CA2462454C - High temperature epoxy adhesive films - Google Patents
High temperature epoxy adhesive films Download PDFInfo
- Publication number
- CA2462454C CA2462454C CA002462454A CA2462454A CA2462454C CA 2462454 C CA2462454 C CA 2462454C CA 002462454 A CA002462454 A CA 002462454A CA 2462454 A CA2462454 A CA 2462454A CA 2462454 C CA2462454 C CA 2462454C
- Authority
- CA
- Canada
- Prior art keywords
- adhesive composition
- polyepoxide
- weight percent
- resin
- cycloaliphatic
- 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 - Fee Related
Links
- 239000002313 adhesive film Substances 0.000 title description 15
- 229920006332 epoxy adhesive Polymers 0.000 title description 2
- 229920000647 polyepoxide Polymers 0.000 claims abstract description 102
- 229920005989 resin Polymers 0.000 claims abstract description 84
- 239000011347 resin Substances 0.000 claims abstract description 84
- 239000000853 adhesive Substances 0.000 claims abstract description 60
- 230000001070 adhesive effect Effects 0.000 claims abstract description 60
- 125000003118 aryl group Chemical group 0.000 claims abstract description 38
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims abstract 4
- 239000000203 mixture Substances 0.000 claims description 85
- 150000002118 epoxides Chemical class 0.000 claims description 24
- -1 amino hydrogen Chemical class 0.000 claims description 22
- 239000003822 epoxy resin Substances 0.000 claims description 20
- 239000012745 toughening agent Substances 0.000 claims description 18
- 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 16
- 239000004593 Epoxy Substances 0.000 claims description 9
- 150000001412 amines Chemical class 0.000 claims description 9
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 claims description 9
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 8
- 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
- 229940106691 bisphenol a Drugs 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 229920003986 novolac Polymers 0.000 claims description 6
- YRKVLGUIGNRYJX-UHFFFAOYSA-N 4-[9-(4-amino-3-methylphenyl)fluoren-9-yl]-2-methylaniline Chemical compound C1=C(N)C(C)=CC(C2(C3=CC=CC=C3C3=CC=CC=C32)C=2C=C(C)C(N)=CC=2)=C1 YRKVLGUIGNRYJX-UHFFFAOYSA-N 0.000 claims description 5
- SLGWESQGEUXWJQ-UHFFFAOYSA-N formaldehyde;phenol Chemical compound O=C.OC1=CC=CC=C1 SLGWESQGEUXWJQ-UHFFFAOYSA-N 0.000 claims description 5
- 229920001568 phenolic resin Polymers 0.000 claims description 5
- 229920000459 Nitrile rubber Polymers 0.000 claims description 4
- 229920002857 polybutadiene Polymers 0.000 claims description 4
- UUODQIKUTGWMPT-UHFFFAOYSA-N 2-fluoro-5-(trifluoromethyl)pyridine Chemical compound FC1=CC=C(C(F)(F)F)C=N1 UUODQIKUTGWMPT-UHFFFAOYSA-N 0.000 claims description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 3
- 239000011258 core-shell material Substances 0.000 claims description 3
- 229920000570 polyether Polymers 0.000 claims description 3
- 229920003987 resole Polymers 0.000 claims description 3
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical class NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 claims description 2
- IXCOKTMGCRJMDR-UHFFFAOYSA-N 9h-fluorene;phenol Chemical compound OC1=CC=CC=C1.OC1=CC=CC=C1.C1=CC=C2CC3=CC=CC=C3C2=C1 IXCOKTMGCRJMDR-UHFFFAOYSA-N 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 12
- 239000004721 Polyphenylene oxide Substances 0.000 claims 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 2
- 150000002220 fluorenes Chemical class 0.000 claims 1
- 229920001971 elastomer Polymers 0.000 description 10
- 239000011521 glass Substances 0.000 description 10
- 239000005060 rubber Substances 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- 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 7
- 239000000126 substance Substances 0.000 description 7
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 6
- 229910052782 aluminium Inorganic materials 0.000 description 6
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 5
- 238000007667 floating Methods 0.000 description 5
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 4
- 150000002170 ethers Chemical class 0.000 description 4
- 230000009477 glass transition Effects 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- 239000004744 fabric Substances 0.000 description 3
- 239000000945 filler Substances 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 239000008399 tap water Substances 0.000 description 3
- 235000020679 tap water Nutrition 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 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 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000002671 adjuvant Substances 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 125000003700 epoxy group Chemical group 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000003063 flame retardant Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 125000003367 polycyclic group Chemical group 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellitic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 229920001187 thermosetting polymer Polymers 0.000 description 2
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 2
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 2
- QDMXRSFKPPVBDW-UHFFFAOYSA-N 2-[9-(2-aminophenyl)fluoren-9-yl]aniline Chemical compound NC1=CC=CC=C1C1(C=2C(=CC=CC=2)N)C2=CC=CC=C2C2=CC=CC=C21 QDMXRSFKPPVBDW-UHFFFAOYSA-N 0.000 description 1
- JHWIEAWILPSRMU-UHFFFAOYSA-N 2-methyl-3-pyrimidin-4-ylpropanoic acid Chemical compound OC(=O)C(C)CC1=CC=NC=N1 JHWIEAWILPSRMU-UHFFFAOYSA-N 0.000 description 1
- CIZUMWWHWPJAAK-UHFFFAOYSA-N 4-[9-(4-amino-3-chlorophenyl)fluoren-9-yl]-2-chloroaniline Chemical compound C1=C(Cl)C(N)=CC=C1C1(C=2C=C(Cl)C(N)=CC=2)C2=CC=CC=C2C2=CC=CC=C21 CIZUMWWHWPJAAK-UHFFFAOYSA-N 0.000 description 1
- IZSHZLKNFQAAKX-UHFFFAOYSA-N 5-cyclopenta-2,4-dien-1-ylcyclopenta-1,3-diene Chemical group C1=CC=CC1C1C=CC=C1 IZSHZLKNFQAAKX-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
- CYSPWCARDHRYJX-UHFFFAOYSA-N 9h-fluoren-1-amine Chemical compound C12=CC=CC=C2CC2=C1C=CC=C2N CYSPWCARDHRYJX-UHFFFAOYSA-N 0.000 description 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical class NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
- 229930185605 Bisphenol Natural products 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- 241000157426 Pernis Species 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 238000007605 air drying Methods 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000011324 bead Substances 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
- JRPRCOLKIYRSNH-UHFFFAOYSA-N bis(oxiran-2-ylmethyl) benzene-1,2-dicarboxylate Chemical compound C=1C=CC=C(C(=O)OCC2OC2)C=1C(=O)OCC1CO1 JRPRCOLKIYRSNH-UHFFFAOYSA-N 0.000 description 1
- ZXOATMQSUNJNNG-UHFFFAOYSA-N bis(oxiran-2-ylmethyl) benzene-1,3-dicarboxylate Chemical compound C=1C=CC(C(=O)OCC2OC2)=CC=1C(=O)OCC1CO1 ZXOATMQSUNJNNG-UHFFFAOYSA-N 0.000 description 1
- 230000003750 conditioning effect Effects 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 239000011353 cycloaliphatic epoxy resin Substances 0.000 description 1
- 239000013527 degreasing agent Substances 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical class C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 239000011152 fibreglass Substances 0.000 description 1
- 229910021485 fumed silica Inorganic materials 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000012784 inorganic fiber Substances 0.000 description 1
- 229920000126 latex Polymers 0.000 description 1
- 239000004816 latex Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000005065 mining Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- OHQOKJPHNPUMLN-UHFFFAOYSA-N n,n'-diphenylmethanediamine Chemical class C=1C=CC=CC=1NCNC1=CC=CC=C1 OHQOKJPHNPUMLN-UHFFFAOYSA-N 0.000 description 1
- 238000000643 oven drying Methods 0.000 description 1
- 238000007719 peel strength test Methods 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 239000004848 polyfunctional curative Substances 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 239000011342 resin composition Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical compound [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000004447 silicone coating Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 239000005061 synthetic rubber Substances 0.000 description 1
- 238000009864 tensile test Methods 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 239000004634 thermosetting polymer Substances 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/17—Amines; Quaternary ammonium compounds
- C08K5/18—Amines; Quaternary ammonium compounds with aromatically bound amino groups
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)
- Adhesive Tapes (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/005,556 US6624213B2 (en) | 2001-11-08 | 2001-11-08 | High temperature epoxy adhesive films |
| US10/005,556 | 2001-11-08 | ||
| PCT/US2002/030155 WO2003040251A1 (en) | 2001-11-08 | 2002-09-23 | High temperature epoxy adhesive films |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2462454A1 CA2462454A1 (en) | 2003-05-15 |
| CA2462454C true CA2462454C (en) | 2009-11-24 |
Family
ID=21716455
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002462454A Expired - Fee Related CA2462454C (en) | 2001-11-08 | 2002-09-23 | High temperature epoxy adhesive films |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US6624213B2 (enExample) |
| EP (1) | EP1442090B1 (enExample) |
| JP (1) | JP4242771B2 (enExample) |
| CN (1) | CN1256396C (enExample) |
| AT (1) | ATE437932T1 (enExample) |
| BR (1) | BR0213751B1 (enExample) |
| CA (1) | CA2462454C (enExample) |
| DE (1) | DE60233153D1 (enExample) |
| ES (1) | ES2330926T3 (enExample) |
| WO (1) | WO2003040251A1 (enExample) |
Families Citing this family (45)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7473715B2 (en) | 2001-05-02 | 2009-01-06 | Zephyros, Inc. | Two component (epoxy/amine) structural foam-in-place material |
| US7125461B2 (en) | 2003-05-07 | 2006-10-24 | L & L Products, Inc. | Activatable material for sealing, baffling or reinforcing and method of forming same |
| US20060261312A1 (en) * | 2003-05-28 | 2006-11-23 | Lonza Inc. | Quaternary ammonium salts containing non-halogen anions as anticorrosive agents |
| US20060240198A1 (en) * | 2003-06-04 | 2006-10-26 | Sekisui Chemical Co., Ltd. | Curing resin composition, sealing material for liquid crystal display device and liquid crystal display device |
| KR100935774B1 (ko) * | 2003-06-04 | 2010-01-06 | 세키스이가가쿠 고교가부시키가이샤 | 경화성 수지 조성물, 액정 표시 소자용 시일제 및 액정표시 소자 |
| US7199165B2 (en) | 2003-06-26 | 2007-04-03 | L & L Products, Inc. | Expandable material |
| US8070994B2 (en) | 2004-06-18 | 2011-12-06 | Zephyros, Inc. | Panel structure |
| US7521093B2 (en) | 2004-07-21 | 2009-04-21 | Zephyros, Inc. | Method of sealing an interface |
| US20060182949A1 (en) | 2005-02-17 | 2006-08-17 | 3M Innovative Properties Company | Surfacing and/or joining method |
| US7405246B2 (en) * | 2005-04-05 | 2008-07-29 | Momentive Performance Materials Inc. | Cure system, adhesive system, electronic device |
| US7446136B2 (en) * | 2005-04-05 | 2008-11-04 | Momentive Performance Materials Inc. | Method for producing cure system, adhesive system, and electronic device |
| WO2007025007A1 (en) * | 2005-08-24 | 2007-03-01 | Henkel Kommanditgesellschaft Auf Aktien | Epoxy compositions having improved impact resistance |
| PL2049611T3 (pl) | 2006-07-31 | 2019-04-30 | Henkel Ag & Co Kgaa | Utwardzalne kompozycje klejowe oparte na żywicach epoksydowych |
| CN101547990B (zh) * | 2006-10-06 | 2012-09-05 | 汉高股份及两合公司 | 可泵送的耐洗掉的环氧膏状粘合剂 |
| WO2008130433A2 (en) * | 2006-10-12 | 2008-10-30 | C-3 International, Llc | Methods for providing prophylactic surface treatment for fluid processing systems and components thereof |
| US20080199642A1 (en) * | 2007-02-16 | 2008-08-21 | James Barlow | Molded Composite Slip Adapted for Engagement With an Internal Surface of a Metal Tubular |
| US20090011247A1 (en) | 2007-07-02 | 2009-01-08 | Oil States Industries, Inc. | Molded Composite Mandrel for a Downhole Zonal Isolation Tool |
| GB0717867D0 (en) * | 2007-09-14 | 2007-10-24 | 3M Innovative Properties Co | Flexible epoxy-based compositions |
| JP2009096851A (ja) * | 2007-10-15 | 2009-05-07 | Three M Innovative Properties Co | 非導電性接着剤組成物及び非導電性接着フィルム、並びにそれらの製造方法及び使用方法 |
| WO2009055403A2 (en) * | 2007-10-26 | 2009-04-30 | 3M Innovative Properties Company | Aqueous binder or sizing composition |
| MX2010004855A (es) * | 2007-10-30 | 2010-06-30 | Henkel Ag & Co Kgaa | Adhesivos de pasta epoxi resistentes al lavado. |
| GB0806434D0 (en) | 2008-04-09 | 2008-05-14 | Zephyros Inc | Improvements in or relating to structural adhesives |
| US8623301B1 (en) | 2008-04-09 | 2014-01-07 | C3 International, Llc | Solid oxide fuel cells, electrolyzers, and sensors, and methods of making and using the same |
| US20100192321A1 (en) * | 2009-01-30 | 2010-08-05 | 3M Innovative Properties Company | Hair and lint cleaning tool |
| EP2475730B1 (en) | 2009-09-11 | 2014-10-08 | 3M Innovative Properties Company | Curable and cured adhesive compositions |
| GB0916205D0 (en) | 2009-09-15 | 2009-10-28 | Zephyros Inc | Improvements in or relating to cavity filling |
| EP2534723A4 (en) | 2010-02-10 | 2015-08-05 | Fcet Inc | LOW TEMPERATURE ELECTROLYTE FOR SOLID FUEL CELLS WITH HIGH ION CONDUCTIVITY |
| EP2542403B2 (en) | 2010-03-04 | 2023-08-16 | Zephyros Inc. | Structural composite laminate |
| WO2012088693A1 (en) * | 2010-12-30 | 2012-07-05 | Dow Global Technologies Llc | Exterior thermal insulation system |
| US8840750B2 (en) | 2012-02-29 | 2014-09-23 | United Technologies Corporation | Method of bonding a leading edge sheath to a blade body of a fan blade |
| US20140299268A1 (en) * | 2013-04-09 | 2014-10-09 | The Boeing Company | Thermally Curable Bonding Film Adhesive with Uniform Thickness |
| US9905871B2 (en) | 2013-07-15 | 2018-02-27 | Fcet, Inc. | Low temperature solid oxide cells |
| CN105722933A (zh) | 2013-07-26 | 2016-06-29 | 泽费罗斯股份有限公司 | 热固性粘合膜的改进或涉及它的改进 |
| US10087707B2 (en) | 2013-09-12 | 2018-10-02 | Weatherford Technology Holdings, Llc | Molded composite slip of sheet molded compound for downhole tool |
| GB201417985D0 (en) | 2014-10-10 | 2014-11-26 | Zephyros Inc | Improvements in or relating to structural adhesives |
| CN104388028A (zh) * | 2014-12-01 | 2015-03-04 | 南京大学 | 一种韧性耐高温环氧树脂粘合剂 |
| TWI600674B (zh) * | 2016-04-15 | 2017-10-01 | 南亞塑膠工業股份有限公司 | 二環戊二烯－酚樹脂與２，６二甲基苯酚共聚物環氧樹脂製造與應用 |
| US11485881B2 (en) | 2017-12-15 | 2022-11-01 | 3M Innovative Properties Company | High temperature structural adhesive films |
| US11370908B2 (en) | 2018-06-27 | 2022-06-28 | 3M Innovative Properties Company | Curable compositions and related methods |
| CN112969737B (zh) * | 2018-10-31 | 2024-10-01 | 3M创新有限公司 | 可固化粘合剂、粘结膜及其粘结方法 |
| KR20230037556A (ko) | 2020-07-13 | 2023-03-16 | 헨켈 아게 운트 코. 카게아아 | 구리 결합용 전도성 에폭시 수지 조성물 |
| CN112063344A (zh) * | 2020-08-07 | 2020-12-11 | 江苏东邦科技有限公司 | 用于汽车内装的高韧性低挥发接着剂及接着剂膜 |
| EP4267647A1 (en) * | 2020-12-24 | 2023-11-01 | Sika Technology AG | One-component thermosetting epoxy adhesive with improved adhesion at high temperatures |
| KR20240155849A (ko) * | 2022-03-03 | 2024-10-29 | 헨켈 아게 운트 코. 카게아아 | 비경화 및 경화 시의 습윤 노출에 저항성이 있는 에폭시 구조용 접착제 |
| WO2025240636A1 (en) * | 2024-05-15 | 2025-11-20 | Cytec Industries Inc. | Adhesive composition for improved bonding performance |
Family Cites Families (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL92155C (enExample) | 1956-05-17 | |||
| US3449280A (en) | 1960-04-27 | 1969-06-10 | Minnesota Mining & Mfg | Adhesive composition containing high molecular weight polyamides,epoxy resins and curing agents |
| US3298998A (en) | 1961-03-07 | 1967-01-17 | Eastman Kodak Co | Bisglycidyl ethers of bisphenols |
| US3316195A (en) | 1961-11-13 | 1967-04-25 | Raybestos Manhattan Inc | Curable binder composition comprising epoxy resin, curing agent, and polymeric latex |
| US3332908A (en) | 1965-02-08 | 1967-07-25 | Union Carbide Corp | Glycidyl ethers |
| US3894112A (en) | 1969-10-31 | 1975-07-08 | Minnesota Mining & Mfg | Bonding film containing polytetramethyleneoxide elastomeric segments and polyepoxide |
| US3833683A (en) | 1970-12-21 | 1974-09-03 | Ford Motor Co | Rubber-modified thermosets and process i |
| US3707583A (en) | 1971-06-04 | 1972-12-26 | Minnesota Mining & Mfg | Adhesive |
| BE793030A (fr) | 1971-12-20 | 1973-04-16 | Goodrich Co B F | Procede pour la realisation de matieres plastiques de resine epoxy |
| US3864426A (en) | 1973-05-23 | 1975-02-04 | Union Carbide Corp | Thermal shock resistant epoxy compositions |
| US3856883A (en) | 1973-05-29 | 1974-12-24 | Ford Motor Co | Graded rubber particles having hydroxy functionality and a polymeric crosslinking agent |
| US4331582A (en) | 1980-01-14 | 1982-05-25 | Hitco | Epoxy latent catalyst |
| US4521490A (en) | 1983-08-11 | 1985-06-04 | Minnesota Mining And Manufacturing Co. | Two-part epoxy composition |
| US4704331A (en) | 1984-07-18 | 1987-11-03 | Minnesota Mining And Manufacturing Company | Method for adhering surfaces using fast curing epoxy resin compositions |
| US4684678A (en) | 1985-05-30 | 1987-08-04 | Minnesota Mining And Manufacturing Company | Epoxy resin curing agent, process, and composition |
| CA1264476A (en) * | 1985-05-30 | 1990-01-16 | William J. Schultz | Epoxy resin curing agent, process, and composition |
| US4904360A (en) | 1986-09-12 | 1990-02-27 | Minnesota Mining And Manufacturing Company | Water-compatible coating composition |
| US4980234A (en) | 1987-12-23 | 1990-12-25 | Minnesota Mining And Manufacturing Co. | Epoxide resin compositions and method |
| JP2643706B2 (ja) * | 1991-11-26 | 1997-08-20 | 信越化学工業株式会社 | 熱硬化性樹脂組成物及び半導体装置 |
| JPH07165880A (ja) | 1993-12-14 | 1995-06-27 | Matsushita Electric Works Ltd | 封止用エポキシ樹脂組成物 |
| JP3821870B2 (ja) | 1994-10-07 | 2006-09-13 | スリーエム カンパニー | 難燃性熱硬化性樹脂組成物 |
| JPH08291278A (ja) | 1995-04-21 | 1996-11-05 | Minnesota Mining & Mfg Co <3M> | ホットメルト接着剤組成物及び接着性フィルム |
| JPH098178A (ja) | 1995-06-14 | 1997-01-10 | Matsushita Electric Works Ltd | 封止用エポキシ樹脂組成物及びそれを用いた半導体装置 |
| US6180696B1 (en) | 1997-02-19 | 2001-01-30 | Georgia Tech Research Corporation | No-flow underfill of epoxy resin, anhydride, fluxing agent and surfactant |
| US6294270B1 (en) | 1998-12-23 | 2001-09-25 | 3M Innovative Properties Company | Electronic circuit device comprising an epoxy-modified aromatic vinyl-conjugated diene block copolymer |
| JP2001064483A (ja) * | 1999-08-27 | 2001-03-13 | Sumitomo Bakelite Co Ltd | 液晶表示素子用シール材組成物 |
| US6379799B1 (en) | 2000-06-29 | 2002-04-30 | Cytec Technology Corp. | Low moisture absorption epoxy resin systems with alkylated diamine hardeners |
-
2001
- 2001-11-08 US US10/005,556 patent/US6624213B2/en not_active Expired - Lifetime
-
2002
- 2002-09-23 CN CN02822191.5A patent/CN1256396C/zh not_active Expired - Fee Related
- 2002-09-23 AT AT02778311T patent/ATE437932T1/de not_active IP Right Cessation
- 2002-09-23 EP EP02778311A patent/EP1442090B1/en not_active Expired - Lifetime
- 2002-09-23 DE DE60233153T patent/DE60233153D1/de not_active Expired - Lifetime
- 2002-09-23 ES ES02778311T patent/ES2330926T3/es not_active Expired - Lifetime
- 2002-09-23 BR BRPI0213751-8A patent/BR0213751B1/pt not_active IP Right Cessation
- 2002-09-23 JP JP2003542292A patent/JP4242771B2/ja not_active Expired - Fee Related
- 2002-09-23 WO PCT/US2002/030155 patent/WO2003040251A1/en not_active Ceased
- 2002-09-23 CA CA002462454A patent/CA2462454C/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| BR0213751B1 (pt) | 2012-09-04 |
| CN1256396C (zh) | 2006-05-17 |
| ATE437932T1 (de) | 2009-08-15 |
| EP1442090A1 (en) | 2004-08-04 |
| WO2003040251A1 (en) | 2003-05-15 |
| US20030125423A1 (en) | 2003-07-03 |
| EP1442090B1 (en) | 2009-07-29 |
| US6624213B2 (en) | 2003-09-23 |
| DE60233153D1 (de) | 2009-09-10 |
| CN1582320A (zh) | 2005-02-16 |
| BR0213751A (pt) | 2004-10-19 |
| JP2005508436A (ja) | 2005-03-31 |
| JP4242771B2 (ja) | 2009-03-25 |
| ES2330926T3 (es) | 2009-12-17 |
| CA2462454A1 (en) | 2003-05-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA2462454C (en) | High temperature epoxy adhesive films | |
| JP3487083B2 (ja) | 熱硬化性樹脂組成物及びその硬化物 | |
| US4983672A (en) | Epoxide resin compositions and method | |
| TWI641648B (zh) | 苯并、環氧化合物及酸酐之混合物 | |
| KR101882642B1 (ko) | 강화 경화제를 포함하는 이액형 접착제 | |
| US11370908B2 (en) | Curable compositions and related methods | |
| JP2016507622A (ja) | 破壊靭性が高い硬化可能な組成物 | |
| JP2709731B2 (ja) | 芳香族ジアミン硬化剤からなるエポキシ樹脂 | |
| JPH0575775B2 (enExample) | ||
| JPH05202348A (ja) | クレオソート耐性エポキシ接着剤系 | |
| CA1337088C (en) | Curable epoxy resin mixture | |
| KR100528700B1 (ko) | 핫멜트 접착용 에폭시 프라이머 조성물 및 이를 이용한대상체 | |
| KR20250035345A (ko) | 카다놀 다이아민계 경화제를 포함하는 에폭시 수지 조성물 | |
| US5045363A (en) | Epoxide resin compositions and method | |
| JPS61143420A (ja) | 樹脂組成物 | |
| JPS61143419A (ja) | 樹脂組成物 | |
| JP4622781B2 (ja) | 新規化合物およびこれを用いた熱硬化性樹脂組成物 | |
| JP6389886B2 (ja) | 樹脂組成物及び電機機器 | |
| JPS63159424A (ja) | エポキシ樹脂組成物 | |
| JPH07309930A (ja) | エポキシ樹脂組成物 | |
| JP2003206390A (ja) | 熱硬化性樹脂組成物及びその硬化物 | |
| JPS61143421A (ja) | 樹脂組成物 | |
| JPS60260669A (ja) | 接着剤組成物 | |
| JPH05295341A (ja) | エポキシ樹脂接着剤 | |
| JPH032370B2 (enExample) |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20200923 |