TWI426091B - 用於固化環氧化物之觸媒 - Google Patents
用於固化環氧化物之觸媒 Download PDFInfo
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- TWI426091B TWI426091B TW97122347A TW97122347A TWI426091B TW I426091 B TWI426091 B TW I426091B TW 97122347 A TW97122347 A TW 97122347A TW 97122347 A TW97122347 A TW 97122347A TW I426091 B TWI426091 B TW I426091B
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- epoxy compound
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- 239000003054 catalyst Substances 0.000 title claims abstract description 28
- 150000002118 epoxides Chemical class 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 67
- 239000004593 Epoxy Substances 0.000 claims abstract description 52
- 150000004693 imidazolium salts Chemical class 0.000 claims abstract description 21
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 19
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 19
- 150000001450 anions Chemical class 0.000 claims abstract description 18
- 125000003118 aryl group Chemical group 0.000 claims abstract description 18
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 18
- 229910052698 phosphorus Inorganic materials 0.000 claims abstract description 8
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000011574 phosphorus Substances 0.000 claims abstract description 7
- 239000000203 mixture Substances 0.000 claims description 64
- -1 alkyl phosphate Chemical compound 0.000 claims description 21
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 19
- 125000000962 organic group Chemical group 0.000 claims description 16
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 14
- 229920001568 phenolic resin Polymers 0.000 claims description 14
- 239000005011 phenolic resin Substances 0.000 claims description 14
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 12
- 150000001412 amines Chemical class 0.000 claims description 11
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- 229910019142 PO4 Inorganic materials 0.000 claims description 9
- 239000000853 adhesive Substances 0.000 claims description 9
- 230000001070 adhesive effect Effects 0.000 claims description 9
- 239000010452 phosphate Substances 0.000 claims description 9
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 8
- 125000003700 epoxy group Chemical group 0.000 claims description 8
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- 239000004615 ingredient Substances 0.000 claims description 7
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
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- 239000011347 resin Substances 0.000 claims description 7
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims description 6
- 238000000576 coating method Methods 0.000 claims description 6
- 239000002131 composite material Substances 0.000 claims description 6
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 claims description 5
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- 238000005266 casting Methods 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 claims description 4
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 3
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 3
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- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
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- 125000005341 metaphosphate group Chemical group 0.000 claims description 2
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- 229910021529 ammonia Inorganic materials 0.000 description 5
- 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 5
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- QUSNBJAOOMFDIB-UHFFFAOYSA-N monoethyl amine Natural products CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 4
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- 150000003839 salts Chemical class 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
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- RAXXELZNTBOGNW-UHFFFAOYSA-O Imidazolium Chemical compound C1=C[NH+]=CN1 RAXXELZNTBOGNW-UHFFFAOYSA-O 0.000 description 3
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- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-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
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- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
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- 238000006116 polymerization reaction Methods 0.000 description 3
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- 210000003462 vein Anatomy 0.000 description 3
- IJZZYQTVHBGRHO-UHFFFAOYSA-N 1-[2-(2-propoxyethoxy)ethoxy]propane-1,3-diamine Chemical compound CCCOCCOCCOC(N)CCN IJZZYQTVHBGRHO-UHFFFAOYSA-N 0.000 description 2
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 2
- 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 2
- XMTQQYYKAHVGBJ-UHFFFAOYSA-N 3-(3,4-DICHLOROPHENYL)-1,1-DIMETHYLUREA Chemical compound CN(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 XMTQQYYKAHVGBJ-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
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- OFTSSFREMCBZMF-UHFFFAOYSA-M 1-ethyl-2,3-dimethylimidazol-3-ium;acetate Chemical compound CC([O-])=O.CC[N+]=1C=CN(C)C=1C OFTSSFREMCBZMF-UHFFFAOYSA-M 0.000 description 1
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- BKCCAYLNRIRKDJ-UHFFFAOYSA-N 2-phenyl-4,5-dihydro-1h-imidazole Chemical compound N1CCN=C1C1=CC=CC=C1 BKCCAYLNRIRKDJ-UHFFFAOYSA-N 0.000 description 1
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- 229920002732 Polyanhydride Polymers 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- QLBRROYTTDFLDX-UHFFFAOYSA-N [3-(aminomethyl)cyclohexyl]methanamine Chemical compound NCC1CCCC(CN)C1 QLBRROYTTDFLDX-UHFFFAOYSA-N 0.000 description 1
- FDLQZKYLHJJBHD-UHFFFAOYSA-N [3-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC(CN)=C1 FDLQZKYLHJJBHD-UHFFFAOYSA-N 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- XIVMBHINNQPRLN-UHFFFAOYSA-M acetic acid;1-ethyl-2,3-dimethylimidazol-3-ium;acetate Chemical compound CC(O)=O.CC([O-])=O.CCN1C=C[N+](C)=C1C XIVMBHINNQPRLN-UHFFFAOYSA-M 0.000 description 1
- 125000004018 acid anhydride group Chemical group 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000007824 aliphatic compounds Chemical class 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- IMUDHTPIFIBORV-UHFFFAOYSA-N aminoethylpiperazine Chemical compound NCCN1CCNCC1 IMUDHTPIFIBORV-UHFFFAOYSA-N 0.000 description 1
- 150000001449 anionic compounds Chemical class 0.000 description 1
- XMSVKICKONKVNM-UHFFFAOYSA-N bicyclo[2.2.1]heptane-3,4-diamine Chemical compound C1CC2(N)C(N)CC1C2 XMSVKICKONKVNM-UHFFFAOYSA-N 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- 239000004917 carbon fiber Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- JXCGFZXSOMJFOA-UHFFFAOYSA-N chlorotoluron Chemical compound CN(C)C(=O)NC1=CC=C(C)C(Cl)=C1 JXCGFZXSOMJFOA-UHFFFAOYSA-N 0.000 description 1
- 239000008199 coating composition Substances 0.000 description 1
- 230000001010 compromised effect Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- SSJXIUAHEKJCMH-UHFFFAOYSA-N cyclohexane-1,2-diamine Chemical compound NC1CCCCC1N SSJXIUAHEKJCMH-UHFFFAOYSA-N 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
- YQLZOAVZWJBZSY-UHFFFAOYSA-N decane-1,10-diamine Chemical compound NCCCCCCCCCCN YQLZOAVZWJBZSY-UHFFFAOYSA-N 0.000 description 1
- 239000012973 diazabicyclooctane Substances 0.000 description 1
- 238000001938 differential scanning calorimetry curve Methods 0.000 description 1
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
- QVKQJEWZVQFGIY-UHFFFAOYSA-N dipropyl hydrogen phosphate Chemical compound CCCOP(O)(=O)OCCC QVKQJEWZVQFGIY-UHFFFAOYSA-N 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- QFTYSVGGYOXFRQ-UHFFFAOYSA-N dodecane-1,12-diamine Chemical compound NCCCCCCCCCCCCN QFTYSVGGYOXFRQ-UHFFFAOYSA-N 0.000 description 1
- IWBOPFCKHIJFMS-UHFFFAOYSA-N ethylene glycol bis(2-aminoethyl) ether Chemical compound NCCOCCOCCN IWBOPFCKHIJFMS-UHFFFAOYSA-N 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 150000002462 imidazolines Chemical class 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 229910001412 inorganic anion Inorganic materials 0.000 description 1
- 239000011256 inorganic filler Substances 0.000 description 1
- 229910003475 inorganic filler Inorganic materials 0.000 description 1
- 239000001023 inorganic pigment Substances 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 150000002927 oxygen compounds Chemical class 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- 125000004437 phosphorous atom Chemical group 0.000 description 1
- 229920002120 photoresistant polymer Polymers 0.000 description 1
- VIQXDCYEJAOMDP-UHFFFAOYSA-N piperazine pyrazine Chemical compound C1CNCCN1.C1=CN=CC=N1 VIQXDCYEJAOMDP-UHFFFAOYSA-N 0.000 description 1
- 229920000962 poly(amidoamine) Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
- 239000011253 protective coating Substances 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000012779 reinforcing material Substances 0.000 description 1
- 229920003987 resole Polymers 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 230000003678 scratch resistant effect Effects 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
- 238000010518 undesired secondary reaction Methods 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
- C08G59/68—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 catalysts used
- C08G59/686—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 catalysts used containing nitrogen
-
- 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
- C08G59/68—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 catalysts used
- C08G59/688—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 catalysts used containing phosphorus
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/249921—Web or sheet containing structurally defined element or component
- Y10T428/249924—Noninterengaged fiber-containing paper-free web or sheet which is not of specified porosity
- Y10T428/24994—Fiber embedded in or on the surface of a polymeric matrix
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31511—Of epoxy ether
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Epoxy Resins (AREA)
- Paints Or Removers (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP07110279 | 2007-06-14 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW200906889A TW200906889A (en) | 2009-02-16 |
| TWI426091B true TWI426091B (zh) | 2014-02-11 |
Family
ID=39830825
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW97122347A TWI426091B (zh) | 2007-06-14 | 2008-06-13 | 用於固化環氧化物之觸媒 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US8202580B2 (enExample) |
| EP (1) | EP2158250B1 (enExample) |
| JP (1) | JP5260639B2 (enExample) |
| KR (1) | KR101438867B1 (enExample) |
| CN (1) | CN101687977B (enExample) |
| AT (1) | ATE531746T1 (enExample) |
| TW (1) | TWI426091B (enExample) |
| WO (1) | WO2008152002A1 (enExample) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5579059B2 (ja) | 2007-06-12 | 2014-08-27 | ビーエーエスエフ ソシエタス・ヨーロピア | エポキシドの硬化触媒 |
| CN103739827B (zh) * | 2007-07-26 | 2016-11-23 | 味之素株式会社 | 树脂组合物 |
| JP5377990B2 (ja) * | 2009-01-26 | 2013-12-25 | 株式会社ティ−アンドケイ東華 | 液状の潜在性硬化剤組成物及び一液性の硬化性エポキシド組成物 |
| WO2011025040A1 (ja) * | 2009-08-31 | 2011-03-03 | 日本合成化学工業株式会社 | エポキシ樹脂用硬化剤 |
| EP2387081B1 (en) | 2010-05-11 | 2015-09-30 | Samsung Electronics Co., Ltd. | Semiconductor light emitting device and method for fabricating the same |
| WO2012136273A1 (de) | 2011-04-08 | 2012-10-11 | Basf Se | Hyperverzweigte polymere zur modifikation der zähigkeit von anionisch gehärteten epoxidharz-systemen |
| JP5652617B2 (ja) * | 2011-04-27 | 2015-01-14 | 大日本印刷株式会社 | 熱硬化型粘接着剤組成物、粘接着シート、及び粘接着シートの製造方法 |
| JP6109611B2 (ja) * | 2013-03-18 | 2017-04-05 | 積水化学工業株式会社 | 熱硬化性樹脂組成物、及び、半導体装置の製造方法 |
| DE102013008723A1 (de) | 2013-05-23 | 2014-11-27 | Deutsche Institute Für Textil- Und Faserforschung Denkendorf | Polymerisierbare Reaktionsmischung zur Herstellung von Epoxidharzen und deren Verwendung |
| BR112016018860B1 (pt) * | 2014-02-19 | 2021-06-22 | Basf Se | Processo para produção contínua de materiais compósitos em multicamadas, e, usina de produção para realização do processo para produção de compósitos em multicamadas |
| US10073845B2 (en) | 2015-01-07 | 2018-09-11 | International Business Machines Corporation | Estimating article publication dates and authors based on social media context |
| WO2016158757A1 (ja) * | 2015-03-27 | 2016-10-06 | 東レ株式会社 | 繊維強化複合材料用２液型エポキシ樹脂組成物および繊維強化複合材料 |
| US10035926B2 (en) | 2016-04-22 | 2018-07-31 | PRC—DeSoto International, Inc. | Ionic liquid catalysts in sulfur-containing polymer compositions |
| KR102698219B1 (ko) * | 2021-11-26 | 2024-08-26 | 한국과학기술연구원 | 에폭시 수지용 잠재성 경화제의 제조방법 및 이에 따른 에폭시 수지용 잠재성 경화제 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3635894A (en) * | 1969-11-06 | 1972-01-18 | Ppg Industries Inc | Curable epoxy resin compositions containing organoimidazolium salt |
| WO1997021752A1 (en) * | 1995-12-14 | 1997-06-19 | Minnesota Mining And Manufacturing Company | Latent curing agent compositions and a method of making |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2416408C3 (de) | 1974-04-04 | 1978-08-17 | Hitachi Chemical Co., Ltd. | Wärmehärtbare Gemische auf der Basis eines Epoxyharzes und einer komplexen Imidazoliumsalzverbindung und ihr Herstellungsverfahren |
| FR2486079A1 (fr) * | 1980-07-07 | 1982-01-08 | Rhone Poulenc Agrochimie | Sels quaternaires d'alcoyl-1-imidazolium de l'acide phosphoreux ou ses monoesters, procedes pour les preparer et compositions fongicides les contenant |
| JPS6129321A (ja) * | 1984-07-20 | 1986-02-10 | 松下電器産業株式会社 | 電気掃除機の床ノズル |
| JPS61293217A (ja) * | 1985-06-20 | 1986-12-24 | Masako Matsumoto | エポキシ樹脂硬化剤 |
| ATE243227T1 (de) * | 1990-05-21 | 2003-07-15 | Dow Global Technologies Inc | Latente katalysatoren, härtungsinhibierte epoxyharzzusammensetzungen und daraus hergestellte laminate |
| DE4110219A1 (de) | 1991-03-28 | 1992-10-01 | Huels Troisdorf | Verfahren zur herstellung von prepregs mit loesungsmittelfreiem epoxidharz |
| US6180696B1 (en) | 1997-02-19 | 2001-01-30 | Georgia Tech Research Corporation | No-flow underfill of epoxy resin, anhydride, fluxing agent and surfactant |
| WO2002048236A1 (en) * | 2000-12-14 | 2002-06-20 | Hitachi Chemical Co., Ltd. | Varnish for laminate or prepreg, laminate or prepreg obtained with this varnish, and printed circuit board made with this laminate or prepreg |
| CA2598156C (en) * | 2002-08-16 | 2011-02-08 | Cytec Canada Inc. | Phosphonium and imidazolium salts and methods of their preparation |
| JP2004217859A (ja) | 2003-01-17 | 2004-08-05 | Hitachi Chem Co Ltd | 接着シートの製造方法、半導体装置およびその製造方法 |
| DE10333239A1 (de) * | 2003-07-21 | 2005-03-10 | Basf Ag | Verfahren zur Herstellung von gereinigten 1,3- substituierten Imidazoliumsalzen |
| WO2005116038A1 (ja) * | 2004-05-28 | 2005-12-08 | San-Apro Limited | 新規なオニウムおよび遷移金属錯体のフッ素化アルキルフルオロリン酸塩 |
| JP4844130B2 (ja) | 2005-02-03 | 2011-12-28 | 住友化学株式会社 | β−ヒドロキシエーテル類の製造方法 |
| JP2007262401A (ja) * | 2006-03-03 | 2007-10-11 | San Apro Kk | 活性エネルギー線硬化性光学的立体造形用樹脂組成物およびそれを硬化した光造形物 |
-
2008
- 2008-06-06 JP JP2010511597A patent/JP5260639B2/ja not_active Expired - Fee Related
- 2008-06-06 CN CN2008800198886A patent/CN101687977B/zh active Active
- 2008-06-06 AT AT08760685T patent/ATE531746T1/de active
- 2008-06-06 EP EP20080760685 patent/EP2158250B1/de active Active
- 2008-06-06 US US12/663,868 patent/US8202580B2/en active Active
- 2008-06-06 WO PCT/EP2008/057115 patent/WO2008152002A1/de not_active Ceased
- 2008-06-06 KR KR1020107000779A patent/KR101438867B1/ko not_active Expired - Fee Related
- 2008-06-13 TW TW97122347A patent/TWI426091B/zh not_active IP Right Cessation
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3635894A (en) * | 1969-11-06 | 1972-01-18 | Ppg Industries Inc | Curable epoxy resin compositions containing organoimidazolium salt |
| WO1997021752A1 (en) * | 1995-12-14 | 1997-06-19 | Minnesota Mining And Manufacturing Company | Latent curing agent compositions and a method of making |
Also Published As
| Publication number | Publication date |
|---|---|
| KR101438867B1 (ko) | 2014-09-11 |
| CN101687977A (zh) | 2010-03-31 |
| EP2158250B1 (de) | 2011-11-02 |
| JP2010530908A (ja) | 2010-09-16 |
| WO2008152002A1 (de) | 2008-12-18 |
| CN101687977B (zh) | 2012-08-15 |
| EP2158250A1 (de) | 2010-03-03 |
| US20100166971A1 (en) | 2010-07-01 |
| US8202580B2 (en) | 2012-06-19 |
| KR20100044171A (ko) | 2010-04-29 |
| TW200906889A (en) | 2009-02-16 |
| ATE531746T1 (de) | 2011-11-15 |
| JP5260639B2 (ja) | 2013-08-14 |
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| MM4A | Annulment or lapse of patent due to non-payment of fees |