JP6682553B2 - エポキシ樹脂組成物 - Google Patents
エポキシ樹脂組成物 Download PDFInfo
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- JP6682553B2 JP6682553B2 JP2017551000A JP2017551000A JP6682553B2 JP 6682553 B2 JP6682553 B2 JP 6682553B2 JP 2017551000 A JP2017551000 A JP 2017551000A JP 2017551000 A JP2017551000 A JP 2017551000A JP 6682553 B2 JP6682553 B2 JP 6682553B2
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- Prior art keywords
- adhesive composition
- epoxy resin
- epoxy
- core
- curing
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims description 96
- 229920000647 polyepoxide Polymers 0.000 title claims description 54
- 239000003822 epoxy resin Substances 0.000 title claims description 47
- 239000000853 adhesive Substances 0.000 claims description 79
- 230000001070 adhesive effect Effects 0.000 claims description 79
- 238000000034 method Methods 0.000 claims description 24
- 239000002245 particle Substances 0.000 claims description 23
- 229920001971 elastomer Polymers 0.000 claims description 20
- 229920000570 polyether Polymers 0.000 claims description 19
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 15
- 239000004593 Epoxy Substances 0.000 claims description 14
- 230000009477 glass transition Effects 0.000 claims description 14
- 229920000459 Nitrile rubber Polymers 0.000 claims description 12
- NTXGQCSETZTARF-UHFFFAOYSA-N buta-1,3-diene;prop-2-enenitrile Chemical compound C=CC=C.C=CC#N NTXGQCSETZTARF-UHFFFAOYSA-N 0.000 claims description 12
- 239000003795 chemical substances by application Substances 0.000 claims description 12
- 239000011541 reaction mixture Substances 0.000 claims description 11
- 125000003700 epoxy group Chemical group 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- 238000010438 heat treatment Methods 0.000 claims description 5
- 229920001451 polypropylene glycol Polymers 0.000 claims description 5
- 150000004985 diamines Chemical class 0.000 claims description 4
- 238000005304 joining Methods 0.000 claims description 3
- 239000011257 shell material Substances 0.000 description 22
- 239000007771 core particle Substances 0.000 description 14
- 239000010420 shell particle Substances 0.000 description 14
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- -1 steel or aluminum Chemical class 0.000 description 11
- 229920000642 polymer Polymers 0.000 description 9
- 125000003277 amino group Chemical group 0.000 description 8
- 238000009472 formulation Methods 0.000 description 8
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- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 6
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- 229910052782 aluminium Inorganic materials 0.000 description 6
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- 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
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 6
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- 239000010959 steel Substances 0.000 description 6
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 5
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 5
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- 239000002131 composite material Substances 0.000 description 5
- 239000000945 filler Substances 0.000 description 5
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 4
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- 238000006243 chemical reaction Methods 0.000 description 4
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 4
- 150000002170 ethers Chemical class 0.000 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- 150000008442 polyphenolic compounds Chemical class 0.000 description 4
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- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 239000004609 Impact Modifier Substances 0.000 description 3
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 3
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- 125000001931 aliphatic group Chemical group 0.000 description 3
- 239000004917 carbon fiber Substances 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 239000003365 glass fiber Substances 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 229920002635 polyurethane Polymers 0.000 description 3
- 239000004814 polyurethane Substances 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- VZXTWGWHSMCWGA-UHFFFAOYSA-N 1,3,5-triazine-2,4-diamine Chemical class NC1=NC=NC(N)=N1 VZXTWGWHSMCWGA-UHFFFAOYSA-N 0.000 description 2
- XMTQQYYKAHVGBJ-UHFFFAOYSA-N 3-(3,4-DICHLOROPHENYL)-1,1-DIMETHYLUREA Chemical compound CN(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 XMTQQYYKAHVGBJ-UHFFFAOYSA-N 0.000 description 2
- GZVHEAJQGPRDLQ-UHFFFAOYSA-N 6-phenyl-1,3,5-triazine-2,4-diamine Chemical class NC1=NC(N)=NC(C=2C=CC=CC=2)=N1 GZVHEAJQGPRDLQ-UHFFFAOYSA-N 0.000 description 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- 239000004640 Melamine resin Chemical class 0.000 description 2
- 229920000877 Melamine resin Chemical class 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 2
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 2
- 235000013877 carbamide Nutrition 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 150000002357 guanidines Chemical class 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 239000004850 liquid epoxy resins (LERs) Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- BMLIZLVNXIYGCK-UHFFFAOYSA-N monuron Chemical compound CN(C)C(=O)NC1=CC=C(Cl)C=C1 BMLIZLVNXIYGCK-UHFFFAOYSA-N 0.000 description 2
- 150000002924 oxiranes Chemical class 0.000 description 2
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 2
- 229920000515 polycarbonate Polymers 0.000 description 2
- 239000004417 polycarbonate Substances 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 239000003380 propellant Substances 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 235000012239 silicon dioxide Nutrition 0.000 description 2
- 229920002379 silicone rubber Polymers 0.000 description 2
- 239000004945 silicone rubber Substances 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 150000005846 sugar alcohols Polymers 0.000 description 2
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- 150000003672 ureas Chemical class 0.000 description 2
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- 239000002023 wood Substances 0.000 description 2
- NQOFYFRKWDXGJP-UHFFFAOYSA-N 1,1,2-trimethylguanidine Chemical compound CN=C(N)N(C)C NQOFYFRKWDXGJP-UHFFFAOYSA-N 0.000 description 1
- KYVBNYUBXIEUFW-UHFFFAOYSA-N 1,1,3,3-tetramethylguanidine Chemical compound CN(C)C(=N)N(C)C KYVBNYUBXIEUFW-UHFFFAOYSA-N 0.000 description 1
- LINDOXZENKYESA-UHFFFAOYSA-N 1,2-dimethylguanidine Chemical compound CNC(N)=NC LINDOXZENKYESA-UHFFFAOYSA-N 0.000 description 1
- MCMFEZDRQOJKMN-UHFFFAOYSA-N 1-butylimidazole Chemical compound CCCCN1C=CN=C1 MCMFEZDRQOJKMN-UHFFFAOYSA-N 0.000 description 1
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- NBNGHXWJFSMASY-UHFFFAOYSA-N 2,3,4-tris(dimethylamino)phenol Chemical compound CN(C)C1=CC=C(O)C(N(C)C)=C1N(C)C NBNGHXWJFSMASY-UHFFFAOYSA-N 0.000 description 1
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 1
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 1
- QFRHTANKIYQYLO-UHFFFAOYSA-N 2-ethyl-2-methylimidazole Chemical compound CCC1(C)N=CC=N1 QFRHTANKIYQYLO-UHFFFAOYSA-N 0.000 description 1
- CFVWNXQPGQOHRJ-UHFFFAOYSA-N 2-methylpropyl prop-2-enoate Chemical compound CC(C)COC(=O)C=C CFVWNXQPGQOHRJ-UHFFFAOYSA-N 0.000 description 1
- RXNYJUSEXLAVNQ-UHFFFAOYSA-N 4,4'-Dihydroxybenzophenone Chemical compound C1=CC(O)=CC=C1C(=O)C1=CC=C(O)C=C1 RXNYJUSEXLAVNQ-UHFFFAOYSA-N 0.000 description 1
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 1
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- 125000000623 heterocyclic group Chemical group 0.000 description 1
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- FBCQUCJYYPMKRO-UHFFFAOYSA-N prop-2-enyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC=C FBCQUCJYYPMKRO-UHFFFAOYSA-N 0.000 description 1
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- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- SJMYWORNLPSJQO-UHFFFAOYSA-N tert-butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C)(C)C SJMYWORNLPSJQO-UHFFFAOYSA-N 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004634 thermosetting polymer Substances 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 239000004639 urea-formaldehyde foam Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000010456 wollastonite Substances 0.000 description 1
- 229910052882 wollastonite Inorganic materials 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
- C09J163/00—Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B27/00—Layered products comprising a layer of synthetic resin
- B32B27/38—Layered products comprising a layer of synthetic resin comprising epoxy resins
-
- 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
- C08G59/182—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 using pre-adducts of epoxy compounds with curing agents
- C08G59/184—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 using pre-adducts of epoxy compounds with curing agents with amines
-
- 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
- C08G59/182—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 using pre-adducts of epoxy compounds with curing agents
- C08G59/186—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 using pre-adducts of epoxy compounds with curing agents with acids
-
- 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
- C08G59/40—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 curing agents used
- C08G59/42—Polycarboxylic acids; Anhydrides, halides or low molecular weight esters thereof
- C08G59/4246—Polycarboxylic acids; Anhydrides, halides or low molecular weight esters thereof polymers with carboxylic terminal groups
- C08G59/4261—Macromolecular compounds obtained by reactions involving only unsaturated carbon-to-carbon bindings
-
- 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
- C08G59/40—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 curing agents used
- C08G59/50—Amines
- C08G59/504—Amines containing an atom other than nitrogen belonging to the amine group, carbon and hydrogen
-
- 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
- C08G59/40—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 curing agents used
- C08G59/50—Amines
- C08G59/56—Amines together with other curing agents
- C08G59/58—Amines together with other curing agents with polycarboxylic acids or with anhydrides, halides, or low-molecular-weight esters thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L21/00—Compositions of unspecified rubbers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L47/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds; Compositions of derivatives of such polymers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
-
- 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
- C09J11/08—Macromolecular additives
-
- 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
- C09J5/00—Adhesive processes in general; Adhesive processes not provided for elsewhere, e.g. relating to primers
- C09J5/06—Adhesive processes in general; Adhesive processes not provided for elsewhere, e.g. relating to primers involving heating of the applied adhesive
-
- 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
- C08G2650/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G2650/28—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule characterised by the polymer type
- C08G2650/50—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule characterised by the polymer type containing nitrogen, e.g. polyetheramines or Jeffamines(r)
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2207/00—Properties characterising the ingredient of the composition
- C08L2207/53—Core-shell polymer
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- Polymers & Plastics (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Epoxy Resins (AREA)
Description
(a)少なくとも1つのエポキシ樹脂;
(b)少なくとも1つのポリエーテルジアミンまたはポリエーテルトリアミン;
(c)少なくとも1つのカルボキシル末端ブタジエン−アクリロニトリルコポリマー(CTBN);および
(d)コア/シェル構造を有するゴム粒子
を含有する反応混合物を反応させることにより得ることができるプレポリマーを含んでなる接着剤組成物に関する。
少なくとも2つの部材を結合させるための方法であって、
(a)本明細書に記載の接着剤組成物を、結合させる前記部材の一方または両方に適用すること;
(b)前記部材を、接着剤組成物が前記2つの部材の間に位置するように接触させること;
(c)前記接着剤組成物を硬化させるのに好適な条件に曝すことにより前記接着剤組成物を部分的または完全に硬化させること
を含んでなる方法およびこのようにして得ることができる部材に関する。
(a)少なくとも1つのエポキシ樹脂;
(b)少なくとも1つのポリエーテルジアミンまたはポリエーテルトリアミン;
(c)少なくとも1つのカルボキシル末端ブタジエン−アクリロニトリルコポリマー(CTBN);および
(d)コア/シェル構造を有するゴム粒子
を反応させることにより得ることができるプレポリマーを含有する。
1.式:
の直鎖アミン末端ポリオキシエチレンエーテル
2.式:
3.式:
ここで、Aは、
〔1〕(a)少なくとも1つのエポキシ樹脂;
(b)少なくとも1つのポリエーテルジアミンまたはポリエーテルトリアミン、特に、ポリエーテルトリアミン;
(c)少なくとも1つのカルボキシル末端ブタジエン−アクリロニトリルコポリマー(CTBN);および
(d)コア/シェル構造を有するゴム粒子
を含有する反応混合物を反応させることにより得ることができるプレポリマーを含んでなる接着剤組成物。
〔2〕(a)前記少なくとも1つのエポキシ樹脂がポリエポキシド、特に、ポリグリシジルエーテルであり;および/または
(b)前記少なくとも1つのポリエーテルジアミンまたはポリエーテルトリアミンがアミノ末端ポリプロピレンオキシドである
ことを特徴とする、〔1〕に記載の接着剤組成物。
〔3〕前記少なくとも1つのカルボキシル末端ブタジエン−アクリロニトリルコポリマー(CTBN)がCTBNエポキシ樹脂付加物として使用されることを特徴とする、〔1〕または〔2〕に記載の接着剤組成物。
〔4〕プレポリマー用の反応混合物において、エポキシ樹脂はエポキシ基がエポキシ反応性基の合計に対してモル過剰量で存在するような量で使用されることを特徴とする、〔1〕〜〔3〕のいずれか一項に記載の接着剤組成物。
〔5〕潜硬化剤をさらに含有することを特徴とする、〔1〕〜〔4〕のいずれか一項に記載の接着剤組成物。
〔6〕硬化接着剤組成物を生産するための方法であって、
(a)〔1〕〜〔5〕のいずれか一項に記載の接着剤組成物を準備すること;および
(b)前記接着剤組成物を硬化させるのに適した条件に曝すことにより、特に、加熱することにより、前記接着剤組成物を部分的または完全に硬化させること
を含んでなる、方法。
〔7〕〔6〕に記載の方法により得ることができる硬化接着剤組成物。
〔8〕(a)<800、特に、<600MPaの弾性係数を有し;および/または
(b)>100℃のガラス転移温度T g を有する
ことを特徴とする、〔7〕に記載の硬化接着剤組成物。
〔9〕少なくとも2つの部材を結合させるための方法であって、
(d)〔1〕〜〔5〕のいずれか一項に記載の接着剤組成物を、結合させる前記部材の一方または両方に適用すること;
(e)前記部材を、接着剤組成物が前記の2つの部材の間に位置するように接触させること;および
(f)前記接着剤組成物を硬化させるのに適した条件に曝すことにより前記接着剤組成物を部分的または完全に硬化させること
を含んでなる、方法。
〔10〕〔9〕に記載の方法により得ることができる部材。
Claims (8)
- (a)少なくとも1つのエポキシ樹脂;
(b)少なくとも1つのポリエーテルジアミンまたはポリエーテルトリアミン;
(c)少なくとも1つのカルボキシル末端ブタジエン−アクリロニトリルコポリマー(CTBN);および
(d)コア/シェル構造を有するゴム粒子
を含有する反応混合物を反応させることにより得ることができるプレポリマー化混合物を含んでなり、
該少なくとも1つのカルボキシル末端ブタジエン−アクリロニトリルコポリマー(CTBN)はCTBNエポキシ樹脂付加物であり、該反応混合物においてエポキシ樹脂はエポキシ基がエポキシ反応性基の合計に対してモル過剰量で存在するような量である、接着剤組成物。 - (a)前記少なくとも1つのエポキシ樹脂がポリエポキシド、特に、ポリグリシジルエーテルであり;および/または
(b)前記少なくとも1つのポリエーテルジアミンまたはポリエーテルトリアミンがアミノ末端ポリプロピレンオキシドである
ことを特徴とする、請求項1に記載の接着剤組成物。 - 潜硬化剤をさらに含有することを特徴とする、請求項1〜2のいずれか一項に記載の接着剤組成物。
- 硬化接着剤組成物を生産するための方法であって、
(a)請求項1〜3のいずれか一項に記載の接着剤組成物を準備すること;および
(b)前記接着剤組成物を硬化させるのに適した条件に曝すことにより、特に、加熱することにより、前記接着剤組成物を部分的または完全に硬化させること
を含んでなる、方法。 - 請求項4に記載の方法により得ることができる硬化接着剤組成物。
- (a)<800、特に、<600MPaの弾性係数を有し;および/または
(b)>100℃のガラス転移温度Tgを有する
ことを特徴とする、請求項5に記載の硬化接着剤組成物。 - 少なくとも2つの部材を結合させるための方法であって、
(d)請求項1〜3のいずれか一項に記載の接着剤組成物を、結合させる前記部材の一方または両方に適用すること;
(e)前記部材を、接着剤組成物が前記の2つの部材の間に位置するように接触させること;および
(f)前記接着剤組成物を硬化させるのに適した条件に曝すことにより前記接着剤組成物を部分的または完全に硬化させること
を含んでなる、方法。 - 請求項7に記載の方法により得ることができる部材。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE102014226826.5A DE102014226826A1 (de) | 2014-12-22 | 2014-12-22 | Epoxidharz-Zusammensetzung |
DE102014226826.5 | 2014-12-22 | ||
PCT/EP2015/080329 WO2016102329A1 (de) | 2014-12-22 | 2015-12-17 | Epoxidharz-zusammensetzung |
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JP2018506635A JP2018506635A (ja) | 2018-03-08 |
JP6682553B2 true JP6682553B2 (ja) | 2020-04-15 |
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JP2017551000A Active JP6682553B2 (ja) | 2014-12-22 | 2015-12-17 | エポキシ樹脂組成物 |
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US (1) | US10329465B2 (ja) |
EP (1) | EP3237486B1 (ja) |
JP (1) | JP6682553B2 (ja) |
KR (2) | KR20230003611A (ja) |
CN (1) | CN107109176B (ja) |
BR (1) | BR112017013230A2 (ja) |
CA (1) | CA2971507A1 (ja) |
DE (1) | DE102014226826A1 (ja) |
ES (1) | ES2715748T3 (ja) |
HU (1) | HUE043170T2 (ja) |
MX (1) | MX2017008266A (ja) |
PT (1) | PT3237486T (ja) |
TR (1) | TR201906560T4 (ja) |
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JP2020500234A (ja) * | 2016-10-24 | 2020-01-09 | ダウ グローバル テクノロジーズ エルエルシー | 開ビード湿度曝露に耐性のエポキシ接着剤 |
CN108727562B (zh) * | 2017-04-24 | 2020-11-13 | 中国石油化工股份有限公司 | 环氧树脂固化剂、环氧树脂固化方法及得到的环氧树脂固化产品 |
JP7109164B2 (ja) * | 2017-08-24 | 2022-07-29 | サンスター技研株式会社 | 一液型熱硬化性接着剤組成物及び該接着剤組成物が塗布されてなる車両の車体構造 |
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US10677759B2 (en) | 2017-10-26 | 2020-06-09 | The Boeing Company | Adhesive additive with enhanced stiffness change and non-destructive inspection method |
KR102394814B1 (ko) | 2017-12-29 | 2022-05-04 | 현대자동차주식회사 | 상온 경화 이액형 실러 |
CN117925118A (zh) * | 2018-04-18 | 2024-04-26 | 鲁东大学 | 一种用于碳纤维粘接单组份结构胶及其制备方法和应用 |
EP3569405A1 (de) * | 2018-05-18 | 2019-11-20 | voestalpine Stahl GmbH | Elektroband oder -blech, verfahren zur herstellung solch eines elektrobands oder -blechs sowie blechpaket daraus |
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WO2020092360A1 (en) * | 2018-10-29 | 2020-05-07 | Zephyros, Inc. | Improved structural bonding adhesive |
US11166363B2 (en) | 2019-01-11 | 2021-11-02 | Tactotek Oy | Electrical node, method for manufacturing electrical node and multilayer structure comprising electrical node |
CN114127151A (zh) | 2019-04-03 | 2022-03-01 | 汉高股份有限及两合公司 | 基于改性环氧树脂的双组分(2k)组合物 |
WO2022107881A1 (ja) | 2020-11-20 | 2022-05-27 | 東洋インキScホールディングス株式会社 | 無溶剤型反応性接着剤、その硬化物及び積層体 |
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WO2023201614A1 (en) * | 2022-04-21 | 2023-10-26 | Henkel Ag & Co. Kgaa | Curable epoxy compositions, structural adhesive therefrom, and methods of using same |
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-
2014
- 2014-12-22 DE DE102014226826.5A patent/DE102014226826A1/de not_active Withdrawn
-
2015
- 2015-12-17 CA CA2971507A patent/CA2971507A1/en not_active Abandoned
- 2015-12-17 PT PT15816746T patent/PT3237486T/pt unknown
- 2015-12-17 MX MX2017008266A patent/MX2017008266A/es active IP Right Grant
- 2015-12-17 WO PCT/EP2015/080329 patent/WO2016102329A1/de active Application Filing
- 2015-12-17 KR KR1020227043747A patent/KR20230003611A/ko not_active Application Discontinuation
- 2015-12-17 KR KR1020177019509A patent/KR20170097694A/ko not_active Application Discontinuation
- 2015-12-17 HU HUE15816746A patent/HUE043170T2/hu unknown
- 2015-12-17 JP JP2017551000A patent/JP6682553B2/ja active Active
- 2015-12-17 TR TR2019/06560T patent/TR201906560T4/tr unknown
- 2015-12-17 BR BR112017013230-3A patent/BR112017013230A2/pt not_active Application Discontinuation
- 2015-12-17 ES ES15816746T patent/ES2715748T3/es active Active
- 2015-12-17 EP EP15816746.0A patent/EP3237486B1/de active Active
- 2015-12-17 CN CN201580069999.8A patent/CN107109176B/zh active Active
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2017
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Also Published As
Publication number | Publication date |
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WO2016102329A1 (de) | 2016-06-30 |
PT3237486T (pt) | 2019-03-04 |
DE102014226826A1 (de) | 2016-06-23 |
KR20170097694A (ko) | 2017-08-28 |
ZA201704978B (en) | 2019-07-31 |
EP3237486B1 (de) | 2019-02-06 |
JP2018506635A (ja) | 2018-03-08 |
EP3237486A1 (de) | 2017-11-01 |
HUE043170T2 (hu) | 2019-08-28 |
KR20230003611A (ko) | 2023-01-06 |
US10329465B2 (en) | 2019-06-25 |
CA2971507A1 (en) | 2016-06-30 |
US20170321094A1 (en) | 2017-11-09 |
CN107109176B (zh) | 2021-01-26 |
TR201906560T4 (tr) | 2019-05-21 |
ES2715748T3 (es) | 2019-06-06 |
CN107109176A (zh) | 2017-08-29 |
MX2017008266A (es) | 2017-10-02 |
BR112017013230A2 (pt) | 2018-01-09 |
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