KR20160025567A - 시밍 응용을 위한 고모듈러스 에폭시 접착제 - Google Patents
시밍 응용을 위한 고모듈러스 에폭시 접착제 Download PDFInfo
- Publication number
- KR20160025567A KR20160025567A KR1020167001817A KR20167001817A KR20160025567A KR 20160025567 A KR20160025567 A KR 20160025567A KR 1020167001817 A KR1020167001817 A KR 1020167001817A KR 20167001817 A KR20167001817 A KR 20167001817A KR 20160025567 A KR20160025567 A KR 20160025567A
- Authority
- KR
- South Korea
- Prior art keywords
- composition
- curing agent
- primary amino
- epoxy
- epoxy resin
- 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.)
- Withdrawn
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- 229920006332 epoxy adhesive Polymers 0.000 title 1
- 239000000203 mixture Substances 0.000 claims abstract description 155
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 98
- 239000003822 epoxy resin Substances 0.000 claims abstract description 70
- 229920000647 polyepoxide Polymers 0.000 claims abstract description 70
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 40
- 239000004593 Epoxy Substances 0.000 claims abstract description 37
- 239000004721 Polyphenylene oxide Substances 0.000 claims abstract description 30
- 229920000570 polyether Polymers 0.000 claims abstract description 30
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 19
- 125000004103 aminoalkyl group Chemical group 0.000 claims abstract description 15
- 229920000768 polyamine Polymers 0.000 claims abstract description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 11
- 238000011049 filling Methods 0.000 claims abstract description 9
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 claims description 33
- 150000001412 amines Chemical class 0.000 claims description 21
- 125000003118 aryl group Chemical group 0.000 claims description 17
- 239000000835 fiber Substances 0.000 claims description 15
- 125000005250 alkyl acrylate group Chemical group 0.000 claims description 14
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 239000000047 product Substances 0.000 claims description 10
- 229920005989 resin Polymers 0.000 claims description 10
- 239000011347 resin Substances 0.000 claims description 10
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- 238000000034 method Methods 0.000 claims description 9
- 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 7
- 229910052751 metal Inorganic materials 0.000 claims description 6
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- 125000001931 aliphatic group Chemical group 0.000 claims description 5
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- 239000011162 core material Substances 0.000 description 15
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
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- 239000000049 pigment 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
- 239000012745 toughening agent Substances 0.000 description 4
- KUBDPQJOLOUJRM-UHFFFAOYSA-N 2-(chloromethyl)oxirane;4-[2-(4-hydroxyphenyl)propan-2-yl]phenol Chemical compound ClCC1CO1.C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 KUBDPQJOLOUJRM-UHFFFAOYSA-N 0.000 description 3
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- 150000001875 compounds Chemical class 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 230000002209 hydrophobic effect Effects 0.000 description 3
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- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 239000011490 mineral wool Substances 0.000 description 3
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- 229920003986 novolac Polymers 0.000 description 3
- 150000002989 phenols Chemical class 0.000 description 3
- 239000000080 wetting agent Substances 0.000 description 3
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 2
- KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 description 2
- 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 2
- QOHHOCDXTLIHPG-UHFFFAOYSA-N 4,4-diphenylcyclohexane-1,1-diol Chemical compound C1CC(O)(O)CCC1(C=1C=CC=CC=1)C1=CC=CC=C1 QOHHOCDXTLIHPG-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
- 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
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
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- 238000013329 compounding Methods 0.000 description 2
- VEIOBOXBGYWJIT-UHFFFAOYSA-N cyclohexane;methanol Chemical compound OC.OC.C1CCCCC1 VEIOBOXBGYWJIT-UHFFFAOYSA-N 0.000 description 2
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- 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
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- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
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- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 1
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- 229920000049 Carbon (fiber) Polymers 0.000 description 1
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- BIOOACNPATUQFW-UHFFFAOYSA-N calcium;dioxido(dioxo)molybdenum Chemical compound [Ca+2].[O-][Mo]([O-])(=O)=O BIOOACNPATUQFW-UHFFFAOYSA-N 0.000 description 1
- OYACROKNLOSFPA-UHFFFAOYSA-N calcium;dioxido(oxo)silane Chemical compound [Ca+2].[O-][Si]([O-])=O OYACROKNLOSFPA-UHFFFAOYSA-N 0.000 description 1
- ILOKQJWLMPPMQU-UHFFFAOYSA-N calcium;oxido(oxo)borane Chemical compound [Ca+2].[O-]B=O.[O-]B=O ILOKQJWLMPPMQU-UHFFFAOYSA-N 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
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- 239000000356 contaminant Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000011258 core-shell material Substances 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 125000006841 cyclic skeleton Chemical group 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 125000004427 diamine group Chemical group 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000004205 dimethyl polysiloxane Substances 0.000 description 1
- KZHJGOXRZJKJNY-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical class O=[Si]=O.O=[Si]=O.O=[Al]O[Al]=O.O=[Al]O[Al]=O.O=[Al]O[Al]=O KZHJGOXRZJKJNY-UHFFFAOYSA-N 0.000 description 1
- PVAONLSZTBKFKM-UHFFFAOYSA-N diphenylmethanediol Chemical compound C=1C=CC=CC=1C(O)(O)C1=CC=CC=C1 PVAONLSZTBKFKM-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 239000011152 fibreglass Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 239000005350 fused silica glass Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000011491 glass wool Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- 239000003906 humectant Substances 0.000 description 1
- 230000005661 hydrophobic surface Effects 0.000 description 1
- 150000002462 imidazolines Chemical class 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N iron oxide Inorganic materials [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 1
- 230000001788 irregular Effects 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 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
- 239000006072 paste Substances 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
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 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
- 238000002360 preparation method Methods 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 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
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000003512 tertiary amines Chemical group 0.000 description 1
- 125000001302 tertiary amino group Chemical group 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 compound [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
- PZRXQXJGIQEYOG-UHFFFAOYSA-N zinc;oxido(oxo)borane Chemical compound [Zn+2].[O-]B=O.[O-]B=O PZRXQXJGIQEYOG-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
-
- 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
- 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
- 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
- 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 |
|---|---|
| KR20160025567A true KR20160025567A (ko) | 2016-03-08 |
Family
ID=48703223
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020167001817A Withdrawn KR20160025567A (ko) | 2013-06-28 | 2014-06-26 | 시밍 응용을 위한 고모듈러스 에폭시 접착제 |
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) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20210025671A (ko) * | 2018-07-25 | 2021-03-09 | 헨켈 아이피 앤드 홀딩 게엠베하 | 신속 경화 에폭시 아크릴 액체 심 |
Families Citing this family (12)
| 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 |
| 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
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20210025671A (ko) * | 2018-07-25 | 2021-03-09 | 헨켈 아이피 앤드 홀딩 게엠베하 | 신속 경화 에폭시 아크릴 액체 심 |
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 |
| CA2917013A1 (en) | 2014-12-31 |
| WO2014210298A1 (en) | 2014-12-31 |
| EP2818492B1 (en) | 2018-04-04 |
| 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 |
|---|---|---|---|
| PA0105 | International application |
Patent event date: 20160121 Patent event code: PA01051R01D Comment text: International Patent Application |
|
| PG1501 | Laying open of application | ||
| PC1203 | Withdrawal of no request for examination | ||
| WITN | Application deemed withdrawn, e.g. because no request for examination was filed or no examination fee was paid |