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
- Publication number
- 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
- Authority
- JP
- Japan
- Prior art keywords
- group
- formula
- compound
- coating
- och
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 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
- 229920000728 polyester Polymers 0.000 description 15
- 239000000463 material Substances 0.000 description 13
- 229910044991 metal oxide Inorganic materials 0.000 description 13
- 150000004706 metal oxides Chemical class 0.000 description 13
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 13
- 229920005862 polyol Polymers 0.000 description 13
- 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
- 239000010410 layer Substances 0.000 description 12
- 229910052760 oxygen Inorganic materials 0.000 description 12
- 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
- 125000003118 aryl group Chemical group 0.000 description 10
- 239000001301 oxygen Substances 0.000 description 10
- 238000005160 1H NMR spectroscopy Methods 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 239000002253 acid Substances 0.000 description 9
- 125000001153 fluoro group Chemical group F* 0.000 description 9
- 238000011282 treatment Methods 0.000 description 9
- 239000006117 anti-reflective coating Substances 0.000 description 8
- 238000005229 chemical vapour deposition Methods 0.000 description 8
- 238000003618 dip coating Methods 0.000 description 8
- 150000002148 esters Chemical class 0.000 description 8
- 125000000524 functional group Chemical group 0.000 description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 description 8
- 239000003921 oil Substances 0.000 description 8
- 125000004430 oxygen atom Chemical group O* 0.000 description 8
- 150000003077 polyols Chemical class 0.000 description 8
- 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
- 239000000243 solution Substances 0.000 description 8
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 7
- 239000000919 ceramic Substances 0.000 description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- SJECZPVISLOESU-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN SJECZPVISLOESU-UHFFFAOYSA-N 0.000 description 6
- 238000005481 NMR spectroscopy Methods 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 125000005843 halogen group Chemical group 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 230000003287 optical effect Effects 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 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
- 238000006957 Michael reaction Methods 0.000 description 5
- 239000004721 Polyphenylene oxide Substances 0.000 description 5
- 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
- 238000001704 evaporation Methods 0.000 description 5
- 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
- 239000012044 organic layer Substances 0.000 description 5
- 229920000620 organic polymer Polymers 0.000 description 5
- 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
- 229920000515 polycarbonate Polymers 0.000 description 5
- 239000004417 polycarbonate Substances 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 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
- 150000001408 amides Chemical class 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 239000012141 concentrate Substances 0.000 description 4
- 230000002596 correlated effect Effects 0.000 description 4
- 230000000875 corresponding effect Effects 0.000 description 4
- 238000000151 deposition Methods 0.000 description 4
- 238000007688 edging Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 125000005842 heteroatom Chemical group 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 229920000570 polyether Polymers 0.000 description 4
- 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
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 3
- 229920000139 polyethylene terephthalate Polymers 0.000 description 3
- 239000005020 polyethylene terephthalate Substances 0.000 description 3
- 229920001721 polyimide Polymers 0.000 description 3
- 229920000193 polymethacrylate Polymers 0.000 description 3
- 239000004926 polymethyl methacrylate Substances 0.000 description 3
- 229920002223 polystyrene Polymers 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 239000002356 single layer Substances 0.000 description 3
- 230000003068 static effect Effects 0.000 description 3
- 239000004575 stone Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 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
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- BHWUCEATHBXPOV-UHFFFAOYSA-N 2-triethoxysilylethanamine Chemical compound CCO[Si](CCN)(OCC)OCC BHWUCEATHBXPOV-UHFFFAOYSA-N 0.000 description 2
- KQIGMPWTAHJUMN-UHFFFAOYSA-N 3-aminopropane-1,2-diol Chemical compound NCC(O)CO KQIGMPWTAHJUMN-UHFFFAOYSA-N 0.000 description 2
- TZZGHGKTHXIOMN-UHFFFAOYSA-N 3-trimethoxysilyl-n-(3-trimethoxysilylpropyl)propan-1-amine Chemical compound CO[Si](OC)(OC)CCCNCCC[Si](OC)(OC)OC TZZGHGKTHXIOMN-UHFFFAOYSA-N 0.000 description 2
- 240000007124 Brassica oleracea Species 0.000 description 2
- 235000003899 Brassica oleracea var acephala Nutrition 0.000 description 2
- 235000012905 Brassica oleracea var viridis Nutrition 0.000 description 2
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 150000001266 acyl halides Chemical class 0.000 description 2
- 238000012644 addition polymerization Methods 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 125000003158 alcohol group Chemical group 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 229920002301 cellulose acetate Polymers 0.000 description 2
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 238000011109 contamination Methods 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- 230000008034 disappearance Effects 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 239000000428 dust Substances 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 150000002118 epoxides Chemical class 0.000 description 2
- 238000005194 fractionation Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- DCAYPVUWAIABOU-UHFFFAOYSA-N hexadecane Chemical compound CCCCCCCCCCCCCCCC DCAYPVUWAIABOU-UHFFFAOYSA-N 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 229910052738 indium Inorganic materials 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 238000006384 oligomerization reaction Methods 0.000 description 2
- 150000002921 oxetanes Chemical class 0.000 description 2
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 2
- 239000000123 paper Substances 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- RVZRBWKZFJCCIB-UHFFFAOYSA-N perfluorotributylamine Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)N(C(F)(F)C(F)(F)C(F)(F)C(F)(F)F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F RVZRBWKZFJCCIB-UHFFFAOYSA-N 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920000058 polyacrylate Polymers 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 229920000098 polyolefin Polymers 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- 229920002578 polythiourethane polymer Polymers 0.000 description 2
- 239000004800 polyvinyl chloride Substances 0.000 description 2
- 229920000915 polyvinyl chloride Polymers 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 2
- 239000011253 protective coating Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 2
- 238000007142 ring opening reaction Methods 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 238000004528 spin coating Methods 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 239000012815 thermoplastic material Substances 0.000 description 2
- 238000007740 vapor deposition Methods 0.000 description 2
- 229910052727 yttrium Inorganic materials 0.000 description 2
- 229910001928 zirconium oxide Inorganic materials 0.000 description 2
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 1
- LGPAKRMZNPYPMG-UHFFFAOYSA-N (3-hydroxy-2-prop-2-enoyloxypropyl) prop-2-enoate Chemical compound C=CC(=O)OC(CO)COC(=O)C=C LGPAKRMZNPYPMG-UHFFFAOYSA-N 0.000 description 1
- PLFFHJWXOGYWPR-HEDMGYOXSA-N (4r)-4-[(3r,3as,5ar,5br,7as,11as,11br,13ar,13bs)-5a,5b,8,8,11a,13b-hexamethyl-1,2,3,3a,4,5,6,7,7a,9,10,11,11b,12,13,13a-hexadecahydrocyclopenta[a]chrysen-3-yl]pentan-1-ol Chemical class C([C@]1(C)[C@H]2CC[C@H]34)CCC(C)(C)[C@@H]1CC[C@@]2(C)[C@]4(C)CC[C@@H]1[C@]3(C)CC[C@@H]1[C@@H](CCCO)C PLFFHJWXOGYWPR-HEDMGYOXSA-N 0.000 description 1
- KYVBNYUBXIEUFW-UHFFFAOYSA-N 1,1,3,3-tetramethylguanidine Chemical compound CN(C)C(=N)N(C)C KYVBNYUBXIEUFW-UHFFFAOYSA-N 0.000 description 1
- YNGDWRXWKFWCJY-UHFFFAOYSA-N 1,4-Dihydropyridine Chemical compound C1C=CNC=C1 YNGDWRXWKFWCJY-UHFFFAOYSA-N 0.000 description 1
- BOBMDNIYRSTZLQ-UHFFFAOYSA-N 1-[diethoxy(methyl)silyl]propan-2-amine Chemical compound CCO[Si](C)(CC(C)N)OCC BOBMDNIYRSTZLQ-UHFFFAOYSA-N 0.000 description 1
- UTHDGOQKIWLLCO-UHFFFAOYSA-N 1-hydroxyhexyl prop-2-enoate Chemical compound CCCCCC(O)OC(=O)C=C UTHDGOQKIWLLCO-UHFFFAOYSA-N 0.000 description 1
- 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
- KBRVQAUYZUFKAJ-UHFFFAOYSA-N 1-trimethoxysilylpropan-2-amine Chemical compound CO[Si](OC)(OC)CC(C)N KBRVQAUYZUFKAJ-UHFFFAOYSA-N 0.000 description 1
- NFLIXQOYHPEPPY-UHFFFAOYSA-N 1-tripropoxysilylpropan-1-amine Chemical compound CCCO[Si](OCCC)(OCCC)C(N)CC NFLIXQOYHPEPPY-UHFFFAOYSA-N 0.000 description 1
- OFZOOXNQZZDXRT-UHFFFAOYSA-N 1-tripropoxysilylpropan-2-amine Chemical compound CCCO[Si](CC(C)N)(OCCC)OCCC OFZOOXNQZZDXRT-UHFFFAOYSA-N 0.000 description 1
- RWXMAAYKJDQVTF-UHFFFAOYSA-N 2-(2-hydroxyethoxy)ethyl prop-2-enoate Chemical compound OCCOCCOC(=O)C=C RWXMAAYKJDQVTF-UHFFFAOYSA-N 0.000 description 1
- YATYDCQGPUOZGZ-UHFFFAOYSA-N 2-(2-hydroxypropoxy)propan-1-ol;prop-2-enoic acid Chemical compound OC(=O)C=C.CC(O)COC(C)CO YATYDCQGPUOZGZ-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- NQOGBCBPDVTBFM-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol;prop-2-enoic acid Chemical compound OC(=O)C=C.CC(O)COC(C)COC(C)CO NQOGBCBPDVTBFM-UHFFFAOYSA-N 0.000 description 1
- QUASZQPLPKGIJY-UHFFFAOYSA-N 2-[2-[2-(2-hydroxyethoxy)ethoxy]ethoxy]ethyl prop-2-enoate Chemical compound OCCOCCOCCOCCOC(=O)C=C QUASZQPLPKGIJY-UHFFFAOYSA-N 0.000 description 1
- FDSUVTROAWLVJA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol;prop-2-enoic acid Chemical compound OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OCC(CO)(CO)COCC(CO)(CO)CO FDSUVTROAWLVJA-UHFFFAOYSA-N 0.000 description 1
- UKQBWWAPJNHIQR-UHFFFAOYSA-N 2-ethyl-2-(hydroxymethyl)propane-1,3-diol;prop-2-enoic acid Chemical class OC(=O)C=C.CCC(CO)(CO)CO UKQBWWAPJNHIQR-UHFFFAOYSA-N 0.000 description 1
- XNFIEYMGNIUQIF-UHFFFAOYSA-N 2-ethyl-2-(hydroxymethyl)propane-1,3-diol;prop-2-enoic acid Chemical class OC(=O)C=C.OC(=O)C=C.CCC(CO)(CO)CO XNFIEYMGNIUQIF-UHFFFAOYSA-N 0.000 description 1
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 1
- TXZZSVASDZFPQY-UHFFFAOYSA-N 2-tributoxysilylethanamine Chemical compound CCCCO[Si](CCN)(OCCCC)OCCCC TXZZSVASDZFPQY-UHFFFAOYSA-N 0.000 description 1
- QHQNYHZHLAAHRW-UHFFFAOYSA-N 2-trimethoxysilylethanamine Chemical compound CO[Si](OC)(OC)CCN QHQNYHZHLAAHRW-UHFFFAOYSA-N 0.000 description 1
- UNKZGKRGTGCFKH-UHFFFAOYSA-N 2-tripropoxysilylethanamine Chemical compound CCCO[Si](CCN)(OCCC)OCCC UNKZGKRGTGCFKH-UHFFFAOYSA-N 0.000 description 1
- UAHAMNBFDHWCPU-UHFFFAOYSA-N 3-tributoxysilylpropan-1-amine Chemical compound CCCCO[Si](CCCN)(OCCCC)OCCCC UAHAMNBFDHWCPU-UHFFFAOYSA-N 0.000 description 1
- KBQVDAIIQCXKPI-UHFFFAOYSA-N 3-trimethoxysilylpropyl prop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C=C KBQVDAIIQCXKPI-UHFFFAOYSA-N 0.000 description 1
- XUZVALKTSQQLCH-UHFFFAOYSA-N 3-tripropoxysilylpropan-1-amine Chemical compound CCCO[Si](CCCN)(OCCC)OCCC XUZVALKTSQQLCH-UHFFFAOYSA-N 0.000 description 1
- NDWUBGAGUCISDV-UHFFFAOYSA-N 4-hydroxybutyl prop-2-enoate Chemical compound OCCCCOC(=O)C=C NDWUBGAGUCISDV-UHFFFAOYSA-N 0.000 description 1
- QAPHWZATUFXMGN-UHFFFAOYSA-N 4-trimethoxysilylbutan-2-amine Chemical compound CO[Si](OC)(OC)CCC(C)N QAPHWZATUFXMGN-UHFFFAOYSA-N 0.000 description 1
- CEKGELWTDRCMNF-UHFFFAOYSA-N 5,5-dihydroxyimidazolidine-2,4-dione Chemical group OC1(O)NC(=O)NC1=O CEKGELWTDRCMNF-UHFFFAOYSA-N 0.000 description 1
- FIHBHSQYSYVZQE-UHFFFAOYSA-N 6-prop-2-enoyloxyhexyl prop-2-enoate Chemical compound C=CC(=O)OCCCCCCOC(=O)C=C FIHBHSQYSYVZQE-UHFFFAOYSA-N 0.000 description 1
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 1
- IFRWXUXQRPUMST-UHFFFAOYSA-N C(C=C)(=O)O.C(CC(C)O)O.C(C=C)(=O)OCC(O)CO Chemical compound C(C=C)(=O)O.C(CC(C)O)O.C(C=C)(=O)OCC(O)CO IFRWXUXQRPUMST-UHFFFAOYSA-N 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 229920001747 Cellulose diacetate Polymers 0.000 description 1
- 229920002284 Cellulose triacetate Polymers 0.000 description 1
- 229910052684 Cerium Inorganic materials 0.000 description 1
- 101000856234 Clostridium acetobutylicum (strain ATCC 824 / DSM 792 / JCM 1419 / LMG 5710 / VKM B-1787) Butyrate-acetoacetate CoA-transferase subunit A Proteins 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical class ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- 229920001410 Microfiber Polymers 0.000 description 1
- AGYXRRXOPFACFH-UHFFFAOYSA-N NCCNC(C)[Si](OC)(OC)OC.NCCNCC[Si](OCCC)(OCCC)OCCC Chemical compound NCCNC(C)[Si](OC)(OC)OC.NCCNCC[Si](OCCC)(OCCC)OCCC AGYXRRXOPFACFH-UHFFFAOYSA-N 0.000 description 1
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
- 229920001774 Perfluoroether Polymers 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 229910008051 Si-OH Inorganic materials 0.000 description 1
- 229910008326 Si-Y Inorganic materials 0.000 description 1
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- 229910002808 Si–O–Si Inorganic materials 0.000 description 1
- 229910006358 Si—OH Inorganic materials 0.000 description 1
- 229910006773 Si—Y Inorganic materials 0.000 description 1
- 108091092920 SmY RNA Proteins 0.000 description 1
- 241001237710 Smyrna Species 0.000 description 1
- 229910006404 SnO 2 Inorganic materials 0.000 description 1
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 1
- 229910010413 TiO 2 Inorganic materials 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
- NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 description 1
- KKVKUNIBLLLFHA-UHFFFAOYSA-N [1-(hydroxymethyl)cyclohexyl]methyl prop-2-enoate Chemical compound C=CC(=O)OCC1(CO)CCCCC1 KKVKUNIBLLLFHA-UHFFFAOYSA-N 0.000 description 1
- HVVWZTWDBSEWIH-UHFFFAOYSA-N [2-(hydroxymethyl)-3-prop-2-enoyloxy-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(CO)(COC(=O)C=C)COC(=O)C=C HVVWZTWDBSEWIH-UHFFFAOYSA-N 0.000 description 1
- XRMBQHTWUBGQDN-UHFFFAOYSA-N [2-[2,2-bis(prop-2-enoyloxymethyl)butoxymethyl]-2-(prop-2-enoyloxymethyl)butyl] prop-2-enoate Chemical compound C=CC(=O)OCC(COC(=O)C=C)(CC)COCC(CC)(COC(=O)C=C)COC(=O)C=C XRMBQHTWUBGQDN-UHFFFAOYSA-N 0.000 description 1
- IUHFWCGCSVTMPG-UHFFFAOYSA-N [C].[C] Chemical group [C].[C] IUHFWCGCSVTMPG-UHFFFAOYSA-N 0.000 description 1
- LTIPUQSMGRSZOQ-UHFFFAOYSA-N [C].[C].[O] Chemical group [C].[C].[O] LTIPUQSMGRSZOQ-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000003926 acrylamides Chemical class 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- XECAHXYUAAWDEL-UHFFFAOYSA-N acrylonitrile butadiene styrene Chemical compound C=CC=C.C=CC#N.C=CC1=CC=CC=C1 XECAHXYUAAWDEL-UHFFFAOYSA-N 0.000 description 1
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 1
- 239000004676 acrylonitrile butadiene styrene Substances 0.000 description 1
- 229920001893 acrylonitrile styrene Polymers 0.000 description 1
- 125000002015 acyclic group Chemical group 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 150000007824 aliphatic compounds Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 238000004630 atomic force microscopy Methods 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 229910052797 bismuth Inorganic materials 0.000 description 1
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 1
- 229940106691 bisphenol a Drugs 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- IYRWEQXVUNLMAY-UHFFFAOYSA-N carbonyl fluoride Chemical group FC(F)=O IYRWEQXVUNLMAY-UHFFFAOYSA-N 0.000 description 1
- 150000003857 carboxamides Chemical class 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000004568 cement Substances 0.000 description 1
- ZMIGMASIKSOYAM-UHFFFAOYSA-N cerium Chemical compound [Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce] ZMIGMASIKSOYAM-UHFFFAOYSA-N 0.000 description 1
- 238000003486 chemical etching Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000004567 concrete Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000003851 corona treatment Methods 0.000 description 1
- 238000007766 curtain coating Methods 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 125000004386 diacrylate group Chemical group 0.000 description 1
- 239000003989 dielectric material Substances 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000010894 electron beam technology Methods 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- CWAFVXWRGIEBPL-UHFFFAOYSA-N ethoxysilane Chemical compound CCO[SiH3] CWAFVXWRGIEBPL-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- SBRXLTRZCJVAPH-UHFFFAOYSA-N ethyl(trimethoxy)silane Chemical compound CC[Si](OC)(OC)OC SBRXLTRZCJVAPH-UHFFFAOYSA-N 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 150000002222 fluorine compounds Chemical class 0.000 description 1
- 238000000806 fluorine-19 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000007756 gravure coating Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000004816 latex Substances 0.000 description 1
- 229920000126 latex Polymers 0.000 description 1
- 125000005647 linker group Chemical group 0.000 description 1
- 238000003754 machining Methods 0.000 description 1
- 229910001512 metal fluoride Inorganic materials 0.000 description 1
- 229910001092 metal group alloy Inorganic materials 0.000 description 1
- 229910052976 metal sulfide Inorganic materials 0.000 description 1
- 229910052752 metalloid Inorganic materials 0.000 description 1
- 150000002738 metalloids Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- VHRYZQNGTZXDNX-UHFFFAOYSA-N methacryloyl chloride Chemical compound CC(=C)C(Cl)=O VHRYZQNGTZXDNX-UHFFFAOYSA-N 0.000 description 1
- 238000006140 methanolysis reaction Methods 0.000 description 1
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- UJNZOIKQAUQOCN-UHFFFAOYSA-N methyl(diphenyl)phosphane Chemical compound C=1C=CC=CC=1P(C)C1=CC=CC=C1 UJNZOIKQAUQOCN-UHFFFAOYSA-N 0.000 description 1
- XWZZZMXGYMXMQX-UHFFFAOYSA-N methyl-bis(4-methylphenyl)phosphane Chemical compound C=1C=C(C)C=CC=1P(C)C1=CC=C(C)C=C1 XWZZZMXGYMXMQX-UHFFFAOYSA-N 0.000 description 1
- JAHMEIUBFPYPIM-UHFFFAOYSA-N methyl-tris(propan-2-ylperoxy)silane Chemical compound CC(C)OO[Si](C)(OOC(C)C)OOC(C)C JAHMEIUBFPYPIM-UHFFFAOYSA-N 0.000 description 1
- BFXIKLCIZHOAAZ-UHFFFAOYSA-N methyltrimethoxysilane Chemical compound CO[Si](C)(OC)OC BFXIKLCIZHOAAZ-UHFFFAOYSA-N 0.000 description 1
- 239000003658 microfiber Substances 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 229910000096 monohydride Inorganic materials 0.000 description 1
- MEACNHPYSUFTMA-UHFFFAOYSA-N n'-(1-triethoxysilylethyl)ethane-1,2-diamine Chemical compound CCO[Si](OCC)(OCC)C(C)NCCN MEACNHPYSUFTMA-UHFFFAOYSA-N 0.000 description 1
- XRAYTRHUIGYKJR-UHFFFAOYSA-N n'-(1-trimethoxysilylpropan-2-yl)ethane-1,2-diamine Chemical compound CO[Si](OC)(OC)CC(C)NCCN XRAYTRHUIGYKJR-UHFFFAOYSA-N 0.000 description 1
- RVTQZLMIVBKMFP-UHFFFAOYSA-N n'-(1-tripropoxysilylethyl)ethane-1,2-diamine Chemical compound CCCO[Si](OCCC)(OCCC)C(C)NCCN RVTQZLMIVBKMFP-UHFFFAOYSA-N 0.000 description 1
- UZGUKNWYSKQNHJ-UHFFFAOYSA-N n'-(1-tripropoxysilylpropan-2-yl)ethane-1,2-diamine Chemical compound CCCO[Si](OCCC)(OCCC)CC(C)NCCN UZGUKNWYSKQNHJ-UHFFFAOYSA-N 0.000 description 1
- HNHARWVJLKJURT-UHFFFAOYSA-N n'-(2-triethoxysilylethyl)ethane-1,2-diamine Chemical compound CCO[Si](OCC)(OCC)CCNCCN HNHARWVJLKJURT-UHFFFAOYSA-N 0.000 description 1
- ITBJJJXGNILUKA-UHFFFAOYSA-N n'-(2-triethoxysilylethyl)propane-1,3-diamine Chemical compound CCO[Si](OCC)(OCC)CCNCCCN ITBJJJXGNILUKA-UHFFFAOYSA-N 0.000 description 1
- FPFKERZHIGFTEI-UHFFFAOYSA-N n'-(2-trimethoxysilylethyl)ethane-1,2-diamine Chemical compound CO[Si](OC)(OC)CCNCCN FPFKERZHIGFTEI-UHFFFAOYSA-N 0.000 description 1
- MPVWTKVPRCGUAA-UHFFFAOYSA-N n'-(2-trimethoxysilylethyl)propane-1,3-diamine Chemical compound CO[Si](OC)(OC)CCNCCCN MPVWTKVPRCGUAA-UHFFFAOYSA-N 0.000 description 1
- LCWRALGVVHJJLK-UHFFFAOYSA-N n'-(2-tripropoxysilylethyl)propane-1,3-diamine Chemical compound CCCO[Si](OCCC)(OCCC)CCNCCCN LCWRALGVVHJJLK-UHFFFAOYSA-N 0.000 description 1
- INJVFBCDVXYHGQ-UHFFFAOYSA-N n'-(3-triethoxysilylpropyl)ethane-1,2-diamine Chemical compound CCO[Si](OCC)(OCC)CCCNCCN INJVFBCDVXYHGQ-UHFFFAOYSA-N 0.000 description 1
- PHQOGHDTIVQXHL-UHFFFAOYSA-N n'-(3-trimethoxysilylpropyl)ethane-1,2-diamine Chemical compound CO[Si](OC)(OC)CCCNCCN PHQOGHDTIVQXHL-UHFFFAOYSA-N 0.000 description 1
- PXEPBRRYHKUTDN-UHFFFAOYSA-N n'-(3-tripropoxysilylpropyl)ethane-1,2-diamine Chemical compound CCCO[Si](OCCC)(OCCC)CCCNCCN PXEPBRRYHKUTDN-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052758 niobium Inorganic materials 0.000 description 1
- 239000010955 niobium Substances 0.000 description 1
- GUCVJGMIXFAOAE-UHFFFAOYSA-N niobium atom Chemical compound [Nb] GUCVJGMIXFAOAE-UHFFFAOYSA-N 0.000 description 1
- 150000004767 nitrides Chemical class 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000012038 nucleophile Substances 0.000 description 1
- OTLDLKLSNZMTTA-UHFFFAOYSA-N octahydro-1h-4,7-methanoindene-1,5-diyldimethanol Chemical compound C1C2C3C(CO)CCC3C1C(CO)C2 OTLDLKLSNZMTTA-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 150000001282 organosilanes Chemical class 0.000 description 1
- 125000005824 oxyalkoxy group Chemical group 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000005003 perfluorobutyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)C(F)(F)* 0.000 description 1
- 125000005007 perfluorooctyl group Chemical group FC(C(C(C(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)* 0.000 description 1
- 239000010702 perfluoropolyether Substances 0.000 description 1
- 125000005009 perfluoropropyl group Chemical group FC(C(C(F)(F)F)(F)F)(F)* 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 238000001020 plasma etching Methods 0.000 description 1
- 238000005498 polishing Methods 0.000 description 1
- 229920002285 poly(styrene-co-acrylonitrile) Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920006380 polyphenylene oxide Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- SCUZVMOVTVSBLE-UHFFFAOYSA-N prop-2-enenitrile;styrene Chemical compound C=CC#N.C=CC1=CC=CC=C1 SCUZVMOVTVSBLE-UHFFFAOYSA-N 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 238000002310 reflectometry Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000007763 reverse roll coating Methods 0.000 description 1
- 230000003678 scratch resistant effect Effects 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 239000011265 semifinished product Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 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)
- Paints Or Removers (AREA)
- Materials Applied To Surfaces To Minimize Adherence Of Mist Or Water (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 | 2007-03-08 | ||
| US11/683,823 US7745653B2 (en) | 2007-03-08 | 2007-03-08 | Fluorochemical compounds having pendent silyl groups |
| 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 |
Families Citing this family (51)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4884180B2 (ja) * | 2006-11-21 | 2012-02-29 | 東京エレクトロン株式会社 | 基板処理装置および基板処理方法 |
| JP5415960B2 (ja) * | 2006-12-20 | 2014-02-12 | スリーエム イノベイティブ プロパティズ カンパニー | ペンダントシリル基を有するフルオロケミカルウレタン化合物 |
| CN101679790B (zh) * | 2007-05-23 | 2012-09-19 | 3M创新有限公司 | 氟化表面活性剂的水性组合物及其使用方法 |
| 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 |
| US7891636B2 (en) | 2007-08-27 | 2011-02-22 | 3M Innovative Properties Company | Silicone mold and use thereof |
| US8058463B2 (en) * | 2007-12-04 | 2011-11-15 | E. I. Du Pont De Nemours And Compnay | Fluorosilanes |
| US20110020657A1 (en) * | 2007-12-27 | 2011-01-27 | Cheng-Chung Chang | Protective coating compositions |
| TWI450043B (zh) * | 2008-03-11 | 2014-08-21 | 3M Innovative Properties Co | 具備保護層之光工具 |
| BRPI0915955A2 (pt) * | 2008-07-18 | 2019-02-26 | 3M Innovative Proferties Company | compostos fluorados de éter e métodos para uso dos mesmos |
| CN102209735B (zh) * | 2008-11-11 | 2015-03-18 | 大金工业株式会社 | 制备拒水拒油防污组合物的方法 |
| WO2010062843A1 (en) * | 2008-11-25 | 2010-06-03 | 3M Innovative Properties Company | Fluorinated ether urethanes and methods of using the same |
| CN102307851B (zh) * | 2008-12-11 | 2015-05-06 | 3M创新有限公司 | 酰胺连接的全氟聚醚硫醇化合物及其制备方法和用途 |
| WO2010080473A1 (en) | 2008-12-18 | 2010-07-15 | 3M Innovative Properties Company | Method of contacting hydrocarbon-bearing formations with fluorinated ether compositions |
| JP5343570B2 (ja) * | 2009-01-13 | 2013-11-13 | 信越化学工業株式会社 | 金属表面処理剤、表面処理鋼材及びその表面処理方法、並びに塗装鋼材及びその製造方法 |
| US8324324B2 (en) * | 2009-06-30 | 2012-12-04 | 3M Innovative Properties Company | Composition and process for preparing curable organofluorine-modified polysilazanes, and polysilazanes prepared thereby |
| US9096712B2 (en) | 2009-07-21 | 2015-08-04 | 3M Innovative Properties Company | Curable compositions, method of coating a phototool, and coated phototool |
| KR101781659B1 (ko) | 2009-09-16 | 2017-09-25 | 쓰리엠 이노베이티브 프로퍼티즈 컴파니 | 플루오르화된 코팅 및 그로 제조된 포토툴 |
| US8420281B2 (en) | 2009-09-16 | 2013-04-16 | 3M Innovative Properties Company | Epoxy-functionalized perfluoropolyether polyurethanes |
| WO2011034845A1 (en) | 2009-09-16 | 2011-03-24 | 3M Innovative Properties Company | Fluorinated coating and phototools made therewith |
| US8268067B2 (en) * | 2009-10-06 | 2012-09-18 | 3M Innovative Properties Company | Perfluoropolyether coating composition for hard surfaces |
| EP2516512B1 (en) | 2009-12-22 | 2015-09-23 | 3M Innovative Properties Company | Process for preparing shelf-stable curable polysilazanes, and polysilazanes prepared thereby |
| CN102712750B (zh) | 2009-12-30 | 2014-06-25 | 3M创新有限公司 | 具有乙二酰胺基团的含全氟聚醚化合物 |
| WO2011082046A1 (en) | 2009-12-30 | 2011-07-07 | 3M Innovative Properties Company | Copolymers with perfluorpolyether segment and multiple aminooxalylamino groups |
| WO2011082063A1 (en) | 2009-12-30 | 2011-07-07 | 3M Innovative Properties Company | Copolymers with perfluorpolyether segment and polydiorganosiloxane segment |
| WO2011082069A1 (en) | 2009-12-30 | 2011-07-07 | 3M Innovative Properties Company | Methods of making polydiorganosiloxane polyoxamide copolymers |
| US10550474B1 (en) | 2010-02-26 | 2020-02-04 | Quantum Innovations, Inc. | Vapor deposition system |
| US10808319B1 (en) | 2010-02-26 | 2020-10-20 | Quantum Innovations, Inc. | System and method for vapor deposition of substrates with circular substrate frame that rotates in a planetary motion and curved lens support arms |
| US20120107558A1 (en) * | 2010-11-01 | 2012-05-03 | Shari Elizabeth Koval | Transparent substrate having durable hydrophobic/oleophobic surface |
| US20130216820A1 (en) | 2010-11-10 | 2013-08-22 | 3M Innovative Properties Company | Hydrophobic fluorinated coatings |
| US20130323519A1 (en) * | 2011-01-31 | 2013-12-05 | 3M Innovative Properties Company | Coatings for barrier films and methods of making and using the same |
| WO2012106184A2 (en) * | 2011-01-31 | 2012-08-09 | 3M Innovative Properties Company | Vapor-deposited coating for barrier films and methods of making and using the same |
| EP2500009A1 (en) | 2011-03-17 | 2012-09-19 | 3M Innovative Properties Company | Dental ceramic article, process of production and use thereof |
| WO2012173803A1 (en) | 2011-06-15 | 2012-12-20 | 3M Innovative Properties Company | Hydrophobic hydrocarbon coatings |
| US9035082B2 (en) | 2011-10-10 | 2015-05-19 | Cytonix, Llc | Low surface energy touch screens, coatings, and methods |
| WO2013126208A1 (en) * | 2012-02-20 | 2013-08-29 | 3M Innovative Properties Company | Oleophobic coatings |
| ES2560839T3 (es) * | 2012-03-22 | 2016-02-23 | Nihon Tokushu Toryo Co., Ltd. | Composición de recubrimiento que previene la escarcha |
| US10784455B2 (en) | 2012-08-08 | 2020-09-22 | 3M Innovative Properties Company | Coatings for barrier films and methods of making and using the same |
| CN104540676B (zh) * | 2012-08-08 | 2017-03-01 | 3M创新有限公司 | 用于阻挡膜的涂层及制备和使用其的方法 |
| KR20160135254A (ko) | 2014-03-18 | 2016-11-25 | 쓰리엠 이노베이티브 프로퍼티즈 컴파니 | 처리된 물품 및 그의 제조 방법 |
| US10233285B2 (en) | 2014-12-08 | 2019-03-19 | 3M Innovative Properties Company | Fluorinated silane compounds, compositions, and articles |
| US10487180B2 (en) | 2014-12-08 | 2019-11-26 | 3M Innovative Properties Company | Compounds comprising modified diorganosiloxane polymers |
| US10689522B2 (en) | 2014-12-19 | 2020-06-23 | Merck Patent Gmbh | Fluorine compounds |
| KR101956830B1 (ko) * | 2015-08-18 | 2019-03-12 | 주식회사 엘지화학 | 저굴절층 및 이를 포함하는 반사 방지 필름 |
| US10858540B2 (en) | 2015-09-23 | 2020-12-08 | 3M Innovative Properties Company | Composition including silanes and methods of making a treated article |
| US10544260B2 (en) * | 2017-08-30 | 2020-01-28 | Ppg Industries Ohio, Inc. | Fluoropolymers, methods of preparing fluoropolymers, and coating compositions containing fluoropolymers |
| JP6939717B2 (ja) * | 2018-06-20 | 2021-09-22 | 信越化学工業株式会社 | 環状アミノオルガノキシシラン化合物およびその製造方法 |
| KR102741016B1 (ko) * | 2018-08-20 | 2024-12-09 | 삼성전자주식회사 | 표면 코팅재, 필름, 적층체 및 표시 장치 |
| WO2021229338A1 (en) | 2020-05-14 | 2021-11-18 | 3M Innovative Properties Company | Fluorinated coupling agents and fluorinated (co)polymer layers made using the same |
| CN115485620A (zh) | 2020-05-14 | 2022-12-16 | 3M创新有限公司 | 氟化光引发剂和使用其制备的氟化(共)聚合物层 |
| WO2021231068A1 (en) * | 2020-05-14 | 2021-11-18 | 3M Innovative Properties Company | Polymerizable compositions and compounds comprising perfluorinated group, hydrolysable silane group, and (meth)acryl group |
| JP7679019B1 (ja) * | 2024-10-11 | 2025-05-19 | 信越化学工業株式会社 | フルオロオキシアルキレン基を繰り返し単位として備えた化合物の分解方法 |
Family Cites Families (45)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3250807A (en) | 1963-08-23 | 1966-05-10 | Du Pont | Dicarboxylic acids of fluorocarbon ethers and fluorides, esters, amides and salts thereof |
| US3250808A (en) | 1963-10-31 | 1966-05-10 | Du Pont | Fluorocarbon ethers derived from hexafluoropropylene epoxide |
| NL133796C (enExample) | 1965-01-21 | 1900-01-01 | ||
| US3719698A (en) | 1967-11-27 | 1973-03-06 | Stevens & Co Inc J P | Polyfluorinated esters of acids containing silicon and amino groups |
| US3810874A (en) | 1969-03-10 | 1974-05-14 | Minnesota Mining & Mfg | Polymers prepared from poly(perfluoro-alkylene oxide) compounds |
| US3646085A (en) * | 1970-09-24 | 1972-02-29 | Du Pont | Perfluoroalkyletheramidoalkyltrialkoxysilanes |
| US4508916A (en) | 1979-04-11 | 1985-04-02 | Minnesota Mining And Manufacturing Company | Curable substituted urethane acrylates |
| US4262072A (en) | 1979-06-25 | 1981-04-14 | Minnesota Mining And Manufacturing Company | Poly(ethylenically unsaturated alkoxy) heterocyclic protective coatings |
| DE3004824A1 (de) | 1980-02-09 | 1981-08-20 | Bayer Ag, 5090 Leverkusen | Polstabilisierendes textilimpraegniermittel |
| US4321404A (en) | 1980-05-20 | 1982-03-23 | Minnesota Mining And Manufacturing Company | Compositions for providing abherent coatings |
| US4348462A (en) | 1980-07-11 | 1982-09-07 | General Electric Company | Abrasion resistant ultraviolet light curable hard coating compositions |
| US4378250A (en) | 1981-07-31 | 1983-03-29 | Treadway Gerald D | Organosilicone coating compositions |
| JPS58167597A (ja) * | 1982-03-29 | 1983-10-03 | Chisso Corp | フルオロアミノシラン化合物 |
| DE3307420A1 (de) | 1983-03-03 | 1984-09-13 | Bayer Ag, 5090 Leverkusen | Textilausruestungsmittel |
| US4617057A (en) * | 1985-06-04 | 1986-10-14 | Dow Corning Corporation | Oil and water repellent coating compositions |
| US4657959A (en) * | 1985-11-15 | 1987-04-14 | Minnesota Mining And Manufacturing Company | Hydrophilic silicones |
| US4866192A (en) * | 1988-04-18 | 1989-09-12 | Dow Corning Corporation | Organosilicon quaternary ammonium antimicrobial compounds |
| US4873140A (en) | 1988-04-27 | 1989-10-10 | Minnesota Mining And Manufacturing Company | Articles having low adhesion articles having coatings thereon |
| JP2665961B2 (ja) * | 1988-12-20 | 1997-10-22 | ナトコペイント株式会社 | 被膜形成方法 |
| CA1327856C (en) | 1989-09-05 | 1994-03-15 | Barry R. Knowlton | Method of enhancing the soil- and stain-resistance characteristics of polyamide and wool fabrics, the fabrics so treated, and treating composition |
| DE4011044A1 (de) * | 1990-04-05 | 1991-10-10 | Fraunhofer Ges Forschung | Silane, verfahren zu ihrer herstellung und ihre verwendung zur herstellung von polymerisaten und polykondensaten |
| JPH0940680A (ja) * | 1995-07-26 | 1997-02-10 | Pola Chem Ind Inc | 脱離基を有する新規なシリコーン |
| DE69624923T2 (de) | 1995-08-11 | 2003-08-21 | Daikin Industries, Ltd. | Silizium enthaltende organische fluorpolymere und ihre verwendung |
| JPH09176323A (ja) * | 1995-12-22 | 1997-07-08 | Pola Chem Ind Inc | フッ素化シリコーン樹脂及びその製造方法 |
| US5866651A (en) * | 1996-10-31 | 1999-02-02 | Minnesota Mining And Manufacturing Company | Hydroxycarbamoylalkoxysilane-based poly(ether-urethane) sealants having improved paint adhesion and laminates prepared therefrom |
| US6277485B1 (en) * | 1998-01-27 | 2001-08-21 | 3M Innovative Properties Company | Antisoiling coatings for antireflective surfaces and methods of preparation |
| US6281468B1 (en) | 2000-03-13 | 2001-08-28 | Essilor International, Compagnie Generale D'optique | Method and apparatus for producing a marking on an ophthalmic lens having a low surface energy |
| US6632508B1 (en) * | 2000-10-27 | 2003-10-14 | 3M Innovative Properties Company | Optical elements comprising a polyfluoropolyether surface treatment |
| WO2003014131A1 (de) * | 2001-08-02 | 2003-02-20 | Clariant Gmbh | Fluoralkylmodifizierte organosilane, verwendung in beschichtungszusammensetzungen |
| US6649272B2 (en) * | 2001-11-08 | 2003-11-18 | 3M Innovative Properties Company | Coating composition comprising fluorochemical polyether silane polycondensate and use thereof |
| US6716534B2 (en) * | 2001-11-08 | 2004-04-06 | 3M Innovative Properties Company | Coating composition comprising a fluorochemical polyether silane partial condensate and use thereof |
| US7425279B2 (en) * | 2002-05-24 | 2008-09-16 | 3M Innovative Properties Company | Fluorochemical composition for treatment of a fibrous substrate |
| DE60317663T2 (de) | 2002-05-24 | 2008-10-30 | 3M Innovative Properties Co., St. Paul | Fluorchemische zusammensetzung enthaltend einen fluorierten polyether und dessen verwendung zur behandlung von fasermaterialien |
| US6923921B2 (en) | 2002-12-30 | 2005-08-02 | 3M Innovative Properties Company | Fluorinated polyether compositions |
| US7217440B2 (en) | 2003-06-13 | 2007-05-15 | Essilor International Compagnie Generale D'optique | Process for replacing an initial outermost coating layer of a coated optical lens with a different coating layer or by depositing thereon a different coating layer |
| US7652115B2 (en) | 2003-09-08 | 2010-01-26 | 3M Innovative Properties Company | Fluorinated polyether isocyanate derived silane compositions |
| US7247386B2 (en) * | 2003-12-23 | 2007-07-24 | 3M Innovative Properties Company | Composition of an oligomeric fluorosilane and surface treatment of retroreflective sheet |
| US6991826B2 (en) * | 2004-04-20 | 2006-01-31 | 3M Innovative Properties Company | Antisoiling coatings for antireflective substrates |
| WO2005116304A2 (en) | 2004-04-23 | 2005-12-08 | Asm America, Inc. | In situ doped epitaxial films |
| US7101618B2 (en) | 2004-05-07 | 2006-09-05 | 3M Innovative Properties Company | Article comprising fluorochemical surface layer |
| US20050249940A1 (en) | 2004-05-07 | 2005-11-10 | 3M Innovative Properties Company | Fluoropolyether poly(meth)acryl compounds |
| US7342080B2 (en) | 2004-05-07 | 2008-03-11 | 3M Innovative Properties Company | Polymerizable compositions, methods of making the same, and composite articles therefrom |
| WO2006049020A1 (ja) * | 2004-11-01 | 2006-05-11 | Daikin Industries, Ltd. | ガラス系基材処理用組成物 |
| US20060216524A1 (en) | 2005-03-23 | 2006-09-28 | 3M Innovative Properties Company | Perfluoropolyether urethane additives having (meth)acryl groups and hard coats |
| US7745653B2 (en) * | 2007-03-08 | 2010-06-29 | 3M Innovative Properties Company | Fluorochemical compounds having pendent silyl groups |
-
2007
- 2007-03-08 US US11/683,823 patent/US7745653B2/en not_active Expired - Fee Related
-
2008
- 2008-02-22 WO PCT/US2008/054655 patent/WO2008112400A2/en not_active Ceased
- 2008-02-22 CN CN2008800075617A patent/CN101679461B/zh not_active Expired - Fee Related
- 2008-02-22 JP JP2009552796A patent/JP5513133B2/ja not_active Expired - Fee Related
- 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 |
| JP2014111617A (ja) | 2014-06-19 |
| EP2134729A2 (en) | 2009-12-23 |
| WO2008112400A3 (en) | 2008-12-04 |
| CN101679461A (zh) | 2010-03-24 |
| US7745653B2 (en) | 2010-06-29 |
| WO2008112400A2 (en) | 2008-09-18 |
| WO2008112400A9 (en) | 2009-04-16 |
| EP2134729B1 (en) | 2013-12-04 |
| JP2010520296A (ja) | 2010-06-10 |
| US20080220264A1 (en) | 2008-09-11 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP5513133B2 (ja) | ペンダントシリル基を有するフルオロケミカル化合物 | |
| JP5346006B2 (ja) | マイケル付加化合物フルオロケミカルシラン | |
| JP5543344B2 (ja) | 側鎖シリル基を有するフルオロケミカルウレタン化合物 | |
| CN101501046B (zh) | 全氟聚醚硅烷及其用途 | |
| JP5074927B2 (ja) | 表面改質剤およびその用途 | |
| CN104945610B (zh) | 含有氟聚醚的聚合物改性的硅烷，表面处理剂和制品 | |
| JP5669699B2 (ja) | 表面改質剤 | |
| JP5453103B2 (ja) | 表面処理に使用される、側鎖シリル基を有するフルオロケミカルウレタン化合物 | |
| JP2010503020A (ja) | 反射防止物品 | |
| JP2003238577A (ja) | パーフルオロポリエーテル変性シラン及び表面処理剤、並びに反射防止フィルター | |
| US20050249956A1 (en) | Stain repellent optical hard coating | |
| WO2020246301A1 (ja) | フルオロポリエーテル基含有ポリマー及びその製造方法 | |
| WO2023042696A1 (ja) | フルオロポリエーテル基含有ポリマー、表面処理剤及び物品 | |
| WO2023199768A1 (ja) | フルオロポリエーテル基含有ポリマー、表面処理剤及び物品 | |
| CN109790443B (zh) | 表面处理剂、具有表面处理剂的硬化物的物品以及在物品的表面形成硬化被膜的方法 | |
| JP7321655B2 (ja) | 被膜の耐候性を評価する方法、該被膜の製膜方法及び該被膜を有する物品 | |
| WO2023248880A1 (ja) | フルオロポリエーテル基含有ポリマー、表面処理剤及び物品 | |
| WO2006049020A1 (ja) | ガラス系基材処理用組成物 | |
| WO2025182641A1 (ja) | フルオロポリエーテル基含有ポリマー組成物、コーティング剤及び物品、並びに物品の表面改質方法 | |
| WO2025229833A1 (ja) | フルオロポリエーテル基含有ポリマー組成物、表面処理剤及び物品 | |
| WO2025047304A1 (ja) | フルオロポリエーテル基含有ポリマー、表面処理剤及び物品 | |
| WO2025211106A1 (ja) | 炭化水素末端基含有化合物、表面処理剤及び物品 | |
| JP2000169489A (ja) | 含フッ素化合物及び防汚性物品 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20110126 |
|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20110126 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20130507 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20130806 |
|
| A02 | Decision of refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A02 Effective date: 20130924 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20140121 |
|
| A911 | Transfer to examiner for re-examination before appeal (zenchi) |
Free format text: JAPANESE INTERMEDIATE CODE: A911 Effective date: 20140130 |
|
| TRDD | Decision of grant or rejection written | ||
| A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20140225 |
|
| A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20140327 |
|
| R150 | Certificate of patent or registration of utility model |
Ref document number: 5513133 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| LAPS | Cancellation because of no payment of annual fees |