ES2720898T3 - Catálisis de metátesis altamente activa selectiva para ROMP y RCM - Google Patents
Catálisis de metátesis altamente activa selectiva para ROMP y RCM Download PDFInfo
- Publication number
- ES2720898T3 ES2720898T3 ES10840586T ES10840586T ES2720898T3 ES 2720898 T3 ES2720898 T3 ES 2720898T3 ES 10840586 T ES10840586 T ES 10840586T ES 10840586 T ES10840586 T ES 10840586T ES 2720898 T3 ES2720898 T3 ES 2720898T3
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- Prior art keywords
- romp
- rcm
- catalysis
- highly active
- halogen
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- 238000006555 catalytic reaction Methods 0.000 title 1
- 238000005649 metathesis reaction Methods 0.000 title 1
- 238000007152 ring opening metathesis polymerisation reaction Methods 0.000 title 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 3
- 229910052736 halogen Inorganic materials 0.000 abstract 3
- 150000002367 halogens Chemical class 0.000 abstract 3
- 125000003282 alkyl amino group Chemical group 0.000 abstract 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 1
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 1
- -1 2,4,6-trimethylphenyl Chemical group 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical group [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 abstract 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 1
- 125000004471 alkyl aminosulfonyl group Chemical group 0.000 abstract 1
- 125000001769 aryl amino group Chemical group 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract 1
- 239000003446 ligand Substances 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 229910052707 ruthenium Inorganic materials 0.000 abstract 1
- 229910052723 transition metal Inorganic materials 0.000 abstract 1
- 150000003624 transition metals Chemical class 0.000 abstract 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
-
- 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
-
- 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
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
- B01J23/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals of the platinum group metals
- B01J23/44—Palladium
-
- 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
-
- 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/57—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C233/58—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of rings other than six-membered aromatic rings having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/54—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and etherified hydroxy groups bound to the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/20—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile 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
- C08F4/00—Polymerisation catalysts
- C08F4/42—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
- C08F4/72—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from metals not provided for in group C08F4/44
- C08F4/80—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from metals not provided for in group C08F4/44 selected from iron group metals or platinum group metals
-
- 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
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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
- 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
- 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)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Inorganic Chemistry (AREA)
- Polymers & Plastics (AREA)
- Medicinal Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyridine Compounds (AREA)
- Polymerization Catalysts (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
- Pyrrole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
Un complejo de metal de transición que tiene la siguiente estructura IIa,**Fórmula** en donde: m = 0 o 1, n = 1; M es rutenio; cada uno de L1 y L2 es anión cloruro); L es un ligando donador de electrones que tiene la siguiente estructura IIIa o IIId:**Fórmula** y en IIIa, q = 1, R4 y R5 son cada uno 2,4,6-trimetilfenilo, R6 y R7 son cada uno H; o en IIId, R8 y R9 son cada uno ciclohexilo (Cy); cuando m = 1, X es CH2; Y es NH o alquilamino C1-C4; "Y --- X" es enlace sencillo; cuando m = 0, Y es NH, alquilamino C1-C4 o arilamino C6-C9; n = 1, p = 0; Y1 es oxígeno; R1 es H; R2 es metilo, etilo o isopropilo; E es H, halógeno, nitro, alcoxi C1-C4, alcoxicarbonilo C1-C4, o alquilaminosulfonilo C1-C8; E1 y E2 son cada uno H, o halógeno; E3 es H; E4 es H o alquilo C1-C4; E5 y E6 es H, halógeno, alquilo C1-C4 o alcoxi C1-C6; E7 es H o alquilo C1-C4. 15
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
PCT/CN2009/076226 WO2011079439A1 (en) | 2009-12-30 | 2009-12-30 | Highly active metathesis catalysts selective for romp and rcm reactions |
PCT/CN2010/080477 WO2011079799A1 (en) | 2009-12-30 | 2010-12-30 | Highly active metathesis catalysis selective for romp and rcm |
Publications (1)
Publication Number | Publication Date |
---|---|
ES2720898T3 true ES2720898T3 (es) | 2019-07-25 |
Family
ID=44226119
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ES16164005T Active ES2711130T3 (es) | 2009-12-30 | 2010-12-30 | Catalizadores de metátesis altamente activos selectivos para reacciones ROMP y RCM |
ES10840586T Active ES2720898T3 (es) | 2009-12-30 | 2010-12-30 | Catálisis de metátesis altamente activa selectiva para ROMP y RCM |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ES16164005T Active ES2711130T3 (es) | 2009-12-30 | 2010-12-30 | Catalizadores de metátesis altamente activos selectivos para reacciones ROMP y RCM |
Country Status (11)
Country | Link |
---|---|
EP (2) | EP2519350B1 (es) |
JP (1) | JP5766717B2 (es) |
KR (1) | KR101509298B1 (es) |
AU (1) | AU2010338707B2 (es) |
BR (2) | BR112012016397B1 (es) |
CA (1) | CA2785864C (es) |
ES (2) | ES2711130T3 (es) |
MX (1) | MX338800B (es) |
PL (2) | PL3064272T3 (es) |
RU (1) | RU2546656C2 (es) |
WO (2) | WO2011079439A1 (es) |
Families Citing this family (48)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP2471851A1 (de) | 2010-12-29 | 2012-07-04 | LANXESS Deutschland GmbH | Vulkanisierbare Zusammensetzungen auf Basis Epoxygruppen-haltiger Nitrilkautschuke |
EP2471852A1 (de) | 2010-12-29 | 2012-07-04 | Lanxess Deutschland GmbH | Vulkanisierbare Zusammensetzungen auf Basis Epoxygruppen-haltiger Nitrilkautschuke |
EP2581409A1 (de) | 2011-10-11 | 2013-04-17 | Lanxess Deutschland GmbH | Vulkanisierbare Zusammensetzungen auf Basis Epoxygruppen-haltiger Nitrilkautschuke |
WO2013056459A1 (en) | 2011-10-21 | 2013-04-25 | Lanxess Deutschland Gmbh | Catalyst compositions and their use for hydrogenation of nitrile rubber |
WO2013056461A1 (en) * | 2011-10-21 | 2013-04-25 | Lanxess Deutschland Gmbh | Catalyst compositions and their use for hydrogenation of nitrile rubber |
CN103974772B (zh) * | 2011-10-21 | 2017-03-29 | 阿朗新科德国有限责任公司 | 包括钌或锇卡宾络合物和末端烯烃的催化剂组合物及其用于氢化丁腈橡胶的用途 |
WO2013056463A1 (en) * | 2011-10-21 | 2013-04-25 | Lanxess Deutschland Gmbh | Catalyst compositions and their use for hydrogenation of nitrile rubber |
CN104023845B (zh) * | 2011-10-21 | 2016-10-05 | 朗盛德国有限责任公司 | 包括格鲁布斯-荷维达型络合物和末端烯烃的催化剂组合物及其用于氢化丁腈橡胶的用途 |
WO2013056400A1 (en) * | 2011-10-21 | 2013-04-25 | Lanxess Deutschland Gmbh | Catalyst compositions and their use for hydrogenation of nitrile rubber |
WO2013098052A2 (en) | 2011-12-28 | 2013-07-04 | Lanxess Deutschland Gmbh | Metathesis of nitrile rubbers in the presence of transition metal complex catalysts |
PL230302B1 (pl) | 2012-02-27 | 2018-10-31 | Apeiron Synthesis Spolka Z Ograniczona Odpowiedzialnoscia | Katalizatory metatezy zawierające grupy oniowe |
EP2639219B1 (en) | 2012-03-14 | 2016-08-10 | Umicore AG & Co. KG | Ruthenium-based metathesis catalysts and precursors for their preparation |
KR102049820B1 (ko) * | 2012-03-16 | 2020-01-22 | 제온 코포레이션 | 개환 메타세시스 중합체 수소화물의 제조 방법 및 수지 조성물 |
WO2013158225A1 (en) * | 2012-04-18 | 2013-10-24 | Exxonmobil Chemical Patents Inc. | Polyolefin compositions and methods of production thereof |
US8809456B2 (en) | 2012-04-18 | 2014-08-19 | Exxonmobil Chemical Patents Inc. | Polyolefin compositions and methods of production thereof |
WO2013159365A1 (en) | 2012-04-28 | 2013-10-31 | Lanxess Deutschland Gmbh | Hydrogenation of nitrile rubber |
EP2867243B1 (en) | 2012-06-29 | 2016-04-13 | Apeiron Synthesis S.A. | Metal complexes, their application and methods of carrying out of metathesis reaction |
WO2014050890A1 (ja) | 2012-09-26 | 2014-04-03 | Rimtec株式会社 | 重合性組成物および樹脂成形体の製造方法 |
PL227609B1 (pl) * | 2012-11-15 | 2018-01-31 | Univ Warszawski | Nowe kompleksy rutenu, sposób ich wytwarzania oraz ich zastosowanie |
US9598531B2 (en) | 2013-02-27 | 2017-03-21 | Materia, Inc. | Olefin metathesis catalyst compositions comprising at least two metal carbene olefin metathesis catalysts |
KR102211385B1 (ko) * | 2013-02-27 | 2021-02-03 | 마터리아 인코포레이티드 | 금속 카르벤 올레핀 복분해 2종 촉매 조성물 |
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CN105829412B (zh) * | 2013-12-26 | 2019-06-11 | Rimtec株式会社 | 复合成型体的制造方法 |
RU2562775C1 (ru) * | 2014-06-26 | 2015-09-10 | Общество с ограниченной ответственностью "Объединенный центр исследований и разработок" (ООО "РН-ЦИР") | Способ получения 2-аминометилстиролов, содержащих гетероциклический фрагмент |
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RU2596198C1 (ru) * | 2015-07-23 | 2016-08-27 | Открытое акционерное общество "Нефтяная компания "Роснефть" | Способ получения 2-аминометилстиролов, содержащих гетероциклический фрагмент |
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CN107233920A (zh) * | 2016-03-29 | 2017-10-10 | 上海东杰高分子材料有限公司 | 一种钌络合物催化剂 |
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WO2009142535A1 (ru) * | 2008-05-22 | 2009-11-26 | Общество С Ограниченной Ответственностью "Объединённый Центр Исследований И Разработок" | Катализатор метатезисной полимеризации дициклопентадиена |
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EP2398814A4 (en) * | 2009-02-18 | 2013-02-20 | Henkel Corp | THERMALLY SWITCHED RUTHENIUM INITIATORS |
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EP3064272B1 (en) | 2018-11-28 |
JP2013516392A (ja) | 2013-05-13 |
WO2011079799A1 (en) | 2011-07-07 |
KR20120099299A (ko) | 2012-09-07 |
CA2785864A1 (en) | 2011-07-07 |
AU2010338707B2 (en) | 2014-08-14 |
MX338800B (es) | 2016-05-02 |
MX2012007758A (es) | 2012-11-22 |
EP2519350A4 (en) | 2014-03-12 |
WO2011079439A1 (en) | 2011-07-07 |
EP2519350B1 (en) | 2019-03-20 |
EP2519350A1 (en) | 2012-11-07 |
PL3064272T3 (pl) | 2019-07-31 |
BR112012016397A2 (pt) | 2017-10-31 |
BR112012016397B1 (pt) | 2018-11-13 |
PL2519350T3 (pl) | 2019-08-30 |
EP3064272A1 (en) | 2016-09-07 |
ES2711130T3 (es) | 2019-04-30 |
JP5766717B2 (ja) | 2015-08-19 |
CA2785864C (en) | 2015-06-16 |
BR122018015766B1 (pt) | 2019-05-07 |
AU2010338707A1 (en) | 2012-07-26 |
RU2012132191A (ru) | 2014-02-10 |
RU2546656C2 (ru) | 2015-04-10 |
KR101509298B1 (ko) | 2015-04-07 |
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