KR101749238B1 - 신규 루테늄 착물, 복분해 반응에서 이의 용도, 및 복분해 반응의 수행 방법 - Google Patents
신규 루테늄 착물, 복분해 반응에서 이의 용도, 및 복분해 반응의 수행 방법 Download PDFInfo
- Publication number
- KR101749238B1 KR101749238B1 KR1020157000377A KR20157000377A KR101749238B1 KR 101749238 B1 KR101749238 B1 KR 101749238B1 KR 1020157000377 A KR1020157000377 A KR 1020157000377A KR 20157000377 A KR20157000377 A KR 20157000377A KR 101749238 B1 KR101749238 B1 KR 101749238B1
- Authority
- KR
- South Korea
- Prior art keywords
- catalyst
- metathesis
- metathesis reaction
- general formula
- complex
- 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
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- WDCCDORXEJTPGD-AATRIKPKSA-N CC(OC/C=C/Cc1ccccc1)=O Chemical compound CC(OC/C=C/Cc1ccccc1)=O WDCCDORXEJTPGD-AATRIKPKSA-N 0.000 description 1
- 0 CC1C(CC*)*N*1 Chemical compound CC1C(CC*)*N*1 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/0046—Ruthenium compounds
-
- 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
-
- 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
- B01J31/2409—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring with more than one complexing phosphine-P atom
- B01J31/2414—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring with more than one complexing phosphine-P atom comprising aliphatic or saturated rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C6/00—Preparation of hydrocarbons from hydrocarbons containing a different number of carbon atoms by redistribution reactions
- C07C6/02—Metathesis reactions at an unsaturated carbon-to-carbon bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/28—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group
- C07C67/293—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
- C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/475—Preparation of carboxylic acid esters by splitting of carbon-to-carbon bonds and redistribution, e.g. disproportionation or migration of groups between different molecules
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D307/28—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F132/00—Homopolymers of cyclic compounds containing no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic ring system
- C08F132/02—Homopolymers of cyclic compounds containing no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic ring system having no condensed rings
- C08F132/06—Homopolymers of cyclic compounds containing no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic ring system having no condensed rings having two or more carbon-to-carbon double bonds
-
- 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
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/02—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes
- C08G61/04—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes only aliphatic carbon atoms
- C08G61/06—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes only aliphatic carbon atoms prepared by ring-opening of carbocyclic compounds
- C08G61/08—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes only aliphatic carbon atoms prepared by ring-opening of carbocyclic compounds of carbocyclic compounds containing one or more carbon-to-carbon double bonds in the ring
-
- 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2523/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00
- C07C2523/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of noble metals
- C07C2523/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of noble metals of the platinum group metals
- C07C2523/46—Ruthenium, rhodium, osmium or iridium
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/10—Systems containing only non-condensed rings with a five-membered ring the ring being unsaturated
-
- 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
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
- C08G2261/33—Monomer units or repeat units incorporating structural elements in the main chain incorporating non-aromatic structural elements in the main chain
- C08G2261/332—Monomer units or repeat units incorporating structural elements in the main chain incorporating non-aromatic structural elements in the main chain containing only carbon atoms
- C08G2261/3325—Monomer units or repeat units incorporating structural elements in the main chain incorporating non-aromatic structural elements in the main chain containing only carbon atoms derived from other polycyclic systems
-
- 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
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/40—Polymerisation processes
- C08G2261/41—Organometallic coupling reactions
- C08G2261/418—Ring opening metathesis polymerisation [ROMP]
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Inorganic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PLP.400162 | 2012-07-27 | ||
| PL400162A PL400162A1 (pl) | 2012-07-27 | 2012-07-27 | Nowe kompleksy rutenu, ich zastosowanie w reakcjach metatezy oraz sposób prowadzenia reakcji metatezy |
| PCT/EP2013/065839 WO2014016422A1 (en) | 2012-07-27 | 2013-07-26 | Novel ruthenium complexes, their use in the metathesis reactions, and a process for carrying out the metathesis reaction |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR20150023672A KR20150023672A (ko) | 2015-03-05 |
| KR101749238B1 true KR101749238B1 (ko) | 2017-06-20 |
Family
ID=48917515
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020157000377A Expired - Fee Related KR101749238B1 (ko) | 2012-07-27 | 2013-07-26 | 신규 루테늄 착물, 복분해 반응에서 이의 용도, 및 복분해 반응의 수행 방법 |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US9328132B2 (enExample) |
| EP (1) | EP2877478B1 (enExample) |
| JP (1) | JP6121533B2 (enExample) |
| KR (1) | KR101749238B1 (enExample) |
| CN (1) | CN104428306B (enExample) |
| AU (1) | AU2013294909B2 (enExample) |
| CA (1) | CA2875956C (enExample) |
| IL (1) | IL236128A (enExample) |
| PL (2) | PL400162A1 (enExample) |
| RU (1) | RU2586213C1 (enExample) |
| SG (1) | SG11201408224SA (enExample) |
| WO (1) | WO2014016422A1 (enExample) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PL400162A1 (pl) | 2012-07-27 | 2014-02-03 | Apeiron Synthesis Spólka Z Ograniczona Odpowiedzialnoscia | Nowe kompleksy rutenu, ich zastosowanie w reakcjach metatezy oraz sposób prowadzenia reakcji metatezy |
| PL238806B1 (pl) | 2015-09-30 | 2021-10-04 | Apeiron Synthesis Spolka Akcyjna | Kompleks rutenu i sposób jego wytwarzania, związek pośredni stosowany w tym sposobie oraz zastosowanie kompleksu rutenu i związku pośredniego w metatezie olefin |
| PL3386936T3 (pl) * | 2015-12-10 | 2024-10-07 | Umicore Ag & Co. Kg | Katalizatory metatezy olefin |
| WO2018150379A2 (en) | 2017-02-17 | 2018-08-23 | Provivi, Inc. | Synthesis of pheromones and related materials via olefin metathesis |
| US11471867B2 (en) | 2017-06-23 | 2022-10-18 | Gwangju Institute Of Science And Technology | Ligand for forming ruthenium complex, ruthenium complex catalyst, production method therefor and use thereof |
| TWI758525B (zh) * | 2017-08-10 | 2022-03-21 | 日商住友電木股份有限公司 | 作為光學材料之聚環烯烴聚合物組成物 |
| TWI777027B (zh) | 2018-01-26 | 2022-09-11 | 日商住友電木股份有限公司 | 聚環烯烴單體及由能夠產生光酸作為光學材料的化合物活化之催化劑 |
| TWI794520B (zh) | 2018-06-29 | 2023-03-01 | 日商住友電木股份有限公司 | 作為 3d 列印材料之聚環烯烴單體及由能夠產生光酸之化合物活化之催化劑 |
| JP7466908B2 (ja) * | 2018-06-29 | 2024-04-15 | アペイロン シンセシス エス アー | オレフィンメタセシス用の触媒前駆体としての有機ルテニウム錯体 |
| TWI801699B (zh) | 2018-12-21 | 2023-05-11 | 日商住友電木股份有限公司 | 衍生自聚環烯烴單體及交聯劑之高衝擊強度的3d列印材料 |
| KR102670566B1 (ko) * | 2019-01-18 | 2024-05-31 | 광주과학기술원 | 루테늄 착화합물, 이의 제조를 위한 리간드 및 이의 용도 |
| CN114144450A (zh) * | 2019-07-25 | 2022-03-04 | 普罗米鲁斯有限责任公司 | 作为光学材料的稳定的聚环烯烃聚合物及无机纳米组合物 |
| WO2021060061A1 (ja) * | 2019-09-27 | 2021-04-01 | 日本ゼオン株式会社 | 重合体含有物およびその製造方法、並びに、フィルム |
| EP4267540A1 (en) | 2021-02-02 | 2023-11-01 | Apeiron Synthesis S.A. | Long shelf life stable organoruthenium complexes as (pre)catalysts for olefin metathesis |
| TWI895585B (zh) | 2021-02-02 | 2025-09-01 | 日商住友電木股份有限公司 | 作為光學材料之保存期限長期穩定的光活性本體聚合型多環烯烴組成物 |
| TW202323266A (zh) | 2021-11-29 | 2023-06-16 | 美商普羅梅勒斯有限公司 | 作為光學材料之包含保存期限長期穩定的光活性本體聚合型多環烯烴組成物之雙重ｕｖ阻斷劑 |
| WO2024083874A1 (en) | 2022-10-21 | 2024-04-25 | Merck Patent Gmbh | Composition |
| WO2025012183A1 (en) | 2023-07-10 | 2025-01-16 | Merck Patent Gmbh | Composition |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2289568C2 (ru) * | 2001-03-26 | 2006-12-20 | Дау Глобал Текнолоджиз Инк. | Способ метатезиса сложных эфиров ненасыщенных жирных кислот или ненасыщенных жирных кислот с низшими олефинами и композиция гетерогенного катализатора, предназначенная для способа метатезиса |
| EP1395616B1 (en) * | 2001-04-16 | 2019-05-22 | California Institute Of Technology | Group 8 transition metal carbene complexes as enantioselective olefin 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 |
| PL199428B1 (pl) | 2003-12-29 | 2008-09-30 | Polska Akademia Nauk Instytut | Nowe kompleksy rutenu, pochodne 2-alkoksy-4-nitrostyrenu jako (pre)katalizatory (54) reakcji metatezy, pochodne 2-alkoksy-4-nitrostyrenu jako związki pośrednie oraz sposób ich wytwarzania |
| RU2435778C2 (ru) * | 2005-07-04 | 2011-12-10 | Заннан Сайтех Ко., Лтд. | Лиганд комплекса рутения, комплекс рутения, катализатор комплекса рутения и способы его получения и применения |
| RU2311231C1 (ru) * | 2006-08-15 | 2007-11-27 | ООО "Объединенный центр исследований и разработок" | Катализатор для получения эфиров акриловой кислоты по реакции метатезиса диалкилмалеатов (варианты) и каталитическая композиция на его основе |
| 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 |
| EP2255877B1 (en) | 2009-05-07 | 2014-09-24 | Umicore AG & Co. KG | Method for preparation of ruthenium-based metathesis catalysts with chelating alkylidene ligands |
| RU2402572C1 (ru) * | 2009-07-09 | 2010-10-27 | Общество с ограниченной ответственностью "Объединенный центр исследований и разработок" | Способ получения полидициклопентадиена и материалов на его основе |
| CN102476060B (zh) * | 2010-11-24 | 2013-07-10 | 中国石油化工股份有限公司 | 一种烯烃复分解催化剂及其制备方法 |
| PL400162A1 (pl) | 2012-07-27 | 2014-02-03 | Apeiron Synthesis Spólka Z Ograniczona Odpowiedzialnoscia | Nowe kompleksy rutenu, ich zastosowanie w reakcjach metatezy oraz sposób prowadzenia reakcji metatezy |
-
2012
- 2012-07-27 PL PL400162A patent/PL400162A1/pl unknown
-
2013
- 2013-07-26 CA CA2875956A patent/CA2875956C/en active Active
- 2013-07-26 SG SG11201408224SA patent/SG11201408224SA/en unknown
- 2013-07-26 WO PCT/EP2013/065839 patent/WO2014016422A1/en not_active Ceased
- 2013-07-26 JP JP2015523570A patent/JP6121533B2/ja active Active
- 2013-07-26 US US14/406,741 patent/US9328132B2/en active Active
- 2013-07-26 EP EP13745377.5A patent/EP2877478B1/en active Active
- 2013-07-26 PL PL13745377T patent/PL2877478T3/pl unknown
- 2013-07-26 CN CN201380036034.XA patent/CN104428306B/zh active Active
- 2013-07-26 AU AU2013294909A patent/AU2013294909B2/en active Active
- 2013-07-26 RU RU2014152207/04A patent/RU2586213C1/ru active
- 2013-07-26 KR KR1020157000377A patent/KR101749238B1/ko not_active Expired - Fee Related
-
2014
- 2014-12-08 IL IL236128A patent/IL236128A/en active IP Right Grant
Non-Patent Citations (3)
| Title |
|---|
| Chem. Commun., Vol.2011, pp.1158-1159 (2011)* |
| Chem. Soc. Rev., Vol.38, pp.3360-3372 (2009)* |
| Macromolecules, Vol.36, pp.8231-8239 (2003)* |
Also Published As
| Publication number | Publication date |
|---|---|
| IL236128A (en) | 2017-07-31 |
| PL2877478T3 (pl) | 2017-05-31 |
| JP6121533B2 (ja) | 2017-04-26 |
| US20150158896A1 (en) | 2015-06-11 |
| EP2877478A1 (en) | 2015-06-03 |
| PL400162A1 (pl) | 2014-02-03 |
| EP2877478B1 (en) | 2016-11-16 |
| US9328132B2 (en) | 2016-05-03 |
| AU2013294909A1 (en) | 2015-01-22 |
| AU2013294909B2 (en) | 2015-11-19 |
| IL236128A0 (en) | 2015-02-01 |
| CN104428306A (zh) | 2015-03-18 |
| CA2875956A1 (en) | 2014-01-30 |
| KR20150023672A (ko) | 2015-03-05 |
| WO2014016422A1 (en) | 2014-01-30 |
| CN104428306B (zh) | 2017-05-24 |
| SG11201408224SA (en) | 2015-01-29 |
| JP2015525776A (ja) | 2015-09-07 |
| RU2586213C1 (ru) | 2016-06-10 |
| CA2875956C (en) | 2016-01-19 |
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