JP5990591B2 - 触媒組成物およびニトリルゴムの水素化のためのそれらの使用 - Google Patents
触媒組成物およびニトリルゴムの水素化のためのそれらの使用 Download PDFInfo
- Publication number
- JP5990591B2 JP5990591B2 JP2014536269A JP2014536269A JP5990591B2 JP 5990591 B2 JP5990591 B2 JP 5990591B2 JP 2014536269 A JP2014536269 A JP 2014536269A JP 2014536269 A JP2014536269 A JP 2014536269A JP 5990591 B2 JP5990591 B2 JP 5990591B2
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- alkyl
- aryl
- heteroaryl
- catalyst
- alkynyl
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- 0 CC1N(C)C(C)N(*)C1* Chemical compound CC1N(C)C(C)N(*)C1* 0.000 description 4
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/22—Organic complexes
- B01J31/2282—Unsaturated compounds used as ligands
- B01J31/2295—Cyclic compounds, e.g. cyclopentadienyls
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0201—Oxygen-containing compounds
- B01J31/0204—Ethers
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
- B01J31/1805—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing nitrogen
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/22—Organic complexes
- B01J31/2204—Organic complexes the ligands containing oxygen or sulfur as complexing atoms
- B01J31/2208—Oxygen, e.g. acetylacetonates
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/22—Organic complexes
- B01J31/2265—Carbenes or carbynes, i.e.(image)
- B01J31/2269—Heterocyclic carbenes
- B01J31/2273—Heterocyclic carbenes with only nitrogen as heteroatomic ring members, e.g. 1,3-diarylimidazoline-2-ylidenes
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/22—Organic complexes
- B01J31/2265—Carbenes or carbynes, i.e.(image)
- B01J31/2278—Complexes comprising two carbene ligands differing from each other, e.g. Grubbs second generation catalysts
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
- B01J31/2404—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08C—TREATMENT OR CHEMICAL MODIFICATION OF RUBBERS
- C08C19/00—Chemical modification of rubber
- C08C19/02—Hydrogenation
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/50—Redistribution or isomerisation reactions of C-C, C=C or C-C triple bonds
- B01J2231/54—Metathesis reactions, e.g. olefin metathesis
- B01J2231/543—Metathesis reactions, e.g. olefin metathesis alkene metathesis
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/60—Reduction reactions, e.g. hydrogenation
- B01J2231/64—Reductions in general of organic substrates, e.g. hydride reductions or hydrogenations
- B01J2231/641—Hydrogenation of organic substrates, i.e. H2 or H-transfer hydrogenations, e.g. Fischer-Tropsch processes
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/60—Reduction reactions, e.g. hydrogenation
- B01J2231/64—Reductions in general of organic substrates, e.g. hydride reductions or hydrogenations
- B01J2231/641—Hydrogenation of organic substrates, i.e. H2 or H-transfer hydrogenations, e.g. Fischer-Tropsch processes
- B01J2231/645—Hydrogenation of organic substrates, i.e. H2 or H-transfer hydrogenations, e.g. Fischer-Tropsch processes of C=C or C-C triple bonds
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/80—Complexes comprising metals of Group VIII as the central metal
- B01J2531/82—Metals of the platinum group
- B01J2531/821—Ruthenium
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/80—Complexes comprising metals of Group VIII as the central metal
- B01J2531/82—Metals of the platinum group
- B01J2531/825—Osmium
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2540/00—Compositional aspects of coordination complexes or ligands in catalyst systems
- B01J2540/20—Non-coordinating groups comprising halogens
- B01J2540/22—Non-coordinating groups comprising halogens comprising fluorine, e.g. trifluoroacetate
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2540/00—Compositional aspects of coordination complexes or ligands in catalyst systems
- B01J2540/30—Non-coordinating groups comprising sulfur
- B01J2540/34—Sulfonyl groups
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2540/00—Compositional aspects of coordination complexes or ligands in catalyst systems
- B01J2540/60—Groups characterized by their function
- B01J2540/62—Activating groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08C—TREATMENT OR CHEMICAL MODIFICATION OF RUBBERS
- C08C19/00—Chemical modification of rubber
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Inorganic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/CN2011/001753 WO2013056400A1 (en) | 2011-10-21 | 2011-10-21 | Catalyst compositions and their use for hydrogenation of nitrile rubber |
| CNPCT/CN2011/001753 | 2011-10-21 | ||
| PCT/EP2012/070815 WO2013057289A2 (en) | 2011-10-21 | 2012-10-19 | Catalyst compositions and their use for hydrogenation of nitrile rubber |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2015501207A JP2015501207A (ja) | 2015-01-15 |
| JP5990591B2 true JP5990591B2 (ja) | 2016-09-14 |
Family
ID=47076203
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014536269A Active JP5990591B2 (ja) | 2011-10-21 | 2012-10-19 | 触媒組成物およびニトリルゴムの水素化のためのそれらの使用 |
Country Status (10)
| Country | Link |
|---|---|
| US (2) | US20150025199A1 (enExample) |
| EP (1) | EP2768611B1 (enExample) |
| JP (1) | JP5990591B2 (enExample) |
| KR (1) | KR101657383B1 (enExample) |
| BR (1) | BR112014009472A2 (enExample) |
| CA (1) | CA2852648C (enExample) |
| IN (1) | IN2014DN03160A (enExample) |
| MX (1) | MX373759B (enExample) |
| TW (1) | TWI561304B (enExample) |
| WO (2) | WO2013056400A1 (enExample) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2013056461A1 (en) * | 2011-10-21 | 2013-04-25 | Lanxess Deutschland Gmbh | Catalyst compositions and their use for hydrogenation of nitrile rubber |
| EP2676969B1 (en) * | 2012-06-22 | 2016-06-01 | University Of Waterloo | Tandem metathesis and hydrogenation of diene-based polymers in latex |
| KR101621699B1 (ko) | 2014-03-31 | 2016-05-19 | 이스켐주식회사 | 폴리 d c p d의 중합방법 |
| AU2018338636A1 (en) | 2017-09-27 | 2020-04-23 | ArchForm Inc. | Fabrication of dental appliances |
| EP3781309A1 (en) | 2018-04-20 | 2021-02-24 | ARLANXEO Deutschland GmbH | Hydrogenation catalyst compositions and their use for hydrogenation of nitrile rubber |
| CN112088044B (zh) * | 2018-04-27 | 2023-10-24 | 阿朗新科德国有限责任公司 | 钌和锇催化剂用于丁腈橡胶复分解的用途 |
| WO2020126345A1 (en) | 2018-12-17 | 2020-06-25 | Arlanxeo Deutschland Gmbh | Process for preparing hnbr solutions with alternative solvents |
| CN111905821B (zh) * | 2020-07-31 | 2023-06-16 | 青岛科技大学 | 一种共轭二烯烃胶乳催化加氢用催化剂及制备方法和应用 |
Family Cites Families (42)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3700637A (en) | 1970-05-08 | 1972-10-24 | Shell Oil Co | Diene-nitrile rubbers |
| DE2539132C2 (de) | 1975-09-03 | 1987-04-09 | Bayer Ag, 5090 Leverkusen | Verwendung hydrierter Dien-Copolymere als temperaturbeständige Materialien auf dem Dichtungssektor |
| CA1203047A (en) | 1982-12-08 | 1986-04-08 | Hormoz Azizian | Polymer hydrogenation process |
| CA1220300A (en) | 1982-12-08 | 1987-04-07 | Polysar Limited | Polymer hydrogenation process |
| DE3329974A1 (de) | 1983-08-19 | 1985-02-28 | Bayer Ag, 5090 Leverkusen | Herstellung von hydrierten nitrilkautschuken |
| DE3433392A1 (de) | 1984-09-12 | 1986-03-20 | Bayer Ag, 5090 Leverkusen | Hydrierung nitrilgruppenhaltiger ungesaettigter polymerer |
| DE3529252A1 (de) | 1985-08-16 | 1987-02-19 | Bayer Ag | Verfahren zur selektiven hydrierung ungesaettigter verbindungen |
| DE3540918A1 (de) | 1985-11-19 | 1987-05-21 | Bayer Ag | Verfahren zur selektiven hydrierung ungesaettigter verbindungen |
| DE3541689A1 (de) | 1985-11-26 | 1987-05-27 | Bayer Ag | Verfahren zur selektiven hydrierung nitrilgruppenhaltiger ungesaettigter polymerer |
| US4816525A (en) | 1987-07-06 | 1989-03-28 | University Of Waterloo | Polymer hydrogenation process |
| DE4025781A1 (de) | 1990-08-15 | 1992-02-20 | Bayer Ag | Hydrierte butadien/isopren/(meth-)acrylnitril- copolymerisate |
| DE19714972C2 (de) | 1997-04-10 | 2001-12-06 | Storz Endoskop Gmbh Schaffhaus | Einrichtung zur Überwachung der Applikation einer Neutralelektrode |
| EP1197509B1 (en) | 1999-05-31 | 2011-07-06 | Zeon Corporation | Process for producing hydrogenated ring-opening polymerization polymer of cycloolefin |
| CA2419485C (en) | 2000-08-10 | 2007-10-30 | The Trustees Of Boston College | Recyclable metathesis catalysts |
| TW593386B (en) | 2001-06-12 | 2004-06-21 | Bayer Inc | Process for the preparation of low molecular weight hydrogenated nitrile rubber |
| CA2350280A1 (en) | 2001-06-12 | 2002-12-12 | Bayer Inc. | Low molecular weight hydrogenated nitrile rubber |
| CN1265882C (zh) | 2001-08-01 | 2006-07-26 | 加州理工学院 | 六配位钌或锇金属卡宾易位催化剂 |
| US6939982B2 (en) * | 2002-05-15 | 2005-09-06 | The Trustees Of Boston College | Recyclable chiral metathesis catalysts |
| PL199412B1 (pl) * | 2002-10-15 | 2008-09-30 | Boehringer Ingelheim Int | Nowe kompleksy rutenu jako (pre)katalizatory reakcji metatezy, pochodne 2-alkoksy-5-nitrostyrenu jako związki pośrednie i sposób ich wytwarzania |
| DE10313702A1 (de) | 2003-03-27 | 2004-10-07 | Basf Ag | Katalysator und Verfahren zur Hydrierung von Carbonylverbindungen |
| CA2462005A1 (en) | 2004-02-23 | 2005-08-23 | Bayer Inc. | Process for the preparation of low molecular weight hydrogenated nitrile rubber |
| JP2005272572A (ja) * | 2004-03-24 | 2005-10-06 | Nippon Zeon Co Ltd | 水素化環状オレフィン重合体の製造方法 |
| US7385010B2 (en) * | 2005-03-18 | 2008-06-10 | Lanxess Inc. | Hydrogenation of diene-based polymer latex |
| KR101269568B1 (ko) | 2005-07-04 | 2013-06-04 | 자난 사이텍 컴퍼니 리미티드 | 루테늄 착물 리간드, 루테늄 착물, 고정 루테늄 착물 촉매및 그의 제조방법과 용도 |
| ATE538139T1 (de) | 2005-08-30 | 2012-01-15 | Lanxess Deutschland Gmbh | Verwendung von katalysatoren für den metatheseabbau von nitrilkautschuk |
| DE102006008521A1 (de) * | 2006-02-22 | 2007-08-23 | Lanxess Deutschland Gmbh | Verwendung von Katalysatoren mit erhöhter Aktivität für die NBR-Metathese |
| DE102006008520A1 (de) | 2006-02-22 | 2007-08-23 | Lanxess Deutschland Gmbh | Neue Katalysator-Systeme und deren Verwendung für Metathese-Reaktionen |
| DE102006040569A1 (de) * | 2006-08-30 | 2008-03-06 | Lanxess Deutschland Gmbh | Verfahren zum Metathese-Abbau von Nitrilkautschuken |
| DE102006043704A1 (de) | 2006-09-18 | 2008-03-27 | Umicore Ag & Co. Kg | Neue Metathesekatalysatoren |
| EP2027920B1 (de) | 2007-08-21 | 2014-10-08 | LANXESS Deutschland GmbH | Katalysatoren für Metathese-Reaktionen |
| EP2028194B1 (en) | 2007-08-21 | 2010-05-12 | Lanxess Deutschland GmbH | Metathesis of nitrile rubbers in the presence of transition metal complex catalysts |
| DE102007039526A1 (de) * | 2007-08-21 | 2009-02-26 | Lanxess Deutschland Gmbh | Katalysator-Systeme und deren Verwendung für Metathese-Reaktionen |
| DE102007039525A1 (de) * | 2007-08-21 | 2009-02-26 | Lanxess Deutschland Gmbh | Verfahren zum Metathese-Abbau von Nitrilkautschuk |
| EP2072532A1 (en) | 2007-12-21 | 2009-06-24 | Lanxess Deutschland GmbH | A process for removing iron-residues, rhodium- and ruthenium-containing catalyst residues from optionally hydrogenated nitrile rubber |
| CA2646056A1 (en) | 2007-12-21 | 2009-06-21 | Lanxess Deutschland Gmbh | A process for removing ruthenium-containing catalyst residues from optionally hydrogenated nitrile rubber |
| EP2147721A1 (de) * | 2008-07-08 | 2010-01-27 | Lanxess Deutschland GmbH | Katalysator-Systeme und deren Verwendung für Metathese-Reaktionen |
| EP2143489A1 (de) | 2008-07-08 | 2010-01-13 | Lanxess Deutschland GmbH | Katalysator-Systeme und deren Verwendung für Metathese-Reaktionen |
| FR2934178B1 (fr) * | 2008-07-25 | 2010-09-10 | Rhodia Operations | Compositions catalytiques pour la metathese de corps gras insatures avec des olefines et procedes de metathese les mettant en oeuvre |
| EP2289620A1 (en) | 2009-08-31 | 2011-03-02 | LANXESS Deutschland GmbH | Process for the preparation of hydrogenated nitrile rubber |
| EP2289621A1 (en) | 2009-08-31 | 2011-03-02 | LANXESS Deutschland GmbH | Process for the preparation of low molecular weight hydrogenated nitrile rubber |
| WO2011079439A1 (en) | 2009-12-30 | 2011-07-07 | Zannan Scitech Co., Ltd. | Highly active metathesis catalysts selective for romp and rcm reactions |
| WO2011107979A1 (en) | 2010-03-03 | 2011-09-09 | Whitecastle Investments Ltd. | Led lamp fitting having an integral cooling fan |
-
2011
- 2011-10-21 WO PCT/CN2011/001753 patent/WO2013056400A1/en not_active Ceased
-
2012
- 2012-10-19 MX MX2014004751A patent/MX373759B/es active IP Right Grant
- 2012-10-19 US US14/352,071 patent/US20150025199A1/en not_active Abandoned
- 2012-10-19 WO PCT/EP2012/070815 patent/WO2013057289A2/en not_active Ceased
- 2012-10-19 JP JP2014536269A patent/JP5990591B2/ja active Active
- 2012-10-19 CA CA2852648A patent/CA2852648C/en not_active Expired - Fee Related
- 2012-10-19 EP EP12778303.3A patent/EP2768611B1/en active Active
- 2012-10-19 BR BR112014009472A patent/BR112014009472A2/pt not_active Application Discontinuation
- 2012-10-19 IN IN3160DEN2014 patent/IN2014DN03160A/en unknown
- 2012-10-19 KR KR1020147013546A patent/KR101657383B1/ko active Active
- 2012-10-22 TW TW101138915A patent/TWI561304B/zh not_active IP Right Cessation
-
2018
- 2018-01-10 US US15/867,347 patent/US10500578B2/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| BR112014009472A2 (pt) | 2017-05-09 |
| US10500578B2 (en) | 2019-12-10 |
| CA2852648A1 (en) | 2013-04-25 |
| JP2015501207A (ja) | 2015-01-15 |
| KR20140084227A (ko) | 2014-07-04 |
| EP2768611B1 (en) | 2018-08-01 |
| WO2013057289A2 (en) | 2013-04-25 |
| MX373759B (es) | 2020-03-24 |
| CA2852648C (en) | 2020-09-29 |
| TW201332652A (zh) | 2013-08-16 |
| WO2013057289A3 (en) | 2013-09-26 |
| IN2014DN03160A (enExample) | 2015-05-22 |
| MX2014004751A (es) | 2014-11-10 |
| TWI561304B (en) | 2016-12-11 |
| KR101657383B1 (ko) | 2016-09-13 |
| US20180297022A1 (en) | 2018-10-18 |
| EP2768611A2 (en) | 2014-08-27 |
| US20150025199A1 (en) | 2015-01-22 |
| WO2013056400A1 (en) | 2013-04-25 |
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