JP5280857B2 - フルオロケミカルケトン化合物及びそれらの使用方法 - Google Patents
フルオロケミカルケトン化合物及びそれらの使用方法 Download PDFInfo
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- JP5280857B2 JP5280857B2 JP2008547500A JP2008547500A JP5280857B2 JP 5280857 B2 JP5280857 B2 JP 5280857B2 JP 2008547500 A JP2008547500 A JP 2008547500A JP 2008547500 A JP2008547500 A JP 2008547500A JP 5280857 B2 JP5280857 B2 JP 5280857B2
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- Prior art keywords
- compound
- ocf
- fluorochemical
- perfluoropolyether
- group
- 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.)
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- -1 ketone compounds Chemical class 0.000 title claims description 75
- 238000000034 method Methods 0.000 title claims description 37
- 239000000203 mixture Substances 0.000 claims description 73
- 239000010702 perfluoropolyether Substances 0.000 claims description 43
- 150000001875 compounds Chemical class 0.000 claims description 41
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims description 19
- 239000002904 solvent Substances 0.000 claims description 18
- 239000012530 fluid Substances 0.000 claims description 13
- 239000007788 liquid Substances 0.000 claims description 13
- 239000000463 material Substances 0.000 claims description 12
- 229910052751 metal Inorganic materials 0.000 claims description 12
- 239000002184 metal Substances 0.000 claims description 12
- 125000005701 difluoromethyleneoxy group Chemical group FC(F)([*:1])O[*:2] 0.000 claims description 10
- 239000011248 coating agent Substances 0.000 claims description 9
- 238000000576 coating method Methods 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 8
- 239000011551 heat transfer agent Substances 0.000 claims description 8
- 125000005842 heteroatom Chemical group 0.000 claims description 8
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 8
- 229920000642 polymer Polymers 0.000 claims description 8
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 7
- 239000000758 substrate Substances 0.000 claims description 7
- 239000004088 foaming agent Substances 0.000 claims description 6
- 238000006116 polymerization reaction Methods 0.000 claims description 6
- 238000012546 transfer Methods 0.000 claims description 6
- 239000000654 additive Substances 0.000 claims description 5
- 150000004703 alkoxides Chemical class 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 239000011195 cermet Substances 0.000 claims description 5
- 239000002131 composite material Substances 0.000 claims description 5
- 239000000356 contaminant Substances 0.000 claims description 5
- 238000000151 deposition Methods 0.000 claims description 5
- 239000000178 monomer Substances 0.000 claims description 5
- 229910000679 solder Inorganic materials 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 239000002168 alkylating agent Substances 0.000 claims description 4
- 229940100198 alkylating agent Drugs 0.000 claims description 4
- 238000005476 soldering Methods 0.000 claims description 4
- 239000012808 vapor phase Substances 0.000 claims description 4
- 230000000996 additive effect Effects 0.000 claims description 3
- 238000005520 cutting process Methods 0.000 claims description 3
- 230000001050 lubricating effect Effects 0.000 claims description 3
- 239000003505 polymerization initiator Substances 0.000 claims description 3
- 230000000379 polymerizing effect Effects 0.000 claims description 3
- 239000002243 precursor Substances 0.000 claims description 3
- 230000008016 vaporization Effects 0.000 claims description 3
- 230000008018 melting Effects 0.000 claims description 2
- 238000002844 melting Methods 0.000 claims description 2
- 239000004033 plastic Substances 0.000 claims description 2
- 229920003023 plastic Polymers 0.000 claims description 2
- 238000005498 polishing Methods 0.000 claims description 2
- 125000001033 ether group Chemical group 0.000 claims 2
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 108
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 24
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 19
- 238000002360 preparation method Methods 0.000 description 17
- 125000005594 diketone group Chemical group 0.000 description 16
- 239000012071 phase Substances 0.000 description 14
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 150000002576 ketones Chemical class 0.000 description 12
- 239000011698 potassium fluoride Substances 0.000 description 12
- 235000003270 potassium fluoride Nutrition 0.000 description 12
- 238000005481 NMR spectroscopy Methods 0.000 description 11
- 239000003444 phase transfer catalyst Substances 0.000 description 11
- 239000000126 substance Substances 0.000 description 11
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Natural products CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- RRZIJNVZMJUGTK-UHFFFAOYSA-N 1,1,2-trifluoro-2-(1,2,2-trifluoroethenoxy)ethene Chemical compound FC(F)=C(F)OC(F)=C(F)F RRZIJNVZMJUGTK-UHFFFAOYSA-N 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 8
- HCDGVLDPFQMKDK-UHFFFAOYSA-N hexafluoropropylene Chemical compound FC(F)=C(F)C(F)(F)F HCDGVLDPFQMKDK-UHFFFAOYSA-N 0.000 description 8
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 7
- 238000009835 boiling Methods 0.000 description 7
- 229910052731 fluorine Inorganic materials 0.000 description 7
- 239000011737 fluorine Substances 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 150000002222 fluorine compounds Chemical class 0.000 description 6
- XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 description 6
- 239000011232 storage material Substances 0.000 description 6
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 5
- 150000001721 carbon Chemical group 0.000 description 5
- 230000003197 catalytic effect Effects 0.000 description 5
- 239000000314 lubricant Substances 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 239000003880 polar aprotic solvent Substances 0.000 description 5
- JMGNVALALWCTLC-UHFFFAOYSA-N 1-fluoro-2-(2-fluoroethenoxy)ethene Chemical compound FC=COC=CF JMGNVALALWCTLC-UHFFFAOYSA-N 0.000 description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 150000002009 diols Chemical class 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 238000004817 gas chromatography Methods 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- 238000002329 infrared spectrum Methods 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 239000000523 sample Substances 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 238000004566 IR spectroscopy Methods 0.000 description 3
- 239000004721 Polyphenylene oxide Substances 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 229910018287 SbF 5 Inorganic materials 0.000 description 3
- 239000003963 antioxidant agent Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000004140 cleaning Methods 0.000 description 3
- 239000006184 cosolvent Substances 0.000 description 3
- 150000005690 diesters Chemical class 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000006260 foam Substances 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 238000001030 gas--liquid chromatography Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 239000013529 heat transfer fluid Substances 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 229920000570 polyether Polymers 0.000 description 3
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 3
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 3
- 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
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 229910021630 Antimony pentafluoride Inorganic materials 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- VBVBHWZYQGJZLR-UHFFFAOYSA-I antimony pentafluoride Chemical compound F[Sb](F)(F)(F)F VBVBHWZYQGJZLR-UHFFFAOYSA-I 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 239000012472 biological sample Substances 0.000 description 2
- 235000011089 carbon dioxide Nutrition 0.000 description 2
- 239000003638 chemical reducing agent Substances 0.000 description 2
- 150000003983 crown ethers Chemical group 0.000 description 2
- 239000002739 cryptand Chemical group 0.000 description 2
- 230000008021 deposition Effects 0.000 description 2
- YSSSPARMOAYJTE-UHFFFAOYSA-N dibenzo-18-crown-6 Chemical compound O1CCOCCOC2=CC=CC=C2OCCOCCOC2=CC=CC=C21 YSSSPARMOAYJTE-UHFFFAOYSA-N 0.000 description 2
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 2
- 229940008406 diethyl sulfate Drugs 0.000 description 2
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 2
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000003682 fluorination reaction Methods 0.000 description 2
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 2
- 239000004519 grease Substances 0.000 description 2
- PGFXOWRDDHCDTE-UHFFFAOYSA-N hexafluoropropylene oxide Chemical compound FC(F)(F)C1(F)OC1(F)F PGFXOWRDDHCDTE-UHFFFAOYSA-N 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 2
- 239000003607 modifier Substances 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000002390 rotary evaporation Methods 0.000 description 2
- AHLATJUETSFVIM-UHFFFAOYSA-M rubidium fluoride Chemical compound [F-].[Rb+] AHLATJUETSFVIM-UHFFFAOYSA-M 0.000 description 2
- 239000004065 semiconductor Substances 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 150000003871 sulfonates Chemical class 0.000 description 2
- HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical compound CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- ZUHZGEOKBKGPSW-UHFFFAOYSA-N tetraglyme Chemical compound COCCOCCOCCOCCOC ZUHZGEOKBKGPSW-UHFFFAOYSA-N 0.000 description 2
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 2
- 239000003039 volatile agent Substances 0.000 description 2
- SAPOZTRFWJZUFT-OWOJBTEDSA-N (e)-1,1,1,2,3,4,5,5,5-nonafluoro-4-(trifluoromethyl)pent-2-ene Chemical compound FC(F)(F)C(/F)=C(\F)C(F)(C(F)(F)F)C(F)(F)F SAPOZTRFWJZUFT-OWOJBTEDSA-N 0.000 description 1
- STHIZMRUXPMSCW-UHFFFAOYSA-N 1,4,10-trioxa-7,13-diazacyclopentadecane Chemical compound C1COCCNCCOCCOCCN1 STHIZMRUXPMSCW-UHFFFAOYSA-N 0.000 description 1
- BJUOQSZSDIHZNP-UHFFFAOYSA-N 1,4,7,10-tetraoxa-13-azacyclopentadecane Chemical compound C1COCCOCCOCCOCCN1 BJUOQSZSDIHZNP-UHFFFAOYSA-N 0.000 description 1
- OYRMHTPYKXUKCS-UHFFFAOYSA-N 1-fluoropentan-3-one Chemical compound CCC(=O)CCF OYRMHTPYKXUKCS-UHFFFAOYSA-N 0.000 description 1
- XIWRBQVYCZCEPG-UHFFFAOYSA-N 17-nitro-2,5,8,11,14-pentaoxabicyclo[13.4.0]nonadeca-1(15),16,18-triene Chemical compound O1CCOCCOCCOCCOC2=CC([N+](=O)[O-])=CC=C21 XIWRBQVYCZCEPG-UHFFFAOYSA-N 0.000 description 1
- MBJIKIAWNPEHOR-UHFFFAOYSA-N 2,5,8,11,14-pentaoxabicyclo[13.4.0]nonadeca-1(15),16,18-triene-17-carbaldehyde Chemical compound O1CCOCCOCCOCCOC2=CC(C=O)=CC=C21 MBJIKIAWNPEHOR-UHFFFAOYSA-N 0.000 description 1
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 1
- AUFVJZSDSXXFOI-UHFFFAOYSA-N 2.2.2-cryptand Chemical compound C1COCCOCCN2CCOCCOCCN1CCOCCOCC2 AUFVJZSDSXXFOI-UHFFFAOYSA-N 0.000 description 1
- WDGCBNTXZHJTHJ-UHFFFAOYSA-N 2h-1,3-oxazol-2-id-4-one Chemical class O=C1CO[C-]=N1 WDGCBNTXZHJTHJ-UHFFFAOYSA-N 0.000 description 1
- VWIIJDNADIEEDB-UHFFFAOYSA-N 3-methyl-1,3-oxazolidin-2-one Chemical compound CN1CCOC1=O VWIIJDNADIEEDB-UHFFFAOYSA-N 0.000 description 1
- LVNQVIZBPSRXAN-UHFFFAOYSA-N 4,7,13,18-tetraoxa-1,10-diazabicyclo[8.5.5]icosane Chemical compound C1COCCOCCN2CCOCCN1CCOCC2 LVNQVIZBPSRXAN-UHFFFAOYSA-N 0.000 description 1
- 239000004604 Blowing Agent Substances 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 1
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-M Methanesulfonate Chemical compound CS([O-])(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 1
- 229910000792 Monel Inorganic materials 0.000 description 1
- SUAKHGWARZSWIH-UHFFFAOYSA-N N,N‐diethylformamide Chemical compound CCN(CC)C=O SUAKHGWARZSWIH-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- 229920001774 Perfluoroether Polymers 0.000 description 1
- 229920005830 Polyurethane Foam Polymers 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 229910001515 alkali metal fluoride Inorganic materials 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 125000005360 alkyl sulfoxide group Chemical group 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- LTZRCLYZVSXCTC-UHFFFAOYSA-N bis(2,5,8,11,14-pentaoxabicyclo[13.4.0]nonadeca-1(15),16,18-trien-17-ylmethyl) heptanedioate Chemical compound O1CCOCCOCCOCCOC2=CC(COC(CCCCCC(=O)OCC=3C=C4OCCOCCOCCOCCOC4=CC=3)=O)=CC=C21 LTZRCLYZVSXCTC-UHFFFAOYSA-N 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 239000012986 chain transfer agent Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 150000001924 cycloalkanes Chemical class 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 125000004386 diacrylate group Chemical group 0.000 description 1
- 150000008050 dialkyl sulfates Chemical class 0.000 description 1
- LTVOKYUPTHZZQH-UHFFFAOYSA-N difluoromethane Chemical group F[C]F LTVOKYUPTHZZQH-UHFFFAOYSA-N 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- DPCGBYPKSNCMTP-UHFFFAOYSA-N dimethyl sulfate N,N-dioctyloctan-1-amine Chemical compound COS(=O)(=O)OC.CCCCCCCCN(CCCCCCCC)CCCCCCCC DPCGBYPKSNCMTP-UHFFFAOYSA-N 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000004210 ether based solvent Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 238000000806 fluorine-19 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 239000010437 gem Substances 0.000 description 1
- 229910001751 gemstone Inorganic materials 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 229910052809 inorganic oxide Inorganic materials 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- QXLUTPDNMOEWGG-UHFFFAOYSA-N kryptand 222b Chemical compound C1COCCOCCN2CCOCCOCCN1CCOC1=CC=CC=C1OCC2 QXLUTPDNMOEWGG-UHFFFAOYSA-N 0.000 description 1
- 239000010687 lubricating oil Substances 0.000 description 1
- 238000003754 machining Methods 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 239000006078 metal deactivator Substances 0.000 description 1
- 229910001512 metal fluoride Inorganic materials 0.000 description 1
- 238000005555 metalworking Methods 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- UJMWVICAENGCRF-UHFFFAOYSA-N oxygen difluoride Chemical class FOF UJMWVICAENGCRF-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000013618 particulate matter Substances 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- XMAXUBOLEVIRGX-UHFFFAOYSA-N phosphanium;fluoride Chemical class [F-].[PH4+] XMAXUBOLEVIRGX-UHFFFAOYSA-N 0.000 description 1
- 150000004714 phosphonium salts Chemical group 0.000 description 1
- 229920002120 photoresistant polymer Polymers 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000002984 plastic foam Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 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
- 239000011496 polyurethane foam Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000003672 processing method Methods 0.000 description 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229940096017 silver fluoride Drugs 0.000 description 1
- REYHXKZHIMGNSE-UHFFFAOYSA-M silver monofluoride Chemical compound [F-].[Ag+] REYHXKZHIMGNSE-UHFFFAOYSA-M 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229910052717 sulfur Chemical group 0.000 description 1
- 239000011593 sulfur Chemical group 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000010998 test method Methods 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
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/04—Saturated compounds containing keto groups bound to acyclic carbon atoms
- C07C49/16—Saturated compounds containing keto groups bound to acyclic carbon atoms containing halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/04—Saturated compounds containing keto groups bound to acyclic carbon atoms
- C07C49/175—Saturated compounds containing keto groups bound to acyclic carbon atoms containing ether groups, groups, groups, or groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/04—Saturated compounds containing keto groups bound to acyclic carbon atoms
- C07C49/16—Saturated compounds containing keto groups bound to acyclic carbon atoms containing halogen
- C07C49/167—Saturated compounds containing keto groups bound to acyclic carbon atoms containing halogen containing only fluorine as halogen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/002—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from unsaturated compounds
- C08G65/005—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from unsaturated compounds containing halogens
- C08G65/007—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from unsaturated compounds containing halogens containing fluorine
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Detergent Compositions (AREA)
- Polyethers (AREA)
- Paints Or Removers (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US75388505P | 2005-12-23 | 2005-12-23 | |
| US60/753,885 | 2005-12-23 | ||
| US11/567,398 | 2006-12-06 | ||
| US11/567,398 US7385089B2 (en) | 2005-12-23 | 2006-12-06 | Fluorochemical ketone compounds and processes for their use |
| PCT/US2006/048637 WO2007075804A1 (en) | 2005-12-23 | 2006-12-20 | Fluorochemical ketone compounds and processes for their use |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2009521457A JP2009521457A (ja) | 2009-06-04 |
| JP2009521457A5 JP2009521457A5 (enExample) | 2010-02-12 |
| JP5280857B2 true JP5280857B2 (ja) | 2013-09-04 |
Family
ID=38222228
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2008547500A Expired - Fee Related JP5280857B2 (ja) | 2005-12-23 | 2006-12-20 | フルオロケミカルケトン化合物及びそれらの使用方法 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US7385089B2 (enExample) |
| EP (1) | EP1968927B1 (enExample) |
| JP (1) | JP5280857B2 (enExample) |
| KR (1) | KR101367006B1 (enExample) |
| CN (2) | CN101346335B (enExample) |
| WO (1) | WO2007075804A1 (enExample) |
Families Citing this family (25)
| 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 |
| US8193397B2 (en) * | 2006-12-06 | 2012-06-05 | 3M Innovative Properties Company | Hydrofluoroether compounds and processes for their preparation and use |
| US20090176148A1 (en) * | 2008-01-04 | 2009-07-09 | 3M Innovative Properties Company | Thermal management of electrochemical cells |
| US8946136B2 (en) | 2008-08-11 | 2015-02-03 | Solvay Specialty Polymers Italy S.P.A. | Hydrofluoroalcohols with improved thermal and chemical stability |
| US20100263885A1 (en) | 2009-04-21 | 2010-10-21 | 3M Innovative Properties Company | Protection systems and methods for electronic devices |
| EP2441075B2 (en) | 2009-06-12 | 2024-05-01 | ABB Schweiz AG | Dielectric insulation medium |
| DE202009009305U1 (de) | 2009-06-17 | 2009-11-05 | Ormazabal Gmbh | Schalteinrichtung für Mittel-, Hoch- oder Höchstspannung mit einem Füllmedium |
| US8193393B2 (en) * | 2010-03-26 | 2012-06-05 | 3M Innovative Properties Company | Fluoroether diketones for high temperature heat transfer |
| US8535559B2 (en) * | 2010-03-26 | 2013-09-17 | 3M Innovative Properties Company | Nitrogen-containing fluoroketones for high temperature heat transfer |
| JP6042344B2 (ja) | 2010-12-14 | 2016-12-14 | アーベーベー・テヒノロギー・アーゲー | 誘電性絶縁媒体 |
| KR20130128433A (ko) | 2010-12-14 | 2013-11-26 | 에이비비 리써치 리미티드 | 유전성 절연 매질 |
| RU2567754C2 (ru) | 2010-12-16 | 2015-11-10 | Абб Текнолоджи Аг | Диэлектрическая изолирующая среда |
| JP5748292B2 (ja) * | 2011-04-21 | 2015-07-15 | 信越化学工業株式会社 | フルオロオキシアルキレン基含有ポリマー組成物および該組成物を含む表面処理剤並びに該表面処理剤で表面処理された物品 |
| EP2718253B1 (en) * | 2011-06-10 | 2020-09-09 | 3M Innovative Properties Company | Partially fluorinated ketones and methods of making and using the same |
| WO2013087700A1 (en) | 2011-12-13 | 2013-06-20 | Abb Technology Ag | Sealed and gas insulated high voltage converter environment for offshore platforms |
| EP3084152B1 (en) * | 2013-12-20 | 2023-05-31 | 3M Innovative Properties Company | Fluorinated olefins as working fluids and methods of using same |
| WO2017167756A1 (en) * | 2016-03-31 | 2017-10-05 | Solvay Specialty Polymers Italy S.P.A. | Method of making fluorine group-containing aromatic compounds |
| CN106554262B (zh) * | 2016-09-23 | 2022-05-20 | 天津市长芦化工新材料有限公司 | 全氟九碳酮及其应用 |
| KR102730629B1 (ko) * | 2017-12-13 | 2024-11-14 | 쓰리엠 이노베이티브 프로퍼티즈 컴파니 | 퍼플루오르화 1-알콕시프로펜, 조성물, 및 이를 사용하기 위한 방법 및 장치 |
| KR102351623B1 (ko) * | 2018-05-14 | 2022-01-14 | 주식회사 엘지에너지솔루션 | 분리막 기재가 없는 분리막 |
| JP7693699B2 (ja) * | 2020-03-05 | 2025-06-17 | シクパ ホルディング ソシエテ アノニム | 紫外可視放射硬化性セキュリティインク |
| CN111909752B (zh) * | 2020-08-26 | 2021-09-28 | 武汉理工大学 | 一种氟素润滑添加剂及其制备方法、及润滑材料 |
| CN113604202B (zh) * | 2021-06-25 | 2023-07-04 | 浙江巨化技术中心有限公司 | 一种组合物、浸没式液冷剂及其应用以及浸没式液冷系统 |
| CN115260019B (zh) * | 2022-08-04 | 2024-03-26 | 三明市海斯福化工有限责任公司 | 一种高支化全氟酮及其在热传导工作中的应用 |
| CN115651184A (zh) * | 2022-09-28 | 2023-01-31 | 四川弘氟新材料有限公司 | 一种含氟聚醚羧酸型表面活性剂及其制备方法 |
Family Cites Families (48)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1968049A (en) | 1930-02-08 | 1934-07-31 | Gen Motors Corp | Heat transfer and refrigeration |
| US3185734A (en) | 1960-10-25 | 1965-05-25 | Du Pont | Novel polyfluoro-substituted ketones and their preparation from polyfluoro acid fluorides |
| DE1298514B (de) | 1965-12-02 | 1969-07-03 | Hoechst Ag | Verfahren zur Herstellung von Perfluoralkyl-alkyl-aethern |
| SE371829B (enExample) * | 1966-07-11 | 1974-12-02 | Montedison Spa | |
| US3847978A (en) * | 1968-07-01 | 1974-11-12 | Montedison Spa | Perfluorinated linear polyethers having reactive terminal groups at both ends of the chain and process for the preparation thereof |
| US3810874A (en) | 1969-03-10 | 1974-05-14 | Minnesota Mining & Mfg | Polymers prepared from poly(perfluoro-alkylene oxide) compounds |
| US3903012A (en) | 1973-02-14 | 1975-09-02 | Du Pont | Water-displacement compositions containing fluorine compound and surfactant |
| FR2287432A1 (fr) | 1974-10-10 | 1976-05-07 | Poudres & Explosifs Ste Nale | Nouveaux ethers fluores et leur procede de preparation |
| DE2521594C2 (de) | 1975-05-15 | 1984-03-15 | Hoechst Ag, 6230 Frankfurt | Verfahren zur Herstellung perfluorierter Ketone |
| US4169807A (en) | 1978-03-20 | 1979-10-02 | Rca Corporation | Novel solvent drying agent |
| EP0609200A1 (en) | 1988-12-02 | 1994-08-10 | Minnesota Mining And Manufacturing Company | Direct fluorination process for making perfluorinated organic substances |
| CA2026165A1 (en) | 1989-10-19 | 1991-04-20 | John C. Hansen | Perfluoro-n,n,n',n'-tetrapropyldiaminopropane and use thereof in vapor phase heating |
| IT1237887B (it) | 1989-12-12 | 1993-06-18 | Ausimont Spa | Lubrificanti perfluoropolieterei aventi proprieta' antiusura |
| US5023009A (en) | 1990-10-03 | 1991-06-11 | E. I. Du Pont De Nemours And Company | Binary azeotropic compositions of 1,1,1,2,3,3-hexafluoro-3-methoxypropane and 2,2,3,3,3-pentafluoropropanol-1 |
| JPH082893B2 (ja) | 1991-04-16 | 1996-01-17 | 信越化学工業株式会社 | パーフルオロ環状ケトン及びその製造法 |
| US5125978A (en) | 1991-04-19 | 1992-06-30 | Minnesota Mining And Manufacturing Company | Water displacement composition and a method of use |
| IT1249319B (it) | 1991-04-26 | 1995-02-22 | Ausimont Spa | Perfluoropolieteri ad elevata viscosita' e basso contenuto di ossigeno perossidico, e procedimento per la loro preparazione |
| US5210106A (en) | 1991-10-04 | 1993-05-11 | Minnesota Mining And Manufacturing Company | Fine-celled plastic foam containing fluorochemical blowing agent |
| US5182342A (en) | 1992-02-28 | 1993-01-26 | E. I. Du Pont De Nemours And Company | Hydrofluorocarbon solvents for fluoromonomer polymerization |
| US5605882A (en) | 1992-05-28 | 1997-02-25 | E. I. Du Pont De Nemours And Company | Azeotrope(like) compositions of pentafluorodimethyl ether and difluoromethane |
| US5264508A (en) | 1992-06-25 | 1993-11-23 | The Dow Chemical Company | Polymers of haloperfluoro and perfluoro ethers |
| US5316686A (en) * | 1993-01-11 | 1994-05-31 | The United States Of America As Represented By The Secretary Of The Air Force | Perfluoroalkylether tertiary alcohols |
| US5453575A (en) * | 1993-02-01 | 1995-09-26 | Endosonics Corporation | Apparatus and method for detecting blood flow in intravascular ultrasonic imaging |
| US5539008A (en) | 1993-12-29 | 1996-07-23 | Minnesota Mining And Manufacturing Company | Foamable composition containing unsaturated perfluorochemical blowing agent |
| US5466877A (en) | 1994-03-15 | 1995-11-14 | Minnesota Mining And Manufacturing Company | Process for converting perfluorinated esters to perfluorinated acyl fluorides and/or ketones |
| US5925611A (en) | 1995-01-20 | 1999-07-20 | Minnesota Mining And Manufacturing Company | Cleaning process and composition |
| JPH10506926A (ja) | 1995-06-07 | 1998-07-07 | イー・アイ・デユポン・ドウ・ヌムール・アンド・カンパニー | ヒドロフルオロエーテルまたはフルオロエーテルをベースにした冷媒 |
| DE69611930T3 (de) | 1995-10-20 | 2010-05-20 | Minnesota Mining And Mfg. Co., Saint Paul | Hydrofluorether als tieftemperaturkühlmittel |
| US5827446A (en) | 1996-01-31 | 1998-10-27 | E. I. Du Pont De Nemours And Company | Nonafluoromethoxybutane compositions |
| US5750797A (en) * | 1996-04-15 | 1998-05-12 | Minnesota Mining And Manufacturing Company | Process for the production of hydrofluoroethers |
| US5851436A (en) | 1996-06-13 | 1998-12-22 | E. I. Du Pont De Nemours And Company | Nonafluoromethoxybutane compositions |
| JP2869432B2 (ja) | 1996-10-04 | 1999-03-10 | 工業技術院長 | 溶剤及びそれを用いる物品表面の清浄化方法 |
| JP2952414B2 (ja) | 1997-09-22 | 1999-09-27 | 工業技術院長 | 溶剤及びそれを用いる物品表面の清浄化方法 |
| US6046368A (en) | 1998-03-17 | 2000-04-04 | 3M Innovative Properties Company | Catalytic process for making hydrofluoroethers |
| US6080448A (en) | 1998-04-03 | 2000-06-27 | Preservation Technologies Lp | Deacidification of cellulose based materials using hydrofluoroether carriers |
| WO2000032655A1 (en) | 1998-11-30 | 2000-06-08 | E.I. Du Pont De Nemours And Company | Fluoromonomer polymerization |
| JP3141325B2 (ja) | 1999-01-14 | 2001-03-05 | 工業技術院長 | 溶剤およびそれを用いる物品表面の清浄化方法 |
| JP4666855B2 (ja) | 1999-07-20 | 2011-04-06 | スリーエム イノベイティブ プロパティズ カンパニー | 消火組成物中でのフッ素化ケトンの使用法 |
| US6374907B1 (en) | 1999-10-08 | 2002-04-23 | 3M Innovative Properties Company | Hydrofluoroether as a heat-transfer fluid |
| DE60118576T2 (de) | 2000-08-18 | 2006-11-02 | 3M Innovative Properties Co., Saint Paul | Fluoro(meth)acrylatecopolymer-beschichtungsmassen |
| US6394107B1 (en) | 2001-04-24 | 2002-05-28 | 3M Innovative Properties Company | Use of fluorinated ketones as wet cleaning agents for vapor reactors and vapor reactor components |
| US6403149B1 (en) | 2001-04-24 | 2002-06-11 | 3M Innovative Properties Company | Fluorinated ketones as lubricant deposition solvents for magnetic media applications |
| ITMI20011340A1 (it) | 2001-06-26 | 2002-12-26 | Ausimont Spa | Pfpe aventi almeno un terminale alchiletereo e relativo processo dipreparazione |
| US6423673B1 (en) | 2001-09-07 | 2002-07-23 | 3M Innovation Properties Company | Azeotrope-like compositions and their use |
| 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 |
| EP1306417B1 (en) * | 2001-10-23 | 2012-08-01 | Solvay Specialty Polymers Italy S.p.A. | Use of fluorinated liquids for the heat exchange or as working fluids in the presence of ionizing radiations and/or irradiation with neutrons |
| ITMI20030019A1 (it) * | 2003-01-09 | 2004-07-10 | Solvay Solexis Spa | Procedimento per la preparazione di composti mono- |
| US7100380B2 (en) | 2004-02-03 | 2006-09-05 | United Technologies Corporation | Organic rankine cycle fluid |
-
2006
- 2006-12-06 US US11/567,398 patent/US7385089B2/en not_active Expired - Fee Related
- 2006-12-20 JP JP2008547500A patent/JP5280857B2/ja not_active Expired - Fee Related
- 2006-12-20 KR KR1020087014920A patent/KR101367006B1/ko not_active Expired - Fee Related
- 2006-12-20 EP EP06847842.9A patent/EP1968927B1/en not_active Not-in-force
- 2006-12-20 CN CN2006800485805A patent/CN101346335B/zh not_active Expired - Fee Related
- 2006-12-20 CN CN2012100313346A patent/CN102617306A/zh active Pending
- 2006-12-20 WO PCT/US2006/048637 patent/WO2007075804A1/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| WO2007075804A1 (en) | 2007-07-05 |
| CN102617306A (zh) | 2012-08-01 |
| EP1968927B1 (en) | 2014-08-27 |
| US7385089B2 (en) | 2008-06-10 |
| EP1968927A1 (en) | 2008-09-17 |
| JP2009521457A (ja) | 2009-06-04 |
| KR101367006B1 (ko) | 2014-02-24 |
| US20070163710A1 (en) | 2007-07-19 |
| KR20080080320A (ko) | 2008-09-03 |
| CN101346335A (zh) | 2009-01-14 |
| CN101346335B (zh) | 2013-04-24 |
| EP1968927A4 (en) | 2011-08-03 |
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