GB2508350A - A process for the selective removal of a catalyst from a liquid phase - Google Patents
A process for the selective removal of a catalyst from a liquid phase Download PDFInfo
- Publication number
- GB2508350A GB2508350A GB1221402.9A GB201221402A GB2508350A GB 2508350 A GB2508350 A GB 2508350A GB 201221402 A GB201221402 A GB 201221402A GB 2508350 A GB2508350 A GB 2508350A
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- GB
- United Kingdom
- Prior art keywords
- group
- catalyst
- compound
- formula
- independently
- 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.)
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- 239000003054 catalyst Substances 0.000 title claims abstract description 136
- 238000000034 method Methods 0.000 title claims abstract description 46
- 230000008569 process Effects 0.000 title claims abstract description 36
- 239000007791 liquid phase Substances 0.000 title claims abstract description 20
- 150000001875 compounds Chemical class 0.000 claims abstract description 86
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims abstract description 64
- 239000012429 reaction media Substances 0.000 claims abstract description 58
- 125000003118 aryl group Chemical group 0.000 claims abstract description 34
- 239000000377 silicon dioxide Substances 0.000 claims abstract description 30
- -1 triflate Chemical compound 0.000 claims abstract description 24
- 125000001424 substituent group Chemical group 0.000 claims abstract description 22
- 125000005647 linker group Chemical group 0.000 claims abstract description 13
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims abstract description 9
- 150000002148 esters Chemical class 0.000 claims abstract description 9
- 229920001296 polysiloxane Polymers 0.000 claims abstract description 9
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 8
- 239000002815 homogeneous catalyst Substances 0.000 claims abstract description 7
- 150000002825 nitriles Chemical class 0.000 claims abstract description 7
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 6
- 229910052740 iodine Inorganic materials 0.000 claims abstract description 6
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims abstract description 5
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims abstract description 5
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims abstract description 4
- 238000006243 chemical reaction Methods 0.000 claims description 58
- 229910052751 metal Inorganic materials 0.000 claims description 41
- 239000002184 metal Substances 0.000 claims description 40
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 35
- 125000000217 alkyl group Chemical group 0.000 claims description 34
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 24
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 23
- 229920000642 polymer Polymers 0.000 claims description 20
- 125000001072 heteroaryl group Chemical group 0.000 claims description 19
- 229910052763 palladium Inorganic materials 0.000 claims description 19
- 239000003446 ligand Substances 0.000 claims description 18
- 229910052801 chlorine Inorganic materials 0.000 claims description 15
- 229910052742 iron Inorganic materials 0.000 claims description 14
- 229910052759 nickel Inorganic materials 0.000 claims description 14
- 125000000623 heterocyclic group Chemical group 0.000 claims description 13
- 239000007795 chemical reaction product Substances 0.000 claims description 12
- 125000002524 organometallic group Chemical group 0.000 claims description 12
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 12
- 229910052799 carbon Inorganic materials 0.000 claims description 11
- 125000004429 atom Chemical group 0.000 claims description 10
- 230000015572 biosynthetic process Effects 0.000 claims description 10
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- 239000001301 oxygen Substances 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 239000000047 product Substances 0.000 claims description 10
- 125000002577 pseudohalo group Chemical group 0.000 claims description 10
- 229910052802 copper Inorganic materials 0.000 claims description 9
- 239000010949 copper Substances 0.000 claims description 9
- 229910052731 fluorine Inorganic materials 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 8
- 229910052741 iridium Inorganic materials 0.000 claims description 8
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 8
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 8
- 125000000304 alkynyl group Chemical group 0.000 claims description 7
- 150000001412 amines Chemical class 0.000 claims description 7
- 229910052697 platinum Inorganic materials 0.000 claims description 7
- 229910052703 rhodium Inorganic materials 0.000 claims description 7
- 239000010948 rhodium Substances 0.000 claims description 7
- 229910052707 ruthenium Inorganic materials 0.000 claims description 7
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 7
- 229920002554 vinyl polymer Polymers 0.000 claims description 7
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 6
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 6
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 238000005576 amination reaction Methods 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 229910052796 boron Inorganic materials 0.000 claims description 6
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 6
- 125000005842 heteroatom Chemical group 0.000 claims description 6
- 229910052710 silicon Inorganic materials 0.000 claims description 6
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 5
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 5
- 238000004132 cross linking Methods 0.000 claims description 5
- 230000000694 effects Effects 0.000 claims description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 5
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims description 5
- 229910052749 magnesium Inorganic materials 0.000 claims description 5
- 239000011777 magnesium Substances 0.000 claims description 5
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 5
- 238000007341 Heck reaction Methods 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 4
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims description 4
- 125000002252 acyl group Chemical group 0.000 claims description 4
- 238000005810 carbonylation reaction Methods 0.000 claims description 4
- 238000006266 etherification reaction Methods 0.000 claims description 4
- 150000004820 halides Chemical class 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052747 lanthanoid Inorganic materials 0.000 claims description 4
- 150000002602 lanthanoids Chemical class 0.000 claims description 4
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 claims description 4
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 4
- 229910052726 zirconium Inorganic materials 0.000 claims description 4
- 125000000520 N-substituted aminocarbonyl group Chemical group [*]NC(=O)* 0.000 claims description 3
- 238000006795 borylation reaction Methods 0.000 claims description 3
- 230000006315 carbonylation Effects 0.000 claims description 3
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 claims description 3
- 230000002829 reductive effect Effects 0.000 claims description 3
- 150000003457 sulfones Chemical class 0.000 claims description 3
- 150000003462 sulfoxides Chemical class 0.000 claims description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 2
- 238000006443 Buchwald-Hartwig cross coupling reaction Methods 0.000 claims description 2
- 238000006639 Goldberg reaction Methods 0.000 claims description 2
- 238000006716 Hiyama reaction Methods 0.000 claims description 2
- 238000006411 Negishi coupling reaction Methods 0.000 claims description 2
- 238000003477 Sonogashira cross-coupling reaction Methods 0.000 claims description 2
- 238000006619 Stille reaction Methods 0.000 claims description 2
- 238000006161 Suzuki-Miyaura coupling reaction Methods 0.000 claims description 2
- 238000006579 Tsuji-Trost allylation reaction Methods 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 claims description 2
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- YNHIGQDRGKUECZ-UHFFFAOYSA-N dichloropalladium;triphenylphosphanium Chemical compound Cl[Pd]Cl.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000005594 diketone group Chemical group 0.000 claims description 2
- 125000003106 haloaryl group Chemical group 0.000 claims description 2
- 238000007037 hydroformylation reaction Methods 0.000 claims description 2
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical group [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 claims description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
- 229910052723 transition metal Inorganic materials 0.000 claims description 2
- 150000003624 transition metals Chemical class 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- RRKODOZNUZCUBN-CCAGOZQPSA-N (1z,3z)-cycloocta-1,3-diene Chemical compound C1CC\C=C/C=C\C1 RRKODOZNUZCUBN-CCAGOZQPSA-N 0.000 claims 1
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 claims 1
- 125000004799 bromophenyl group Chemical group 0.000 claims 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 1
- 125000001188 haloalkyl group Chemical group 0.000 claims 1
- 125000005216 haloheteroaryl group Chemical group 0.000 claims 1
- 239000002243 precursor Substances 0.000 claims 1
- 125000000524 functional group Chemical group 0.000 abstract description 9
- 238000006069 Suzuki reaction reaction Methods 0.000 abstract description 4
- 238000006880 cross-coupling reaction Methods 0.000 abstract description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
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Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1221402.9A GB2508350A (en) | 2012-11-28 | 2012-11-28 | A process for the selective removal of a catalyst from a liquid phase |
| JP2015544460A JP6310475B2 (ja) | 2012-11-28 | 2013-11-28 | 触媒を除去して液相媒体に戻す方法 |
| PCT/EP2013/074974 WO2014083109A2 (en) | 2012-11-28 | 2013-11-28 | Process for the removal and return of a catalyst to a liquid phase medium |
| CN201380067936.XA CN104884506B (zh) | 2012-11-28 | 2013-11-28 | 将催化剂移除并返回至液相介质中的方法 |
| US14/647,919 US10519173B2 (en) | 2012-11-28 | 2013-11-28 | Process for the removal and return of a catalyst to a liquid phase medium |
| GB1511333.5A GB2528778B (en) | 2012-11-28 | 2013-11-28 | Process for the removal and return of a catalyst to a liquid phase medium |
| PCT/EP2013/074984 WO2014083112A1 (en) | 2012-11-28 | 2013-11-28 | Supported compound comprising linker and leaving group |
| EP13824490.0A EP2925438A2 (en) | 2012-11-28 | 2013-11-28 | Process for the removal and return of a catalyst to a liquid phase medium and its use in cross-coupling reactions |
| US16/707,816 US20200255457A1 (en) | 2012-11-28 | 2019-12-09 | Process for the removal and return of a catalyst to a liquid phase medium |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1221402.9A GB2508350A (en) | 2012-11-28 | 2012-11-28 | A process for the selective removal of a catalyst from a liquid phase |
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| GB201221402D0 GB201221402D0 (en) | 2013-01-09 |
| GB2508350A true GB2508350A (en) | 2014-06-04 |
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| GB1511333.5A Expired - Fee Related GB2528778B (en) | 2012-11-28 | 2013-11-28 | Process for the removal and return of a catalyst to a liquid phase medium |
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| GB1511333.5A Expired - Fee Related GB2528778B (en) | 2012-11-28 | 2013-11-28 | Process for the removal and return of a catalyst to a liquid phase medium |
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| US (2) | US10519173B2 (https=) |
| EP (1) | EP2925438A2 (https=) |
| JP (1) | JP6310475B2 (https=) |
| CN (1) | CN104884506B (https=) |
| GB (2) | GB2508350A (https=) |
| WO (2) | WO2014083109A2 (https=) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US10618037B2 (en) | 2015-06-24 | 2020-04-14 | Zeon Corporation | Method for recovering catalyst |
| CN113797978B (zh) * | 2021-10-12 | 2023-11-07 | 青岛科技大学 | 一类聚三芳基氧膦负载钯/铜双金属催化剂的制备方法及应用 |
| CN115805102B (zh) * | 2022-11-25 | 2024-04-05 | 中科合成油技术股份有限公司 | 一种用于中长链α-烯烃氢甲酰化制高碳醛的多相催化剂及其制备方法 |
| CN119565677A (zh) * | 2024-11-22 | 2025-03-07 | 中国石油化工股份有限公司 | 一种多孔催化剂及其制备方法与应用 |
Citations (6)
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| WO2006013080A1 (en) * | 2004-08-04 | 2006-02-09 | Phosphonics Ltd | Substituted organopolysiloxanes and use thereof |
| WO2007006569A1 (en) * | 2005-07-14 | 2007-01-18 | Phosphonics Ltd | Substituted organopolysiloxanes containing phosphonic groups, methods for the production and use thereof |
| US20090220449A1 (en) * | 2006-02-10 | 2009-09-03 | Phosphonics Ltd | Substituted organopolysiloxanes and uses thereof |
| US20100290962A1 (en) * | 2007-10-20 | 2010-11-18 | Phosphonics Ltd | Functionalised materials and uses thereof |
| WO2011128061A1 (en) * | 2010-04-15 | 2011-10-20 | Phosphonics Ltd | Functionalised materials and uses thereof |
| WO2012095307A1 (en) * | 2011-01-13 | 2012-07-19 | Phosphonics Ltd | Functionalised materials, process for the production and uses thereof |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4032597A1 (de) * | 1990-10-13 | 1992-04-16 | Bayer Ag | Rueckgewinnung von hydrierkatalysatoren aus loesungen von hydriertem nitrilkautschuk |
| US7264728B2 (en) * | 2002-10-01 | 2007-09-04 | Dow Corning Corporation | Method of separating components in a sample using silane-treated silica filter media |
| US9982095B2 (en) * | 2004-08-04 | 2018-05-29 | Phosphonics Ltd | Substituted organopolysiloxanes and use thereof |
| GB0417345D0 (en) * | 2004-08-04 | 2004-09-08 | Phosphonics Ltd | Substituted organopolysiloxanes and uses thereof |
| JP5387228B2 (ja) * | 2009-08-21 | 2014-01-15 | 東ソー株式会社 | 溶存パラジウムの除去方法 |
-
2012
- 2012-11-28 GB GB1221402.9A patent/GB2508350A/en not_active Withdrawn
-
2013
- 2013-11-28 GB GB1511333.5A patent/GB2528778B/en not_active Expired - Fee Related
- 2013-11-28 EP EP13824490.0A patent/EP2925438A2/en not_active Withdrawn
- 2013-11-28 CN CN201380067936.XA patent/CN104884506B/zh not_active Expired - Fee Related
- 2013-11-28 WO PCT/EP2013/074974 patent/WO2014083109A2/en not_active Ceased
- 2013-11-28 US US14/647,919 patent/US10519173B2/en active Active
- 2013-11-28 JP JP2015544460A patent/JP6310475B2/ja not_active Expired - Fee Related
- 2013-11-28 WO PCT/EP2013/074984 patent/WO2014083112A1/en not_active Ceased
-
2019
- 2019-12-09 US US16/707,816 patent/US20200255457A1/en not_active Abandoned
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006013080A1 (en) * | 2004-08-04 | 2006-02-09 | Phosphonics Ltd | Substituted organopolysiloxanes and use thereof |
| WO2007006569A1 (en) * | 2005-07-14 | 2007-01-18 | Phosphonics Ltd | Substituted organopolysiloxanes containing phosphonic groups, methods for the production and use thereof |
| US20090220449A1 (en) * | 2006-02-10 | 2009-09-03 | Phosphonics Ltd | Substituted organopolysiloxanes and uses thereof |
| US20100290962A1 (en) * | 2007-10-20 | 2010-11-18 | Phosphonics Ltd | Functionalised materials and uses thereof |
| WO2011128061A1 (en) * | 2010-04-15 | 2011-10-20 | Phosphonics Ltd | Functionalised materials and uses thereof |
| WO2012095307A1 (en) * | 2011-01-13 | 2012-07-19 | Phosphonics Ltd | Functionalised materials, process for the production and uses thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2016501717A (ja) | 2016-01-21 |
| WO2014083109A3 (en) | 2014-11-20 |
| US20200255457A1 (en) | 2020-08-13 |
| GB2528778A (en) | 2016-02-03 |
| GB201511333D0 (en) | 2015-08-12 |
| GB201221402D0 (en) | 2013-01-09 |
| WO2014083109A2 (en) | 2014-06-05 |
| JP6310475B2 (ja) | 2018-04-11 |
| WO2014083112A1 (en) | 2014-06-05 |
| CN104884506B (zh) | 2021-10-19 |
| US10519173B2 (en) | 2019-12-31 |
| GB2528778B (en) | 2018-04-11 |
| US20150299229A1 (en) | 2015-10-22 |
| CN104884506A (zh) | 2015-09-02 |
| EP2925438A2 (en) | 2015-10-07 |
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