TWI756328B - 氫氟烯烴及其使用方法 - Google Patents
氫氟烯烴及其使用方法 Download PDFInfo
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- TWI756328B TWI756328B TW106144738A TW106144738A TWI756328B TW I756328 B TWI756328 B TW I756328B TW 106144738 A TW106144738 A TW 106144738A TW 106144738 A TW106144738 A TW 106144738A TW I756328 B TWI756328 B TW I756328B
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- Taiwan
- Prior art keywords
- working fluid
- hydrofluoroolefin
- heat transfer
- hydrofluoroolefin compound
- carbon atoms
- Prior art date
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- 238000000034 method Methods 0.000 title claims description 39
- 150000001875 compounds Chemical class 0.000 claims abstract description 106
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 21
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 17
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 17
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 15
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 14
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 8
- 239000012530 fluid Substances 0.000 claims description 103
- 238000012546 transfer Methods 0.000 claims description 25
- 230000007246 mechanism Effects 0.000 claims description 19
- 239000013529 heat transfer fluid Substances 0.000 claims description 13
- 239000004065 semiconductor Substances 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- UYMKPFRHYYNDTL-UHFFFAOYSA-N ethenamine Chemical compound NC=C UYMKPFRHYYNDTL-UHFFFAOYSA-N 0.000 claims description 5
- 239000000446 fuel Substances 0.000 claims description 5
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 claims description 4
- 150000002466 imines Chemical class 0.000 claims description 3
- 239000011968 lewis acid catalyst Substances 0.000 claims 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 abstract 1
- 239000000203 mixture Substances 0.000 description 119
- -1 metalloid fluorides Chemical class 0.000 description 33
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- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 20
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- 239000007788 liquid Substances 0.000 description 17
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- 239000010702 perfluoropolyether Substances 0.000 description 8
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- 239000006184 cosolvent Substances 0.000 description 7
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- FYWMUSXBRBQLJG-UHFFFAOYSA-N 2,2,3,3,5,5,6,6-octafluoro-4-(1,2,2-trifluoroethenyl)morpholine Chemical compound FC(F)=C(F)N1C(F)(F)C(F)(F)OC(F)(F)C1(F)F FYWMUSXBRBQLJG-UHFFFAOYSA-N 0.000 description 4
- OHMHBGPWCHTMQE-UHFFFAOYSA-N 2,2-dichloro-1,1,1-trifluoroethane Chemical compound FC(F)(F)C(Cl)Cl OHMHBGPWCHTMQE-UHFFFAOYSA-N 0.000 description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
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- 125000001153 fluoro group Chemical group F* 0.000 description 4
- 238000004508 fractional distillation Methods 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- UJMWVICAENGCRF-UHFFFAOYSA-N oxygen difluoride Chemical class FOF UJMWVICAENGCRF-UHFFFAOYSA-N 0.000 description 4
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- 210000002268 wool Anatomy 0.000 description 4
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- 229910021630 Antimony pentafluoride Inorganic materials 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000004793 Polystyrene Substances 0.000 description 3
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 3
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 3
- 239000000853 adhesive Substances 0.000 description 3
- 230000001070 adhesive effect Effects 0.000 description 3
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 3
- VBVBHWZYQGJZLR-UHFFFAOYSA-I antimony pentafluoride Chemical compound F[Sb](F)(F)(F)F VBVBHWZYQGJZLR-UHFFFAOYSA-I 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- 239000003990 capacitor Substances 0.000 description 3
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- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 230000007613 environmental effect Effects 0.000 description 3
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- 229930195729 fatty acid Natural products 0.000 description 3
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- 238000003682 fluorination reaction Methods 0.000 description 3
- 125000005456 glyceride group Chemical group 0.000 description 3
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- 238000007654 immersion Methods 0.000 description 3
- 229910052744 lithium Inorganic materials 0.000 description 3
- 150000001247 metal acetylides Chemical class 0.000 description 3
- LGRLWUINFJPLSH-UHFFFAOYSA-N methanide Chemical compound [CH3-] LGRLWUINFJPLSH-UHFFFAOYSA-N 0.000 description 3
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- 239000002736 nonionic surfactant Substances 0.000 description 3
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- 150000003456 sulfonamides Chemical class 0.000 description 3
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 3
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 3
- ZUHZGEOKBKGPSW-UHFFFAOYSA-N tetraglyme Chemical compound COCCOCCOCCOCCOC ZUHZGEOKBKGPSW-UHFFFAOYSA-N 0.000 description 3
- 235000012431 wafers Nutrition 0.000 description 3
- GRWFGVWFFZKLTI-IUCAKERBSA-N (-)-α-pinene Chemical compound CC1=CC[C@@H]2C(C)(C)[C@H]1C2 GRWFGVWFFZKLTI-IUCAKERBSA-N 0.000 description 2
- GETTZEONDQJALK-UHFFFAOYSA-N (trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC=C1 GETTZEONDQJALK-UHFFFAOYSA-N 0.000 description 2
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical class C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 2
- 238000004293 19F NMR spectroscopy Methods 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- 229910017008 AsF 6 Inorganic materials 0.000 description 2
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- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
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- 239000005977 Ethylene Substances 0.000 description 2
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- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
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- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
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- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- WAIPAZQMEIHHTJ-UHFFFAOYSA-N [Cr].[Co] Chemical compound [Cr].[Co] WAIPAZQMEIHHTJ-UHFFFAOYSA-N 0.000 description 2
- XECAHXYUAAWDEL-UHFFFAOYSA-N acrylonitrile butadiene styrene Chemical compound C=CC=C.C=CC#N.C=CC1=CC=CC=C1 XECAHXYUAAWDEL-UHFFFAOYSA-N 0.000 description 2
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- IAQRGUVFOMOMEM-UHFFFAOYSA-N but-2-ene Chemical compound CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 2
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- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
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- KSUHRWWSNHJRMY-UHFFFAOYSA-N 1,1,1,2,2,4-hexafluorobutane Chemical compound FCCC(F)(F)C(F)(F)F KSUHRWWSNHJRMY-UHFFFAOYSA-N 0.000 description 1
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- UERAGWQPCSLYTB-UHFFFAOYSA-N 1,1,2,2-tetrafluoro-3-methylcyclobutane Chemical compound CC1CC(F)(F)C1(F)F UERAGWQPCSLYTB-UHFFFAOYSA-N 0.000 description 1
- DHZPVNGMSDDSQX-UHFFFAOYSA-N 1,1,2-trifluoro-2-(trifluoromethyl)cyclobutane Chemical compound FC(F)(F)C1(F)CCC1(F)F DHZPVNGMSDDSQX-UHFFFAOYSA-N 0.000 description 1
- FRCHKSNAZZFGCA-UHFFFAOYSA-N 1,1-dichloro-1-fluoroethane Chemical compound CC(F)(Cl)Cl FRCHKSNAZZFGCA-UHFFFAOYSA-N 0.000 description 1
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- UJIGKESMIPTWJH-UHFFFAOYSA-N 1,3-dichloro-1,1,2,2,3-pentafluoropropane Chemical compound FC(Cl)C(F)(F)C(F)(F)Cl UJIGKESMIPTWJH-UHFFFAOYSA-N 0.000 description 1
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- XROWMBWRMNHXMF-UHFFFAOYSA-J titanium tetrafluoride Chemical compound [F-].[F-].[F-].[F-].[Ti+4] XROWMBWRMNHXMF-UHFFFAOYSA-J 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
- C07D265/30—1,4-Oxazines; Hydrogenated 1,4-oxazines not condensed with other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- C09K5/00—Heat-transfer, heat-exchange or heat-storage materials, e.g. refrigerants; Materials for the production of heat or cold by chemical reactions other than by combustion
- C09K5/02—Materials undergoing a change of physical state when used
- C09K5/04—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa
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- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K5/00—Heat-transfer, heat-exchange or heat-storage materials, e.g. refrigerants; Materials for the production of heat or cold by chemical reactions other than by combustion
- C09K5/08—Materials not undergoing a change of physical state when used
- C09K5/10—Liquid materials
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L23/00—Details of semiconductor or other solid state devices
- H01L23/34—Arrangements for cooling, heating, ventilating or temperature compensation ; Temperature sensing arrangements
- H01L23/46—Arrangements for cooling, heating, ventilating or temperature compensation ; Temperature sensing arrangements involving the transfer of heat by flowing fluids
- H01L23/473—Arrangements for cooling, heating, ventilating or temperature compensation ; Temperature sensing arrangements involving the transfer of heat by flowing fluids by flowing liquids
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- Combustion & Propulsion (AREA)
- General Physics & Mathematics (AREA)
- Power Engineering (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Computer Hardware Design (AREA)
- Condensed Matter Physics & Semiconductors (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
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|---|---|---|---|
| US201662437183P | 2016-12-21 | 2016-12-21 | |
| US62/437,183 | 2016-12-21 |
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| TW201835056A TW201835056A (zh) | 2018-10-01 |
| TWI756328B true TWI756328B (zh) | 2022-03-01 |
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| TW106144738A TWI756328B (zh) | 2016-12-21 | 2017-12-20 | 氫氟烯烴及其使用方法 |
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| EP (1) | EP3558915A4 (enExample) |
| JP (1) | JP7120713B2 (enExample) |
| CN (1) | CN110088071A (enExample) |
| TW (1) | TWI756328B (enExample) |
| WO (1) | WO2018116159A1 (enExample) |
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| EP3455322B1 (en) * | 2016-05-09 | 2021-03-03 | 3M Innovative Properties Company | Hydrofluoroolefins and methods of using same |
| EP3460558A1 (en) * | 2017-09-20 | 2019-03-27 | Max-Planck-Gesellschaft zur Förderung der Wissenschaften e.V. | Cryo-light microscope and immersion medium for cryo-light microscopy |
| CN113195674B (zh) * | 2018-12-20 | 2023-09-01 | 3M创新有限公司 | 氢氟烯烃及其使用方法 |
| WO2020132309A1 (en) | 2018-12-21 | 2020-06-25 | Honeywell International Inc. | Solvent compositions containing 1,2,2-trifluoro-1-trifluoromethylcyclobutane (tfmcb) |
| US11996520B2 (en) * | 2020-01-28 | 2024-05-28 | StoreDot Ltd. | Electrolyte additives for fast charging lithium ion batteries |
| KR20250157421A (ko) | 2023-03-08 | 2025-11-04 | 사우스 8 테크놀로지스, 인코포레이티드 | 에너지 저장 디바이스용 전해질 화학적 제형 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4338428A (en) * | 1981-08-14 | 1982-07-06 | The Upjohn Company | Novel polyamides from ketene-aminals |
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|---|---|---|---|---|
| US4536490A (en) * | 1984-03-08 | 1985-08-20 | The Upjohn Company | Catalyst compositions for trimerizing organic isocyanates |
| US4782148A (en) | 1985-07-23 | 1988-11-01 | Agency Of Industrial Science & Technology | Method for production of perfluoro N-(vinyl)amines |
| US4985556A (en) | 1987-09-10 | 1991-01-15 | Agency Of Industrial Science & Technology | Perfluoro(dialkylaminopropene) derivatives |
| JPH0170445U (enExample) | 1987-10-28 | 1989-05-10 | ||
| JPS6470445A (en) | 1988-07-23 | 1989-03-15 | Agency Ind Science Techn | Novel perfluoroalkenylamine and production thereof |
| US6203944B1 (en) | 1998-03-26 | 2001-03-20 | 3M Innovative Properties Company | Electrode for a lithium battery |
| US6255017B1 (en) | 1998-07-10 | 2001-07-03 | 3M Innovative Properties Co. | Electrode material and compositions including same |
| US8820079B2 (en) | 2008-12-05 | 2014-09-02 | Honeywell International Inc. | Chloro- and bromo-fluoro olefin compounds useful as organic rankine cycle working fluids |
| JP6773326B2 (ja) | 2013-12-20 | 2020-10-21 | スリーエム イノベイティブ プロパティズ カンパニー | 作動流体としてのフッ素化オレフィン及びその使用方法 |
| CN107614560A (zh) * | 2015-06-05 | 2018-01-19 | 3M创新有限公司 | 氢氟烯烃及其使用方法 |
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2017
- 2017-12-19 EP EP17883723.3A patent/EP3558915A4/en not_active Withdrawn
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- 2017-12-19 WO PCT/IB2017/058133 patent/WO2018116159A1/en not_active Ceased
- 2017-12-19 CN CN201780078817.2A patent/CN110088071A/zh active Pending
- 2017-12-19 JP JP2019533323A patent/JP7120713B2/ja active Active
- 2017-12-20 TW TW106144738A patent/TWI756328B/zh active
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4338428A (en) * | 1981-08-14 | 1982-07-06 | The Upjohn Company | Novel polyamides from ketene-aminals |
Non-Patent Citations (1)
| Title |
|---|
| David H et al., ".Polyfluoroalkyl Compounds of Silicon. Part Further Silanes containing the Bis(trifluoromethy1)amino-group ", J.C.S. Dalton,18 February ,1974,P 1852–1855. * |
Also Published As
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| US20190337933A1 (en) | 2019-11-07 |
| EP3558915A4 (en) | 2020-07-29 |
| TW201835056A (zh) | 2018-10-01 |
| WO2018116159A1 (en) | 2018-06-28 |
| US11046677B2 (en) | 2021-06-29 |
| CN110088071A (zh) | 2019-08-02 |
| EP3558915A1 (en) | 2019-10-30 |
| JP7120713B2 (ja) | 2022-08-17 |
| JP2020503307A (ja) | 2020-01-30 |
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