AU2012336202B2 - Structural adhesive and bonding application thereof - Google Patents
Structural adhesive and bonding application thereof Download PDFInfo
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- AU2012336202B2 AU2012336202B2 AU2012336202A AU2012336202A AU2012336202B2 AU 2012336202 B2 AU2012336202 B2 AU 2012336202B2 AU 2012336202 A AU2012336202 A AU 2012336202A AU 2012336202 A AU2012336202 A AU 2012336202A AU 2012336202 B2 AU2012336202 B2 AU 2012336202B2
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- amine
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- 239000000853 adhesive Substances 0.000 title claims abstract description 87
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 87
- 239000002245 particle Substances 0.000 claims abstract description 94
- 229920000647 polyepoxide Polymers 0.000 claims abstract description 78
- 239000003822 epoxy resin Substances 0.000 claims abstract description 71
- 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 claims abstract description 51
- 239000000203 mixture Substances 0.000 claims abstract description 49
- 229920001971 elastomer Polymers 0.000 claims abstract description 47
- 229920000642 polymer Polymers 0.000 claims abstract description 40
- 150000001412 amines Chemical class 0.000 claims abstract description 37
- 239000011258 core-shell material Substances 0.000 claims abstract description 33
- 239000003054 catalyst Substances 0.000 claims abstract description 30
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 30
- -1 cyclic amine compound Chemical class 0.000 claims abstract description 29
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims abstract description 29
- 229910052751 metal Inorganic materials 0.000 claims abstract description 26
- 239000002184 metal Substances 0.000 claims abstract description 26
- 239000011256 inorganic filler Substances 0.000 claims abstract description 25
- 229910003475 inorganic filler Inorganic materials 0.000 claims abstract description 25
- 229920006393 polyether sulfone Polymers 0.000 claims abstract description 12
- 238000000518 rheometry Methods 0.000 claims abstract description 12
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000004593 Epoxy Substances 0.000 claims description 48
- 239000000758 substrate Substances 0.000 claims description 22
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 18
- 239000002313 adhesive film Substances 0.000 claims description 15
- 239000000806 elastomer Substances 0.000 claims description 14
- 229920000459 Nitrile rubber Polymers 0.000 claims description 12
- 230000009477 glass transition Effects 0.000 claims description 12
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 claims description 10
- 238000012360 testing method Methods 0.000 claims description 10
- 125000000524 functional group Chemical group 0.000 claims description 9
- 229920000768 polyamine Polymers 0.000 claims description 8
- 239000004698 Polyethylene Substances 0.000 claims description 7
- NTXGQCSETZTARF-UHFFFAOYSA-N buta-1,3-diene;prop-2-enenitrile Chemical compound C=CC=C.C=CC#N NTXGQCSETZTARF-UHFFFAOYSA-N 0.000 claims description 7
- 229920001577 copolymer Polymers 0.000 claims description 7
- 229920000573 polyethylene Polymers 0.000 claims description 7
- XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical class C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 claims description 6
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 6
- 230000002209 hydrophobic effect Effects 0.000 claims description 6
- IRLQAJPIHBZROB-UHFFFAOYSA-N buta-2,3-dienenitrile Chemical compound C=C=CC#N IRLQAJPIHBZROB-UHFFFAOYSA-N 0.000 claims description 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 150000004885 piperazines Chemical class 0.000 claims description 5
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 4
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 claims description 4
- VZXTWGWHSMCWGA-UHFFFAOYSA-N 1,3,5-triazine-2,4-diamine Chemical compound NC1=NC=NC(N)=N1 VZXTWGWHSMCWGA-UHFFFAOYSA-N 0.000 claims description 3
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 3
- 239000004695 Polyether sulfone Substances 0.000 claims description 3
- 230000032683 aging Effects 0.000 claims description 3
- HAMNKKUPIHEESI-UHFFFAOYSA-N aminoguanidine Chemical compound NNC(N)=N HAMNKKUPIHEESI-UHFFFAOYSA-N 0.000 claims description 3
- 239000000805 composite resin Substances 0.000 claims description 3
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 3
- 229920000058 polyacrylate Polymers 0.000 claims description 2
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- 239000000463 material Substances 0.000 abstract description 15
- 125000001931 aliphatic group Chemical group 0.000 abstract description 9
- 150000002739 metals Chemical class 0.000 abstract description 3
- 238000001723 curing Methods 0.000 description 60
- 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 description 36
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 28
- 239000002131 composite material Substances 0.000 description 24
- 229920005989 resin Polymers 0.000 description 17
- 239000011347 resin Substances 0.000 description 17
- 239000007788 liquid Substances 0.000 description 16
- 238000009472 formulation Methods 0.000 description 11
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 10
- 229910021485 fumed silica Inorganic materials 0.000 description 10
- 238000002156 mixing Methods 0.000 description 10
- 239000000126 substance Substances 0.000 description 10
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 9
- 125000003700 epoxy group Chemical group 0.000 description 9
- 239000011159 matrix material Substances 0.000 description 9
- 238000004026 adhesive bonding Methods 0.000 description 6
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical class NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 5
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- ULKLGIFJWFIQFF-UHFFFAOYSA-N 5K8XI641G3 Chemical compound CCC1=NC=C(C)N1 ULKLGIFJWFIQFF-UHFFFAOYSA-N 0.000 description 5
- 229920003319 Araldite® Polymers 0.000 description 5
- 239000004825 One-part adhesive Substances 0.000 description 5
- 239000011324 bead Substances 0.000 description 5
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- 239000012745 toughening agent Substances 0.000 description 5
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 4
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 4
- 239000000835 fiber Substances 0.000 description 4
- 238000013035 low temperature curing Methods 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000004416 thermosoftening plastic Substances 0.000 description 4
- 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 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- 229920012266 Poly(ether sulfone) PES Polymers 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 238000005538 encapsulation Methods 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 150000002460 imidazoles Chemical class 0.000 description 3
- 239000004850 liquid epoxy resins (LERs) Substances 0.000 description 3
- 150000008442 polyphenolic compounds Chemical class 0.000 description 3
- 235000013824 polyphenols Nutrition 0.000 description 3
- 239000000600 sorbitol Substances 0.000 description 3
- 238000007655 standard test method Methods 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- AHDSRXYHVZECER-UHFFFAOYSA-N 2,4,6-tris[(dimethylamino)methyl]phenol Chemical compound CN(C)CC1=CC(CN(C)C)=C(O)C(CN(C)C)=C1 AHDSRXYHVZECER-UHFFFAOYSA-N 0.000 description 2
- 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 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 2
- SDDLEVPIDBLVHC-UHFFFAOYSA-N Bisphenol Z Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)CCCCC1 SDDLEVPIDBLVHC-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- MGJKQDOBUOMPEZ-UHFFFAOYSA-N N,N'-dimethylurea Chemical compound CNC(=O)NC MGJKQDOBUOMPEZ-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 125000002723 alicyclic group Chemical group 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000004205 dimethyl polysiloxane Substances 0.000 description 2
- 239000013536 elastomeric material Substances 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 229920006332 epoxy adhesive Polymers 0.000 description 2
- 239000003292 glue Substances 0.000 description 2
- 230000005484 gravity Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
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- 230000014759 maintenance of location Effects 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 2
- 229920000151 polyglycol Polymers 0.000 description 2
- 239000010695 polyglycol Substances 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 238000007665 sagging Methods 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000004381 surface treatment Methods 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- 229920001187 thermosetting polymer Polymers 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 1
- VOZKAJLKRJDJLL-UHFFFAOYSA-N 2,4-diaminotoluene Chemical compound CC1=CC=C(N)C=C1N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-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
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- XUSNPFGLKGCWGN-UHFFFAOYSA-N 3-[4-(3-aminopropyl)piperazin-1-yl]propan-1-amine Chemical group NCCCN1CCN(CCCN)CC1 XUSNPFGLKGCWGN-UHFFFAOYSA-N 0.000 description 1
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 1
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- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
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- 241000238367 Mya arenaria Species 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
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- 125000000217 alkyl group Chemical group 0.000 description 1
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- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- IMUDHTPIFIBORV-UHFFFAOYSA-N aminoethylpiperazine Chemical group NCCN1CCNCC1 IMUDHTPIFIBORV-UHFFFAOYSA-N 0.000 description 1
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- AFEQENGXSMURHA-UHFFFAOYSA-N oxiran-2-ylmethanamine Chemical compound NCC1CO1 AFEQENGXSMURHA-UHFFFAOYSA-N 0.000 description 1
- 125000000466 oxiranyl group Chemical group 0.000 description 1
- FTDXCHCAMNRNNY-UHFFFAOYSA-N phenol Chemical compound OC1=CC=CC=C1.OC1=CC=CC=C1 FTDXCHCAMNRNNY-UHFFFAOYSA-N 0.000 description 1
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- IGALFTFNPPBUDN-UHFFFAOYSA-N phenyl-[2,3,4,5-tetrakis(oxiran-2-ylmethyl)phenyl]methanediamine Chemical compound C=1C(CC2OC2)=C(CC2OC2)C(CC2OC2)=C(CC2OC2)C=1C(N)(N)C1=CC=CC=C1 IGALFTFNPPBUDN-UHFFFAOYSA-N 0.000 description 1
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- NMCOHHUAMHYFBL-UHFFFAOYSA-N piperazine;2-piperazin-1-ylethanamine Chemical compound C1CNCCN1.NCCN1CCNCC1 NMCOHHUAMHYFBL-UHFFFAOYSA-N 0.000 description 1
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- 230000009974 thixotropic effect Effects 0.000 description 1
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Classifications
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- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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Landscapes
- Chemical & Material Sciences (AREA)
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- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
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- Polymers & Plastics (AREA)
- Physics & Mathematics (AREA)
- Toxicology (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Epoxy Resins (AREA)
- Laminated Bodies (AREA)
- Adhesive Tapes (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201161557538P | 2011-11-09 | 2011-11-09 | |
| US61/557,538 | 2011-11-09 | ||
| PCT/US2012/060975 WO2013070415A1 (en) | 2011-11-09 | 2012-10-19 | Structural adhesive and bonding application thereof |
Publications (2)
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| AU2012336202A1 AU2012336202A1 (en) | 2014-02-06 |
| AU2012336202B2 true AU2012336202B2 (en) | 2015-12-03 |
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|---|---|---|---|
| AU2012336202A Ceased AU2012336202B2 (en) | 2011-11-09 | 2012-10-19 | Structural adhesive and bonding application thereof |
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| JP (1) | JP5964980B2 (https=) |
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| US8895148B2 (en) * | 2011-11-09 | 2014-11-25 | Cytec Technology Corp. | Structural adhesive and bonding application thereof |
| US9254622B2 (en) * | 2012-04-23 | 2016-02-09 | University Of Washington | Bond ply for adhesive bonding of composites and associated systems and methods |
| 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 |
| JP6463271B2 (ja) | 2013-10-11 | 2019-01-30 | 株式会社カネカ | コアシェルポリマー含有エポキシ樹脂組成物、その硬化物、及びその製造方法 |
| JP6061837B2 (ja) * | 2013-12-05 | 2017-01-18 | アイシン化工株式会社 | 構造用接着剤組成物 |
| US9890306B2 (en) * | 2014-05-28 | 2018-02-13 | Xerox Corporation | Use of epoxy film adhesive with high ink compatibility and thermal oxidative stability for printhead interstitial bonding in in high density printheads |
| GB201411586D0 (en) * | 2014-06-30 | 2014-08-13 | Hexcel Composites Ltd | Adhesive composition |
| WO2016007324A1 (en) * | 2014-07-08 | 2016-01-14 | Dow Global Technologies Llc | DELAYED CURING HIGH Tg CRASH DURABLE ADHESIVE |
| EP3233438B1 (en) | 2014-12-18 | 2021-02-17 | Cytec Industries Inc. | Modified resin systems suitable for liquid resin infusion |
| GB2533776B (en) * | 2014-12-23 | 2020-11-04 | Hexcel Composites Ltd | Resin Composition |
| FR3031109B1 (fr) * | 2014-12-24 | 2018-08-17 | Arkema France | Composition de polymeres, son procede de preparation, son utilisation et composition la comprenant |
| CN104559064A (zh) * | 2015-01-28 | 2015-04-29 | 江苏恒神纤维材料有限公司 | 一种高韧性高Tg环氧树脂及其制备方法 |
| EP3263647A4 (en) * | 2015-02-27 | 2018-10-10 | Toray Industries, Inc. | Epoxy resin composition, cured epoxy resin product, prepreg, and fiber-reinforced composite material |
| ES2964815T3 (es) * | 2015-03-19 | 2024-04-09 | Zephyros Inc | Acidos esterificados para su uso en materiales poliméricos |
| DE102015105553A1 (de) * | 2015-04-12 | 2016-10-13 | ATN Hölzel GmbH | Verfahren zur Herstellung einer lastoptimierten Klebeverbindung |
| KR20170141744A (ko) * | 2015-04-30 | 2017-12-26 | 헨켈 아게 운트 코. 카게아아 | 1 액형 경화성 접착제 조성물 및 이의 용도 |
| JP2018522954A (ja) | 2015-05-01 | 2018-08-16 | ロード コーポレイション | ゴム接合用接着剤 |
| CN204994154U (zh) * | 2015-09-08 | 2016-01-20 | 中兴通讯股份有限公司 | 一种通讯设备结构 |
| EP3347398B1 (en) * | 2015-09-10 | 2024-07-31 | DDP Specialty Electronic Materials US, LLC | One-component toughened epoxy adhesives with improved adhesion to oily surfaces and high wash-off resistance |
| US11242427B2 (en) * | 2015-10-20 | 2022-02-08 | Ppg Industries Ohio, Inc. | Structural adhesive compositions |
| EP3170877B1 (en) | 2015-11-19 | 2020-11-18 | 3M Innovative Properties Company | Structural adhesive with improved failure mode |
| EP3170860B1 (en) | 2015-11-19 | 2020-07-29 | 3M Innovative Properties Company | Structural adhesive with improved corrosion resistance |
| US10351661B2 (en) | 2015-12-10 | 2019-07-16 | Ppg Industries Ohio, Inc. | Method for producing an aminimide |
| US10377928B2 (en) * | 2015-12-10 | 2019-08-13 | Ppg Industries Ohio, Inc. | Structural adhesive compositions |
| DE102015224997A1 (de) * | 2015-12-11 | 2017-06-14 | Henkel Ag & Co. Kgaa | Verfahren zur Konfektionierung und Auftragung von Klebstoffen |
| WO2017124664A1 (en) | 2016-01-21 | 2017-07-27 | 3M Innovative Properties Company | Optical camouflage filters |
| CN105647124A (zh) * | 2016-04-12 | 2016-06-08 | 苏州甫众塑胶有限公司 | 一种电子封装塑胶材料及其制备方法 |
| TW201816024A (zh) * | 2016-05-09 | 2018-05-01 | 漢高智慧財產控股公司 | 含有反應性倍半矽氧烷的黏著組合物 |
| JP2018016672A (ja) * | 2016-07-25 | 2018-02-01 | アイカ工業株式会社 | グリース状エポキシ樹脂組成物 |
| KR101806739B1 (ko) * | 2016-09-28 | 2017-12-07 | 현대자동차주식회사 | 테이프형 구조용 접착제 조성물 |
| RU2627419C1 (ru) * | 2016-10-12 | 2017-08-08 | Федеральное государственное унитарное предприятие "Всероссийский научно-исследовательский институт авиационных материалов" (ФГУП "ВИАМ") | Эпоксидное клеевое связующее и пленочный клей на его основе |
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| US11279795B2 (en) | 2017-06-29 | 2022-03-22 | 3M Innovative Properties Company | Curable composition |
| WO2019087258A1 (ja) * | 2017-10-30 | 2019-05-09 | 日立化成株式会社 | 樹脂組成物、硬化物、成形体及びその製造方法、並びに、フィルムコンデンサ及びその製造方法 |
| CN107828360A (zh) * | 2017-11-16 | 2018-03-23 | 西安长峰机电研究所 | 一种常温固化固体火箭发动机喷管结构粘接剂 |
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| KR20210142588A (ko) * | 2018-12-18 | 2021-11-25 | 사이텍 인더스트리스 인코포레이티드 | 난연성 에폭시 조성물 및 이의 사용 방법 |
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| WO2013070415A1 (en) | 2013-05-16 |
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| IN2014CN03459A (https=) | 2015-10-09 |
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| MX2014005116A (es) | 2014-05-28 |
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| US8895148B2 (en) | 2014-11-25 |
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