JP2012517503A - 室温硬化性エポキシ接着剤 - Google Patents
室温硬化性エポキシ接着剤 Download PDFInfo
- Publication number
- JP2012517503A JP2012517503A JP2011549233A JP2011549233A JP2012517503A JP 2012517503 A JP2012517503 A JP 2012517503A JP 2011549233 A JP2011549233 A JP 2011549233A JP 2011549233 A JP2011549233 A JP 2011549233A JP 2012517503 A JP2012517503 A JP 2012517503A
- Authority
- JP
- Japan
- Prior art keywords
- adhesive
- amine
- equivalent
- curing agent
- weight
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Ceased
Links
- 229920006332 epoxy adhesive Polymers 0.000 title abstract description 7
- 150000001412 amines Chemical class 0.000 claims abstract description 110
- 239000000853 adhesive Substances 0.000 claims abstract description 84
- 230000001070 adhesive effect Effects 0.000 claims abstract description 82
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 74
- 150000001875 compounds Chemical class 0.000 claims abstract description 30
- -1 acetoacetoxy Chemical group 0.000 claims abstract description 28
- 229920000647 polyepoxide Polymers 0.000 claims abstract description 28
- 239000003822 epoxy resin Substances 0.000 claims abstract description 26
- 239000003054 catalyst Substances 0.000 claims abstract description 25
- 229910052751 metal Inorganic materials 0.000 claims abstract description 24
- 239000002184 metal Substances 0.000 claims abstract description 24
- 150000003839 salts Chemical class 0.000 claims abstract description 20
- 239000000203 mixture Substances 0.000 claims description 46
- 239000004593 Epoxy Substances 0.000 claims description 23
- 125000004432 carbon atom Chemical group C* 0.000 claims description 18
- 229920000642 polymer Polymers 0.000 claims description 16
- 229920005989 resin Polymers 0.000 claims description 14
- 239000011347 resin Substances 0.000 claims description 14
- 238000010998 test method Methods 0.000 claims description 14
- 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 claims description 11
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 claims description 11
- 238000002156 mixing Methods 0.000 claims description 11
- 229920000570 polyether Polymers 0.000 claims description 10
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 claims description 8
- 229930195733 hydrocarbon Natural products 0.000 claims description 7
- 150000002430 hydrocarbons Chemical class 0.000 claims description 7
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 6
- 239000012745 toughening agent Substances 0.000 claims description 6
- 229920000459 Nitrile rubber Polymers 0.000 claims description 5
- 229940106691 bisphenol a Drugs 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229920003986 novolac Polymers 0.000 claims description 5
- IRLQAJPIHBZROB-UHFFFAOYSA-N buta-2,3-dienenitrile Chemical compound C=C=CC#N IRLQAJPIHBZROB-UHFFFAOYSA-N 0.000 claims description 4
- 238000001879 gelation Methods 0.000 claims description 4
- 239000004215 Carbon black (E152) Substances 0.000 claims description 3
- PUQLFUHLKNBKQQ-UHFFFAOYSA-L calcium;trifluoromethanesulfonate Chemical compound [Ca+2].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F PUQLFUHLKNBKQQ-UHFFFAOYSA-L 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 239000011258 core-shell material Substances 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
- 239000003292 glue Substances 0.000 claims 1
- GQWWGRUJOCIUKI-UHFFFAOYSA-N 2-[3-(2-methyl-1-oxopyrrolo[1,2-a]pyrazin-3-yl)propyl]guanidine Chemical compound O=C1N(C)C(CCCN=C(N)N)=CN2C=CC=C21 GQWWGRUJOCIUKI-UHFFFAOYSA-N 0.000 abstract 4
- 239000000499 gel Substances 0.000 description 13
- 239000000463 material Substances 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 239000011324 bead Substances 0.000 description 6
- 229920001577 copolymer Polymers 0.000 description 5
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 5
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- 230000009477 glass transition Effects 0.000 description 4
- 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 4
- 238000000034 method Methods 0.000 description 4
- 239000004848 polyfunctional curative Substances 0.000 description 4
- 125000006850 spacer group Chemical group 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- KUBDPQJOLOUJRM-UHFFFAOYSA-N 2-(chloromethyl)oxirane;4-[2-(4-hydroxyphenyl)propan-2-yl]phenol Chemical compound ClCC1CO1.C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 KUBDPQJOLOUJRM-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- FVCSARBUZVPSQF-UHFFFAOYSA-N 5-(2,4-dioxooxolan-3-yl)-7-methyl-3a,4,5,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C(C(OC2=O)=O)C2C(C)=CC1C1C(=O)COC1=O FVCSARBUZVPSQF-UHFFFAOYSA-N 0.000 description 3
- 125000002723 alicyclic group Chemical group 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 239000000945 filler Substances 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 238000009863 impact test Methods 0.000 description 3
- AHDSRXYHVZECER-UHFFFAOYSA-N 2,4,6-tris[(dimethylamino)methyl]phenol Chemical compound CN(C)CC1=CC(CN(C)C)=C(O)C(CN(C)C)=C1 AHDSRXYHVZECER-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 239000004825 One-part adhesive Substances 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 2
- ZCCIPPOKBCJFDN-UHFFFAOYSA-N calcium nitrate Chemical compound [Ca+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ZCCIPPOKBCJFDN-UHFFFAOYSA-N 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 239000000806 elastomer Substances 0.000 description 2
- 125000003700 epoxy group Chemical group 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- 150000004677 hydrates Chemical class 0.000 description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 238000005304 joining Methods 0.000 description 2
- HSZCZNFXUDYRKD-UHFFFAOYSA-M lithium iodide Chemical compound [Li+].[I-] HSZCZNFXUDYRKD-UHFFFAOYSA-M 0.000 description 2
- IIPYXGDZVMZOAP-UHFFFAOYSA-N lithium nitrate Chemical compound [Li+].[O-][N+]([O-])=O IIPYXGDZVMZOAP-UHFFFAOYSA-N 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000004005 microsphere Substances 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 229920000058 polyacrylate Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 230000003068 static effect Effects 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- WTFAGPBUAGFMQX-UHFFFAOYSA-N 1-[2-[2-(2-aminopropoxy)propoxy]propoxy]propan-2-amine Chemical compound CC(N)COCC(C)OCC(C)OCC(C)N WTFAGPBUAGFMQX-UHFFFAOYSA-N 0.000 description 1
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 1
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 1
- JZUHIOJYCPIVLQ-UHFFFAOYSA-N 2-methylpentane-1,5-diamine Chemical compound NCC(C)CCCN JZUHIOJYCPIVLQ-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 241001070941 Castanea Species 0.000 description 1
- 235000014036 Castanea Nutrition 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical group S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- 239000003522 acrylic cement Substances 0.000 description 1
- 229920006243 acrylic copolymer Polymers 0.000 description 1
- 239000002318 adhesion promoter Substances 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- RREGISFBPQOLTM-UHFFFAOYSA-N alumane;trihydrate Chemical compound O.O.O.[AlH3] RREGISFBPQOLTM-UHFFFAOYSA-N 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 239000011449 brick Substances 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000000378 calcium silicate Substances 0.000 description 1
- 229910052918 calcium silicate Inorganic materials 0.000 description 1
- OYACROKNLOSFPA-UHFFFAOYSA-N calcium;dioxido(oxo)silane Chemical compound [Ca+2].[O-][Si]([O-])=O OYACROKNLOSFPA-UHFFFAOYSA-N 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- UYMKPFRHYYNDTL-UHFFFAOYSA-N ethenamine Chemical compound NC=C UYMKPFRHYYNDTL-UHFFFAOYSA-N 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 229910021485 fumed silica Inorganic materials 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 150000002462 imidazolines Chemical class 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000001023 inorganic pigment Substances 0.000 description 1
- 150000004694 iodide salts Chemical class 0.000 description 1
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N iron oxide Inorganic materials [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 1
- 229910052747 lanthanoid Inorganic materials 0.000 description 1
- WGJJZRVGLPOKQT-UHFFFAOYSA-K lanthanum(3+);trifluoromethanesulfonate Chemical compound [La+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F WGJJZRVGLPOKQT-UHFFFAOYSA-K 0.000 description 1
- FYDKNKUEBJQCCN-UHFFFAOYSA-N lanthanum(3+);trinitrate Chemical compound [La+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O FYDKNKUEBJQCCN-UHFFFAOYSA-N 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 239000008204 material by function Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- MEFBJEMVZONFCJ-UHFFFAOYSA-N molybdate Chemical compound [O-][Mo]([O-])(=O)=O MEFBJEMVZONFCJ-UHFFFAOYSA-N 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- AQGNVWRYTKPRMR-UHFFFAOYSA-N n'-[2-[2-[2-[2-(2-aminoethylamino)ethylamino]ethylamino]ethylamino]ethyl]ethane-1,2-diamine Chemical compound NCCNCCNCCNCCNCCNCCN AQGNVWRYTKPRMR-UHFFFAOYSA-N 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012860 organic pigment Substances 0.000 description 1
- NDLPOXTZKUMGOV-UHFFFAOYSA-N oxo(oxoferriooxy)iron hydrate Chemical compound O.O=[Fe]O[Fe]=O NDLPOXTZKUMGOV-UHFFFAOYSA-N 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical class OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 238000005498 polishing Methods 0.000 description 1
- 229920002587 poly(1,3-butadiene) polymer Polymers 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
- 239000006254 rheological additive Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 230000000930 thermomechanical effect Effects 0.000 description 1
- 150000003567 thiocyanates Chemical class 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- 150000008648 triflates Chemical class 0.000 description 1
- 238000003466 welding Methods 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Epoxy Resins (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US15044309P | 2009-02-06 | 2009-02-06 | |
| US61/150,443 | 2009-02-06 | ||
| PCT/US2010/023033 WO2010091072A1 (en) | 2009-02-06 | 2010-02-03 | Room temperature curing epoxy adhesive |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2012517503A true JP2012517503A (ja) | 2012-08-02 |
| JP2012517503A5 JP2012517503A5 (https=) | 2013-03-28 |
Family
ID=42028095
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011549233A Ceased JP2012517503A (ja) | 2009-02-06 | 2010-02-03 | 室温硬化性エポキシ接着剤 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US20120024477A1 (https=) |
| EP (1) | EP2393864A1 (https=) |
| JP (1) | JP2012517503A (https=) |
| CN (1) | CN102307925B (https=) |
| WO (1) | WO2010091072A1 (https=) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2013535561A (ja) * | 2010-08-10 | 2013-09-12 | スリーエム イノベイティブ プロパティズ カンパニー | エポキシ構造接着剤 |
| JP2014501805A (ja) * | 2010-11-12 | 2014-01-23 | スリーエム イノベイティブ プロパティズ カンパニー | 硬化性組成物及び硬化済み組成物 |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9067395B2 (en) | 2010-08-20 | 2015-06-30 | 3M Innovative Properties Company | Low temperature curable epoxy tape and method of making same |
| BR112013014592A2 (pt) * | 2010-12-29 | 2016-09-20 | 3M Innovative Properties Co | adesivos híbridos estruturais |
| JP6130502B2 (ja) | 2012-07-03 | 2017-05-17 | スリーエム イノベイティブ プロパティズ カンパニー | 構造化ハイブリッド接着剤物品の製造方法 |
| ES2625552T3 (es) * | 2014-06-17 | 2017-07-19 | 3M Innovative Properties Company | Composición de adhesivo epoxídico de curado rápido |
| CN104371627A (zh) * | 2014-11-17 | 2015-02-25 | 卡本复合材料（天津）有限公司 | 一种低温抗结晶型结构胶及其制备方法 |
| EP3162829B1 (en) | 2015-10-29 | 2018-08-15 | 3M Innovative Properties Company | Rapid curing and high thixotropy epoxy adhesive compositions |
| US10683441B2 (en) | 2016-03-02 | 2020-06-16 | 3M Innovative Properties Company | Composition including epoxy adhesive and aluminum flakes and method for using the same |
| US20170290762A1 (en) * | 2016-04-08 | 2017-10-12 | Empire Technology Development Llc | Method and Composition for Dag Mitigation on Hair |
| US12486437B2 (en) | 2019-12-19 | 2025-12-02 | 3M Innovative Properties Company | Shimming adhesive |
| US20220314559A1 (en) * | 2021-03-31 | 2022-10-06 | Chris Durham | Rv and trailer composite panel manufacturing process with interlocking connections assembly system |
Citations (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5447734A (en) * | 1977-09-22 | 1979-04-14 | Matsushita Electric Ind Co Ltd | Method of extruding rapidddrying epoxy resin adhesive and device therefor |
| JPS62227980A (ja) * | 1986-03-21 | 1987-10-06 | アシユランド・オイル・インコ−ポレ−テツド | 構造用二成分接着剤 |
| JPS62243616A (ja) * | 1986-04-17 | 1987-10-24 | Nitto Electric Ind Co Ltd | 厚膜形成型エポキシ樹脂組成物 |
| JPH05156225A (ja) * | 1991-12-03 | 1993-06-22 | Aica Kogyo Co Ltd | 二液型接着剤 |
| JPH0953053A (ja) * | 1995-08-09 | 1997-02-25 | Furukawa Electric Co Ltd:The | ２液混合硬化型樹脂の混合状態判定方法 |
| JPH09296027A (ja) * | 1996-05-07 | 1997-11-18 | Toyo Ink Mfg Co Ltd | 硬化性樹脂組成物 |
| JP2000309625A (ja) * | 1999-04-26 | 2000-11-07 | Toyo Ink Mfg Co Ltd | 硬化性樹脂組成物 |
| JP2001151862A (ja) * | 1999-11-22 | 2001-06-05 | Tosoh Corp | エポキシ樹脂組成物 |
| JP2003041227A (ja) * | 2001-05-21 | 2003-02-13 | Sanyo Chem Ind Ltd | コンタクト接着剤 |
| JP2004183334A (ja) * | 2002-12-04 | 2004-07-02 | Jdc Corp | エポキシ樹脂系二液型接着剤硬化工法 |
| JP2005200948A (ja) * | 2004-01-16 | 2005-07-28 | Sanyo Chem Ind Ltd | グラウト材硬化物 |
| JP2007191527A (ja) * | 2006-01-18 | 2007-08-02 | Japan Epoxy Resin Kk | エポキシ樹脂組成物 |
| JP2008156605A (ja) * | 2006-10-20 | 2008-07-10 | Air Products & Chemicals Inc | 低温硬化用途向けの硬化剤 |
| WO2008089410A1 (en) * | 2007-01-18 | 2008-07-24 | 3M Innovative Properties Company | High strength epoxy adhesive and use thereof |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4126505A (en) * | 1974-11-05 | 1978-11-21 | Ciba-Geigy Corporation | Adhesive compositions |
| US4240566A (en) * | 1979-09-17 | 1980-12-23 | Whirlco, Inc. | Captive mixing cap arrangement for multiple chamber container |
| US5735320A (en) * | 1996-08-21 | 1998-04-07 | The Sherwin-Williams Company | Dispenser for a two-part composition |
| US6872762B2 (en) * | 2000-07-13 | 2005-03-29 | Loctite (R&D) Limited | Epoxy resin composition with solid organic acid |
| US20040072927A1 (en) * | 2002-10-14 | 2004-04-15 | Hachikian Zakar Raffi | Two-part epoxy adhesives with improved flexibility and process for making and using same |
| CA2561385A1 (en) * | 2004-03-30 | 2005-10-13 | Kaneka Corporation | Hardenable composition |
| GB2417030A (en) * | 2004-08-05 | 2006-02-15 | Huntsman Advanced Materials | Fire retardant composition |
| ES2662646T3 (es) * | 2008-06-12 | 2018-04-09 | Henkel IP & Holding GmbH | Composiciones adhesivas epóxicas estructurales de dos partes, altamente reforzadas, de nueva generación |
| EP2321370B1 (en) * | 2008-07-23 | 2017-03-15 | 3M Innovative Properties Company | Two-part epoxy-based structural adhesives |
| CN102159615B (zh) * | 2008-07-23 | 2014-10-01 | 3M创新有限公司 | 两部分的环氧基结构粘合剂 |
| CN103068946B (zh) * | 2010-08-10 | 2015-05-06 | 3M创新有限公司 | 环氧树脂结构粘合剂 |
-
2010
- 2010-02-03 CN CN2010800065627A patent/CN102307925B/zh not_active Expired - Fee Related
- 2010-02-03 EP EP10703757A patent/EP2393864A1/en not_active Withdrawn
- 2010-02-03 US US13/147,380 patent/US20120024477A1/en not_active Abandoned
- 2010-02-03 JP JP2011549233A patent/JP2012517503A/ja not_active Ceased
- 2010-02-03 WO PCT/US2010/023033 patent/WO2010091072A1/en not_active Ceased
Patent Citations (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5447734A (en) * | 1977-09-22 | 1979-04-14 | Matsushita Electric Ind Co Ltd | Method of extruding rapidddrying epoxy resin adhesive and device therefor |
| JPS62227980A (ja) * | 1986-03-21 | 1987-10-06 | アシユランド・オイル・インコ−ポレ−テツド | 構造用二成分接着剤 |
| JPS62243616A (ja) * | 1986-04-17 | 1987-10-24 | Nitto Electric Ind Co Ltd | 厚膜形成型エポキシ樹脂組成物 |
| JPH05156225A (ja) * | 1991-12-03 | 1993-06-22 | Aica Kogyo Co Ltd | 二液型接着剤 |
| JPH0953053A (ja) * | 1995-08-09 | 1997-02-25 | Furukawa Electric Co Ltd:The | ２液混合硬化型樹脂の混合状態判定方法 |
| JPH09296027A (ja) * | 1996-05-07 | 1997-11-18 | Toyo Ink Mfg Co Ltd | 硬化性樹脂組成物 |
| JP2000309625A (ja) * | 1999-04-26 | 2000-11-07 | Toyo Ink Mfg Co Ltd | 硬化性樹脂組成物 |
| JP2001151862A (ja) * | 1999-11-22 | 2001-06-05 | Tosoh Corp | エポキシ樹脂組成物 |
| JP2003041227A (ja) * | 2001-05-21 | 2003-02-13 | Sanyo Chem Ind Ltd | コンタクト接着剤 |
| JP2004183334A (ja) * | 2002-12-04 | 2004-07-02 | Jdc Corp | エポキシ樹脂系二液型接着剤硬化工法 |
| JP2005200948A (ja) * | 2004-01-16 | 2005-07-28 | Sanyo Chem Ind Ltd | グラウト材硬化物 |
| JP2007191527A (ja) * | 2006-01-18 | 2007-08-02 | Japan Epoxy Resin Kk | エポキシ樹脂組成物 |
| JP2008156605A (ja) * | 2006-10-20 | 2008-07-10 | Air Products & Chemicals Inc | 低温硬化用途向けの硬化剤 |
| WO2008089410A1 (en) * | 2007-01-18 | 2008-07-24 | 3M Innovative Properties Company | High strength epoxy adhesive and use thereof |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2013535561A (ja) * | 2010-08-10 | 2013-09-12 | スリーエム イノベイティブ プロパティズ カンパニー | エポキシ構造接着剤 |
| JP2014501805A (ja) * | 2010-11-12 | 2014-01-23 | スリーエム イノベイティブ プロパティズ カンパニー | 硬化性組成物及び硬化済み組成物 |
Also Published As
| Publication number | Publication date |
|---|---|
| US20120024477A1 (en) | 2012-02-02 |
| CN102307925B (zh) | 2013-11-06 |
| CN102307925A (zh) | 2012-01-04 |
| EP2393864A1 (en) | 2011-12-14 |
| WO2010091072A1 (en) | 2010-08-12 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP5756178B2 (ja) | エポキシ構造接着剤 | |
| JP2012517503A (ja) | 室温硬化性エポキシ接着剤 | |
| CN102159615B (zh) | 两部分的环氧基结构粘合剂 | |
| JP5840219B2 (ja) | 硬化性組成物及び硬化済み組成物 | |
| JP5784134B2 (ja) | 硬化性組成物 | |
| JP5530524B2 (ja) | 硬化性及び硬化済み接着剤組成物 | |
| CN103270073A (zh) | 可固化粘合剂组合物 | |
| CN102171303B (zh) | 快速固化的吸油性环氧基结构粘合剂 | |
| CN101578346A (zh) | 高强度环氧树脂粘结剂及其用途 | |
| JP5752126B2 (ja) | 硬化性及び硬化済み接着剤組成物 | |
| EP3824039B1 (en) | Method for strengthening of metal structures using toughened 2c-epoxy adhesives | |
| EP3423539B1 (en) | Composition including epoxy adhesive and aluminum flakes and method for making the same | |
| TWI907563B (zh) | 基於環氧樹脂之兩部分結構性黏著劑組成物 | |
| US11958938B2 (en) | Curable composition | |
| JP7738558B2 (ja) | ２剤型硬化性接着剤 | |
| JP2025530806A (ja) | エポキシド化合物のブレンドに基づく２成分組成物 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20130204 |
|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20130204 |
|
| A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20131121 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20131126 |
|
| A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20140225 |
|
| A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20140304 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20140526 |
|
| A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20140812 |
|
| A045 | Written measure of dismissal of application [lapsed due to lack of payment] |
Free format text: JAPANESE INTERMEDIATE CODE: A045 Effective date: 20141216 |