ES2635083T3 - Materiales funcionales con reticulación reversible - Google Patents
Materiales funcionales con reticulación reversible Download PDFInfo
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- ES2635083T3 ES2635083T3 ES11700157.8T ES11700157T ES2635083T3 ES 2635083 T3 ES2635083 T3 ES 2635083T3 ES 11700157 T ES11700157 T ES 11700157T ES 2635083 T3 ES2635083 T3 ES 2635083T3
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Classifications
-
- 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
- C09J4/00—Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16
-
- 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
- C09J5/00—Adhesive processes in general; Adhesive processes not provided for elsewhere, e.g. relating to primers
-
- 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
- C09J2301/00—Additional features of adhesives in the form of films or foils
- C09J2301/50—Additional features of adhesives in the form of films or foils characterized by process specific features
- C09J2301/502—Additional features of adhesives in the form of films or foils characterized by process specific features process for debonding adherents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Sealing Material Composition (AREA)
- Other Resins Obtained By Reactions Not Involving Carbon-To-Carbon Unsaturated Bonds (AREA)
- Paints Or Removers (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102010001987 | 2010-02-16 | ||
| DE102010001987A DE102010001987A1 (de) | 2010-02-16 | 2010-02-16 | Funktionsmaterialien mit reversibler Vernetzung |
| PCT/EP2011/050043 WO2011101176A1 (de) | 2010-02-16 | 2011-01-04 | Funktionsmaterialien mit reversibler vernetzung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2635083T3 true ES2635083T3 (es) | 2017-10-02 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES11700157.8T Active ES2635083T3 (es) | 2010-02-16 | 2011-01-04 | Materiales funcionales con reticulación reversible |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US8916635B2 (https=) |
| EP (1) | EP2536797B1 (https=) |
| JP (1) | JP5855021B2 (https=) |
| CN (1) | CN102844391B (https=) |
| AU (1) | AU2011217504A1 (https=) |
| BR (1) | BR112012020564A2 (https=) |
| CA (1) | CA2789841C (https=) |
| DE (1) | DE102010001987A1 (https=) |
| DK (1) | DK2536797T3 (https=) |
| ES (1) | ES2635083T3 (https=) |
| PL (1) | PL2536797T3 (https=) |
| TW (1) | TWI519572B (https=) |
| WO (1) | WO2011101176A1 (https=) |
Families Citing this family (35)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102010001992A1 (de) | 2010-02-16 | 2011-08-18 | Evonik Röhm GmbH, 64293 | Funktionsmaterialien mit steuerbarer Viskosität |
| DE102010040282A1 (de) | 2010-09-06 | 2012-03-08 | Evonik Röhm Gmbh | Funktionsmaterialien mit steuerbarer Viskosität bzw. reversibler Vernetzung über Aza-Diels-Alder-Reaktionen mit Bishydrazonen oder konjugierten Bis-Schiff'schen Basen |
| DE102010044025A1 (de) | 2010-11-17 | 2012-05-24 | Evonik Röhm Gmbh | Materialien mit steuerbarem Vernetzungsgrad |
| MX2013007753A (es) | 2011-01-04 | 2013-08-15 | Evonik Degussa Gmbh | Productos semiterminados compuestos, partes moldeadas producidas por los mismos y partes moldeadas producidas directamente en base a (met) acrilatos hidroxifuncionalizados, los cuales son reticulados por medio de uretdionas en forma termoestable. |
| DE102011079812A1 (de) | 2011-07-26 | 2013-01-31 | Evonik Röhm Gmbh | Polymerpulver zur Herstellung dreidimensionaler Objekte |
| DE102011080131A1 (de) | 2011-07-29 | 2013-01-31 | Evonik Degussa Gmbh | Niedermolekulare Produkte, und deren Verwendung als reversible oder permanente Niedertemperatur-Vernetzer bei Diels-Alder-Reaktionen |
| DE102011086502A1 (de) * | 2011-11-16 | 2013-05-16 | Tesa Se | Verfahren zur Herstellung ungefärbter Polyacrylatklebemassen mit enger Molmassenverteilung |
| DE102011086503A1 (de) | 2011-11-16 | 2013-05-16 | Tesa Se | Verfahren zur Herstellung von kohäsiven Polyacrylatklebemassen mit enger Molmassenverteilung |
| DE102011087226A1 (de) * | 2011-11-28 | 2013-05-29 | Evonik Degussa Gmbh | Pseudo-thermoplastische, selbstvernetzende Composites |
| DE102012200235A1 (de) | 2012-01-10 | 2013-07-11 | Evonik Industries Ag | Photoinduzierte Vernetzung von Doppelbindungen-enthaltenden Polymeren mittels pericyclischer Reaktion |
| EP2740755A1 (en) * | 2012-12-07 | 2014-06-11 | Fonds de l'ESPCI - Georges Charpak | Processable semi-crystalline polymer networks |
| DE102012222742A1 (de) | 2012-12-11 | 2014-03-27 | Evonik Industries Ag | Funktionsmaterialien mit reversibler Vernetzung |
| JP5594352B2 (ja) * | 2012-12-13 | 2014-09-24 | 横浜ゴム株式会社 | 分子中に二重結合を有するゴム組成物 |
| US20160304683A1 (en) * | 2013-11-19 | 2016-10-20 | Evonik Degussa Gmbh | Mouldings based on diene-functionalized (meth)acrylates and (hetero-)diels-alder dienophiles, with reversible crosslinking |
| EP2982704A1 (de) | 2014-08-06 | 2016-02-10 | Evonik Degussa GmbH | Reversibel vernetzte Polymeremulsionen |
| EP2982503A1 (de) * | 2014-08-07 | 2016-02-10 | Evonik Röhm GmbH | Sandwich-Bauteile aus Poly(Meth)acrylat-basierten Schaumkörpern und reversibel vernetzbaren Composites |
| JP2016037571A (ja) * | 2014-08-08 | 2016-03-22 | Jsr株式会社 | 造形用樹脂組成物及び造形用フィラメント |
| CN107111225B (zh) | 2014-12-23 | 2021-07-27 | 普利司通美国轮胎运营有限责任公司 | 聚合物产品的增材制造方法 |
| EP3053905A1 (de) | 2015-02-04 | 2016-08-10 | Evonik Degussa GmbH | Durch sichtbares Licht induzierte Zykloaddition zur Polymerisation bzw. Vernetzung mittels Azirin-Verbindungen |
| US11097531B2 (en) | 2015-12-17 | 2021-08-24 | Bridgestone Americas Tire Operations, Llc | Additive manufacturing cartridges and processes for producing cured polymeric products by additive manufacturing |
| EP3181651B1 (fr) * | 2015-12-18 | 2019-02-06 | The Swatch Group Research and Development Ltd. | Ensemble de pièces horlogères assemblées par adhésif repositionnable à chaud et procédé d'assemblage et de repositionnement de telles pièces |
| EP3181652B1 (fr) * | 2015-12-18 | 2019-02-27 | The Swatch Group Research and Development Ltd. | Procédé d'assemblage et de repositionnement de pièces horlogères en utilisant un adhésif repositionnable à chaud |
| EP3199575A1 (de) | 2016-01-29 | 2017-08-02 | Evonik Degussa GmbH | Neuartiger hetero-diels-alder-vernetzer und deren verwendung in reversibel vernetzenden polymersystemen |
| CN105694790B (zh) * | 2016-02-29 | 2018-06-29 | 中国工程物理研究院材料研究所 | 一种可快速拆解的环氧胶粘剂及其制备和拆解方法 |
| DE102016104071B4 (de) | 2016-03-07 | 2018-10-25 | Groz-Beckert Kg | Verfahren zum Biegen eines Bewehrungsstabes eines Bewehrungselements sowie Biegevorrichtung |
| EP3296347A1 (de) | 2016-09-20 | 2018-03-21 | Evonik Degussa GmbH | Neuartiger dien-baustein für die verwendung in reversibel vernetzenden (hetero-)diels-alder-polymersystemen |
| WO2018054684A1 (de) | 2016-09-20 | 2018-03-29 | Evonik Degussa Gmbh | Neuartiger vernetzer-baustein für die verwendung in reversibel vernetzenden polymersystemen |
| US11453161B2 (en) | 2016-10-27 | 2022-09-27 | Bridgestone Americas Tire Operations, Llc | Processes for producing cured polymeric products by additive manufacturing |
| DE102017120143A1 (de) | 2017-09-01 | 2019-03-07 | Groz-Beckert Kg | Biegeverfahren und Biegevorrichtung zum Biegen eines Verbundwerkstoffstabes |
| DE102017120624A1 (de) | 2017-09-07 | 2019-03-07 | Groz-Beckert Kg | Textilbewehrungsanordnung, Verfahren zu dessen Herstellung sowie Trenn- und/oder Formgebungseinrichtung zur Verwendung bei diesem Verfahren |
| DE102017131236A1 (de) * | 2017-12-22 | 2019-06-27 | Bundesrepublik Deutschland, Vertreten Durch Den Bundesminister Für Wirtschaft Und Energie, Dieser Vertreten Durch Den Präsidenten Der Bundesanstalt Für Materialforschung Und -Prüfung (Bam) | Verfahren zur herstellung von klebflächen mittels einer 3d-druckvorrichtung |
| US20210230781A1 (en) * | 2018-06-08 | 2021-07-29 | Cummins Filtration Ip, Inc. | Cross-linked non-wovens produced by melt blowing reversible polymer networks |
| CN112778548B (zh) * | 2019-11-04 | 2022-10-21 | 中国石油化工股份有限公司 | 可逆交联的脂肪族聚酯及其制备方法 |
| US20230340194A1 (en) * | 2020-04-01 | 2023-10-26 | Idemitsu Kosan Co.,Ltd. | Resin, resin precursor composition, coating composition, electrophotographic photoreceptor, molded article, electronic device, and electrophotographic photoreceptor production method |
| WO2025090402A1 (en) * | 2023-10-23 | 2025-05-01 | Geisys Ventures, LLC | Debondable adhesive |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2001520660A (ja) | 1997-04-21 | 2001-10-30 | プロリゴ・エルエルシー | オリゴヌクレオチドの溶液相合成方法 |
| JP4031866B2 (ja) * | 1998-06-16 | 2008-01-09 | 横浜ゴム株式会社 | リサイクル性エラストマー |
| DE19832629A1 (de) | 1998-07-21 | 2000-02-03 | Daimler Chrysler Ag | Klebstoffsystem zur Bildung reversibler Klebeverbindungen |
| DE19961940A1 (de) | 1999-12-22 | 2001-08-02 | Henkel Kgaa | Lösbare Klebeverindungen |
| US6933361B2 (en) | 2002-07-12 | 2005-08-23 | The Regents Of The University Of California | Thermally re-mendable cross-linked polymers |
| US7309754B2 (en) * | 2003-09-26 | 2007-12-18 | Hitachi Global Storage Technologies Netherlands B.V. | Stable encapsulant fluid capable of undergoing reversible Diels-Alder polymerization |
| US20050159521A1 (en) | 2004-01-20 | 2005-07-21 | Brown Donald A. | Reversible adhesive |
| JP2006193628A (ja) * | 2005-01-14 | 2006-07-27 | Yokohama Rubber Co Ltd:The | 共役ジエン化合物、硬化性組成物およびその硬化物 |
| US8685528B2 (en) | 2007-04-20 | 2014-04-01 | GM Global Technology Operations LLC | Shape memory polymer and adhesive combination and methods of making and using the same |
| US7976665B2 (en) | 2007-10-04 | 2011-07-12 | GM Global Technology Operations LLC | Method of minimizing residue adhesion for thermo-reversible dry adhesives |
| EP2062926A1 (de) | 2007-11-21 | 2009-05-27 | Sika Technology AG | Polyurethanpolymer für reversible Klebeverbindungen |
| EP2166030A1 (en) * | 2008-09-19 | 2010-03-24 | Rijksuniversiteit Groningen | Re-mouldable cross-linked resin, a composition, a substituted furan, and processes for preparing the same |
| KR20120029421A (ko) * | 2009-06-11 | 2012-03-26 | 헨켈 코포레이션 | 다관능성 디엔 및 친디엔체 화합물을 함유하는 열 가역성 핫 멜트 접착제 조성물 |
| DE102010040282A1 (de) | 2010-09-06 | 2012-03-08 | Evonik Röhm Gmbh | Funktionsmaterialien mit steuerbarer Viskosität bzw. reversibler Vernetzung über Aza-Diels-Alder-Reaktionen mit Bishydrazonen oder konjugierten Bis-Schiff'schen Basen |
| DE102010044025A1 (de) | 2010-11-17 | 2012-05-24 | Evonik Röhm Gmbh | Materialien mit steuerbarem Vernetzungsgrad |
| MX2013007753A (es) | 2011-01-04 | 2013-08-15 | Evonik Degussa Gmbh | Productos semiterminados compuestos, partes moldeadas producidas por los mismos y partes moldeadas producidas directamente en base a (met) acrilatos hidroxifuncionalizados, los cuales son reticulados por medio de uretdionas en forma termoestable. |
| DE102011080131A1 (de) | 2011-07-29 | 2013-01-31 | Evonik Degussa Gmbh | Niedermolekulare Produkte, und deren Verwendung als reversible oder permanente Niedertemperatur-Vernetzer bei Diels-Alder-Reaktionen |
-
2010
- 2010-02-16 DE DE102010001987A patent/DE102010001987A1/de not_active Withdrawn
-
2011
- 2011-01-04 ES ES11700157.8T patent/ES2635083T3/es active Active
- 2011-01-04 CA CA2789841A patent/CA2789841C/en not_active Expired - Fee Related
- 2011-01-04 EP EP11700157.8A patent/EP2536797B1/de not_active Not-in-force
- 2011-01-04 CN CN201180007005.1A patent/CN102844391B/zh not_active Expired - Fee Related
- 2011-01-04 AU AU2011217504A patent/AU2011217504A1/en not_active Abandoned
- 2011-01-04 DK DK11700157.8T patent/DK2536797T3/en active
- 2011-01-04 JP JP2012553236A patent/JP5855021B2/ja not_active Expired - Fee Related
- 2011-01-04 WO PCT/EP2011/050043 patent/WO2011101176A1/de not_active Ceased
- 2011-01-04 PL PL11700157T patent/PL2536797T3/pl unknown
- 2011-01-04 BR BR112012020564A patent/BR112012020564A2/pt not_active Application Discontinuation
- 2011-01-04 US US13/577,932 patent/US8916635B2/en not_active Expired - Fee Related
- 2011-02-14 TW TW100104752A patent/TWI519572B/zh not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| TWI519572B (zh) | 2016-02-01 |
| JP5855021B2 (ja) | 2016-02-09 |
| EP2536797A1 (de) | 2012-12-26 |
| WO2011101176A1 (de) | 2011-08-25 |
| CA2789841C (en) | 2017-07-11 |
| BR112012020564A2 (pt) | 2016-07-19 |
| PL2536797T3 (pl) | 2018-01-31 |
| CA2789841A1 (en) | 2011-08-25 |
| DK2536797T3 (en) | 2017-10-16 |
| CN102844391B (zh) | 2015-04-22 |
| AU2011217504A1 (en) | 2012-07-12 |
| TW201141919A (en) | 2011-12-01 |
| DE102010001987A1 (de) | 2011-08-18 |
| WO2011101176A9 (de) | 2012-08-16 |
| JP2013519764A (ja) | 2013-05-30 |
| US8916635B2 (en) | 2014-12-23 |
| EP2536797B1 (de) | 2017-06-21 |
| CN102844391A (zh) | 2012-12-26 |
| US20120309895A1 (en) | 2012-12-06 |
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