JP6835060B2 - シクロブテンの製造方法 - Google Patents
シクロブテンの製造方法 Download PDFInfo
- Publication number
- JP6835060B2 JP6835060B2 JP2018245665A JP2018245665A JP6835060B2 JP 6835060 B2 JP6835060 B2 JP 6835060B2 JP 2018245665 A JP2018245665 A JP 2018245665A JP 2018245665 A JP2018245665 A JP 2018245665A JP 6835060 B2 JP6835060 B2 JP 6835060B2
- Authority
- JP
- Japan
- Prior art keywords
- oxide
- fluoride
- halogen atom
- reaction
- catalyst
- 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.)
- Active
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- CFBGXYDUODCMNS-UHFFFAOYSA-N cyclobutene Chemical compound C1CC=C1 CFBGXYDUODCMNS-UHFFFAOYSA-N 0.000 title claims description 45
- 238000004519 manufacturing process Methods 0.000 title claims description 17
- 238000006243 chemical reaction Methods 0.000 claims description 67
- 125000005843 halogen group Chemical group 0.000 claims description 66
- 239000003054 catalyst Substances 0.000 claims description 59
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 33
- 239000007789 gas Substances 0.000 claims description 32
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 29
- 238000003379 elimination reaction Methods 0.000 claims description 21
- 238000003795 desorption Methods 0.000 claims description 19
- 229910000423 chromium oxide Inorganic materials 0.000 claims description 18
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 17
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 claims description 15
- 229910052751 metal Inorganic materials 0.000 claims description 12
- 239000002184 metal Substances 0.000 claims description 12
- PMPVIKIVABFJJI-UHFFFAOYSA-N Cyclobutane Chemical compound C1CCC1 PMPVIKIVABFJJI-UHFFFAOYSA-N 0.000 claims description 11
- 229910021563 chromium fluoride Inorganic materials 0.000 claims description 8
- FTBATIJJKIIOTP-UHFFFAOYSA-K trifluorochromium Chemical compound F[Cr](F)F FTBATIJJKIIOTP-UHFFFAOYSA-K 0.000 claims description 8
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 7
- IRPGOXJVTQTAAN-UHFFFAOYSA-N 2,2,3,3,3-pentafluoropropanal Chemical compound FC(F)(F)C(F)(F)C=O IRPGOXJVTQTAAN-UHFFFAOYSA-N 0.000 claims description 6
- KLZUFWVZNOTSEM-UHFFFAOYSA-K Aluminum fluoride Inorganic materials F[Al](F)F KLZUFWVZNOTSEM-UHFFFAOYSA-K 0.000 claims description 6
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 claims description 6
- SHXXPRJOPFJRHA-UHFFFAOYSA-K iron(iii) fluoride Chemical compound F[Fe](F)F SHXXPRJOPFJRHA-UHFFFAOYSA-K 0.000 claims description 5
- ORUIBWPALBXDOA-UHFFFAOYSA-L magnesium fluoride Chemical compound [F-].[F-].[Mg+2] ORUIBWPALBXDOA-UHFFFAOYSA-L 0.000 claims description 5
- 229910001635 magnesium fluoride Inorganic materials 0.000 claims description 5
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims description 5
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 4
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 claims description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 3
- 239000000395 magnesium oxide Substances 0.000 claims description 3
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 claims description 3
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 claims description 3
- 229910000480 nickel oxide Inorganic materials 0.000 claims description 3
- GNRSAWUEBMWBQH-UHFFFAOYSA-N oxonickel Chemical compound [Ni]=O GNRSAWUEBMWBQH-UHFFFAOYSA-N 0.000 claims description 3
- DXSOBOFFMLHPRJ-UHFFFAOYSA-L [Ni](F)(F)=O Chemical compound [Ni](F)(F)=O DXSOBOFFMLHPRJ-UHFFFAOYSA-L 0.000 claims description 2
- 229910003481 amorphous carbon Inorganic materials 0.000 claims description 2
- 238000006704 dehydrohalogenation reaction Methods 0.000 claims description 2
- 229910003460 diamond Inorganic materials 0.000 claims description 2
- 239000010432 diamond Substances 0.000 claims description 2
- 229910002804 graphite Inorganic materials 0.000 claims description 2
- 239000010439 graphite Substances 0.000 claims description 2
- DBJLJFTWODWSOF-UHFFFAOYSA-L nickel(ii) fluoride Chemical compound F[Ni]F DBJLJFTWODWSOF-UHFFFAOYSA-L 0.000 claims 2
- 239000000377 silicon dioxide Substances 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 57
- 239000002994 raw material Substances 0.000 description 33
- 125000001153 fluoro group Chemical group F* 0.000 description 21
- 229910052731 fluorine Inorganic materials 0.000 description 20
- 239000000203 mixture Substances 0.000 description 20
- 239000012071 phase Substances 0.000 description 15
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 10
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 9
- UOUJSJZBMCDAEU-UHFFFAOYSA-N chromium(3+);oxygen(2-) Chemical class [O-2].[O-2].[O-2].[Cr+3].[Cr+3] UOUJSJZBMCDAEU-UHFFFAOYSA-N 0.000 description 8
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 6
- 238000003682 fluorination reaction Methods 0.000 description 6
- 239000011737 fluorine Substances 0.000 description 6
- 238000004949 mass spectrometry Methods 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 238000012916 structural analysis Methods 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- 239000011261 inert gas Substances 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 238000009826 distribution Methods 0.000 description 3
- 238000005530 etching Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- -1 and Y is Chemical group 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- 239000011651 chromium Substances 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 125000003709 fluoroalkyl group Chemical group 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 239000004065 semiconductor Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 238000004438 BET method Methods 0.000 description 1
- 239000004484 Briquette Substances 0.000 description 1
- LMSLTAIWOIYSGZ-UHFFFAOYSA-N FC(C(C1(F)F)F)C1(F)F Chemical compound FC(C(C1(F)F)F)C1(F)F LMSLTAIWOIYSGZ-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- 229910001030 Iron–nickel alloy Inorganic materials 0.000 description 1
- 229910010413 TiO 2 Inorganic materials 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000012459 cleaning agent Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 150000001930 cyclobutanes Chemical class 0.000 description 1
- 150000001931 cyclobutenes Chemical class 0.000 description 1
- 125000001047 cyclobutenyl group Chemical group C1(=CCC1)* 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 238000001312 dry etching Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000004088 foaming agent Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 1
- 238000010574 gas phase reaction Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 239000002440 industrial waste Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 150000003961 organosilicon compounds Chemical class 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 239000012450 pharmaceutical intermediate Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 238000004445 quantitative analysis Methods 0.000 description 1
- 239000003507 refrigerant Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/25—Preparation of halogenated hydrocarbons by splitting-off hydrogen halides from halogenated hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/35—Preparation of halogenated hydrocarbons by reactions not affecting the number of carbon or of halogen atoms in the reaction
- C07C17/357—Preparation of halogenated hydrocarbons by reactions not affecting the number of carbon or of halogen atoms in the reaction by dehydrogenation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C23/00—Compounds containing at least one halogen atom bound to a ring other than a six-membered aromatic ring
- C07C23/02—Monocyclic halogenated hydrocarbons
- C07C23/06—Monocyclic halogenated hydrocarbons with a four-membered ring
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/04—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer
- H01L21/18—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer the devices having semiconductor bodies comprising elements of Group IV of the Periodic Table or AIIIBV compounds with or without impurities, e.g. doping materials
- H01L21/30—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26
- H01L21/302—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26 to change their surface-physical characteristics or shape, e.g. etching, polishing, cutting
- H01L21/306—Chemical or electrical treatment, e.g. electrolytic etching
- H01L21/3065—Plasma etching; Reactive-ion etching
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Physics & Mathematics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Condensed Matter Physics & Semiconductors (AREA)
- Plasma & Fusion (AREA)
- General Physics & Mathematics (AREA)
- Manufacturing & Machinery (AREA)
- Computer Hardware Design (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Power Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2018245665A JP6835060B2 (ja) | 2018-12-27 | 2018-12-27 | シクロブテンの製造方法 |
| SG11202106891PA SG11202106891PA (en) | 2018-12-27 | 2019-12-19 | Method for producing cyclobutene |
| CN201980086441.9A CN113227026A (zh) | 2018-12-27 | 2019-12-19 | 环丁烯的制造方法 |
| KR1020217023297A KR102566765B1 (ko) | 2018-12-27 | 2019-12-19 | 시클로부텐의 제조 방법 |
| PCT/JP2019/049900 WO2020137825A1 (ja) | 2018-12-27 | 2019-12-19 | シクロブテンの製造方法 |
| TW108147731A TWI777113B (zh) | 2018-12-27 | 2019-12-26 | 環丁烯之製造方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2018245665A JP6835060B2 (ja) | 2018-12-27 | 2018-12-27 | シクロブテンの製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2020105114A JP2020105114A (ja) | 2020-07-09 |
| JP6835060B2 true JP6835060B2 (ja) | 2021-02-24 |
Family
ID=71127736
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018245665A Active JP6835060B2 (ja) | 2018-12-27 | 2018-12-27 | シクロブテンの製造方法 |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JP6835060B2 (ko) |
| KR (1) | KR102566765B1 (ko) |
| CN (1) | CN113227026A (ko) |
| SG (1) | SG11202106891PA (ko) |
| TW (1) | TWI777113B (ko) |
| WO (1) | WO2020137825A1 (ko) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2023049515A1 (en) * | 2021-09-27 | 2023-03-30 | Honeywell International Inc. | Fluorine substituted cyclobutene compounds, and compositions, methods and uses including same |
| CN118139944A (zh) * | 2021-09-27 | 2024-06-04 | 霍尼韦尔国际公司 | 氟取代的环丁烯化合物以及包含其的组合物、方法和用途 |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2891968A (en) * | 1955-08-12 | 1959-06-23 | Du Pont | Difluorobutenedioic acids, their alkali metal salts, their alkyl esters and anhydride, and process for preparing them |
| GB844604A (en) * | 1955-09-14 | 1960-08-17 | Robert Neville Haszeldine | Halogenated organic compounds |
| JPH07100673B2 (ja) * | 1986-08-19 | 1995-11-01 | 旭化成工業株式会社 | １−フルオロシクロヘキセンの製造法 |
| KR940002713B1 (ko) * | 1991-12-03 | 1994-03-31 | 주식회사 코오롱 | 디아조타입 감광체 원료의 제조방법 |
| TWI298716B (ko) * | 2001-08-06 | 2008-07-11 | Showa Denko Kk | |
| US7560602B2 (en) * | 2005-11-03 | 2009-07-14 | Honeywell International Inc. | Process for manufacture of fluorinated olefins |
| WO2010007968A1 (ja) * | 2008-07-18 | 2010-01-21 | 日本ゼオン株式会社 | 含水素フルオロオレフィン化合物の製造方法 |
| JP5311009B2 (ja) * | 2008-08-14 | 2013-10-09 | 日本ゼオン株式会社 | 含水素フルオロオレフィン化合物の製造方法 |
| JP5158366B2 (ja) * | 2008-11-25 | 2013-03-06 | 日本ゼオン株式会社 | 含水素フルオロオレフィン化合物の製造方法 |
| JP5056963B2 (ja) * | 2010-03-31 | 2012-10-24 | ダイキン工業株式会社 | 含フッ素アルカンの製造方法 |
| US8921622B2 (en) * | 2010-04-02 | 2014-12-30 | Solvay Sa | Process for dehydrofluorinating hydrochlorofluoroalkanes and products obtained thereby |
| JP5984796B2 (ja) * | 2010-05-03 | 2016-09-06 | アーケマ・インコーポレイテッド | ペンタフルオロアルカンの脱フッ化水素化反応によるテトラフルオロオレフィンの形成 |
| CN102836722B (zh) * | 2012-09-06 | 2014-10-15 | 西安近代化学研究所 | 一种卤氟烷烃脱卤化氢制备含氟烯烃的催化剂及其制备方法 |
| KR102258218B1 (ko) * | 2013-08-26 | 2021-05-28 | 에이지씨 가부시키가이샤 | 함불소 화합물의 제조 방법 |
| CN105107533B (zh) * | 2015-08-18 | 2019-04-09 | 巨化集团技术中心 | 一种气相脱氟化氢催化剂的制备方法 |
| CN107739294B (zh) * | 2017-10-17 | 2020-08-21 | 北京宇极科技发展有限公司 | 气相脱氟化氢制备氢氟环戊烯的方法 |
| CN107721810B (zh) * | 2017-11-07 | 2020-12-01 | 中国民航大学 | 一种合成灭火剂八氟环丁烷的方法 |
| JP7166911B2 (ja) * | 2018-12-25 | 2022-11-08 | ダイキン工業株式会社 | シクロブテンの製造方法 |
-
2018
- 2018-12-27 JP JP2018245665A patent/JP6835060B2/ja active Active
-
2019
- 2019-12-19 SG SG11202106891PA patent/SG11202106891PA/en unknown
- 2019-12-19 WO PCT/JP2019/049900 patent/WO2020137825A1/ja active Application Filing
- 2019-12-19 CN CN201980086441.9A patent/CN113227026A/zh active Pending
- 2019-12-19 KR KR1020217023297A patent/KR102566765B1/ko active IP Right Grant
- 2019-12-26 TW TW108147731A patent/TWI777113B/zh active
Also Published As
| Publication number | Publication date |
|---|---|
| SG11202106891PA (en) | 2021-07-29 |
| JP2020105114A (ja) | 2020-07-09 |
| KR20210108993A (ko) | 2021-09-03 |
| CN113227026A (zh) | 2021-08-06 |
| TWI777113B (zh) | 2022-09-11 |
| WO2020137825A1 (ja) | 2020-07-02 |
| TW202035349A (zh) | 2020-10-01 |
| KR102566765B1 (ko) | 2023-08-16 |
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