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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- YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 1
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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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- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
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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
- C08G59/182—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 |
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| 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 |
| CN102947261A (zh) | 2010-04-29 | 2013-02-27 | 陶氏环球技术有限责任公司 | 聚环戊二烯多酚的聚(烯丙基醚) |
| EP2563755A1 (en) | 2010-04-29 | 2013-03-06 | Dow Global Technologies LLC | Vinylbenzyl ethers of polycyclopentadiene polyphenol |
| CN105175988A (zh) | 2010-04-29 | 2015-12-23 | 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 |
| KR101840073B1 (ko) | 2010-09-30 | 2018-04-26 | 블루 큐브 아이피 엘엘씨 | 에폭시 수지의 제조 방법 |
| US9068039B2 (en) | 2010-09-30 | 2015-06-30 | Dow Global Technologies Llc | Thermosettable compositions and thermosets therefrom |
| CN103154071B (zh) * | 2010-09-30 | 2016-06-15 | 蓝立方知识产权有限责任公司 | 涂料组合物 |
| EP2621994A1 (en) * | 2010-09-30 | 2013-08-07 | Dow Global Technologies LLC | Epoxy resin compositions |
| WO2012050688A2 (en) | 2010-09-30 | 2012-04-19 | Dow Global Technologies Llc | Epoxy resin adducts and thermosets thereof |
| JP2013539804A (ja) * | 2010-09-30 | 2013-10-28 | ダウ グローバル テクノロジーズ エルエルシー | アドバンストエポキシ樹脂組成物 |
| BR112013005067A2 (pt) | 2010-09-30 | 2019-09-24 | Dow Global Technologies Llc | composição de revestimento curável,revestimento curado,processo para preparar um artigo revestido e artigo |
| BR112013033451A2 (pt) * | 2011-07-01 | 2017-01-31 | Dow Global Technologies Llc | aduto de resina epoxi híbrida, processo para preparar um aduto de resina epoxi híbrida, composição de resina epoxi curável, processo para preparar uma composição de resina epoxi curável, produto termofixo de estágio b, processo de estagiamento b de uma resina epoxi, produto termofixo curado, processo para curar uma composição de resina epoxi e artigo |
| WO2013172199A1 (ja) * | 2012-05-16 | 2013-11-21 | 株式会社ダイセル | 硬化性樹脂組成物及びその硬化物、プリプレグ、並びに繊維強化複合材料 |
| JP6130502B2 (ja) * | 2012-07-03 | 2017-05-17 | スリーエム イノベイティブ プロパティズ カンパニー | 構造化ハイブリッド接着剤物品の製造方法 |
| JP2016500744A (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 | 常温硬化耐候性コーティング |
| KR20150079620A (ko) * | 2012-10-24 | 2015-07-08 | 다우 글로벌 테크놀로지스 엘엘씨 | 내후성 코팅 |
| KR20150079611A (ko) | 2012-10-24 | 2015-07-08 | 다우 글로벌 테크놀로지스 엘엘씨 | 부가물 경화제 |
| 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 |
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| 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 |
| US7129278B2 (en) * | 2000-02-17 | 2006-10-31 | 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 WO PCT/US2009/042643 patent/WO2009142898A1/en not_active Ceased
- 2009-05-04 CN CN200980118516.3A patent/CN102037049B/zh not_active Expired - Fee Related
- 2009-05-04 EP EP09751127A patent/EP2283060A1/en not_active Withdrawn
- 2009-05-04 US US12/989,495 patent/US20110040046A1/en not_active Abandoned
- 2009-05-21 TW TW098116880A patent/TW201002751A/zh unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP2283060A1 (en) | 2011-02-16 |
| TW201002751A (en) | 2010-01-16 |
| WO2009142898A1 (en) | 2009-11-26 |
| CN102037049A (zh) | 2011-04-27 |
| JP2011521073A (ja) | 2011-07-21 |
| CN102037049B (zh) | 2014-09-03 |
| US20110040046A1 (en) | 2011-02-17 |
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