JP5390599B2 - エポキシ樹脂のアダクト及びその製造方法 - Google Patents
エポキシ樹脂のアダクト及びその製造方法 Download PDFInfo
- Publication number
- JP5390599B2 JP5390599B2 JP2011510550A JP2011510550A JP5390599B2 JP 5390599 B2 JP5390599 B2 JP 5390599B2 JP 2011510550 A JP2011510550 A JP 2011510550A JP 2011510550 A JP2011510550 A JP 2011510550A JP 5390599 B2 JP5390599 B2 JP 5390599B2
- Authority
- JP
- Japan
- Prior art keywords
- cyclohexanedimethanol
- cis
- trans
- diglycidyl ether
- ether
- 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
- 229920000647 polyepoxide Polymers 0.000 title claims description 205
- 239000003822 epoxy resin Substances 0.000 title claims description 203
- 238000004519 manufacturing process Methods 0.000 title description 21
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 claims description 187
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 claims description 156
- 150000001875 compounds Chemical class 0.000 claims description 128
- 239000000047 product Substances 0.000 claims description 91
- 239000000463 material Substances 0.000 claims description 81
- 239000000203 mixture Substances 0.000 claims description 66
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 57
- 238000001723 curing Methods 0.000 claims description 54
- 125000003700 epoxy group Chemical group 0.000 claims description 50
- 238000000034 method Methods 0.000 claims description 49
- 229920005989 resin Polymers 0.000 claims description 49
- 239000011347 resin Substances 0.000 claims description 49
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 31
- LUSFFPXRDZKBMF-OCAPTIKFSA-N [(1s,3r)-3-(hydroxymethyl)cyclohexyl]methanol Chemical compound OC[C@H]1CCC[C@@H](CO)C1 LUSFFPXRDZKBMF-OCAPTIKFSA-N 0.000 claims description 29
- LUSFFPXRDZKBMF-YUMQZZPRSA-N [(1s,3s)-3-(hydroxymethyl)cyclohexyl]methanol Chemical compound OC[C@H]1CCC[C@H](CO)C1 LUSFFPXRDZKBMF-YUMQZZPRSA-N 0.000 claims description 26
- 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 description 26
- -1 trans-1,4-cyclohexanedimethanol Ethers Chemical class 0.000 claims description 24
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- 239000002904 solvent Substances 0.000 claims description 23
- 125000001931 aliphatic group Chemical group 0.000 claims description 21
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 20
- 239000007795 chemical reaction product Substances 0.000 claims description 17
- 239000003795 chemical substances by application Substances 0.000 claims description 17
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- 229910021529 ammonia Inorganic materials 0.000 claims description 9
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical compound NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims description 8
- ORLQHILJRHBSAY-UHFFFAOYSA-N [1-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1(CO)CCCCC1 ORLQHILJRHBSAY-UHFFFAOYSA-N 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 8
- 235000013824 polyphenols Nutrition 0.000 claims description 8
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- VQMQXWYQIIUJIT-HXZBBRIXSA-N C(OC[C@H]1CC[C@H](COCC2CO2)CC1)C1CO1 Chemical compound C(OC[C@H]1CC[C@H](COCC2CO2)CC1)C1CO1 VQMQXWYQIIUJIT-HXZBBRIXSA-N 0.000 claims description 7
- 229920000768 polyamine Polymers 0.000 claims description 7
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 6
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 claims description 6
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 5
- ZVCIUUZBXAAZSM-QRHSGQBVSA-N C1C[C@@H](C[C@H](C1)COCC2CO2)CO Chemical compound C1C[C@@H](C[C@H](C1)COCC2CO2)CO ZVCIUUZBXAAZSM-QRHSGQBVSA-N 0.000 claims description 5
- 239000000908 ammonium hydroxide Substances 0.000 claims description 5
- 150000003456 sulfonamides Chemical class 0.000 claims description 5
- 239000004970 Chain extender Substances 0.000 claims description 4
- BXGYYDRIMBPOMN-UHFFFAOYSA-N 2-(hydroxymethoxy)ethoxymethanol Chemical compound OCOCCOCO BXGYYDRIMBPOMN-UHFFFAOYSA-N 0.000 claims description 3
- LUSFFPXRDZKBMF-UHFFFAOYSA-N [3-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCCC(CO)C1 LUSFFPXRDZKBMF-UHFFFAOYSA-N 0.000 claims description 3
- 150000001735 carboxylic acids Chemical class 0.000 claims description 3
- 238000000576 coating method Methods 0.000 claims description 3
- 150000008442 polyphenolic compounds Chemical class 0.000 claims description 3
- YFQPJCUYATWTLO-SXYIOBQASA-N C(C1CO1)OC[C@@H]1CC[C@H](CC1)CO Chemical compound C(C1CO1)OC[C@@H]1CC[C@H](CC1)CO YFQPJCUYATWTLO-SXYIOBQASA-N 0.000 claims description 2
- IVHKZGYFKJRXBD-UHFFFAOYSA-N amino carbamate Chemical compound NOC(N)=O IVHKZGYFKJRXBD-UHFFFAOYSA-N 0.000 claims description 2
- 239000011248 coating agent Substances 0.000 claims description 2
- 239000002131 composite material Substances 0.000 claims description 2
- 238000009730 filament winding Methods 0.000 claims description 2
- RMKLXHFCAADUQT-FEPKRQSRSA-N 2-[[(1S,3S)-3-(oxiran-2-ylmethoxymethyl)cyclohexyl]methoxymethyl]oxirane Chemical compound C(C1CO1)OC[C@@H]1C[C@H](CCC1)COCC1CO1 RMKLXHFCAADUQT-FEPKRQSRSA-N 0.000 claims 2
- 125000004427 diamine group Chemical group 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 56
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 41
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 36
- 239000000243 solution Substances 0.000 description 31
- 238000004448 titration Methods 0.000 description 31
- 229910052757 nitrogen Inorganic materials 0.000 description 24
- 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 23
- 239000000126 substance Substances 0.000 description 23
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 21
- 239000004593 Epoxy Substances 0.000 description 21
- 239000007788 liquid Substances 0.000 description 21
- 230000000052 comparative effect Effects 0.000 description 20
- 238000002474 experimental method Methods 0.000 description 20
- 239000001257 hydrogen Substances 0.000 description 20
- 229910052739 hydrogen Inorganic materials 0.000 description 20
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 19
- 150000001412 amines Chemical class 0.000 description 19
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 18
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 18
- 239000000376 reactant Substances 0.000 description 18
- 238000004817 gas chromatography Methods 0.000 description 17
- 238000010438 heat treatment Methods 0.000 description 17
- 238000012512 characterization method Methods 0.000 description 15
- 239000011521 glass Substances 0.000 description 15
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 14
- 238000000113 differential scanning calorimetry Methods 0.000 description 14
- 125000000524 functional group Chemical group 0.000 description 14
- 238000004458 analytical method Methods 0.000 description 13
- 150000002118 epoxides Chemical group 0.000 description 13
- 238000002360 preparation method Methods 0.000 description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 12
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 11
- 238000005755 formation reaction Methods 0.000 description 11
- 238000002390 rotary evaporation Methods 0.000 description 11
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 10
- 238000006735 epoxidation reaction Methods 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- 238000007259 addition reaction Methods 0.000 description 9
- 125000003118 aryl group Chemical group 0.000 description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- 150000001805 chlorine compounds Chemical class 0.000 description 8
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 8
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 7
- 238000005227 gel permeation chromatography Methods 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- 230000007704 transition Effects 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000012937 correction Methods 0.000 description 6
- 230000009477 glass transition Effects 0.000 description 6
- 239000012535 impurity Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- 238000005859 coupling reaction Methods 0.000 description 5
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- 125000001424 substituent group Chemical group 0.000 description 5
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- 238000012360 testing method Methods 0.000 description 5
- 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 4
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 4
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
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- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
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- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 4
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 4
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- 238000005266 casting Methods 0.000 description 4
- XENVCRGQTABGKY-ZHACJKMWSA-N chlorohydrin Chemical compound CC#CC#CC#CC#C\C=C\C(Cl)CO XENVCRGQTABGKY-ZHACJKMWSA-N 0.000 description 4
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- XKZQKPRCPNGNFR-UHFFFAOYSA-N 2-(3-hydroxyphenyl)phenol Chemical compound OC1=CC=CC(C=2C(=CC=CC=2)O)=C1 XKZQKPRCPNGNFR-UHFFFAOYSA-N 0.000 description 2
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- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
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Classifications
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- 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
- C08G59/182—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 using pre-adducts of epoxy compounds with curing agents
-
- 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
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)
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| US5523208P | 2008-05-22 | 2008-05-22 | |
| US61/055,232 | 2008-05-22 | ||
| PCT/US2009/042643 WO2009142898A1 (en) | 2008-05-22 | 2009-05-04 | Adducts of epoxy resins and process for preparing the same |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2011521073A JP2011521073A (ja) | 2011-07-21 |
| JP2011521073A5 JP2011521073A5 (https=) | 2012-05-10 |
| JP5390599B2 true JP5390599B2 (ja) | 2014-01-15 |
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| JP2011510550A Expired - Fee Related JP5390599B2 (ja) | 2008-05-22 | 2009-05-04 | エポキシ樹脂のアダクト及びその製造方法 |
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| US (1) | US20110040046A1 (https=) |
| EP (1) | EP2283060A1 (https=) |
| JP (1) | JP5390599B2 (https=) |
| CN (1) | CN102037049B (https=) |
| TW (1) | TW201002751A (https=) |
| WO (1) | WO2009142898A1 (https=) |
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| US20110054056A1 (en) * | 2008-05-22 | 2011-03-03 | Hefner Jr Robert E | Thermoset polyurethanes |
| CN102971282B (zh) | 2010-04-29 | 2015-11-25 | 陶氏环球技术有限责任公司 | 聚环戊二烯多酚和聚氰酸酯聚环戊二烯多酚化合物 |
| KR20130073906A (ko) | 2010-04-29 | 2013-07-03 | 다우 글로벌 테크놀로지스 엘엘씨 | 폴리시클로펜타디엔 폴리페놀의 폴리(알릴 에테르) |
| WO2011136845A1 (en) | 2010-04-29 | 2011-11-03 | Dow Global Technologies Llc | Vinylbenzyl ethers of polycyclopentadiene polyphenol |
| EP2621990B1 (en) | 2010-09-30 | 2016-02-24 | Blue Cube IP LLC | Thermosettable compositions and thermosets therefrom |
| EP2621998A1 (en) * | 2010-09-30 | 2013-08-07 | Dow Global Technologies LLC | Coating compositions |
| US20130178590A1 (en) * | 2010-09-30 | 2013-07-11 | Dow Global Technologies Llc | Advanced epoxy resin compositions |
| JP2013538918A (ja) * | 2010-09-30 | 2013-10-17 | ダウ グローバル テクノロジーズ エルエルシー | エポキシ樹脂アダクトおよびその熱硬化樹脂 |
| US8962792B2 (en) | 2010-09-30 | 2015-02-24 | Dow Global Technologies Llc | Process for preparing epoxy resins |
| JP5795804B2 (ja) | 2010-09-30 | 2015-10-14 | ダウ グローバル テクノロジーズ エルエルシー | コーティング組成物 |
| WO2012044443A1 (en) * | 2010-09-30 | 2012-04-05 | Dow Global Technologies Llc | Epoxy resin compositions |
| CN103781813B (zh) * | 2011-07-01 | 2016-09-14 | 蓝立方知识产权有限责任公司 | 混杂的环氧树脂加合物 |
| CN104334600A (zh) * | 2012-05-16 | 2015-02-04 | 株式会社大赛璐 | 固化性树脂组合物及其固化物、预浸料、以及纤维强化复合材料 |
| US20150165670A1 (en) * | 2012-07-03 | 2015-06-18 | 3M Innovative Properties Company | Method of making structured hybrid adhesive articles |
| KR20150079611A (ko) | 2012-10-24 | 2015-07-08 | 다우 글로벌 테크놀로지스 엘엘씨 | 부가물 경화제 |
| JP2016500743A (ja) * | 2012-10-24 | 2016-01-14 | ダウ グローバル テクノロジーズ エルエルシー | 耐候性コーティング |
| KR102129641B1 (ko) * | 2012-10-24 | 2020-07-02 | 블루 큐브 아이피 엘엘씨 | 상온 경화 내후성 코팅 |
| CN105229095A (zh) * | 2012-12-14 | 2016-01-06 | 蓝立方知识产权有限责任公司 | 高含固量环氧树脂涂料 |
| US9464224B2 (en) * | 2013-12-18 | 2016-10-11 | Rohm And Haas Electronic Materials Llc | Transformative wavelength conversion medium |
| JP6306419B2 (ja) * | 2014-04-28 | 2018-04-04 | 株式会社クラレ | モノグリシジルエーテル化合物、及びモノアリルエーテル化合物 |
| DE102016203867A1 (de) * | 2016-03-09 | 2017-09-14 | Siemens Aktiengesellschaft | Fester Isolationswerkstoff, Verwendung dazu und damit hergestelltes Isolationssystem |
| CN113045438A (zh) * | 2021-03-11 | 2021-06-29 | 深圳飞扬兴业科技有限公司 | 一种多元伯胺化合物及其制备方法和应用 |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3297724A (en) * | 1961-03-07 | 1967-01-10 | Eastman Kodak Co | Diepoxides |
| GB1053340A (https=) * | 1963-10-14 | 1900-01-01 | ||
| US4417033A (en) * | 1982-06-01 | 1983-11-22 | Wilmington Chemical Corporation | Diglycidyl ether of dimethanol cyclohexane and reaction products thereof |
| AU571499B2 (en) * | 1983-04-01 | 1988-04-21 | Dow Chemical Company, The | Preparing epoxy resins |
| US4578453A (en) * | 1984-11-23 | 1986-03-25 | Eastman Kodak Company | High molecular weight polyesters |
| US4623701A (en) * | 1985-07-10 | 1986-11-18 | The Dow Chemical Company | Multifunctional epoxy resins |
| US5300541A (en) * | 1988-02-04 | 1994-04-05 | Ppg Industries, Inc. | Polyamine-polyepoxide gas barrier coatings |
| US5463091A (en) * | 1989-01-17 | 1995-10-31 | The Dow Chemical Company | Diglycidyl ether of 4,4'-dihydroxy-α-methylstilbene |
| US5310770A (en) * | 1992-12-30 | 1994-05-10 | Hi-Tek Polymers, Inc. | Water reducible epoxy-amine adducts based on the diglycidyl ether of cyclohexane dimethanol |
| US6218482B1 (en) * | 1994-02-24 | 2001-04-17 | New Japan Chemical Co., Ltd. | Epoxy resin, process for preparing the resin and photo-curable resin composition and resin composition for powder coatings containing the epoxy resin |
| JP3663861B2 (ja) * | 1997-12-03 | 2005-06-22 | 三菱瓦斯化学株式会社 | 新規な樹脂用組成物 |
| CA2400474C (en) * | 2000-02-17 | 2008-12-02 | The Sherwin-Williams Company | Aqueous polymer dispersions |
| US6806314B2 (en) * | 2003-02-03 | 2004-10-19 | Ppg Industries Ohio, Inc. | Coating of Hydroxy-functional polymer(s), crosslinker, and 1,3- and 1,4-cyclohexane dimethanols |
| US6818293B1 (en) * | 2003-04-24 | 2004-11-16 | Eastman Chemical Company | Stabilized polyester fibers and films |
| US7425594B2 (en) * | 2005-11-23 | 2008-09-16 | Ppg Industries Ohio, Inc. | Copolymer of glycidyl ester and/or ether with polyol |
-
2009
- 2009-05-04 JP JP2011510550A patent/JP5390599B2/ja not_active Expired - Fee Related
- 2009-05-04 US US12/989,495 patent/US20110040046A1/en not_active Abandoned
- 2009-05-04 WO PCT/US2009/042643 patent/WO2009142898A1/en not_active Ceased
- 2009-05-04 EP EP09751127A patent/EP2283060A1/en not_active Withdrawn
- 2009-05-04 CN CN200980118516.3A patent/CN102037049B/zh not_active Expired - Fee Related
- 2009-05-21 TW TW098116880A patent/TW201002751A/zh unknown
Also Published As
| Publication number | Publication date |
|---|---|
| WO2009142898A1 (en) | 2009-11-26 |
| US20110040046A1 (en) | 2011-02-17 |
| EP2283060A1 (en) | 2011-02-16 |
| TW201002751A (en) | 2010-01-16 |
| CN102037049A (zh) | 2011-04-27 |
| JP2011521073A (ja) | 2011-07-21 |
| CN102037049B (zh) | 2014-09-03 |
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