JP2011521078A - 種油系アルカノールアミドから誘導されたエポキシ樹脂及びその製造方法 - Google Patents
種油系アルカノールアミドから誘導されたエポキシ樹脂及びその製造方法 Download PDFInfo
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- JP2011521078A JP2011521078A JP2011510607A JP2011510607A JP2011521078A JP 2011521078 A JP2011521078 A JP 2011521078A JP 2011510607 A JP2011510607 A JP 2011510607A JP 2011510607 A JP2011510607 A JP 2011510607A JP 2011521078 A JP2011521078 A JP 2011521078A
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- Prior art keywords
- epoxy resin
- amide
- fatty acid
- epoxy
- ether
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- -1 epoxide amide Chemical class 0.000 claims abstract description 216
- 239000000203 mixture Substances 0.000 claims abstract description 116
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 87
- 239000000194 fatty acid Substances 0.000 claims abstract description 87
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- 238000006243 chemical reaction Methods 0.000 claims abstract description 84
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- 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 44
- 239000003054 catalyst Substances 0.000 claims abstract description 42
- 150000001408 amides Chemical class 0.000 claims abstract description 32
- 239000004593 Epoxy Substances 0.000 claims abstract description 31
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 242
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- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 11
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- 239000000126 substance Substances 0.000 claims description 10
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- 239000002131 composite material Substances 0.000 claims description 6
- 125000000743 hydrocarbylene group Chemical group 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- AFEQENGXSMURHA-UHFFFAOYSA-N oxiran-2-ylmethanamine Chemical compound NCC1CO1 AFEQENGXSMURHA-UHFFFAOYSA-N 0.000 claims description 6
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- WISUILQECWFZCN-UHFFFAOYSA-N 2-(oxiran-2-ylmethylsulfanylmethyl)oxirane Chemical compound C1OC1CSCC1CO1 WISUILQECWFZCN-UHFFFAOYSA-N 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
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- 229920005862 polyol Polymers 0.000 description 126
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 69
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 66
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 66
- 239000011521 glass Substances 0.000 description 64
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- 239000000543 intermediate Substances 0.000 description 56
- 239000000376 reactant Substances 0.000 description 55
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 52
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 52
- 230000002829 reductive effect Effects 0.000 description 52
- 239000003549 soybean oil Substances 0.000 description 52
- 235000012424 soybean oil Nutrition 0.000 description 52
- 150000003077 polyols Chemical class 0.000 description 51
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 48
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 48
- 239000007788 liquid Substances 0.000 description 46
- 238000002390 rotary evaporation Methods 0.000 description 45
- 238000004128 high performance liquid chromatography Methods 0.000 description 44
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- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 40
- 239000000706 filtrate Substances 0.000 description 40
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- 238000002835 absorbance Methods 0.000 description 33
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- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 28
- 239000010410 layer Substances 0.000 description 28
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- 238000002798 spectrophotometry method Methods 0.000 description 22
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 21
- 150000002170 ethers Chemical class 0.000 description 21
- 125000003118 aryl group Chemical group 0.000 description 20
- 150000001875 compounds Chemical class 0.000 description 19
- 239000010408 film Substances 0.000 description 18
- 230000015572 biosynthetic process Effects 0.000 description 17
- 230000035484 reaction time Effects 0.000 description 17
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 16
- 238000009835 boiling Methods 0.000 description 16
- 238000004821 distillation Methods 0.000 description 16
- 238000003756 stirring Methods 0.000 description 16
- 239000010409 thin film Substances 0.000 description 16
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
- 239000003085 diluting agent Substances 0.000 description 15
- 239000008187 granular material Substances 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 14
- 238000004817 gas chromatography Methods 0.000 description 14
- 239000008188 pellet Substances 0.000 description 14
- 239000003153 chemical reaction reagent Substances 0.000 description 13
- 238000003786 synthesis reaction Methods 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 12
- 125000003700 epoxy group Chemical group 0.000 description 12
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- 229920006362 Teflon® Polymers 0.000 description 11
- 238000004458 analytical method Methods 0.000 description 11
- 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 11
- 238000005119 centrifugation Methods 0.000 description 11
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- 229920005989 resin Polymers 0.000 description 11
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- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 10
- AOMUHOFOVNGZAN-UHFFFAOYSA-N N,N-bis(2-hydroxyethyl)dodecanamide Chemical compound CCCCCCCCCCCC(=O)N(CCO)CCO AOMUHOFOVNGZAN-UHFFFAOYSA-N 0.000 description 10
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- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
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- 150000001721 carbon Chemical group 0.000 description 3
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- RBTVSNLYYIMMKS-UHFFFAOYSA-N tert-butyl 3-aminoazetidine-1-carboxylate;hydrochloride Chemical compound Cl.CC(C)(C)OC(=O)N1CC(N)C1 RBTVSNLYYIMMKS-UHFFFAOYSA-N 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- RKHXQBLJXBGEKF-UHFFFAOYSA-M tetrabutylphosphanium;bromide Chemical compound [Br-].CCCC[P+](CCCC)(CCCC)CCCC RKHXQBLJXBGEKF-UHFFFAOYSA-M 0.000 description 1
- IBWGNZVCJVLSHB-UHFFFAOYSA-M tetrabutylphosphanium;chloride Chemical compound [Cl-].CCCC[P+](CCCC)(CCCC)CCCC IBWGNZVCJVLSHB-UHFFFAOYSA-M 0.000 description 1
- CCIYPTIBRAUPLQ-UHFFFAOYSA-M tetrabutylphosphanium;iodide Chemical compound [I-].CCCC[P+](CCCC)(CCCC)CCCC CCIYPTIBRAUPLQ-UHFFFAOYSA-M 0.000 description 1
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- DDFYFBUWEBINLX-UHFFFAOYSA-M tetramethylammonium bromide Chemical compound [Br-].C[N+](C)(C)C DDFYFBUWEBINLX-UHFFFAOYSA-M 0.000 description 1
- QBVXKDJEZKEASM-UHFFFAOYSA-M tetraoctylammonium bromide Chemical compound [Br-].CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)CCCCCCCC QBVXKDJEZKEASM-UHFFFAOYSA-M 0.000 description 1
- SNNIPOQLGBPXPS-UHFFFAOYSA-M tetraoctylazanium;chloride Chemical compound [Cl-].CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)CCCCCCCC SNNIPOQLGBPXPS-UHFFFAOYSA-M 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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- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
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- CHJMFFKHPHCQIJ-UHFFFAOYSA-L zinc;octanoate Chemical compound [Zn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O CHJMFFKHPHCQIJ-UHFFFAOYSA-L 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D163/00—Coating compositions based on epoxy resins; Coating compositions based on derivatives of epoxy resins
-
- 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
- C08G59/20—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 epoxy compounds used
- C08G59/22—Di-epoxy compounds
- C08G59/28—Di-epoxy compounds containing acyclic nitrogen atoms
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Epoxy Resins (AREA)
- Epoxy Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US5524008P | 2008-05-22 | 2008-05-22 | |
| US61/055,240 | 2008-05-22 | ||
| PCT/US2009/044288 WO2009143036A1 (en) | 2008-05-22 | 2009-05-18 | Epoxy resins derived from seed oil based alkanolamides and a process for preparing the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2011521078A true JP2011521078A (ja) | 2011-07-21 |
| JP2011521078A5 JP2011521078A5 (enExample) | 2012-05-17 |
Family
ID=40943850
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011510607A Pending JP2011521078A (ja) | 2008-05-22 | 2009-05-18 | 種油系アルカノールアミドから誘導されたエポキシ樹脂及びその製造方法 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US20110060076A1 (enExample) |
| EP (1) | EP2283058A1 (enExample) |
| JP (1) | JP2011521078A (enExample) |
| CN (1) | CN102037046A (enExample) |
| WO (1) | WO2009143036A1 (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2011521080A (ja) * | 2008-05-22 | 2011-07-21 | ダウ グローバル テクノロジーズ エルエルシー | アルカノールアミドに由来するエポキシ樹脂の付加物及びその製造方法 |
| KR20190013726A (ko) * | 2016-04-01 | 2019-02-11 | 닥터 나이틀링거 홀딩 게엠베하 | 열 경화된 2-성분 에폭시드 수지 |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9732181B2 (en) | 2015-12-09 | 2017-08-15 | International Business Machines Corporation | Polyurethane materials formed from unsaturated plant oils via an alkyne zipper reaction |
| US9657130B1 (en) | 2015-12-10 | 2017-05-23 | International Business Machines Corporation | Polyurethane materials formed from unsaturated plant oils via an alkyne zipper reaction |
| US10392580B1 (en) * | 2016-03-14 | 2019-08-27 | Rust-Oleum Corporation | Seed oil based reactive diluent |
| US10287236B2 (en) * | 2016-04-18 | 2019-05-14 | University Of South Carolina | Preparation of thermoplastic epoxidized polymers and thermosetting materials from triglycerides |
| CN111440293B (zh) * | 2020-04-08 | 2022-11-18 | 西南林业大学 | 一种光催化环氧油脂选择性酯基胺解的方法 |
| CN115259511B (zh) * | 2022-06-08 | 2023-10-10 | 聊城市鲁西化工工程设计有限责任公司 | 一种多元醇酮残渣回收利用系统及方法 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH04500386A (ja) * | 1989-06-29 | 1992-01-23 | ドクトル フリッシェ ゲーエムベーハー | 脂肪酸ベースの新しいプラスチック |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3351574A (en) * | 1965-02-24 | 1967-11-07 | Celanese Coatings Co | Castor oil polyglycidyl ether |
| CH520725A (de) * | 1969-12-24 | 1972-03-31 | Reichhold Albert Chemie Ag | Verfahren zur Herstellung von wasserverdünnbaren, vinylmodifizierten Kunstharzen auf der Grundlage von Polyäthern |
| US4499255B1 (en) * | 1982-09-13 | 2000-01-11 | Dow Chemical Co | Preparation of epoxy resins |
| US4786666A (en) * | 1987-11-18 | 1988-11-22 | Interez, Inc. | Epoxy compositions containing glycidyl ethers of fatty esters |
| US5463091A (en) * | 1989-01-17 | 1995-10-31 | The Dow Chemical Company | Diglycidyl ether of 4,4'-dihydroxy-α-methylstilbene |
| US6194490B1 (en) * | 1998-02-27 | 2001-02-27 | Vantico, Inc. | Curable composition comprising epoxidized natural oils |
| US7300986B2 (en) * | 2001-10-12 | 2007-11-27 | Dow3Global Technologies Inc. | Polyepoxy compounds having an amide linkage |
| CN101172952B (zh) * | 2002-04-29 | 2013-03-27 | 陶氏环球技术有限责任公司 | 关于种子油工业应用的综合化学方法 |
| EA012871B1 (ru) * | 2002-05-31 | 2009-12-30 | Грейс Гмбх Унд Ко. Кг | Матирующее вещество для порошкового покрытия, включающее сложный эфирамидный продукт конденсации |
| CA2509087C (en) * | 2003-01-08 | 2013-03-12 | Texas Tech University | Castor oil/epoxidized soybean oil based elastomeric compositions |
| WO2005019297A1 (en) * | 2003-08-12 | 2005-03-03 | Dow Global Technologies Inc. | Curable compositions of acyl epoxides, cycloaliphatic epoxides, and aryl polyols, and network polymers therefrom |
| US7696370B2 (en) * | 2006-05-09 | 2010-04-13 | The Curators Of The University Of Missouri | Soy based polyols |
| BRPI0711689A2 (pt) * | 2006-06-23 | 2011-12-20 | Dow Global Technologies Inc | processo para produzir um epóxido a partir de uma olefina, processo para preparar uma composição de resina epóxi curável, composição de resina epóxi curável, resina epóxi curada, composição e revestimento com tenacidade melhorada |
| WO2008088624A2 (en) * | 2007-01-12 | 2008-07-24 | Dow Global Technologies Inc. | Hydroxyl-terminated or carboxylic acid- terminated reactive monomer compositions, their preparation and their use |
-
2009
- 2009-05-18 JP JP2011510607A patent/JP2011521078A/ja active Pending
- 2009-05-18 EP EP09751265A patent/EP2283058A1/en not_active Withdrawn
- 2009-05-18 CN CN2009801186058A patent/CN102037046A/zh active Pending
- 2009-05-18 WO PCT/US2009/044288 patent/WO2009143036A1/en not_active Ceased
- 2009-05-18 US US12/988,819 patent/US20110060076A1/en not_active Abandoned
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH04500386A (ja) * | 1989-06-29 | 1992-01-23 | ドクトル フリッシェ ゲーエムベーハー | 脂肪酸ベースの新しいプラスチック |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2011521080A (ja) * | 2008-05-22 | 2011-07-21 | ダウ グローバル テクノロジーズ エルエルシー | アルカノールアミドに由来するエポキシ樹脂の付加物及びその製造方法 |
| KR20190013726A (ko) * | 2016-04-01 | 2019-02-11 | 닥터 나이틀링거 홀딩 게엠베하 | 열 경화된 2-성분 에폭시드 수지 |
| KR102220274B1 (ko) | 2016-04-01 | 2021-02-24 | 닥터 나이틀링거 홀딩 게엠베하 | 열 경화된 2-성분 에폭시드 수지 |
Also Published As
| Publication number | Publication date |
|---|---|
| US20110060076A1 (en) | 2011-03-10 |
| EP2283058A1 (en) | 2011-02-16 |
| CN102037046A (zh) | 2011-04-27 |
| WO2009143036A1 (en) | 2009-11-26 |
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