JP2012518010A - 新規なアルキルパーフルオロアルケンエーテルおよびその使用 - Google Patents
新規なアルキルパーフルオロアルケンエーテルおよびその使用 Download PDFInfo
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- JP2012518010A JP2012518010A JP2011550306A JP2011550306A JP2012518010A JP 2012518010 A JP2012518010 A JP 2012518010A JP 2011550306 A JP2011550306 A JP 2011550306A JP 2011550306 A JP2011550306 A JP 2011550306A JP 2012518010 A JP2012518010 A JP 2012518010A
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- 150000002170 ethers Chemical class 0.000 title description 19
- 125000000217 alkyl group Chemical group 0.000 title description 4
- 239000000203 mixture Substances 0.000 claims abstract description 182
- 238000000034 method Methods 0.000 claims abstract description 94
- 239000002904 solvent Substances 0.000 claims abstract description 78
- 150000001875 compounds Chemical class 0.000 claims abstract description 32
- 229920001774 Perfluoroether Polymers 0.000 claims abstract description 15
- 238000005238 degreasing Methods 0.000 claims abstract description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 69
- 239000000314 lubricant Substances 0.000 claims description 64
- 238000004140 cleaning Methods 0.000 claims description 60
- 229910052731 fluorine Inorganic materials 0.000 claims description 51
- 239000011737 fluorine Substances 0.000 claims description 51
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 50
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 50
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 46
- 239000004094 surface-active agent Substances 0.000 claims description 26
- 238000000576 coating method Methods 0.000 claims description 20
- 239000011248 coating agent Substances 0.000 claims description 17
- 229910052751 metal Inorganic materials 0.000 claims description 17
- 239000002184 metal Substances 0.000 claims description 17
- 230000008569 process Effects 0.000 claims description 17
- 238000000151 deposition Methods 0.000 claims description 16
- 239000003444 phase transfer catalyst Substances 0.000 claims description 16
- CDAVUOSPHHTNBU-UHFFFAOYSA-N 1,1,2,3,3,4,4,5,5,6,6,7,7,7-tetradecafluorohept-1-ene Chemical compound FC(F)=C(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F CDAVUOSPHHTNBU-UHFFFAOYSA-N 0.000 claims description 15
- 238000009835 boiling Methods 0.000 claims description 15
- 239000002585 base Substances 0.000 claims description 14
- 239000011521 glass Substances 0.000 claims description 12
- 239000000463 material Substances 0.000 claims description 11
- 239000010702 perfluoropolyether Substances 0.000 claims description 11
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims description 8
- XPDWGBQVDMORPB-UHFFFAOYSA-N Fluoroform Chemical compound FC(F)F XPDWGBQVDMORPB-UHFFFAOYSA-N 0.000 claims description 8
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 8
- 150000003983 crown ethers Chemical class 0.000 claims description 8
- RWRIWBAIICGTTQ-UHFFFAOYSA-N difluoromethane Chemical compound FCF RWRIWBAIICGTTQ-UHFFFAOYSA-N 0.000 claims description 8
- 238000007598 dipping method Methods 0.000 claims description 8
- 238000001704 evaporation Methods 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- 230000008020 evaporation Effects 0.000 claims description 7
- RGBFMLVTZCWFSL-UHFFFAOYSA-N 1,1,1,2,3,4,4,5,5,6,6,7,7,8,8,8-hexadecafluorooct-2-ene Chemical compound FC(F)(F)C(F)=C(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F RGBFMLVTZCWFSL-UHFFFAOYSA-N 0.000 claims description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
- 239000007864 aqueous solution Substances 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 239000003380 propellant Substances 0.000 claims description 6
- VVMQLAKDFBLCHB-UHFFFAOYSA-N 1,1,1,2,3,4,4,5,5,5-decafluoropent-2-ene Chemical group FC(F)(F)C(F)=C(F)C(F)(F)C(F)(F)F VVMQLAKDFBLCHB-UHFFFAOYSA-N 0.000 claims description 5
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 5
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 229920001515 polyalkylene glycol Polymers 0.000 claims description 5
- 239000004065 semiconductor Substances 0.000 claims description 5
- NPNPZTNLOVBDOC-UHFFFAOYSA-N 1,1-difluoroethane Chemical compound CC(F)F NPNPZTNLOVBDOC-UHFFFAOYSA-N 0.000 claims description 4
- 150000004703 alkoxides Chemical class 0.000 claims description 4
- 229930195733 hydrocarbon Natural products 0.000 claims description 4
- 150000002430 hydrocarbons Chemical class 0.000 claims description 4
- 238000007654 immersion Methods 0.000 claims description 4
- GTLACDSXYULKMZ-UHFFFAOYSA-N pentafluoroethane Chemical compound FC(F)C(F)(F)F GTLACDSXYULKMZ-UHFFFAOYSA-N 0.000 claims description 4
- LVGUZGTVOIAKKC-UHFFFAOYSA-N 1,1,1,2-tetrafluoroethane Chemical compound FCC(F)(F)F LVGUZGTVOIAKKC-UHFFFAOYSA-N 0.000 claims description 3
- UJPMYEOUBPIPHQ-UHFFFAOYSA-N 1,1,1-trifluoroethane Chemical compound CC(F)(F)F UJPMYEOUBPIPHQ-UHFFFAOYSA-N 0.000 claims description 3
- PBWHQPOHADDEFU-UHFFFAOYSA-N 1,1,2,3,3,4,4,5,5,5-decafluoropent-1-ene Chemical compound FC(F)=C(F)C(F)(F)C(F)(F)C(F)(F)F PBWHQPOHADDEFU-UHFFFAOYSA-N 0.000 claims description 3
- YCBPKOZNGFQMPB-UHFFFAOYSA-N 1,1,2,3,3,4,4,5,5,6,6,7,7,8,8,8-hexadecafluorooct-1-ene Chemical compound FC(F)=C(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F YCBPKOZNGFQMPB-UHFFFAOYSA-N 0.000 claims description 3
- FXRLMCRCYDHQFW-UHFFFAOYSA-N 2,3,3,3-tetrafluoropropene Chemical compound FC(=C)C(F)(F)F FXRLMCRCYDHQFW-UHFFFAOYSA-N 0.000 claims description 3
- 229910044991 metal oxide Inorganic materials 0.000 claims description 3
- 150000004706 metal oxides Chemical class 0.000 claims description 3
- 238000005507 spraying Methods 0.000 claims description 3
- CDOOAUSHHFGWSA-OWOJBTEDSA-N (e)-1,3,3,3-tetrafluoroprop-1-ene Chemical compound F\C=C\C(F)(F)F CDOOAUSHHFGWSA-OWOJBTEDSA-N 0.000 claims description 2
- DMUPYMORYHFFCT-UPHRSURJSA-N (z)-1,2,3,3,3-pentafluoroprop-1-ene Chemical compound F\C=C(/F)C(F)(F)F DMUPYMORYHFFCT-UPHRSURJSA-N 0.000 claims description 2
- RFYFRYQYXJPKMF-UHFFFAOYSA-N 1,1,1,2,2,3,4,5,5,6,6,6-dodecafluorohex-3-ene Chemical compound FC(F)(F)C(F)(F)C(F)=C(F)C(F)(F)C(F)(F)F RFYFRYQYXJPKMF-UHFFFAOYSA-N 0.000 claims description 2
- JBDBBTPNNYKSQX-UHFFFAOYSA-N 1,1,1,2,3,4,4,5,5,6,6,6-dodecafluorohex-2-ene Chemical compound FC(F)(F)C(F)=C(F)C(F)(F)C(F)(F)C(F)(F)F JBDBBTPNNYKSQX-UHFFFAOYSA-N 0.000 claims description 2
- UGHJWZHBCXGSAY-UHFFFAOYSA-N 1,1,1,2,3,4,4,5,5,6,6,7,7,7-tetradecafluorohept-2-ene Chemical compound FC(F)(F)C(F)=C(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F UGHJWZHBCXGSAY-UHFFFAOYSA-N 0.000 claims description 2
- CDOOAUSHHFGWSA-UHFFFAOYSA-N 1,3,3,3-tetrafluoropropene Chemical compound FC=CC(F)(F)F CDOOAUSHHFGWSA-UHFFFAOYSA-N 0.000 claims description 2
- 239000004215 Carbon black (E152) Substances 0.000 claims description 2
- 239000003570 air Substances 0.000 claims description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 2
- 239000001569 carbon dioxide Substances 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- 238000004528 spin coating Methods 0.000 claims description 2
- UJMWVICAENGCRF-UHFFFAOYSA-N oxygen difluoride Chemical class FOF UJMWVICAENGCRF-UHFFFAOYSA-N 0.000 claims 3
- RMHCWMIZBMGHKV-UHFFFAOYSA-N 1,1,2,3,3,4,4,5,5,6,6,6-dodecafluorohex-1-ene Chemical compound FC(F)=C(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F RMHCWMIZBMGHKV-UHFFFAOYSA-N 0.000 claims 2
- DJGAMLSXFFGRHU-UHFFFAOYSA-N 1,1,1,2,2,3,3,4,5,6,6,7,7,8,8,8-hexadecafluorooct-4-ene Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)=C(F)C(F)(F)C(F)(F)C(F)(F)F DJGAMLSXFFGRHU-UHFFFAOYSA-N 0.000 claims 1
- SWAGURZABQHSTO-UHFFFAOYSA-N 1,1,1,2,2,3,4,5,5,6,6,7,7,8,8,8-hexadecafluorooct-3-ene Chemical compound FC(F)(F)C(F)(F)C(F)=C(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F SWAGURZABQHSTO-UHFFFAOYSA-N 0.000 claims 1
- WZHKDGJSXCTSCK-UHFFFAOYSA-N hept-3-ene Chemical compound CCCC=CCC WZHKDGJSXCTSCK-UHFFFAOYSA-N 0.000 claims 1
- 239000012530 fluid Substances 0.000 abstract description 7
- 239000012024 dehydrating agents Substances 0.000 abstract 1
- 239000000758 substrate Substances 0.000 description 50
- 239000003921 oil Substances 0.000 description 33
- 238000006243 chemical reaction Methods 0.000 description 31
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 31
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 27
- -1 unsaturated fluorocarbon ethers Chemical class 0.000 description 27
- 238000007792 addition Methods 0.000 description 19
- 238000001035 drying Methods 0.000 description 19
- 239000010410 layer Substances 0.000 description 19
- UAEWLONMSWUOCA-UHFFFAOYSA-N 1,1,1,2,2,3,4,5,5,6,6,7,7,7-tetradecafluorohept-3-ene Chemical compound FC(F)(F)C(F)(F)C(F)=C(F)C(F)(F)C(F)(F)C(F)(F)F UAEWLONMSWUOCA-UHFFFAOYSA-N 0.000 description 18
- 239000000356 contaminant Substances 0.000 description 18
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 15
- 239000000243 solution Substances 0.000 description 15
- 230000018044 dehydration Effects 0.000 description 14
- 238000006297 dehydration reaction Methods 0.000 description 14
- 239000000047 product Substances 0.000 description 12
- 239000000654 additive Substances 0.000 description 11
- 230000008901 benefit Effects 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 9
- 229910000000 metal hydroxide Inorganic materials 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 238000004821 distillation Methods 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- 230000000996 additive effect Effects 0.000 description 7
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 7
- 235000019341 magnesium sulphate Nutrition 0.000 description 7
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 7
- 238000003618 dip coating Methods 0.000 description 6
- 230000004907 flux Effects 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
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- 150000002924 oxiranes Chemical class 0.000 description 5
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- 229910019142 PO4 Inorganic materials 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 4
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- XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical group [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 description 4
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- 125000003710 aryl alkyl group Chemical group 0.000 description 3
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- ZUHZGEOKBKGPSW-UHFFFAOYSA-N tetraglyme Chemical compound COCCOCCOCCOCCOC ZUHZGEOKBKGPSW-UHFFFAOYSA-N 0.000 description 2
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- WXGNWUVNYMJENI-UHFFFAOYSA-N 1,1,2,2-tetrafluoroethane Chemical compound FC(F)C(F)F WXGNWUVNYMJENI-UHFFFAOYSA-N 0.000 description 1
- NDMMKOCNFSTXRU-UHFFFAOYSA-N 1,1,2,3,3-pentafluoroprop-1-ene Chemical compound FC(F)C(F)=C(F)F NDMMKOCNFSTXRU-UHFFFAOYSA-N 0.000 description 1
- AJDIZQLSFPQPEY-UHFFFAOYSA-N 1,1,2-Trichlorotrifluoroethane Chemical compound FC(F)(Cl)C(F)(Cl)Cl AJDIZQLSFPQPEY-UHFFFAOYSA-N 0.000 description 1
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- BRKFQVAOMSWFDU-UHFFFAOYSA-M tetraphenylphosphanium;bromide Chemical compound [Br-].C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 BRKFQVAOMSWFDU-UHFFFAOYSA-M 0.000 description 1
- WAGFXJQAIZNSEQ-UHFFFAOYSA-M tetraphenylphosphonium chloride Chemical compound [Cl-].C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 WAGFXJQAIZNSEQ-UHFFFAOYSA-M 0.000 description 1
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Classifications
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- 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
- C07C43/14—Unsaturated ethers
- C07C43/17—Unsaturated ethers containing halogen
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/045—Hydroxy compounds, e.g. alcohols; Salts thereof, e.g. alcoholates
- A61K31/05—Phenols
-
- 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
- C07C43/14—Unsaturated ethers
- C07C43/164—Unsaturated ethers containing six-membered aromatic rings
- C07C43/166—Unsaturated ethers containing six-membered aromatic rings having unsaturation outside the aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
- C11D7/50—Solvents
- C11D7/5004—Organic solvents
- C11D7/5018—Halogenated solvents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Detergent Compositions (AREA)
- Cleaning And De-Greasing Of Metallic Materials By Chemical Methods (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Lubricants (AREA)
Applications Claiming Priority (5)
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| US15280309P | 2009-02-16 | 2009-02-16 | |
| US61/152,803 | 2009-02-16 | ||
| US28727509P | 2009-12-17 | 2009-12-17 | |
| US61/287,275 | 2009-12-17 | ||
| PCT/US2010/024259 WO2010094019A2 (en) | 2009-02-16 | 2010-02-16 | Novel alkyl perfluoroalkene ethers and uses thereof |
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| JP2015035749A Division JP5881875B2 (ja) | 2009-02-16 | 2015-02-25 | 新規なアルキルパーフルオロアルケンエーテルおよびその使用 |
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| JP2015035749A Active JP5881875B2 (ja) | 2009-02-16 | 2015-02-25 | 新規なアルキルパーフルオロアルケンエーテルおよびその使用 |
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| JP2015035749A Active JP5881875B2 (ja) | 2009-02-16 | 2015-02-25 | 新規なアルキルパーフルオロアルケンエーテルおよびその使用 |
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| US (2) | US8399713B2 (enExample) |
| EP (1) | EP2396294B1 (enExample) |
| JP (2) | JP2012518010A (enExample) |
| KR (1) | KR101856233B1 (enExample) |
| CN (1) | CN102317245B (enExample) |
| ES (1) | ES2547327T3 (enExample) |
| MY (1) | MY157701A (enExample) |
| SG (1) | SG173696A1 (enExample) |
| TW (1) | TWI418534B (enExample) |
| WO (1) | WO2010094019A2 (enExample) |
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| JP2014530206A (ja) * | 2011-09-26 | 2014-11-17 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニーＥ．Ｉ．Ｄｕ Ｐｏｎｔ Ｄｅ Ｎｅｍｏｕｒｓ Ａｎｄ Ｃｏｍｐａｎｙ | アルキルパーフルオロアルケンエーテル製造において成分を分離する方法 |
| WO2018237297A1 (en) | 2017-06-23 | 2018-12-27 | Dupont-Mitsui Fluorochemicals Co. Ltd | Melt processible fluororesin molded article |
| WO2019111989A1 (ja) * | 2017-12-07 | 2019-06-13 | 関東電化工業株式会社 | 塩素化ビス（３，３，３－トリフルオロ－１－プロペニル）エーテル、その製造方法及びその用途 |
| JPWO2019093350A1 (ja) * | 2017-11-07 | 2020-12-24 | 神戸合成株式会社 | 洗浄剤組成物及びそのエアゾール組成物 |
| JP2022504909A (ja) * | 2018-10-15 | 2022-01-13 | 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 | フッ素化アルコキシビニルエーテル及びフッ素化アルコキシビニルエーテルの調製方法 |
| WO2022031585A1 (en) | 2020-08-03 | 2022-02-10 | The Chemours Company Fc, Llc | Resin pellet, method of its manufacturing, and molded product thereof |
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| JP2023554327A (ja) * | 2020-12-11 | 2023-12-27 | メキシケム フロー エセ・ア・デ・セ・ヴェ | 組成物 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2014530206A (ja) * | 2011-09-26 | 2014-11-17 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニーＥ．Ｉ．Ｄｕ Ｐｏｎｔ Ｄｅ Ｎｅｍｏｕｒｓ Ａｎｄ Ｃｏｍｐａｎｙ | アルキルパーフルオロアルケンエーテル製造において成分を分離する方法 |
| WO2018237297A1 (en) | 2017-06-23 | 2018-12-27 | Dupont-Mitsui Fluorochemicals Co. Ltd | Melt processible fluororesin molded article |
| US11964417B2 (en) | 2017-06-23 | 2024-04-23 | Chemours-Mitsui Fluoroproducts Co., Ltd. | Melt processible fluororesin molded article |
| JP2023107823A (ja) * | 2017-11-07 | 2023-08-03 | 神戸合成株式会社 | 洗浄剤組成物及びそのエアゾール組成物 |
| JPWO2019093350A1 (ja) * | 2017-11-07 | 2020-12-24 | 神戸合成株式会社 | 洗浄剤組成物及びそのエアゾール組成物 |
| JP7493850B2 (ja) | 2017-11-07 | 2024-06-03 | 神戸合成株式会社 | 洗浄剤組成物及びそのエアゾール組成物 |
| JP2022075769A (ja) * | 2017-11-07 | 2022-05-18 | 神戸合成株式会社 | 洗浄剤組成物及びそのエアゾール組成物 |
| JP7098170B2 (ja) | 2017-11-07 | 2022-07-11 | 神戸合成株式会社 | 洗浄剤組成物及びそのエアゾール組成物 |
| WO2019111989A1 (ja) * | 2017-12-07 | 2019-06-13 | 関東電化工業株式会社 | 塩素化ビス（３，３，３－トリフルオロ－１－プロペニル）エーテル、その製造方法及びその用途 |
| JP2022504909A (ja) * | 2018-10-15 | 2022-01-13 | 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 | フッ素化アルコキシビニルエーテル及びフッ素化アルコキシビニルエーテルの調製方法 |
| JP7525481B2 (ja) | 2018-10-15 | 2024-07-30 | 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 | フッ素化アルコキシビニルエーテル及びフッ素化アルコキシビニルエーテルの調製方法 |
| JP2022515433A (ja) * | 2018-12-26 | 2022-02-18 | スリーエム イノベイティブ プロパティズ カンパニー | ハイドロクロロフルオロオレフィン及びその使用方法 |
| JP2023526606A (ja) * | 2020-05-19 | 2023-06-22 | 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 | 安定化された伝熱流体組成物 |
| KR20230048076A (ko) | 2020-08-03 | 2023-04-10 | 미쯔이 케무어스 플루오로프로덕츠 가부시끼가이샤 | 수지 펠릿, 이의 제조 방법, 및 이의 성형품 |
| WO2022031585A1 (en) | 2020-08-03 | 2022-02-10 | The Chemours Company Fc, Llc | Resin pellet, method of its manufacturing, and molded product thereof |
| JP2023554327A (ja) * | 2020-12-11 | 2023-12-27 | メキシケム フロー エセ・ア・デ・セ・ヴェ | 組成物 |
Also Published As
| Publication number | Publication date |
|---|---|
| MY157701A (en) | 2016-07-15 |
| US8399713B2 (en) | 2013-03-19 |
| WO2010094019A3 (en) | 2011-02-17 |
| TW201100367A (en) | 2011-01-01 |
| US20100209600A1 (en) | 2010-08-19 |
| SG173696A1 (en) | 2011-09-29 |
| HK1165786A1 (en) | 2012-10-12 |
| CN102317245A (zh) | 2012-01-11 |
| KR101856233B1 (ko) | 2018-06-25 |
| ES2547327T3 (es) | 2015-10-05 |
| CN102317245B (zh) | 2015-06-17 |
| JP5881875B2 (ja) | 2016-03-09 |
| EP2396294B1 (en) | 2015-07-22 |
| US20110282104A1 (en) | 2011-11-17 |
| KR20110121635A (ko) | 2011-11-07 |
| WO2010094019A2 (en) | 2010-08-19 |
| EP2396294A2 (en) | 2011-12-21 |
| TWI418534B (zh) | 2013-12-11 |
| JP2015110802A (ja) | 2015-06-18 |
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