CA2449590C - Heat resistant, impact resistant, acrylic/epoxy adhesives - Google Patents
Heat resistant, impact resistant, acrylic/epoxy adhesives Download PDFInfo
- Publication number
- CA2449590C CA2449590C CA002449590A CA2449590A CA2449590C CA 2449590 C CA2449590 C CA 2449590C CA 002449590 A CA002449590 A CA 002449590A CA 2449590 A CA2449590 A CA 2449590A CA 2449590 C CA2449590 C CA 2449590C
- Authority
- CA
- Canada
- Prior art keywords
- based monomer
- adhesive
- acrylic
- monomer
- epoxy
- 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.)
- Expired - Lifetime
Links
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 title claims abstract description 89
- 229920006332 epoxy adhesive Polymers 0.000 title description 5
- 239000000178 monomer Substances 0.000 claims abstract description 181
- 239000000853 adhesive Substances 0.000 claims abstract description 162
- 230000001070 adhesive effect Effects 0.000 claims abstract description 160
- 239000004593 Epoxy Substances 0.000 claims abstract description 85
- 239000003054 catalyst Substances 0.000 claims abstract description 48
- 239000004609 Impact Modifier Substances 0.000 claims abstract description 43
- 229920005989 resin Polymers 0.000 claims abstract description 33
- 239000011347 resin Substances 0.000 claims abstract description 33
- 230000001588 bifunctional effect Effects 0.000 claims abstract description 27
- 239000000203 mixture Substances 0.000 claims description 45
- 229920001971 elastomer Polymers 0.000 claims description 38
- 239000000806 elastomer Substances 0.000 claims description 37
- 239000003638 chemical reducing agent Substances 0.000 claims description 36
- 239000007800 oxidant agent Substances 0.000 claims description 30
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims description 27
- 150000001875 compounds Chemical class 0.000 claims description 25
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical group COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 24
- 239000012190 activator Substances 0.000 claims description 20
- -1 hydroxyethyl toluidine Chemical class 0.000 claims description 15
- 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 12
- 150000002978 peroxides Chemical class 0.000 claims description 12
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical group COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 11
- 239000007859 condensation product Substances 0.000 claims description 10
- 239000004342 Benzoyl peroxide Substances 0.000 claims description 9
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical group C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 claims description 9
- 235000019400 benzoyl peroxide Nutrition 0.000 claims description 9
- 229920000578 graft copolymer Polymers 0.000 claims description 9
- 239000011258 core-shell material Substances 0.000 claims description 8
- 238000002156 mixing Methods 0.000 claims description 8
- 150000001412 amines Chemical class 0.000 claims description 7
- 150000002148 esters Chemical class 0.000 claims description 7
- POLZHVHESHDZRD-UHFFFAOYSA-N 2-hydroxyethyl 2-methylprop-2-enoate;phosphoric acid Chemical compound OP(O)(O)=O.CC(=C)C(=O)OCCO POLZHVHESHDZRD-UHFFFAOYSA-N 0.000 claims description 6
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 6
- 150000002432 hydroperoxides Chemical class 0.000 claims description 6
- 150000002976 peresters Chemical class 0.000 claims description 6
- 150000004965 peroxy acids Chemical class 0.000 claims description 6
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical group C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 claims description 4
- 230000009477 glass transition Effects 0.000 claims description 4
- 229920000536 2-Acrylamido-2-methylpropane sulfonic acid Polymers 0.000 claims description 3
- XHZPRMZZQOIPDS-UHFFFAOYSA-N 2-Methyl-2-[(1-oxo-2-propenyl)amino]-1-propanesulfonic acid Chemical compound OS(=O)(=O)CC(C)(C)NC(=O)C=C XHZPRMZZQOIPDS-UHFFFAOYSA-N 0.000 claims description 3
- 229920002943 EPDM rubber Polymers 0.000 claims description 3
- 125000004925 dihydropyridyl group Chemical group N1(CC=CC=C1)* 0.000 claims description 2
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical group CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 claims description 2
- 150000001448 anilines Chemical class 0.000 claims 3
- 229930185605 Bisphenol Natural products 0.000 claims 1
- 125000005395 methacrylic acid group Chemical group 0.000 claims 1
- 229920012128 methyl methacrylate acrylonitrile butadiene styrene Polymers 0.000 claims 1
- 239000000523 sample Substances 0.000 description 18
- 238000006116 polymerization reaction Methods 0.000 description 15
- 229920000642 polymer Polymers 0.000 description 14
- 239000000126 substance Substances 0.000 description 14
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 12
- 239000001993 wax Substances 0.000 description 10
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 9
- 238000004026 adhesive bonding Methods 0.000 description 9
- 229920001577 copolymer Polymers 0.000 description 8
- 229920002681 hypalon Polymers 0.000 description 8
- 239000003999 initiator Substances 0.000 description 8
- 229920001084 poly(chloroprene) Polymers 0.000 description 8
- 239000004971 Cross linker Substances 0.000 description 7
- 125000000524 functional group Chemical group 0.000 description 7
- 229920000647 polyepoxide Polymers 0.000 description 7
- 239000000758 substrate Substances 0.000 description 7
- DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 description 6
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 6
- 150000002118 epoxides Chemical class 0.000 description 6
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 6
- 229920003023 plastic Polymers 0.000 description 6
- 239000004033 plastic Substances 0.000 description 6
- IRLPACMLTUPBCL-KQYNXXCUSA-N 5'-adenylyl sulfate Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP(O)(=O)OS(O)(=O)=O)[C@@H](O)[C@H]1O IRLPACMLTUPBCL-KQYNXXCUSA-N 0.000 description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 5
- 239000000654 additive Substances 0.000 description 5
- 125000003700 epoxy group Chemical group 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 4
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 4
- 230000000996 additive effect Effects 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 4
- 230000000704 physical effect Effects 0.000 description 4
- 239000004014 plasticizer Substances 0.000 description 4
- 239000002952 polymeric resin Substances 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- 230000009257 reactivity Effects 0.000 description 4
- 229920003002 synthetic resin Polymers 0.000 description 4
- 150000004992 toluidines Chemical class 0.000 description 4
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 3
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 3
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 3
- 239000005977 Ethylene Substances 0.000 description 3
- 229920002633 Kraton (polymer) Polymers 0.000 description 3
- 229920009204 Methacrylate-butadiene-styrene Polymers 0.000 description 3
- 239000004698 Polyethylene Substances 0.000 description 3
- 229910000831 Steel Inorganic materials 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 239000011324 bead Substances 0.000 description 3
- QUZSUMLPWDHKCJ-UHFFFAOYSA-N bisphenol A dimethacrylate Chemical class C1=CC(OC(=O)C(=C)C)=CC=C1C(C)(C)C1=CC=C(OC(=O)C(C)=C)C=C1 QUZSUMLPWDHKCJ-UHFFFAOYSA-N 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 238000004132 cross linking Methods 0.000 description 3
- 239000003822 epoxy resin Substances 0.000 description 3
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 3
- 229920000058 polyacrylate Polymers 0.000 description 3
- 239000003381 stabilizer Substances 0.000 description 3
- 239000010959 steel Substances 0.000 description 3
- YNGDWRXWKFWCJY-UHFFFAOYSA-N 1,4-Dihydropyridine Chemical compound C1C=CNC=C1 YNGDWRXWKFWCJY-UHFFFAOYSA-N 0.000 description 2
- UWNADWZGEHDQAB-UHFFFAOYSA-N 2,5-dimethylhexane Chemical group CC(C)CCC(C)C UWNADWZGEHDQAB-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- KUDUQBURMYMBIJ-UHFFFAOYSA-N 2-prop-2-enoyloxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC(=O)C=C KUDUQBURMYMBIJ-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- 229920000459 Nitrile rubber Polymers 0.000 description 2
- 239000005062 Polybutadiene Substances 0.000 description 2
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 2
- 229920000800 acrylic rubber Polymers 0.000 description 2
- XECAHXYUAAWDEL-UHFFFAOYSA-N acrylonitrile butadiene styrene Chemical compound C=CC=C.C=CC#N.C=CC1=CC=CC=C1 XECAHXYUAAWDEL-UHFFFAOYSA-N 0.000 description 2
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 2
- 239000004676 acrylonitrile butadiene styrene Substances 0.000 description 2
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 230000001747 exhibiting effect Effects 0.000 description 2
- 229920001519 homopolymer Polymers 0.000 description 2
- 238000002372 labelling Methods 0.000 description 2
- 229920002857 polybutadiene Polymers 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 239000002685 polymerization catalyst Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 229920003048 styrene butadiene rubber Polymers 0.000 description 2
- 229920000468 styrene butadiene styrene block copolymer Polymers 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- DHZZPKMVVSTYLF-UHFFFAOYSA-N 2-(2-methylanilino)ethanol Chemical compound CC1=CC=CC=C1NCCO DHZZPKMVVSTYLF-UHFFFAOYSA-N 0.000 description 1
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 1
- 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 1
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 1
- MCPNDVSULWYVES-UHFFFAOYSA-N 2-ethyl-2-(hydroxymethyl)propane-1,3-diol 2-methylprop-2-enoic acid Chemical compound CC(=C)C(O)=O.CC(=C)C(O)=O.CC(=C)C(O)=O.CCC(CO)(CO)CO.CCC(CO)(CO)CO MCPNDVSULWYVES-UHFFFAOYSA-N 0.000 description 1
- WDQMWEYDKDCEHT-UHFFFAOYSA-N 2-ethylhexyl 2-methylprop-2-enoate Chemical compound CCCCC(CC)COC(=O)C(C)=C WDQMWEYDKDCEHT-UHFFFAOYSA-N 0.000 description 1
- VAJVDSVGBWFCLW-UHFFFAOYSA-N 3-Phenyl-1-propanol Chemical compound OCCCC1=CC=CC=C1 VAJVDSVGBWFCLW-UHFFFAOYSA-N 0.000 description 1
- XOJWAAUYNWGQAU-UHFFFAOYSA-N 4-(2-methylprop-2-enoyloxy)butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCCOC(=O)C(C)=C XOJWAAUYNWGQAU-UHFFFAOYSA-N 0.000 description 1
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 1
- ACYXOHNDKRVKLH-UHFFFAOYSA-N 5-phenylpenta-2,4-dienenitrile prop-2-enoic acid Chemical compound OC(=O)C=C.N#CC=CC=CC1=CC=CC=C1 ACYXOHNDKRVKLH-UHFFFAOYSA-N 0.000 description 1
- YXALYBMHAYZKAP-UHFFFAOYSA-N 7-oxabicyclo[4.1.0]heptan-4-ylmethyl 7-oxabicyclo[4.1.0]heptane-4-carboxylate Chemical compound C1CC2OC2CC1C(=O)OCC1CC2OC2CC1 YXALYBMHAYZKAP-UHFFFAOYSA-N 0.000 description 1
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 229920013646 Hycar Polymers 0.000 description 1
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 1
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 description 1
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical group OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- LCXXNKZQVOXMEH-UHFFFAOYSA-N Tetrahydrofurfuryl methacrylate Chemical compound CC(=C)C(=O)OCC1CCCO1 LCXXNKZQVOXMEH-UHFFFAOYSA-N 0.000 description 1
- OKKRPWIIYQTPQF-UHFFFAOYSA-N Trimethylolpropane trimethacrylate Chemical compound CC(=C)C(=O)OCC(CC)(COC(=O)C(C)=C)COC(=O)C(C)=C OKKRPWIIYQTPQF-UHFFFAOYSA-N 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- 229920006243 acrylic copolymer Polymers 0.000 description 1
- 229920006397 acrylic thermoplastic Polymers 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 125000005250 alkyl acrylate group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- ZPOLOEWJWXZUSP-WAYWQWQTSA-N bis(prop-2-enyl) (z)-but-2-enedioate Chemical compound C=CCOC(=O)\C=C/C(=O)OCC=C ZPOLOEWJWXZUSP-WAYWQWQTSA-N 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- VZIBAPMSKYQDFH-UHFFFAOYSA-N buta-1,3-diene;2-methylprop-2-enoic acid;prop-2-enenitrile;styrene Chemical compound C=CC=C.C=CC#N.CC(=C)C(O)=O.C=CC1=CC=CC=C1 VZIBAPMSKYQDFH-UHFFFAOYSA-N 0.000 description 1
- LKAVYBZHOYOUSX-UHFFFAOYSA-N buta-1,3-diene;2-methylprop-2-enoic acid;styrene Chemical compound C=CC=C.CC(=C)C(O)=O.C=CC1=CC=CC=C1 LKAVYBZHOYOUSX-UHFFFAOYSA-N 0.000 description 1
- BRXCDHOLJPJLLT-UHFFFAOYSA-N butane-2-sulfonic acid Chemical compound CCC(C)S(O)(=O)=O BRXCDHOLJPJLLT-UHFFFAOYSA-N 0.000 description 1
- 239000004568 cement Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000013626 chemical specie Substances 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 238000001246 colloidal dispersion Methods 0.000 description 1
- 239000013068 control sample Substances 0.000 description 1
- ZKXWKVVCCTZOLD-UHFFFAOYSA-N copper;4-hydroxypent-3-en-2-one Chemical compound [Cu].CC(O)=CC(C)=O.CC(O)=CC(C)=O ZKXWKVVCCTZOLD-UHFFFAOYSA-N 0.000 description 1
- VNZQQAVATKSIBR-UHFFFAOYSA-L copper;octanoate Chemical compound [Cu+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O VNZQQAVATKSIBR-UHFFFAOYSA-L 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- OIWOHHBRDFKZNC-UHFFFAOYSA-N cyclohexyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1CCCCC1 OIWOHHBRDFKZNC-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 125000004386 diacrylate group Chemical group 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000011953 free-radical catalyst Substances 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
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 1
- 238000009863 impact test Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- PKBRCANVDCVQJP-UHFFFAOYSA-L iron(2+);propanoate Chemical compound [Fe+2].CCC([O-])=O.CCC([O-])=O PKBRCANVDCVQJP-UHFFFAOYSA-L 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- JDEJGVSZUIJWBM-UHFFFAOYSA-N n,n,2-trimethylaniline Chemical compound CN(C)C1=CC=CC=C1C JDEJGVSZUIJWBM-UHFFFAOYSA-N 0.000 description 1
- YQYUUNRAPYPAPC-UHFFFAOYSA-N n,n-diethyl-2-methylaniline Chemical compound CCN(CC)C1=CC=CC=C1C YQYUUNRAPYPAPC-UHFFFAOYSA-N 0.000 description 1
- OMYXQGTUTCZGCI-UHFFFAOYSA-N n-(2-methylphenyl)hydroxylamine Chemical group CC1=CC=CC=C1NO OMYXQGTUTCZGCI-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- SCUZVMOVTVSBLE-UHFFFAOYSA-N prop-2-enenitrile;styrene Chemical compound C=CC#N.C=CC1=CC=CC=C1 SCUZVMOVTVSBLE-UHFFFAOYSA-N 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
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- KPBSJEBFALFJTO-UHFFFAOYSA-N propane-1-sulfonyl chloride Chemical compound CCCS(Cl)(=O)=O KPBSJEBFALFJTO-UHFFFAOYSA-N 0.000 description 1
- 238000007342 radical addition reaction Methods 0.000 description 1
- 238000000518 rheometry Methods 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 229920000638 styrene acrylonitrile Polymers 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 1
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 229910052720 vanadium 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
- 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
- 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
- C09J163/10—Epoxy resins modified by unsaturated 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
- 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
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2666/00—Composition of polymers characterized by a further compound in the blend, being organic macromolecular compounds, natural resins, waxes or and bituminous materials, non-macromolecular organic substances, inorganic substances or characterized by their function in the composition
- C08L2666/02—Organic macromolecular compounds, natural resins, waxes or and bituminous materials
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L51/00—Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers
- C08L51/04—Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers grafted on to rubbers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L55/00—Compositions of homopolymers or copolymers, obtained by polymerisation reactions only involving carbon-to-carbon unsaturated bonds, not provided for in groups C08L23/00 - C08L53/00
- C08L55/02—ABS [Acrylonitrile-Butadiene-Styrene] 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
- C09J2451/00—Presence of graft polymer
-
- 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
- C09J2455/00—Presence of ABS
-
- 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
- C09J2463/00—Presence of epoxy resin
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Adhesives Or Adhesive Processes (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/326,300 US6949602B2 (en) | 2002-12-19 | 2002-12-19 | Heat resistant, impact resistant, acrylic/epoxy adhesives |
| US10/326,300 | 2002-12-19 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2449590A1 CA2449590A1 (en) | 2004-06-19 |
| CA2449590C true CA2449590C (en) | 2010-01-19 |
Family
ID=32393119
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002449590A Expired - Lifetime CA2449590C (en) | 2002-12-19 | 2003-11-18 | Heat resistant, impact resistant, acrylic/epoxy adhesives |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US6949602B2 (enExample) |
| EP (1) | EP1431365B1 (enExample) |
| JP (1) | JP2004197102A (enExample) |
| CN (1) | CN1312247C (enExample) |
| CA (1) | CA2449590C (enExample) |
| DE (1) | DE60306875T2 (enExample) |
Families Citing this family (35)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7799383B2 (en) * | 2004-09-30 | 2010-09-21 | Illinois Tool Works, Inc. | Surface activated adhesive systems |
| US7348385B2 (en) * | 2005-03-09 | 2008-03-25 | Illinois Tool Works Inc. | Acrylate/methacrylate adhesives initiated by chlorosulfonated polymer |
| US20060293449A1 (en) * | 2005-06-23 | 2006-12-28 | Weberg Rolf T | Solid filler containing polymerizable compositions, articles formed thereby and methods of formation |
| US9272490B2 (en) * | 2005-09-23 | 2016-03-01 | Arkema France | Acrylic/thermoplastic olefin composite |
| JP5243965B2 (ja) * | 2005-12-15 | 2013-07-24 | ハンツマン アドバンスト マテリアルズ （スイッツァランド） ゲーエムベーハー | 多相アクリル系接着剤 |
| US20070155899A1 (en) * | 2005-12-21 | 2007-07-05 | Ips Corporation | Elastic methacrylate compositions |
| US20070155879A1 (en) * | 2005-12-22 | 2007-07-05 | Ips Corporation | Adhesive compositions for bonding metals |
| US7438782B2 (en) * | 2006-06-07 | 2008-10-21 | Zephyros, Inc. | Activatable material for sealing, baffling or reinforcing and method of forming same |
| WO2008087467A1 (en) | 2007-01-17 | 2008-07-24 | Hexcel Composites, Ltd. | Low temperature curing of toughened epoxy adhesives |
| KR20100015635A (ko) * | 2007-04-05 | 2010-02-12 | 자크레 | 구조용 접착제 조성물 |
| FR2914651B1 (fr) * | 2007-04-05 | 2012-08-31 | Jacret | Composition pour adhesif structural |
| CN104263291A (zh) * | 2007-08-08 | 2015-01-07 | 日立化成工业株式会社 | 粘接剂组合物、膜状粘接剂和电路部件的连接结构 |
| CA2703907C (en) * | 2007-10-30 | 2016-11-01 | Henkel Ag & Co. Kgaa | Epoxy paste adhesives resistant to wash-off |
| DE102008004112A1 (de) * | 2008-01-11 | 2009-07-16 | Saertex Gmbh & Co. Kg | Textiles Halbzeug mit wenigstens einer mit einem Kleber versehenen Oberfläche |
| JP5304019B2 (ja) * | 2008-05-14 | 2013-10-02 | 日立化成株式会社 | 回路接続材料 |
| WO2010007148A2 (de) * | 2008-07-17 | 2010-01-21 | Sika Technology Ag | Epoxid/(meth)acrylat zusammensetzung |
| EP2189500A1 (de) | 2008-11-21 | 2010-05-26 | Sika Technology AG | Epoxid/(Meth)acrylat Zusammensetzung |
| US20100113674A1 (en) * | 2008-10-31 | 2010-05-06 | Strand Richard M | Methacrylate adhesive |
| TWI595037B (zh) | 2009-04-30 | 2017-08-11 | 電化股份有限公司 | 硬化性樹脂組成物、接著劑組成物、硬化體或複合體 |
| ES2391720T3 (es) * | 2010-02-11 | 2012-11-29 | Hilti Aktiengesellschaft | Mortero de resina adecuado para fines de construcción, especialmente para anclaje químico |
| RU2439111C2 (ru) * | 2010-04-05 | 2012-01-10 | Государственное образовательное учреждение высшего профессионального образования "Владимирский государственный университет" | Адгезионный состав для бетонных поверхностей |
| KR101471323B1 (ko) * | 2011-04-05 | 2014-12-09 | 헨켈 아이피 앤드 홀딩 게엠베하 | B-스테이지 가능한 스킵-경화성 웨이퍼 후면 코팅 접착제 |
| DE102012219479B4 (de) * | 2012-10-24 | 2016-12-15 | Hilti Aktiengesellschaft | Reaktionsharz-Zusammensetzung und deren Verwendung |
| WO2015084553A1 (en) * | 2013-12-05 | 2015-06-11 | Dow Global Technologies Llc | Acrylic adhesive compositions, manufacture and use thereof |
| US9676922B2 (en) * | 2014-06-11 | 2017-06-13 | IPS, Corporation—Weld-On Division | Heat and moisture resistant acrylic adhesive composition |
| US10487969B2 (en) | 2014-09-26 | 2019-11-26 | Ips, Corporation-Weld-On Division | Pipe fitting apparatus and methods |
| CN105038676A (zh) * | 2015-08-03 | 2015-11-11 | 芜湖真空科技有限公司 | Low-e玻璃用密封胶材料组合物和密封胶的制备方法 |
| US10392532B2 (en) * | 2015-10-07 | 2019-08-27 | Illinois Tool Works, Inc. | Adhesive compositions with repair-rework ability |
| EP3596182B1 (en) | 2017-03-17 | 2021-06-30 | Dow Global Technologies LLC | Epoxy-acrylic hybrid adhesive |
| CN107418475A (zh) * | 2017-09-21 | 2017-12-01 | 南通如港船舶配套机械有限公司 | 一种船舶用金属板粘接剂 |
| KR102853200B1 (ko) * | 2019-06-25 | 2025-08-29 | 주식회사 두산 | 접착 조성물 및 이를 포함하는 커버레이 필름 및 인쇄회로기판 |
| EP4119594A1 (de) | 2021-07-16 | 2023-01-18 | Hilti Aktiengesellschaft | Acrylathaltige bindemittel für befestigungszwecke |
| EP4119589A1 (en) | 2021-07-16 | 2023-01-18 | Hilti Aktiengesellschaft | Epoxy resin mixtures comprising epoxide-acrylate hybrid molecules and multicomponent reactive resin compositions therefrom |
| EP4119590A1 (en) | 2021-07-16 | 2023-01-18 | Hilti Aktiengesellschaft | Epoxide-acrylate hybrid molecules and their use for chemical anchoring |
| US12422064B2 (en) | 2022-10-27 | 2025-09-23 | IPS, Corporation—Weld-On Division | Pipe fittings and assemblies |
Family Cites Families (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3890407A (en) | 1972-07-20 | 1975-06-17 | Du Pont | Novel adhesive compositions |
| US4106971A (en) | 1975-02-21 | 1978-08-15 | E. I. Du Pont De Nemours And Company | Method of adhesive bonding |
| US4182644A (en) | 1975-03-27 | 1980-01-08 | E. I. Du Pont De Nemours And Company | Polymer in monomer adhesive composition and method employing same |
| US4113792A (en) | 1977-06-20 | 1978-09-12 | National Starch And Chemical Corporation | Pressure sensitive adhesive compositions |
| DE2965140D1 (en) * | 1978-08-16 | 1983-05-11 | Ciba Geigy Ag | Adhesives or adhesive constituents and their use for bonding two surfaces |
| JPS5674165A (en) * | 1979-11-20 | 1981-06-19 | Nogawa Chem Kk | Two-pack nonmixing type acrylic adhesive composition |
| US4426243A (en) | 1981-12-01 | 1984-01-17 | Illinois Tool Works Inc. | Room-temperature-curable, quick-setting acrylic/epoxy adhesives and methods of bonding |
| US4536546A (en) | 1983-09-22 | 1985-08-20 | Illinois Tool Works Inc. | (Meth)acrylate-based compositions |
| US4773957A (en) | 1983-09-22 | 1988-09-27 | Illinois Tool Works, Inc. | Bonding method employing novel methacrylate based adhesive compositions |
| US4612209A (en) | 1983-12-27 | 1986-09-16 | Ciba-Geigy Corporation | Process for the preparation of heat-curable adhesive films |
| JPS6151072A (ja) * | 1984-08-17 | 1986-03-13 | Nogawa Chem Kk | 二液非混合型アクリル系接着剤組成物 |
| GB8521845D0 (en) * | 1985-09-03 | 1985-10-09 | Permabond Adhesives | Initiator compositions |
| GB8522042D0 (en) | 1985-09-05 | 1985-10-09 | Permabond Adhesives | Acrylic adhesives & sealants |
| US4695508A (en) | 1985-09-06 | 1987-09-22 | The Yokohama Rubber Co., Ltd. | Adhesive composition |
| US4959405A (en) * | 1986-06-04 | 1990-09-25 | Illinois Tool Works, Inc. | Acid modified adhesive composition |
| US4714730A (en) | 1986-06-04 | 1987-12-22 | Illinois Tool Works Inc. | Acid modified adhesive compositions |
| US5112691A (en) | 1988-08-29 | 1992-05-12 | Illinois Tool Works, Inc. | Adhesive for low temperature applications |
| US4942201A (en) * | 1988-08-29 | 1990-07-17 | Illinois Tool Works, Inc. | Adhesive for low temperature applications |
| JP2676540B2 (ja) * | 1988-12-23 | 1997-11-17 | ノガワケミカル株式会社 | 二液非混合型アクリル系接着剤組成物 |
| EP0833874A1 (en) | 1995-06-21 | 1998-04-08 | Minnesota Mining And Manufacturing Company | Adhesive compositions, bonding films made therefrom and processes for making bonding films |
| US6660805B1 (en) * | 2002-05-16 | 2003-12-09 | Lord Corporation | Two-part adhesive: part A-monomer, toughener(s), optional adhesion promotor and reducing agent; part B-epoxy resin |
| EP2818365A1 (en) * | 2013-06-24 | 2014-12-31 | Behr France Rouffach SAS | Electric module and motor vehicle with an electric module |
-
2002
- 2002-12-19 US US10/326,300 patent/US6949602B2/en not_active Expired - Lifetime
-
2003
- 2003-11-06 DE DE60306875T patent/DE60306875T2/de not_active Revoked
- 2003-11-06 EP EP03025467A patent/EP1431365B1/en not_active Revoked
- 2003-11-18 CA CA002449590A patent/CA2449590C/en not_active Expired - Lifetime
- 2003-12-18 JP JP2003421328A patent/JP2004197102A/ja active Pending
- 2003-12-18 CN CNB2003101232224A patent/CN1312247C/zh not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| CA2449590A1 (en) | 2004-06-19 |
| CN1629243A (zh) | 2005-06-22 |
| EP1431365B1 (en) | 2006-07-19 |
| EP1431365A1 (en) | 2004-06-23 |
| US6949602B2 (en) | 2005-09-27 |
| CN1312247C (zh) | 2007-04-25 |
| DE60306875D1 (de) | 2006-08-31 |
| US20040118514A1 (en) | 2004-06-24 |
| DE60306875T2 (de) | 2007-09-06 |
| JP2004197102A (ja) | 2004-07-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKEX | Expiry |
Effective date: 20231120 |