TW200538509A - Fluoropolyether compound - Google Patents
Fluoropolyether compound Download PDFInfo
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- TW200538509A TW200538509A TW094101015A TW94101015A TW200538509A TW 200538509 A TW200538509 A TW 200538509A TW 094101015 A TW094101015 A TW 094101015A TW 94101015 A TW94101015 A TW 94101015A TW 200538509 A TW200538509 A TW 200538509A
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 288
- 239000000314 lubricant Substances 0.000 claims abstract description 16
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 14
- 239000003607 modifier Substances 0.000 claims abstract description 10
- 239000004094 surface-active agent Substances 0.000 claims abstract description 10
- 229930195734 saturated hydrocarbon Natural products 0.000 claims abstract description 7
- IUHFWCGCSVTMPG-UHFFFAOYSA-N [C].[C] Chemical group [C].[C] IUHFWCGCSVTMPG-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 29
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 27
- 239000011737 fluorine Substances 0.000 claims description 27
- 239000000203 mixture Substances 0.000 claims description 27
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 23
- 229920000570 polyether Polymers 0.000 claims description 23
- 239000000126 substance Substances 0.000 claims description 9
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 238000009826 distribution Methods 0.000 claims description 7
- 238000005227 gel permeation chromatography Methods 0.000 claims description 6
- -1 perfluoro Chemical group 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 2
- 230000037431 insertion Effects 0.000 claims 1
- 238000003780 insertion Methods 0.000 claims 1
- 230000006866 deterioration Effects 0.000 abstract description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract description 2
- 235000019256 formaldehyde Nutrition 0.000 abstract description 2
- 239000002904 solvent Substances 0.000 description 31
- 238000004293 19F NMR spectroscopy Methods 0.000 description 29
- 238000000034 method Methods 0.000 description 26
- 238000005160 1H NMR spectroscopy Methods 0.000 description 21
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 21
- 239000000047 product Substances 0.000 description 21
- 238000005481 NMR spectroscopy Methods 0.000 description 20
- 239000000243 solution Substances 0.000 description 20
- 238000006243 chemical reaction Methods 0.000 description 17
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 15
- 239000010408 film Substances 0.000 description 14
- 238000004519 manufacturing process Methods 0.000 description 14
- 229910052757 nitrogen Inorganic materials 0.000 description 12
- 239000007788 liquid Substances 0.000 description 11
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 10
- 238000000576 coating method Methods 0.000 description 9
- 229910052799 carbon Inorganic materials 0.000 description 8
- 239000011248 coating agent Substances 0.000 description 8
- 229920000642 polymer Polymers 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
- 101150041968 CDC13 gene Proteins 0.000 description 6
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 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 6
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical group O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 description 6
- 239000000758 substrate Substances 0.000 description 6
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 5
- KWIUHFFTVRNATP-UHFFFAOYSA-O N,N,N-trimethylglycinium Chemical compound C[N+](C)(C)CC(O)=O KWIUHFFTVRNATP-UHFFFAOYSA-O 0.000 description 5
- 238000007259 addition reaction Methods 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 5
- 125000001153 fluoro group Chemical group F* 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- 150000002430 hydrocarbons Chemical group 0.000 description 5
- 230000009467 reduction Effects 0.000 description 5
- 238000005507 spraying Methods 0.000 description 5
- 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 4
- WZFUQSJFWNHZHM-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)CC(=O)N1CC2=C(CC1)NN=N2 WZFUQSJFWNHZHM-UHFFFAOYSA-N 0.000 description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 230000007547 defect Effects 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 239000012535 impurity Substances 0.000 description 4
- 239000012263 liquid product Substances 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 239000010702 perfluoropolyether Substances 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 238000004528 spin coating Methods 0.000 description 4
- 238000013112 stability test Methods 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- XXZCIYUJYUESMD-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-3-(morpholin-4-ylmethyl)pyrazol-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C=1C(=NN(C=1)CC(=O)N1CC2=C(CC1)NN=N2)CN1CCOCC1 XXZCIYUJYUESMD-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 238000003618 dip coating Methods 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 3
- 239000003973 paint Substances 0.000 description 3
- 239000011698 potassium fluoride Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- OHVLMTFVQDZYHP-UHFFFAOYSA-N 1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-2-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]ethanone Chemical compound N1N=NC=2CN(CCC=21)C(CN1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)=O OHVLMTFVQDZYHP-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 238000005266 casting Methods 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 239000007810 chemical reaction solvent Substances 0.000 description 2
- 239000011247 coating layer Substances 0.000 description 2
- 229940125782 compound 2 Drugs 0.000 description 2
- LBJNMUFDOHXDFG-UHFFFAOYSA-N copper;hydrate Chemical compound O.[Cu].[Cu] LBJNMUFDOHXDFG-UHFFFAOYSA-N 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- GPLRAVKSCUXZTP-UHFFFAOYSA-N diglycerol Chemical compound OCC(O)COCC(O)CO GPLRAVKSCUXZTP-UHFFFAOYSA-N 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 239000012454 non-polar solvent Substances 0.000 description 2
- 125000000962 organic group Chemical group 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 238000005191 phase separation Methods 0.000 description 2
- 239000002798 polar solvent Substances 0.000 description 2
- 239000011148 porous material Substances 0.000 description 2
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000012925 reference material Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000004065 semiconductor Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 2
- 238000001771 vacuum deposition Methods 0.000 description 2
- CMVFABYKWZDQMC-UHFFFAOYSA-N 1,1,3,4-tetrachloro-1,2,2,3,4,4-hexafluorobutane Chemical compound FC(F)(Cl)C(F)(Cl)C(F)(F)C(F)(Cl)Cl CMVFABYKWZDQMC-UHFFFAOYSA-N 0.000 description 1
- KQZLRWGGWXJPOS-NLFPWZOASA-N 1-[(1R)-1-(2,4-dichlorophenyl)ethyl]-6-[(4S,5R)-4-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]-5-methylcyclohexen-1-yl]pyrazolo[3,4-b]pyrazine-3-carbonitrile Chemical compound ClC1=C(C=CC(=C1)Cl)[C@@H](C)N1N=C(C=2C1=NC(=CN=2)C1=CC[C@@H]([C@@H](C1)C)N1[C@@H](CCC1)CO)C#N KQZLRWGGWXJPOS-NLFPWZOASA-N 0.000 description 1
- YSIGVPOSKQLNTO-UHFFFAOYSA-N 2,3,3,3-tetrafluoro-2-[1,1,2,3,3,3-hexafluoro-2-(1,1,2,2,3,3,3-heptafluoropropoxy)propoxy]propanoyl fluoride Chemical group FC(=O)C(F)(C(F)(F)F)OC(F)(F)C(F)(C(F)(F)F)OC(F)(F)C(F)(F)C(F)(F)F YSIGVPOSKQLNTO-UHFFFAOYSA-N 0.000 description 1
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
- COAUHYBSXMIJDK-UHFFFAOYSA-N 3,3-dichloro-1,1,1,2,2-pentafluoropropane Chemical compound FC(F)(F)C(F)(F)C(Cl)Cl COAUHYBSXMIJDK-UHFFFAOYSA-N 0.000 description 1
- YLZOPXRUQYQQID-UHFFFAOYSA-N 3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]propan-1-one Chemical compound N1N=NC=2CN(CCC=21)CCC(=O)N1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F YLZOPXRUQYQQID-UHFFFAOYSA-N 0.000 description 1
- KWIUHFFTVRNATP-UHFFFAOYSA-N Betaine Natural products C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 102100030878 Cytochrome c oxidase subunit 1 Human genes 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- 229940123457 Free radical scavenger Drugs 0.000 description 1
- 230000005526 G1 to G0 transition Effects 0.000 description 1
- 101000919849 Homo sapiens Cytochrome c oxidase subunit 1 Proteins 0.000 description 1
- 101000605122 Homo sapiens Prostaglandin G/H synthase 1 Proteins 0.000 description 1
- 108010002350 Interleukin-2 Proteins 0.000 description 1
- 101100109406 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) aga-1 gene Proteins 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 101100273965 Solanum lycopersicum HCR9-0 gene Proteins 0.000 description 1
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- YKTSYUJCYHOUJP-UHFFFAOYSA-N [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] Chemical compound [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] YKTSYUJCYHOUJP-UHFFFAOYSA-N 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
- 239000005456 alcohol based solvent Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
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- 125000000129 anionic group Chemical group 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 238000000149 argon plasma sintering Methods 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 229960003237 betaine Drugs 0.000 description 1
- UWTDFICHZKXYAC-UHFFFAOYSA-N boron;oxolane Chemical compound [B].C1CCOC1 UWTDFICHZKXYAC-UHFFFAOYSA-N 0.000 description 1
- 239000003990 capacitor Substances 0.000 description 1
- OSQPUMRCKZAIOZ-UHFFFAOYSA-N carbon dioxide;ethanol Chemical compound CCO.O=C=O OSQPUMRCKZAIOZ-UHFFFAOYSA-N 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
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- 229910052801 chlorine Inorganic materials 0.000 description 1
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- YQNQTEBHHUSESQ-UHFFFAOYSA-N lithium aluminate Chemical compound [Li+].[O-][Al]=O YQNQTEBHHUSESQ-UHFFFAOYSA-N 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000010687 lubricating oil Substances 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- HCWCAKKEBCNQJP-UHFFFAOYSA-N magnesium orthosilicate Chemical compound [Mg+2].[Mg+2].[O-][Si]([O-])([O-])[O-] HCWCAKKEBCNQJP-UHFFFAOYSA-N 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- 239000000391 magnesium silicate Substances 0.000 description 1
- 229910052919 magnesium silicate Inorganic materials 0.000 description 1
- 235000019792 magnesium silicate Nutrition 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 230000011987 methylation Effects 0.000 description 1
- 238000007069 methylation reaction Methods 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- GVGCUCJTUSOZKP-UHFFFAOYSA-N nitrogen trifluoride Chemical class FN(F)F GVGCUCJTUSOZKP-UHFFFAOYSA-N 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000013307 optical fiber Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 238000010422 painting Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229950008618 perfluamine Drugs 0.000 description 1
- 125000005459 perfluorocyclohexyl group Chemical group 0.000 description 1
- JAJLKEVKNDUJBG-UHFFFAOYSA-N perfluorotripropylamine Chemical compound FC(F)(F)C(F)(F)C(F)(F)N(C(F)(F)C(F)(F)C(F)(F)F)C(F)(F)C(F)(F)C(F)(F)F JAJLKEVKNDUJBG-UHFFFAOYSA-N 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 235000003270 potassium fluoride Nutrition 0.000 description 1
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- 230000003449 preventive effect Effects 0.000 description 1
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- 230000035484 reaction time Effects 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-N sodium;hydron;carbonate Chemical class [Na+].OC(O)=O UIIMBOGNXHQVGW-UHFFFAOYSA-N 0.000 description 1
- 238000005476 soldering Methods 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000000194 supercritical-fluid extraction Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 239000006200 vaporizer Substances 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
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/004—Surface-active compounds containing F
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/321—Polymers modified by chemical after-treatment with inorganic compounds
- C08G65/323—Polymers modified by chemical after-treatment with inorganic compounds containing halogens
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/329—Polymers modified by chemical after-treatment with organic compounds
- C08G65/337—Polymers modified by chemical after-treatment with organic compounds containing other elements
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
- C08L71/02—Polyalkylene oxides
-
- 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
- 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
- C10M107/00—Lubricating compositions characterised by the base-material being a macromolecular compound
- C10M107/38—Lubricating compositions characterised by the base-material being a macromolecular compound containing halogen
-
- 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
- C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
- C10M2211/04—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen, halogen, and oxygen
- C10M2211/0406—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen, halogen, and oxygen used as base material
-
- 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
- C10M2213/04—Organic macromolecular compounds containing halogen as ingredients in lubricant compositions obtained from monomers containing carbon, hydrogen, halogen and oxygen
- C10M2213/043—Organic macromolecular compounds containing halogen as ingredients in lubricant compositions obtained from monomers containing carbon, hydrogen, halogen and oxygen used as base material
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Inorganic Chemistry (AREA)
- Emergency Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polyethers (AREA)
- Lubricants (AREA)
- Paints Or Removers (AREA)
- Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2004005586 | 2004-01-13 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW200538509A true TW200538509A (en) | 2005-12-01 |
| TWI349023B TWI349023B (https=) | 2011-09-21 |
Family
ID=34792108
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW094101015A TW200538509A (en) | 2004-01-13 | 2005-01-13 | Fluoropolyether compound |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US7795375B2 (https=) |
| EP (1) | EP1705203B1 (https=) |
| JP (1) | JP5028801B2 (https=) |
| KR (1) | KR101089078B1 (https=) |
| CN (1) | CN100392000C (https=) |
| AT (1) | ATE432954T1 (https=) |
| DE (1) | DE602005014734D1 (https=) |
| RU (1) | RU2373229C2 (https=) |
| TW (1) | TW200538509A (https=) |
| WO (1) | WO2005068534A1 (https=) |
Families Citing this family (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004035656A1 (ja) * | 2002-10-18 | 2004-04-29 | Asahi Glass Company, Limited | ペルフルオロポリエーテル誘導体 |
| CN1989230B (zh) * | 2004-07-27 | 2010-05-05 | 旭硝子株式会社 | 以含氟聚醚化合物为润滑剂的磁记录媒体用润滑剂溶液 |
| JPWO2007013412A1 (ja) | 2005-07-27 | 2009-02-05 | 旭硝子株式会社 | エーテル組成物および溶液組成物 |
| ITTO20060139A1 (it) * | 2006-02-27 | 2007-08-28 | Bridgestone Corp | Mescola di gomma vulcanizzabile contenente silice |
| JP2008034064A (ja) * | 2006-07-31 | 2008-02-14 | Toshiba Corp | 磁気記録媒体及び磁気記録再生装置 |
| KR20100017848A (ko) | 2007-05-23 | 2010-02-16 | 쓰리엠 이노베이티브 프로퍼티즈 컴파니 | 플루오르화 계면활성제의 수성 조성물 및 그의 사용 방법 |
| JP5453250B2 (ja) | 2007-06-06 | 2014-03-26 | スリーエム イノベイティブ プロパティズ カンパニー | フッ素化エーテル組成物及びフッ素化エーテル組成物の使用方法 |
| JPWO2009008380A1 (ja) * | 2007-07-06 | 2010-09-09 | 旭硝子株式会社 | 表面処理剤、物品、および新規含フッ素エーテル化合物 |
| JP5309622B2 (ja) * | 2007-11-28 | 2013-10-09 | 旭硝子株式会社 | 表面処理剤 |
| KR20100094484A (ko) * | 2007-12-19 | 2010-08-26 | 아사히 가라스 가부시키가이샤 | 에테르 조성물 |
| JP4507263B2 (ja) * | 2008-01-16 | 2010-07-21 | 信越化学工業株式会社 | 含フッ素硬化性組成物 |
| CN101925655B (zh) * | 2008-01-24 | 2012-10-17 | 旭硝子株式会社 | 醚组合物 |
| JP5795457B2 (ja) * | 2008-01-24 | 2015-10-14 | 旭硝子株式会社 | エーテル化合物、潤滑剤、溶媒組成物および磁気ディスクの製造方法 |
| BRPI0915955A2 (pt) | 2008-07-18 | 2019-02-26 | 3M Innovative Proferties Company | compostos fluorados de éter e métodos para uso dos mesmos |
| EP2325157B1 (en) | 2008-09-09 | 2014-11-05 | Asahi Glass Company, Limited | Method for producing a perfluoro compound having hydroxyl groups |
| US8629089B2 (en) | 2008-12-18 | 2014-01-14 | 3M Innovative Properties Company | Method of contacting hydrocarbon-bearing formations with fluorinated ether compositions |
| JP2010168512A (ja) * | 2009-01-26 | 2010-08-05 | Hitachi Ltd | 潤滑剤、および、それを用いた磁気ディスク装置 |
| US8697985B2 (en) | 2009-05-25 | 2014-04-15 | Solvay Solexis, S.PA. | Protective film for a solar cell module |
| JP2012184275A (ja) * | 2009-07-15 | 2012-09-27 | Asahi Glass Co Ltd | エーテル組成物および潤滑剤 |
| KR101729353B1 (ko) | 2009-10-01 | 2017-04-21 | 아사히 가라스 가부시키가이샤 | 가교성 불소 고무 조성물 및 가교 고무 물품 |
| JPWO2011065312A1 (ja) | 2009-11-26 | 2013-04-11 | 旭硝子株式会社 | エーテル化合物、これを含む潤滑剤および潤滑剤用組成物 |
| RU2522640C2 (ru) * | 2012-05-31 | 2014-07-20 | Общество с ограниченной ответственностью Научно Производственный Центр "Квадра" | Фторсодержащее пав и способ его получения |
| WO2014126107A1 (ja) * | 2013-02-13 | 2014-08-21 | 旭硝子株式会社 | 含フッ素エーテル組成物、表面改質剤、界面活性剤、液状組成物、物品 |
| CN105452333B (zh) * | 2013-08-13 | 2017-08-08 | 旭硝子株式会社 | 含氟聚醚化合物、润滑剂、液状组合物以及物品 |
| WO2015025930A1 (ja) * | 2013-08-23 | 2015-02-26 | ダイキン工業株式会社 | パーフルオロ（ポリ）エーテル基含有カルボン酸化合物の分離方法 |
| US20170240839A1 (en) | 2014-08-05 | 2017-08-24 | Solvay Specialty Polymers Italy S.P.A. | Lubrication method with alkoxylated perfluoropolyether |
| WO2016096684A1 (en) | 2014-12-15 | 2016-06-23 | Solvay Specialty Polymers Italy S.P.A. | Water-based composition comprising a fluorinated polymer |
| KR101643364B1 (ko) | 2015-11-11 | 2016-08-26 | 상화시스템주식회사 | 얼터네이터 부품 해체 장치 및 해체 방법 |
| CN106832256B (zh) * | 2017-01-18 | 2020-07-28 | 济南齐氟新材料技术有限公司 | 一种含氟非离子表面活性剂的制备方法 |
| CN109022105B (zh) * | 2018-06-13 | 2021-09-17 | 权家（厦门）新材料有限公司 | 一种水溶性氟碳石墨烯机油及其制备方法 |
| WO2024038866A1 (ja) * | 2022-08-18 | 2024-02-22 | Ａｇｃ株式会社 | 化合物、組成物、表面処理剤、コーティング液、物品、及び物品の製造方法 |
| JP7671014B2 (ja) * | 2023-03-03 | 2025-05-01 | ダイキン工業株式会社 | 含フッ素化合物 |
| JPWO2024225106A1 (https=) * | 2023-04-28 | 2024-10-31 | ||
| JPWO2024225107A1 (https=) * | 2023-04-28 | 2024-10-31 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1007029B (it) * | 1974-01-23 | 1976-10-30 | Montedison Spa | Polimeri elastomerici fluorurati contenenti l anello della 1.3.5.triazina e procedimento per la lo ro preparazione |
| DE2403706A1 (de) | 1974-01-26 | 1975-08-14 | Hoechst Ag | Verfahren zur herstellung von chlorierten kupferphthalocyaninen |
| JP3270469B2 (ja) * | 1991-01-11 | 2002-04-02 | ダイネオン リミティド ライアビリティー カンパニー | 硬化性フルオロカーボンエラストマー |
| US6217984B1 (en) * | 1992-05-21 | 2001-04-17 | 3M Innovative Properties Company | Organometallic monomers and polymers with improved adhesion |
| IT1264139B1 (it) * | 1993-04-19 | 1996-09-16 | Ausimont Spa | Polimeri fluorurati contenenti sequenze perfluoropoliossialchileniche ed aventi proprieta' di elastomeri termoplastici |
| JP2000169481A (ja) * | 1998-12-10 | 2000-06-20 | Toray Ind Inc | 含フッ素化合物及び防汚性物品 |
| JP2001208736A (ja) * | 2000-01-28 | 2001-08-03 | Asahi Glass Co Ltd | フッ素系有機化合物の分子量測定方法 |
| JP3666575B2 (ja) * | 2000-06-29 | 2005-06-29 | 信越化学工業株式会社 | 硬化性フルオロポリエーテルゴム組成物 |
| KR100778262B1 (ko) * | 2000-07-11 | 2007-11-27 | 아사히 가라스 가부시키가이샤 | 불소 함유 화합물의 제조방법 |
| US6753301B2 (en) * | 2000-07-19 | 2004-06-22 | E. I. Du Pont De Nemours And Company | Thermally stable perfluoropolyethers and processes therefor and therewith |
| US6632508B1 (en) * | 2000-10-27 | 2003-10-14 | 3M Innovative Properties Company | Optical elements comprising a polyfluoropolyether surface treatment |
| JP4088773B2 (ja) * | 2001-04-27 | 2008-05-21 | 旭硝子株式会社 | フッ素化されたポリオキシアルキレン化合物の製造方法 |
| JP4387687B2 (ja) | 2002-04-26 | 2009-12-16 | キヤノン株式会社 | 画像処理装置、制御方法、及びプログラム |
| WO2004035656A1 (ja) * | 2002-10-18 | 2004-04-29 | Asahi Glass Company, Limited | ペルフルオロポリエーテル誘導体 |
| EP2163536A1 (en) * | 2003-02-21 | 2010-03-17 | Asahi Glass Company, Limited | Process for production of perfluorodiacyl fluorides |
| JP2004307349A (ja) * | 2003-04-02 | 2004-11-04 | Matsushita Electric Ind Co Ltd | 含フッ素化合物、潤滑剤、ならびに磁気記録媒体および磁気記録媒体の製造方法 |
| US9676603B1 (en) * | 2012-09-05 | 2017-06-13 | Dennis C. Oakley | Multipurpose handheld tool and associated method |
-
2005
- 2005-01-12 CN CNB2005800019115A patent/CN100392000C/zh not_active Expired - Fee Related
- 2005-01-12 KR KR1020067010575A patent/KR101089078B1/ko not_active Expired - Fee Related
- 2005-01-12 JP JP2005517045A patent/JP5028801B2/ja not_active Expired - Fee Related
- 2005-01-12 RU RU2006129281/04A patent/RU2373229C2/ru not_active IP Right Cessation
- 2005-01-12 EP EP05703495A patent/EP1705203B1/en not_active Expired - Lifetime
- 2005-01-12 AT AT05703495T patent/ATE432954T1/de not_active IP Right Cessation
- 2005-01-12 DE DE602005014734T patent/DE602005014734D1/de not_active Expired - Lifetime
- 2005-01-12 WO PCT/JP2005/000256 patent/WO2005068534A1/ja not_active Ceased
- 2005-01-13 TW TW094101015A patent/TW200538509A/zh not_active IP Right Cessation
-
2006
- 2006-07-11 US US11/483,566 patent/US7795375B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| EP1705203A1 (en) | 2006-09-27 |
| RU2373229C2 (ru) | 2009-11-20 |
| RU2006129281A (ru) | 2008-02-20 |
| KR101089078B1 (ko) | 2011-12-05 |
| TWI349023B (https=) | 2011-09-21 |
| JP5028801B2 (ja) | 2012-09-19 |
| US20060252910A1 (en) | 2006-11-09 |
| ATE432954T1 (de) | 2009-06-15 |
| KR20060123221A (ko) | 2006-12-01 |
| JPWO2005068534A1 (ja) | 2007-12-27 |
| EP1705203A4 (en) | 2007-05-02 |
| CN1906228A (zh) | 2007-01-31 |
| CN100392000C (zh) | 2008-06-04 |
| US7795375B2 (en) | 2010-09-14 |
| WO2005068534A1 (ja) | 2005-07-28 |
| DE602005014734D1 (de) | 2009-07-16 |
| EP1705203B1 (en) | 2009-06-03 |
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| MM4A | Annulment or lapse of patent due to non-payment of fees |