WO2012165259A1 - Energy-beam-curable resin composition - Google Patents
Energy-beam-curable resin composition Download PDFInfo
- Publication number
- WO2012165259A1 WO2012165259A1 PCT/JP2012/063192 JP2012063192W WO2012165259A1 WO 2012165259 A1 WO2012165259 A1 WO 2012165259A1 JP 2012063192 W JP2012063192 W JP 2012063192W WO 2012165259 A1 WO2012165259 A1 WO 2012165259A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- resin composition
- curable resin
- component
- energy ray
- mass
- Prior art date
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- 239000011342 resin composition Substances 0.000 title claims abstract description 47
- 125000003700 epoxy group Chemical group 0.000 claims abstract description 14
- 239000003505 polymerization initiator Substances 0.000 claims abstract description 14
- 150000001875 compounds Chemical class 0.000 claims abstract description 11
- 125000002723 alicyclic group Chemical group 0.000 claims abstract description 6
- 125000005702 oxyalkylene group Chemical group 0.000 claims abstract description 6
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 claims abstract description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 4
- 239000000853 adhesive Substances 0.000 claims description 20
- 239000000178 monomer Substances 0.000 claims description 20
- 230000001070 adhesive effect Effects 0.000 claims description 19
- 238000006116 polymerization reaction Methods 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 abstract 1
- 229920000642 polymer Polymers 0.000 abstract 1
- 239000000126 substance Substances 0.000 description 32
- -1 acrylic compound Chemical class 0.000 description 17
- 239000003822 epoxy resin Substances 0.000 description 11
- 239000003999 initiator Substances 0.000 description 11
- 229920000647 polyepoxide Polymers 0.000 description 11
- 239000011521 glass Substances 0.000 description 10
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 9
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- 229920002857 polybutadiene Polymers 0.000 description 8
- 150000003254 radicals Chemical class 0.000 description 8
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 6
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 6
- 238000011156 evaluation Methods 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 239000004593 Epoxy Substances 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 5
- 239000003504 photosensitizing agent Substances 0.000 description 5
- OECTYKWYRCHAKR-UHFFFAOYSA-N 4-vinylcyclohexene dioxide Chemical compound C1OC1C1CC2OC2CC1 OECTYKWYRCHAKR-UHFFFAOYSA-N 0.000 description 4
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- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical compound C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 description 3
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- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 3
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
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- VUIWJRYTWUGOOF-UHFFFAOYSA-N 2-ethenoxyethanol Chemical compound OCCOC=C VUIWJRYTWUGOOF-UHFFFAOYSA-N 0.000 description 2
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- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
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- 230000001771 impaired effect Effects 0.000 description 2
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- 229920003986 novolac Polymers 0.000 description 2
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 description 2
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- 150000003573 thiols Chemical class 0.000 description 2
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 2
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
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- QGKMIGUHVLGJBR-UHFFFAOYSA-M (4z)-1-(3-methylbutyl)-4-[[1-(3-methylbutyl)quinolin-1-ium-4-yl]methylidene]quinoline;iodide Chemical class [I-].C12=CC=CC=C2N(CCC(C)C)C=CC1=CC1=CC=[N+](CCC(C)C)C2=CC=CC=C12 QGKMIGUHVLGJBR-UHFFFAOYSA-M 0.000 description 1
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- SKYXLDSRLNRAPS-UHFFFAOYSA-N 1,2,4-trifluoro-5-methoxybenzene Chemical compound COC1=CC(F)=C(F)C=C1F SKYXLDSRLNRAPS-UHFFFAOYSA-N 0.000 description 1
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- 125000000129 anionic group Chemical group 0.000 description 1
- 150000001454 anthracenes Chemical class 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 229940058905 antimony compound for treatment of leishmaniasis and trypanosomiasis Drugs 0.000 description 1
- 150000001463 antimony compounds Chemical class 0.000 description 1
- 229940054058 antipsychotic thioxanthene derivative Drugs 0.000 description 1
- 150000001495 arsenic compounds Chemical class 0.000 description 1
- 150000001545 azulenes Chemical class 0.000 description 1
- 229960002130 benzoin Drugs 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 150000008366 benzophenones Chemical class 0.000 description 1
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical class C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 229930006711 bornane-2,3-dione Natural products 0.000 description 1
- 150000001639 boron compounds Chemical class 0.000 description 1
- WWNGFHNQODFIEX-UHFFFAOYSA-N buta-1,3-diene;methyl 2-methylprop-2-enoate;styrene Chemical compound C=CC=C.COC(=O)C(C)=C.C=CC1=CC=CC=C1 WWNGFHNQODFIEX-UHFFFAOYSA-N 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 150000001846 chrysenes Chemical class 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 150000001893 coumarin derivatives Chemical class 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 150000004294 cyclic thioethers Chemical class 0.000 description 1
- ZWAJLVLEBYIOTI-UHFFFAOYSA-N cyclohexene oxide Chemical compound C1CCCC2OC21 ZWAJLVLEBYIOTI-UHFFFAOYSA-N 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- VFHVQBAGLAREND-UHFFFAOYSA-N diphenylphosphoryl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 VFHVQBAGLAREND-UHFFFAOYSA-N 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 229920006332 epoxy adhesive Polymers 0.000 description 1
- 238000005530 etching Methods 0.000 description 1
- UYMKPFRHYYNDTL-UHFFFAOYSA-N ethenamine Chemical compound NC=C UYMKPFRHYYNDTL-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 150000002220 fluorenes Chemical class 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- 235000019382 gum benzoic Nutrition 0.000 description 1
- 229940093920 gynecological arsenic compound Drugs 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 125000003387 indolinyl group Chemical class N1(CCC2=CC=CC=C12)* 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 239000011256 inorganic filler Substances 0.000 description 1
- 229910003475 inorganic filler Inorganic materials 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- NINOYJQVULROET-UHFFFAOYSA-N n,n-dimethylethenamine Chemical compound CN(C)C=C NINOYJQVULROET-UHFFFAOYSA-N 0.000 description 1
- NVYYEMGLXURWFJ-UHFFFAOYSA-N n-but-3-enylbutan-1-amine Chemical compound CCCCNCCC=C NVYYEMGLXURWFJ-UHFFFAOYSA-N 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- SRFLQIDBOUXPFK-UHFFFAOYSA-N n-ethenyl-n-phenylaniline Chemical compound C=1C=CC=CC=1N(C=C)C1=CC=CC=C1 SRFLQIDBOUXPFK-UHFFFAOYSA-N 0.000 description 1
- ZQXSMRAEXCEDJD-UHFFFAOYSA-N n-ethenylformamide Chemical compound C=CNC=O ZQXSMRAEXCEDJD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 150000002791 naphthoquinones Chemical class 0.000 description 1
- 150000004893 oxazines Chemical class 0.000 description 1
- 125000003566 oxetanyl group Chemical group 0.000 description 1
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 1
- CXYRUNPLKGGUJF-OZVSTBQFSA-M pamine Chemical compound [Br-].C1([C@@H](CO)C(=O)OC2C[C@@H]3[N+]([C@H](C2)[C@@H]2[C@H]3O2)(C)C)=CC=CC=C1 CXYRUNPLKGGUJF-OZVSTBQFSA-M 0.000 description 1
- 150000002964 pentacenes Chemical class 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- 150000002987 phenanthrenes Chemical class 0.000 description 1
- 239000002530 phenolic antioxidant Substances 0.000 description 1
- 125000001484 phenothiazinyl group Chemical class C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- LYXOWKPVTCPORE-UHFFFAOYSA-N phenyl-(4-phenylphenyl)methanone Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1C(=O)C1=CC=CC=C1 LYXOWKPVTCPORE-UHFFFAOYSA-N 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000012779 reinforcing material Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 150000003303 ruthenium Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 150000003518 tetracenes Chemical class 0.000 description 1
- 150000004897 thiazines Chemical class 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 150000005075 thioxanthenes Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 125000001834 xanthenyl group Chemical class C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 1
- 150000007964 xanthones Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J4/00—Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J4/00—Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16
- C09J4/06—Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09J159/00 - C09J187/00
-
- 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
-
- 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
- C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/10—Esters
- C08F20/26—Esters containing oxygen in addition to the carboxy oxygen
-
- 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
- C08G59/20—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
- C08G59/22—Di-epoxy compounds
- C08G59/223—Di-epoxy compounds together with monoepoxy compounds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/02—Non-macromolecular additives
- C09J11/06—Non-macromolecular additives organic
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J163/00—Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Epoxy Resins (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Polyethers (AREA)
Abstract
Description
(1)(A)下記式〔1〕で表される分子内に(メタ)アクリロイル基と、脂環式エポキシ基を有する化合物 The present invention includes the following aspects (1) to (7).
(1) (A) Compound having (meth) acryloyl group and alicyclic epoxy group in the molecule represented by the following formula [1]
(B)光カチオン重合開始剤
(C)光ラジカル重合開始剤
を含有するエネルギー線硬化型樹脂組成物。
(2)(D)分子内に2つ以上のエポキシ基を有するオリゴマーを含有する(1)に記載のエネルギー線硬化性樹脂組成物。
(3)(D)分子内に2つ以上のエポキシ基を有するオリゴマーの分子量が、350~100,000である(2)に記載のエネルギー線硬化性樹脂組成物。
(4)(E)(A)および(B)以外のカチオン重合性単量体を含有する(1)に記載のエネルギー線硬化性樹脂組成物。
(5)(1)~(4)のいずれかに記載のエネルギー線硬化性樹脂組成物からなる接着剤。
(6)(1)~(4)のいずれかに記載のエネルギー線硬化性樹脂組成物が硬化してなる硬化体。
(7)(1)~(4)のいずれかに記載のエネルギー線硬化性樹脂組成物を用いる接合体。 (Wherein R represents hydrogen or a methyl group, X represents an alkylene chain having 1 to 6 carbon atoms or an oxyalkylene chain having 1 to 6 carbon atoms), (A) component, (D) component and ( E) Energy beam curable resin composition containing 65 parts by mass and 100 parts by mass or less of (B) photocationic polymerization initiator (C) photoradical polymerization initiator in 100 parts by mass of the total amount of polymerization components comprising the component.
(2) The energy ray-curable resin composition according to (1), which contains (D) an oligomer having two or more epoxy groups in the molecule.
(3) The energy ray-curable resin composition according to (2), wherein (D) the molecular weight of the oligomer having two or more epoxy groups in the molecule is 350 to 100,000.
(4) (E) The energy ray-curable resin composition according to (1), which contains a cationically polymerizable monomer other than (A) and (B).
(5) An adhesive comprising the energy beam curable resin composition according to any one of (1) to (4).
(6) A cured product obtained by curing the energy beam curable resin composition according to any one of (1) to (4).
(7) A joined body using the energy ray-curable resin composition according to any one of (1) to (4).
本明細書において、エネルギー線硬化性樹脂組成物とは、エネルギー線を照射することによって硬化させることができる樹脂組成物を意味する。ここで、エネルギー線とは、紫外線、可視光線等に代表されるエネルギー線を意味する。 <Explanation of terms>
In this specification, the energy ray curable resin composition means a resin composition that can be cured by irradiation with energy rays. Here, the energy rays mean energy rays typified by ultraviolet rays and visible rays.
オキシアルキレン鎖としては、-R’-O-が挙げられる。ここで、R’は炭素数1~6のアルキレンをいう。オキシアルキレン鎖が-R’-O-である場合、式〔1〕は下記式〔1’〕で表される。 (In the formula, R represents hydrogen or a methyl group, and X represents an alkyl chain having 1 to 6 carbon atoms or an oxyalkylene chain having 1 to 6 carbon atoms.)
Examples of the oxyalkylene chain include —R′—O—. Here, R ′ refers to alkylene having 1 to 6 carbon atoms. When the oxyalkylene chain is —R′—O—, the formula [1] is represented by the following formula [1 ′].
脂肪族系としては、エポキシ化変性ポリブタジエン、エポキシ化変性ポリイソプレン等のエポキシ化変性ポリオレフィン、ポリエチレングリコール付加体のジグリシジルエーテル、ポリプロピレングリコール付加体のジグリシジルエーテル等のポリアルキレングリコールのジグリシジルエーテル等が挙げられる。脂環系としては、2,2-ビス(ヒドロキシメチル)-1-ブタノールの1,2-エポキシ-4-(2-オキシラニル)シクロヘキサン付加物や、上述の芳香族系エポキシ樹脂の水素添加物が挙げられる。これらの中では、エポキシ化変性ポリブタジエン、エポキシ化変性ポリイソプレン、2,2-ビス(ヒドロキシメチル)-1-ブタノールの1,2-エポキシ-4-(2-オキシラニル)シクロヘキサン付加物からなる1種以上が、耐薬品性に優れる点で、好ましく、エポキシ化変性ポリブタジエンがより好ましい。 Examples of the oligomer having one or more epoxy groups in the molecule of the component (D) used in the present invention include aromatic, aliphatic and alicyclic oligomers. Aromatic resins include bisphenol A type epoxy resin, bisphenol F type epoxy resin, bisphenol S type epoxy resin, biphenyl type epoxy resin, fluorene type epoxy resin, novolac phenol type epoxy resin, cresol novolac type epoxy resin, and modified products thereof. Etc.
Aliphatics include epoxidized modified polyolefins such as epoxidized modified polybutadiene and epoxidized modified polyisoprene, diglycidyl ethers of polyethylene glycol adducts, diglycidyl ethers of polyalkylene glycols such as diglycidyl ethers of polypropylene glycol adducts, etc. Is mentioned. Examples of the alicyclic system include 1,2-epoxy-4- (2-oxiranyl) cyclohexane adduct of 2,2-bis (hydroxymethyl) -1-butanol and hydrogenated products of the above-mentioned aromatic epoxy resins. Can be mentioned. Among these, epoxidized modified polybutadiene, epoxidized modified polyisoprene, and 1,2-epoxy-4- (2-oxiranyl) cyclohexane adduct of 2,2-bis (hydroxymethyl) -1-butanol The above is preferable in terms of excellent chemical resistance, and epoxidized modified polybutadiene is more preferable.
(A)成分として下記を用いた。
(A-1)3,4-エポキシシクロヘキシルメチルメタクリレート(ダイセル化学工業社「サイクロマーM-100」)
(A-2)3,4-エポキシシクロヘキシルメチルアクリレート(ダイセル化学工業社「サイクロマーA-200」) In the examples, the following compounds were used.
The following was used as the component (A).
(A-1) 3,4-epoxycyclohexylmethyl methacrylate (Daicel Chemical Industries, Ltd. “Cyclomer M-100”)
(A-2) 3,4-epoxycyclohexylmethyl acrylate (Daicel Chemical Industries, Ltd. “Cyclomer A-200”)
(B-1)芳香族スルホニウムSbF6塩(アデカ社製「アデカオプトマーSP-170」)
(B-2)芳香族スルホニウムPF6塩(アデカ社製「アデカオプトマーSP-150」) The following was used as the photocationic polymerization initiator of component (B).
(B-1) Aromatic sulfonium SbF 6 salt (“Adekaoptomer SP-170” manufactured by Adeka)
(B-2) Aromatic sulfonium PF 6 salt (“Adekaoptomer SP-150” manufactured by Adeka)
(C-1)2-ヒドロキシ-2-メチル-1-フェニル-プロパン-1-オン(チバジャパン社製「ダロキュア1173」)
(C-2)1-ヒドロキシシクロヘキシルフェニルケトン(チバジャパン社製「イルガキュアー184」)
(C-3)2-ヒドロキシ-1-{4-[4-(2-ヒドロキシ-2-メチル-プロピオニル)-ベンジル]フェニル}-2-メチル-プロパン-1-オン(チバジャパン社製「イルガキュアー127」) The following was used as the radical photopolymerization initiator of component (C).
(C-1) 2-Hydroxy-2-methyl-1-phenyl-propan-1-one (“Darocur 1173” manufactured by Ciba Japan)
(C-2) 1-hydroxycyclohexyl phenyl ketone (“Irgacure 184” manufactured by Ciba Japan)
(C-3) 2-hydroxy-1- {4- [4- (2-hydroxy-2-methyl-propionyl) -benzyl] phenyl} -2-methyl-propan-1-one (“Irga” manufactured by Ciba Japan) Cure 127 ")
(D-1)ビスフェノールA型エポキシ樹脂(アデカ社製「アデカオプトマーKRM-2410」 分子量:400)
(D-2)ビスフェノールF型エポキシ樹脂(アデカ社製「アデカオプトマーKRM-2490」 分子量:380)
(D-3)水添ビスフェノールA型エポキシ樹脂(三菱化学社製「YX-8000」 分子量:410)
(D-4)2,2-ビス(ヒドロキシメチル)-1-ブタノールの1,2-エポキシ-4-(2-オキシラニル)シクロヘキサン付加物(ダイセル化学工業社製「EHPE-3150」 分子量:2,400)
(D-5)エポキシ化ポリブタジエン(1)(アデカ社製「BF-1000」 分子量:4,300 ミクロ構造:1,2-ポリブタジエン)
(D-6)エポキシ化ポリブタジエン(2)(日本曹達社製「JP-200」 分子量:6,400 ミクロ構造:1,2-ポリブタジエン)
(D-7)エポキシ化ポリブタジエン(3)(ダイセル化学工業社製「BP-3600」 分子量:19,300 ミクロ構造:1,2-体/1,4-cis体/1,4-trans体=40mol%/40mol%/20mol%の共重合体)
(D-8)エポキシ化ポリブタジエンとスチレンの共重合体(ダイセル化学工業社製「エポフレンドシリーズ」 分子量:20,000を超える) The following was used as an oligomer having an epoxy group as component (D).
(D-1) Bisphenol A type epoxy resin (“ADEKA OPTOMER KRM-2410”, molecular weight: 400, manufactured by ADEKA)
(D-2) Bisphenol F-type epoxy resin (“ADEKA OPTOMER KRM-2490” manufactured by ADEKA Corporation, molecular weight: 380)
(D-3) Hydrogenated bisphenol A type epoxy resin (Mitsubishi Chemical Corporation “YX-8000” molecular weight: 410)
(D-4) 1,2-epoxy-4- (2-oxiranyl) cyclohexane adduct of 2,2-bis (hydroxymethyl) -1-butanol (“EHPE-3150” manufactured by Daicel Chemical Industries, Ltd., molecular weight: 2, 400)
(D-5) Epoxidized polybutadiene (1) (“BF-1000” manufactured by Adeka Corporation, molecular weight: 4,300, microstructure: 1,2-polybutadiene)
(D-6) Epoxidized polybutadiene (2) (“JP-200” manufactured by Nippon Soda Co., Ltd. Molecular weight: 6,400 Microstructure: 1,2-polybutadiene)
(D-7) Epoxidized polybutadiene (3) (“BP-3600” manufactured by Daicel Chemical Industries, Ltd.) Molecular weight: 19,300 Microstructure: 1,2-isomer / 1,4-cis isomer / 1,4-trans isomer = 40 mol% / 40 mol% / 20 mol% copolymer)
(D-8) Copolymer of epoxidized polybutadiene and styrene ("Epofriend series" manufactured by Daicel Chemical Industries, Ltd., molecular weight: over 20,000)
(E-1)3,4-エポキシシクロヘキセニルメチル-3’,4’-エポキシシクロヘキセンカルボキシレート(ダイセル化学社製「セロキサイド2021P」)
(E-2)ジ(1-エチル-3-オキセタニル)メチルエーテル(東亜合成社「OXT221」)
(E-3)4-ヒドロキシブチルメタクリレートグリシジルエーテル(日本化成社「ヒッタイトG」) The following was used as a cationically polymerizable monomer other than the components (A) and (B) as the component (E).
(E-1) 3,4-epoxycyclohexenylmethyl-3 ′, 4′-epoxycyclohexene carboxylate (“Celoxide 2021P” manufactured by Daicel Chemical Industries)
(E-2) Di (1-ethyl-3-oxetanyl) methyl ether (Toa Gosei Co., Ltd. “OXT221”)
(E-3) 4-hydroxybutyl methacrylate glycidyl ether (Nippon Kasei Co., Ltd. “Hitite G”)
表1~表4に示す種類の原材料を、表1~表4に示す組成割合(単位は質量部)で混合し、樹脂組成物を調製し、後述の評価を実施した。各種評価結果を表1~表4に示す。特記しない限り、23℃、湿度50%の環境下で実施した。 (Examples 1 to 16, Comparative Examples 1 to 6)
The raw materials of the types shown in Tables 1 to 4 were mixed at the composition ratios (units are parts by mass) shown in Tables 1 to 4 to prepare resin compositions, which were evaluated later. Various evaluation results are shown in Tables 1 to 4. Unless otherwise specified, the test was carried out in an environment of 23 ° C. and 50% humidity.
レオメーター(アートンパール社製「MCR-301」)ではUV照射下の剛性率を測定することができる。測定は、調製した樹脂組成物を直径8mmの円形のプレートで両面から挟み、該樹脂組成物にUV(365nmの照度:150mW/cm2)を照射しながら25℃(±0.5℃)、周波数10Hzで行った。UV照射開始後200秒までに、貯蔵剛性率G’が1.00×104以上に増加したものを「合格(Good)」とし、硬化性が良好と判断した。 (Photocurability evaluation)
A rheometer (“MCR-301” manufactured by Arton Pearl) can measure the rigidity under UV irradiation. The measurement is performed by sandwiching the prepared resin composition from both sides with a circular plate having a diameter of 8 mm, and irradiating the resin composition with UV (365 nm illuminance: 150 mW / cm 2 ) at 25 ° C. (± 0.5 ° C.), The frequency was 10 Hz. A sample in which the storage rigidity G ′ increased to 1.00 × 10 4 or more by 200 seconds after the start of UV irradiation was regarded as “Good”, and the curability was judged to be good.
ガラス試験片(商品名「耐熱パイレックス(登録商標)ガラス」、25mm×25mm×2.0mm)上に、直径8mm、厚さ80μmになるように樹脂組成物を塗布した後、2枚目のガラス試験片を張り合わせ、UV照射器(365nmの照度:150mW/cm2、ウシオ電機社製「SP-7(水銀キセノンランプ搭載UV硬化装置)」)によりUV光を照射し、2枚のガラス試験片が動かなくなる時間を測定し、固着時間とした。尚、測定時間は最大で120秒までとした。 [Evaluation of fixing time]
On the glass test piece (trade name “Heat-resistant Pyrex (registered trademark) glass”, 25 mm × 25 mm × 2.0 mm), a resin composition was applied so as to have a diameter of 8 mm and a thickness of 80 μm. Two glass test pieces were irradiated by irradiating UV light with a UV irradiator (illuminance of 365 nm: 150 mW / cm 2 , “SP-7 (UV curing device equipped with mercury xenon lamp)” manufactured by USHIO INC.)). The time during which the film stopped moving was measured and used as the fixing time. The measurement time was up to 120 seconds.
引張剪断接着強さ:JIS K 6850に従い測定した。具体的には被着材とした耐熱ガラス(商品名「耐熱パイレックス(登録商標)ガラス」、25mm×25mm×2.0mm)を用いて、接着部位を直径8mmの円形として、作製した該樹脂組成物にて、2枚の耐熱ガラスを張り合わせ、UV照射器を使用し、積算光量3,000mJ/cm2(365nmの照度:150mW/cm2、ウシオ電機社製「SP-7(水銀キセノンランプ搭載UV硬化装置)」)の条件にて硬化させ、試験片を作製した。作製した試験片は、23℃、湿度50%の環境で、引張試験機を使用して、引張剪断接着強さを測定した。 [Evaluation of tensile shear bond strength]
Tensile shear bond strength: measured in accordance with JIS K 6850. Specifically, the resin composition produced by using a heat-resistant glass (trade name “heat-resistant Pyrex (registered trademark) glass”, 25 mm × 25 mm × 2.0 mm) as an adherend, and forming a bonded portion with a circle having a diameter of 8 mm. Two pieces of heat-resistant glass are laminated together, using a UV irradiator, integrated light intensity of 3,000 mJ / cm 2 (365 nm illuminance: 150 mW / cm 2 , “SP-7 (mercury xenon lamp installed) by USHIO ELECTRIC CO., LTD. A test piece was prepared by curing under the conditions of a UV curing apparatus))). The produced test piece was measured for tensile shear bond strength using a tensile tester in an environment of 23 ° C. and humidity of 50%.
ガラス試験片(商品名「耐熱パイレックス(登録商標)ガラス」、25mm×25mm×2.0mm)上に、直径20mm、厚さ80μmになるように樹脂組成物を塗布した後、2枚目のガラス試験片を張り合わせ、UV照射器(365nmの照度:150mW/cm2、ウシオ電機社製「SP-7(水銀キセノンランプ搭載UV硬化装置)」)によりUV光を照射し、試験片を作成した。作成した試験片の波長405nmと500nmの分光透過率を紫外-可視分光スペクトルメーター(島津製作所社製「UV-2550」)を用いて測定した。尚、リファレンスには純水を用いた。 [Evaluation of spectral transmittance]
On the glass test piece (trade name “Heat-resistant Pyrex (registered trademark) glass”, 25 mm × 25 mm × 2.0 mm), a resin composition is applied so as to have a diameter of 20 mm and a thickness of 80 μm. The test pieces were bonded together and irradiated with UV light using a UV irradiator (illuminance at 365 nm: 150 mW / cm 2 , “SP-7 (UV curing device equipped with a mercury xenon lamp)” manufactured by USHIO INC.) To prepare a test piece. Spectral transmittances at wavelengths of 405 nm and 500 nm of the prepared test pieces were measured using an ultraviolet-visible spectral spectrometer (“UV-2550” manufactured by Shimadzu Corporation). Note that pure water was used as a reference.
UV照射器を使用し、4,000mJ/cm2(365nmの照度:150mW/cm2、フュージョン社製「ベルトコンベア式無電極放電ランプ(D-バルブ:メタルハライドランプ)」)の条件にて25mm×25mm×2.0mmの形状の硬化物を作製し、作製した硬化物をアセトン中に23℃の環境下で4時間浸漬し、浸漬前後での質量の変化率(%)を測定した。質量の変化率が低いもの程、耐薬品性に優れるものとして評価した。 [Evaluation of chemical resistance]
Using a UV irradiator, 4,000 mJ / cm 2 (365 nm illuminance: 150 mW / cm 2 , “Belt conveyor type electrodeless discharge lamp (D-bulb: metal halide lamp)” manufactured by Fusion) 25 mm × A cured product having a shape of 25 mm × 2.0 mm was produced, and the produced cured product was immersed in acetone at 23 ° C. for 4 hours, and a mass change rate (%) before and after immersion was measured. The lower the rate of change in mass, the better the chemical resistance.
さらに本発明は405nmで90%以上、550nmで98%以上の透過率を示すことから可視光域で優れた透明性を有することが判る。 From the results shown in Tables 1 to 4, the following can be understood. The present invention has rapid curability. Furthermore, the present invention has high adhesion and chemical resistance. When the component (A) is 65 parts by mass or less, the effect of the present invention cannot be obtained (contrast of Example 11 and Comparative Example 6). When the component (D) is used, the adhesive strength and the like are improved (contrast of Example 12 and Examples 1 to 3). When the component (D) is used, the adhesive strength and the like are improved as compared with the case where the component (E) is used (contrast of Examples 4 to 11 and Examples 14 to 15).
Furthermore, since the present invention exhibits a transmittance of 90% or more at 405 nm and 98% or more at 550 nm, it can be seen that the present invention has excellent transparency in the visible light region.
Claims (7)
- (A)下記式〔1〕で表される分子内に(メタ)アクリロイル基と、脂環式エポキシ基を有する化合物
(B)光カチオン重合開始剤
(C)光ラジカル重合開始剤
を含有するエネルギー線硬化型樹脂組成物。 (A) Compound having (meth) acryloyl group and alicyclic epoxy group in the molecule represented by the following formula [1]
- (D)分子内に2つ以上のエポキシ基を有するオリゴマーを含有する請求項1に記載のエネルギー線硬化性樹脂組成物。 (D) The energy ray-curable resin composition according to claim 1, comprising an oligomer having two or more epoxy groups in the molecule.
- (D)分子内に2つ以上のエポキシ基を有するオリゴマーの分子量が、350~100,000である請求項2に記載のエネルギー線硬化性樹脂組成物。 The energy ray-curable resin composition according to claim 2, wherein the molecular weight of the oligomer (D) having two or more epoxy groups in the molecule is 350 to 100,000.
- (E)(A)および(B)以外のカチオン重合性単量体を含有する請求項1に記載のエネルギー線硬化性樹脂組成物。 (E) The energy ray-curable resin composition according to claim 1, comprising a cationically polymerizable monomer other than (A) and (B).
- 請求項1~4のいずれか1項に記載のエネルギー線硬化性樹脂組成物からなる接着剤。 An adhesive comprising the energy ray-curable resin composition according to any one of claims 1 to 4.
- 請求項1~4のいずれか1項に記載のエネルギー線硬化性樹脂組成物が硬化してなる硬化体。 A cured product obtained by curing the energy ray-curable resin composition according to any one of claims 1 to 4.
- 請求項1~4のいずれか1項に記載のエネルギー線硬化性樹脂組成物を用いる接合体。 A joined body using the energy ray-curable resin composition according to any one of claims 1 to 4.
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