DE60223069T2 - Beschichtungzusammensetzungen umfassend polykondensate aus fluorchemischen polyethersilanen und ihre verwendung - Google Patents
Beschichtungzusammensetzungen umfassend polykondensate aus fluorchemischen polyethersilanen und ihre verwendung Download PDFInfo
- Publication number
- DE60223069T2 DE60223069T2 DE60223069T DE60223069T DE60223069T2 DE 60223069 T2 DE60223069 T2 DE 60223069T2 DE 60223069 T DE60223069 T DE 60223069T DE 60223069 T DE60223069 T DE 60223069T DE 60223069 T2 DE60223069 T2 DE 60223069T2
- Authority
- DE
- Germany
- Prior art keywords
- group
- groups
- hydrolyzable
- composition according
- composition
- 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 - Lifetime
Links
- 239000008199 coating composition Substances 0.000 title claims description 10
- 239000000203 mixture Substances 0.000 claims abstract description 81
- 239000000758 substrate Substances 0.000 claims abstract description 48
- 150000001875 compounds Chemical class 0.000 claims abstract description 47
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 29
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 13
- 239000007859 condensation product Substances 0.000 claims abstract description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 45
- 238000000576 coating method Methods 0.000 claims description 29
- 239000011248 coating agent Substances 0.000 claims description 19
- 238000006243 chemical reaction Methods 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 16
- 125000000524 functional group Chemical group 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 238000006482 condensation reaction Methods 0.000 claims description 12
- 239000010702 perfluoropolyether Substances 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 12
- 239000003054 catalyst Substances 0.000 claims description 10
- 125000005647 linker group Chemical group 0.000 claims description 10
- 229910052710 silicon Inorganic materials 0.000 claims description 10
- 229910052719 titanium Inorganic materials 0.000 claims description 10
- 229910052726 zirconium Inorganic materials 0.000 claims description 10
- 229910052782 aluminium Inorganic materials 0.000 claims description 9
- 229910052796 boron Inorganic materials 0.000 claims description 8
- 229910052732 germanium Inorganic materials 0.000 claims description 8
- 229910052745 lead Inorganic materials 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- 229910052718 tin Inorganic materials 0.000 claims description 8
- 229910052720 vanadium Inorganic materials 0.000 claims description 8
- 239000011521 glass Substances 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 229910052725 zinc Inorganic materials 0.000 claims description 7
- 239000004971 Cross linker Substances 0.000 claims description 6
- 239000000919 ceramic Substances 0.000 claims description 6
- 230000005494 condensation Effects 0.000 claims description 6
- 125000004122 cyclic group Chemical group 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 238000002156 mixing Methods 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 238000009833 condensation Methods 0.000 claims description 5
- 229910052751 metal Inorganic materials 0.000 claims description 5
- 239000002184 metal Substances 0.000 claims description 5
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 4
- 229920001774 Perfluoroether Polymers 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 238000004132 cross linking Methods 0.000 claims description 4
- 125000005515 organic divalent group Chemical group 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 4
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 150000004820 halides Chemical group 0.000 claims description 2
- 230000008569 process Effects 0.000 claims description 2
- 125000004423 acyloxy group Chemical group 0.000 claims 1
- -1 silane compound Chemical class 0.000 abstract description 16
- 239000004721 Polyphenylene oxide Substances 0.000 abstract description 7
- 229920000570 polyether Polymers 0.000 abstract description 7
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical group [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 abstract description 6
- 229910000077 silane Inorganic materials 0.000 abstract description 5
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- 238000005299 abrasion Methods 0.000 description 15
- 239000003960 organic solvent Substances 0.000 description 15
- 101150041213 FES1 gene Proteins 0.000 description 11
- 239000003921 oil Substances 0.000 description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 239000000463 material Substances 0.000 description 9
- DCAYPVUWAIABOU-UHFFFAOYSA-N hexadecane Chemical compound CCCCCCCCCCCCCCCC DCAYPVUWAIABOU-UHFFFAOYSA-N 0.000 description 8
- 150000002430 hydrocarbons Chemical group 0.000 description 8
- 239000003999 initiator Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 125000004429 atom Chemical group 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 150000005690 diesters Chemical class 0.000 description 6
- 230000007062 hydrolysis Effects 0.000 description 6
- 238000006460 hydrolysis reaction Methods 0.000 description 6
- 230000002940 repellent Effects 0.000 description 6
- 239000005871 repellent Substances 0.000 description 6
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 125000003709 fluoroalkyl group Chemical group 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- SJECZPVISLOESU-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN SJECZPVISLOESU-UHFFFAOYSA-N 0.000 description 4
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 238000004140 cleaning Methods 0.000 description 4
- 239000011737 fluorine Substances 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 125000005843 halogen group Chemical group 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- 125000005842 heteroatom Chemical group 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 125000000962 organic group Chemical group 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 238000006068 polycondensation reaction Methods 0.000 description 4
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 101100324822 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) fes-4 gene Proteins 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 210000003298 dental enamel Anatomy 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 238000003682 fluorination reaction Methods 0.000 description 3
- 239000008240 homogeneous mixture Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000003791 organic solvent mixture Substances 0.000 description 3
- 125000005702 oxyalkylene group Chemical group 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 238000005191 phase separation Methods 0.000 description 3
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 3
- 239000004926 polymethyl methacrylate Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 239000002023 wood Substances 0.000 description 3
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 description 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- FMGBDYLOANULLW-UHFFFAOYSA-N 3-isocyanatopropyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)CCCN=C=O FMGBDYLOANULLW-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
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 229910000831 Steel Inorganic materials 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000007259 addition reaction Methods 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 125000000732 arylene group Chemical group 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 2
- 239000012965 benzophenone Substances 0.000 description 2
- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical compound C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 description 2
- 230000001680 brushing effect Effects 0.000 description 2
- 125000006363 carbonyl oxy alkylene group Chemical group 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 125000002993 cycloalkylene group Chemical group 0.000 description 2
- PZPGRFITIJYNEJ-UHFFFAOYSA-N disilane Chemical compound [SiH3][SiH3] PZPGRFITIJYNEJ-UHFFFAOYSA-N 0.000 description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-M methacrylate group Chemical group C(C(=C)C)(=O)[O-] CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 230000000737 periodic effect Effects 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 238000010526 radical polymerization reaction Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 150000004756 silanes Chemical class 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000010959 steel Substances 0.000 description 2
- 238000007039 two-step reaction Methods 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 125000006736 (C6-C20) aryl group Chemical group 0.000 description 1
- OKIYQFLILPKULA-UHFFFAOYSA-N 1,1,1,2,2,3,3,4,4-nonafluoro-4-methoxybutane Chemical compound COC(F)(F)C(F)(F)C(F)(F)C(F)(F)F OKIYQFLILPKULA-UHFFFAOYSA-N 0.000 description 1
- NVSXSBBVEDNGPY-UHFFFAOYSA-N 1,1,1,2,2-pentafluorobutane Chemical compound CCC(F)(F)C(F)(F)F NVSXSBBVEDNGPY-UHFFFAOYSA-N 0.000 description 1
- DFUYAWQUODQGFF-UHFFFAOYSA-N 1-ethoxy-1,1,2,2,3,3,4,4,4-nonafluorobutane Chemical compound CCOC(F)(F)C(F)(F)C(F)(F)C(F)(F)F DFUYAWQUODQGFF-UHFFFAOYSA-N 0.000 description 1
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- XDLMVUHYZWKMMD-UHFFFAOYSA-N 3-trimethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C(C)=C XDLMVUHYZWKMMD-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 1
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000003926 acrylamides Chemical class 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 230000002730 additional effect Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical group 0.000 description 1
- 230000003373 anti-fouling effect Effects 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 239000002969 artificial stone Substances 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 239000012933 diacyl peroxide Substances 0.000 description 1
- 239000012975 dibutyltin dilaurate Substances 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- YYLGKUPAFFKGRQ-UHFFFAOYSA-N dimethyldiethoxysilane Chemical compound CCO[Si](C)(C)OCC YYLGKUPAFFKGRQ-UHFFFAOYSA-N 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 208000001848 dysentery Diseases 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- XGZNHFPFJRZBBT-UHFFFAOYSA-N ethanol;titanium Chemical compound [Ti].CCO.CCO.CCO.CCO XGZNHFPFJRZBBT-UHFFFAOYSA-N 0.000 description 1
- FWDBOZPQNFPOLF-UHFFFAOYSA-N ethenyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)C=C FWDBOZPQNFPOLF-UHFFFAOYSA-N 0.000 description 1
- NKSJNEHGWDZZQF-UHFFFAOYSA-N ethenyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C=C NKSJNEHGWDZZQF-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 1
- XPBBUZJBQWWFFJ-UHFFFAOYSA-N fluorosilane Chemical compound [SiH3]F XPBBUZJBQWWFFJ-UHFFFAOYSA-N 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- PGFXOWRDDHCDTE-UHFFFAOYSA-N hexafluoropropylene oxide Chemical compound FC(F)(F)C1(F)OC1(F)F PGFXOWRDDHCDTE-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- LOTBYPQQWICYBB-UHFFFAOYSA-N methyl n-hexyl-n-[2-(hexylamino)ethyl]carbamate Chemical compound CCCCCCNCCN(C(=O)OC)CCCCCC LOTBYPQQWICYBB-UHFFFAOYSA-N 0.000 description 1
- 229940104873 methyl perfluorobutyl ether Drugs 0.000 description 1
- 239000005055 methyl trichlorosilane Substances 0.000 description 1
- JLUFWMXJHAVVNN-UHFFFAOYSA-N methyltrichlorosilane Chemical compound C[Si](Cl)(Cl)Cl JLUFWMXJHAVVNN-UHFFFAOYSA-N 0.000 description 1
- 125000006606 n-butoxy group Chemical group 0.000 description 1
- 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 230000006855 networking Effects 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- SLYCYWCVSGPDFR-UHFFFAOYSA-N octadecyltrimethoxysilane Chemical compound CCCCCCCCCCCCCCCCCC[Si](OC)(OC)OC SLYCYWCVSGPDFR-UHFFFAOYSA-N 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 150000003961 organosilicon compounds Chemical class 0.000 description 1
- UCUUFSAXZMGPGH-UHFFFAOYSA-N penta-1,4-dien-3-one Chemical class C=CC(=O)C=C UCUUFSAXZMGPGH-UHFFFAOYSA-N 0.000 description 1
- 229960004624 perflexane Drugs 0.000 description 1
- 125000006551 perfluoro alkylene group Chemical group 0.000 description 1
- ZJIJAJXFLBMLCK-UHFFFAOYSA-N perfluorohexane Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F ZJIJAJXFLBMLCK-UHFFFAOYSA-N 0.000 description 1
- YVBBRRALBYAZBM-UHFFFAOYSA-N perfluorooctane Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F YVBBRRALBYAZBM-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 125000005634 peroxydicarbonate group Chemical group 0.000 description 1
- 230000002085 persistent effect Effects 0.000 description 1
- 238000005498 polishing Methods 0.000 description 1
- 229920002285 poly(styrene-co-acrylonitrile) Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- XPGAWFIWCWKDDL-UHFFFAOYSA-N propan-1-olate;zirconium(4+) Chemical compound [Zr+4].CCC[O-].CCC[O-].CCC[O-].CCC[O-] XPGAWFIWCWKDDL-UHFFFAOYSA-N 0.000 description 1
- BCWYYHBWCZYDNB-UHFFFAOYSA-N propan-2-ol;zirconium Chemical compound [Zr].CC(C)O.CC(C)O.CC(C)O.CC(C)O BCWYYHBWCZYDNB-UHFFFAOYSA-N 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000002310 reflectometry Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 125000005372 silanol group Chemical group 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 150000003377 silicon compounds Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 125000004354 sulfur functional group Chemical group 0.000 description 1
- 239000012756 surface treatment agent Substances 0.000 description 1
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- LFQCEHFDDXELDD-UHFFFAOYSA-N tetramethyl orthosilicate Chemical compound CO[Si](OC)(OC)OC LFQCEHFDDXELDD-UHFFFAOYSA-N 0.000 description 1
- 238000007669 thermal treatment Methods 0.000 description 1
- JMXKSZRRTHPKDL-UHFFFAOYSA-N titanium(IV) ethoxide Substances [Ti+4].CC[O-].CC[O-].CC[O-].CC[O-] JMXKSZRRTHPKDL-UHFFFAOYSA-N 0.000 description 1
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 1
- 239000012780 transparent material Substances 0.000 description 1
- GQIUQDDJKHLHTB-UHFFFAOYSA-N trichloro(ethenyl)silane Chemical compound Cl[Si](Cl)(Cl)C=C GQIUQDDJKHLHTB-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
- FZMJEGJVKFTGMU-UHFFFAOYSA-N triethoxy(octadecyl)silane Chemical compound CCCCCCCCCCCCCCCCCC[Si](OCC)(OCC)OCC FZMJEGJVKFTGMU-UHFFFAOYSA-N 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000005050 vinyl trichlorosilane Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- 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
- C08G65/002—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from unsaturated compounds
- C08G65/005—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from unsaturated compounds containing halogens
- C08G65/007—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from unsaturated compounds containing halogens containing fluorine
-
- 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
- C08G65/336—Polymers modified by chemical after-treatment with organic compounds containing silicon
-
- 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]
- Y10T428/31551—Of polyamidoester [polyurethane, polyisocyanate, polycarbamate, etc.]
- Y10T428/31609—Particulate metal or metal compound-containing
- Y10T428/31612—As silicone, silane or siloxane
-
- 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)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Paints Or Removers (AREA)
- Silicon Polymers (AREA)
- Materials Applied To Surfaces To Minimize Adherence Of Mist Or Water (AREA)
- Polyethers (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10144 | 2001-11-08 | ||
| US10/010,144 US6649272B2 (en) | 2001-11-08 | 2001-11-08 | Coating composition comprising fluorochemical polyether silane polycondensate and use thereof |
| PCT/US2002/027331 WO2003040209A1 (en) | 2001-11-08 | 2002-08-27 | Coating composition comprising fluorochemical polyether silane polycondensate and use thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE60223069D1 DE60223069D1 (de) | 2007-11-29 |
| DE60223069T2 true DE60223069T2 (de) | 2008-08-07 |
Family
ID=21744145
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE60223069T Expired - Lifetime DE60223069T2 (de) | 2001-11-08 | 2002-08-27 | Beschichtungzusammensetzungen umfassend polykondensate aus fluorchemischen polyethersilanen und ihre verwendung |
Country Status (8)
| Country | Link |
|---|---|
| US (2) | US6649272B2 (enExample) |
| EP (1) | EP1444289B1 (enExample) |
| JP (1) | JP2005508420A (enExample) |
| CN (1) | CN1297586C (enExample) |
| AT (1) | ATE376021T1 (enExample) |
| DE (1) | DE60223069T2 (enExample) |
| ES (1) | ES2292800T3 (enExample) |
| WO (1) | WO2003040209A1 (enExample) |
Families Citing this family (103)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2816622A1 (fr) * | 2000-11-15 | 2002-05-17 | Atofina | Copolymeres fluores pour le traitement hydrophobe et oleophobe des materiaux de construction |
| ES2282186T3 (es) * | 2001-01-19 | 2007-10-16 | 3M Innovative Properties Company | Silanos fluoroquimicos solubles en agua o dispersables en agua para hacer que un sustrato sea repelente al aceite y al agua. |
| ATE432298T1 (de) * | 2001-01-19 | 2009-06-15 | 3M Innovative Properties Co | Fluorovinyloligomerkomponente mit silangruppen, flüssigzusammensetzungen daraus und beschichtungsverfahren |
| CN1209392C (zh) | 2001-05-14 | 2005-07-06 | 阿姆诺洼化学有限公司 | 由含侧氟碳基的环状单体得到的聚合物表面活性剂 |
| EP1262464B1 (en) | 2001-05-29 | 2004-09-29 | 3M Innovative Properties Company | Grout powder having been admixed with a fluorochemical compound |
| US20040191481A1 (en) * | 2001-05-31 | 2004-09-30 | Volker Erb | Reflective sheet treated with fluorosilane |
| US6716534B2 (en) * | 2001-11-08 | 2004-04-06 | 3M Innovative Properties Company | Coating composition comprising a fluorochemical polyether silane partial condensate and use thereof |
| US6649272B2 (en) * | 2001-11-08 | 2003-11-18 | 3M Innovative Properties Company | Coating composition comprising fluorochemical polyether silane polycondensate and use thereof |
| EP1369453B1 (en) * | 2002-06-03 | 2006-11-29 | 3M Innovative Properties Company | Fluoro-Silane-Oligomer composition |
| US20040112862A1 (en) * | 2002-12-12 | 2004-06-17 | Molecular Imprints, Inc. | Planarization composition and method of patterning a substrate using the same |
| US7365103B2 (en) * | 2002-12-12 | 2008-04-29 | Board Of Regents, The University Of Texas System | Compositions for dark-field polymerization and method of using the same for imprint lithography processes |
| US7122079B2 (en) | 2004-02-27 | 2006-10-17 | Molecular Imprints, Inc. | Composition for an etching mask comprising a silicon-containing material |
| US7396475B2 (en) | 2003-04-25 | 2008-07-08 | Molecular Imprints, Inc. | Method of forming stepped structures employing imprint lithography |
| US20060108710A1 (en) * | 2004-11-24 | 2006-05-25 | Molecular Imprints, Inc. | Method to reduce adhesion between a conformable region and a mold |
| US7307118B2 (en) * | 2004-11-24 | 2007-12-11 | Molecular Imprints, Inc. | Composition to reduce adhesion between a conformable region and a mold |
| US7157036B2 (en) | 2003-06-17 | 2007-01-02 | Molecular Imprints, Inc | Method to reduce adhesion between a conformable region and a pattern of a mold |
| US20050160934A1 (en) | 2004-01-23 | 2005-07-28 | Molecular Imprints, Inc. | Materials and methods for imprint lithography |
| DE10339912B4 (de) * | 2003-08-29 | 2016-07-21 | Ivoclar Vivadent Ag | Dentale Beschichtungsmaterialien, deren Verwendung sowie Verfahren zur Beschichtung einer Substratoberfläche |
| US7652115B2 (en) * | 2003-09-08 | 2010-01-26 | 3M Innovative Properties Company | Fluorinated polyether isocyanate derived silane compositions |
| US8030430B2 (en) | 2003-10-06 | 2011-10-04 | 3M Innovative Properties Company | Stain resistant polyurethane coatings |
| US7122482B2 (en) * | 2003-10-27 | 2006-10-17 | Molecular Imprints, Inc. | Methods for fabricating patterned features utilizing imprint lithography |
| US7141537B2 (en) * | 2003-10-30 | 2006-11-28 | 3M Innovative Properties Company | Mixture of fluorinated polyethers and use thereof as surfactant |
| US7803894B2 (en) * | 2003-12-05 | 2010-09-28 | 3M Innovatie Properties Company | Coating compositions with perfluoropolyetherisocyanate derived silane and alkoxysilanes |
| US8076386B2 (en) | 2004-02-23 | 2011-12-13 | Molecular Imprints, Inc. | Materials for imprint lithography |
| US7906180B2 (en) | 2004-02-27 | 2011-03-15 | Molecular Imprints, Inc. | Composition for an etching mask comprising a silicon-containing material |
| US7939131B2 (en) | 2004-08-16 | 2011-05-10 | Molecular Imprints, Inc. | Method to provide a layer with uniform etch characteristics |
| US7282550B2 (en) * | 2004-08-16 | 2007-10-16 | Molecular Imprints, Inc. | Composition to provide a layer with uniform etch characteristics |
| US20060062922A1 (en) | 2004-09-23 | 2006-03-23 | Molecular Imprints, Inc. | Polymerization technique to attenuate oxygen inhibition of solidification of liquids and composition therefor |
| JP4803342B2 (ja) * | 2004-10-19 | 2011-10-26 | 信越化学工業株式会社 | 耐擦傷性表面被膜形成用シリコーンコーティング組成物及びそれを用いた被覆物品 |
| US7292326B2 (en) | 2004-11-30 | 2007-11-06 | Molecular Imprints, Inc. | Interferometric analysis for the manufacture of nano-scale devices |
| US8557351B2 (en) | 2005-07-22 | 2013-10-15 | Molecular Imprints, Inc. | Method for adhering materials together |
| US8808808B2 (en) | 2005-07-22 | 2014-08-19 | Molecular Imprints, Inc. | Method for imprint lithography utilizing an adhesion primer layer |
| US7759407B2 (en) | 2005-07-22 | 2010-07-20 | Molecular Imprints, Inc. | Composition for adhering materials together |
| FR2889183B1 (fr) | 2005-07-26 | 2007-09-07 | Saint Gobain | Revetement hydrophobe comprenant un primage comprenant un disilane et une couche hydrophobe comprenant un alkysilane fluore |
| US8142703B2 (en) * | 2005-10-05 | 2012-03-27 | Molecular Imprints, Inc. | Imprint lithography method |
| US7728098B2 (en) | 2006-07-27 | 2010-06-01 | 3M Innovative Properties Company | Fluorochemical composition comprising fluorinated oligomeric silane |
| KR101249219B1 (ko) * | 2006-09-29 | 2013-04-03 | 삼성전자주식회사 | 공중합체, 뱅크 형성용 조성물 및 이를 이용한 뱅크 형성방법 |
| ATE458839T1 (de) * | 2006-10-20 | 2010-03-15 | 3M Innovative Properties Co | Verfahren für leicht zu reinigende substrate und artikel daraus |
| US7847015B2 (en) * | 2006-11-15 | 2010-12-07 | Shin-Etsu Chemical Co., Ltd. | Coating composition |
| CA2671755C (en) * | 2006-12-07 | 2016-06-14 | 3M Innovative Properties Company | Particles comprising a fluorinated siloxane and methods of making and using the same |
| WO2008076639A1 (en) * | 2006-12-20 | 2008-06-26 | 3M Innovative Properties Company | Fluorochemical urethane compounds having pendent silyl groups |
| EP2116350A4 (en) * | 2007-02-07 | 2011-06-22 | Asahi Glass Co Ltd | PRINTING FORM AND MANUFACTURING METHOD THEREFOR |
| US7745653B2 (en) * | 2007-03-08 | 2010-06-29 | 3M Innovative Properties Company | Fluorochemical compounds having pendent silyl groups |
| KR20100017848A (ko) * | 2007-05-23 | 2010-02-16 | 쓰리엠 이노베이티브 프로퍼티즈 컴파니 | 플루오르화 계면활성제의 수성 조성물 및 그의 사용 방법 |
| CN101679569A (zh) | 2007-06-06 | 2010-03-24 | 3M创新有限公司 | 氟化醚组合物以及使用该组合物的方法 |
| US8015970B2 (en) * | 2007-07-26 | 2011-09-13 | 3M Innovative Properties Company | Respirator, welding helmet, or face shield that has low surface energy hard-coat lens |
| US7897678B2 (en) * | 2007-07-26 | 2011-03-01 | 3M Innovative Properties Company | Fluorochemical urethane compounds having pendent silyl groups |
| KR101439538B1 (ko) * | 2007-08-14 | 2014-09-12 | 삼성전자주식회사 | 보호막 형성용 조성물 및 이에 의한 보호막을 포함한유기박막 트랜지스터 |
| EP2203516B1 (en) * | 2007-10-01 | 2013-10-23 | 3M Innovative Properties Company | Compositions comprising cationic fluorinated ether-silanes, and related methods |
| US8080170B2 (en) * | 2007-10-01 | 2011-12-20 | 3M Innovative Properties Company | Cationic fluorinated ether silane compositions and related methods |
| JP5571560B2 (ja) * | 2007-11-06 | 2014-08-13 | スリーエム イノベイティブ プロパティズ カンパニー | 医薬品吸入装置及びそれらの構成要素 |
| GB0721737D0 (en) * | 2007-11-06 | 2007-12-19 | 3M Innovative Properties Co | Medicinal inhalation devices and components thereof |
| WO2009073547A2 (en) * | 2007-12-03 | 2009-06-11 | 3M Innovative Properties Company | Cationic polymeric fluorinated ether silane compositions and methods of use |
| US8378018B2 (en) * | 2007-12-03 | 2013-02-19 | 3M Innovative Properties Company | Cationic polymeric fluorinated ether silane compositions and methods of use |
| KR20100122903A (ko) * | 2008-02-12 | 2010-11-23 | 후지필름 가부시키가이샤 | 함불소 다관능 규소 화합물 및 함불소 다관능 규소 화합물의 제조 방법 |
| EP2269116A4 (en) * | 2008-03-11 | 2011-09-07 | 3M Innovative Properties Co | PHOTOGRAPHIC MASKS HAVING PROTECTIVE LAYER |
| US8043421B2 (en) * | 2008-03-12 | 2011-10-25 | E.I. Du Pont De Nemours & Company | Durable automotive windshield coating and the use thereof |
| EA201100051A1 (ru) * | 2008-07-18 | 2011-08-30 | Зм Инновейтив Пропертиз Компани | Фторсодержащие простые эфиры силанов и способы их использования |
| MX2011000702A (es) * | 2008-07-18 | 2011-02-24 | 3M Innovative Properties Co | Compuestos de eter fluorados y metodos para usar los mismos. |
| JP5357502B2 (ja) * | 2008-10-28 | 2013-12-04 | パナソニック株式会社 | 低屈折率コーティング材組成物及び塗装品 |
| US20100109195A1 (en) | 2008-11-05 | 2010-05-06 | Molecular Imprints, Inc. | Release agent partition control in imprint lithography |
| WO2010080473A1 (en) | 2008-12-18 | 2010-07-15 | 3M Innovative Properties Company | Method of contacting hydrocarbon-bearing formations with fluorinated ether compositions |
| KR101247228B1 (ko) * | 2008-12-26 | 2013-03-25 | 가부시키가이샤 무라타 세이사쿠쇼 | 세라믹 전자부품의 제조 방법 및 세라믹 전자부품 |
| CN102597116B (zh) | 2009-07-21 | 2013-12-11 | 3M创新有限公司 | 可固化组合物、涂覆底片的方法、以及被涂覆的底片 |
| CN102549042B (zh) | 2009-09-16 | 2015-01-28 | 3M创新有限公司 | 氟化涂料和用其制作的底片 |
| US8420281B2 (en) | 2009-09-16 | 2013-04-16 | 3M Innovative Properties Company | Epoxy-functionalized perfluoropolyether polyurethanes |
| US8748060B2 (en) | 2009-09-16 | 2014-06-10 | 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 |
| WO2012024005A2 (en) * | 2010-07-09 | 2012-02-23 | Luna Innovations Incorporated | Coating systems capable of forming ambiently cured highly durable hydrophobic coatings on substrates |
| US20130229378A1 (en) * | 2010-11-10 | 2013-09-05 | Suresh S. Iyer | Optical device surface treatment process and smudge-resistant article produced thereby |
| EP2638117B1 (en) * | 2010-11-10 | 2015-09-23 | 3M Innovative Properties Company | Surface treatment process, composition for use therein, and treated article |
| JP2012157856A (ja) * | 2011-01-13 | 2012-08-23 | Central Glass Co Ltd | 防汚性物品及びその製造方法 |
| US9035082B2 (en) | 2011-10-10 | 2015-05-19 | Cytonix, Llc | Low surface energy touch screens, coatings, and methods |
| CN104114564B (zh) * | 2012-02-17 | 2017-06-30 | 旭硝子株式会社 | 含氟醚化合物、含氟醚组合物及涂覆液以及具有表面处理层的基材及其制造方法 |
| TWI579347B (zh) | 2012-02-17 | 2017-04-21 | Asahi Glass Co Ltd | A fluorine-containing ether compound, a fluorine-containing ether composition and a coating liquid, and a substrate having a surface treatment layer and a method for producing the same (3) |
| EP2816045B1 (en) * | 2012-02-17 | 2019-04-03 | AGC Inc. | Fluorinated ether compound, fluorinated ether composition and coating fluid, and substrate having surface-treated layer and method for its production |
| KR20150023794A (ko) * | 2012-06-18 | 2015-03-05 | 이노바 다이나믹스, 인코포레이티드 | 용기에 보관된 나노와이어 현탁액 중의 응집체 감소 |
| US9062213B2 (en) | 2013-03-12 | 2015-06-23 | Dow Corning Corporation | Non-aqueous emulsions and methods of preparing surface-treated articles |
| KR20160061348A (ko) * | 2013-09-16 | 2016-05-31 | 허니웰 인터내셔날 인코포레이티드 | 폴리 플루오르 함유 실록산 코팅 |
| WO2015051053A1 (en) * | 2013-10-04 | 2015-04-09 | Luna Innovations Incorporated | Transparent hydrophobic coating materials with improved durability and methods of making same |
| TW201602248A (zh) * | 2014-03-17 | 2016-01-16 | 道康寧公司 | 非水性乳液及以其製備經表面處理之物品的方法 |
| WO2015142562A1 (en) * | 2014-03-17 | 2015-09-24 | Dow Corning Corporation | Method of preparing non-aqueous emulsion, non-aqueous emulsion prepared thereby, and methods of preparing surface-treated articles |
| WO2015142559A1 (en) * | 2014-03-17 | 2015-09-24 | Dow Corning Corporation | Fluorinated compound, fluorinated polymer formed from same, curable composition comprising the fluorinated polymer, and cured product |
| WO2016004195A1 (en) * | 2014-07-02 | 2016-01-07 | Cytonix, Llc | Hydrophobic coating composition comprising alkoxy silane monomer and fluorinated monomer in an organic solvent |
| JP6398500B2 (ja) * | 2014-09-10 | 2018-10-03 | 信越化学工業株式会社 | 含フッ素コーティング剤及び該コーティング剤で処理された物品 |
| CA2966343A1 (en) | 2014-10-28 | 2016-05-06 | 3M Innovative Properties Company | Spray application system components comprising a repellent surface & methods |
| JP6784023B2 (ja) * | 2014-12-26 | 2020-11-11 | 大日本印刷株式会社 | 組成物、該組成物を用いた部材、及びその製造方法、並びに該部材を備えたタッチパネル |
| CN108348937A (zh) | 2015-10-28 | 2018-07-31 | 3M创新有限公司 | 包括拒液表面的喷雾施用系统部件和方法 |
| EP3368618B1 (en) | 2015-10-28 | 2020-11-25 | 3M Innovative Properties Company | Articles subject to ice formation comprising a repellent surface |
| WO2017189475A1 (en) | 2016-04-26 | 2017-11-02 | 3M Innovative Properties Company | Articles subject to ice formation comprising a repellent surface comprising a siloxane material |
| CN108239193B (zh) * | 2016-12-26 | 2023-07-04 | 重庆鑫景特种玻璃有限公司 | 一种全氟聚醚硅烷树枝状化合物及其制备方法和包含其的薄膜 |
| US10544260B2 (en) | 2017-08-30 | 2020-01-28 | Ppg Industries Ohio, Inc. | Fluoropolymers, methods of preparing fluoropolymers, and coating compositions containing fluoropolymers |
| JP7063335B2 (ja) * | 2017-08-31 | 2022-05-09 | Agc株式会社 | 含フッ素エーテル化合物、含フッ素エーテル組成物、コーティング液、物品およびその製造方法 |
| US11629267B2 (en) * | 2017-10-31 | 2023-04-18 | Daikin Industries, Ltd. | Curable composition |
| CN111670208B (zh) * | 2018-02-02 | 2025-02-07 | 大金工业株式会社 | 含氟代(聚)醚基的硅烷化合物 |
| CN109071793B (zh) * | 2018-05-16 | 2019-12-31 | 广州优尔材料科技有限公司 | 含全氟聚醚基的硅烷化合物、其制备方法、表面处理剂及物品 |
| KR102268922B1 (ko) | 2018-05-16 | 2021-06-24 | 광저우 유알 매터리얼 테크놀로지 컴퍼니 리미티드 | 퍼플루오로폴리에테르기 함유 실란화합물, 이의 제조방법, 표면처리제 및 물품 |
| CN110922582B (zh) * | 2018-09-20 | 2023-06-09 | 东莞东阳光科研发有限公司 | 一种全氟聚醚硅氧烷化合物及其制备方法和应用 |
| US12187914B2 (en) | 2018-11-13 | 2025-01-07 | Basf Se | Easy to clean coating |
| JP2022017617A (ja) * | 2018-11-13 | 2022-01-26 | Agc株式会社 | 含フッ素エーテル組成物、コーティング液、物品およびその製造方法 |
| KR102810225B1 (ko) * | 2019-03-13 | 2025-05-19 | 삼성전자주식회사 | 표면 코팅재, 필름, 적층체, 표시 장치, 물품 및 코팅 공정 |
| JP7330883B2 (ja) * | 2019-12-27 | 2023-08-22 | 株式会社ネオス | コーティング組成物及びコーティングを備えた物品 |
| CN116891568B (zh) * | 2023-06-08 | 2025-04-08 | 东华大学 | 一种全氟聚醚硼酸化合物、表面处理剂及其制备和应用 |
Family Cites Families (38)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3810874A (en) | 1969-03-10 | 1974-05-14 | Minnesota Mining & Mfg | Polymers prepared from poly(perfluoro-alkylene oxide) compounds |
| BR7105885D0 (pt) * | 1970-09-08 | 1973-03-13 | Minnesota Mining & Mfg | Processo para preparar alfa omegadi-(s-triazinil-dissubstituido)-n-perfluor polioxa-alcanos |
| JPS521926B2 (enExample) | 1974-03-25 | 1977-01-19 | ||
| US3950588A (en) * | 1974-11-01 | 1976-04-13 | Minnesota Mining And Manufacturing Company | Coating of silanol-reactive surfaces with di-silyl poly(perfluorooxyalkylenes) |
| JPS5331455A (en) * | 1976-09-06 | 1978-03-24 | Matsushita Electric Works Ltd | Electrically-driven toothbrush |
| JPS6040254A (ja) * | 1983-08-16 | 1985-03-02 | 旭硝子株式会社 | 撥水撥油性多層膜 |
| US4614667A (en) | 1984-05-21 | 1986-09-30 | Minnesota Mining And Manufacturing Company | Composite low surface energy liner of perfluoropolyether |
| DE3583707D1 (de) | 1984-06-26 | 1991-09-12 | Asahi Glass Co Ltd | Durchsichtiger schwer schmutzender gegenstand mit niedriger reflexion. |
| GB2218097A (en) | 1988-04-26 | 1989-11-08 | Mitsubishi Metal Corp | Perfluoroalkylsulphonamidoalkyl silanes; surface treatment agents |
| AU632869B2 (en) | 1989-12-14 | 1993-01-14 | Minnesota Mining And Manufacturing Company | Fluorocarbon-based coating compositions and articles derived therefrom |
| JPH04342444A (ja) * | 1991-05-17 | 1992-11-27 | Asahi Glass Co Ltd | 表面処理された輸送機器用物品および該物品の製造方法 |
| DE4118184A1 (de) | 1991-06-03 | 1992-12-10 | Inst Neue Mat Gemein Gmbh | Beschichtungszusammensetzungen auf der basis von fluorhaltigen anorganischen polykondensaten, deren herstellung und deren verwendung |
| JP2877616B2 (ja) | 1992-05-29 | 1999-03-31 | 信越化学工業株式会社 | 親水撥油処理剤 |
| US5274159A (en) | 1993-02-18 | 1993-12-28 | Minnesota Mining And Manufacturing Company | Destructable fluorinated alkoxysilane surfactants and repellent coatings derived therefrom |
| JPH0753919A (ja) * | 1993-08-11 | 1995-02-28 | Shin Etsu Chem Co Ltd | 常温硬化性組成物 |
| US5488142A (en) | 1993-10-04 | 1996-01-30 | Minnesota Mining And Manufacturing Company | Fluorination in tubular reactor system |
| US5658962A (en) | 1994-05-20 | 1997-08-19 | Minnesota Mining And Manufacturing Company | Omega-hydrofluoroalkyl ethers, precursor carboxylic acids and derivatives thereof, and their preparation and application |
| JP3196621B2 (ja) | 1995-04-20 | 2001-08-06 | 信越化学工業株式会社 | 水溶性表面処理剤 |
| EP0745604A3 (en) | 1995-05-29 | 1998-07-29 | Shin-Etsu Chemical Co., Ltd. | Room temperature curable fluoropolymer composition; and fluorine-containing organosilicon compounds, a method of producing the same, and room temperature curable silicone composition containing the same |
| JP3121245B2 (ja) * | 1995-09-14 | 2000-12-25 | 信越化学工業株式会社 | 含フッ素有機ケイ素化合物及びその製造方法並びにそれを含有する室温硬化性シリコーン組成物 |
| DE69624923T2 (de) * | 1995-08-11 | 2003-08-21 | Daikin Industries, Ltd. | Silizium enthaltende organische fluorpolymere und ihre verwendung |
| JP3344199B2 (ja) | 1996-03-21 | 2002-11-11 | ソニー株式会社 | 防汚膜形成用組成物および反射防止フィルター |
| JP3709632B2 (ja) * | 1996-11-20 | 2005-10-26 | ソニー株式会社 | 反射防止フィルタおよびその製造方法ならびにこの反射防止フィルタを用いた表示装置 |
| DE19649953A1 (de) | 1996-12-03 | 1998-06-04 | Huels Chemische Werke Ag | Fluoralkyl-funktionelle Organopolysiloxan-haltige Zusammensetzungen auf Wasserbasis, Verfahren zu deren Herstellung sowie deren Verwendung |
| EP0978524B1 (en) | 1997-04-30 | 2005-12-14 | Daikin Industries, Limited | Fluoropolymer, process for preparing the same, and use thereof |
| DE19730245B4 (de) | 1997-07-15 | 2007-08-30 | W.L. Gore & Associates Gmbh | Beschichtungsmaterial, beschichtetes Material und Verfahren zu deren Herstellung |
| US6277485B1 (en) | 1998-01-27 | 2001-08-21 | 3M Innovative Properties Company | Antisoiling coatings for antireflective surfaces and methods of preparation |
| JP4733798B2 (ja) | 1998-01-31 | 2011-07-27 | 凸版印刷株式会社 | 防汚剤、防汚層の形成方法、光学部材、反射防止光学部材、光学機能性部材及び表示装置 |
| JP3712031B2 (ja) | 1998-02-23 | 2005-11-02 | 信越化学工業株式会社 | 硬化性組成物 |
| JP3567732B2 (ja) | 1998-04-28 | 2004-09-22 | 株式会社日立製作所 | 燃料噴射弁 |
| IT1303808B1 (it) | 1998-12-01 | 2001-02-23 | Ausimont Spa | Trattamenti di superfici con derivati bifunzionali diperfluoropolieteri. |
| JP3601580B2 (ja) | 1999-05-20 | 2004-12-15 | 信越化学工業株式会社 | パーフルオロポリエーテル変性アミノシラン及び表面処理剤並びに該アミノシランの被膜が形成された物品 |
| JP2001207162A (ja) * | 1999-11-04 | 2001-07-31 | Nippon Sheet Glass Co Ltd | 撥水撥油防汚処理液、および撥水撥油防汚処理方法 |
| US6613860B1 (en) | 2000-10-12 | 2003-09-02 | 3M Innovative Properties Company | Compositions comprising fluorinated polyether silanes for rendering substrates oil and water repellent |
| JP2002121286A (ja) * | 2000-10-12 | 2002-04-23 | Asahi Glass Co Ltd | 含フッ素有機ケイ素化合物、それを含む撥水性組成物、ならびに表面処理基材およびその製造方法 |
| JP2002131507A (ja) * | 2000-10-24 | 2002-05-09 | Fuji Photo Film Co Ltd | 防眩性反射防止フィルムおよび偏光板 |
| US6716534B2 (en) * | 2001-11-08 | 2004-04-06 | 3M Innovative Properties Company | Coating composition comprising a fluorochemical polyether silane partial condensate and use thereof |
| US6649272B2 (en) | 2001-11-08 | 2003-11-18 | 3M Innovative Properties Company | Coating composition comprising fluorochemical polyether silane polycondensate and use thereof |
-
2001
- 2001-11-08 US US10/010,144 patent/US6649272B2/en not_active Expired - Fee Related
-
2002
- 2002-08-27 WO PCT/US2002/027331 patent/WO2003040209A1/en not_active Ceased
- 2002-08-27 JP JP2003542252A patent/JP2005508420A/ja active Pending
- 2002-08-27 ES ES02761524T patent/ES2292800T3/es not_active Expired - Lifetime
- 2002-08-27 EP EP02761524A patent/EP1444289B1/en not_active Expired - Lifetime
- 2002-08-27 CN CNB028222067A patent/CN1297586C/zh not_active Expired - Fee Related
- 2002-08-27 AT AT02761524T patent/ATE376021T1/de not_active IP Right Cessation
- 2002-08-27 DE DE60223069T patent/DE60223069T2/de not_active Expired - Lifetime
-
2003
- 2003-11-05 US US10/701,748 patent/US7097910B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| US20040092675A1 (en) | 2004-05-13 |
| DE60223069D1 (de) | 2007-11-29 |
| EP1444289B1 (en) | 2007-10-17 |
| CN1703441A (zh) | 2005-11-30 |
| US7097910B2 (en) | 2006-08-29 |
| WO2003040209A1 (en) | 2003-05-15 |
| ES2292800T3 (es) | 2008-03-16 |
| US20030124361A1 (en) | 2003-07-03 |
| ATE376021T1 (de) | 2007-11-15 |
| US6649272B2 (en) | 2003-11-18 |
| JP2005508420A (ja) | 2005-03-31 |
| EP1444289A1 (en) | 2004-08-11 |
| CN1297586C (zh) | 2007-01-31 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE60223069T2 (de) | Beschichtungzusammensetzungen umfassend polykondensate aus fluorchemischen polyethersilanen und ihre verwendung | |
| DE60216137T2 (de) | Partiell kondensierte fluorochemische polyether-silane enthaltende beschichtungszusammensetzung und deren verwendung | |
| DE60216424T2 (de) | Fluor-Silan-Oligomerzusammensetzung | |
| EP1699841B1 (en) | Coating compositions with perfluoropolyetherisocyanate derived silane and alkoxysilanes | |
| US6613860B1 (en) | Compositions comprising fluorinated polyether silanes for rendering substrates oil and water repellent | |
| JP5580196B2 (ja) | フルオロケミカルウレタン−シラン化合物及びその水性組成物 | |
| DE60127527T2 (de) | Wasserlösliche oder in Wasser dispergierbare fluorochemische Silane, um Substrate öl- und wasserabstossend zu machen | |
| JP5368436B2 (ja) | フルオロケミカルウレタン化合物及びこれに由来する水性組成物 | |
| 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 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8364 | No opposition during term of opposition |