JP5513133B2 - ペンダントシリル基を有するフルオロケミカル化合物 - Google Patents
ペンダントシリル基を有するフルオロケミカル化合物 Download PDFInfo
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- JP5513133B2 JP5513133B2 JP2009552796A JP2009552796A JP5513133B2 JP 5513133 B2 JP5513133 B2 JP 5513133B2 JP 2009552796 A JP2009552796 A JP 2009552796A JP 2009552796 A JP2009552796 A JP 2009552796A JP 5513133 B2 JP5513133 B2 JP 5513133B2
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- 150000001875 compounds Chemical class 0.000 title claims description 93
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 title 1
- 239000000758 substrate Substances 0.000 claims description 62
- 239000000203 mixture Substances 0.000 claims description 57
- -1 Perfluoro Chemical group 0.000 claims description 48
- 238000000576 coating method Methods 0.000 claims description 44
- 125000002947 alkylene group Chemical group 0.000 claims description 39
- 239000011248 coating agent Substances 0.000 claims description 39
- 125000004432 carbon atom Chemical group C* 0.000 claims description 29
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical group [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 28
- 229910000077 silane Inorganic materials 0.000 claims description 28
- 125000006551 perfluoro alkylene group Chemical group 0.000 claims description 11
- 125000005429 oxyalkyl group Chemical group 0.000 claims description 4
- 239000000047 product Substances 0.000 description 27
- 238000000034 method Methods 0.000 description 26
- 230000003667 anti-reflective effect Effects 0.000 description 25
- 125000000217 alkyl group Chemical group 0.000 description 23
- 230000003373 anti-fouling effect Effects 0.000 description 23
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 20
- 230000000269 nucleophilic effect Effects 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical compound [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 description 19
- 238000003756 stirring Methods 0.000 description 19
- 239000008199 coating composition Substances 0.000 description 18
- 229910052799 carbon Inorganic materials 0.000 description 17
- 239000002904 solvent Substances 0.000 description 17
- 229910052731 fluorine Inorganic materials 0.000 description 16
- 239000011737 fluorine Substances 0.000 description 16
- 229910052739 hydrogen Inorganic materials 0.000 description 16
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 15
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- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
- 125000000732 arylene group Chemical group 0.000 description 12
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 12
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- 238000006845 Michael addition reaction Methods 0.000 description 11
- 239000011521 glass Substances 0.000 description 11
- 239000000126 substance Substances 0.000 description 11
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
- 239000008346 aqueous phase Substances 0.000 description 10
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
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- 238000002360 preparation method Methods 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 7
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- SJECZPVISLOESU-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN SJECZPVISLOESU-UHFFFAOYSA-N 0.000 description 6
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- 229910052814 silicon oxide Inorganic materials 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
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- 150000001298 alcohols Chemical class 0.000 description 5
- 150000001412 amines Chemical group 0.000 description 5
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 5
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- PGFXOWRDDHCDTE-UHFFFAOYSA-N hexafluoropropylene oxide Chemical compound FC(F)(F)C1(F)OC1(F)F PGFXOWRDDHCDTE-UHFFFAOYSA-N 0.000 description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 5
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 5
- 235000019341 magnesium sulphate Nutrition 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 239000012299 nitrogen atmosphere Substances 0.000 description 5
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- KAVGMUDTWQVPDF-UHFFFAOYSA-N perflubutane Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)F KAVGMUDTWQVPDF-UHFFFAOYSA-N 0.000 description 5
- 229920000768 polyamine Chemical class 0.000 description 5
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- 238000010992 reflux Methods 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
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- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 description 4
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- 239000012141 concentrate Substances 0.000 description 4
- 230000002596 correlated effect Effects 0.000 description 4
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- 125000005842 heteroatom Chemical group 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
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- 150000004756 silanes Chemical class 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- MRIKSZXJKCQQFT-UHFFFAOYSA-N (3-hydroxy-2,2-dimethylpropyl) prop-2-enoate Chemical compound OCC(C)(C)COC(=O)C=C MRIKSZXJKCQQFT-UHFFFAOYSA-N 0.000 description 3
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 3
- FUVKFLJWBHVMHX-UHFFFAOYSA-N 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonamide Chemical compound NS(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F FUVKFLJWBHVMHX-UHFFFAOYSA-N 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 3
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 3
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 3
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 3
- 239000004925 Acrylic resin Substances 0.000 description 3
- 229920000178 Acrylic resin Polymers 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 238000004566 IR spectroscopy Methods 0.000 description 3
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 3
- 239000005642 Oleic acid Substances 0.000 description 3
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 3
- 239000004642 Polyimide Substances 0.000 description 3
- 239000004793 Polystyrene Substances 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- TUOBEAZXHLTYLF-UHFFFAOYSA-N [2-(hydroxymethyl)-2-(prop-2-enoyloxymethyl)butyl] prop-2-enoate Chemical compound C=CC(=O)OCC(CO)(CC)COC(=O)C=C TUOBEAZXHLTYLF-UHFFFAOYSA-N 0.000 description 3
- 238000005299 abrasion Methods 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 238000004140 cleaning Methods 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 230000002209 hydrophobic effect Effects 0.000 description 3
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- DVYVMJLSUSGYMH-UHFFFAOYSA-N n-methyl-3-trimethoxysilylpropan-1-amine Chemical compound CNCCC[Si](OC)(OC)OC DVYVMJLSUSGYMH-UHFFFAOYSA-N 0.000 description 3
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 125000005702 oxyalkylene group Chemical group 0.000 description 3
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
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- SGUVLZREKBPKCE-UHFFFAOYSA-N 1,5-diazabicyclo[4.3.0]-non-5-ene Chemical compound C1CCN=C2CCCN21 SGUVLZREKBPKCE-UHFFFAOYSA-N 0.000 description 2
- SYNPRNNJJLRHTI-UHFFFAOYSA-N 2-(hydroxymethyl)butane-1,4-diol Chemical class OCCC(CO)CO SYNPRNNJJLRHTI-UHFFFAOYSA-N 0.000 description 2
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- 240000007124 Brassica oleracea Species 0.000 description 2
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- 235000012905 Brassica oleracea var viridis Nutrition 0.000 description 2
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 2
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- 150000001266 acyl halides Chemical class 0.000 description 2
- 238000012644 addition polymerization Methods 0.000 description 2
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- 125000003158 alcohol group Chemical group 0.000 description 2
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- 125000003277 amino group Chemical group 0.000 description 2
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- DCAYPVUWAIABOU-UHFFFAOYSA-N hexadecane Chemical compound CCCCCCCCCCCCCCCC DCAYPVUWAIABOU-UHFFFAOYSA-N 0.000 description 2
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- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 2
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- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
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- WZQYLKIRNOXHAG-UHFFFAOYSA-N 1-tributoxysilylpropan-1-amine Chemical compound CCCCO[Si](OCCCC)(OCCCC)C(N)CC WZQYLKIRNOXHAG-UHFFFAOYSA-N 0.000 description 1
- YHVSHKVTYHHOSC-UHFFFAOYSA-N 1-tributoxysilylpropan-2-amine Chemical compound CCCCO[Si](CC(C)N)(OCCCC)OCCCC YHVSHKVTYHHOSC-UHFFFAOYSA-N 0.000 description 1
- REDHIHUACWEXBN-UHFFFAOYSA-N 1-triethoxysilylethanamine Chemical compound CCO[Si](OCC)(OCC)C(C)N REDHIHUACWEXBN-UHFFFAOYSA-N 0.000 description 1
- JBHRGAHUHVVXQI-UHFFFAOYSA-N 1-triethoxysilylpropan-1-amine Chemical compound CCO[Si](OCC)(OCC)C(N)CC JBHRGAHUHVVXQI-UHFFFAOYSA-N 0.000 description 1
- HXJZEGBVQCRLOD-UHFFFAOYSA-N 1-triethoxysilylpropan-2-amine Chemical compound CCO[Si](CC(C)N)(OCC)OCC HXJZEGBVQCRLOD-UHFFFAOYSA-N 0.000 description 1
- BPBYHTCPEJUYNG-UHFFFAOYSA-N 1-trimethoxysilylethanamine Chemical compound CO[Si](OC)(OC)C(C)N BPBYHTCPEJUYNG-UHFFFAOYSA-N 0.000 description 1
- OPWQHYSPLFFRMU-UHFFFAOYSA-N 1-trimethoxysilylpropan-1-amine Chemical compound CCC(N)[Si](OC)(OC)OC OPWQHYSPLFFRMU-UHFFFAOYSA-N 0.000 description 1
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- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Chemical compound [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229910052715 tantalum Inorganic materials 0.000 description 1
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000012780 transparent material Substances 0.000 description 1
- 229920006352 transparent thermoplastic Polymers 0.000 description 1
- GNQQPTRATSISPA-UHFFFAOYSA-N triethoxy(2-ethylbutyl)silane Chemical compound CCO[Si](OCC)(OCC)CC(CC)CC GNQQPTRATSISPA-UHFFFAOYSA-N 0.000 description 1
- ALVYUZIFSCKIFP-UHFFFAOYSA-N triethoxy(2-methylpropyl)silane Chemical compound CCO[Si](CC(C)C)(OCC)OCC ALVYUZIFSCKIFP-UHFFFAOYSA-N 0.000 description 1
- DENFJSAFJTVPJR-UHFFFAOYSA-N triethoxy(ethyl)silane Chemical compound CCO[Si](CC)(OCC)OCC DENFJSAFJTVPJR-UHFFFAOYSA-N 0.000 description 1
- CPUDPFPXCZDNGI-UHFFFAOYSA-N triethoxy(methyl)silane Chemical compound CCO[Si](C)(OCC)OCC CPUDPFPXCZDNGI-UHFFFAOYSA-N 0.000 description 1
- RFXMNCFJFSYLMT-UHFFFAOYSA-N triethyl 2-ethylbutyl silicate Chemical compound CCO[Si](OCC)(OCC)OCC(CC)CC RFXMNCFJFSYLMT-UHFFFAOYSA-N 0.000 description 1
- XYJRNCYWTVGEEG-UHFFFAOYSA-N trimethoxy(2-methylpropyl)silane Chemical compound CO[Si](OC)(OC)CC(C)C XYJRNCYWTVGEEG-UHFFFAOYSA-N 0.000 description 1
- HQYALQRYBUJWDH-UHFFFAOYSA-N trimethoxy(propyl)silane Chemical compound CCC[Si](OC)(OC)OC HQYALQRYBUJWDH-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
- 239000002023 wood Substances 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31652—Of asbestos
- Y10T428/31663—As siloxane, silicone or silane
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Materials Applied To Surfaces To Minimize Adherence Of Mist Or Water (AREA)
- Paints Or Removers (AREA)
- Silicates, Zeolites, And Molecular Sieves (AREA)
- Surface Treatment Of Glass (AREA)
- Application Of Or Painting With Fluid Materials (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11/683,823 US7745653B2 (en) | 2007-03-08 | 2007-03-08 | Fluorochemical compounds having pendent silyl groups |
| US11/683,823 | 2007-03-08 | ||
| PCT/US2008/054655 WO2008112400A2 (en) | 2007-03-08 | 2008-02-22 | Fluorochemical compounds having pendent silyl groups |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014008417A Division JP2014111617A (ja) | 2007-03-08 | 2014-01-21 | ペンダントシリル基を有するフルオロケミカル化合物 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2010520296A JP2010520296A (ja) | 2010-06-10 |
| JP2010520296A5 JP2010520296A5 (enExample) | 2011-03-17 |
| JP5513133B2 true JP5513133B2 (ja) | 2014-06-04 |
Family
ID=39469454
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009552796A Expired - Fee Related JP5513133B2 (ja) | 2007-03-08 | 2008-02-22 | ペンダントシリル基を有するフルオロケミカル化合物 |
| JP2014008417A Pending JP2014111617A (ja) | 2007-03-08 | 2014-01-21 | ペンダントシリル基を有するフルオロケミカル化合物 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014008417A Pending JP2014111617A (ja) | 2007-03-08 | 2014-01-21 | ペンダントシリル基を有するフルオロケミカル化合物 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US7745653B2 (enExample) |
| EP (1) | EP2134729B1 (enExample) |
| JP (2) | JP5513133B2 (enExample) |
| CN (1) | CN101679461B (enExample) |
| WO (1) | WO2008112400A2 (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2014111617A (ja) * | 2007-03-08 | 2014-06-19 | 3M Innovative Properties Co | ペンダントシリル基を有するフルオロケミカル化合物 |
| CN107504160A (zh) * | 2017-08-11 | 2017-12-22 | 安徽江淮汽车集团股份有限公司 | 一种汽车传动轴结构 |
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| WO2006049020A1 (ja) * | 2004-11-01 | 2006-05-11 | Daikin Industries, Ltd. | ガラス系基材処理用組成物 |
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-
2007
- 2007-03-08 US US11/683,823 patent/US7745653B2/en not_active Expired - Fee Related
-
2008
- 2008-02-22 JP JP2009552796A patent/JP5513133B2/ja not_active Expired - Fee Related
- 2008-02-22 CN CN2008800075617A patent/CN101679461B/zh not_active Expired - Fee Related
- 2008-02-22 WO PCT/US2008/054655 patent/WO2008112400A2/en not_active Ceased
- 2008-02-22 EP EP20080730453 patent/EP2134729B1/en not_active Not-in-force
-
2014
- 2014-01-21 JP JP2014008417A patent/JP2014111617A/ja active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2014111617A (ja) * | 2007-03-08 | 2014-06-19 | 3M Innovative Properties Co | ペンダントシリル基を有するフルオロケミカル化合物 |
| CN107504160A (zh) * | 2017-08-11 | 2017-12-22 | 安徽江淮汽车集团股份有限公司 | 一种汽车传动轴结构 |
Also Published As
| Publication number | Publication date |
|---|---|
| CN101679461B (zh) | 2013-05-29 |
| EP2134729A2 (en) | 2009-12-23 |
| WO2008112400A9 (en) | 2009-04-16 |
| US7745653B2 (en) | 2010-06-29 |
| WO2008112400A3 (en) | 2008-12-04 |
| JP2014111617A (ja) | 2014-06-19 |
| EP2134729B1 (en) | 2013-12-04 |
| US20080220264A1 (en) | 2008-09-11 |
| WO2008112400A2 (en) | 2008-09-18 |
| CN101679461A (zh) | 2010-03-24 |
| JP2010520296A (ja) | 2010-06-10 |
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