JP5313674B2 - ハイドロフルオロエーテル化合物類およびそれらの調製方法および用途 - Google Patents
ハイドロフルオロエーテル化合物類およびそれらの調製方法および用途 Download PDFInfo
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- JP5313674B2 JP5313674B2 JP2008530071A JP2008530071A JP5313674B2 JP 5313674 B2 JP5313674 B2 JP 5313674B2 JP 2008530071 A JP2008530071 A JP 2008530071A JP 2008530071 A JP2008530071 A JP 2008530071A JP 5313674 B2 JP5313674 B2 JP 5313674B2
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- Prior art keywords
- ocf
- cfhcf
- hydrofluoroether
- perfluorinated
- mol
- Prior art date
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- 125000005842 heteroatom Chemical group 0.000 claims abstract description 22
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- 239000000203 mixture Substances 0.000 claims description 71
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 64
- 238000006243 chemical reaction Methods 0.000 claims description 32
- 150000001336 alkenes Chemical class 0.000 claims description 30
- 125000000217 alkyl group Chemical group 0.000 claims description 28
- 150000003254 radicals Chemical class 0.000 claims description 24
- 238000007259 addition reaction Methods 0.000 claims description 22
- 239000002904 solvent Substances 0.000 claims description 22
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 21
- 239000007858 starting material Substances 0.000 claims description 19
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- 125000004122 cyclic group Chemical group 0.000 claims description 13
- AQYSYJUIMQTRMV-UHFFFAOYSA-N hypofluorous acid Chemical compound FO AQYSYJUIMQTRMV-UHFFFAOYSA-N 0.000 claims description 13
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- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 8
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- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
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- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 6
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 6
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- 238000004821 distillation Methods 0.000 description 6
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- 150000001721 carbon Chemical group 0.000 description 5
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- ASZZHBXPMOVHCU-UHFFFAOYSA-N 3,9-diazaspiro[5.5]undecane-2,4-dione Chemical compound C1C(=O)NC(=O)CC11CCNCC1 ASZZHBXPMOVHCU-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 150000002222 fluorine compounds Chemical class 0.000 description 4
- HCDGVLDPFQMKDK-UHFFFAOYSA-N hexafluoropropylene Chemical group FC(F)=C(F)C(F)(F)F HCDGVLDPFQMKDK-UHFFFAOYSA-N 0.000 description 4
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 4
- 239000012264 purified product Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 4
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- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000003963 antioxidant agent Substances 0.000 description 3
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- XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 description 3
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- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 2
- RJBJXVAPYONTFE-UHFFFAOYSA-N 1,1,1,2,3,3-hexafluoro-2-(1,1,2,2,3,3,3-heptafluoropropoxy)-3-(1,2,2-trifluoroethenoxy)propane Chemical compound FC(F)=C(F)OC(F)(F)C(F)(C(F)(F)F)OC(F)(F)C(F)(F)C(F)(F)F RJBJXVAPYONTFE-UHFFFAOYSA-N 0.000 description 2
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- IFXDUNDBQDXPQZ-UHFFFAOYSA-N 2-methylbutan-2-yl 2-ethylhexaneperoxoate Chemical compound CCCCC(CC)C(=O)OOC(C)(C)CC IFXDUNDBQDXPQZ-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
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- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
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- 229910052809 inorganic oxide Inorganic materials 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 150000007527 lewis bases Chemical class 0.000 description 1
- 238000003754 machining Methods 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000006078 metal deactivator Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- QLOAVXSYZAJECW-UHFFFAOYSA-N methane;molecular fluorine Chemical compound C.FF QLOAVXSYZAJECW-UHFFFAOYSA-N 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000006082 mold release agent Substances 0.000 description 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000013618 particulate matter Substances 0.000 description 1
- QMMOXUPEWRXHJS-UHFFFAOYSA-N pent-2-ene Chemical class CCC=CC QMMOXUPEWRXHJS-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 150000004978 peroxycarbonates Chemical class 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 229920002120 photoresistant polymer Polymers 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000002984 plastic foam Substances 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- GKKCIDNWFBPDBW-UHFFFAOYSA-M potassium cyanate Chemical compound [K]OC#N GKKCIDNWFBPDBW-UHFFFAOYSA-M 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- VBKNTGMWIPUCRF-UHFFFAOYSA-M potassium;fluoride;hydrofluoride Chemical compound F.[F-].[K+] VBKNTGMWIPUCRF-UHFFFAOYSA-M 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000003672 processing method Methods 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000005057 refrigeration Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
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- 239000004416 thermosoftening plastic Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
- C07C43/04—Saturated ethers
- C07C43/12—Saturated ethers containing halogen
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
- C07C43/04—Saturated ethers
- C07C43/12—Saturated ethers containing halogen
- C07C43/126—Saturated ethers containing halogen having more than one ether bond
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T83/00—Cutting
- Y10T83/04—Processes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Physics & Mathematics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Combustion & Propulsion (AREA)
- Thermal Sciences (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Lubricants (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11/222,383 US7691282B2 (en) | 2005-09-08 | 2005-09-08 | Hydrofluoroether compounds and processes for their preparation and use |
| US11/222,383 | 2005-09-08 | ||
| PCT/US2006/032704 WO2007030314A2 (en) | 2005-09-08 | 2006-08-23 | Hydrofluoroether compounds and processes for their preparation and use |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2009507840A JP2009507840A (ja) | 2009-02-26 |
| JP2009507840A5 JP2009507840A5 (enExample) | 2009-09-24 |
| JP5313674B2 true JP5313674B2 (ja) | 2013-10-09 |
Family
ID=37719842
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2008530071A Expired - Fee Related JP5313674B2 (ja) | 2005-09-08 | 2006-08-23 | ハイドロフルオロエーテル化合物類およびそれらの調製方法および用途 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US7691282B2 (enExample) |
| EP (1) | EP1931614B1 (enExample) |
| JP (1) | JP5313674B2 (enExample) |
| KR (1) | KR101298324B1 (enExample) |
| CN (1) | CN101263103A (enExample) |
| WO (1) | WO2007030314A2 (enExample) |
Families Citing this family (42)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8791254B2 (en) * | 2006-05-19 | 2014-07-29 | 3M Innovative Properties Company | Cyclic hydrofluoroether compounds and processes for their preparation and use |
| WO2008024602A1 (en) * | 2006-08-24 | 2008-02-28 | 3M Innovative Properties Company | Process for producing fluoropolymers |
| US8193397B2 (en) * | 2006-12-06 | 2012-06-05 | 3M Innovative Properties Company | Hydrofluoroether compounds and processes for their preparation and use |
| US8142702B2 (en) * | 2007-06-18 | 2012-03-27 | Molecular Imprints, Inc. | Solvent-assisted layer formation for imprint lithography |
| EP2025731A1 (en) * | 2007-08-06 | 2009-02-18 | Solvay Solexis S.p.A. | Heat Transfer fluid |
| JP5265688B2 (ja) * | 2007-10-12 | 2013-08-14 | スリーエム イノベイティブ プロパティズ カンパニー | 清浄なフルオロポリマーを製造するプロセス |
| US8003004B2 (en) * | 2008-01-23 | 2011-08-23 | 3M Innovative Properties Company | Heat transfer apparatus and methods including hydrofluorocarbonates |
| US8071816B2 (en) | 2008-06-30 | 2011-12-06 | 3M Innovative Properties Company | Hydrofluoroacetal compounds and processes for their preparation and use |
| US20100028784A1 (en) * | 2008-07-29 | 2010-02-04 | 3M Innovative Properties Company | Electrolyte composition, lithium-containing electrochemical cell, battery pack, and device including the same |
| KR101606609B1 (ko) * | 2008-09-26 | 2016-03-25 | 솔베이 스페셜티 폴리머스 이태리 에스.피.에이. | 열을 전달하는 방법 |
| US7988877B2 (en) | 2008-11-03 | 2011-08-02 | 3M Innovative Properties Company | Methods of making fluorinated ethers, fluorinated ethers, and uses thereof |
| GB0823120D0 (en) | 2008-12-19 | 2009-01-28 | 3M Innovative Properties Co | Method of making fluorinated alkoxy carboxylic acids and precursors thereof |
| US8399713B2 (en) * | 2009-02-16 | 2013-03-19 | E I Du Pont De Nemours And Company | Alkyl perfluoroalkene ethers |
| US20100263885A1 (en) * | 2009-04-21 | 2010-10-21 | 3M Innovative Properties Company | Protection systems and methods for electronic devices |
| WO2010130628A1 (en) | 2009-05-15 | 2010-11-18 | Solvay Solexis S.P.A. | Process for the purification of polyol pfpe derivatives |
| US8323524B2 (en) * | 2009-10-01 | 2012-12-04 | 3M Innovative Properties Company | Apparatus including hydrofluoroether with high temperature stability and uses thereof |
| US8261560B2 (en) * | 2009-11-02 | 2012-09-11 | 3M Innovative Properties Company | Methods of using hydrofluoroethers as heat transfer fluids |
| US8486295B2 (en) * | 2010-07-09 | 2013-07-16 | E I Du Pont De Nemours And Company | Alkyl perfluoroalkene ethers and uses thereof |
| CN103210054B (zh) * | 2010-09-10 | 2016-06-15 | 索尔维特殊聚合物意大利有限公司 | 传热方法 |
| EP2655306B1 (en) * | 2010-12-21 | 2018-06-27 | Solvay Specialty Polymers Italy S.p.A. | Process for producing fluorinated organic compounds |
| JP5620456B2 (ja) * | 2012-11-20 | 2014-11-05 | 住友ゴム工業株式会社 | 表面改質方法及び表面改質弾性体 |
| WO2014163004A1 (ja) * | 2013-04-04 | 2014-10-09 | 旭硝子株式会社 | 含フッ素エーテル化合物、含フッ素エーテル組成物およびコーティング液、ならびに表面層を有する基材およびその製造方法 |
| CN106103408A (zh) * | 2014-02-21 | 2016-11-09 | 默克专利股份有限公司 | 氟表面活性剂 |
| EP3107893B1 (de) | 2014-02-21 | 2020-03-25 | Merck Patent GmbH | Fluortenside |
| US10308592B2 (en) | 2014-09-23 | 2019-06-04 | 3M Innovative Properties Company | Nitrogen containing hydrofluoroethers and methods of using same |
| US10099982B2 (en) * | 2014-12-22 | 2018-10-16 | 3M Innovative Properties Company | Methods of making halogenated partially fluorinated compounds |
| WO2016152425A1 (ja) * | 2015-03-25 | 2016-09-29 | 日本電気株式会社 | ハイドロフルオロエーテル化合物、非水電解液およびリチウムイオン二次電池 |
| EP3303436B1 (en) * | 2015-06-05 | 2020-12-09 | 3M Innovative Properties Company | Hydrofluoroolefins and methods of using same |
| US10723683B2 (en) | 2015-12-24 | 2020-07-28 | 3M Innovative Properties Company | Conversion of a perfluorinated vinyl ether into a partially fluorinated saturated ether derivative |
| CN108713014A (zh) * | 2016-03-11 | 2018-10-26 | 3M创新有限公司 | 含胺的无环氢氟醚及其使用方法 |
| EP3515886A4 (en) * | 2016-09-26 | 2020-05-06 | 3M Innovative Properties Company | HYDROFLUOROLEFINS CONTAINING NITROGEN AND / OR OXYGEN AND METHOD FOR THE PRODUCTION AND USE THEREOF |
| US11673861B2 (en) * | 2017-12-13 | 2023-06-13 | 3M Innovative Properties Company | Perfluorinated 1-alkoxypropenes, compositions, and methods and apparatuses for using same |
| CN108570369B (zh) * | 2018-04-09 | 2020-12-29 | 三明市海斯福化工有限责任公司 | 包含氧杂氢氟醚化合物的清洗组合物及其用于清洁的方法 |
| CN109529247A (zh) * | 2018-09-29 | 2019-03-29 | 广州华葳生物科技有限公司 | 一种用于降解回收废纸中的甲醛的生物环保制剂及其制备方法 |
| GB201916217D0 (en) * | 2019-10-03 | 2019-12-25 | Mexichem Fluor Sa De Cv | Composition |
| JP7720851B2 (ja) | 2020-01-29 | 2025-08-08 | スリーエム イノベイティブ プロパティズ カンパニー | 堆積組成物、並びにそれを製造及び使用する方法 |
| WO2022138768A1 (ja) * | 2020-12-24 | 2022-06-30 | ダイキン工業株式会社 | フルオロポリマーの製造方法 |
| CN113717698B (zh) * | 2021-07-15 | 2023-06-06 | 浙江巨化技术中心有限公司 | 一种组合物、含氟烯烃齐聚物液冷剂及其制备方法以及浸没冷却系统 |
| CN116262687B (zh) * | 2021-12-14 | 2024-05-14 | 中昊晨光化工研究院有限公司 | 一种氢氟醚的制备方法 |
| EP4600239A1 (en) | 2022-10-04 | 2025-08-13 | Daikin Industries, Ltd. | Fluorine-containing ether compound and method for producing same |
| CN116478020B (zh) * | 2023-04-20 | 2025-03-28 | 深圳市嘉顺亿实业有限公司 | 一种高纯氢氟醚化合物及其制备方法 |
| WO2025164448A1 (ja) * | 2024-01-31 | 2025-08-07 | Ａｇｃ株式会社 | ハイドロフルオロエーテルオレフィンの濃度低減方法 |
Family Cites Families (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3351495A (en) * | 1966-11-22 | 1967-11-07 | Grace W R & Co | Battery separator |
| NL7401510A (enExample) * | 1973-02-09 | 1974-08-13 | ||
| US4539256A (en) * | 1982-09-09 | 1985-09-03 | Minnesota Mining And Manufacturing Co. | Microporous sheet material, method of making and articles made therewith |
| GB8301506D0 (en) | 1983-01-20 | 1983-02-23 | Electricity Council | Fluorinated ethers |
| US4650730A (en) * | 1985-05-16 | 1987-03-17 | W. R. Grace & Co. | Battery separator |
| GB9023370D0 (en) * | 1990-10-26 | 1990-12-05 | Rhone Poulenc Chemicals | Synthesis of fluorinated substituted ethanes |
| US5539008A (en) * | 1993-12-29 | 1996-07-23 | Minnesota Mining And Manufacturing Company | Foamable composition containing unsaturated perfluorochemical blowing agent |
| JP3304187B2 (ja) | 1994-03-14 | 2002-07-22 | 日本電信電話株式会社 | リチウム２次電池用電解液 |
| US5565281A (en) * | 1994-12-02 | 1996-10-15 | Hoechst Celanese Corporation | Shutdown, bilayer battery separator |
| DE19619233A1 (de) | 1996-05-13 | 1997-11-20 | Hoechst Ag | Fluorhaltige Lösungsmittel für Lithiumbatterien mit erhöhter Sicherheit |
| US6203944B1 (en) * | 1998-03-26 | 2001-03-20 | 3M Innovative Properties Company | Electrode for a lithium battery |
| US6080448A (en) * | 1998-04-03 | 2000-06-27 | Preservation Technologies Lp | Deacidification of cellulose based materials using hydrofluoroether carriers |
| US6255017B1 (en) | 1998-07-10 | 2001-07-03 | 3M Innovative Properties Co. | Electrode material and compositions including same |
| CN1147959C (zh) | 1998-09-11 | 2004-04-28 | 三井化学株式会社 | 非水电解液和非水电解液二次电池 |
| CN1206249C (zh) * | 1998-11-30 | 2005-06-15 | 纳幕尔杜邦公司 | 氟单体的聚合反应 |
| US6374907B1 (en) | 1999-10-08 | 2002-04-23 | 3M Innovative Properties Company | Hydrofluoroether as a heat-transfer fluid |
| US6699336B2 (en) * | 2000-01-13 | 2004-03-02 | 3M Innovative Properties Company | Amorphous electrode compositions |
| US20030211390A1 (en) * | 2000-12-22 | 2003-11-13 | Dahn Jeffrey R. | Grain boundary materials as electrodes for lithium ion cells |
| JP3482488B2 (ja) | 2000-12-28 | 2003-12-22 | 独立行政法人産業技術総合研究所 | 含フッ素エーテル化合物の製造方法 |
| US6534220B2 (en) * | 2000-12-29 | 2003-03-18 | 3M Innovative Properties Company | High-boiling electrolyte solvent |
| JP2004534264A (ja) | 2001-06-18 | 2004-11-11 | ハネウェル・インターナショナル・インコーポレーテッド | フッ素含有化合物及びそれらから誘導されたポリマー |
| US6680145B2 (en) * | 2001-08-07 | 2004-01-20 | 3M Innovative Properties Company | Lithium-ion batteries |
| US6759374B2 (en) * | 2001-09-19 | 2004-07-06 | 3M Innovative Properties Company | Composition comprising lubricious additive for cutting or abrasive working and a method therefor |
| US7229718B2 (en) * | 2002-08-22 | 2007-06-12 | Samsung Sdi Co., Ltd. | Electrolyte for rechargeable lithium battery and rechargeable lithium battery comprising same |
| US20040117918A1 (en) * | 2002-12-11 | 2004-06-24 | The Procter & Gamble Company | Fluorine-containing solvents and compositions and methods employing same |
| JP2004345967A (ja) * | 2003-05-20 | 2004-12-09 | Daikin Ind Ltd | 含フッ素エーテル化合物の製造方法 |
| JP4431941B2 (ja) | 2003-06-06 | 2010-03-17 | 株式会社ジーエス・ユアサコーポレーション | 非水電解質二次電池 |
| US7498100B2 (en) * | 2003-08-08 | 2009-03-03 | 3M Innovative Properties Company | Multi-phase, silicon-containing electrode for a lithium-ion battery |
| US7128133B2 (en) * | 2003-12-16 | 2006-10-31 | 3M Innovative Properties Company | Hydrofluoroether as a heat-transfer fluid |
| JP4660104B2 (ja) | 2004-03-23 | 2011-03-30 | スリーエム イノベイティブ プロパティズ カンパニー | 非水性混合溶媒及びそれを含む非水性電解液 |
| US20060046144A1 (en) * | 2004-09-01 | 2006-03-02 | 3M Innovative Properties Company | Anode composition for lithium ion battery |
| JP2006216361A (ja) | 2005-02-03 | 2006-08-17 | Three M Innovative Properties Co | リチウム電池用電解液 |
| US7790312B2 (en) * | 2005-09-08 | 2010-09-07 | 3M Innovative Properties Company | Electrolyte composition |
-
2005
- 2005-09-08 US US11/222,383 patent/US7691282B2/en not_active Expired - Fee Related
-
2006
- 2006-08-23 JP JP2008530071A patent/JP5313674B2/ja not_active Expired - Fee Related
- 2006-08-23 KR KR1020087005606A patent/KR101298324B1/ko not_active Expired - Fee Related
- 2006-08-23 WO PCT/US2006/032704 patent/WO2007030314A2/en not_active Ceased
- 2006-08-23 EP EP20060789911 patent/EP1931614B1/en not_active Not-in-force
- 2006-08-23 CN CNA2006800331224A patent/CN101263103A/zh active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| WO2007030314A3 (en) | 2007-05-03 |
| US20070051916A1 (en) | 2007-03-08 |
| EP1931614B1 (en) | 2012-07-04 |
| KR20080044271A (ko) | 2008-05-20 |
| WO2007030314A2 (en) | 2007-03-15 |
| CN101263103A (zh) | 2008-09-10 |
| EP1931614A2 (en) | 2008-06-18 |
| US7691282B2 (en) | 2010-04-06 |
| KR101298324B1 (ko) | 2013-08-20 |
| JP2009507840A (ja) | 2009-02-26 |
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