CA2917013A1 - High modulus epoxy adhesives for shimming applications - Google Patents
High modulus epoxy adhesives for shimming applications Download PDFInfo
- Publication number
- CA2917013A1 CA2917013A1 CA2917013A CA2917013A CA2917013A1 CA 2917013 A1 CA2917013 A1 CA 2917013A1 CA 2917013 A CA2917013 A CA 2917013A CA 2917013 A CA2917013 A CA 2917013A CA 2917013 A1 CA2917013 A1 CA 2917013A1
- Authority
- CA
- Canada
- Prior art keywords
- composition
- curative
- primary amino
- epoxy
- group
- 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.)
- Abandoned
Links
- 229920006332 epoxy adhesive Polymers 0.000 title description 2
- 239000000203 mixture Substances 0.000 claims abstract description 160
- 239000003822 epoxy resin Substances 0.000 claims abstract description 69
- 229920000647 polyepoxide Polymers 0.000 claims abstract description 69
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 46
- 239000004593 Epoxy Substances 0.000 claims abstract description 38
- 239000004721 Polyphenylene oxide Substances 0.000 claims abstract description 25
- 229920000570 polyether Polymers 0.000 claims abstract description 25
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 20
- 229920000768 polyamine Polymers 0.000 claims abstract description 20
- -1 cyclic amine Chemical class 0.000 claims abstract description 17
- 125000004103 aminoalkyl group Chemical group 0.000 claims abstract description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 12
- 125000005647 linker group Chemical group 0.000 claims abstract description 4
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 claims description 32
- 125000003118 aryl group Chemical group 0.000 claims description 17
- 125000005250 alkyl acrylate group Chemical group 0.000 claims description 14
- 239000000835 fiber Substances 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 11
- 229920005989 resin Polymers 0.000 claims description 11
- 239000011347 resin Substances 0.000 claims description 11
- 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 9
- 239000002131 composite material Substances 0.000 claims description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- LJBWJFWNFUKAGS-UHFFFAOYSA-N 2-[bis(2-hydroxyphenyl)methyl]phenol Chemical compound OC1=CC=CC=C1C(C=1C(=CC=CC=1)O)C1=CC=CC=C1O LJBWJFWNFUKAGS-UHFFFAOYSA-N 0.000 claims description 6
- 229910052751 metal Inorganic materials 0.000 claims description 6
- 239000002184 metal Substances 0.000 claims description 6
- 239000000047 product Substances 0.000 claims description 6
- 125000001931 aliphatic group Chemical group 0.000 claims description 5
- 239000007795 chemical reaction product Substances 0.000 claims description 5
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 239000011159 matrix material Substances 0.000 claims description 4
- 239000011248 coating agent Substances 0.000 claims description 3
- 238000000576 coating method Methods 0.000 claims description 3
- 239000003973 paint Substances 0.000 claims description 3
- 239000011253 protective coating Substances 0.000 claims description 3
- 238000007039 two-step reaction Methods 0.000 claims description 3
- 238000007259 addition reaction Methods 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 description 26
- 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 25
- 239000000945 filler Substances 0.000 description 20
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 15
- 239000000463 material Substances 0.000 description 14
- 125000000466 oxiranyl group Chemical group 0.000 description 14
- 239000000126 substance Substances 0.000 description 12
- 150000001412 amines Chemical class 0.000 description 11
- 239000000654 additive Substances 0.000 description 9
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 8
- 125000004122 cyclic group Chemical group 0.000 description 7
- 239000003085 diluting agent Substances 0.000 description 7
- 238000009472 formulation Methods 0.000 description 7
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 7
- 239000012745 toughening agent Substances 0.000 description 7
- 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 6
- 125000002947 alkylene group Chemical group 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 239000000049 pigment Substances 0.000 description 6
- 239000002318 adhesion promoter Substances 0.000 description 5
- 125000003368 amide group Chemical group 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 238000007906 compression Methods 0.000 description 5
- 230000006835 compression Effects 0.000 description 5
- 229910021485 fumed silica Inorganic materials 0.000 description 5
- 239000012784 inorganic fiber Substances 0.000 description 5
- 239000003607 modifier Substances 0.000 description 5
- 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 4
- 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 4
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 4
- 239000005977 Ethylene Substances 0.000 description 4
- 125000000732 arylene group Chemical group 0.000 description 4
- 150000004985 diamines Chemical class 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 239000004615 ingredient Substances 0.000 description 4
- 239000004005 microsphere Substances 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinyl group Chemical group C1(O)=CC(O)=CC=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- 239000000080 wetting agent Substances 0.000 description 4
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical group CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 3
- XUSNPFGLKGCWGN-UHFFFAOYSA-N 3-[4-(3-aminopropyl)piperazin-1-yl]propan-1-amine Chemical compound NCCCN1CCN(CCCN)CC1 XUSNPFGLKGCWGN-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- 239000000853 adhesive Substances 0.000 description 3
- 230000001070 adhesive effect Effects 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- 239000003063 flame retardant Substances 0.000 description 3
- 230000002209 hydrophobic effect Effects 0.000 description 3
- 239000011490 mineral wool Substances 0.000 description 3
- 229920003986 novolac Polymers 0.000 description 3
- 150000002989 phenols Chemical class 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 3
- KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 description 2
- 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 2
- DGUJJOYLOCXENZ-UHFFFAOYSA-N 4-[2-[4-(oxiran-2-ylmethoxy)phenyl]propan-2-yl]phenol Chemical compound C=1C=C(OCC2OC2)C=CC=1C(C)(C)C1=CC=C(O)C=C1 DGUJJOYLOCXENZ-UHFFFAOYSA-N 0.000 description 2
- 229910002012 Aerosil® Inorganic materials 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-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
- 239000004215 Carbon black (E152) Substances 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
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- MXRIRQGCELJRSN-UHFFFAOYSA-N O.O.O.[Al] Chemical compound O.O.O.[Al] MXRIRQGCELJRSN-UHFFFAOYSA-N 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- 239000004760 aramid Substances 0.000 description 2
- 229920006231 aramid fiber Polymers 0.000 description 2
- 150000001491 aromatic compounds Chemical class 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- VEIOBOXBGYWJIT-UHFFFAOYSA-N cyclohexane;methanol Chemical compound OC.OC.C1CCCCC1 VEIOBOXBGYWJIT-UHFFFAOYSA-N 0.000 description 2
- 239000002274 desiccant Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 239000005350 fused silica glass Substances 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- 239000003365 glass fiber Substances 0.000 description 2
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000011147 inorganic material Substances 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 150000002780 morpholines Chemical group 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- 229920001281 polyalkylene Polymers 0.000 description 2
- 229920000098 polyolefin Polymers 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 150000004756 silanes Chemical class 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical group CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N titanium dioxide Inorganic materials O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 125000006839 xylylene group Chemical group 0.000 description 2
- SLBDZIKCTKBNEB-UHFFFAOYSA-N 1,1-diphenylpentane-2,2-diol Chemical compound C=1C=CC=CC=1C(C(O)(O)CCC)C1=CC=CC=C1 SLBDZIKCTKBNEB-UHFFFAOYSA-N 0.000 description 1
- XPRCUIHVISJANL-UHFFFAOYSA-N 1,3,3-triphenylpropan-1-ol Chemical compound C=1C=CC=CC=1C(O)CC(C=1C=CC=CC=1)C1=CC=CC=C1 XPRCUIHVISJANL-UHFFFAOYSA-N 0.000 description 1
- KLQLCYSCZWVHPO-UHFFFAOYSA-N 2,2-diphenylcyclohexan-1-ol Chemical compound OC1CCCCC1(C=1C=CC=CC=1)C1=CC=CC=C1 KLQLCYSCZWVHPO-UHFFFAOYSA-N 0.000 description 1
- LCVCUJWKJNFDMY-UHFFFAOYSA-N 2,2-diphenylpropane-1,1-diol Chemical compound C=1C=CC=CC=1C(C(O)O)(C)C1=CC=CC=C1 LCVCUJWKJNFDMY-UHFFFAOYSA-N 0.000 description 1
- 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 1
- RLGJEXKWRUSFFN-UHFFFAOYSA-N 2-(1,1-diphenylpentyl)phenol Chemical compound C=1C=CC=CC=1C(C=1C(=CC=CC=1)O)(CCCC)C1=CC=CC=C1 RLGJEXKWRUSFFN-UHFFFAOYSA-N 0.000 description 1
- BBBUAWSVILPJLL-UHFFFAOYSA-N 2-(2-ethylhexoxymethyl)oxirane Chemical compound CCCCC(CC)COCC1CO1 BBBUAWSVILPJLL-UHFFFAOYSA-N 0.000 description 1
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- RNLHGQLZWXBQNY-UHFFFAOYSA-N 3-(aminomethyl)-3,5,5-trimethylcyclohexan-1-amine Chemical compound CC1(C)CC(N)CC(C)(CN)C1 RNLHGQLZWXBQNY-UHFFFAOYSA-N 0.000 description 1
- KKNYDJZIOUFYLA-UHFFFAOYSA-N 4,4-diphenylbutan-2-ol Chemical compound C=1C=CC=CC=1C(CC(O)C)C1=CC=CC=C1 KKNYDJZIOUFYLA-UHFFFAOYSA-N 0.000 description 1
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- 239000009261 D 400 Substances 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical group CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
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- 239000007983 Tris buffer Substances 0.000 description 1
- 229920000690 Tyvek Polymers 0.000 description 1
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- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 150000002895 organic esters Chemical class 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
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- XZTOTRSSGPPNTB-UHFFFAOYSA-N phosphono dihydrogen phosphate;1,3,5-triazine-2,4,6-triamine Chemical compound NC1=NC(N)=NC(N)=N1.OP(O)(=O)OP(O)(O)=O XZTOTRSSGPPNTB-UHFFFAOYSA-N 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- XFZRQAZGUOTJCS-UHFFFAOYSA-N phosphoric acid;1,3,5-triazine-2,4,6-triamine Chemical compound OP(O)(O)=O.NC1=NC(N)=NC(N)=N1 XFZRQAZGUOTJCS-UHFFFAOYSA-N 0.000 description 1
- QVJYHZQHDMNONA-UHFFFAOYSA-N phosphoric acid;1,3,5-triazine-2,4,6-triamine Chemical compound OP(O)(O)=O.NC1=NC(N)=NC(N)=N1.NC1=NC(N)=NC(N)=N1 QVJYHZQHDMNONA-UHFFFAOYSA-N 0.000 description 1
- 150000004885 piperazines Chemical group 0.000 description 1
- 229920000962 poly(amidoamine) Polymers 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 229920006122 polyamide resin Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 238000010944 pre-mature reactiony Methods 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- BHRZNVHARXXAHW-UHFFFAOYSA-N sec-butylamine Chemical compound CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 0.000 description 1
- 150000003335 secondary amines Chemical group 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 229910002029 synthetic silica gel Inorganic materials 0.000 description 1
- 125000001302 tertiary amino group Chemical group 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical class [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000010456 wollastonite Substances 0.000 description 1
- 229910052882 wollastonite Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc 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
- B32B7/00—Layered products characterised by the relation between layers; Layered products characterised by the relative orientation of features between layers, or by the relative values of a measurable parameter between layers, i.e. products comprising layers having different physical, chemical or physicochemical properties; Layered products characterised by the interconnection of layers
- B32B7/04—Interconnection of layers
- B32B7/12—Interconnection of layers using interposed adhesives or interposed materials with bonding properties
-
- 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
-
- 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
-
- 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
- B32B2605/00—Vehicles
- B32B2605/18—Aircraft
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)
- Reinforced Plastic Materials (AREA)
- Paints Or Removers (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP13174287.6A EP2818492B1 (en) | 2013-06-28 | 2013-06-28 | use of epoxy-based adhesive compositions for filling gaps |
| EP13174287.6 | 2013-06-28 | ||
| PCT/US2014/044318 WO2014210298A1 (en) | 2013-06-28 | 2014-06-26 | High modulus epoxy adhesives for shimming applications |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2917013A1 true CA2917013A1 (en) | 2014-12-31 |
Family
ID=48703223
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2917013A Abandoned CA2917013A1 (en) | 2013-06-28 | 2014-06-26 | High modulus epoxy adhesives for shimming applications |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US10059862B2 (enExample) |
| EP (1) | EP2818492B1 (enExample) |
| JP (2) | JP2016523313A (enExample) |
| KR (1) | KR20160025567A (enExample) |
| CN (1) | CN105339412B (enExample) |
| BR (1) | BR112015032722A2 (enExample) |
| CA (1) | CA2917013A1 (enExample) |
| ES (1) | ES2673735T3 (enExample) |
| PL (1) | PL2818492T3 (enExample) |
| WO (1) | WO2014210298A1 (enExample) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3239207B1 (en) * | 2016-04-27 | 2021-07-28 | 3M Innovative Properties Company | Curable epoxy compositions |
| EP3375801B1 (en) | 2017-03-16 | 2020-09-30 | 3M Innovative Properties Company | Epoxy casting resin formulation |
| DE202017107320U1 (de) * | 2017-11-30 | 2018-01-17 | Airbus Operations Gmbh | Toleranzkompensations- und Dichtmittel |
| CN112752816B (zh) * | 2018-07-25 | 2022-10-18 | 汉高股份有限及两合公司 | 快速固化的环氧丙烯酸类液体垫片 |
| EP3666842B1 (en) | 2018-12-12 | 2021-09-15 | 3M Innovative Properties Company | High chemical resistant coating as protection against aggressive environment |
| CN110628116B (zh) * | 2019-10-18 | 2021-11-26 | 广东东方管业有限公司 | 阻燃耐磨抗静电聚乙烯复合材料、制备方法及管材 |
| EP4077461A1 (en) | 2019-12-19 | 2022-10-26 | 3M Innovative Properties Company | Shimming adhesive |
| US20230066560A1 (en) * | 2020-12-11 | 2023-03-02 | The Boeing Company | Aircraft with structural gap filler |
| EP4015559B1 (en) * | 2020-12-21 | 2023-07-19 | 3M Innovative Properties Company | Structural adhesive having superior compression properties |
| EP4083102A1 (en) * | 2021-04-30 | 2022-11-02 | 3M Innovative Properties Company | Ultra-light epoxy composition |
| US20250215286A1 (en) | 2022-05-16 | 2025-07-03 | 3M Innovative Properties Company | Adhesion modifier composition, and curable composition and method of bonding including the same |
| WO2025174418A2 (en) * | 2023-09-08 | 2025-08-21 | Cytec Industries Inc. | Ultraviolet (uv) curable shim |
| CN117327433B (zh) * | 2023-09-28 | 2025-05-06 | 江苏进华重防腐涂料有限公司 | 建筑物排水用铸铁管和铸铁配件的环氧漆及其制备和应用 |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6381118A (ja) | 1986-09-25 | 1988-04-12 | Nippon Kayaku Co Ltd | ４核体フェノール類ノボラック型エポキシ化合物の製造法 |
| US4814415A (en) * | 1988-02-19 | 1989-03-21 | Texaco Chemical Company | Oxamidoamine co-curatives in epoxy thermoset adhesives |
| JPH02219814A (ja) * | 1989-02-21 | 1990-09-03 | Sumitomo Bakelite Co Ltd | エポキシ樹脂組成物 |
| JPH03227316A (ja) | 1990-02-01 | 1991-10-08 | Nippon Oil Co Ltd | 耐熱性エポキシ樹脂組成物 |
| JPH03259949A (ja) * | 1990-03-09 | 1991-11-20 | Mitsubishi Petrochem Co Ltd | 注型樹脂組成物 |
| JP3656198B2 (ja) | 1994-04-28 | 2005-06-08 | 東都化成株式会社 | 改良されたノボラック型エポキシ樹脂及び電子部品封止用樹脂組成物 |
| US6632872B1 (en) | 2000-09-19 | 2003-10-14 | 3M Innovative Properties Company | Adhesive compositions including self-assembling molecules, adhesives, articles, and methods |
| JP4869915B2 (ja) | 2006-12-28 | 2012-02-08 | 京セラケミカル株式会社 | 複合防弾板 |
| JP5138506B2 (ja) * | 2007-08-21 | 2013-02-06 | 三菱レイヨン株式会社 | エポキシ樹脂組成物およびプリプレグ |
| US20090099312A1 (en) * | 2007-10-15 | 2009-04-16 | Carl Duane Weber | Amine terminated tougheners for epoxy resin based adhesives and materials |
| CN103232588B (zh) * | 2009-02-09 | 2017-09-26 | 3M创新有限公司 | 两组分液体垫片组合物 |
| DE102009008141A1 (de) * | 2009-02-09 | 2010-08-19 | Saint-Gobain Sekurit Deutschland Gmbh & Co. Kg | Transparenter Glaskörper, Verfahren zu dessen Herstellung und dessen Verwendung |
| JP5473585B2 (ja) | 2009-12-24 | 2014-04-16 | 三菱レイヨン株式会社 | エポキシ樹脂組成物 |
| WO2012067092A1 (ja) * | 2010-11-17 | 2012-05-24 | 日本化薬株式会社 | 透明シート用エポキシ樹脂組成物及びその硬化物 |
| EP2495271B1 (en) | 2011-03-04 | 2014-04-23 | 3M Innovative Properties Co. | Polyether hybrid epoxy curatives |
-
2013
- 2013-06-28 ES ES13174287.6T patent/ES2673735T3/es active Active
- 2013-06-28 EP EP13174287.6A patent/EP2818492B1/en active Active
- 2013-06-28 PL PL13174287T patent/PL2818492T3/pl unknown
-
2014
- 2014-06-26 CA CA2917013A patent/CA2917013A1/en not_active Abandoned
- 2014-06-26 BR BR112015032722A patent/BR112015032722A2/pt not_active Application Discontinuation
- 2014-06-26 KR KR1020167001817A patent/KR20160025567A/ko not_active Withdrawn
- 2014-06-26 JP JP2016524192A patent/JP2016523313A/ja active Pending
- 2014-06-26 US US14/900,895 patent/US10059862B2/en active Active
- 2014-06-26 CN CN201480036554.5A patent/CN105339412B/zh active Active
- 2014-06-26 WO PCT/US2014/044318 patent/WO2014210298A1/en not_active Ceased
-
2018
- 2018-04-06 JP JP2018073742A patent/JP6710233B2/ja active Active
Also Published As
| Publication number | Publication date |
|---|---|
| JP2016523313A (ja) | 2016-08-08 |
| ES2673735T3 (es) | 2018-06-25 |
| JP2018123336A (ja) | 2018-08-09 |
| US20160152879A1 (en) | 2016-06-02 |
| WO2014210298A1 (en) | 2014-12-31 |
| EP2818492B1 (en) | 2018-04-04 |
| KR20160025567A (ko) | 2016-03-08 |
| CN105339412A (zh) | 2016-02-17 |
| US10059862B2 (en) | 2018-08-28 |
| PL2818492T3 (pl) | 2018-07-31 |
| JP6710233B2 (ja) | 2020-06-17 |
| EP2818492A1 (en) | 2014-12-31 |
| BR112015032722A2 (pt) | 2017-07-25 |
| CN105339412B (zh) | 2018-01-05 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Dead |
Effective date: 20200831 |