiator and a thermal cationic polymerization initiator can be used as component (E).
• a composition that is a photocationic polymerization initiator (E1) is preferred because it has a short curing time and enables patterning.
• the photocationic polymerization initiator (E1) is a material that generates an acid by active energy rays such as ultraviolet rays.
• component (E) preferably contains a compound having an aromatic ring, the number of aromatic rings being 3 or more.
• a photocationic polymerization initiator a double salt of an onium salt or its derivative, or an oxime sulfonate compound, a halogen-containing compound, a diazoketone compound, a sulfone compound, a sulfonic acid compound, a diazomethane compound, a nitrobenzyl compound, a benzoin tosylate compound, an iron arene complex, an acetophenone derivative compound, etc. can be used, and among them, a double salt of an onium salt or its derivative is preferable.
• the composition of the present invention has excellent curing speed and adhesive strength.
• compounds having three or more aromatic rings include salts of a cation and anion represented by the following general formula (1).
• the cation [A] m+ is preferably an onium, and the structure thereof can be represented, for example, by the following general formula (2).
• R 10 is an organic group having 1 to 60 carbon atoms and may contain any number of atoms other than carbon atoms.
• a is an integer from 1 to 5.
• a R 10 's are each independent and may be the same or different.
• At least one of the a R 10 is the above organic group having an aromatic ring, and the number of aromatic rings contained in the a R 10 is 3 or more.
• Q is an atom or atomic group selected from the group consisting of S, N, Se, Te, P, As, Sb, Bi, O, I, Br, Cl, and F.
• m a - q holds.
• the anion [B] m ⁇ is preferably a halide complex, and the structure thereof can be represented, for example, by the following general formula (3).
• L is a metal or semimetal (Metalloid) that is the central atom of the halide complex, and is B, P, As, Sb, Fe, Sn, Bi, Al, Ca, In, Ti, Zn, Sc, V, Cr, Mn, Co, etc.
• X is a halogen atom.
• b is an integer of 3 to 7.
• anion [LX b ] m- of general formula (3) examples include tetrakis(pentafluorophenyl)borate [(C 6 F 5 ) 4 B] ⁇ , tetrafluoroborate (BF 4 ) ⁇ , hexafluorophosphate (PF 6 ) ⁇ , hexafluoroantimonate (SbF 6 ) ⁇ , hexafluoroarsenate (AsF 6 ) ⁇ , hexachloroantimonate (SbCl 6 ) ⁇ , and tris(pentafluoromethyl)trifluorophosphate ion (FAP anion).
• the anion [B] m ⁇ may preferably have a structure represented by the following general formula (4).
• L, X, and b are the same as above.
• Other usable anions include perchlorate ion (ClO 4 ) ⁇ , trifluoromethylsulfite ion (CF 3 SO 3 ) ⁇ , fluorosulfonate ion (FSO 3 ) ⁇ , toluenesulfonate anion, trinitrobenzenesulfonate anion, camphorsulfonate, nonafluorobutanesulfonate, hexadecafluorooctane sulfonate, tetraarylborate, and tetrakis(pentafluorophenyl)borate.
• an aromatic iodonium salt compound or an aromatic sulfonium salt compound in terms of excellent adhesiveness, and an aromatic sulfonium salt compound is particularly preferable.
• An example of an aromatic iodonium salt compound is a diaryliodonium salt having a structure in which two aryl groups are bonded to an iodine atom.
• An example of an aromatic sulfonium salt compound is a triarylsulfonium salt having a structure in which three aryl groups are bonded to a sulfur atom.
• aromatic iodonium salt compounds and aromatic sulfonium salt compounds include the compounds described in JP 2019-070106 A, JP 2018-165330 A, and JP 2016-038569 A.
• the content of the cationic polymerization initiator (E) is preferably 0.1 to 20 parts by mass, more preferably 1 to 15 parts by mass, and particularly preferably 3 to 10 parts by mass, per 100 parts by mass of the solid content of the composition, from the viewpoint of optical properties, particularly from the viewpoint of improving the optical properties of the cured product.
• the radical polymerization initiator (F) is a material that generates radicals by activation energy rays, etc.
• the photoradical polymerization initiator (F1) is a material that generates radicals by light such as ultraviolet rays.
• the photoradical polymerization initiator (F1) is not particularly limited as long as it generates radicals upon irradiation with light, and any conventionally known compound can be used. Preferred examples include acetophenone-based compounds, benzyl-based compounds, benzophenone-based compounds, thioxanthone-based compounds, and oxime ester-based compounds.
• Acetophenone compounds include, for example, hydroxyacetophenone compounds such as 1-hydroxycyclohexyl phenyl ketone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, 1-[4-(2-hydroxyethoxy)-phenyl]-2-hydroxy-2-methyl-1-propan-1-one, 4'-isopropyl-2-hydroxy-2-methylpropiophenone, 2-hydroxymethyl-2-methylpropiophenone, and benzoin; alkoxyacetophenone compounds such as diethoxyacetophenone and 2,2-dimethoxy-1,2-diphenylethane-1-one.
• hydroxyacetophenone compounds such as 1-hydroxycyclohexyl phenyl ketone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, 1-[4-(2-hydroxyethoxy)-phenyl]-2-hydroxy-2-methyl-1-propan-1-one, 4'-isopropyl-2-hydroxy-2-methylpropiophenone, 2-hydroxymethyl-2-methyl
• acetophenone compounds include p-dimethylaminoacetophenone, p-tert-butyldichloroacetophenone, p-tert-butyltrichloroacetophenone, p-azidobenzalacetophenone, 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butanone-1, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin-n-butyl ether, benzoin isobutyl ether, and 2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropanone-1-one.
• hydroxyacetophenone compounds refer to acetophenone compounds in which a hydroxyl group is bonded to the carbon atom adjacent to the carbonyl group
• alkoxyacetophenone compounds refer to acetophenone compounds in which an alkoxy group is bonded to the carbon atom adjacent to the carbonyl group
• aminoacetophenone compounds refer to acetophenone compounds in which an amino group is bonded to the carbon atom adjacent to the carbonyl group
• other acetophenone compounds refer to acetophenone compounds that are not classified as hydroxyacetophenone compounds, alkoxyacetophenone compounds, or aminoacetophenone compounds.
• benzyl compounds examples include benzyl.
• benzophenone compounds include benzophenone, o-benzoylmethylbenzoate, Michler's ketone, 4,4'-bisdiethylaminobenzophenone, 4,4'-dichlorobenzophenone, and 4-benzoyl-4'-methyldiphenyl sulfide.
• thioxanthone compounds include thioxanthone, 2-methylthioxanthone, 2-ethylthioxanthone, 2-chlorothioxanthone, 2-isopropylthioxanthone, and 2,4-diethylthioxanthone.
• the oxime ester compound means a compound having an oxime ester group, and examples of the compounds described in WO 2020/045358 include the compounds described in WO 2020/045358.
• photoradical polymerization initiator (F1) examples include phosphine oxide compounds such as bis(2,4,6-trimethylbenzoyl)-phenylphosphine oxide, bis-(2,6-dimethoxybenzoyl)-2,4,4-trimethylpentylphosphine oxide, 2,4,6-trimethylbenzoyldiphenylphosphine oxide, bis(2,6-dimethylbenzoyl)-phenylphosphine oxide, bis(2,4,6-trimethylbenzoyl)-isobutylphosphine oxide, bis(2,6-dimethoxybenzoyl)-isobutylphosphine oxide, and bis(2,6-dimethoxybenzoyl)-phenylphosphine oxide, as well as titanocene compounds such as bis(cyclopentadienyl)-bis[2,6-difluoro-3-(pyrrol-1-yl)]titanium.
• titanocene compounds such
• Phosphine oxide compounds are preferred because they absorb in the long wavelength range and have high curing properties.
• photoradical polymerization initiators include ADEKA OPTOMER N-1414, N-1717, N-1919, ADEKA ARCLES NCI-831, NCI-930 (all manufactured by ADEKA); IRGACURE 184, IRGACURE 369, IRGACURE 651, IRGACURE 819, IRGACURE 907, IRGACURE OXE 01, IRGACURE OXE 02, IRGACURE 784 (all manufactured by BASF); TR-PBG-304, TR-PBG-305, TR-PBG-309, and TR-PBG-314 (all manufactured by Tronly).
• Acetophenone compounds are preferred because the resulting cured product has excellent transparency, and are more preferred than hydroxyacetophenone and alkoxyacetophenone compounds in which an oxygen atom is adjacent to a carbon atom adjacent to a carbonyl group, because they do not inhibit the cationic polymerization of epoxy compounds. Hydroxyacetophenone compounds are particularly preferred because they have excellent curing properties.
• the radical polymerization initiator (F) can be used alone or in combination of two or more of the above-mentioned examples.
• the content of the radical polymerization initiator (F) is preferably from 0.1 to 20 parts by mass, more preferably from 0.5 to 10 parts by mass, and particularly preferably from 1 to 5 parts by mass, per 100 parts by mass of the solid content of the composition.
• the content of the radical polymerization initiator (F) is within the above range, a composition having excellent optical properties, capable of providing a cured product with good optical properties, and having a good balance between moist heat resistance and adhesiveness can be obtained.
• a solvent (G) can further be added to the composition of the present invention.
• Solvent (G) is a compound that is liquid at 25°C and 1 atmosphere and does not fall under any of the above components. Generally, a solvent that can dissolve or disperse each of the above components can be used as necessary.
• ketones such as methyl ethyl ketone, methyl amyl ketone, diethyl ketone, acetone, methyl isopropyl ketone, methyl isobutyl ketone, cyclohexanone, and 2-heptanone
• ether-based solvents such as ethyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane, and dipropylene glycol dimethyl ether
• ester-based solvents such as methyl acetate, ethyl acetate, n-propyl acetate, isopropyl acetate, n-butyl acetate, cyclohexyl acetate, ethyl lactate, dimethyl succinate, and texanol
• cellosolve-based solvents such as ethylene glycol monomethyl ether and ethylene glycol monoethyl ether
• Solvents halogenated aliphatic hydrocarbon solvents such as carbon tetrachloride, chloroform, trichloroethylene, methylene chloride, and 1,2-dichloroethane; halogenated aromatic hydrocarbon solvents such as chlorobenzene; carbitol-based solvents, aniline, triethylamine, pyridine, acetic acid, acetonitrile, carbon disulfide, N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, dimethylsulfoxide, and water. These solvents can be used alone or in combination.
• halogenated aliphatic hydrocarbon solvents such as carbon tetrachloride, chloroform, trichloroethylene, methylene chloride, and 1,2-dichloroethane
• halogenated aromatic hydrocarbon solvents such as chlorobenzene
• carbitol-based solvents aniline, triethylamine,
• alcohols capable of cationic polymerization with epoxy compounds are preferred because of their excellent curability, and solvents with a boiling point of 200°C or higher that are low in volatility are preferred because of their excellent moldability (dimensional stability, less air bubbles).
• a composition that does not contain a solvent is particularly preferred.
• the solvent content is preferably 20 parts by mass or less, more preferably 10 parts by mass or less, and particularly preferably 5 parts by mass or less, per 100 parts by mass of the composition.
• the content is preferably 0.1 parts by mass or more per 100 parts by mass of the composition. This is because when the solvent content is within the above range, a composition with a good balance between moist heat resistance and adhesiveness can be obtained.
• the content of the polyfunctional acrylic compound (A) and the monofunctional acrylate compound (B) is preferably in the range of 20 to 90 parts by mass, more preferably 30 to 80 parts by mass, and particularly preferably 40 to 70 parts by mass, per 100 parts by mass of the total of the polyfunctional acrylic compound (A) having a condensed ring, the monofunctional acrylate compound (B), the epoxy compound (C), and the oxetane compound (D) (hereinafter also referred to as the polymerizable compound).
• the content of the radically polymerizable compound is in the above range, excellent adhesion is achieved.
• the content of the epoxy compound (C) and the oxetane compound (D) (hereinafter also referred to as cationic polymerizable compound) is preferably 10 to 80 parts by mass, more preferably 20 to 70 parts by mass, and particularly preferably 30 to 60 parts by mass, per 100 parts by mass of the total of the polymerizable compounds. This is because when the content of the cationic polymerizable compound is within the above range, the adhesiveness and moist heat resistance are excellent.
• a composition containing 95% by mass or more of components with a molecular weight of 2,000 or less is preferred because it has low viscosity and excellent coatability, and in particular, it is preferred that the composition contains 96% by mass or more of components with a molecular weight of 2,000 or less, and more preferably 97% by mass or more.
• the molecular weight referred to here can be measured as the weight average molecular weight in the case of polymeric compounds.
• the weight average molecular weight can be determined as a standard polystyrene equivalent value by gel permeation chromatography (GPC).
• the weight average molecular weight Mw can be obtained, for example, by using a GPC (LC-2000plus series) manufactured by JASCO Corporation, using tetrahydrofuran as the elution solvent, polystyrene standards for the calibration curve with Mw of 1,110,000, 707,000, 397,000, 189,000, 98,900, 37,200, 13,700, 9,490, 5,430, 3,120, 1,010, and 589 (TSKgel standard polystyrene manufactured by Tosoh Corporation), and measuring columns of KF-804, KF-803, and KF-802 (manufactured by Showa Denko K.K.).
• the measurement temperature can be 40°C
• the flow rate can be 1.0 mL/min.
• the composition of the present invention preferably has a viscosity of 40 mPa ⁇ s or less, since it has a low viscosity and is easy to handle.
• the viscosity is measured at 25°C by the method described in the Examples below. The lower the viscosity of the composition, the more preferable it is, but it is usually 10 mPa ⁇ s or more.
• a composition containing 20 to 90% by mass of a compound having a fused ring is preferred because it has an excellent balance of moist heat resistance, low viscosity, and adhesiveness, and has good heat resistance, and a content of 30 to 75% by mass in the composition is more preferred, and a content of 40 to 60% by mass is even more preferred.
• the fused ring referred to here includes the fused rings described in the description of compound (A).
• the composition of the present invention may contain other components as necessary in addition to the above components.
• the other components may contain various resin additives such as inorganic fillers, organic fillers, pigments, silane coupling agents, colorants such as dyes, photosensitizers, defoamers, thickeners, thixotropic agents, surfactants, leveling agents, flame retardants, plasticizers, stabilizers, polymerization inhibitors, ultraviolet absorbers, antioxidants, antistatic agents, flow control agents, and adhesion promoters as necessary.
• the total content of the other components is preferably 30% by mass or less in the solid content of the composition of the present invention.
• the method for producing the composition of the present invention is not particularly limited as long as it is a method that can uniformly mix the above-mentioned components.
• a method using a known mixing device can be adopted, such as a method using a three-roll mill, a sand mill, a ball mill, etc.
• the curing method of the composition of the present invention is appropriately set depending on the types of component (E) and component (F).
• component (E) and component (F) are a photocationic polymerization initiator (E1) and a photoradical polymerization initiator (F1), respectively
• the curing method can be a method of performing an active energy ray irradiation treatment in which the composition of the present invention is irradiated with active energy rays.
• active energy rays include visible light, ultraviolet light, electron beams, X-rays, radiation, and high frequency waves, with ultraviolet light being the most economically preferable.
• sources of ultraviolet light include ultraviolet lasers, mercury lamps, xenon lasers, and metal halide lamps.
• the composition of the present invention can be cured by irradiation with an LED light source.
• active energy rays from an LED light source include ultraviolet light.
• wavelengths of active energy rays from an LED light source include 350 nm to 405 nm.
• the cationic polymerization initiator is a photocationic polymerization initiator
• the composition of the present invention can be cured by irradiation with active energy rays to a touch-dry state or a solvent-insoluble state usually after 0.1 seconds to several minutes.
• the composition of the present invention can be cured by a heat treatment.
• the conditions for curing the composition of the present invention by heating can be 70°C to 250°C for 1 to 100 minutes. After pre-baking (PAB; Pre applied bake), pressure can be applied and then post-baked (PEB; Post exposure bake), or baking can be performed at several different temperatures.
• the heating conditions vary depending on the type and mixing ratio of each component, but can be, for example, 70°C to 180°C for 5 to 15 minutes in an oven or 1 to 5 minutes on a hot plate. After that, in order to cure the coating, a cured film can be obtained by heating at 180°C to 250°C, preferably 200°C to 250°C, for 30 to 90 minutes in an oven or 5 to 30 minutes on a hot plate.
• composition of the present invention are not particularly limited as long as they are used after forming a cured product, and include optical films, adhesives, glasses, optical materials such as imaging lenses, paints, coatings, linings, inks, high refractive index materials, water-soluble materials, resists for semiconductors, displays, MEMS, and medical devices, liquid resists, printing plates, insulating varnishes, insulating sheets, laminates, printed circuit boards, sealants for semiconductor devices, LED packages, liquid crystal injection ports, organic electroluminescence, optical elements, electrical insulation, electronic components, and separation membranes, molding materials, putties, glass fiber impregnating agents, fillers, passivation films for semiconductors and solar cells, interlayer insulating films, protective films, protective films for color filters, and other applications.
• optical films adhesives, glasses, optical materials such as imaging lenses, paints, coatings, linings, inks, high refractive index materials, water-soluble materials, resists for semiconductors, displays, MEMS, and medical devices, liquid resists, printing plates,
• the composition of the present invention is preferably used as an adhesive from the viewpoint of excellent coating properties and storage stability due to its resistance to moist heat and adhesion, and its low viscosity.
• Specific applications of the adhesive include optical materials such as glasses and imaging lenses, electronic material applications such as laminates and printed circuit boards, in-vehicle devices such as head-up displays and car navigation systems, and display panels such as organic electroluminescence and liquid crystal. It is particularly preferably used in applications requiring transparency, and is particularly preferably used in applications such as optical materials, in-vehicle devices, and display panels.
• the adherend to be adhered with the adhesive of the present invention may be either an inorganic material or an organic material.
• organic materials include cellulose esters such as diacetyl cellulose, triacetyl cellulose (TAC), propionyl cellulose, butyryl cellulose, acetylpropionyl cellulose, and nitrocellulose; polyamides; polyimides; polyurethanes; epoxy compounds; polycarbonates; polyesters such as polyethylene terephthalate, polyethylene naphthalate, polybutylene terephthalate, poly-1,4-cyclohexanedimethylene terephthalate, polyethylene-1,2-diphenoxyethane-4,4'-dicarboxylate, and polybutylene terephthalate; polystyrene; polyolefins such as polyethylene, polypropylene, polymethylpentene, polytetrafluoroethylene, and cycloolefin polymers; vinyl compounds
• the adhesive of the present invention contains the composition of the present invention.
• the adhesive of the present invention is excellent in curing speed, adhesive strength, and moist heat resistance.
• the adhesive of the present invention can be manufactured using the composition of the present invention.
• the adhesive of the present invention may consist of only the composition of the present invention, and can be manufactured by mixing the composition of the present invention with various additives known to be used in manufacturing adhesives using a known mixing device. Note that the uses of the composition and adhesive of the present invention can be the same as those described in the section on the composition, and therefore the description here is omitted.
• the cured product of the present invention is a cured product of the composition of the present invention.
• the cured product of the present invention can be used, for example, as an adhesive layer having excellent curing speed and adhesive strength. Note that the composition of the present invention can be the same as that described in the "Composition" section, so the description here is omitted.
• the cured product of the present invention is a cured product of the composition of the present invention and includes a polymer of the composition of the present invention. That is, the cured product of the present invention has a crosslinked condensed ring. The planar shape, thickness, etc.
• the cured product of the present invention can be appropriately set depending on the application of the cured product, etc.
• the cured product of the present invention is obtained by forming the composition of the present invention into a desired shape and curing it, and the manufacturing method is not particularly limited.
• Such a manufacturing method can be, for example, the same as that described in the section on the manufacturing method of the cured product below, and therefore the description here is omitted.
• the uses of the cured product of the present invention may be the same as those described in the section on the composition.
• the method for producing a cured product of the present invention includes a curing step of curing the composition of the present invention. Each step of the method for producing a cured product of the present invention will be described in detail below.
• the curing step is a step of curing the composition of the present invention, and includes a step of irradiating with active energy rays or heating. Such a curing method may be the same as that described in the section "A. Composition".
• the method for producing a cured product of the present invention may include other steps as necessary. Examples of such steps include a step of applying the composition of the present invention before a step of curing the composition of the present invention.
• the composition of the present invention can be applied by known methods such as a spin coater, a roll coater, a bar coater, a die coater, a curtain coater, various printing methods, and immersion.
• the composition of the present invention can be applied onto a substrate.
• the substrate can be appropriately set depending on the application of the cured product, and examples thereof include soda glass, quartz glass, a semiconductor substrate, metal, paper, and plastic.
• the cured product may be formed on the substrate, and then peeled off from the substrate, or transferred from the substrate to another adherend.
• Comparative Examples 1 to 3 are comparative examples corresponding to Patent Document 1.
• Examples and Comparative Examples The compositions of Examples 1 to 19 and Comparative Examples 1 to 11 were prepared by thoroughly mixing the components according to the formulations shown in Tables 1 to 5 below.
• the symbols in the tables refer to the following components.
• the numerical values of the formulations in the tables are in parts by mass.
• A'-2 Tri(acryloylethyl)isocyanurate
• (Epoxy compound (C)) C'-1 Copolymer of methyl methacrylate and glycidyl methacrylate, weight average molecular weight 8,000, epoxy equivalent 500-600 C2-1: 1,4-butanediol diglycidyl ester
• the obtained adhesive test piece was left for 3 minutes after exposure under conditions of 30° C., 50% RH, and atmospheric pressure, and then cut into a 2.0 cm width to obtain an evaluation sample. Using this evaluation sample, a 90° peel test was performed at a load speed of 300 mm/min, and the evaluation was performed according to the following criteria. S: More than 1.0 N/2 cm or substrate destruction A: More than 0.5 N/2 cm and 1.0 N/2 cm or less B: More than 0.2 N/2 cm and 0.5 N/2 cm or less C: 0.2 N/2 cm or less A higher initial curability value means better curability.
• compositions obtained in the examples and comparative examples were applied to a glass plate with a thickness of 50 ⁇ m, and another glass plate was attached to the glass plate.
• the plate was irradiated with 1000 mJ/cm 2 of active energy rays from a high-pressure Hg lamp, and heated at 150 ° C for 1 hour to obtain a test piece.
• the b* in the L*a*b* color space of the obtained test piece was measured using a UV-Visible Near-Infrared Spectrophotometer V-670 (manufactured by JASCO Corporation) (hereinafter referred to as "b* S ").
• viscosity V 1 The viscosity (hereinafter also referred to as "viscosity V 1 ") of the compositions of the Examples and Comparative Examples immediately after production was measured using a viscometer (a cone-plate type viscometer (TVE-22L manufactured by Toki Sangyo Co., Ltd.) in an atmosphere of 25°C, and evaluated according to the following evaluation criteria.
• B Viscosity V1 is more than 40 mPa ⁇ s and 100 mPa ⁇ s or less
• Viscosity V1 is 100 mPa ⁇ s or more The lower the viscosity, the better the handleability, which is preferable.
• Comparative Examples 1 to 3 which correspond to Patent Document 1, have poor initial curing properties and therefore insufficient adhesion, and there is also room for improvement in terms of high viscosity.
• composition which has excellent adhesive properties and excellent moist heat resistance of the cured product, and which has a low viscosity.

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