JP2010532760A5 - - Google Patents
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- Publication number
- JP2010532760A5 JP2010532760A5 JP2010515208A JP2010515208A JP2010532760A5 JP 2010532760 A5 JP2010532760 A5 JP 2010532760A5 JP 2010515208 A JP2010515208 A JP 2010515208A JP 2010515208 A JP2010515208 A JP 2010515208A JP 2010532760 A5 JP2010532760 A5 JP 2010532760A5
- Authority
- JP
- Japan
- Prior art keywords
- copper
- chlorofluoroalkene
- nickel
- calcium fluoride
- catalyst composition
- 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.)
- Granted
Links
- 238000000034 method Methods 0.000 claims description 17
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 16
- 239000010949 copper Substances 0.000 claims description 16
- 239000003054 catalyst Substances 0.000 claims description 14
- 229910052802 copper Inorganic materials 0.000 claims description 14
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 13
- WUKWITHWXAAZEY-UHFFFAOYSA-L calcium difluoride Chemical compound [F-].[F-].[Ca+2] WUKWITHWXAAZEY-UHFFFAOYSA-L 0.000 claims description 11
- 229910001634 calcium fluoride Inorganic materials 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052763 palladium Inorganic materials 0.000 claims description 6
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 5
- 150000001336 alkenes Chemical class 0.000 claims description 5
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- 239000011737 fluorine Substances 0.000 claims description 5
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 4
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 238000006467 substitution reaction Methods 0.000 claims description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 24
- 229910052759 nickel Inorganic materials 0.000 description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 9
- 229910052799 carbon Inorganic materials 0.000 description 9
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 5
- 230000008901 benefit Effects 0.000 description 5
- 239000011651 chromium Substances 0.000 description 5
- 229910021563 chromium fluoride Inorganic materials 0.000 description 3
- 229910021594 Copper(II) fluoride Inorganic materials 0.000 description 2
- 229910000881 Cu alloy Inorganic materials 0.000 description 2
- 229910000990 Ni alloy Inorganic materials 0.000 description 2
- 229910052804 chromium Inorganic materials 0.000 description 2
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- WDIHJSXYQDMJHN-UHFFFAOYSA-L barium chloride Chemical compound [Cl-].[Cl-].[Ba+2] WDIHJSXYQDMJHN-UHFFFAOYSA-L 0.000 description 1
- 229910001626 barium chloride Inorganic materials 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 239000011981 lindlar catalyst Substances 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US95819007P | 2007-07-03 | 2007-07-03 | |
| US60/958,190 | 2007-07-03 | ||
| US451807P | 2007-11-27 | 2007-11-27 | |
| US61/004,518 | 2007-11-27 | ||
| PCT/US2008/068695 WO2009006358A1 (en) | 2007-07-03 | 2008-06-30 | Method of hydrodechlorination to produce dihydrofluorinated olefins |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014240840A Division JP2015061861A (ja) | 2007-07-03 | 2014-11-28 | ジヒドロフッ素化オレフィンを製造するための水素化脱塩素方法 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2010532760A JP2010532760A (ja) | 2010-10-14 |
| JP2010532760A5 true JP2010532760A5 (enExample) | 2011-07-21 |
| JP5660891B2 JP5660891B2 (ja) | 2015-01-28 |
Family
ID=39942915
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010515208A Active JP5660891B2 (ja) | 2007-07-03 | 2008-06-30 | ジヒドロフッ素化オレフィンを製造するための水素化脱塩素方法 |
| JP2014240840A Pending JP2015061861A (ja) | 2007-07-03 | 2014-11-28 | ジヒドロフッ素化オレフィンを製造するための水素化脱塩素方法 |
| JP2016229714A Pending JP2017075162A (ja) | 2007-07-03 | 2016-11-28 | ジヒドロフッ素化オレフィンを製造するための水素化脱塩素方法 |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014240840A Pending JP2015061861A (ja) | 2007-07-03 | 2014-11-28 | ジヒドロフッ素化オレフィンを製造するための水素化脱塩素方法 |
| JP2016229714A Pending JP2017075162A (ja) | 2007-07-03 | 2016-11-28 | ジヒドロフッ素化オレフィンを製造するための水素化脱塩素方法 |
Country Status (11)
| Country | Link |
|---|---|
| US (3) | US7795482B2 (enExample) |
| EP (1) | EP2173693B1 (enExample) |
| JP (3) | JP5660891B2 (enExample) |
| KR (1) | KR20100046147A (enExample) |
| CN (2) | CN101687736B (enExample) |
| BR (1) | BRPI0810961A2 (enExample) |
| CA (1) | CA2686603A1 (enExample) |
| ES (1) | ES2443024T3 (enExample) |
| RU (1) | RU2476414C2 (enExample) |
| TW (1) | TW200922906A (enExample) |
| WO (1) | WO2009006358A1 (enExample) |
Families Citing this family (47)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7795482B2 (en) | 2007-07-03 | 2010-09-14 | E. I. Du Pont De Nemours And Company | Method of hydrodechlorination to produce dihydrofluorinated olefins |
| US7641808B2 (en) * | 2007-08-23 | 2010-01-05 | E.I. Du Pont De Nemours And Company | Azeotropic compositions comprising fluorinated olefins for cleaning applications |
| US8399721B2 (en) * | 2008-12-22 | 2013-03-19 | E I Du Pont De Nemours And Company | Method of hydrodechlorination to produce dihydrofluorinated olefins |
| CN102459498B (zh) | 2009-06-03 | 2016-08-24 | 纳幕尔杜邦公司 | 含有顺式-1,1,1,4,4,4-六氟-2-丁烯的冷却器设备及其制冷方法 |
| ES2582406T3 (es) | 2009-09-16 | 2016-09-12 | The Chemours Company Fc, Llc | Aparato que comprende cis-1,1,1,4,4,4-hexafluoro-2-buteno y trans-1,2-dicloroetileno y procedimientos para producir enfriamiento en él |
| US9217100B2 (en) | 2009-09-16 | 2015-12-22 | The Chemours Company Fc, Llc | Chiller apparatus containing trans-1,1,1,4,4,4-hexafluoro-2-butene and methods of producing cooling therein |
| US20110144216A1 (en) * | 2009-12-16 | 2011-06-16 | Honeywell International Inc. | Compositions and uses of cis-1,1,1,4,4,4-hexafluoro-2-butene |
| US20110269860A1 (en) | 2010-04-28 | 2011-11-03 | E.I. Du Pont De Nemours And Company | Foam expansion agent compositions containing hydrohaloolefin butene and water and their uses in the preparation of polyurethane and polyisocyanurate polymer foams |
| US8524955B2 (en) * | 2010-05-21 | 2013-09-03 | Honeywell International Inc. | Process for the preparation of hexafluoro-2-butyne |
| US8604257B2 (en) * | 2010-05-21 | 2013-12-10 | Honeywell International Inc. | Process for the preparation of fluorinated cis-alkene |
| CN101961658B (zh) * | 2010-09-07 | 2013-03-06 | 西安近代化学研究所 | 氟化钙基氟化催化剂及其用途 |
| WO2012061022A2 (en) * | 2010-11-02 | 2012-05-10 | E. I. Du Pont De Nemours And Company | Use of copper-nickel catalyst for dehalogenation of chlorofluorocompounds |
| WO2012064477A2 (en) | 2010-11-10 | 2012-05-18 | E. I. Du Pont De Nemours And Company | Compositions comprising cis-1,1,1,4,4,4-hexafluoro-2-butene and 2-difluoromethoxy-1,1,1,2-tetrafluoroethane and uses thereof |
| ES2989330T3 (es) | 2011-08-19 | 2024-11-26 | Chemours Co Fc Llc | Proceso de ciclos de Rankine orgánicos para generar energía mecánica a partir de calor |
| US9003797B2 (en) | 2011-11-02 | 2015-04-14 | E L Du Pont De Nemours And Company | Use of compositions comprising 1,1,1,2,3-pentafluoropropane and optionally Z-1,1,1,4,4,4-hexafluoro-2-butene in power cycles |
| US20130104573A1 (en) | 2011-11-02 | 2013-05-02 | E I Du Pont De Nemours And Company | Use of compositions comprising 1,1,1,2,3-pentafluoropropane and optionally z-1,1,1,4,4,4-hexafluoro-2-butene in chillers |
| US20130104575A1 (en) | 2011-11-02 | 2013-05-02 | E I Du Pont De Nemours And Company | Use of compositions comprising 1,1,1,2,3-pentafluoropropane and optionally z-1,1,1,4,4,4-hexafluoro-2-butene in high temperature heat pumps |
| AU2012346370B2 (en) | 2011-12-02 | 2016-07-14 | The Chemours Company Fc, Llc. | Foam expansion agent compositions containing Z-1,1,1,4,4,4-hexafluoro-2-butene and their uses in the preparation of polyurethane and polyisocyanurate polymer foams |
| JP6224622B2 (ja) * | 2012-01-09 | 2017-11-01 | ザ ケマーズ カンパニー エフシー リミテッド ライアビリティ カンパニー | 反応器パッシベーションのための方法 |
| EP2814580A1 (en) * | 2012-02-17 | 2014-12-24 | E. I. Du Pont de Nemours and Company | Azeotrope-like compositions of z-1,1,1,4,4,4-hexafluoro-2-butene and e-1,1,1,4,4,4-hexafluoro-2-butene and uses thereof |
| JP5817591B2 (ja) * | 2012-03-01 | 2015-11-18 | 旭硝子株式会社 | 2,3,3,3−テトラフルオロプロペンの製造方法 |
| CN103373896B (zh) * | 2012-04-13 | 2015-03-18 | 中化蓝天集团有限公司 | 一种1,1,1,4,4,4-六氟-2-丁烯的制备方法 |
| TW201413192A (zh) * | 2012-08-01 | 2014-04-01 | Du Pont | E-1,1,1,4,4,4-六氟-2-丁烯在熱泵的使用 |
| JP6570078B2 (ja) | 2014-02-07 | 2019-09-04 | ザ ケマーズ カンパニー エフシー リミテッド ライアビリティ カンパニー | Z−1,1,1,4,4,4−ヘキサフルオロ−2−ブテンを生成するための統合方法 |
| WO2015160532A1 (en) | 2014-04-16 | 2015-10-22 | The Chemours Company Fc, Llc | Conversion of chlorofluororopanes and chlorofluropropenes to more desirable fluoropropanes and fluororopenes |
| JP6477712B2 (ja) * | 2014-08-25 | 2019-03-06 | Agc株式会社 | ハイドロフルオロオレフィンの製造方法 |
| EP3187477A4 (en) * | 2014-08-25 | 2018-04-11 | Asahi Glass Company, Limited | Process for producing hydrofluoroolefin |
| EP3253844B1 (en) | 2015-02-06 | 2022-06-22 | The Chemours Company FC, LLC | Compositions comprising z-1,1,1,4,4,4-hexafluoro-2-butene and uses thereof |
| CN112920777A (zh) | 2015-02-06 | 2021-06-08 | 科慕埃弗西有限公司 | 包含e-1,1,1,4,4,4-六氟-2-丁烯的组合物及其用途 |
| WO2017027323A1 (en) | 2015-08-07 | 2017-02-16 | The Chemours Company Fc, Llc | Catalytic isomerization of z-1,1,1,4,4,4-hexafluoro-2-butene to e-1,1,1,4,4,4-hexafluoro-2-butene |
| EP3405516B1 (en) * | 2016-01-22 | 2022-03-02 | The Chemours Company FC, LLC | Foaming of a reaction product of a polyisocyanate and an active hydrogen-containing compound |
| CN107262092B (zh) * | 2017-06-16 | 2021-03-09 | 巨化集团技术中心 | 一种合成顺式1,1,1,4,4,4-六氟-2-丁烯的催化剂及其制备方法和用途 |
| CN107586251A (zh) * | 2017-07-26 | 2018-01-16 | 江苏蓝色星球环保科技股份有限公司 | 一种1,1,1,4,4,4‑六氟‑2‑丁烯的制备方法 |
| JP7656161B2 (ja) * | 2019-07-08 | 2025-04-03 | ダイキン工業株式会社 | フッ化ビニル化合物の製造方法 |
| CN110437028B (zh) * | 2019-07-30 | 2020-10-27 | 厦门大学 | 一种以铜为催化剂的氯代芳香化合物(R1-Xm)的脱氯方法 |
| CN110981688B (zh) * | 2019-10-31 | 2021-03-23 | 中国矿业大学(北京) | 一种气相催化合成3,4,4-三氟环丁烯的方法 |
| CN112876335B (zh) * | 2019-11-29 | 2022-05-10 | 浙江蓝天环保高科技股份有限公司 | 一种1,1,1,4,4,4-六氟-2-丁烯的制备方法 |
| JP7411780B2 (ja) | 2019-11-29 | 2024-01-11 | 浙江▲藍▼天▲環▼保高科技股▲ふん▼有限公司 | 窒素とリンで修飾された顆粒状炭素担持二元金属触媒、その作製方法およびその応用 |
| CN110975893B (zh) * | 2019-12-18 | 2023-04-18 | 浙江工业大学 | 用于二氟一氯甲烷高温裂解制四氟乙烯和六氟丙烯的金属氟化物催化剂、其制备方法和应用 |
| CN111574321B (zh) * | 2020-06-17 | 2021-09-03 | 广东电网有限责任公司电力科学研究院 | 一种反式-1,1,1,4,4,4-六氟-2-丁烯的制备方法 |
| WO2022085544A1 (ja) | 2020-10-22 | 2022-04-28 | Agc株式会社 | 電気設備 |
| CN112657508B (zh) * | 2020-12-04 | 2022-07-08 | 中化蓝天集团有限公司 | 一种核壳结构的加氢脱氯催化剂、其制备方法及应用 |
| CN116635970A (zh) | 2020-12-16 | 2023-08-22 | Agc株式会社 | 电气设备、填充设备和储存设备 |
| CN112745192A (zh) * | 2020-12-31 | 2021-05-04 | 山东华夏神舟新材料有限公司 | 顺式六氟-2-丁烯的连续制备方法 |
| CN114716297B (zh) * | 2021-01-06 | 2023-10-27 | 浙江省化工研究院有限公司 | 一种e-1,1,1,4,4,4-六氟-2-丁烯的制备方法 |
| CN112811975B (zh) * | 2021-04-22 | 2021-07-30 | 泉州宇极新材料科技有限公司 | 气相异构化制备z-1-r-3,3,3-三氟丙烯的方法 |
| CN114870858B (zh) * | 2022-03-04 | 2024-07-16 | 中化蓝天集团有限公司 | 一种抗积碳催化剂、其制备方法及应用 |
Family Cites Families (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2697124A (en) * | 1952-02-25 | 1954-12-14 | Kellogg M W Co | Dehalogenation of fluorohalocarbons |
| US2774799A (en) | 1954-04-01 | 1956-12-18 | Kellogg M W Co | Selective dehydrohalogenation of fluorohaloalkanes using a copper catalyst |
| US2802887A (en) | 1955-08-08 | 1957-08-13 | Allied Chem & Dye Corp | Hydrogenation of chlorotrifluoroethylene |
| US2900423A (en) | 1957-12-13 | 1959-08-18 | Allied Chem | Manufacture of perfluoropropene |
| ES289529A1 (es) | 1962-07-03 | 1963-11-01 | Allied Chem | Procedimiento de obtencion de alcohol hexafluoroisopropilico |
| JPS462324B1 (enExample) * | 1966-12-16 | 1971-01-21 | ||
| DE3170139D1 (en) * | 1980-12-09 | 1985-05-30 | Allied Corp | Preparation of chlorotrifluoroethylene and trifluoroethylene |
| IT1186307B (it) * | 1985-06-10 | 1987-11-26 | Montefluos Spa | Procedimento per la preparazione di 1,2-difluoroetilene e 1-cloro-1,2-difluoro-etilene |
| US5243103A (en) | 1988-05-24 | 1993-09-07 | Solvay S.A. | Process for obtaining catalytic compositions and process for hydrogenation of chlorofluoroalkenes by means of these compositions |
| RU2026279C1 (ru) * | 1989-02-03 | 1995-01-09 | Е.И.Дюпон Де Немур Энд Компани | Способ гидрогенолиза и/или дегидрогалогенирования фторгалоуглеродов и/или фторгалоуглеводородов |
| KR920701089A (ko) | 1989-02-03 | 1992-08-11 | 미리엄 디이 메코너헤이 | 개선된 가수소분해/탈할로겐화 수소반응 공정 |
| JP2526661B2 (ja) * | 1989-04-27 | 1996-08-21 | ダイキン工業株式会社 | フルオロアルキルビニル化合物の製造法 |
| US5068472A (en) | 1989-12-19 | 1991-11-26 | E. I. Du Pont De Nemours And Company | Multistep synthesis of hexafluoropropylene |
| US5097082A (en) * | 1990-06-05 | 1992-03-17 | E. I. Du Pont De Nemours And Company | Production of saturated halohydrocarbons |
| JP2763186B2 (ja) * | 1990-08-13 | 1998-06-11 | エフテック株式会社 | トリフルオロエチレンの製造方法 |
| FR2668769B1 (fr) * | 1990-11-06 | 1992-12-31 | Atochem | Fabrication de fluoroethylenes et de chlorofluoroethylenes. |
| JPH04286233A (ja) * | 1991-03-14 | 1992-10-12 | Nec Corp | スタッフ同期回路 |
| JP3275338B2 (ja) | 1992-01-13 | 2002-04-15 | ダイキン工業株式会社 | 1,1,1,4,4,4−ヘキサフルオロブタンの製造方法 |
| JPH05213793A (ja) | 1992-02-06 | 1993-08-24 | Daikin Ind Ltd | 1,1,1,4,4,4−ヘキサフルオロブタンの製造方法 |
| JPH05215793A (ja) | 1992-02-07 | 1993-08-24 | Fujitsu Ltd | 消費電流積算方式 |
| JP2806781B2 (ja) * | 1993-02-01 | 1998-09-30 | セントラル硝子株式会社 | フッ素化炭化水素の製造方法 |
| DE4305163A1 (de) | 1993-02-19 | 1994-08-25 | Bayer Ag | Verfahren zur Herstellung von Hexafluorbuten |
| RU2053841C1 (ru) * | 1993-05-26 | 1996-02-10 | Иркутский институт органической химии СО РАН | Катализатор селективного гидрирования третичных ацетиленовых спиртов |
| JP2003176243A (ja) * | 1993-06-10 | 2003-06-24 | Daikin Ind Ltd | 1,1,1,3,3−ペンタフルオロプロパン及び/又は1,1,3,3,3−ペンタフルオロプロペンの製造方法 |
| EP0714384A1 (en) | 1993-08-16 | 1996-06-05 | AlliedSignal Inc. | Process for combining chlorine-containing molecules to synthesize fluorine-containing products |
| US5892135A (en) | 1996-08-23 | 1999-04-06 | E. I. Du Pont De Nemours And Company | Process for the production of trifluoroethylene |
| DE19750789A1 (de) * | 1997-11-06 | 1999-05-20 | Beseitigung Von Umweltschaeden | Trägerkatalysator und Verfahren zur Herstellung von Fluorkohlenwasserstoffen |
| JP3876951B2 (ja) * | 1998-09-08 | 2007-02-07 | 日本ゼオン株式会社 | フルオロシクロペンテン類の製造方法 |
| US20050119512A1 (en) * | 2003-04-29 | 2005-06-02 | Central Glass Company, Limited | Fluorobutene derivatives and process for producing same |
| US7795482B2 (en) | 2007-07-03 | 2010-09-14 | E. I. Du Pont De Nemours And Company | Method of hydrodechlorination to produce dihydrofluorinated olefins |
-
2008
- 2008-06-27 US US12/147,644 patent/US7795482B2/en active Active
- 2008-06-30 CN CN2008800230985A patent/CN101687736B/zh active Active
- 2008-06-30 WO PCT/US2008/068695 patent/WO2009006358A1/en not_active Ceased
- 2008-06-30 CA CA002686603A patent/CA2686603A1/en not_active Abandoned
- 2008-06-30 ES ES08781141.0T patent/ES2443024T3/es active Active
- 2008-06-30 CN CN201310429220.1A patent/CN103524297B/zh active Active
- 2008-06-30 EP EP08781141.0A patent/EP2173693B1/en not_active Not-in-force
- 2008-06-30 KR KR1020107001164A patent/KR20100046147A/ko not_active Ceased
- 2008-06-30 RU RU2010103460/04A patent/RU2476414C2/ru not_active IP Right Cessation
- 2008-06-30 BR BRPI0810961A patent/BRPI0810961A2/pt not_active IP Right Cessation
- 2008-06-30 JP JP2010515208A patent/JP5660891B2/ja active Active
- 2008-07-02 TW TW097124919A patent/TW200922906A/zh unknown
-
2009
- 2009-06-03 US US12/477,366 patent/US7795481B2/en active Active
-
2012
- 2012-09-07 US US13/606,233 patent/USRE45076E1/en active Active
-
2014
- 2014-11-28 JP JP2014240840A patent/JP2015061861A/ja active Pending
-
2016
- 2016-11-28 JP JP2016229714A patent/JP2017075162A/ja active Pending
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