PL400162A1 - Nowe kompleksy rutenu, ich zastosowanie w reakcjach metatezy oraz sposób prowadzenia reakcji metatezy - Google Patents

Nowe kompleksy rutenu, ich zastosowanie w reakcjach metatezy oraz sposób prowadzenia reakcji metatezy

Info

Publication number
PL400162A1
PL400162A1 PL400162A PL40016212A PL400162A1 PL 400162 A1 PL400162 A1 PL 400162A1 PL 400162 A PL400162 A PL 400162A PL 40016212 A PL40016212 A PL 40016212A PL 400162 A1 PL400162 A1 PL 400162A1
Authority
PL
Poland
Prior art keywords
metathesis reactions
conducting
ruthenium complexes
new ruthenium
reactions
Prior art date
Application number
PL400162A
Other languages
English (en)
Inventor
Krzysztof Skowerski
Michał Bieniek
Original Assignee
Apeiron Synthesis Spólka Z Ograniczona Odpowiedzialnoscia
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Apeiron Synthesis Spólka Z Ograniczona Odpowiedzialnoscia filed Critical Apeiron Synthesis Spólka Z Ograniczona Odpowiedzialnoscia
Priority to PL400162A priority Critical patent/PL400162A1/pl
Priority to PCT/EP2013/065839 priority patent/WO2014016422A1/en
Priority to JP2015523570A priority patent/JP6121533B2/ja
Priority to CA2875956A priority patent/CA2875956C/en
Priority to RU2014152207/04A priority patent/RU2586213C1/ru
Priority to AU2013294909A priority patent/AU2013294909B2/en
Priority to US14/406,741 priority patent/US9328132B2/en
Priority to PL13745377T priority patent/PL2877478T3/pl
Priority to SG11201408224SA priority patent/SG11201408224SA/en
Priority to EP13745377.5A priority patent/EP2877478B1/en
Priority to KR1020157000377A priority patent/KR101749238B1/ko
Priority to CN201380036034.XA priority patent/CN104428306B/zh
Publication of PL400162A1 publication Critical patent/PL400162A1/pl
Priority to IL236128A priority patent/IL236128A/en

Links

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
    • 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
    • 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]

Landscapes

  • 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)

Abstract

Przedmiotem wynalazku sa kompleksy metali o wzorze ogólnym 1. Wynalazek dotyczy takze zastosowania kompleksów metali o wzorze ogólnym 1 jako (pre)katalizatorów reakcji metatezy olefin, oraz sposobu prowadzenia reakcji metatezy olefin.
PL400162A 2012-07-27 2012-07-27 Nowe kompleksy rutenu, ich zastosowanie w reakcjach metatezy oraz sposób prowadzenia reakcji metatezy PL400162A1 (pl)

Priority Applications (13)

Application Number Priority Date Filing Date Title
PL400162A PL400162A1 (pl) 2012-07-27 2012-07-27 Nowe kompleksy rutenu, ich zastosowanie w reakcjach metatezy oraz sposób prowadzenia reakcji metatezy
AU2013294909A AU2013294909B2 (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
JP2015523570A JP6121533B2 (ja) 2012-07-27 2013-07-26 新規ルテニウム錯体、それらのメタセシス反応における使用方法、及びメタセシス反応を実施するための方法
CA2875956A CA2875956C (en) 2012-07-27 2013-07-26 Ruthenium complexes comprising chelating alkylidene ligands and their use as metathesis catalysts
RU2014152207/04A RU2586213C1 (ru) 2012-07-27 2013-07-26 Новые рутениевые комплексы, их применение в реакциях метатезиса и способ проведения реакции метатезиса
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
US14/406,741 US9328132B2 (en) 2012-07-27 2013-07-26 Ruthenium complexes, their use in the metathesis reactions, and a process for carrying out the metathesis reaction
PL13745377T PL2877478T3 (pl) 2012-07-27 2013-07-26 Nowe kompleksy rutenu, ich zastosowanie w reakcjach metatezy oraz sposób prowadzenia reakcji metatezy
SG11201408224SA SG11201408224SA (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
EP13745377.5A EP2877478B1 (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
KR1020157000377A KR101749238B1 (ko) 2012-07-27 2013-07-26 신규 루테늄 착물, 복분해 반응에서 이의 용도, 및 복분해 반응의 수행 방법
CN201380036034.XA CN104428306B (zh) 2012-07-27 2013-07-26 新的钌络合物、其在复分解反应中的应用以及用于进行复分解反应的方法
IL236128A IL236128A (en) 2012-07-27 2014-12-08 Ruthenium bracelets, their use of metathesis reactions, and the process of performing the metathesis reaction

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PL400162A PL400162A1 (pl) 2012-07-27 2012-07-27 Nowe kompleksy rutenu, ich zastosowanie w reakcjach metatezy oraz sposób prowadzenia reakcji metatezy

Publications (1)

Publication Number Publication Date
PL400162A1 true PL400162A1 (pl) 2014-02-03

Family

ID=48917515

Family Applications (2)

Application Number Title Priority Date Filing Date
PL400162A PL400162A1 (pl) 2012-07-27 2012-07-27 Nowe kompleksy rutenu, ich zastosowanie w reakcjach metatezy oraz sposób prowadzenia reakcji metatezy
PL13745377T PL2877478T3 (pl) 2012-07-27 2013-07-26 Nowe kompleksy rutenu, ich zastosowanie w reakcjach metatezy oraz sposób prowadzenia reakcji metatezy

Family Applications After (1)

Application Number Title Priority Date Filing Date
PL13745377T PL2877478T3 (pl) 2012-07-27 2013-07-26 Nowe kompleksy rutenu, ich zastosowanie w reakcjach metatezy oraz sposób prowadzenia reakcji metatezy

Country Status (12)

Country Link
US (1) US9328132B2 (pl)
EP (1) EP2877478B1 (pl)
JP (1) JP6121533B2 (pl)
KR (1) KR101749238B1 (pl)
CN (1) CN104428306B (pl)
AU (1) AU2013294909B2 (pl)
CA (1) CA2875956C (pl)
IL (1) IL236128A (pl)
PL (2) PL400162A1 (pl)
RU (1) RU2586213C1 (pl)
SG (1) SG11201408224SA (pl)
WO (1) WO2014016422A1 (pl)

Families Citing this family (14)

* Cited by examiner, † Cited by third party
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
JP6882295B2 (ja) * 2015-12-10 2021-06-02 ユミコア・アクチエンゲゼルシャフト・ウント・コムパニー・コマンディットゲゼルシャフトＵｍｉｃｏｒｅ ＡＧ ＆ Ｃｏ．ＫＧ オレフィンメタセシス触媒
WO2018236191A1 (ko) * 2017-06-23 2018-12-27 광주과학기술원 루테늄 착물 형성을 위한 리간드, 루테늄 착물 촉매 및 이의 제조방법과 용도
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
US11939410B2 (en) 2018-06-29 2024-03-26 Apeiron Synthesis S.A. Organoruthenium complexes as precatalysts for olefin metathesis
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
JP7223854B2 (ja) 2018-12-21 2023-02-16 プロメラス， エルエルシー ポリシクロオレフィンモノマー及び架橋剤に由来する高衝撃強度の３ｄ印刷材料
KR102670566B1 (ko) * 2019-01-18 2024-05-31 광주과학기술원 루테늄 착화합물, 이의 제조를 위한 리간드 및 이의 용도
US11692056B2 (en) 2019-07-25 2023-07-04 Promerus, Llc Stable polycycloolefin polymer and inorganic nanoparticle compositions as optical materials
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
US20240150384A1 (en) 2021-02-02 2024-05-09 Apeiron Synthesis S.A. Long shelf life stable organoruthenium complexes as (pre)catalysts for olefin metathesis
WO2024083874A1 (en) 2022-10-21 2024-04-25 Merck Patent Gmbh Composition

Family Cites Families (12)

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Publication number Priority date Publication date Assignee Title
CA2441980C (en) * 2001-03-26 2011-07-19 Dow Global Technologies Inc. Metathesis of unsaturated fatty acid esters or unsaturated fatty acids with lower olefins
WO2002083742A2 (en) * 2001-04-16 2002-10-24 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
CN102643175B (zh) * 2005-07-04 2014-12-10 赞南科技(上海)有限公司 钌络合物配体、钌络合物、固载钌络合物催化剂及其制备方法和用途
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

Also Published As

Publication number Publication date
EP2877478B1 (en) 2016-11-16
AU2013294909B2 (en) 2015-11-19
CN104428306A (zh) 2015-03-18
IL236128A0 (en) 2015-02-01
AU2013294909A1 (en) 2015-01-22
KR20150023672A (ko) 2015-03-05
CA2875956A1 (en) 2014-01-30
US20150158896A1 (en) 2015-06-11
CN104428306B (zh) 2017-05-24
EP2877478A1 (en) 2015-06-03
WO2014016422A1 (en) 2014-01-30
PL2877478T3 (pl) 2017-05-31
US9328132B2 (en) 2016-05-03
JP6121533B2 (ja) 2017-04-26
KR101749238B1 (ko) 2017-06-20
CA2875956C (en) 2016-01-19
IL236128A (en) 2017-07-31
RU2586213C1 (ru) 2016-06-10
SG11201408224SA (en) 2015-01-29
JP2015525776A (ja) 2015-09-07

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