BR112017005473A2 - complexo de vanádio fosfínico, sistema catalítico que compreende o dito complexo de vanádio fosfínico e processo para a (co)polimerização de dienos conjugados - Google Patents
complexo de vanádio fosfínico, sistema catalítico que compreende o dito complexo de vanádio fosfínico e processo para a (co)polimerização de dienos conjugadosInfo
- Publication number
- BR112017005473A2 BR112017005473A2 BR112017005473A BR112017005473A BR112017005473A2 BR 112017005473 A2 BR112017005473 A2 BR 112017005473A2 BR 112017005473 A BR112017005473 A BR 112017005473A BR 112017005473 A BR112017005473 A BR 112017005473A BR 112017005473 A2 BR112017005473 A2 BR 112017005473A2
- Authority
- BR
- Brazil
- Prior art keywords
- vanadium complex
- phosphineic
- optionally substituted
- polymerization
- groups
- Prior art date
Links
- 229910052720 vanadium Inorganic materials 0.000 title abstract 6
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 title abstract 6
- 230000003197 catalytic effect Effects 0.000 title abstract 3
- 150000001993 dienes Chemical class 0.000 title abstract 3
- 238000006116 polymerization reaction Methods 0.000 title abstract 3
- 238000000034 method Methods 0.000 title abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 abstract 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 2
- 229910019142 PO4 Inorganic materials 0.000 abstract 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 229910052801 chlorine Inorganic materials 0.000 abstract 2
- 239000000460 chlorine Substances 0.000 abstract 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 abstract 2
- 239000010452 phosphate Substances 0.000 abstract 2
- 125000003107 substituted aryl group Chemical group 0.000 abstract 2
- 125000005346 substituted cycloalkyl group Chemical group 0.000 abstract 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 150000001450 anions Chemical class 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 150000007942 carboxylates Chemical class 0.000 abstract 1
- -1 for example Chemical class 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 abstract 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 abstract 1
- 239000012948 isocyanate Substances 0.000 abstract 1
- 150000002513 isocyanates Chemical class 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
Classifications
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- 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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/50—Organo-phosphines
- C07F9/5045—Complexes or chelates of phosphines with metallic compounds or metals
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- 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
- C07F19/00—Metal compounds according to more than one of main groups C07F1/00 - C07F17/00
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- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/46—Phosphinous acids [R2POH], [R2P(= O)H]: Thiophosphinous acids including[R2PSH]; [R2P(=S)H]; Aminophosphines [R2PNH2]; Derivatives thereof
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- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6596—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having atoms other than oxygen, sulfur, selenium, tellurium, nitrogen or phosphorus as ring hetero atoms
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F10/00—Homopolymers and copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F10/00—Homopolymers and copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F10/04—Monomers containing three or four carbon atoms
- C08F10/06—Propene
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- 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
- C08F10/00—Homopolymers and copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F10/04—Monomers containing three or four carbon atoms
- C08F10/08—Butenes
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F136/00—Homopolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
- C08F136/02—Homopolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds
- C08F136/04—Homopolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated
- C08F136/06—Butadiene
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- C08F136/00—Homopolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
- C08F136/02—Homopolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds
- C08F136/04—Homopolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated
- C08F136/08—Isoprene
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- C08F2/00—Processes of polymerisation
- C08F2/38—Polymerisation using regulators, e.g. chain terminating agents, e.g. telomerisation
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- C08F2/00—Processes of polymerisation
- C08F2/60—Polymerisation by the diene synthesis
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- C08F36/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
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- C08F36/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
- C08F36/02—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds
- C08F36/04—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated
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- C08F36/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
- C08F36/02—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds
- C08F36/04—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated
- C08F36/06—Butadiene
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- 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
- C08F36/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
- C08F36/02—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds
- C08F36/04—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated
- C08F36/08—Isoprene
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F4/00—Polymerisation catalysts
- C08F4/06—Metallic compounds other than hydrides and other than metallo-organic compounds; Boron halide or aluminium halide complexes with organic compounds containing oxygen
- C08F4/12—Metallic compounds other than hydrides and other than metallo-organic compounds; Boron halide or aluminium halide complexes with organic compounds containing oxygen of boron, aluminium, gallium, indium, thallium or rare earths
- C08F4/14—Boron halides or aluminium halides; Complexes thereof with organic compounds containing oxygen
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- C08F4/00—Polymerisation catalysts
- C08F4/06—Metallic compounds other than hydrides and other than metallo-organic compounds; Boron halide or aluminium halide complexes with organic compounds containing oxygen
- C08F4/20—Metallic compounds other than hydrides and other than metallo-organic compounds; Boron halide or aluminium halide complexes with organic compounds containing oxygen of antimony, bismuth, vanadium, niobium or tantalum
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- 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
- C08F4/44—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides
- C08F4/60—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides together with refractory metals, iron group metals, platinum group metals, manganese, rhenium technetium or compounds thereof
- C08F4/62—Refractory metals or compounds thereof
- C08F4/68—Vanadium, niobium, tantalum or compounds thereof
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- C08F4/00—Polymerisation catalysts
- C08F4/42—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
- C08F4/44—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides
- C08F4/60—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides together with refractory metals, iron group metals, platinum group metals, manganese, rhenium technetium or compounds thereof
- C08F4/62—Refractory metals or compounds thereof
- C08F4/68—Vanadium, niobium, tantalum or compounds thereof
- C08F4/68008—Vanadium, niobium, tantalum or compounds thereof the metallic compound containing a multidentate ligand, i.e. a ligand capable of donating two or more pairs of electrons to form a coordinate or ionic bond
- C08F4/68017—Bidentate ligand
- C08F4/68025—Neutral ligand
- C08F4/68086—PP
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- 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
- C08F4/74—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from metals not provided for in group C08F4/44 selected from refractory metals
- C08F4/76—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from metals not provided for in group C08F4/44 selected from refractory metals selected from titanium, zirconium, hafnium, vanadium, niobium or tantalum
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
Abstract
resumo "complexo de vanádio fosfínico, sistema catalítico que compreende o dito complexo de vanádio fosfínico e processo para a (co)polimerização de dienos conjugados". complexo de vanádio fosfínico que tem a fórmula geral (i) ou (ii): v(x)3[p(r1)n(r2)3-n]2 (i) e v(x)3[(r3)2p(r4)p(r3)2] (ii) em que: x representa um ânion selecionado a partir de halogênios tais como, por exemplo, cloro, bromo, iodo, de preferência cloro; ou é selecionado a partir dos seguintes grupos: tiocianato, isocianato, sulfato, sulfato ácido, fosfato, fosfato ácido, carboxilato, dicarboxilato; r1, idênticos ou diferentes entre si, representam um átomo de hidrogênio ou um grupo alila (ch 2 = ch-ch2-); ou são selecionados a partir de grupos c1-c20, de preferência c1-c15 alquila de cadeia linear ou ramificada, opcionalmente halogenados, grupos cicloalquila opcionalmente substituídos; n é um número inteiro que varia a partir de 0 a 3; r2, idênticos ou diferentes entre si, são selecionados a partir de grupos arila opcionalmente substituídos; r3, idênticos ou diferentes entre si, representam um átomo de hidrogênio ou um grupo alila (ch 2 = ch-ch2-); ou são selecionados a partir de grupos c1-c20, de preferência c1-c15 alquila de cadeia linear ou ramificada, opcionalmente halogenados, grupos cicloalquila opcionalmente substituídos, grupos arila opcionalmente substituídos; r4 representa um grupo -nr5, em que r5 representa um átomo de hidrogênio ou é selecionado a partir de grupos c1-c20, de preferência c1-c15 alquila de cadeia linear ou ramificada; ou r4 representa um grupo alquileno -(ch2)p-, em que p representa um número inteiro que varia a partir de 1 a 5; contanto que, na fórmula geral (i), no caso onde n é igual a 1 e é metila, r2 é diferente de fenila. o dito complexo de vanádio fosfínico de fórmula geral (i) ou (ii) pode ser vantajosamente usado em um sistema catalítico para a (co)polimerização de dienos conjugados.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
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ITMI2014A002028 | 2014-11-25 | ||
ITMI20142028 | 2014-11-25 | ||
PCT/IB2015/059072 WO2016128812A1 (en) | 2014-11-25 | 2015-11-24 | Phosphinic vanadium complex, catalytic system comprising said phosphinic vanadium complex and process for the (co) polymerization of conjugated dienes |
Publications (2)
Publication Number | Publication Date |
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BR112017005473A2 true BR112017005473A2 (pt) | 2017-12-19 |
BR112017005473B1 BR112017005473B1 (pt) | 2021-09-14 |
Family
ID=52232330
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
BR112017005473-6A BR112017005473B1 (pt) | 2014-11-25 | 2015-11-24 | Processo para a (co)polimerização de dienos conjugados e processo para polimerização de 1,3-butadieno ou isopreno |
Country Status (15)
Country | Link |
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US (3) | US20170275312A1 (pt) |
EP (1) | EP3224267B1 (pt) |
KR (1) | KR102502249B1 (pt) |
CN (1) | CN106715449B (pt) |
BR (1) | BR112017005473B1 (pt) |
CA (1) | CA2958194C (pt) |
ES (1) | ES2870594T3 (pt) |
HU (1) | HUE053465T2 (pt) |
PL (1) | PL3224267T3 (pt) |
PT (1) | PT3224267T (pt) |
RS (1) | RS61699B1 (pt) |
RU (1) | RU2685409C2 (pt) |
SA (1) | SA517380990B1 (pt) |
WO (1) | WO2016128812A1 (pt) |
ZA (1) | ZA201701180B (pt) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP6735163B2 (ja) * | 2016-06-22 | 2020-08-05 | 株式会社Adeka | バナジウム化合物、薄膜形成用原料及び薄膜の製造方法 |
CN111606955B (zh) * | 2020-07-06 | 2023-05-02 | 长春三友智造科技发展有限公司 | 一种金属有机膦配合物及其制备方法、应用 |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
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BE791406A (fr) * | 1971-11-26 | 1973-03-01 | Snam Progetti | Procede de fabrication de polymeres et copolymeres d'isobutylene |
CA2243783C (en) * | 1998-07-21 | 2007-06-05 | Nova Chemicals Ltd. | Bis-phosphinimine catalyst |
GB0306308D0 (en) * | 2003-03-19 | 2003-04-23 | Bp Chem Int Ltd | Polymerisation catalysts |
CN100569734C (zh) * | 2006-05-22 | 2009-12-16 | 中国科学院上海有机化学研究所 | 一类含杂原子的有机化合物及其在齐格勒-纳塔催化剂中的应用 |
KR101057576B1 (ko) * | 2007-08-16 | 2011-08-17 | 에스케이종합화학 주식회사 | 선택적 에틸렌 올리머고화 촉매계 |
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2015
- 2015-11-24 CN CN201580051984.9A patent/CN106715449B/zh active Active
- 2015-11-24 EP EP15808268.5A patent/EP3224267B1/en active Active
- 2015-11-24 RS RS20210442A patent/RS61699B1/sr unknown
- 2015-11-24 HU HUE15808268A patent/HUE053465T2/hu unknown
- 2015-11-24 WO PCT/IB2015/059072 patent/WO2016128812A1/en active Application Filing
- 2015-11-24 ES ES15808268T patent/ES2870594T3/es active Active
- 2015-11-24 PL PL15808268T patent/PL3224267T3/pl unknown
- 2015-11-24 PT PT158082685T patent/PT3224267T/pt unknown
- 2015-11-24 KR KR1020177008498A patent/KR102502249B1/ko active IP Right Grant
- 2015-11-24 BR BR112017005473-6A patent/BR112017005473B1/pt active IP Right Grant
- 2015-11-24 US US15/518,556 patent/US20170275312A1/en not_active Abandoned
- 2015-11-24 RU RU2017105212A patent/RU2685409C2/ru active
- 2015-11-24 CA CA2958194A patent/CA2958194C/en active Active
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2017
- 2017-02-16 ZA ZA2017/01180A patent/ZA201701180B/en unknown
- 2017-02-27 SA SA517380990A patent/SA517380990B1/ar unknown
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2019
- 2019-01-09 US US16/243,686 patent/US20190194233A1/en not_active Abandoned
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2021
- 2021-12-20 US US17/556,199 patent/US20220177500A1/en not_active Abandoned
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EP3224267A1 (en) | 2017-10-04 |
EP3224267B1 (en) | 2021-02-24 |
CN106715449A (zh) | 2017-05-24 |
ES2870594T3 (es) | 2021-10-27 |
US20170275312A1 (en) | 2017-09-28 |
ZA201701180B (en) | 2018-11-28 |
RU2685409C2 (ru) | 2019-04-18 |
SA517380990B1 (ar) | 2021-07-12 |
RS61699B1 (sr) | 2021-05-31 |
US20220177500A1 (en) | 2022-06-09 |
PL3224267T3 (pl) | 2021-07-12 |
CA2958194A1 (en) | 2016-08-18 |
RU2017105212A3 (pt) | 2019-01-11 |
CN106715449B (zh) | 2020-06-16 |
CA2958194C (en) | 2023-10-03 |
US20190194233A1 (en) | 2019-06-27 |
WO2016128812A1 (en) | 2016-08-18 |
KR102502249B1 (ko) | 2023-02-20 |
RU2017105212A (ru) | 2018-12-26 |
KR20170086021A (ko) | 2017-07-25 |
PT3224267T (pt) | 2021-04-07 |
HUE053465T2 (hu) | 2021-06-28 |
BR112017005473B1 (pt) | 2021-09-14 |
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