WO2013086264A1 - Composition comprising fluoroalkyl perfluoroalkene ethers and uses thereof - Google Patents
Composition comprising fluoroalkyl perfluoroalkene ethers and uses thereof Download PDFInfo
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- WO2013086264A1 WO2013086264A1 PCT/US2012/068358 US2012068358W WO2013086264A1 WO 2013086264 A1 WO2013086264 A1 WO 2013086264A1 US 2012068358 W US2012068358 W US 2012068358W WO 2013086264 A1 WO2013086264 A1 WO 2013086264A1
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- WIPO (PCT)
- Prior art keywords
- propyl
- cfcf
- composition
- xcf
- formula
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- 239000000203 mixture Substances 0.000 title claims abstract description 155
- 150000002170 ethers Chemical class 0.000 title claims description 21
- 125000003709 fluoroalkyl group Chemical group 0.000 title description 17
- -1 2,2,3,3-tetrafluoro-1 -propyl Chemical group 0.000 claims abstract description 128
- 238000000034 method Methods 0.000 claims abstract description 102
- 239000002904 solvent Substances 0.000 claims abstract description 82
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 67
- 150000001875 compounds Chemical class 0.000 claims abstract description 47
- 238000005238 degreasing Methods 0.000 claims abstract description 9
- 238000004140 cleaning Methods 0.000 claims description 63
- 230000008569 process Effects 0.000 claims description 29
- 150000001298 alcohols Chemical class 0.000 claims description 26
- 239000004094 surface-active agent Substances 0.000 claims description 26
- 238000000576 coating method Methods 0.000 claims description 20
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 17
- 238000009835 boiling Methods 0.000 claims description 17
- 238000000151 deposition Methods 0.000 claims description 16
- 239000003444 phase transfer catalyst Substances 0.000 claims description 16
- 230000005291 magnetic effect Effects 0.000 claims description 15
- 239000011248 coating agent Substances 0.000 claims description 14
- 229910052751 metal Inorganic materials 0.000 claims description 14
- 239000002184 metal Substances 0.000 claims description 14
- 239000002585 base Substances 0.000 claims description 13
- 238000001704 evaporation Methods 0.000 claims description 11
- 239000011521 glass Substances 0.000 claims description 11
- 239000000463 material Substances 0.000 claims description 11
- 239000010702 perfluoropolyether Substances 0.000 claims description 11
- RWRIWBAIICGTTQ-UHFFFAOYSA-N difluoromethane Chemical compound FCF RWRIWBAIICGTTQ-UHFFFAOYSA-N 0.000 claims description 10
- 125000004417 unsaturated alkyl group Chemical group 0.000 claims description 10
- XPDWGBQVDMORPB-UHFFFAOYSA-N Fluoroform Chemical compound FC(F)F XPDWGBQVDMORPB-UHFFFAOYSA-N 0.000 claims description 9
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims description 8
- 150000003983 crown ethers Chemical class 0.000 claims description 8
- 150000003839 salts Chemical class 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
- LVGUZGTVOIAKKC-UHFFFAOYSA-N 1,1,1,2-tetrafluoroethane Chemical compound FCC(F)(F)F LVGUZGTVOIAKKC-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
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 239000003380 propellant Substances 0.000 claims description 6
- UJPMYEOUBPIPHQ-UHFFFAOYSA-N 1,1,1-trifluoroethane Chemical compound CC(F)(F)F UJPMYEOUBPIPHQ-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
- 239000007864 aqueous solution Substances 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
- 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 4
- NPNPZTNLOVBDOC-UHFFFAOYSA-N 1,1-difluoroethane Chemical compound CC(F)F NPNPZTNLOVBDOC-UHFFFAOYSA-N 0.000 claims description 4
- FXRLMCRCYDHQFW-UHFFFAOYSA-N 2,3,3,3-tetrafluoropropene Chemical compound FC(=C)C(F)(F)F FXRLMCRCYDHQFW-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
- GTLACDSXYULKMZ-UHFFFAOYSA-N pentafluoroethane Chemical compound FC(F)C(F)(F)F GTLACDSXYULKMZ-UHFFFAOYSA-N 0.000 claims description 4
- 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 claims description 3
- 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 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-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
- 238000012546 transfer 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
- 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 description 2
- 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 description 2
- KHQBFXMPAHZOQA-UHFFFAOYSA-N 1,1,1,2,2,3,4,5,5,6,6,7,7,8,8,9,9,9-octadecafluoronon-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)C(F)(F)F KHQBFXMPAHZOQA-UHFFFAOYSA-N 0.000 claims description 2
- VVMQLAKDFBLCHB-UHFFFAOYSA-N 1,1,1,2,3,4,4,5,5,5-decafluoropent-2-ene Chemical compound FC(F)(F)C(F)=C(F)C(F)(F)C(F)(F)F VVMQLAKDFBLCHB-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
- WXGNWUVNYMJENI-UHFFFAOYSA-N 1,1,2,2-tetrafluoroethane Chemical compound FC(F)C(F)F WXGNWUVNYMJENI-UHFFFAOYSA-N 0.000 claims description 2
- WGZYQOSEVSXDNI-UHFFFAOYSA-N 1,1,2-trifluoroethane Chemical compound FCC(F)F WGZYQOSEVSXDNI-UHFFFAOYSA-N 0.000 claims description 2
- QAERDLQYXMEHEB-UHFFFAOYSA-N 1,1,3,3,3-pentafluoroprop-1-ene Chemical compound FC(F)=CC(F)(F)F QAERDLQYXMEHEB-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
- ODJJZSHROQEZQS-UHFFFAOYSA-N FC(=C(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F)C(F)(F)F Chemical compound FC(=C(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F)C(F)(F)F ODJJZSHROQEZQS-UHFFFAOYSA-N 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
- 238000007598 dipping method Methods 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 238000004528 spin coating Methods 0.000 claims description 2
- 239000013529 heat transfer fluid Substances 0.000 claims 3
- UAFOIVDGAVVKTE-UHFFFAOYSA-N 1,1,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9,9-octadecafluoronon-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)C(F)(F)F UAFOIVDGAVVKTE-UHFFFAOYSA-N 0.000 claims 2
- 239000007791 liquid phase Substances 0.000 claims 2
- 239000012808 vapor phase Substances 0.000 claims 2
- DYBZXEBSLLCTNX-UHFFFAOYSA-N 1,1,1,2,2,3,3,4,5,6,6,7,7,8,8,9,9,9-octadecafluoronon-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)C(F)(F)F DYBZXEBSLLCTNX-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 239000011551 heat transfer agent Substances 0.000 claims 1
- 239000012530 fluid Substances 0.000 abstract description 7
- 239000003795 chemical substances by application Substances 0.000 abstract description 2
- 239000000758 substrate Substances 0.000 description 51
- 239000003921 oil Substances 0.000 description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
- 238000001035 drying Methods 0.000 description 20
- 239000000356 contaminant Substances 0.000 description 17
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
- 239000000243 solution Substances 0.000 description 14
- 239000000314 lubricant Substances 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 12
- 230000008901 benefit Effects 0.000 description 11
- 239000000654 additive Substances 0.000 description 10
- 239000010410 layer Substances 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 230000008021 deposition Effects 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- NBUKAOOFKZFCGD-UHFFFAOYSA-N 2,2,3,3-tetrafluoropropan-1-ol Chemical compound OCC(F)(F)C(F)F NBUKAOOFKZFCGD-UHFFFAOYSA-N 0.000 description 6
- 238000003618 dip coating Methods 0.000 description 6
- 230000008020 evaporation Effects 0.000 description 6
- 238000007654 immersion Methods 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 230000003068 static effect Effects 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 5
- 239000012043 crude product Substances 0.000 description 5
- 230000004907 flux Effects 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 150000002924 oxiranes Chemical class 0.000 description 5
- 230000000996 additive effect Effects 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
- 239000012459 cleaning agent Substances 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 125000006341 heptafluoro n-propyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)* 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- 229920003023 plastic Polymers 0.000 description 4
- 239000004033 plastic Substances 0.000 description 4
- 150000003242 quaternary ammonium salts Chemical group 0.000 description 4
- 239000000377 silicon dioxide Substances 0.000 description 4
- 230000003595 spectral effect Effects 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- BYEAHWXPCBROCE-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-ol Chemical compound FC(F)(F)C(O)C(F)(F)F BYEAHWXPCBROCE-UHFFFAOYSA-N 0.000 description 3
- PSQZJKGXDGNDFP-UHFFFAOYSA-N 2,2,3,3,3-pentafluoropropan-1-ol Chemical compound OCC(F)(F)C(F)(F)F PSQZJKGXDGNDFP-UHFFFAOYSA-N 0.000 description 3
- JUGSKHLZINSXPQ-UHFFFAOYSA-N 2,2,3,3,4,4,5,5-octafluoropentan-1-ol Chemical compound OCC(F)(F)C(F)(F)C(F)(F)C(F)F JUGSKHLZINSXPQ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 241000283973 Oryctolagus cuniculus Species 0.000 description 3
- 229910019142 PO4 Inorganic materials 0.000 description 3
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical class CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 3
- 239000002202 Polyethylene glycol Substances 0.000 description 3
- RHQDFWAXVIIEBN-UHFFFAOYSA-N Trifluoroethanol Chemical compound OCC(F)(F)F RHQDFWAXVIIEBN-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 210000005069 ears Anatomy 0.000 description 3
- 239000004744 fabric Substances 0.000 description 3
- 150000002334 glycols Chemical class 0.000 description 3
- XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 235000021317 phosphate Nutrition 0.000 description 3
- 229920002120 photoresistant polymer Polymers 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- OSQBSECFUJLQFC-NSCUHMNNSA-N (e)-1,1,1,3,4,4,5,5,6,6,7,7,8,8,8-pentadecafluoro-2-(2,2,3,3-tetrafluoropropoxy)oct-2-ene Chemical compound FC(F)C(F)(F)CO\C(C(F)(F)F)=C(\F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F OSQBSECFUJLQFC-NSCUHMNNSA-N 0.000 description 2
- OSQBSECFUJLQFC-IHWYPQMZSA-N (z)-1,1,1,3,4,4,5,5,6,6,7,7,8,8,8-pentadecafluoro-2-(2,2,3,3-tetrafluoropropoxy)oct-2-ene Chemical compound FC(F)C(F)(F)CO\C(C(F)(F)F)=C(/F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F OSQBSECFUJLQFC-IHWYPQMZSA-N 0.000 description 2
- XJSRKJAHJGCPGC-UHFFFAOYSA-N 1,1,1,2,2,3,3,4,4,5,5,6,6-tridecafluorohexane Chemical class FC(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F XJSRKJAHJGCPGC-UHFFFAOYSA-N 0.000 description 2
- PVRSBNQWGXFJEA-UHFFFAOYSA-N 1,1,1,2,2,3,3,4,4,5,5,6,8,8,8-pentadecafluoro-7-(2,2,3,3-tetrafluoropropoxy)octane Chemical compound FC(C(C(C(C(C(C(C(F)(F)F)OCC(C(F)F)(F)F)F)(F)F)(F)F)(F)F)(F)F)(F)F PVRSBNQWGXFJEA-UHFFFAOYSA-N 0.000 description 2
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical class CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 2
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical class CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 2
- XQQZRZQVBFHBHL-UHFFFAOYSA-N 12-crown-4 Chemical compound C1COCCOCCOCCO1 XQQZRZQVBFHBHL-UHFFFAOYSA-N 0.000 description 2
- 238000004293 19F NMR spectroscopy Methods 0.000 description 2
- AUFVJZSDSXXFOI-UHFFFAOYSA-N 2.2.2-cryptand Chemical compound C1COCCOCCN2CCOCCOCCN1CCOCCOCC2 AUFVJZSDSXXFOI-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 229920001774 Perfluoroether Polymers 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 239000000919 ceramic Substances 0.000 description 2
- 239000006184 cosolvent Substances 0.000 description 2
- 238000001514 detection method Methods 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
- 238000006073 displacement reaction Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 239000010408 film Substances 0.000 description 2
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 2
- 150000008282 halocarbons Chemical class 0.000 description 2
- HMSWAIKSFDFLKN-UHFFFAOYSA-N hexacosane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCC HMSWAIKSFDFLKN-UHFFFAOYSA-N 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 238000005304 joining Methods 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 238000010907 mechanical stirring Methods 0.000 description 2
- 229910001092 metal group alloy Inorganic materials 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- UQDUPQYQJKYHQI-UHFFFAOYSA-N methyl laurate Chemical compound CCCCCCCCCCCC(=O)OC UQDUPQYQJKYHQI-UHFFFAOYSA-N 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 2
- 239000010701 perfluoropolyalkylether Substances 0.000 description 2
- 150000004714 phosphonium salts Chemical group 0.000 description 2
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- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 1
- IBWGNZVCJVLSHB-UHFFFAOYSA-M tetrabutylphosphanium;chloride Chemical compound [Cl-].CCCC[P+](CCCC)(CCCC)CCCC IBWGNZVCJVLSHB-UHFFFAOYSA-M 0.000 description 1
- DDFYFBUWEBINLX-UHFFFAOYSA-M tetramethylammonium bromide Chemical compound [Br-].C[N+](C)(C)C DDFYFBUWEBINLX-UHFFFAOYSA-M 0.000 description 1
- NRZGVGVFPHPXEO-UHFFFAOYSA-M tetraphenylarsanium;chloride Chemical compound [Cl-].C1=CC=CC=C1[As+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 NRZGVGVFPHPXEO-UHFFFAOYSA-M 0.000 description 1
- 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
- 239000010409 thin film Substances 0.000 description 1
- KFUSEUYYWQURPO-OWOJBTEDSA-N trans-1,2-dichloroethene Chemical group Cl\C=C\Cl KFUSEUYYWQURPO-OWOJBTEDSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- ADZJWYULTMTLQZ-UHFFFAOYSA-N tritylphosphane;hydrobromide Chemical compound [Br-].C=1C=CC=CC=1C(C=1C=CC=CC=1)([PH3+])C1=CC=CC=C1 ADZJWYULTMTLQZ-UHFFFAOYSA-N 0.000 description 1
- PPQRADLPLZYEKN-UHFFFAOYSA-N tritylphosphanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1C(C=1C=CC=CC=1)([PH3+])C1=CC=CC=C1 PPQRADLPLZYEKN-UHFFFAOYSA-N 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 125000002348 vinylic group Chemical group 0.000 description 1
- 235000012431 wafers Nutrition 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
Classifications
-
- 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
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/43—Solvents
-
- G—PHYSICS
- G11—INFORMATION STORAGE
- G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
- G11B5/00—Recording by magnetisation or demagnetisation of a record carrier; Reproducing by magnetic means; Record carriers therefor
- G11B5/62—Record carriers characterised by the selection of the material
- G11B5/72—Protective coatings, e.g. anti-static or antifriction
- G11B5/725—Protective coatings, e.g. anti-static or antifriction containing a lubricant, e.g. organic compounds
- G11B5/7253—Fluorocarbon lubricant
- G11B5/7257—Perfluoropolyether lubricant
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/05—Preparation of ethers by addition of compounds to unsaturated compounds
- C07C41/06—Preparation of ethers by addition of compounds to unsaturated compounds by addition of organic compounds only
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K3/00—Materials not provided for elsewhere
- C09K3/30—Materials not provided for elsewhere for aerosols
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K5/00—Heat-transfer, heat-exchange or heat-storage materials, e.g. refrigerants; Materials for the production of heat or cold by chemical reactions other than by combustion
- C09K5/02—Materials undergoing a change of physical state when used
- C09K5/04—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K5/00—Heat-transfer, heat-exchange or heat-storage materials, e.g. refrigerants; Materials for the production of heat or cold by chemical reactions other than by combustion
- C09K5/08—Materials not undergoing a change of physical state when used
- C09K5/10—Liquid materials
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
- C10M105/50—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing halogen
- C10M105/54—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing halogen containing carbon, hydrogen, halogen and oxygen
-
- 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
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/24—Organic compounds containing halogen
- C11D3/245—Organic compounds containing halogen containing fluorine
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
- C23G—CLEANING OR DE-GREASING OF METALLIC MATERIAL BY CHEMICAL METHODS OTHER THAN ELECTROLYSIS
- C23G5/00—Cleaning or de-greasing metallic material by other methods; Apparatus for cleaning or de-greasing metallic material with organic solvents
- C23G5/02—Cleaning or de-greasing metallic material by other methods; Apparatus for cleaning or de-greasing metallic material with organic solvents using organic solvents
- C23G5/028—Cleaning or de-greasing metallic material by other methods; Apparatus for cleaning or de-greasing metallic material with organic solvents using organic solvents containing halogenated hydrocarbons
- C23G5/02854—Cleaning or de-greasing metallic material by other methods; Apparatus for cleaning or de-greasing metallic material with organic solvents using organic solvents containing halogenated hydrocarbons characterised by the stabilising or corrosion inhibiting additives
- C23G5/02861—Oxygen-containing compounds
- C23G5/02877—Ethers
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2213/00—Organic macromolecular compounds containing halogen as ingredients in lubricant compositions
- C10M2213/06—Perfluoro polymers
- C10M2213/0606—Perfluoro polymers used as base material
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/14—Electric or magnetic purposes
- C10N2040/18—Electric or magnetic purposes in connection with recordings on magnetic tape or disc
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2050/00—Form in which the lubricant is applied to the material being lubricated
- C10N2050/015—Dispersions of solid lubricants
- C10N2050/02—Dispersions of solid lubricants dissolved or suspended in a carrier which subsequently evaporates to leave a lubricant coating
-
- C11D2111/16—
-
- C11D2111/22—
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
- H05K3/00—Apparatus or processes for manufacturing printed circuits
- H05K3/22—Secondary treatment of printed circuits
- H05K3/26—Cleaning or polishing of the conductive pattern
Definitions
- This invention relates to cleaning compositions comprising unsaturated fluorocarbon ethers.
- the invention further relates to use of said cleaning compositions in methods to clean, degrease, deflux, dewater, and deposit fluorolubricant.
- the invention further relates to novel unsaturated fluorocarbon ethers and their use as cleaning compositions and in the methods listed above.
- Chlorofluorocarbon (CFC) compounds have been used extensively in the area of semiconductor manufacture to clean surfaces such as magnetic disk media. However, chlorine-containing compounds such as CFC compounds are considered to be detrimental to the Earth's ozone layer. In addition, many of the hydrofluorocarbons used to replace CFC compounds have been found to contribute to global warming. Therefore, there is a need to identify new environmentally safe solvents for cleaning applications, such as removing residual flux, lubricant or oil contaminants, and particles. There is also a need for identification of new solvents for deposition of fluorolubricants and for drying or dewatering of substrates that have been processed in aqueous solutions.
- the present invention provides new compositions comprising unsaturated fluorocarbon ethers, and methods of manufacture of such unsaturated fluorocarbon ethers. These compositions have utility in many of the applications formerly served by CFC compounds.
- the compositions of the present invention possess some or all of the desired properties of little or no environmental impact, ability to dissolve oils, greases or lubricants (in particular fluorine-containing lubricants), non-flammability, and ability to dissolve surfactant compounds used in methods for drying or dewatering.
- compositions in another embodiment, disclosed here are compositions
- compositions comprising a compound having the formula
- compositions comprising a compound having the formula
- novel methods of manufacturing fluorocarbon ethers including those above.
- CF 3 (CF2)xC(OR) CFCF2(CF2)yCF 3
- CF 3 CF CFCF(OR)(CF2)x(CF2)yCF 3
- CF 3 (CF 2 )xCF C(OR)CF 2 (CF 2 ) y CF 3
- R is 2,2,3,3-tetrafluoro-1 -propyl, 2,2,3,3,3-pentafluoro-1 -propyl, 2,2,2-trifluoro-1 -ethyl, 2,2,3,3,4,4,5,5-octafluoro-1 -pentyl, or 1 ,1 ,1 ,3,3,3- hexafluoro-2-propyl , .
- CF 3 CF CFCF2(CF2)x(CF2)yCF 3
- the fluorinated alcohol is 2,2,3,3-tetrafluoro-1 - propanol, 2,2,3,3,3-pentafluoro-1 -propanol, 2,2,2-trifluoroethanol,
- compositions disclosed above wherein said unsaturated fluoroalkyl perfluoroalkene ether comprises a compound having the formula
- compositions further comprise a compound having the formula
- composition comprising at least one unsaturated fluoroalkyl perfluoroalkene ether selected from the group consisting of
- CF 3 (CF 2 )xCF CFCF(OR)(CF 2 ) y CF 3
- CF 3 (CF 2 )xC(OR) CFCF 2 (CF 2 ) y CF 3
- CF 3 CF CFCF(OR)(CF 2 )x(CF 2 ) y CF 3
- CF 3 (CF 2 )xCF C(OR)CF 2 (CF 2 ) y CF 3
- phase transfer catalyst is a substance that facilitates the transfer of ionic compounds (e.g., reactants or components) into an organic phase.
- the phase transfer catalyst facilitates the reaction of these dissimilar and incompatible components. While various phase transfer catalysts may function in different ways, their mechanism of action is not determinative of their utility in the present process.
- unsaturated fluoroethers which have utility as novel solvents, carrier fluids, dewatering agents, degreasing solvents or defluxing solvents.
- CF 3 (CF2)xC(OR) CFCF2(CF2)yCF 3
- CF 3 CF CFCF(OR)(CF2)x(CF 2 )yCF 3
- CF 3 (CF 2 )xCF C(OR)CF 2 (CF 2 ) y CF 3
- R is 2,2,3,3-tetrafluoro-1 -propyl, 2,2,3,3,3-pentafluoro-1 -propyl, 2,2,2-trifluoro-1 -ethyl, 2,2,3,3,4,4,5,5-octafluoro-1 -pentyl, or 1 ,1 ,1 ,3,3,3- hexafluoro-2-propyl.
- compositions disclosed herein may be prepared by contacting at least one perfluoroalkene, such as perfluoro-3-heptene, pefluoro-2-heptene, perfluoro-2-hexene, perfluoro-
- the fluorinated alcohol is defined by the formula R-OH, wherein R is 2,2,3,3- tetrafluoro-1 -propyl, 2,2,3,3,3-pentafluoro-1 -propyl, 2,2,2-trifluoro-1 -ethyl, 2,2,3,3,4,4,5,5-octafluoro-1 -pentyl, or 1 ,1 ,1 ,3,3,3-hexafluoro-2-propyl .
- perfluoro-3-heptene may be reacted with at least one fluorinated alcohol in presence of a strong base.
- Such fluorinated alcohols include 2,2,3,3-tetrafluoro-1 -propanol, 2,2,3,3,3-pentafluoro-1 -propanol, 2,2,2- trifluoroethanol, 2,2,3,3,4,4,5,5-octafluoro-1 -pentanol, or 1 ,1 ,1 ,3,3,3- hexafluoro-2-propanol, or any mixture thereof.
- the strong base is a base which will react with a fluorinated alcohol to produce an alkoxide upon combination of the base with said fluorinated alcohol.
- Bases which can be used to form such alkoxides include alkali metal hydroxides, such as sodium hydroxide or potassium hydroxide without limitation.
- the strong base is present in the form of an aqueous solution having a concentration of alkali metal hydroxide of from 10% by weight to 45% by weight.
- one mole of alkali metal hydroxide is used per mole of fluorinated alcohol to produce the alkoxide.
- 1 .1 moles of alkali metal hydroxide per mole of fluorinated alcohol is used.
- about 0.9 moles of alkali metal hydroxide per mole of fluorinated alcohol is used.
- one mole of alkali metal hydroxide is used per mole of perfluoroalkene. In another embodiment, about 1 .1 moles of alkali metal hydroxide are used per mole of perfluoroalkene. In yet another embodiment, about 1 .05 moles of alkali metal hydroxide are used per mole of perfluoroalkene.
- the alkali metal hydroxide is combined with the perfluoroalkene, and then a fluorinated alcohol and water are added to the mixture of perfluoroalkene and base, resulting in an immediate exothermic reaction.
- the alkali metal hydroxide is dissolved in water and mixed with the perfluoroalkene. Addition of the fluorinated alcohol results in an immediate exothermic reaction to produce the unsaturated alkyl perfluoroalkene ethers.
- the fluorinated alcohol is added to the perfluoroalkene, alkali metal hydroxide and water in one portion. In another embodiment, the fluorinated alcohol is added slowly over a period of time. In one embodiment, the fluorinated alcohol is added over one hour. In another embodiment, the fluorinated alcohol is added over two hours. In yet another embodiment, the perfluoroalkene, alkali metal hydroxide and fluorinated alcohol are added together, and the water is added slowly over time.
- the perfluoroalkene, alkali metal hydroxide, fluorinated alcohol and water are all added at about room temperature.
- the perfluoroalkene and aqueous solution of alkali metal hydroxide are heated to about 50°C, and the fluorinated alcohol is added slowly over a period of time.
- a phase transfer catalyst is added to the mixture of perfluoroalkene, alkali metal hydroxide, fluorinated alcohol and water.
- a phase transfer catalyst is a quaternary ammonium salt.
- a phase transfer catalyst is
- the amount of phase transfer catalyst is from about 1 % by weight to about 10% by weight of the alkali metal hydroxide.
- the phase transfer catalyst can be ionic or neutral and is selected from the group consisting of crown ethers, onium salts, cryptates and polyalkylene glycols and derivatives thereof, and mixtures thereof.
- An effective amount of the phase transfer catalyst should be used in order to effect the desired reaction; such an amount can be determined by limited experimentation once the reactants, process conditions and phase transfer catalyst are selected.
- Crown ethers are cyclic molecules in which ether groups are connected by dimethylene linkages; the compounds form a molecular structure that is believed to be capable of "receiving” or holding the alkali metal ion of the hydroxide and to thereby facilitate the reaction.
- crown ethers include 18-crown-6, especially in combination with potassium hydroxide; 15-crown-5, especially in combination with sodium hydroxide; 12-crown-4, especially in combination with lithium hydroxide.
- Derivatives of the above crown ethers are also useful, e.g., dibenzo-18-crown-6, dicyclohexano-18-crown-6, and dibenzo- 24-crown-8 as well as 12-crown-4.
- Other polyethers particularly useful for alkali metal compounds, and especially for lithium are described in U.S. Pat. No. 4,560,759 which is incorporated herein by reference to the extent permitted.
- crown ethers compounds which differ by the replacement of one or more of the oxygen atoms by other kinds of donor atoms, particularly N or S, such as hexamethyl-[14]-4,1 1 -dieneN 4 .
- Onium salts include quaternary phosphonium salts and quaternary ammonium salts that may be used as the phase transfer catalyst in the process of the present invention; such compounds can be represented by the following formulas I and II:
- each of Ri , F3 ⁇ 4, R3 and R 4 which may be the same or different, is an alkyl group, an aryl group or an aralkyl group, and X' is a halogen atom.
- R3 and R 4 which may be the same or different, is an alkyl group, an aryl group or an aralkyl group, and X' is a halogen atom.
- tetramethylammonium chloride tetramethylammonium bromide, benzyltriethylammonium chloride, methyltrioctylammonium chloride (available commercially under the brands Aliquat(R) 336 and Adogen 464), tetra-n-butylammonium chloride, tetra-n-butylammonium bromide, tetra-n-butylammonium hydrogen sulfate, tetra-n-butylphosphonium chloride, tetraphenylphosphonium bromide, tetraphenylphosphonium chloride, triphenylmethylphosphonium bromide and
- triphenylmethylphosphonium chloride triphenylmethylphosphonium chloride.
- benzyltriethylammonium chloride is preferred for use under strongly basic conditions.
- Other useful compounds within this class of compounds include those exhibiting high temperature stabilities (e.g., up to about 200.degree. C.) and including 4-dialkylaminopyridinium salts such as tetraphenylarsonium chloride, bis[tris(dimethylamino)phosphine]iminium chloride and tetratris[tris(dimethylamino)phosphinimino]phosphonium chloride; the latter two compounds are also reported to be stable in the presence of hot, concentrated sodium hydroxide and, therefore, can be particularly useful.
- Polyalkylene glycol compounds useful as phase transfer catalysts can be represented by the formula:
- R 5 is an alkylene group
- each of R 6 and R 7 which may be the same or different, is a hydrogen atom, an alkyl group, an aryl group or, an aralkyi group, and t is an integer of at least 2.
- Such compounds include, for example glycols such as diethylene glycol, triethylene glycol, tetraethylene glycol, pentaethylene glycol, hexaethylene glycol,
- tetrapropylene glycol and tetramethylene glycol and monoalkyl ethers such as monomethyl, monoethyl, monopropyl and monobutyl ethers of such glycols, dialkyi ethers such as tetraethylene glycol dimethyl ether and pentaethylene glycol dimethyl ether, phenyl ethers, benzyl ethers, and polyalkylene glycols such as polyethylene glycol (average molecular weight about 300) dimethyl ether, polyethylene glycol (average molecular weight about 300) dibutyl ether, and polyethylene glycol (average molecular weight about 400) dimethyl ether.
- R 6 and R 7 are alkyl groups, aryl groups or aralkyi groups are preferred.
- Cryptates are another class of compounds useful in the present as phase transfer catalysts. These are three-dimensional polymacrocyclic chelating agents that are formed by joining bridgehead structures with chains that contain properly spaced donor atoms. For example, bicyclic molecules that result from joining nitrogen bridgeheads with chains of (- OCH2CH2-) groups as in 2.2.2-cryptate (4,7,13,16,21 ,24-hexaoxa-1 , 10- diasabicyclo-(8.8.8)hexacosane; available under the brand names cryptand 222 and Kryptofix 222).
- the donor atoms of the bridges may all be O, N, or S, or the compounds may be mixed donor macrocycles in which the bridge strands contain combinations of such donor atoms.
- phase transfer catalysts from within one of the groups described above may also be useful as well as combinations or mixtures from more than one group, for example, crown ethers and oniums, or from more than two of the groups, e.g., quaternary
- phosphonium salts and quaternary ammonium salts and crown ethers and polyalkylene glycols.
- the reaction mixture is allowed to cool to ambient temperature and poured into a separatory funnel.
- the lower organic layer comprises unsaturated fluoroalkyl perfluoroalkene ether, and is separated from an aqueous layer containing inorganic salts.
- the organic layer is then dried, and then can be further purified by distillation.
- the organic layer is dried over anhydrous magnesium sulfate.
- the organic layer is dried over anhydrous sodium sulfate.
- a fraction is collected from the distillation predominantly between 108°C and 122°C, depending on whether the methyl or ethyl ethers were prepared, comprising a mixture of allylic and vinylic perfluoroalkene alkyl ethers.
- the present compositions may further comprise a propellant.
- Aerosol propellant may assist in delivering the present composition from a storage container to a surface in the form of an aerosol. Aerosol propellant is optionally included in the present composition in up to about 25 weight percent of the total composition.
- Representative aerosol propellants comprise air, nitrogen, carbon dioxide, difluoromethane (CF 2 H 2 , HFC-32), trifluoromethane (CF 3 H, HFC-23), difluoroethane (CHF 2 CH 3 , HFC-152a), trifluoroethane (CH 3 CF 3 , HFC- 143a; or CHF 2 CH 2 F, HFC-143), tetrafluoroethane (CF 3 CH 2 F, HFC-134a; or CF 2 HCF 2 H, HFC-134), pentafluoroethane (CF 3 CF 2 H, HFC-125), 1 ,3,3,3-tetrafluoro-1 -propene (HFO-1234ze), 2,3,3,3-tetrafluoro-1 -propene (HFO-1234yf), 1 ,2,3,3,3-pentafluoropropene (HFO-1225ye), 1 ,1 ,3,3,3- pentafluor
- the present compositions may further comprise at least one surfactant.
- the surfactants of the present invention include all surfactants known in the art for dewatering or drying of substrates.
- Representative surfactants include alkyl phosphate amine salts (such as a 1 :1 salt of 2-ethylhexyl amine and isooctyl phosphate); ethoxylated alcohols, mercaptans or alkylphenols; quaternary ammonium salts of alkyl phosphates (with fluoroalkyl groups on either the ammonium or phosphate groups); and mono- or di-alkyl phosphates of fluorinated amines. Additional fluorinated surfactant compounds are described in U. S. Patent No. 5,908,822, incorporated herein by reference.
- the amount of surfactant included in the dewatering compositions of the present invention can vary widely depending on the particular drying application in which said composition will be used, but is readily apparent to those skilled in the art.
- the amount of surfactant dissolved in the unsaturated fluorinated ether solvent is not greater than about 1 weight percent, based on the total weight of the surfactant/solvent composition.
- larger amounts of surfactant can be used, if after treatment with the composition, the substrate being dried is thereafter treated with solvent containing either no or minimal surfactant.
- the amount of surfactant is at least about 50 parts per million (ppm, on a weight basis).
- the amount of surfactant is from about 100 to about 5000 ppm.
- the amount of surfactant used is from about 200 to about 2000 ppm based on the total weight of the dewatering composition.
- additives may be included in the present compositions comprising solvents and surfactants for use in dewatering.
- additives include compounds having antistatic properties; the ability to dissipate static charge from non-conductive substrates such as glass and silica.
- Use of an antistatic additive in the dewatering compositions of the present invention may be necessary to prevent spots and stains when drying water or aqueous solutions from electrically non-conductive parts such as glass lenses and mirrors.
- Most unsaturated fluoroether solvents of the present invention also have utility as dielectric fluids, i.e., they are poor conductors of electric current and do not easily dissipate static charge.
- Boiling and general circulation of dewatering compositions in conventional drying and cleaning equipment can create static charge, particularly in the latter stages of the drying process where most of the water has been removed from a substrate.
- static charge collects on non-conductive surfaces of the substrate and prevents the release of water from the surface. The residual water dries in place resulting in undesirable spots and stains on the substrate.
- Static charge remaining on substrates can bring out impurities from the cleaning process or can attract impurities such as lint from the air, which results in unacceptable cleaning performance.
- desirable antistatic additives are polar compounds, which are soluble in the present unsaturated fluorinated ether solvent and result in an increase in the conductivity of the unsaturated fluorinated ether solvent resulting in dissipation of static charge from a substrate.
- the antistatic additives have a normal boiling point near that of the unsaturated fluorinated ether solvent and have minimal to no solubility in water.
- the antistatic additives have a solubility in water of less than about 0.5 weight percent.
- the solubility of antistatic agent is at least 0.5 weight percent in unsaturated fluorinated ether solvent.
- the antistatic additive is nitromethane
- the present dewatering composition containing an antistatic additive is effective in both the dewatering and drying and rinse steps of a method to dewater or dry a substrate as described below.
- HFCs hydrofluorocarbons
- surfactants have been added to dewatering or drying solvents to displace water from substrates.
- composition is to reduce the amount of water on the surface of a substrate being dried.
- the primary function of the surfactant is to displace any remaining water from the surface of the substrate.
- the surfactant for dewatering and drying is soluble to at least 1 weight percent based on the total solvent/surfactant composition weight.
- the dewatering or drying method of the present disclosure is very effective in displacing water from a broad range of substrates including metals, such as tungsten, copper, gold, beryllium, stainless steel, aluminum alloys, brass and the like; from glasses and ceramic surfaces, such as glass, sapphire, borosilicate glass, alumina, silica such as silicon wafers used in electronic circuits, fired alumina and the like; and from plastics such as polyolefin (“Alathon”, Rynite®, "Tenite”), polyvinylchloride, polystyrene (Styron), polytetrafluoroethylene (Teflon®), tetrafluoroethylene-ethylene copolymers (Tefzel®), polyvinylidenefluoride (“Kynar”), ionomers (Surlyn®), acrylonitrile-butadiene-styrene polymers (Kralac®), phenol-formaldeh
- compositions for use in the present dewatering or drying method are compatible with elastomers.
- the disclosure is directed to a process for removing at least a portion of water from, i.e., dewatering, the surface of a wetted substrate, which comprises contacting the substrate with the aforementioned dewatering composition, and then removing the substrate from contact with the dewatering composition.
- water originally bound to the surface of the substrate is displaced by solvent and/or surfactant and leaves with the dewatering composition.
- at least a portion of water is meant at least about 75 weight percent of water at the surface of a substrate is removed per immersion cycle.
- immersion cycle is meant one cycle involving at least a step wherein substrate is immersed in the present dewatering composition.
- minimal amounts of surfactant remaining adhered to the substrate can be further removed by contacting the substrate with surfactant-free halocarbon solvent. Holding the article in the solvent vapor or refluxing solvent will further decrease the presence of surfactant remaining on the substrate. Removal of solvent adhering to the surface of the substrate is effected by evaporation. Evaporation of solvent at atmospheric or subatmospheric pressures can be employed and temperatures above and below the boiling point of the halocarbon solvent can be used.
- Methods of contacting the substrate with dewatering composition are not critical and can vary widely.
- the substrate can be immersed in the composition, or the substrate can be sprayed with the composition using conventional equipment.
- Complete immersion of the substrate is preferred as it generally insures contact between the composition and all exposed surfaces of the substrate.
- any other method, which can easily provide such complete contact may be used.
- the time period over which substrate and dewatering composition are contacted can vary widely. Usually, the contacting time is up to about 5 minutes, however, longer times may be used if desired. In one embodiment of the dewatering process, the contacting time is from about 1 second to about 5 minutes. In another embodiment, the contacting time of the dewatering process is from about 15 seconds to about 4 minutes.
- Contacting temperatures can also vary widely depending on the boiling point of the composition. In general, the contacting temperature is equal to or less than the composition's normal boiling point.
- compositions of the present disclosure may further contain a co-solvent.
- co-solvents are desirable where the present compositions are employed in cleaning conventional process residue from substrates, e.g., removing soldering fluxes and degreasing mechanical components comprising substrates of the present invention.
- co-solvents include alcohols (such as methanol, ethanol,
- isopropanol ethers (such as diethyl ether, methyl tertiary-butyl ether), ketones (such as acetone), esters (such as ethyl acetate, methyl dodecanoate, isopropyl myristate and the dimethyl or diisobutyl esters of succinic, glutaric or adipic acids or mixtures thereof), ether alcohols (such as propylene glycol monopropyl ether, dipropylene glycol monobutyl ether, and tripropylene glycol monomethyl ether), and hydrocarbons (such as pentane, cyclopentane, hexane, cyclohexane, heptane, octane), and hydrochlorocarbons (such as trans-1 ,2-dichloroethylene).
- ethers such as diethyl ether, methyl tertiary-butyl ether
- ketones such as acetone
- compositions may be lost during operation through leaks in shaft seals, hose connections, soldered joints and broken lines.
- the working composition may be released to the atmosphere during maintenance procedures on equipment. If the composition is not a pure component, the composition may change when leaked or discharged to the atmosphere from the equipment, which may cause the composition remaining in the equipment to exhibit unacceptable performance.
- the unsaturated fluoroalkyl perfluoroalkene ethers described here further comprise an epoxide as an acid acceptor.
- the concentration of such epoxides may range from at least 0.001 weight percent to not more than 1 .0 weight percent. In another embodiment, the concentration is from 0.02 weight percent to not more than 0.5 weight percent. In yet another embodiment, the be used at a concentration of not more than 0.2 weight percent of the total composition. The amount of epoxide may range between any combination of these values, inclusive of the recited values.
- Suitable epoxides include aliphatic and aromatic epoxides including those selected from epichlorohydrin, 2-hexene epoxide, 3-hexene epoxide, glycidol, propylene oxide, cis-2,3-pentene oxide, 2-methyl-2,3-epoxybutane, 1 ,2-epoxycyclopentene, 2, 3-d i methyl - 2,3-epoxybutane, 1 ,2-epoxycyclohexane, 1 ,2-butylene oxide and 2,3- butylene oxide.
- the epoxide is a saturate mono- epoxide containing from 3 to 8 carbon atoms.
- composition comprising at least one unsaturated fluoroalkyl perfluoroalkene ether having a formula selected from the group consisting of
- CF 3 CF CFCF(OR)(CF2)x(CF 2 )yCF3,
- compositions of the present disclosure are useful as cleaning compositions, cleaning agents, deposition solvents and as dewatering or drying solvents.
- cleaning compositions for proper operation in use, cleaning agents, deposition solvents and as dewatering or drying solvents.
- the present disclosure relates to a process for removing residue from a surface or substrate comprising contacting the surface or substrate with a cleaning composition or cleaning agent of the present invention and, optionally, recovering the surface or substrate substantially free of residue from the cleaning composition or cleaning agent.
- the present disclosure relates to a method for cleaning surfaces by removing contaminants from the surface.
- the method for removing contaminants from a surface comprises contacting the surface having contaminants with a cleaning composition of the present invention to solubilize the contaminants and, optionally, recovering the surface from the cleaning composition. The surface is then substantially free of contaminants.
- the contaminants or residues that may be removed by the present method include, but are not limited to oils and greases, flux residues, and particulate contaminants.
- the contacting may be accomplished by spraying, flushing, wiping with a substrate e.g., wiping cloth or paper, that has the cleaning composition incorporated in or on it.
- the contacting may be accomplished by spraying, flushing, wiping with a substrate e.g., wiping cloth or paper, that has the cleaning composition incorporated in or on it.
- the contacting may be accomplished by spraying, flushing, wiping with a substrate e.g., wiping cloth or paper, that has the cleaning composition incorporated in or on it.
- the contacting may be accomplished by spraying, flushing, wiping with a substrate e.g., wiping cloth or paper, that has the cleaning composition incorporated in or on it.
- the contacting may be accomplished by spraying, flushing, wiping with a substrate e.g., wiping cloth or paper, that has the cleaning composition incorporated in or on it.
- the contacting may be accomplished by spraying, flushing, wiping with a substrate e.g., wiping cloth or
- the recovering is by removing the surface that has been contacted from the cleaning composition bath (in a similar manner as described for the method for depositing an a fluorolubricant on a surface as described below). In another embodiment of the method, the recovering is by allowing the cleaning composition that has been sprayed, flushed, or wiped on the disk to drain away.
- any residual cleaning composition that may be left behind after the completion of the previous steps may be evaporated in a manner similar to that for the deposition method as well.
- the method for cleaning a surface may be applied to the same types of surfaces as the method for deposition as described below.
- Semiconductor surfaces or magnetic media disks of silica, glass, metal or metal oxide, or carbon may have contaminants removed by the method.
- contaminant may be removed from a disk by contacting the disk with the cleaning composition and recovering the disk from the cleaning composition.
- the present method also provides methods of removing contaminants from a product, part, component, substrate, or any other article or portion thereof by contacting the article with a cleaning composition of the present invention.
- article is used herein to refer to all such products, parts, components, substrates, and the like and is further intended to refer to any surface or portion thereof.
- contaminant is intended to refer to any unwanted material or substance present on the article, even if such substance is placed on the article intentionally.
- contaminant as used herein is intended to cover and encompass such a photo resist material. Hydrocarbon based oils and greases and dioctylphthalate are examples of the contaminants that may be found on the carbon coated disks.
- the present method comprises contacting the article with a cleaning composition of the invention, in a vapor degreasing and solvent cleaning method.
- vapor degreasing and solvent cleaning methods consist of exposing an article, preferably at room temperature, to the vapors of a boiling cleaning composition. Vapors condensing on the object have the advantage of providing a relatively clean, distilled cleaning composition to wash away grease or other contamination. Such processes thus have an additional advantage in that final evaporation of the present cleaning composition from the object leaves behind relatively little residue as compared to the case where the object is simply washed in liquid cleaning composition.
- the present methods involve raising the temperature of the cleaning composition above ambient or to any other temperature that is effective in such application to substantially improve the cleaning action of the cleaning composition.
- such processes are also generally used for large volume assembly line operations where the cleaning of the article, particularly metal parts and assemblies, must be done efficiently and quickly.
- the cleaning methods of the present invention comprise immersing the article to be cleaned in liquid cleaning
- the cleaning methods of the present invention comprise immersing the article to be cleaned in liquid cleaning composition at about the boiling point of the cleaning composition. In one such embodiment, this step removes a substantial amount of the target contaminant from the article. In yet another embodiment, this step removes a major portion of the target contaminant from the article. In one embodiment, this step is then followed by immersing the article in freshly distilled cleaning composition, which is at a temperature below the temperature of the liquid cleaning composition in the preceding immersion step.
- the method also includes the step of then contacting the article with relatively hot vapor of the cleaning composition, by exposing the article to vapors rising from the hot/boiling cleaning composition associated with the first mentioned immersion step. In one such embodiment, this results in condensation of the cleaning composition vapor on the article.
- the article may be sprayed with distilled cleaning composition before final rinsing. It is contemplated that numerous varieties and types of vapor degreasing equipment are adaptable for use in connection with the present methods. One example of such equipment and its operation is disclosed by U.S. Patent No. 3,085,918, which is incorporated herein by reference. The equipment disclosed therein includes a boiling sump for containing a cleaning composition, a clean sump for containing distilled cleaning composition, a water separator, and other ancillary equipment.
- the present cleaning methods may also comprise cold cleaning in which the contaminated article is either immersed in the fluid cleaning composition of the present invention under ambient or room temperature conditions or wiped under such conditions with rags or similar objects soaked in the cleaning composition.
- the most advanced, highest recording densities and lowest cost method of storing digital information involves writing and reading magnetic flux patterns from rotating disks coated with magnetic materials.
- a magnetic layer where information is stored in the form of bits, is sputtered onto a metallic support structure.
- an overcoat usually a carbon- based material, is placed on top of the magnetic layer for protection and finally a lubricant is applied to the overcoat.
- a read-write head flies above the lubricant and the information is exchanged between the head and the magnetic layer.
- hard drive manufacturers have reduced the distance between the head and the magnetic layer, or fly-height, to less than 100 Angstroms.
- the head and the disk surface will make contact.
- it To reduce wear on the disk, from both sliding and flying contacts, it must be lubricated.
- Fluorolubricants are widely used as lubricants in the magnetic disk drive industry to decrease the friction between the head and disk, that is, reduce the wear and therefore minimize the possibility of disk failure.
- the fluorolubricants of the present disclosure comprise perfluoropolyether (PFPE) compounds, or lubricant comprising X-1 P®, which is a phosphazene-containing disk lubricant.
- PFPE perfluoropolyether
- X-1 P® a phosphazene-containing disk lubricant
- PFAE perfluoroalkylethers
- PFPAE perfluoropolyalkylethers
- fluorolubricants for the present inventive method include but are not limited to Krytox® GLP 100, GLP 105 or GLP 160 (E. I. du Pont de Nemours & Co., Fluoroproducts, Wilmington, DE, 19898, USA); Fomblin® Z-Dol 2000, 2500 or 4000, Z-Tetraol, or Fomblin® AM 2001 or AM 3001 (sold by Solvay Solexis S.p.A., Milan, Italy); DemnumTM LR-200 or S-65 (offered by Daikin America, Inc., Osaka, Japan); X-1 P® (a partially fluorinated hyxaphenoxy cyclotriphosphazene disk lubricant available from Quixtor Technologies Corporation, a subsidiary of Dow Chemical Co, Midland, Ml); and mixtures thereof.
- the Krytox® lubricants are not limited to Krytox® GLP 100, GLP 105 or GLP 160 (E. I. du Pont de Nemours
- perfluoroalkylpolyethers having the general structure F(CF(CF 3 )CF 2 O) n - CF2CF3 , wherein n ranges from 10 to 60.
- the Fomblin® lubricants are functionalized perfluoropolyethers that range in molecular weight from 500 to 4000 atomic mass units and have general formula X-CF 2 -O(CF 2 -CF 2 - O) p -(CF 2 O) q -CF 2 -X, wherein X may be -CH 2 OH, CH 2 (O-CH 2 -CH 2 ) n OH, CH 2 OCH 2 CH(OH)CH 2 OH or -CH 2 O-CH 2 -piperonyl.
- the DemnumTM oils are perfluoropolyether-based oils ranging in molecular weight from 2700 to 8400 atomic mass units. Additionally, new lubricants are being developed such as those from Moresco (Thailand) Co., Ltd, which may be useful in the present inventive method.
- the fluorolubricants of the present invention may additionally comprise additives to improve the properties of the fluorolubricant.
- X-1 P® which may serve as the lubricant itself, is often added to other lower cost fluorolubricants in order to increase the durability of disk drives by passivating Lewis acid sites on the disk surface responsible for PFPE degradation.
- the fluorolubricants of the present invention may further comprise Z-DPA (Hitachi Global Storage Technologies, San Jose, CA), a PFPE terminated with dialkylamine end-groups.
- Z-DPA Haitachi Global Storage Technologies, San Jose, CA
- the nucleophilic end-groups serve the same purpose as X1 P®, thus providing the same stability without any additive.
- the surface on which the fluorolubricant may be deposited is any solid surface that may benefit from lubrication.
- Semiconductor materials such as silica disks, metal or metal oxide surfaces, vapor deposited carbon surfaces or glass surfaces are representative of the types of surfaces for which the methods of the present invention are useful.
- the present inventive method is particularly useful in coating magnetic media such as computer drive hard disks.
- the surface may be a glass, or aluminum substrate with layers of magnetic media that is also coated by vapor deposition with a thin (10-50 Angstrom) layer of amorphous hydrogenated or nitrogenated carbon.
- fluorolubricant may be deposited on the surface disk indirectly by applying the fluorolubricant to the carbon layer of the disk.
- the first step of combining the fluorolubricant and solvent may be accomplished in any suitable manner such as mixing in a suitable container such as a beaker or other container that may be used as a bath for the deposition method.
- the fluorolubricant concentration in the unsaturated fluorinated ether solvent may be from about 0.010 percent (wt/wt) to about 0.50 percent (wt/wt).
- the step of contacting said combination of fluorolubricant and solvent with the surface may be accomplished in any manner appropriate for said surface (considering the size and shape of the surface).
- a hard drive disk must be supported in some manner such as with a mandrel or some other support that may fit through the hole in the center of the disk. The disk will thus be held vertically such that the plane of the disk is perpendicular to the solvent bath.
- the mandrel may have different shapes including but not limited to, a cylindrical bar, or a V-shaped bar. The mandrel shape will determine the area of contact with the disk.
- the mandrel may be constructed of any material strong enough to hold the disk, including but not limited to metal, metal alloy, plastic or glass.
- a disk may be supported vertically upright in a woven basket or be clamped into a vertical position with 1 or more clamps on the outer edge.
- the support may be constructed of any material with the strength to hold the disk, such as metal, metal alloy, plastic or glass. However the disk is supported, the disk will be lowered into a container holding a bath of the fluorolubricant/solvent combination. The bath may be held at room temperature or be heated or cooled to temperatures ranging from about 0°C to about 50°C.
- the disk may be supported as described above and the bath may be raised to immerse the disk. In either case, the disk may then be removed from the bath (either by lowering the bath or by raising the disk). Excess fluorolubricant/solvent combination can be drained into the bath. Either of the methods for contacting the fluorolubricant solvent combination with the disk surface of either lowering the disk into a bath or raising a bath to immerse the disk are commonly referred to as dip coating. Other methods for contacting the disk with the
- fluorolubricant/solvent combination may be used in the present inventive method, including spraying or spin coating.
- the disk When the disk is removed from the bath, the disk will have a coating of fluorolubricant and some residual solvent (unsaturated fluorinated ether) on its surface.
- the residual solvent may be evaporated. Evaporation is usually performed at room temperature. However, other temperatures both above and below room temperature may be used as well for the evaporation step. Temperatures ranging from about 0 °C to about 100 °C may be used for evaporation.
- the surface, or the disk if the surface is a disk, after completion of the coating method, will be left with a substantially uniform or uniform coating of fluorolubricant that is substantially free of solvent.
- the fluorolubricant may be applied to a thickness of less than about 300 nm, and alternately to a thickness of about 100 to about 300 nm.
- a uniform fluorolubricant coating is desired for proper functioning of a disk and so areas of varying fluorolubricant thickness are undesirable on the surface of the disk.
- the read/write head must get closer and closer to the disk in order to function properly. If irregularities due to variation in coating thickness are present on the surface of the disk, the probability of contact of the head with these areas on the disk is much greater. While there is a desire to have enough fluorolubricant on the disk to flow into areas where it may be removed by head contact or other means, coating that is too thick may cause "smear," a problem associated with the read/write head picking up excess fluorolubricant.
- the terms “comprises,” “comprising,” “includes,” “including,” “has,” “having” or any other variation thereof, are intended to cover a non-exclusive inclusion.
- a process, method, article, or apparatus that comprises a list of elements is not necessarily limited to only those elements but may include other elements not expressly listed or inherent to such process, method, article, or apparatus.
- “or” refers to an inclusive or and not to an exclusive or. For example, a condition A or B is satisfied by any one of the following: A is true (or present) and B is false (or not present), A is false (or not present) and B is true (or present), and both A and B are true (or present).
- Example 1 demonstrates the reaction of 2,2,3,3-tetrafluoropropanol with perfluorooct-2-ene.
- a 1 -L, 3-neck round-bottom (RB) flask was set up with overhead mechanical stirring, heating mantle, reflux condenser, Claisen adapter with thermocouple and a 250-mL pressure-equalizing addition funnel.
- F-2-octene Perfluorooct-2-ene
- MS mass spectral
- the crude product was decanted in a separatory funnel, dried over magnesium sulfate, and filtered through polypropylene filter cloth.
- the crude product (316.9 g) was distilled with a spinning band distillation column at 100 mm Hg.
- a first fraction (52.2 g fraction) boiling at 34°C-(37- 39)°C was mostly F-2-octene.
- An about 2 g intermediate fraction at 90°C- 98°C was obtained.
- a major fraction boiling at 99°C - (102 - 1 10)°C was obtained and weighed 195.3 g.
- a small sample of the main fraction was heated to reflux at atmospheric pressure in a small RB flask with condenser and the boiling point was 164.5°C.
- GC/MS analysis indicated that the major fraction was a mixture of at least 9 measurable
- Example 2 demonstrates the reaction of 2,2,3,3-tetrafluoropropanol with perfluorooct-2-ene.
- a 3-L, 3-neck, Wharton RB flask was set up with overhead mechanical stirring, reflux condenser, heating mantle, Claisen adapter with thermocouple and 250-mL pressure-equalizing addition funnel.
- Perfluorooct-2-ene was analyzed by GC with mass spectral (MS) detection and was found to be 99.1 % octene isomers - 77.1 % F-2- octene and 0.8% of a C 6 F 13 H isomer.
- MS mass spectral
- Heating was applied to increase the temperature to approximately 60°C. At that point, 188 g (1 .51 moles) of 45% KOH was slowly added with stirring over a one hour period. The reaction was exothermic and the temperature increased up to about 95°C. After the KOH addition was completed, the reaction was maintained between 75°C and 85°C for an additional 3-hour period. Heating was discontinued and the reaction cooled to ambient conditions with stirring overnight.
- the crude product was decanted in a separatory funnel, dried over magnesium sulfate, and filtered through polypropylene filter cloth. The crude product weighed 700 g and the aqueous layer weighed 224 g.
- a first fraction (94.7 g) boiling at 41 .5°C-(42-45)°C was mostly F-2-octene isomers (33.1 g of mostly F-2-octene was subsequently recovered in the dry ice trap).
- a major fraction boiling at 99°C - (101 - 1 10)°C was obtained and weighed 456.9 g.
- the distillation heel weighed 107.9 g.
- GC/MS analysis indicated that the major fraction was a mixture of at least 12 measurable components. Seven components were equal to or greater than 1 % in relative concentration. Most components had a mass spectral ion (m-19) at 493 Daltons that was indicative of 2,2,3,3-tetrafluoropropyl perfluorooctene ethers. 1 H and 19 F NMR was used to help identify the major unsaturated and saturated components.
- CF 3 CF CFCF(OCH3)CF 2 CF 2 CF3 and 15%
- Solvent #1 The ability of Solvent #1 to dissolve a fluorinated oil is determined by adding an amount of the oil to the solvent until the mixture became turbid or split into two phases. The results in Table 1 show that Solvent #1 has an excellent ability to dissolve the fluorinated oil. In addition, a solution of 0.5 wt % of the oil is prepared. Pre-weighed metal coupons are dipped into the solution, the solvent evaporated, and the coupon is re- weighed. Table 2 shows the average coating obtained by this dip coating process. Reported coatings weights are the average of three samples. Thus, Solvent #1 can be used as carrier fluid for the deposition of the fluorinated oil onto a substrate.
- a cleaning solvent comprises about 40%
- CF 3 CF2CF CFCF(OCH2CH3)CF 2 CF3, 35%
- CF 3 CF2C(OCH2CH3) CFCF2CF 2 CF3 and
- CF 3 CF2CF C(OCH2CH3)CF2CF 2 CF3, 18%
- CF 3 CF CFCF(OCH2CH3)CF2CF 2 CF3 and 7 %
- the ability of Solvent #2 to clean a fluorinated oil off a substrate is determined by preparing metal coupons that are coated in Krytox GPL 106 oil and then cleaning the coupons. After coating the coupon with oil, the coupon is immersed into Solvent #2 at a temperature of about 120 C for 5 minutes. The weights of the coupon before and after cleaning are measured and the % oil removed is calculated. Results in Table 3 indicate the ability of the solvent to remove the oil and therefore the solvent would be an effective cleaning agent. Table 3
- FPPOE 2,2,3, 3-tetrafluoropropyl perfluorooctene ether
- FPPHE 2, 2, 3, 3-tetrafluoropropyl perfluoroheptene ether
- Krytox GPL 106 Oil is wiped onto a clean metal coupon, of known weight, with a swab. The weight of the coupon is recorded, and then the coupon was cleaned by immersion into FPPHE or FPPOE at the room temperature. The coupon is immersed for 1 minute then air dried. The coupon is then reweighed and the percent of oil removed was determined.
Abstract
Disclosed are compositions comprising at least one unsaturated fluoroalkyi perfluoroalkene ether having a formula selected from the group consisting of CF3(CF2)xCF=CFCF(OR)(CF2)yCF3, CF3(CF2)xC(OR)=CFCF2(CF2)yCF3, CF3CF=CFCF(OR)(CF2)x(CF2)yCF3, CF3(CF2)xCF=C(OR)CF2(CF2)yCF3, and mixtures thereof; wherein x and y are independently 0, 1, 2, 3 or 4 and wherein x + y = 0, 1, 2, 3 or 4; and wherein R is 2,2,3,3-tetrafluoro-1 -propyl, 2,2,3,3,3-pentafluoro-1 -propyl, 2,2,2-trifluoro-1 -ethyl, 2,2,3,3,4,4,5,5-octafluoro-1 -pentyl, or 1,1,1,3,3,3- hexafluoro-2-propyl. Also disclosed herein are novel methods of using a composition comprising at least one of the compounds described above as novel solvents, carrier fluids, dewatering agents, degreasing solvents or defluxing solvents.
Description
TITLE
COMPOSITION COMPRISING FLUOROALKYL PERFLUOROALKENE ETHERS AND USES THEREOF CROSS REFERENCE(S) TO RELATED APPLICATION(S)
This application claims the benefit of priority of U.S. Provisional Applications 61/568,781 , filed December 9, 201 1
BACKGROUND INFORMATION
Field of the Disclosure
This invention relates to cleaning compositions comprising unsaturated fluorocarbon ethers. The invention further relates to use of said cleaning compositions in methods to clean, degrease, deflux, dewater, and deposit fluorolubricant. The invention further relates to novel unsaturated fluorocarbon ethers and their use as cleaning compositions and in the methods listed above.
Description of the Related Art
Chlorofluorocarbon (CFC) compounds have been used extensively in the area of semiconductor manufacture to clean surfaces such as magnetic disk media. However, chlorine-containing compounds such as CFC compounds are considered to be detrimental to the Earth's ozone layer. In addition, many of the hydrofluorocarbons used to replace CFC compounds have been found to contribute to global warming. Therefore, there is a need to identify new environmentally safe solvents for cleaning applications, such as removing residual flux, lubricant or oil contaminants, and particles. There is also a need for identification of new solvents for deposition of fluorolubricants and for drying or dewatering of substrates that have been processed in aqueous solutions.
The present invention provides new compositions comprising unsaturated fluorocarbon ethers, and methods of manufacture of such unsaturated fluorocarbon ethers. These compositions have utility in many of the applications formerly served by CFC compounds. The compositions of the present invention possess some or all of the desired properties of little or no environmental impact, ability to dissolve oils, greases or
lubricants (in particular fluorine-containing lubricants), non-flammability, and ability to dissolve surfactant compounds used in methods for drying or dewatering. SUMMARY
In one embodiment, disclosed here are composition comprising at least one unsaturated fluoroalkyl perfluoroalkene ether having a formula selected from the group consisting of CF3(CF2)xCF=CFCF(OR)(CF2)yCF3, CF3(CF2)xC(OR)=CFCF2(CF2)yCF3, CF3CF=CFCF(OR)(CF2)x(CF2)yCF3, CF3(CF2)xCF=C(OR)CF2(CF2)yCF3, and mixtures thereof; wherein x and y are independently 0, 1 , 2, 3 or 4 and wherein x + y = 0, 1 , 2, 3 or 4; and wherein R is 2,2,3,3-tetrafluoro-1 -propyl, 2,2,3,3,3-pentafluoro-1 -propyl, 2,2,2-trifluoro-1 -ethyl, 2,2,3,3,4,4,5,5-octafluoro-1 -pentyl, or 1 ,1 ,1 ,3,3,3- hexafluoro-2-propyl.
In another embodiment, disclosed here are compositions
comprising a compound having the formula having the formula
CF3(CF2)xCF=CFCF(OR)(CF2)yCF3, wherein x and y are independently 0, 1 , 2, 3 or 4 and wherein x + y = 0, 1 , 2, 3 or 4; and wherein R is 2,2,3,3- tetrafluoro-1 -propyl, 2,2,3,3,3-pentafluoro-1 -propyl, 2,2,2-trifluoro-1 -ethyl, 2,2,3,3,4,4,5,5-octafluoro-1 -pentyl, or 1 ,1 ,1 ,3,3,3-hexafluoro-2-propyl.
In another embodiment, disclosed herein are compositions comprising a compound having the formula
CF3(CF2)xC(OR)=CFCF2(CF2)yCF3, wherein x and y are independently 0, 1 , 2, 3 or 4 and wherein x + y = 0, 1 , 2, 3 or 4; and wherein R is 2,2,3,3- tetrafluoro-1 -propyl, 2,2,3,3,3-pentafluoro-1 -propyl, 2,2, 2-trifluoro-1 -ethyl, 2,2,3,3,4,4,5,5-octafluoro-1 -pentyl, or 1 ,1 ,1 ,3,3,3-hexafluoro-2-propyl.
In another embodiment, disclosed herein are compositions comprising a compound having the formula
CF3CF=CFCF(OR)(CF2)x(CF2)yCF3, wherein x and y are independently 0, 1 , 2, 3 or 4 and wherein x + y = 0, 1 , 2, 3 or 4; and wherein R is 2,2,3,3- tetrafluoro-1 -propyl, 2,2,3,3,3-pentafluoro-1 -propyl, 2,2,2-trifluoro-1 -ethyl, 2,2,3,3,4,4,5,5-octafluoro-1 -pentyl, or 1 ,1 ,1 ,3,3,3-hexafluoro-2-propyl.
In another embodiment, disclosed herein are compositions comprising a compound having the formula
CF3(CF2)xCF=C(OR)CF2(CF2)yCF3, wherein x and y are independently 0, 1 , 2, 3 or 4 and wherein x + y = 0, 1 , 2, 3 or 4; and wherein 2,2,3,3- tetrafluoro-1 -propyl, or 1 ,1 ,1 , 3,3, 3-hexafluoro-2-propyl.
In yet another embodiment, disclosed herein are novel methods of using a composition comprising at least one unsaturated fluoroalkyl perfluoroalkene ether having a formula selected from the group consisting of CF3(CF2)xCF=CFCF(OR)(CF2)yCF3, CF3(CF2)xC(OR)=CFCF2(CF2)yCF3, CF3CF=CFCF(OR)(CF2)x(CF2)yCF3, CF3(CF2)xCF=C(OR)CF2(CF2)yCF3, and mixtures thereof; wherein x and y are independently 0, 1 , 2, 3 or 4 and wherein x + y = 0, 1 , 2, 3 or 4; and wherein R is 2,2,3,3-tetrafluoro-1 - propyl, 2,2,3,3,3-pentafluoro-1 -propyl, 2,2,2-trifluoro-1 -ethyl,
2,2,3,3,4,4,5,5-octafluoro-1 -pentyl, or 1 ,1 ,1 ,3,3,3-hexafluoro-2-propyl.
In yet another embodiment, disclosed herein are novel methods of manufacturing fluorocarbon ethers, including those above.
The foregoing general description and the following detailed description are exemplary and explanatory only and are not restrictive of the invention, as defined in the appended claims.
DETAILED DESCRIPTION
Disclosed herein are compositions comprising at least one unsaturated fluoroalkyl perfluoroalkene ether having a formula selected from the group consisting of CF3(CF2)xCF=CFCF(OR)(CF2)yCF3,
CF3(CF2)xC(OR)=CFCF2(CF2)yCF3, CF3CF=CFCF(OR)(CF2)x(CF2)yCF3, CF3(CF2)xCF=C(OR)CF2(CF2)yCF3, and mixtures thereof; wherein x and y are independently 0, 1 , 2, 3 or 4 and wherein x + y = 0, 1 , 2, 3 or 4; and wherein R is 2,2,3,3-tetrafluoro-1 -propyl, 2,2,3,3,3-pentafluoro-1 -propyl, 2,2,2-trifluoro-1 -ethyl, 2,2,3,3,4,4,5,5-octafluoro-1 -pentyl, or 1 ,1 ,1 ,3,3,3- hexafluoro-2-propyl,.
Generally, the above described compositions are formed when CF3(CF2)xCF=CFCF2(CF2)yCF3, CF3(CF2)xCF=CFCF2(CF2)yCF3,
CF3CF=CFCF2(CF2)x(CF2)yCF3, CF3(CF2)xCF=CFCF2(CF2)yCF3, or mixtures thereof react with 2, 2, 3,3-tetrafluoro-1 -propanol, 2,2,3,3,3- pentafluoro-1 -propanol, 2,2,2-trifluoroethanol, 2,2,3,3,4,4,5,5-octafluoro-1 - pentanol, or 1 ,1 ,1 ,3,3,3-hexafluoro-2-propanol.
In one embodiment, the fluorinated alcohol is 2,2,3,3-tetrafluoro-1 - propanol, 2,2,3,3,3-pentafluoro-1 -propanol, 2,2,2-trifluoroethanol,
2,2,3,3 ,4,4,5,5-octafluorO-l -pentanol, or 1 ,1 ,1 ,3,3,3-hexafluoro-2-propanol, or any mixture thereof. Also disclosed herein, in one embodiment, are compositions disclosed above, wherein said unsaturated fluoroalkyl perfluoroalkene ether comprises a compound having the formula
CF3(CF2)xCF=CFCF(OR)(CF2)yCF3. In another embodiment, the above compositions further comprise a compound having the formula
CF3(CF2)xC(OR)=CFCF2(CF2)yCF3. In another embodiment, in the above compositions, said unsaturated fluoroalkyl perfluoroalkene ether
comprises a compound having the formula
CF3(CF2)xC(OR)=CFCF2(CF2)yCF3. In another embodiment, in the above compositions, said unsaturated fluoroalkyl perfluoroalkene ether
comprises a compound having the formula
CF3CF=CFCF(OR)(CF2)x(CF2)yCF3. In another embodiment, in the above compositions, said unsaturated fluoroalkyl perfluoroalkene ether
comprises a compound having the formula
CF3(CF2)xCF=C(OR)CF2(CF2)yCF3.
In another embodiment, disclosed herein are novel methods of using a composition comprising at least one unsaturated fluoroalkyl perfluoroalkene ether selected from the group consisting of
CF3(CF2)xCF=CFCF(OR)(CF2)yCF3, CF3(CF2)xC(OR)=CFCF2(CF2)yCF3, CF3CF=CFCF(OR)(CF2)x(CF2)yCF3, CF3(CF2)xCF=C(OR)CF2(CF2)yCF3, and mixtures thereof; wherein x and y are independently 0, 1 , 2, 3 or 4 and wherein x + y = 0, 1 , 2, 3 or 4; and wherein R is 2,2,3,3-tetrafluoro-1 - propyl, 2,2,3,3,3-pentafluoro-1 -propyl, 2,2,2-trifluoro-1 -ethyl,
2,2,3,3,4,4,5,5-octafluoro-1 -pentyl, or 1 ,1 ,1 ,3,3,3-hexafluoro-2-propyl.
Many aspects and embodiments have been described above and are merely exemplary and not limiting. After reading this specification, skilled artisans appreciate that other aspects and embodiments are possible without departing from the scope of the invention.
Other features and benefits of any one or more of the embodiments will be apparent from the following detailed description, and from the claims.
Before addressing details of embodiments described below, some terms are defined or clarified.
For purposes of the present invention, a phase transfer catalyst is a substance that facilitates the transfer of ionic compounds (e.g., reactants or components) into an organic phase. The phase transfer catalyst facilitates the reaction of these dissimilar and incompatible components. While various phase transfer catalysts may function in different ways, their mechanism of action is not determinative of their utility in the present process.
In one embodiment, the compounds disclosed herein are
unsaturated fluoroethers which have utility as novel solvents, carrier fluids, dewatering agents, degreasing solvents or defluxing solvents.
In one embodiment, unsaturated fluoroalkyl perfluoroalkene ethers of the invention represent compounds having a formula selected from the group consisting of CF3(CF2)xCF=CFCF(OR)(CF2)yCF3,
CF3(CF2)xC(OR)=CFCF2(CF2)yCF3, CF3CF=CFCF(OR)(CF2)x(CF2)yCF3, CF3(CF2)xCF=C(OR)CF2(CF2)yCF3, and mixtures thereof; wherein x and y are independently 0, 1 , 2, 3 or 4 and wherein x + y = 0, 1 , 2, 3 or 4; and wherein R is 2,2,3,3-tetrafluoro-1 -propyl, 2,2,3,3,3-pentafluoro-1 -propyl, 2,2,2-trifluoro-1 -ethyl, 2,2,3,3,4,4,5,5-octafluoro-1 -pentyl, or 1 ,1 ,1 ,3,3,3- hexafluoro-2-propyl. In one embodiment, the compositions disclosed herein may be prepared by contacting at least one perfluoroalkene, such as perfluoro-3-heptene, pefluoro-2-heptene, perfluoro-2-hexene, perfluoro-
3- hexene, perfluoro-2-pentene, perfluoro-2-octene, perfluoro-3-octene, perfluoro-4-octene, perfluoro-2-nonene, perfluoro-3-nonene, or perfluoro-
4- nonene with a fluorinated alcohol in the presence of a strong base. The fluorinated alcohol is defined by the formula R-OH, wherein R is 2,2,3,3- tetrafluoro-1 -propyl, 2,2,3,3,3-pentafluoro-1 -propyl, 2,2,2-trifluoro-1 -ethyl, 2,2,3,3,4,4,5,5-octafluoro-1 -pentyl, or 1 ,1 ,1 ,3,3,3-hexafluoro-2-propyl . For example, perfluoro-3-heptene may be reacted with at least one fluorinated alcohol in presence of a strong base. Such fluorinated alcohols include 2,2,3,3-tetrafluoro-1 -propanol, 2,2,3,3,3-pentafluoro-1 -propanol, 2,2,2- trifluoroethanol, 2,2,3,3,4,4,5,5-octafluoro-1 -pentanol, or 1 ,1 ,1 ,3,3,3- hexafluoro-2-propanol, or any mixture thereof.
In one embodiment, Table 1 below lists boiling points at 760 torr for unsaturated fluoroalkyl perfluoroalkene ethers where x+y = 3 prepared with alcohols with the indicated R groups and perfluorooctene.
Table 1
In one embodiment, the strong base is a base which will react with a fluorinated alcohol to produce an alkoxide upon combination of the base with said fluorinated alcohol. Bases which can be used to form such alkoxides include alkali metal hydroxides, such as sodium hydroxide or potassium hydroxide without limitation.
In one embodiment, the strong base is present in the form of an aqueous solution having a concentration of alkali metal hydroxide of from 10% by weight to 45% by weight. In one embodiment, one mole of alkali metal hydroxide is used per mole of fluorinated alcohol to produce the alkoxide. In another embodiment, 1 .1 moles of alkali metal hydroxide per mole of fluorinated alcohol is used. In yet another embodiment about 0.9 moles of alkali metal hydroxide per mole of fluorinated alcohol is used.
In one embodiment, one mole of alkali metal hydroxide is used per mole of perfluoroalkene. In another embodiment, about 1 .1 moles of alkali metal hydroxide are used per mole of perfluoroalkene. In yet another embodiment, about 1 .05 moles of alkali metal hydroxide are used per mole of perfluoroalkene.
In one embodiment, the alkali metal hydroxide is combined with the perfluoroalkene, and then a fluorinated alcohol and water are added to the mixture of perfluoroalkene and base, resulting in an immediate exothermic reaction. In another embodiment, the alkali metal hydroxide is dissolved in water and mixed with the perfluoroalkene. Addition of the fluorinated
alcohol results in an immediate exothermic reaction to produce the unsaturated alkyl perfluoroalkene ethers.
In one embodiment, the fluorinated alcohol is added to the perfluoroalkene, alkali metal hydroxide and water in one portion. In another embodiment, the fluorinated alcohol is added slowly over a period of time. In one embodiment, the fluorinated alcohol is added over one hour. In another embodiment, the fluorinated alcohol is added over two hours. In yet another embodiment, the perfluoroalkene, alkali metal hydroxide and fluorinated alcohol are added together, and the water is added slowly over time.
In one embodiment, the perfluoroalkene, alkali metal hydroxide, fluorinated alcohol and water are all added at about room temperature. In another embodiment, the perfluoroalkene and aqueous solution of alkali metal hydroxide are heated to about 50°C, and the fluorinated alcohol is added slowly over a period of time.
In one embodiment, a phase transfer catalyst is added to the mixture of perfluoroalkene, alkali metal hydroxide, fluorinated alcohol and water. In one embodiment a phase transfer catalyst is a quaternary ammonium salt. In one embodiment, a phase transfer catalyst is
Aliquat®336. In one embodiment, the amount of phase transfer catalyst is from about 1 % by weight to about 10% by weight of the alkali metal hydroxide.
The phase transfer catalyst can be ionic or neutral and is selected from the group consisting of crown ethers, onium salts, cryptates and polyalkylene glycols and derivatives thereof, and mixtures thereof. An effective amount of the phase transfer catalyst should be used in order to effect the desired reaction; such an amount can be determined by limited experimentation once the reactants, process conditions and phase transfer catalyst are selected.
Crown ethers are cyclic molecules in which ether groups are connected by dimethylene linkages; the compounds form a molecular structure that is believed to be capable of "receiving" or holding the alkali metal ion of the hydroxide and to thereby facilitate the reaction.
Particularly useful crown ethers include 18-crown-6, especially in
combination with potassium hydroxide; 15-crown-5, especially in combination with sodium hydroxide; 12-crown-4, especially in combination with lithium hydroxide. Derivatives of the above crown ethers are also useful, e.g., dibenzo-18-crown-6, dicyclohexano-18-crown-6, and dibenzo- 24-crown-8 as well as 12-crown-4. Other polyethers particularly useful for alkali metal compounds, and especially for lithium, are described in U.S. Pat. No. 4,560,759 which is incorporated herein by reference to the extent permitted. Other compounds analogous to the crown ethers and useful for the same purpose are compounds which differ by the replacement of one or more of the oxygen atoms by other kinds of donor atoms, particularly N or S, such as hexamethyl-[14]-4,1 1 -dieneN4.
Onium salts include quaternary phosphonium salts and quaternary ammonium salts that may be used as the phase transfer catalyst in the process of the present invention; such compounds can be represented by the following formulas I and II:
R1 R2 R3 R4 P(+) X-W (I)
R1 R2 R3 R4 N(+) X-W (II)
wherein each of Ri , F¾, R3 and R4, which may be the same or different, is an alkyl group, an aryl group or an aralkyl group, and X' is a halogen atom. Specific examples of these compounds include
tetramethylammonium chloride, tetramethylammonium bromide, benzyltriethylammonium chloride, methyltrioctylammonium chloride (available commercially under the brands Aliquat(R) 336 and Adogen 464), tetra-n-butylammonium chloride, tetra-n-butylammonium bromide, tetra-n-butylammonium hydrogen sulfate, tetra-n-butylphosphonium chloride, tetraphenylphosphonium bromide, tetraphenylphosphonium chloride, triphenylmethylphosphonium bromide and
triphenylmethylphosphonium chloride. Among them,
benzyltriethylammonium chloride is preferred for use under strongly basic conditions. Other useful compounds within this class of compounds include those exhibiting high temperature stabilities (e.g., up to about 200.degree. C.) and including 4-dialkylaminopyridinium salts such as tetraphenylarsonium chloride, bis[tris(dimethylamino)phosphine]iminium chloride and tetratris[tris(dimethylamino)phosphinimino]phosphonium
chloride; the latter two compounds are also reported to be stable in the presence of hot, concentrated sodium hydroxide and, therefore, can be particularly useful.
Polyalkylene glycol compounds useful as phase transfer catalysts can be represented by the formula:
R6O(R5O)t R7 (III)
wherein R5 is an alkylene group, each of R6 and R7, which may be the same or different, is a hydrogen atom, an alkyl group, an aryl group or, an aralkyi group, and t is an integer of at least 2. Such compounds include, for example glycols such as diethylene glycol, triethylene glycol, tetraethylene glycol, pentaethylene glycol, hexaethylene glycol,
diisopropylene glycol, dipropylene glycol, tripropylene glycol,
tetrapropylene glycol and tetramethylene glycol, and monoalkyl ethers such as monomethyl, monoethyl, monopropyl and monobutyl ethers of such glycols, dialkyi ethers such as tetraethylene glycol dimethyl ether and pentaethylene glycol dimethyl ether, phenyl ethers, benzyl ethers, and polyalkylene glycols such as polyethylene glycol (average molecular weight about 300) dimethyl ether, polyethylene glycol (average molecular weight about 300) dibutyl ether, and polyethylene glycol (average molecular weight about 400) dimethyl ether. Among them, compounds wherein both R6 and R7 are alkyl groups, aryl groups or aralkyi groups are preferred.
Cryptates are another class of compounds useful in the present as phase transfer catalysts. These are three-dimensional polymacrocyclic chelating agents that are formed by joining bridgehead structures with chains that contain properly spaced donor atoms. For example, bicyclic molecules that result from joining nitrogen bridgeheads with chains of (- OCH2CH2-) groups as in 2.2.2-cryptate (4,7,13,16,21 ,24-hexaoxa-1 , 10- diasabicyclo-(8.8.8)hexacosane; available under the brand names cryptand 222 and Kryptofix 222). The donor atoms of the bridges may all be O, N, or S, or the compounds may be mixed donor macrocycles in which the bridge strands contain combinations of such donor atoms.
Combinations of phase transfer catalysts from within one of the groups described above may also be useful as well as combinations or
mixtures from more than one group, for example, crown ethers and oniums, or from more than two of the groups, e.g., quaternary
phosphonium salts and quaternary ammonium salts, and crown ethers and polyalkylene glycols.
In one embodiment, after several hours the reaction mixture is allowed to cool to ambient temperature and poured into a separatory funnel. The lower organic layer comprises unsaturated fluoroalkyl perfluoroalkene ether, and is separated from an aqueous layer containing inorganic salts. The organic layer is then dried, and then can be further purified by distillation. In one embodiment, the organic layer is dried over anhydrous magnesium sulfate. In another embodiment, the organic layer is dried over anhydrous sodium sulfate. In one embodiment of a preparation of alkyl perfluoroheptene ethers, a fraction is collected from the distillation predominantly between 108°C and 122°C, depending on whether the methyl or ethyl ethers were prepared, comprising a mixture of allylic and vinylic perfluoroalkene alkyl ethers.
In one embodiment, the present compositions may further comprise a propellant. Aerosol propellant may assist in delivering the present composition from a storage container to a surface in the form of an aerosol. Aerosol propellant is optionally included in the present composition in up to about 25 weight percent of the total composition. Representative aerosol propellants comprise air, nitrogen, carbon dioxide, difluoromethane (CF2H2, HFC-32), trifluoromethane (CF3H, HFC-23), difluoroethane (CHF2CH3, HFC-152a), trifluoroethane (CH3CF3, HFC- 143a; or CHF2CH2F, HFC-143), tetrafluoroethane (CF3CH2F, HFC-134a; or CF2HCF2H, HFC-134), pentafluoroethane (CF3CF2H, HFC-125), 1 ,3,3,3-tetrafluoro-1 -propene (HFO-1234ze), 2,3,3,3-tetrafluoro-1 -propene (HFO-1234yf), 1 ,2,3,3,3-pentafluoropropene (HFO-1225ye), 1 ,1 ,3,3,3- pentafluoropropene (HFO-1225ze) and hydrocarbons, such as propane, butanes, or pentanes, or dimethyl ether.
In another embodiment, the present compositions may further comprise at least one surfactant. The surfactants of the present invention include all surfactants known in the art for dewatering or drying of substrates. Representative surfactants include alkyl phosphate amine
salts (such as a 1 :1 salt of 2-ethylhexyl amine and isooctyl phosphate); ethoxylated alcohols, mercaptans or alkylphenols; quaternary ammonium salts of alkyl phosphates (with fluoroalkyl groups on either the ammonium or phosphate groups); and mono- or di-alkyl phosphates of fluorinated amines. Additional fluorinated surfactant compounds are described in U. S. Patent No. 5,908,822, incorporated herein by reference.
The amount of surfactant included in the dewatering compositions of the present invention can vary widely depending on the particular drying application in which said composition will be used, but is readily apparent to those skilled in the art. In one embodiment, the amount of surfactant dissolved in the unsaturated fluorinated ether solvent is not greater than about 1 weight percent, based on the total weight of the surfactant/solvent composition. In another embodiment, larger amounts of surfactant can be used, if after treatment with the composition, the substrate being dried is thereafter treated with solvent containing either no or minimal surfactant. In one embodiment, the amount of surfactant is at least about 50 parts per million (ppm, on a weight basis). In another embodiment, the amount of surfactant is from about 100 to about 5000 ppm. In yet another
embodiment, the amount of surfactant used is from about 200 to about 2000 ppm based on the total weight of the dewatering composition.
Optionally, other additives may be included in the present compositions comprising solvents and surfactants for use in dewatering. Such additives include compounds having antistatic properties; the ability to dissipate static charge from non-conductive substrates such as glass and silica. Use of an antistatic additive in the dewatering compositions of the present invention may be necessary to prevent spots and stains when drying water or aqueous solutions from electrically non-conductive parts such as glass lenses and mirrors. Most unsaturated fluoroether solvents of the present invention also have utility as dielectric fluids, i.e., they are poor conductors of electric current and do not easily dissipate static charge. Boiling and general circulation of dewatering compositions in conventional drying and cleaning equipment can create static charge, particularly in the latter stages of the drying process where most of the water has been removed from a substrate. Such static charge collects on
non-conductive surfaces of the substrate and prevents the release of water from the surface. The residual water dries in place resulting in undesirable spots and stains on the substrate. Static charge remaining on substrates can bring out impurities from the cleaning process or can attract impurities such as lint from the air, which results in unacceptable cleaning performance. In one embodiment, desirable antistatic additives are polar compounds, which are soluble in the present unsaturated fluorinated ether solvent and result in an increase in the conductivity of the unsaturated fluorinated ether solvent resulting in dissipation of static charge from a substrate. In another embodiment, the antistatic additives have a normal boiling point near that of the unsaturated fluorinated ether solvent and have minimal to no solubility in water. In yet another embodiment, the antistatic additives have a solubility in water of less than about 0.5 weight percent. In one embodiment, the solubility of antistatic agent is at least 0.5 weight percent in unsaturated fluorinated ether solvent. In one embodiment, the antistatic additive is nitromethane
In one embodiment, the present dewatering composition containing an antistatic additive is effective in both the dewatering and drying and rinse steps of a method to dewater or dry a substrate as described below.
Another embodiment relates to a method for dewatering or drying a substrate comprising:
(a) contacting the substrate with a composition comprising at least one unsaturated fluoroalkyl perfluoroalkene ether having a formula selected from the group consisting of CF3(CF2)xCF=CFCF(OR)(CF2)yCF3,
CF3(CF2)xC(OR)=CFCF2(CF2)yCF3, CF3CF=CFCF(OR)(CF2)x(CF2)yCF3, CF3(CF2)xCF=C(OR)CF2(CF2)yCF3, and mixtures thereof; wherein x and y are independently 0, 1 , 2, 3 or 4 and wherein x + y = 0, 1 , 2, 3 or 4; and wherein R is 2,2,3,3-tetrafluoro-1 -propyl, 2,2,3,3,3-pentafluoro-1 -propyl, 2,2,2-trifluoro-1 -ethyl, 2,2,3,3,4,4,5,5-octafluoro-1 -pentyl, or 1 ,1 ,1 ,3,3,3- hexafluoro-2-propyl, , containing surfactant, thereby dewatering said substrate and
(b) recovering the dewatered substrate from the composition.
Many industries use aqueous compositions for the surface treatment of metals, ceramics, glasses, and plastics. Cleaning, plating, and deposition of coatings are often carried out in aqueous media and are usually followed by a step in which residual water is removed. Hot air drying, centrifugal drying, and solvent-based water displacement are methods used to remove such residual water.
While hydrofluorocarbons (HFCs) have been proposed as replacements for the previously used CFC solvents in drying or dewatering applications, many HFCs have limited solvency for water. The use of surfactant, which assists in removal of water from substrates is therefore necessary in many drying or dewatering methods. Hydrophobic
surfactants have been added to dewatering or drying solvents to displace water from substrates.
The primary function of the dewatering or drying solvent
(unsaturated fluorinated ether solvent) in a dewatering or drying
composition is to reduce the amount of water on the surface of a substrate being dried. The primary function of the surfactant is to displace any remaining water from the surface of the substrate. When the unsaturated fluorinated ether solvent and surfactant are combined, a highly effective displacement drying composition is attained.
In one embodiment, the surfactant for dewatering and drying is soluble to at least 1 weight percent based on the total solvent/surfactant composition weight.
In one embodiment, the dewatering or drying method of the present disclosure is very effective in displacing water from a broad range of substrates including metals, such as tungsten, copper, gold, beryllium, stainless steel, aluminum alloys, brass and the like; from glasses and ceramic surfaces, such as glass, sapphire, borosilicate glass, alumina, silica such as silicon wafers used in electronic circuits, fired alumina and the like; and from plastics such as polyolefin ("Alathon", Rynite®, "Tenite"), polyvinylchloride, polystyrene (Styron), polytetrafluoroethylene (Teflon®), tetrafluoroethylene-ethylene copolymers (Tefzel®), polyvinylidenefluoride ("Kynar"), ionomers (Surlyn®), acrylonitrile-butadiene-styrene polymers
(Kralac®), phenol-formaldehyde copolymers, cellulosic ("Ethocel"), epoxy resins, polyacetal (Delrin®), poly(p-phenylene oxide) (Noryl®),
polyetherketone ("Ultrapek"), polyetheretherketone ("Victrex"),
poly(butylene terephthalate) ("Valox"), polyarylate (Arylon®), liquid crystal polymer, polyimide (Vespel®), polyetherimides ("Ultem"), polyamideimides ("Torlon"), poly(p-phenylene sulfide) ("Rython"), polysulfone ("Udel"), and polyaryl sulfone ("Rydel"). In another embodiment, the compositions for use in the present dewatering or drying method are compatible with elastomers.
In one embodiment, the disclosure is directed to a process for removing at least a portion of water from, i.e., dewatering, the surface of a wetted substrate, which comprises contacting the substrate with the aforementioned dewatering composition, and then removing the substrate from contact with the dewatering composition. In one embodiment, water originally bound to the surface of the substrate is displaced by solvent and/or surfactant and leaves with the dewatering composition. By "at least a portion of water" is meant at least about 75 weight percent of water at the surface of a substrate is removed per immersion cycle. By "immersion cycle" is meant one cycle involving at least a step wherein substrate is immersed in the present dewatering composition. Optionally, minimal amounts of surfactant remaining adhered to the substrate can be further removed by contacting the substrate with surfactant-free halocarbon solvent. Holding the article in the solvent vapor or refluxing solvent will further decrease the presence of surfactant remaining on the substrate. Removal of solvent adhering to the surface of the substrate is effected by evaporation. Evaporation of solvent at atmospheric or subatmospheric pressures can be employed and temperatures above and below the boiling point of the halocarbon solvent can be used.
Methods of contacting the substrate with dewatering composition are not critical and can vary widely. For example, the substrate can be immersed in the composition, or the substrate can be sprayed with the composition using conventional equipment. Complete immersion of the substrate is preferred as it generally insures contact between the
composition and all exposed surfaces of the substrate. However, any other method, which can easily provide such complete contact may be used.
The time period over which substrate and dewatering composition are contacted can vary widely. Usually, the contacting time is up to about 5 minutes, however, longer times may be used if desired. In one embodiment of the dewatering process, the contacting time is from about 1 second to about 5 minutes. In another embodiment, the contacting time of the dewatering process is from about 15 seconds to about 4 minutes.
Contacting temperatures can also vary widely depending on the boiling point of the composition. In general, the contacting temperature is equal to or less than the composition's normal boiling point.
In one embodiment, the compositions of the present disclosure may further contain a co-solvent. Such co-solvents are desirable where the present compositions are employed in cleaning conventional process residue from substrates, e.g., removing soldering fluxes and degreasing mechanical components comprising substrates of the present invention. Such co-solvents include alcohols (such as methanol, ethanol,
isopropanol), ethers (such as diethyl ether, methyl tertiary-butyl ether), ketones (such as acetone), esters (such as ethyl acetate, methyl dodecanoate, isopropyl myristate and the dimethyl or diisobutyl esters of succinic, glutaric or adipic acids or mixtures thereof), ether alcohols (such as propylene glycol monopropyl ether, dipropylene glycol monobutyl ether, and tripropylene glycol monomethyl ether), and hydrocarbons (such as pentane, cyclopentane, hexane, cyclohexane, heptane, octane), and hydrochlorocarbons (such as trans-1 ,2-dichloroethylene). When such a co-solvent is employed with the present composition for substrate dewatering or cleaning, it may be present in an amount of from about 1 weight percent to about 50 weight percent based on the weight of the overall composition.
In cleaning apparatuses, including vapor degreasing and vapor defluxing equipment, compositions may be lost during operation through leaks in shaft seals, hose connections, soldered joints and broken lines. In addition, the working composition may be released to the atmosphere
during maintenance procedures on equipment. If the composition is not a pure component, the composition may change when leaked or discharged to the atmosphere from the equipment, which may cause the composition remaining in the equipment to exhibit unacceptable performance.
Accordingly, it is desirable to use as a cleaning composition comprising a single unsaturated fluorinated ether.
In one embodiment, the unsaturated fluoroalkyl perfluoroalkene ethers described here further comprise an epoxide as an acid acceptor. In one embodiment, the concentration of such epoxides may range from at least 0.001 weight percent to not more than 1 .0 weight percent. In another embodiment, the concentration is from 0.02 weight percent to not more than 0.5 weight percent. In yet another embodiment, the be used at a concentration of not more than 0.2 weight percent of the total composition. The amount of epoxide may range between any combination of these values, inclusive of the recited values.
Examples of suitable epoxides include aliphatic and aromatic epoxides including those selected from epichlorohydrin, 2-hexene epoxide, 3-hexene epoxide, glycidol, propylene oxide, cis-2,3-pentene oxide, 2-methyl-2,3-epoxybutane, 1 ,2-epoxycyclopentene, 2, 3-d i methyl - 2,3-epoxybutane, 1 ,2-epoxycyclohexane, 1 ,2-butylene oxide and 2,3- butylene oxide. In another embodiment, the epoxide is a saturate mono- epoxide containing from 3 to 8 carbon atoms.
Another embodiment relates to a method of cleaning a surface comprising:
(a) contacting the surface with a composition comprising at least one unsaturated fluoroalkyl perfluoroalkene ether having a formula selected from the group consisting of
CF3(CF2)xCF=CFCF(OR)(CF2)yCF3,
CF3(CF2)xC(OR)=CFCF2(CF2)yCF3,
CF3CF=CFCF(OR)(CF2)x(CF2)yCF3,
CF3(CF2)xCF=C(OR)CF2(CF2)yCF3, and mixtures thereof; wherein x and y are independently 0, 1 , 2, 3 or 4 and wherein x + y = 0, 1 , 2, 3 or 4; and wherein R is 2,2,3,3-tetrafluoro-1 -propyl, 2,2,3,3,3-
pentafluoro-1 -propyl, 2,2,2-trifluoro-1 -ethyl, 2,2,3,3,4,4,5,5- octafluoro-1 -pentyl, or 1 ,1 ,1 ,3,3,3-hexafluoro-2-propyl;
(b) recovering the surface from the composition.
In one embodiment, the compositions of the present disclosure are useful as cleaning compositions, cleaning agents, deposition solvents and as dewatering or drying solvents. For proper operation in use,
microelectronic components must be cleaned of flux residues, oils and greases, and particulates that may contaminate the surfaces after completion of manufacture. In another embodiment, the present disclosure relates to a process for removing residue from a surface or substrate comprising contacting the surface or substrate with a cleaning composition or cleaning agent of the present invention and, optionally, recovering the surface or substrate substantially free of residue from the cleaning composition or cleaning agent.
In yet another embodiment, the present disclosure relates to a method for cleaning surfaces by removing contaminants from the surface. The method for removing contaminants from a surface comprises contacting the surface having contaminants with a cleaning composition of the present invention to solubilize the contaminants and, optionally, recovering the surface from the cleaning composition. The surface is then substantially free of contaminants.
As stated previously, the contaminants or residues that may be removed by the present method include, but are not limited to oils and greases, flux residues, and particulate contaminants.
In one embodiment of the method, the contacting may be accomplished by spraying, flushing, wiping with a substrate e.g., wiping cloth or paper, that has the cleaning composition incorporated in or on it. In another embodiment of the method, the contacting may be
accomplished by dipping or immersing the disk in a bath of the cleaning composition.
In one embodiment of the method, the recovering is by removing the surface that has been contacted from the cleaning composition bath (in a similar manner as described for the method for depositing an a fluorolubricant on a surface as described below). In another embodiment
of the method, the recovering is by allowing the cleaning composition that has been sprayed, flushed, or wiped on the disk to drain away.
Additionally, any residual cleaning composition that may be left behind after the completion of the previous steps may be evaporated in a manner similar to that for the deposition method as well.
The method for cleaning a surface may be applied to the same types of surfaces as the method for deposition as described below.
Semiconductor surfaces or magnetic media disks of silica, glass, metal or metal oxide, or carbon may have contaminants removed by the method. In the method described above, contaminant may be removed from a disk by contacting the disk with the cleaning composition and recovering the disk from the cleaning composition.
In yet another embodiment, the present method also provides methods of removing contaminants from a product, part, component, substrate, or any other article or portion thereof by contacting the article with a cleaning composition of the present invention. For the purposes of convenience, the term "article" is used herein to refer to all such products, parts, components, substrates, and the like and is further intended to refer to any surface or portion thereof. Furthermore, the term "contaminant" is intended to refer to any unwanted material or substance present on the article, even if such substance is placed on the article intentionally. For example, in the manufacture of semiconductor devices it is common to deposit a photoresist material onto a substrate to form a mask for the etching operation and to subsequently remove the photoresist material from the substrate. The term "contaminant" as used herein is intended to cover and encompass such a photo resist material. Hydrocarbon based oils and greases and dioctylphthalate are examples of the contaminants that may be found on the carbon coated disks.
In one embodiment, the present method comprises contacting the article with a cleaning composition of the invention, in a vapor degreasing and solvent cleaning method. In one such embodiment, vapor degreasing and solvent cleaning methods consist of exposing an article, preferably at room temperature, to the vapors of a boiling cleaning composition. Vapors condensing on the object have the advantage of providing a relatively
clean, distilled cleaning composition to wash away grease or other contamination. Such processes thus have an additional advantage in that final evaporation of the present cleaning composition from the object leaves behind relatively little residue as compared to the case where the object is simply washed in liquid cleaning composition.
In another embodiment, for applications in which the article includes contaminants that are difficult to remove, the present methods involve raising the temperature of the cleaning composition above ambient or to any other temperature that is effective in such application to substantially improve the cleaning action of the cleaning composition. In one such embodiment, such processes are also generally used for large volume assembly line operations where the cleaning of the article, particularly metal parts and assemblies, must be done efficiently and quickly.
In one embodiment, the cleaning methods of the present invention comprise immersing the article to be cleaned in liquid cleaning
composition at an elevated temperature. In another embodiment, the cleaning methods of the present invention comprise immersing the article to be cleaned in liquid cleaning composition at about the boiling point of the cleaning composition. In one such embodiment, this step removes a substantial amount of the target contaminant from the article. In yet another embodiment, this step removes a major portion of the target contaminant from the article. In one embodiment, this step is then followed by immersing the article in freshly distilled cleaning composition, which is at a temperature below the temperature of the liquid cleaning composition in the preceding immersion step. In one such embodiment, the freshly distilled cleaning composition is at about ambient or room temperature In yet another embodiment, the method also includes the step of then contacting the article with relatively hot vapor of the cleaning composition, by exposing the article to vapors rising from the hot/boiling cleaning composition associated with the first mentioned immersion step. In one such embodiment, this results in condensation of the cleaning composition vapor on the article. In certain preferred embodiments, the article may be sprayed with distilled cleaning composition before final rinsing.
It is contemplated that numerous varieties and types of vapor degreasing equipment are adaptable for use in connection with the present methods. One example of such equipment and its operation is disclosed by U.S. Patent No. 3,085,918, which is incorporated herein by reference. The equipment disclosed therein includes a boiling sump for containing a cleaning composition, a clean sump for containing distilled cleaning composition, a water separator, and other ancillary equipment.
The present cleaning methods may also comprise cold cleaning in which the contaminated article is either immersed in the fluid cleaning composition of the present invention under ambient or room temperature conditions or wiped under such conditions with rags or similar objects soaked in the cleaning composition.
Another embodiment relates to a method of depositing a
fluorolubricant on a surface comprising: combining a fluorolubricant and a solvent, said solvent comprising at least one unsaturated fluoroalkyl perfluoroalkene ether having a formula selected from the group consisting of CF3(CF2)xCF=CFCF(OR)(CF2)yCF3, CF3(CF2)xC(OR)=CFCF2(CF2)yCF3, CF3CF=CFCF(OR)(CF2)x(CF2)yCF3, CF3(CF2)xCF=C(OR)CF2(CF2)yCF3, and mixtures thereof; wherein x and y are independently 0, 1 , 2, 3 or 4 and wherein x + y = 0, 1 , 2, 3 or 4; and wherein R is 2,2,3,3-tetrafluoro-1 - propyl, 2,2,3,3,3-pentafluoro-1 -propyl, 2,2,2-trifluoro-1 -ethyl,
2,2,3,3,4,4,5,5-octafluoro-1 -pentyl, or 1 ,1 ,1 ,3,3,3-hexafluoro-2-propyl, to form a lubricant-solvent combination; contacting the combination of lubricant-solvent with the surface; and evaporating the solvent from the surface to form a fluorolubricant coating on the surface
The most advanced, highest recording densities and lowest cost method of storing digital information involves writing and reading magnetic flux patterns from rotating disks coated with magnetic materials. A magnetic layer, where information is stored in the form of bits, is sputtered onto a metallic support structure. Next an overcoat, usually a carbon- based material, is placed on top of the magnetic layer for protection and finally a lubricant is applied to the overcoat. A read-write head flies above the lubricant and the information is exchanged between the head and the magnetic layer. In a relentless attempt to increase the efficiency of
information transfer, hard drive manufacturers have reduced the distance between the head and the magnetic layer, or fly-height, to less than 100 Angstroms.
Invariably, during normal disk drive application, the head and the disk surface will make contact. To reduce wear on the disk, from both sliding and flying contacts, it must be lubricated.
Fluorolubricants are widely used as lubricants in the magnetic disk drive industry to decrease the friction between the head and disk, that is, reduce the wear and therefore minimize the possibility of disk failure.
There is a need in the industry for improved methods for deposition of fluorolubricants. The use of certain solvents, such as CFC-1 13 and PFC-5060, has been regulated due to their impact on the environment. Therefore, solvents that will be used in this application should consider environmental impact. Also, such solvent must dissolve the fluorolubricant and form a substantially uniform or uniform coating of fluorolubricant.
Additionally, existing solvents have been found to require higher fluorolubricant concentrations to produce a given thickness coating and produce irregularities in uniformity of the fluorolubricant coating.
In one embodiment, the fluorolubricants of the present disclosure comprise perfluoropolyether (PFPE) compounds, or lubricant comprising X-1 P®, which is a phosphazene-containing disk lubricant. These perfluoropolyether compounds are sometimes referred to as
perfluoroalkylethers (PFAE) or perfluoropolyalkylethers (PFPAE). These PFPE compounds range from simple perfluorinated ether polymers to functionalized perfluorinated ether polymers. PFPE compounds of different varieties that may be useful as fluorolubricant in the present invention are available from several sources. In another embodiment, useful
fluorolubricants for the present inventive method include but are not limited to Krytox® GLP 100, GLP 105 or GLP 160 (E. I. du Pont de Nemours & Co., Fluoroproducts, Wilmington, DE, 19898, USA); Fomblin® Z-Dol 2000, 2500 or 4000, Z-Tetraol, or Fomblin® AM 2001 or AM 3001 (sold by Solvay Solexis S.p.A., Milan, Italy); Demnum™ LR-200 or S-65 (offered by Daikin America, Inc., Osaka, Japan); X-1 P® (a partially fluorinated hyxaphenoxy cyclotriphosphazene disk lubricant available from Quixtor
Technologies Corporation, a subsidiary of Dow Chemical Co, Midland, Ml); and mixtures thereof. The Krytox® lubricants are
perfluoroalkylpolyethers having the general structure F(CF(CF3)CF2O)n- CF2CF3, wherein n ranges from 10 to 60. The Fomblin® lubricants are functionalized perfluoropolyethers that range in molecular weight from 500 to 4000 atomic mass units and have general formula X-CF2-O(CF2-CF2- O)p-(CF2O)q-CF2-X, wherein X may be -CH2OH, CH2(O-CH2-CH2)nOH, CH2OCH2CH(OH)CH2OH or -CH2O-CH2-piperonyl. The Demnum™ oils are perfluoropolyether-based oils ranging in molecular weight from 2700 to 8400 atomic mass units. Additionally, new lubricants are being developed such as those from Moresco (Thailand) Co., Ltd, which may be useful in the present inventive method.
The fluorolubricants of the present invention may additionally comprise additives to improve the properties of the fluorolubricant. X-1 P®, which may serve as the lubricant itself, is often added to other lower cost fluorolubricants in order to increase the durability of disk drives by passivating Lewis acid sites on the disk surface responsible for PFPE degradation.
Other common lubricant additives may be used in the
fluorolubricants of the present inventive methods.
The fluorolubricants of the present invention may further comprise Z-DPA (Hitachi Global Storage Technologies, San Jose, CA), a PFPE terminated with dialkylamine end-groups. The nucleophilic end-groups serve the same purpose as X1 P®, thus providing the same stability without any additive.
The surface on which the fluorolubricant may be deposited is any solid surface that may benefit from lubrication. Semiconductor materials such as silica disks, metal or metal oxide surfaces, vapor deposited carbon surfaces or glass surfaces are representative of the types of surfaces for which the methods of the present invention are useful. The present inventive method is particularly useful in coating magnetic media such as computer drive hard disks. In the manufacture of computer disks, the surface may be a glass, or aluminum substrate with layers of magnetic media that is also coated by vapor deposition with a thin (10-50 Angstrom)
layer of amorphous hydrogenated or nitrogenated carbon. The
fluorolubricant may be deposited on the surface disk indirectly by applying the fluorolubricant to the carbon layer of the disk.
The first step of combining the fluorolubricant and solvent may be accomplished in any suitable manner such as mixing in a suitable container such as a beaker or other container that may be used as a bath for the deposition method. The fluorolubricant concentration in the unsaturated fluorinated ether solvent may be from about 0.010 percent (wt/wt) to about 0.50 percent (wt/wt).
The step of contacting said combination of fluorolubricant and solvent with the surface may be accomplished in any manner appropriate for said surface (considering the size and shape of the surface). A hard drive disk must be supported in some manner such as with a mandrel or some other support that may fit through the hole in the center of the disk. The disk will thus be held vertically such that the plane of the disk is perpendicular to the solvent bath. The mandrel may have different shapes including but not limited to, a cylindrical bar, or a V-shaped bar. The mandrel shape will determine the area of contact with the disk. The mandrel may be constructed of any material strong enough to hold the disk, including but not limited to metal, metal alloy, plastic or glass.
Additionally, a disk may be supported vertically upright in a woven basket or be clamped into a vertical position with 1 or more clamps on the outer edge. The support may be constructed of any material with the strength to hold the disk, such as metal, metal alloy, plastic or glass. However the disk is supported, the disk will be lowered into a container holding a bath of the fluorolubricant/solvent combination. The bath may be held at room temperature or be heated or cooled to temperatures ranging from about 0°C to about 50°C.
Alternatively, the disk may be supported as described above and the bath may be raised to immerse the disk. In either case, the disk may then be removed from the bath (either by lowering the bath or by raising the disk). Excess fluorolubricant/solvent combination can be drained into the bath.
Either of the methods for contacting the fluorolubricant solvent combination with the disk surface of either lowering the disk into a bath or raising a bath to immerse the disk are commonly referred to as dip coating. Other methods for contacting the disk with the
fluorolubricant/solvent combination may be used in the present inventive method, including spraying or spin coating.
When the disk is removed from the bath, the disk will have a coating of fluorolubricant and some residual solvent (unsaturated fluorinated ether) on its surface. The residual solvent may be evaporated. Evaporation is usually performed at room temperature. However, other temperatures both above and below room temperature may be used as well for the evaporation step. Temperatures ranging from about 0 °C to about 100 °C may be used for evaporation.
The surface, or the disk if the surface is a disk, after completion of the coating method, will be left with a substantially uniform or uniform coating of fluorolubricant that is substantially free of solvent. The fluorolubricant may be applied to a thickness of less than about 300 nm, and alternately to a thickness of about 100 to about 300 nm.
A uniform fluorolubricant coating is desired for proper functioning of a disk and so areas of varying fluorolubricant thickness are undesirable on the surface of the disk. As more and more information is being stored on the same size disk, the read/write head must get closer and closer to the disk in order to function properly. If irregularities due to variation in coating thickness are present on the surface of the disk, the probability of contact of the head with these areas on the disk is much greater. While there is a desire to have enough fluorolubricant on the disk to flow into areas where it may be removed by head contact or other means, coating that is too thick may cause "smear," a problem associated with the read/write head picking up excess fluorolubricant.
One specific coating thickness irregularity observed in the industry is that known as the "rabbit ears" effect. These irregularities are visually detected on the surface of the disk after deposition of the fluorolubricant using the existing solvent systems. When the disk is contacted with the
solution of fluorolubhcant in solvent and then removed from the solution, any points where the solution may accumulate and not drain readily develop drops of solution that do not readily drain off. One such point of drop formation is the contact point (or points) with the mandrel or other support device with the disk. When a V-shaped mandrel is used, there are two contact points at which the mandrel contacts the inside edge of the disk. When solution of fluorolubricant forms drops in these locations that do not drain off when removed from the bath, an area of greater thickness of fluorolubricant is created when the solvent evaporates. The two points of contact with the disk produces what is known as a "rabbit ears" effect, because the areas of greater fluorolubricant thickness produce a pattern resembling rabbit ears visually detectable on the disk surface.
When dip coating is used for depositing fluorolubricant on the surface, the pulling-up speed (speed at which the disk is removed from the bath), and the density of the fluorolubricant and the surface tension are relevant for determining the resulting film thickness of the fluorolubricant. Awareness of these parameters for obtaining the desired film thickness is required. Details on how these parameters effect coatings are given in, "Dip-Coating of Ultra-Thin Liquid Lubricant and its Control for Thin-Film Magnetic Hard Disks" in IEEE Transactions on Magnetics, vol. 31 , no. 6, November 1995.
As used herein, the terms "comprises," "comprising," "includes," "including," "has," "having" or any other variation thereof, are intended to cover a non-exclusive inclusion. For example, a process, method, article, or apparatus that comprises a list of elements is not necessarily limited to only those elements but may include other elements not expressly listed or inherent to such process, method, article, or apparatus. Further, unless expressly stated to the contrary, "or" refers to an inclusive or and not to an exclusive or. For example, a condition A or B is satisfied by any one of the following: A is true (or present) and B is false (or not present), A is false (or not present) and B is true (or present), and both A and B are true (or present).
Also, use of "a" or "an" are employed to describe elements and components described herein. This is done merely for convenience and to give a general sense of the scope of the invention. This description should be read to include one or at least one and the singular also includes the plural unless it is obvious that it is meant otherwise.
Group numbers corresponding to columns within the Periodic Table of the elements use the "New Notation" convention as seen in the CRC Handbook of Chemistry and Physics, 81 st Edition (2000-2001 ).
Unless otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs. Although methods and materials similar or equivalent to those described herein can be used in the practice or testing of embodiments of the present invention, suitable methods and materials are described below. All publications, patent applications, patents, and other references mentioned herein are incorporated by reference in their entirety, unless a particular passage is cited. In case of conflict, the present specification, including definitions, will control. In addition, the materials, methods, and examples are illustrative only and not intended to be limiting.
EXAMPLES
The concepts described herein will be further described in the following examples, which do not limit the scope of the invention
described in the claims.
Example 1
Example 1 demonstrates the reaction of 2,2,3,3-tetrafluoropropanol with perfluorooct-2-ene.
A 1 -L, 3-neck round-bottom (RB) flask was set up with overhead mechanical stirring, heating mantle, reflux condenser, Claisen adapter with thermocouple and a 250-mL pressure-equalizing addition funnel.
Perfluorooct-2-ene (F-2-octene) was analyzed by GC with mass spectral (MS) detection and was found to be 99.5% octene isomers - 92.0% F-2- octene and 0.5% of a C6F13H isomer. To the RB flask, 260.7 g (0.652 mol) of F-octene isomers, 94.7 g (0.717 mol) of 2,2,3,3-tetrafluoropropanol (TFP), and about 1 g of Aliquat® 336 was added. With 300-rpm stirring, the TFP appeared to partially dissolve into the F-2-octene. Next, to the RB flask, 73.2 g (0.587 mol) of 45% KOH was slowly added, with stirring, over a one-hour period. The exothermic reaction increased the
temperature up to about 60°C. External heating was subsequently applied to increase the temperature to approximately 95°C for three hours. The reaction was allowed to cool to ambient conditions, with stirring, overnight.
The crude product was decanted in a separatory funnel, dried over magnesium sulfate, and filtered through polypropylene filter cloth. The crude product (316.9 g) was distilled with a spinning band distillation column at 100 mm Hg. A first fraction (52.2 g fraction) boiling at 34°C-(37- 39)°C was mostly F-2-octene. An about 2 g intermediate fraction at 90°C- 98°C was obtained. A major fraction boiling at 99°C - (102 - 1 10)°C was obtained and weighed 195.3 g. A small sample of the main fraction was heated to reflux at atmospheric pressure in a small RB flask with condenser and the boiling point was 164.5°C. GC/MS analysis indicated that the major fraction was a mixture of at least 9 measurable
components. Four components were greater than 1 % in relative
concentration. Most components had a mass spectral ion (m-19) at 493 Daltons that was indicative of 2,2,3,3-tetrafluoropropyl perfluorooctene ethers. 1 H and 19F NMR was used to help identify the major unsaturated and saturated components. Identified components were consistent with: (3E)-1 ,1 ,1 ,2,3,4,5,5,6,6,7,7,8,8,8-pentadecafluoro-2-(2,2,3,3- tetrafluoropropoxy) oct-3-ene (50%); (2E)-1 ,1 ,1 ,3,4,4,5,5,6,6,7,7,8,8,8- pentadecafluoro-2-(2,2,3,3-tetrafluoropropoxy)oct-2-ene (31 %); (2Z)- 1 ,1 ,1 ,3,4,4,5,5,6,6,7,7,8,8,8-pentadecafluoro-2-(2,2,3,3- tetrafluoropropoxy)oct-2-ene (9%), 1 ,1 ,1 ,2,2,3,3,4,4,5,5,6,8,8,8- pentadecafluoro-7-(2,2,3,3-tetrafluoropropoxy)octane (7 %).
Example 2
Example 2 demonstrates the reaction of 2,2,3,3-tetrafluoropropanol with perfluorooct-2-ene.
A 3-L, 3-neck, Wharton RB flask was set up with overhead mechanical stirring, reflux condenser, heating mantle, Claisen adapter with thermocouple and 250-mL pressure-equalizing addition funnel.
Perfluorooct-2-ene (F-2-octene) was analyzed by GC with mass spectral (MS) detection and was found to be 99.1 % octene isomers - 77.1 % F-2- octene and 0.8% of a C6F13H isomer. To the Wharton flask, 601 .4 g (1 .50- moles) of F-octene isomers, 179 g (1 .36 moles, 0.91 -equiv) of TFP, and about 5-g of Aliquat® 336 was added. With a 300-RPM stirring, the TFP appeared to partially dissolve into the octane mixture. Heating was applied to increase the temperature to approximately 60°C. At that point, 188 g (1 .51 moles) of 45% KOH was slowly added with stirring over a one hour period. The reaction was exothermic and the temperature increased up to about 95°C. After the KOH addition was completed, the reaction was maintained between 75°C and 85°C for an additional 3-hour period. Heating was discontinued and the reaction cooled to ambient conditions with stirring overnight. The crude product was decanted in a separatory funnel, dried over magnesium sulfate, and filtered through polypropylene filter cloth. The crude product weighed 700 g and the aqueous layer weighed 224 g.
The crude product was distilled at 100-mnn Hg using an 18" 1 " ID vacuum jacketed and silvered column, that was packed with Hastelloy® helices, and a high reflux ratio still head with magnetic take-off valve (reflux ratio = 20:2). A first fraction (94.7 g) boiling at 41 .5°C-(42-45)°C was mostly F-2-octene isomers (33.1 g of mostly F-2-octene was subsequently recovered in the dry ice trap). A major fraction boiling at 99°C - (101 - 1 10)°C was obtained and weighed 456.9 g. The distillation heel weighed 107.9 g. GC/MS analysis indicated that the major fraction was a mixture of at least 12 measurable components. Seven components were equal to or greater than 1 % in relative concentration. Most components had a mass spectral ion (m-19) at 493 Daltons that was indicative of 2,2,3,3-tetrafluoropropyl perfluorooctene ethers. 1 H and 19F NMR was used to help identify the major unsaturated and saturated components. Identified components were consistent with: (3E)- 1 ,1 ,1 ,2,3,4,5,5,6,6,7,7,8,8,8-pentadecafluoro-2-methoxyoct-3-ene (50%), (2E)-1 ,1 ,1 ,3,4,4,5,5,6,6,7,7,8,8,8-pentadecafluoro-2-(2,2,3,3- tetrafluoropropoxy)oct-2-ene (34%); (2Z)-1 ,1 ,1 ,3,4,4,5,5,6,6,7,7,8,8,8- pentadecafluoro-2-(2,2,3,3-tetrafluoropropoxy)oct-2-ene (6%); (3E)- 1 ,1 ,1 ,2,2,4,5,5,6,6,7,7,8,8,8-pentadecafluoro-3-(2,2,3,3- tetrafluoropropoxy)oct-3-ene (5%), (3E)-1 ,1 ,1 ,2,2,3,5,5,6,6,7,7,8,8,8- pentadecafluoro-4-(2,2,3,3-tetrafluoropropoxy)oct-3-ene (2%); (1 E)- 1 ,2,3,3,4,4,5,5,6,6,7,7,8,8,8-pentadecafluoro-1 -(2,2,3,3- tetrafluoropropoxy)oct-1 -ene (1 %), 1 ,1 ,1 ,2,2,3,3,4,4,5,5,6,8,8,8- pentadecafluoro-7-(2,2,3,3-tetrafluoropropoxy)octane (1 %).
Example 3
A solvent for depositing a fluorolubricant comprises about 45% CF3CF2CF=CFCF(OCH3)CF2CF3, 25% CF3CF2C(OCH3)=CFCF2CF2CF3 and CF3CF2CF=C(OCH3)CF2CF2CF3, 15%
CF3CF=CFCF(OCH3)CF2CF2CF3 and 15%
CF3CF2CF(OCH3)CFHCF2CF2CF3. This mixture is referred to as Solvent #1 .
The ability of Solvent #1 to dissolve a fluorinated oil is determined by adding an amount of the oil to the solvent until the mixture became
turbid or split into two phases. The results in Table 1 show that Solvent #1 has an excellent ability to dissolve the fluorinated oil. In addition, a solution of 0.5 wt % of the oil is prepared. Pre-weighed metal coupons are dipped into the solution, the solvent evaporated, and the coupon is re- weighed. Table 2 shows the average coating obtained by this dip coating process. Reported coatings weights are the average of three samples. Thus, Solvent #1 can be used as carrier fluid for the deposition of the fluorinated oil onto a substrate.
Example 4
A cleaning solvent comprises about 40%
CF3CF2CF=CFCF(OCH2CH3)CF2CF3, 35%
CF3CF2C(OCH2CH3)=CFCF2CF2CF3 and
CF3CF2CF=C(OCH2CH3)CF2CF2CF3, 18%
CF3CF=CFCF(OCH2CH3)CF2CF2CF3 and 7 %
CF3CF2CF(OCH2CH3)CFHCF2CF2CF3. This mixture is referred to as Solvent #2.
The ability of Solvent #2 to clean a fluorinated oil off a substrate is determined by preparing metal coupons that are coated in Krytox GPL 106 oil and then cleaning the coupons. After coating the coupon with oil, the coupon is immersed into Solvent #2 at a temperature of about 120 C for 5 minutes. The weights of the coupon before and after cleaning are measured and the % oil removed is calculated. Results in Table 3 indicate the ability of the solvent to remove the oil and therefore the solvent would be an effective cleaning agent.
Table 3
Example 5
The ability of 2,2,3, 3-tetrafluoropropyl perfluorooctene ether (FPPOE) to dissolve a fluorinated oil is determined by adding increasing amounts of the oil to the FPPOE until the mixture becomes turbid or splits into two phases. The test shows the oil is miscible in all proportions in the solvent and no turbidity is observed. This is shown in Table 4. In addition, a solution of 5 wt % of the oil is prepared in the FPPOE. Pre- weighed metal coupons with a surface area of 38.7 cm2 are dipped into the solution, the solvent evaporated, and the coupon re-weighed. Table 3 shows the average of 3 coatings obtained by this dip coating process. Thus, FPPOE can be used as a carrier fluid for the deposition of the fluorinated oil onto a substrate.
Example 6
The ability of 2, 2, 3, 3-tetrafluoropropyl perfluoroheptene ether (FPPHE) to dissolve a fluorinated oil is determined by adding increasing amounts of the oil to the FPPHE until the mixture becomes turbid or splits into two phases. The test shows the oil is miscible in all proportions in the solvent and no turbidity is observed. This is shown in Table 5. In addition, a solution of 5 wt % of the oil is prepared in the FPPHE. Pre- weighed metal coupons with a surface area of 38.7 cm2 are dipped into the solution, the solvent evaporated, and the coupon re-weighed. Table 3 shows the average of 3 coatings obtained by this dip coating process.
Thus, FPPHE can be used as a carrier fluid for the deposition of the fluorinated oil onto a substrate.
Metal cleaning with FPPHE or FPPOE
Krytox GPL 106 Oil is wiped onto a clean metal coupon, of known weight, with a swab. The weight of the coupon is recorded, and then the coupon was cleaned by immersion into FPPHE or FPPOE at the room temperature. The coupon is immersed for 1 minute then air dried. The coupon is then reweighed and the percent of oil removed was determined.
These results in Table 6 show that the solvent has excellent efficiency in cleaning fluorinated oils.
Table 6
Note that not all of the activities described above in the general description or the examples are required, that a portion of a specific activity may not be required, and that one or more further activities may be performed in addition to those described. Still further, the order in which activities are listed are not necessarily the order in which they are performed.
In the foregoing specification, the concepts have been described with reference to specific embodiments. However, one of ordinary skill in the art appreciates that various modifications and changes can be made without departing from the scope of the invention as set forth in the claims below. Accordingly, the specification and figures are to be regarded in an illustrative rather than a restrictive sense, and all such modifications are intended to be included within the scope of invention.
Benefits, other advantages, and solutions to problems have been described above with regard to specific embodiments. However, the benefits, advantages, solutions to problems, and any feature(s) that may cause any benefit, advantage, or solution to occur or become more pronounced are not to be construed as a critical, required, or essential feature of any or all the claims.
It is to be appreciated that certain features are, for clarity, described herein in the context of separate embodiments, may also be provided in combination in a single embodiment. Conversely, various features that are, for brevity, described in the context of a single embodiment, may also be provided separately or in any subcombination. Further, reference to values stated in ranges include each and every value within that range.
Claims
What is claimed is:
1 . A composition comprising at least one unsaturated fluoroalkyi perfluoroalkene ether having a formula selected from the group consisting of CF3(CF2)xCF=CFCF(OR)(CF2)yCF3,
CF3(CF2)xC(OR)=CFCF2(CF2)yCF3,
CF3CF=CFCF(OR)(CF2)x(CF2)yCF3,
CF3(CF2)xCF=C(OR)CF2(CF2)yCF3, and mixtures thereof;
wherein x and y are independently 0, 1 , 2, 3 or 4 and wherein x + y = 0, 1 , 2, 3 or 4; and
wherein R is 2,2,3,3-tetrafluoro-1 -propyl, 2,2,3,3,3-pentafluoro-1 - propyl, 2,2,2-trifluoro-1 -ethyl, 2, 2, 3,3,4,4,5, 5-octafluoro-1 -pentyl, or
1 ,1 ,1 ,3,3,3-hexafluoro-2-propyl.
The composition of Claim 1 , wherein said unsaturated fluoroalkyi perfluoroalkene ether comprises a compound having the formula CF3(CF2)xCF=CFCF(OR)(CF2)yCF3.
3. The composition of Claim 2, further comprising a compound having the formula CF3(CF2)xC(OR)=CFCF2(CF2)yCF3.
4. The composition of Claim 1 , wherein said unsaturated fluoroalkyi perfluoroalkene ether comprises a compound having the formula CF3(CF2)xC(OR)=CFCF2(CF2)yCF3.
5. The composition of Claim 1 , wherein said unsaturated fluoroalkyi perfluoroalkene ether comprises a compound having the formula CF3CF=CFCF(OR)(CF2)x(CF2)yCF3.
The composition of Claim 1 , wherein said unsaturated fluoroalkyi perfluoroalkene ether comprises a compound having the formula CF3(CF2)xCF=C(OR)CF2(CF2)yCF3.
A process for preparation of unsaturated fluoroalkyi perfluoroalkene ethers comprising:
(a) contacting a peril uoropentene, peril uorohexene,
perfluoroheptene, perfluorooctene or perfluorononene with a fluorinated alcohol, and a strong base, in an aqueous solution, to provide an unsaturated fluoroalkyi perfluoroalkene ether layer and an aqueous layer, wherein said fluorinated alcohol is defined by the formula R-OH, wherein R is 2,2,3,3-tetrafluoro-1 -propyl, 2,2,3,3,3- pentafluoro-1 -propyl, 2,2,2-trifluoro-1 -ethyl, 2,2,3,3,4,4,5,5- octafluoro-1 -pentyl, or 1 ,1 ,1 ,3,3,3-hexafluoro-2-propyl; and
(b) separating said unsaturated alkyl perfluoroalkene ether layer from said aqueous layer to provide said unsaturated fluoroalkyi perfluoroalkene ether product.
The process of Claim 7, wherein the contacting step further comprises a phase transfer catalyst.
The process of Claim 8, wherein the phase transfer catalyst is selected from the group consisting of crown ethers, onium salts, cryptates and polyalkylene glycols and derivatives thereof, and mixtures thereof.
The process of Claim 9, wherein said strong base is a base which will react with an alcohol to produce an alkoxide upon combination of the base with said fluorinated alcohol.
The process of Claim 7, wherein said strong base is an alkali metal hydroxide.
12. The process of Claim 7, wherein said perfluoropentene,
perfluorohexene, perfluoroheptene, perfluorooctene or
perfluorononene is selected from the group consisting of perfluoro- 2-pentene, perfluoro-2-hexene, perfluoro-3-hexene, perfluoro-2- heptene, perfluoro-3-heptene, perfluoro-2-octene, perfluoro-3- octene, perfluoro-4-octene, perfluoro-2-nonene, perfluoro-3-nonene or perfluoro-4-nonene.
A method for removing residue from a surface of an article, said method comprising:
a. contacting said surface with a composition comprising at least one unsaturated alkyl perfluoroalkene ether having a formula selected from the group consisting of
CF3(CF2)xCF=CFCF(OR)(CF2)yCF3j
CF3(CF2)xC(OR)=CFCF2(CF2)yCF3,
CF3CF=CFCF(OR)(CF2)x(CF2)yCF3j
CF3(CF2)xCF=C(OR)CF2(CF2)yCF3, and mixtures thereof; wherein x and y are independently 0, 1 , 2, 3 or 4 and wherein x + y = 0, 1 , 2, 3 or 4; and
wherein R is 2,2,3,3-tetrafluoro-1 -propyl, 2,2,3,3,3- pentafluoro-1 -propyl, 2,2,2-trifluoro-1 -ethyl, 2,2,3,3,4,4,5,5- octafluoro-1 -pentyl, or 1 ,1 ,1 ,3,3,3-hexafluoro-2-propyl; and b. recovering said surface from said composition.
The method of Claim 13, wherein said composition further comprises a propellant.
The method of Claim 14, wherein said propellant is selected from the group consisting of air, nitrogen, carbon dioxide,
difluoromethane (CF2H2, HFC-32), trifluoromethane (CF3H, HFC- 23), difluoroethane (CHF2CH3, HFC-152a), trifluoroethane (CH3CF3 HFC-143a; or CHF2CH2F, HFC-143), tetrafluoroethane (CF3CH2F, HFC-134a; or CF2HCF2H, HFC-134), pentafluoroethane (CF3CF2H, HFC-125), 1 ,3,3,3-tetrafluoro-1 -propene (HFO-1234ze), 2,3,3,3- tetrafluoro-1 -propene (HFO-1234yf), 1 ,2,3,3,3-pentafluoropropene
(HFO-1225ye), 1 ,1 ,3,3,3-pentafluoropropene (HFO-1225ze), hydrocarbons, and dimethyl ether.
The method of Claim 13, wherein said composition further comprises at least one surfactant.
The method of Claim 13, wherein said contacting is accomplished by vapor degreasing.
The method of Claim 17, wherein said vapor degreasing is performed by:
a. boiling the composition; and
b. exposing said article to vapors of the boiling cleaning
composition.
The method of Claim 13, wherein said contacting is accomplished by immersing said article in said composition, wherein said composition is at a temperature greater than ambient or room temperature.
A method for depositing a fluorolubricant on a surface comprising: a. combining a fluorolubricant and a solvent, said solvent comprising at least one unsaturated alkyl perfluoroalkene ether having a formula selected from the group consisting of
CF3(CF2)xCF=CFCF(OR)(CF2)yCF3,
CF3(CF2)xC(OR)=CFCF2(CF2)yCF3,
CF3CF=CFCF(OR)(CF2)x(CF2)yCF3,
CF3(CF2)xCF=C(OR)CF2(CF2)yCF3, and mixtures thereof; wherein x and y are independently 0, 1 , 2, 3 or 4 and wherein x + y = 0, 1 , 2, 3 or 4; and
wherein R is 2,2,3,3-tetrafluoro-1 -propyl, 2,2,3,3,3- pentafluoro-1 -propyl, 2,2,2-trifluoro-1 -ethyl, 2,2,3,3,4,4,5,5- octafluoro-1 -pentyl, or 1 ,1 ,1 ,3,3,3-hexafluoro-2-propyl;
to form a lubricant-solvent combination;
b. contacting said combination of lubricant-solvent with said surface; and
c. evaporating said solvent from said surface to form a
fluorolubricant coating on said surface.
21 . The method of Claim 20, wherein said surface is that of a
semiconductor material, metal, metal oxide, vapor deposited carbon, or glass. 22. The method of Claim 21 , wherein said surface is that of a magnetic medium.
23. The method of Claim 22, wherein said magnetic medium is a
computer disk.
24. The method of Claim 22, wherein the contacting step is
accomplished by dipping or immersing said surface in a bath comprising said fluorolubricant. 25. The method of Claim 20, wherein said contacting step is
accomplished by spraying or spin coating said surface with the fluorolubricant.
26. The method of Claim 20, wherein said fluorolubricant concentration in said lubricant-solvent combination is from about 0.02 weight percent to about 0.5 weight percent.
27. The method of Claim 20, wherein said evaporating step is
accomplished at a temperature of from about 10°C to about 40°C.
28. The method of Claim 20, wherein said fluorolubricant comprises a perfluoropolyether.
29. The method of Claim 20, wherein said fluorolubricant is selected from the group consisting of perfluoropolyethers and mixtures thereof. 30. A process for transferring heat comprising transferring heat
between a heat source and a heat sink through the use of a heat transfer agent comprising at least one unsaturated alkyl
perfluoroalkene ether having a formula selected from the group consisting of CF3(CF2)xCF=CFCF(OR)(CF2)yCF3,
CF3(CF2)xC(OR)=CFCF2(CF2)yCF3,
CF3CF=CFCF(OR)(CF2)x(CF2)yCF3,
CF3(CF2)xCF=C(OR)CF2(CF2)yCF3, and mixtures thereof;
wherein x and y are independently 0, 1 , 2, 3 or 4 and wherein x + y = 0, 1 , 2, 3 or 4; and
wherein R is 2,2,3,3-tetrafluoro-1 -propyl, 2,2,3, 3,3-pentafluoro-1 - propyl, 2,2,2-trifluoro-1 -ethyl, 2, 2, 3,3,4,4,5, 5-octafluoro-1 -pentyl, or 1 ,1 ,1 ,3,3,3-hexafluoro-2-propyl.
31 . The process of Claim 30, wherein said unsaturated alkyl
perfluoroalkene ether comprises a compound having the formula
CF3(CF2)xCF=CFCF(OR)(CF2)yCF3.
32. The process of Claim 31 , further comprising a compound having the formula CF3(CF2)xC(OR)=CFCF2(CF2)yCF3.
33. The process of Claim 30, wherein said unsaturated alkyl
perfluoroalkene ether comprises a compound having the formula CF3(CF2)xC(OR)=CFCF2(CF2)yCF3. 34. The process of Claim 30, wherein said unsaturated alkyl
perfluoroalkene ether comprises a compound having the formula CF3CF=CFCF(OR)(CF2)x(CF2)yCF3.
35. The process of Clainn 30, wherein said unsaturated alkyl perfluoroalkene ether comprises a compound having the formula CF3(CF2)xCF=C(OR)CF2(CF2)yCF3.
The process of Claim 30, comprising providing said composition a liquid phase and evaporating said liquid phase by transferring heat from said heat source to said heat sink.
The process of Claim 30, comprising providing said composition vapor phase and thereafter condensing said vapor phase by transferring heat from said heat source to said heat sink.
An improved heat transfer system comprising at least one heat transfer fluid and one or more vessels for evaporating and condensing said heat transfer fluid, the improvement characterized by said heat transfer fluid being at least one unsaturated alkyl perfluoroalkene ether having a formula selected from the group consisting of CF3(CF2)xCF=CFCF(OR)(CF2)yCF3,
CF3(CF2)xC(OR)=CFCF2(CF2)yCF3,
CF3CF=CFCF(OR)(CF2)x(CF2)yCF3,
CF3(CF2)xCF=C(OR)CF2(CF2)yCF3, and mixtures thereof;
wherein x and y are independently 0, 1 , 2, 3 or 4 and wherein x + y = 0, 1 , 2, 3 or 4; and wherein R is 2,2,3,3-tetrafluoro-1 -propyl, 2,2,3,3,3-pentafluoro-1 -propyl, 2,2,2-trifluoro-1 -ethyl,
2,2,3,3,4,4,5,5-octafluoro-1 -pentyl, or 1 ,1 ,1 ,3,3,3-hexafluoro-2- propyl.
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