KR101411750B1 - 환형 하이드로플루오로에테르 화합물과 그의 제조 및 사용 방법 - Google Patents
환형 하이드로플루오로에테르 화합물과 그의 제조 및 사용 방법 Download PDFInfo
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- KR101411750B1 KR101411750B1 KR1020087028093A KR20087028093A KR101411750B1 KR 101411750 B1 KR101411750 B1 KR 101411750B1 KR 1020087028093 A KR1020087028093 A KR 1020087028093A KR 20087028093 A KR20087028093 A KR 20087028093A KR 101411750 B1 KR101411750 B1 KR 101411750B1
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- Prior art keywords
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- ocf
- compound
- hydrofluoroether
- fluoride
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 78
- 238000000034 method Methods 0.000 title claims description 37
- 238000002360 preparation method Methods 0.000 title description 14
- 125000004122 cyclic group Chemical group 0.000 title description 5
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 36
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 35
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 25
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 22
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 20
- 239000000203 mixture Substances 0.000 claims description 77
- 239000002904 solvent Substances 0.000 claims description 25
- 239000000463 material Substances 0.000 claims description 21
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 18
- 125000001153 fluoro group Chemical group F* 0.000 claims description 10
- 239000007788 liquid Substances 0.000 claims description 10
- 239000011248 coating agent Substances 0.000 claims description 8
- 238000000576 coating method Methods 0.000 claims description 8
- 239000011551 heat transfer agent Substances 0.000 claims description 8
- 239000000758 substrate Substances 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 229910000679 solder Inorganic materials 0.000 claims description 6
- 238000012546 transfer Methods 0.000 claims description 5
- 239000012808 vapor phase Substances 0.000 claims description 4
- 238000005476 soldering Methods 0.000 claims description 3
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 2
- 150000003512 tertiary amines Chemical class 0.000 claims description 2
- -1 butylidene part Chemical group 0.000 abstract description 32
- 239000011737 fluorine Substances 0.000 abstract description 19
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 abstract description 17
- 125000004432 carbon atom Chemical group C* 0.000 abstract description 17
- 150000002222 fluorine compounds Chemical class 0.000 abstract description 17
- 229910052799 carbon Inorganic materials 0.000 abstract description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract description 6
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 abstract description 6
- 125000000623 heterocyclic group Chemical group 0.000 abstract description 4
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 159
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 32
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 27
- 239000000047 product Substances 0.000 description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 23
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 19
- 239000003444 phase transfer catalyst Substances 0.000 description 17
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 16
- 239000011698 potassium fluoride Substances 0.000 description 16
- 235000003270 potassium fluoride Nutrition 0.000 description 16
- 239000000543 intermediate Substances 0.000 description 13
- 150000001721 carbon Chemical group 0.000 description 11
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 11
- 229910052751 metal Inorganic materials 0.000 description 11
- 239000002184 metal Substances 0.000 description 11
- 208000033962 Fontaine progeroid syndrome Diseases 0.000 description 10
- 238000003682 fluorination reaction Methods 0.000 description 10
- 239000012071 phase Substances 0.000 description 10
- 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 9
- KNURRSZDMIXZLO-UHFFFAOYSA-N 2,2,3,3-tetrafluorobutanedioyl difluoride Chemical compound FC(=O)C(F)(F)C(F)(F)C(F)=O KNURRSZDMIXZLO-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 238000005481 NMR spectroscopy Methods 0.000 description 9
- 125000005594 diketone group Chemical group 0.000 description 9
- 238000000746 purification Methods 0.000 description 9
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 8
- 239000003054 catalyst Substances 0.000 description 8
- 238000004508 fractional distillation Methods 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 7
- 230000029936 alkylation Effects 0.000 description 7
- 238000005804 alkylation reaction Methods 0.000 description 7
- 238000009835 boiling Methods 0.000 description 7
- 238000004821 distillation Methods 0.000 description 7
- 239000012530 fluid Substances 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 239000002168 alkylating agent Substances 0.000 description 6
- 229940100198 alkylating agent Drugs 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 6
- HCDGVLDPFQMKDK-UHFFFAOYSA-N hexafluoropropylene Chemical compound FC(F)=C(F)C(F)(F)F HCDGVLDPFQMKDK-UHFFFAOYSA-N 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 229910001220 stainless steel Inorganic materials 0.000 description 6
- 239000010935 stainless steel Substances 0.000 description 6
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 5
- 229940008406 diethyl sulfate Drugs 0.000 description 5
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 5
- 238000004817 gas chromatography Methods 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- ODVREDGIWSDQFD-UHFFFAOYSA-N 3-(4-methylphenyl)sulfonyloxypropyl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OCCCOS(=O)(=O)C1=CC=C(C)C=C1 ODVREDGIWSDQFD-UHFFFAOYSA-N 0.000 description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- 0 CC(*C(*)(*)C(C(F)(F)F)(O*)O1)(C1(C(F)(F)F)F)F Chemical compound CC(*C(*)(*)C(C(F)(F)F)(O*)O1)(C1(C(F)(F)F)F)F 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- RBHJBMIOOPYDBQ-UHFFFAOYSA-N carbon dioxide;propan-2-one Chemical compound O=C=O.CC(C)=O RBHJBMIOOPYDBQ-UHFFFAOYSA-N 0.000 description 4
- 239000011195 cermet Substances 0.000 description 4
- 239000002131 composite material Substances 0.000 description 4
- 239000000356 contaminant Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 238000000151 deposition Methods 0.000 description 4
- 125000003709 fluoroalkyl group Chemical group 0.000 description 4
- 238000002329 infrared spectrum Methods 0.000 description 4
- 150000002576 ketones Chemical class 0.000 description 4
- 239000000314 lubricant Substances 0.000 description 4
- 239000000178 monomer Substances 0.000 description 4
- JMGNVALALWCTLC-UHFFFAOYSA-N 1-fluoro-2-(2-fluoroethenoxy)ethene Chemical compound FC=COC=CF JMGNVALALWCTLC-UHFFFAOYSA-N 0.000 description 3
- XAKMJUAGVWKMOB-UHFFFAOYSA-N 2,2,3,3,4,4-hexafluoropentanedioyl difluoride Chemical compound FC(=O)C(F)(F)C(F)(F)C(F)(F)C(F)=O XAKMJUAGVWKMOB-UHFFFAOYSA-N 0.000 description 3
- XGOQVZMOVVMZIL-UHFFFAOYSA-N 2,2,3-trifluoro-3-(trifluoromethyl)butanedioyl difluoride Chemical compound FC(=O)C(F)(F)C(F)(C(F)=O)C(F)(F)F XGOQVZMOVVMZIL-UHFFFAOYSA-N 0.000 description 3
- FPTYZBDNBMVYCL-UHFFFAOYSA-N 3-methyl-5-nitro-1h-pyridin-2-one Chemical compound CC1=CC([N+]([O-])=O)=CN=C1O FPTYZBDNBMVYCL-UHFFFAOYSA-N 0.000 description 3
- 239000004604 Blowing Agent Substances 0.000 description 3
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 150000004703 alkoxides Chemical class 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- 239000003963 antioxidant agent Substances 0.000 description 3
- 239000000010 aprotic solvent Substances 0.000 description 3
- 238000004140 cleaning Methods 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 239000006260 foam Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 3
- 238000002390 rotary evaporation Methods 0.000 description 3
- 239000004065 semiconductor Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 3
- 238000005406 washing Methods 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
- BZPCMSSQHRAJCC-UHFFFAOYSA-N 1,2,3,3,4,4,5,5,5-nonafluoro-1-(1,2,3,3,4,4,5,5,5-nonafluoropent-1-enoxy)pent-1-ene Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)=C(F)OC(F)=C(F)C(F)(F)C(F)(F)C(F)(F)F BZPCMSSQHRAJCC-UHFFFAOYSA-N 0.000 description 2
- SYNPRNNJJLRHTI-UHFFFAOYSA-N 2-(hydroxymethyl)butane-1,4-diol Chemical compound OCCC(CO)CO SYNPRNNJJLRHTI-UHFFFAOYSA-N 0.000 description 2
- CLVZVRUCGYJYAJ-UHFFFAOYSA-N 2-ethoxy-3,3,4,4-tetrafluoro-2,5-bis(1,1,1,2,3,3,3-heptafluoropropan-2-yl)oxolane Chemical compound CCOC1(C(F)(C(F)(F)F)C(F)(F)F)OC(C(F)(C(F)(F)F)C(F)(F)F)C(F)(F)C1(F)F CLVZVRUCGYJYAJ-UHFFFAOYSA-N 0.000 description 2
- QMNFXPVNVFCSRL-UHFFFAOYSA-N 3,3,4,4-tetrafluoro-2,5-bis(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-2-methoxyoxolane Chemical compound FC(F)(F)C(F)(C(F)(F)F)C1(OC)OC(C(F)(C(F)(F)F)C(F)(F)F)C(F)(F)C1(F)F QMNFXPVNVFCSRL-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
- RJFAYQIBOAGBLC-BYPYZUCNSA-N Selenium-L-methionine Chemical compound C[Se]CC[C@H](N)C(O)=O RJFAYQIBOAGBLC-BYPYZUCNSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 229910001515 alkali metal fluoride Inorganic materials 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000006184 cosolvent Substances 0.000 description 2
- 150000003983 crown ethers Chemical group 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000005520 cutting process Methods 0.000 description 2
- 230000008021 deposition Effects 0.000 description 2
- 150000008050 dialkyl sulfates Chemical class 0.000 description 2
- JYCKNDWZDXGNBW-UHFFFAOYSA-N dipropyl sulfate Chemical compound CCCOS(=O)(=O)OCCC JYCKNDWZDXGNBW-UHFFFAOYSA-N 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000004428 fluoroalkoxy group Chemical group 0.000 description 2
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 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
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- UJMWVICAENGCRF-UHFFFAOYSA-N oxygen difluoride Chemical class FOF UJMWVICAENGCRF-UHFFFAOYSA-N 0.000 description 2
- 239000010702 perfluoropolyether Substances 0.000 description 2
- 238000007539 photo-oxidation reaction Methods 0.000 description 2
- 239000003505 polymerization initiator Substances 0.000 description 2
- 230000000379 polymerizing effect Effects 0.000 description 2
- 229920002635 polyurethane Polymers 0.000 description 2
- 239000004814 polyurethane Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- AHLATJUETSFVIM-UHFFFAOYSA-M rubidium fluoride Chemical compound [F-].[Rb+] AHLATJUETSFVIM-UHFFFAOYSA-M 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 238000004513 sizing Methods 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 238000001256 steam distillation Methods 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 239000000126 substance Substances 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
- 230000008016 vaporization Effects 0.000 description 2
- 238000010792 warming Methods 0.000 description 2
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 1
- WXUAQHNMJWJLTG-VKHMYHEASA-N (S)-methylsuccinic acid Chemical compound OC(=O)[C@@H](C)CC(O)=O WXUAQHNMJWJLTG-VKHMYHEASA-N 0.000 description 1
- LVGUZGTVOIAKKC-UHFFFAOYSA-N 1,1,1,2-tetrafluoroethane Chemical compound FCC(F)(F)F LVGUZGTVOIAKKC-UHFFFAOYSA-N 0.000 description 1
- JGTNAGYHADQMCM-UHFFFAOYSA-M 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F JGTNAGYHADQMCM-UHFFFAOYSA-M 0.000 description 1
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 1
- 229940035437 1,3-propanediol Drugs 0.000 description 1
- NLMDJJTUQPXZFG-UHFFFAOYSA-N 1,4,10,13-tetraoxa-7,16-diazacyclooctadecane Chemical compound C1COCCOCCNCCOCCOCCN1 NLMDJJTUQPXZFG-UHFFFAOYSA-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
- 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
- KJGYBFLEIPDFNQ-UHFFFAOYSA-N 2,2,2-trifluoroethyl 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate Chemical compound FC(F)(F)COS(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F KJGYBFLEIPDFNQ-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
- YUQQROSBMZNBAL-UHFFFAOYSA-N 2-ethoxy-3,3,4,4,5,5,6-heptafluoro-2,6-bis(1,1,1,2,3,3,3-heptafluoropropan-2-yl)oxane Chemical compound CCOC1(C(F)(C(F)(F)F)C(F)(F)F)OC(F)(C(F)(C(F)(F)F)C(F)(F)F)C(F)(F)C(F)(F)C1(F)F YUQQROSBMZNBAL-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
- MECNNJDGCQURPB-UHFFFAOYSA-N 3,3,4,4-tetrafluoro-2,5-bis(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-2-propoxyoxolane Chemical compound CCCOC1(C(F)(C(F)(F)F)C(F)(F)F)OC(C(F)(C(F)(F)F)C(F)(F)F)C(F)(F)C1(F)F MECNNJDGCQURPB-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
- COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 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
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 1
- 241001546602 Horismenus Species 0.000 description 1
- 238000004566 IR spectroscopy Methods 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
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-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
- 230000009102 absorption Effects 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- GPWHDDKQSYOYBF-UHFFFAOYSA-N ac1l2u0q Chemical compound Br[Br-]Br GPWHDDKQSYOYBF-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
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001335 aliphatic alkanes 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
- 150000001408 amides Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 125000003118 aryl group Chemical group 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
- 230000001588 bifunctional effect Effects 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 238000005219 brazing Methods 0.000 description 1
- ZPFKRQXYKULZKP-UHFFFAOYSA-N butylidene Chemical group [CH2+]CC[CH-] ZPFKRQXYKULZKP-UHFFFAOYSA-N 0.000 description 1
- 229930188620 butyrolactone Natural products 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 150000001734 carboxylic acid salts Chemical class 0.000 description 1
- 238000005234 chemical deposition Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 230000001276 controlling effect Effects 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 239000002739 cryptand Chemical group 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- 150000001924 cycloalkanes Chemical class 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- YSSSPARMOAYJTE-UHFFFAOYSA-N dibenzo-18-crown-6 Chemical compound O1CCOCCOC2=CC=CC=C2OCCOCCOC2=CC=CC=C21 YSSSPARMOAYJTE-UHFFFAOYSA-N 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000005108 dry cleaning Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000004210 ether based solvent Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 238000000806 fluorine-19 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 229920001973 fluoroelastomer Polymers 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000010437 gem Substances 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 239000004519 grease Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 231100001261 hazardous Toxicity 0.000 description 1
- 239000013529 heat transfer fluid Substances 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
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- 229910000040 hydrogen fluoride 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
- 239000004615 ingredient 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
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- QXLUTPDNMOEWGG-UHFFFAOYSA-N kryptand 222b Chemical compound C1COCCOCCN2CCOCCOCCN1CCOC1=CC=CC=C1OCC2 QXLUTPDNMOEWGG-UHFFFAOYSA-N 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 230000001050 lubricating effect Effects 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 239000006078 metal deactivator Substances 0.000 description 1
- 229910001512 metal fluoride Inorganic materials 0.000 description 1
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 1
- VUQUOGPMUUJORT-UHFFFAOYSA-N methyl 4-methylbenzenesulfonate Chemical compound COS(=O)(=O)C1=CC=C(C)C=C1 VUQUOGPMUUJORT-UHFFFAOYSA-N 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- XTAZYLNFDRKIHJ-UHFFFAOYSA-N n,n-dioctyloctan-1-amine Chemical compound CCCCCCCCN(CCCCCCCC)CCCCCCCC XTAZYLNFDRKIHJ-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 239000013618 particulate matter Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- XMAXUBOLEVIRGX-UHFFFAOYSA-N phosphanium;fluoride Chemical group [F-].[PH4+] XMAXUBOLEVIRGX-UHFFFAOYSA-N 0.000 description 1
- 150000004714 phosphonium salts Chemical group 0.000 description 1
- 238000000206 photolithography Methods 0.000 description 1
- 229920002120 photoresistant polymer Polymers 0.000 description 1
- 238000005240 physical vapour deposition Methods 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
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- 239000002984 plastic foam Substances 0.000 description 1
- 239000003880 polar aprotic solvent Substances 0.000 description 1
- 229920000570 polyether Polymers 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
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000034563 regulation of cell size Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
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- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000007493 shaping process Methods 0.000 description 1
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- 239000010703 silicon Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
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- 238000011105 stabilization Methods 0.000 description 1
- 239000011232 storage material Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
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- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000011289 tar acid Substances 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
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D307/18—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/20—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D309/10—Oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Furan Compounds (AREA)
- Pyrane Compounds (AREA)
- Lubricants (AREA)
- Polyurethanes Or Polyureas (AREA)
- Paints Or Removers (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (5)
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| US74774206P | 2006-05-19 | 2006-05-19 | |
| US60/747,742 | 2006-05-19 | ||
| US11/567,602 | 2006-12-06 | ||
| US11/567,602 US8791254B2 (en) | 2006-05-19 | 2006-12-06 | Cyclic hydrofluoroether compounds and processes for their preparation and use |
| PCT/US2007/066707 WO2007136948A2 (en) | 2006-05-19 | 2007-04-16 | Cyclic hydrofluoroether compounds and processes for their preparation and use |
Publications (2)
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|---|---|
| KR20090010061A KR20090010061A (ko) | 2009-01-28 |
| KR101411750B1 true KR101411750B1 (ko) | 2014-06-25 |
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| US (1) | US8791254B2 (https=) |
| EP (1) | EP2027100B1 (https=) |
| JP (1) | JP2009537634A (https=) |
| KR (1) | KR101411750B1 (https=) |
| CN (1) | CN101448806B (https=) |
| TW (1) | TWI412524B (https=) |
| WO (1) | WO2007136948A2 (https=) |
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| FR2915997B1 (fr) * | 2007-05-07 | 2009-07-03 | Rhodia Recherches & Tech | Traitement anti-graffitis. |
| US20090176148A1 (en) * | 2008-01-04 | 2009-07-09 | 3M Innovative Properties Company | Thermal management of electrochemical cells |
| US20100263885A1 (en) | 2009-04-21 | 2010-10-21 | 3M Innovative Properties Company | Protection systems and methods for electronic devices |
| BRPI0924862A2 (pt) | 2009-06-12 | 2016-08-23 | Abb Technology Ag | meio de isolação dielétrica |
| DE202009009305U1 (de) | 2009-06-17 | 2009-11-05 | Ormazabal Gmbh | Schalteinrichtung für Mittel-, Hoch- oder Höchstspannung mit einem Füllmedium |
| 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 |
| US9259219B2 (en) * | 2009-11-09 | 2016-02-16 | Ethicon, Llc | Surgical needle coatings and methods |
| US9221075B2 (en) | 2009-11-09 | 2015-12-29 | Ethicon, Inc. | Surgical needle coatings and methods |
| US9332982B2 (en) * | 2009-11-09 | 2016-05-10 | Ethicon, Llc | Surgical needle coatings and methods |
| US8535559B2 (en) * | 2010-03-26 | 2013-09-17 | 3M Innovative Properties Company | Nitrogen-containing fluoroketones for high temperature heat transfer |
| US8193393B2 (en) | 2010-03-26 | 2012-06-05 | 3M Innovative Properties Company | Fluoroether diketones for high temperature heat transfer |
| KR20130128433A (ko) | 2010-12-14 | 2013-11-26 | 에이비비 리써치 리미티드 | 유전성 절연 매질 |
| DK2652752T3 (en) | 2010-12-14 | 2016-01-11 | Abb Technology Ag | Dielectric INSULATION MEDIUM |
| RU2567754C2 (ru) | 2010-12-16 | 2015-11-10 | Абб Текнолоджи Аг | Диэлектрическая изолирующая среда |
| JP2014509302A (ja) * | 2010-12-21 | 2014-04-17 | ソルヴェイ・スペシャルティ・ポリマーズ・イタリー・エッセ・ピ・ア | フッ素化有機化合物の製造方法 |
| EP2688973A1 (en) | 2011-03-25 | 2014-01-29 | 3M Innovative Properties Company | Fluorinated oxiranes as heat transfer fluids |
| WO2013087700A1 (en) | 2011-12-13 | 2013-06-20 | Abb Technology Ag | Sealed and gas insulated high voltage converter environment for offshore platforms |
| KR102341140B1 (ko) * | 2013-07-25 | 2021-12-21 | 쓰리엠 이노베이티브 프로퍼티즈 컴파니 | 질소 함유 하이드로플루오로에테르 및 이의 제조 방법 |
| WO2016048808A1 (en) * | 2014-09-23 | 2016-03-31 | 3M Innovative Properties Company | Nitrogen containing hydrofluoroethers and methods of using same |
| JP6905986B2 (ja) * | 2015-12-24 | 2021-07-21 | スリーエム イノベイティブ プロパティズ カンパニー | フッ素化化合物を変換するための方法 |
| 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 |
| EP3426651A4 (en) * | 2016-03-11 | 2019-08-21 | 3M Innovative Properties Company | AMINO-CONTAINING CYCLIC HYDROFLUOROETHERS AND METHODS OF USE THEREOF |
| US11197666B2 (en) | 2017-09-15 | 2021-12-14 | Cilag Gmbh International | Surgical coated needles |
| US11673861B2 (en) * | 2017-12-13 | 2023-06-13 | 3M Innovative Properties Company | Perfluorinated 1-alkoxypropenes, compositions, and methods and apparatuses for using same |
| US11325893B2 (en) | 2018-09-26 | 2022-05-10 | 3M Innovative Properties Company | Hydrofluoroethers and methods of using same |
| US12414267B2 (en) | 2019-06-12 | 2025-09-09 | 3M Innovative Properties Company | Fluorinated aromatics and methods of using same |
| EP4121405A1 (en) * | 2020-03-19 | 2023-01-25 | 3M Innovative Properties Company | Perfluorinated allyl ethers and perfluorinated allyl amines and methods of making and using the same |
| US12263622B1 (en) | 2021-01-04 | 2025-04-01 | Holcim Technology Ltd | Process for producing isocyanate-based foam construction boards |
| CN115970620A (zh) * | 2022-12-23 | 2023-04-18 | 浙江工业大学 | 一种二元对称型氢氟醚的生产工艺及装置 |
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| WO1984002909A1 (en) | 1983-01-20 | 1984-08-02 | Electricity Council | Fluorinated ethers |
| EP0496415A1 (en) * | 1991-01-25 | 1992-07-29 | AUSIMONT S.p.A. | Perfluorinated cyclic hemiketals, corresponding perfluorodiketones and process for preparing them |
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| US3700695A (en) * | 1969-10-16 | 1972-10-24 | Hooker Chemical Corp | Fluorinated tetrahydro-pyrans |
| US3903012A (en) | 1973-02-14 | 1975-09-02 | Du Pont | Water-displacement compositions containing fluorine compound and surfactant |
| NL7413128A (nl) | 1973-10-10 | 1975-04-14 | Hoechst Ag | Werkwijze voor het bereiden van perfluorcyclo- ethers. |
| 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 |
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| DE2623090A1 (de) * | 1976-05-22 | 1977-12-08 | Hoechst Ag | Verfahren zur herstellung von perfluor-alpha- (3,6-dimethyl-1,4- dioxanyl-2-oxy)-propionsaeurefluorid |
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| GB9200181D0 (en) * | 1992-01-07 | 1992-02-26 | Whitford Plastics | Non-stick coatings |
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| US6548471B2 (en) * | 1995-01-20 | 2003-04-15 | 3M Innovative Properties Company | Alkoxy-substituted perfluorocompounds |
| US5925611A (en) | 1995-01-20 | 1999-07-20 | Minnesota Mining And Manufacturing Company | Cleaning process and composition |
| CA2233874A1 (en) | 1995-10-20 | 1997-04-24 | Gregory J. Sherwood | Hydrofluoroethers as low temperature refrigerants |
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| US6013795A (en) | 1996-11-04 | 2000-01-11 | 3M Innovative Properties Company | Alpha-branched fluoroalkylcarbonyl fluorides and their derivatives |
| US6005137A (en) | 1997-06-10 | 1999-12-21 | 3M Innovative Properties Company | Halogenated acrylates and polymers derived therefrom |
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2006
- 2006-12-06 US US11/567,602 patent/US8791254B2/en active Active
-
2007
- 2007-04-16 CN CN2007800183513A patent/CN101448806B/zh not_active Expired - Fee Related
- 2007-04-16 EP EP07781976.1A patent/EP2027100B1/en not_active Not-in-force
- 2007-04-16 JP JP2009512196A patent/JP2009537634A/ja not_active Withdrawn
- 2007-04-16 WO PCT/US2007/066707 patent/WO2007136948A2/en not_active Ceased
- 2007-04-16 KR KR1020087028093A patent/KR101411750B1/ko active Active
- 2007-05-18 TW TW096117802A patent/TWI412524B/zh active
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| WO1984002909A1 (en) | 1983-01-20 | 1984-08-02 | Electricity Council | Fluorinated ethers |
| EP0496415A1 (en) * | 1991-01-25 | 1992-07-29 | AUSIMONT S.p.A. | Perfluorinated cyclic hemiketals, corresponding perfluorodiketones and process for preparing them |
Also Published As
| Publication number | Publication date |
|---|---|
| TWI412524B (zh) | 2013-10-21 |
| US8791254B2 (en) | 2014-07-29 |
| JP2009537634A (ja) | 2009-10-29 |
| EP2027100B1 (en) | 2016-05-25 |
| CN101448806A (zh) | 2009-06-03 |
| US20070267464A1 (en) | 2007-11-22 |
| KR20090010061A (ko) | 2009-01-28 |
| TW200804326A (en) | 2008-01-16 |
| WO2007136948A2 (en) | 2007-11-29 |
| CN101448806B (zh) | 2013-01-02 |
| WO2007136948A3 (en) | 2008-01-24 |
| EP2027100A2 (en) | 2009-02-25 |
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