CN104144963B - 具有改进的反应性的源自生物的环氧树脂 - Google Patents
具有改进的反应性的源自生物的环氧树脂 Download PDFInfo
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- CN104144963B CN104144963B CN201380010198.5A CN201380010198A CN104144963B CN 104144963 B CN104144963 B CN 104144963B CN 201380010198 A CN201380010198 A CN 201380010198A CN 104144963 B CN104144963 B CN 104144963B
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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
- C08G59/02—Polycondensates containing more than one epoxy group per molecule
- C08G59/027—Polycondensates containing more than one epoxy group per molecule obtained by epoxidation of unsaturated precursor, e.g. polymer or monomer
-
- 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
- C08G59/14—Polycondensates modified by chemical after-treatment
- C08G59/1433—Polycondensates modified by chemical after-treatment with organic low-molecular-weight compounds
- C08G59/1438—Polycondensates modified by chemical after-treatment with organic low-molecular-weight compounds containing oxygen
-
- 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
- C08G59/40—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 curing agents used
- C08G59/50—Amines
- C08G59/5026—Amines cycloaliphatic
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J163/00—Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins
- C09J163/10—Epoxy resins modified by unsaturated compounds
-
- 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
- C08G2150/00—Compositions for coatings
-
- 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
- C08G2170/00—Compositions for adhesives
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Emergency Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Epoxy Resins (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR1251539 | 2012-02-20 | ||
| FR1251539A FR2987049B1 (fr) | 2012-02-20 | 2012-02-20 | Resines epoxydes biosourcees a reactivite amelioree. |
| PCT/FR2013/050331 WO2013124574A2 (fr) | 2012-02-20 | 2013-02-18 | Resines epoxydes biosourcees a reactivite amelioree |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN104144963A CN104144963A (zh) | 2014-11-12 |
| CN104144963B true CN104144963B (zh) | 2016-10-26 |
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| Application Number | Title | Priority Date | Filing Date |
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| CN201380010198.5A Expired - Fee Related CN104144963B (zh) | 2012-02-20 | 2013-02-18 | 具有改进的反应性的源自生物的环氧树脂 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US20150011680A1 (enExample) |
| EP (1) | EP2817348A2 (enExample) |
| JP (1) | JP2015508122A (enExample) |
| CN (1) | CN104144963B (enExample) |
| FR (1) | FR2987049B1 (enExample) |
| WO (1) | WO2013124574A2 (enExample) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2997401B1 (fr) * | 2012-10-25 | 2016-01-29 | Univ Montpellier Ii | Resines epoxydes reticulables a temperature ambiante |
| FR3024981B1 (fr) | 2014-08-22 | 2016-09-09 | Univ Montpellier 2 Sciences Et Techniques | Derives polyesters d'acides gras de polyglycosides |
| FR3025203B1 (fr) * | 2014-08-26 | 2016-12-09 | Renfortech | Mousses epoxy derivees de formulations reactives biosourcees |
| US10428175B2 (en) | 2014-09-12 | 2019-10-01 | Drexel University | Toughening of epoxy thermosets |
| US9828508B2 (en) * | 2015-04-21 | 2017-11-28 | The United States Of America, As Represented By The Secretary Of The Navy | Rapid cure polysulfide coatings for cavitation resistance, erosion resistance, and sound damping |
| CN104892858B (zh) * | 2015-05-13 | 2017-11-07 | 中国科学院宁波材料技术与工程研究所 | 一种高生物基含量环氧树脂组合物及其固化方法和应用 |
| MY195345A (en) * | 2016-06-15 | 2023-01-13 | Steed Mifsud Pty Ltd | Glycerol-Based Epoxy Resins |
| CN109021902B (zh) * | 2018-07-02 | 2021-03-19 | 扬州市文祺材料有限公司 | 一种生物基可降解环氧树脂胶黏剂及其制备方法 |
| CN108715631B (zh) * | 2018-07-02 | 2020-05-26 | 扬州市文祺材料有限公司 | 一种木糖醇基多官环氧树脂及其制备方法 |
| CN113667434B (zh) * | 2021-07-29 | 2023-02-28 | 北京林业大学 | 一种基于巯基-环氧反应的胶黏剂及其制备方法与应用 |
| JP2023177577A (ja) * | 2022-06-02 | 2023-12-14 | 住友化学株式会社 | 非対称ジアミンを含む剤及び樹脂並びにその使用 |
| CN115433342B (zh) * | 2022-10-08 | 2023-11-14 | 南京先进生物材料与过程装备研究院有限公司 | 一种基于山梨醇缩水甘油醚的生物基环氧树脂及其制备方法 |
| WO2025070358A1 (ja) * | 2023-09-25 | 2025-04-03 | ナガセケムテックス株式会社 | 接着剤 |
| WO2025203281A1 (ja) * | 2024-03-26 | 2025-10-02 | 本田技研工業株式会社 | 高分子樹脂組成物、及びその製造方法 |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3351574A (en) * | 1965-02-24 | 1967-11-07 | Celanese Coatings Co | Castor oil polyglycidyl ether |
| CN1122145A (zh) * | 1993-03-30 | 1996-05-08 | 国际壳牌研究有限公司 | 环氧化植物油改性的环氧酯 |
| DE19914183C2 (de) * | 1999-03-29 | 2001-03-15 | Dlw Ag | Polyreaktionsprodukte enthaltende Materialien auf Basis nachwachsender Rohstoffe, Verfahren zur Herstellung und Flächengebilde |
| CN1656169A (zh) * | 2002-04-25 | 2005-08-17 | 阿什兰公司 | 用于增强型复合材料组合物的表面改进剂 |
| DE102005046642A1 (de) * | 2005-09-29 | 2007-04-05 | Goldschmidt Gmbh | Verfahren zum Schutz von Metalloberflächen gegen Korrosion in sauergashaltigen Medien |
| CN102144265A (zh) * | 2008-09-02 | 2011-08-03 | 株式会社明电舍 | 绝缘性高分子材料组合物 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4962179A (en) * | 1989-08-31 | 1990-10-09 | Shell Oil Company | Epoxidized fatty acid ester compositions |
| US5728779A (en) * | 1992-12-01 | 1998-03-17 | Dsm N.V. | Powder paint of epoxy-reactive polymer and aliphatic chain-containing polyepoxide |
| DE4410785A1 (de) * | 1994-03-28 | 1995-10-05 | Hoechst Ag | Amin-modifizierte Epoxidharz-Zusammensetzung |
| US5569733A (en) * | 1994-03-31 | 1996-10-29 | Ppg Industries, Inc. | Tertiary aminourea compositions and their use as catalysts in curable compositions |
| US6194490B1 (en) * | 1998-02-27 | 2001-02-27 | Vantico, Inc. | Curable composition comprising epoxidized natural oils |
| DE10224275B4 (de) * | 2002-05-31 | 2007-08-02 | Clariant Produkte (Deutschland) Gmbh | Emulsionsspalter |
| JP2004059812A (ja) * | 2002-07-30 | 2004-02-26 | Dainichiseika Color & Chem Mfg Co Ltd | コーティング剤組成物 |
| US7619056B2 (en) * | 2006-06-02 | 2009-11-17 | New Jersey Institute Of Technology | Thermoset epoxy polymers from renewable resources |
| WO2008147473A1 (en) * | 2007-05-31 | 2008-12-04 | New Jersey Institute Of Technology | Thermoset epoxy polymers from renewable resources |
| FR2946049B1 (fr) | 2009-05-27 | 2013-01-18 | Chaire Europ De Chimie Nouvelle Pour Un Dev Durable | Compose phenoliques naturels et leur mode d'activation pour la formulation de resines thermodurcissables |
| JP5437929B2 (ja) * | 2010-06-24 | 2014-03-12 | パナソニック株式会社 | エポキシ樹脂組成物とそれを用いた成形品 |
-
2012
- 2012-02-20 FR FR1251539A patent/FR2987049B1/fr not_active Expired - Fee Related
-
2013
- 2013-02-18 CN CN201380010198.5A patent/CN104144963B/zh not_active Expired - Fee Related
- 2013-02-18 WO PCT/FR2013/050331 patent/WO2013124574A2/fr not_active Ceased
- 2013-02-18 EP EP13710476.6A patent/EP2817348A2/fr not_active Withdrawn
- 2013-02-18 US US14/379,582 patent/US20150011680A1/en not_active Abandoned
- 2013-02-18 JP JP2014558180A patent/JP2015508122A/ja active Pending
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3351574A (en) * | 1965-02-24 | 1967-11-07 | Celanese Coatings Co | Castor oil polyglycidyl ether |
| CN1122145A (zh) * | 1993-03-30 | 1996-05-08 | 国际壳牌研究有限公司 | 环氧化植物油改性的环氧酯 |
| DE19914183C2 (de) * | 1999-03-29 | 2001-03-15 | Dlw Ag | Polyreaktionsprodukte enthaltende Materialien auf Basis nachwachsender Rohstoffe, Verfahren zur Herstellung und Flächengebilde |
| CN1656169A (zh) * | 2002-04-25 | 2005-08-17 | 阿什兰公司 | 用于增强型复合材料组合物的表面改进剂 |
| DE102005046642A1 (de) * | 2005-09-29 | 2007-04-05 | Goldschmidt Gmbh | Verfahren zum Schutz von Metalloberflächen gegen Korrosion in sauergashaltigen Medien |
| CN102144265A (zh) * | 2008-09-02 | 2011-08-03 | 株式会社明电舍 | 绝缘性高分子材料组合物 |
Non-Patent Citations (1)
| Title |
|---|
| 植物油合成聚合物的研究进展;司徒粤等;《精细化工》;20061130;第23卷(第11期);正文第1041页右栏第1段,第1042页右栏第7段,第1044段右栏第3段,第1045段左栏第4段 * |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2013124574A2 (fr) | 2013-08-29 |
| US20150011680A1 (en) | 2015-01-08 |
| CN104144963A (zh) | 2014-11-12 |
| EP2817348A2 (fr) | 2014-12-31 |
| FR2987049A1 (fr) | 2013-08-23 |
| WO2013124574A3 (fr) | 2014-07-03 |
| JP2015508122A (ja) | 2015-03-16 |
| FR2987049B1 (fr) | 2014-03-07 |
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