KR100807896B1 - 플루오로알킬 (메트)아크릴레이트 공중합체 코팅 조성물 - Google Patents
플루오로알킬 (메트)아크릴레이트 공중합체 코팅 조성물 Download PDFInfo
- Publication number
- KR100807896B1 KR100807896B1 KR1020037002284A KR20037002284A KR100807896B1 KR 100807896 B1 KR100807896 B1 KR 100807896B1 KR 1020037002284 A KR1020037002284 A KR 1020037002284A KR 20037002284 A KR20037002284 A KR 20037002284A KR 100807896 B1 KR100807896 B1 KR 100807896B1
- Authority
- KR
- South Korea
- Prior art keywords
- group
- meth
- coating composition
- film
- fluoro
- 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 abstract description 29
- 125000003709 fluoroalkyl group Chemical group 0.000 title claims abstract description 25
- 229920001577 copolymer Polymers 0.000 title claims description 66
- 238000000576 coating method Methods 0.000 claims abstract description 39
- 239000011248 coating agent Substances 0.000 claims abstract description 27
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 25
- 239000000314 lubricant Substances 0.000 claims abstract description 20
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims abstract description 17
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims abstract description 15
- 229920002126 Acrylic acid copolymer Polymers 0.000 claims abstract description 12
- 238000013508 migration Methods 0.000 claims abstract description 8
- 239000010408 film Substances 0.000 claims description 35
- 239000002904 solvent Substances 0.000 claims description 23
- 229920000642 polymer Polymers 0.000 claims description 17
- 150000001875 compounds Chemical class 0.000 claims description 16
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 14
- 239000003999 initiator Substances 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 6
- 239000010409 thin film Substances 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000006162 fluoroaliphatic group Chemical group 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000005647 linker group Chemical group 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 150000003254 radicals Chemical class 0.000 claims description 3
- 125000005515 organic divalent group Chemical group 0.000 claims description 2
- 239000000203 mixture Substances 0.000 abstract description 24
- 239000000758 substrate Substances 0.000 abstract description 11
- 230000004888 barrier function Effects 0.000 abstract description 3
- 230000005012 migration Effects 0.000 abstract description 3
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 18
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- 239000000243 solution Substances 0.000 description 17
- 238000000034 method Methods 0.000 description 16
- -1 Fluoro compound Chemical class 0.000 description 14
- DCAYPVUWAIABOU-UHFFFAOYSA-N hexadecane Chemical compound CCCCCCCCCCCCCCCC DCAYPVUWAIABOU-UHFFFAOYSA-N 0.000 description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- 229910052731 fluorine Inorganic materials 0.000 description 12
- 239000011737 fluorine Substances 0.000 description 10
- 238000012360 testing method Methods 0.000 description 10
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 9
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 238000005259 measurement Methods 0.000 description 8
- 125000005460 perfluorocycloalkyl group Chemical group 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 7
- 239000000356 contaminant Substances 0.000 description 7
- 238000006116 polymerization reaction Methods 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 6
- 239000012530 fluid Substances 0.000 description 6
- 239000000178 monomer Substances 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 239000012071 phase Substances 0.000 description 6
- 230000003068 static effect Effects 0.000 description 6
- 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 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- 230000035508 accumulation Effects 0.000 description 5
- 238000009825 accumulation Methods 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 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 5
- 239000007787 solid Substances 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000008367 deionised water Substances 0.000 description 4
- 229910021641 deionized water Inorganic materials 0.000 description 4
- 239000000428 dust Substances 0.000 description 4
- 125000001153 fluoro group Chemical group F* 0.000 description 4
- 239000005457 ice water Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 238000005461 lubrication Methods 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 4
- 230000002441 reversible effect Effects 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000010998 test method Methods 0.000 description 4
- 238000012546 transfer Methods 0.000 description 4
- 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 3
- VIEHKBXCWMMOOU-UHFFFAOYSA-N 2,2,3,3,4,4,4-heptafluorobutyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(F)(F)C(F)(F)C(F)(F)F VIEHKBXCWMMOOU-UHFFFAOYSA-N 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 238000007429 general method Methods 0.000 description 3
- 230000009477 glass transition Effects 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- 239000002609 medium Substances 0.000 description 3
- DCUFMVPCXCSVNP-UHFFFAOYSA-N methacrylic anhydride Chemical compound CC(=C)C(=O)OC(=O)C(C)=C DCUFMVPCXCSVNP-UHFFFAOYSA-N 0.000 description 3
- 229940104873 methyl perfluorobutyl ether Drugs 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 125000006551 perfluoro alkylene group Chemical group 0.000 description 3
- 239000002243 precursor Substances 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 238000003892 spreading Methods 0.000 description 3
- 230000007480 spreading Effects 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 2
- RSVZYSKAPMBSMY-UHFFFAOYSA-N 2,2,3,3-tetrafluoropropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(F)(F)C(F)F RSVZYSKAPMBSMY-UHFFFAOYSA-N 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
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- 230000001680 brushing effect Effects 0.000 description 2
- ABDBNWQRPYOPDF-UHFFFAOYSA-N carbonofluoridic acid Chemical class OC(F)=O ABDBNWQRPYOPDF-UHFFFAOYSA-N 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 239000000919 ceramic Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 238000001723 curing Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 229920002313 fluoropolymer Polymers 0.000 description 2
- 239000004446 fluoropolymer coating Substances 0.000 description 2
- UQSQSQZYBQSBJZ-UHFFFAOYSA-N fluorosulfonic acid Chemical class OS(F)(=O)=O UQSQSQZYBQSBJZ-UHFFFAOYSA-N 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229920003145 methacrylic acid copolymer Polymers 0.000 description 2
- 229940117841 methacrylic acid copolymer Drugs 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 229950000688 phenothiazine Drugs 0.000 description 2
- 239000011253 protective coating Substances 0.000 description 2
- 239000002356 single layer Substances 0.000 description 2
- 239000012085 test solution Substances 0.000 description 2
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 2
- 125000006664 (C1-C3) perfluoroalkyl group Chemical group 0.000 description 1
- PKAHBRRAHOKBPT-UHFFFAOYSA-N 1,1,2,2,3,3,4,4,5,5-decafluoro-6,6-dimethoxycyclohexane Chemical compound COC1(OC)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C1(F)F PKAHBRRAHOKBPT-UHFFFAOYSA-N 0.000 description 1
- HPFWZNWHCWZFBD-UHFFFAOYSA-N 1,1,2,2,3,3,4-heptafluorobutan-1-ol Chemical compound OC(F)(F)C(F)(F)C(F)(F)CF HPFWZNWHCWZFBD-UHFFFAOYSA-N 0.000 description 1
- YYXWJNBPHDUWJP-UHFFFAOYSA-N 2,2,3,3,4,4,4-heptafluorobutanoyl fluoride Chemical compound FC(=O)C(F)(F)C(F)(F)C(F)(F)F YYXWJNBPHDUWJP-UHFFFAOYSA-N 0.000 description 1
- OHMHBGPWCHTMQE-UHFFFAOYSA-N 2,2-dichloro-1,1,1-trifluoroethane Chemical compound FC(F)(F)C(Cl)Cl OHMHBGPWCHTMQE-UHFFFAOYSA-N 0.000 description 1
- QEZGRWSAUJTDEZ-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-3-(piperidine-1-carbonyl)pyrazol-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C=1C(=NN(C=1)CC(=O)N1CC2=C(CC1)NN=N2)C(=O)N1CCCCC1 QEZGRWSAUJTDEZ-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical class OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 230000005526 G1 to G0 transition Effects 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 1
- 239000000020 Nitrocellulose Substances 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 239000006117 anti-reflective coating Substances 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 231100000693 bioaccumulation Toxicity 0.000 description 1
- 238000007664 blowing Methods 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
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 229920003174 cellulose-based polymer Polymers 0.000 description 1
- KYKAJFCTULSVSH-UHFFFAOYSA-N chloro(fluoro)methane Chemical compound F[C]Cl KYKAJFCTULSVSH-UHFFFAOYSA-N 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000002993 cycloalkylene group Chemical group 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 239000002612 dispersion medium Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000005530 etching Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 238000003682 fluorination reaction Methods 0.000 description 1
- 239000004811 fluoropolymer Substances 0.000 description 1
- 230000004907 flux Effects 0.000 description 1
- 239000004519 grease Substances 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000000976 ink Substances 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 238000005304 joining Methods 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 239000010687 lubricating oil Substances 0.000 description 1
- 238000003754 machining Methods 0.000 description 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- 238000001393 microlithography Methods 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 150000004812 organic fluorine compounds Chemical class 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 125000005009 perfluoropropyl group Chemical group FC(C(C(F)(F)F)(F)F)(F)* 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 239000004297 potassium metabisulphite Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 230000007261 regionalization Effects 0.000 description 1
- 230000002940 repellent Effects 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000005476 soldering Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- UZBIRLJMURQVMX-UHFFFAOYSA-J tetrasodium;pyrene-1,3,6,8-tetrasulfonate Chemical compound [Na+].[Na+].[Na+].[Na+].C1=C2C(S(=O)(=O)[O-])=CC(S([O-])(=O)=O)=C(C=C3)C2=C2C3=C(S([O-])(=O)=O)C=C(S([O-])(=O)=O)C2=C1 UZBIRLJMURQVMX-UHFFFAOYSA-J 0.000 description 1
- 238000013519 translation Methods 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- 238000002525 ultrasonication Methods 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 238000003466 welding Methods 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
- C09D133/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
- C09D133/04—Homopolymers or copolymers of esters
- C09D133/14—Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen
- C09D133/16—Homopolymers or copolymers of esters containing halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/62—Halogen-containing esters
- C07C69/63—Halogen-containing esters of saturated acids
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F120/00—Homopolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F120/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F120/10—Esters
- C08F120/22—Esters containing halogen
- C08F120/24—Esters containing halogen containing perhaloalkyl radicals
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/10—Esters
- C08F20/22—Esters containing halogen
- C08F20/24—Esters containing halogen containing perhaloalkyl radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Polymers & Plastics (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Wood Science & Technology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Materials Engineering (AREA)
- Engineering & Computer Science (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Materials Applied To Surfaces To Minimize Adherence Of Mist Or Water (AREA)
- Paints Or Removers (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Application Of Or Painting With Fluid Materials (AREA)
- Adjustment Of The Magnetic Head Position Track Following On Tapes (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Synthetic Leather, Interior Materials Or Flexible Sheet Materials (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US22623500P | 2000-08-18 | 2000-08-18 | |
| US60/226,235 | 2000-08-18 | ||
| PCT/US2001/025527 WO2002016517A2 (en) | 2000-08-18 | 2001-08-15 | Fluoroalkyl (meth)acrylate copolymer coating compositions |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR20030027034A KR20030027034A (ko) | 2003-04-03 |
| KR100807896B1 true KR100807896B1 (ko) | 2008-02-27 |
Family
ID=22848098
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020037002284A Expired - Lifetime KR100807896B1 (ko) | 2000-08-18 | 2001-08-15 | 플루오로알킬 (메트)아크릴레이트 공중합체 코팅 조성물 |
| KR1020037002285A Expired - Lifetime KR100808711B1 (ko) | 2000-08-18 | 2001-08-16 | 분해성, 비결정성 불화화합물 아크릴레이트 중합체 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020037002285A Expired - Lifetime KR100808711B1 (ko) | 2000-08-18 | 2001-08-16 | 분해성, 비결정성 불화화합물 아크릴레이트 중합체 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US6649719B2 (https=) |
| EP (2) | EP1311637B8 (https=) |
| JP (3) | JP5220978B2 (https=) |
| KR (2) | KR100807896B1 (https=) |
| AT (1) | ATE322524T1 (https=) |
| AU (2) | AU2001283381A1 (https=) |
| DE (2) | DE60118576T2 (https=) |
| WO (2) | WO2002016517A2 (https=) |
Families Citing this family (96)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7320829B2 (en) | 1998-03-05 | 2008-01-22 | Omnova Solutions Inc. | Fluorinated polymer and amine resin compositions and products formed therefrom |
| JP3714870B2 (ja) * | 2000-12-28 | 2005-11-09 | セントラル硝子株式会社 | 透明性含フッ素共重合体 |
| US7514263B2 (en) * | 2001-04-02 | 2009-04-07 | 3M Innovative Properties Company | Continuous process for the production of combinatorial libraries of materials |
| DE60201213T2 (de) * | 2001-05-08 | 2005-09-29 | Merck Patent Gmbh | Polymerisierbares Flüssigkristallmaterial |
| CA2447132C (en) | 2001-05-14 | 2008-10-07 | Omnova Solutions Inc. | Polymeric surfactants derived from cyclic monomers having pendant fluorinated carbon groups |
| TWI329105B (en) | 2002-02-01 | 2010-08-21 | Rigel Pharmaceuticals Inc | 2,4-pyrimidinediamine compounds and their uses |
| US7491491B2 (en) * | 2002-03-12 | 2009-02-17 | Polytechnic Institute Of New York University | Detecting and/or measuring a substance based on a resonance shift of photons orbiting within a microsphere |
| US7078454B2 (en) | 2002-04-17 | 2006-07-18 | 3M Innovative Properties Company | Repellent fluorochemical compositions |
| US6930184B2 (en) * | 2002-07-26 | 2005-08-16 | 3M Innovative Properties Company | Functional fluorescent dyes |
| US6894105B2 (en) | 2002-07-26 | 2005-05-17 | 3M Innovatives Properties Company | Dyed fluoropolymers |
| ES2445208T3 (es) | 2002-07-29 | 2014-02-28 | Rigel Pharmaceuticals, Inc. | Compuestos de 2,4-pirimidindiamina para uso en métodos para tratar o prevenir enfermedades autoinmunitarias |
| US6903173B2 (en) * | 2002-08-02 | 2005-06-07 | 3M Innovative Properties Co. | Fluorinated polymers |
| US7157283B2 (en) * | 2002-08-02 | 2007-01-02 | 3M Innovative Properties Company | Continuous process for the production of combinatorial libraries of modified materials |
| US7632916B2 (en) | 2002-08-02 | 2009-12-15 | 3M Innovative Properties Company | Process to modify polymeric materials and resulting compositions |
| US20040043224A1 (en) * | 2002-08-30 | 2004-03-04 | Shmuel Sternberg | Enhanced hydrophobic membranes and methods for making such membranes |
| BRPI0413018B8 (pt) | 2003-07-30 | 2021-05-25 | Rigel Pharmaceuticals Inc | composto, e, uso de um composto |
| US7501074B2 (en) * | 2004-03-04 | 2009-03-10 | Barbara Haviland Minor | Haloketone refrigerant compositions and uses thereof |
| US6992224B2 (en) * | 2004-05-12 | 2006-01-31 | Honeywell International Inc. | Manufacture of fluorinated alcohols |
| US7074343B2 (en) * | 2004-05-26 | 2006-07-11 | E. I. Du Pont De Nemours And Company | 1,1,1,2,2,4,5,5,5-nonafluoro-4-(trifluoromethyl)-3-pentanone refrigerant compositions comprising a hydrocarbon and uses thereof |
| FR2871898B1 (fr) * | 2004-06-18 | 2006-09-08 | Alcatel Sa | Composant a fibre optique et fibre optique associee |
| EP1814878B1 (en) | 2004-11-24 | 2012-01-04 | Rigel Pharmaceuticals, Inc. | Spiro-2, 4-pyrimidinediamine compounds and their uses |
| US7682771B2 (en) | 2004-12-29 | 2010-03-23 | 3M Innovative Properties Company | Compositions containing photosensitive fluorochemical and uses thereof |
| US7495118B2 (en) | 2004-12-30 | 2009-02-24 | 3M Innovative Properties Company | Compositions containing C4-swallow tail silanes |
| US7776983B2 (en) * | 2004-12-30 | 2010-08-17 | 3M Innovative Properties Company | Fluorochemical polymeric surfactants |
| US7160850B2 (en) | 2004-12-30 | 2007-01-09 | 3M Innovative Properties Company | Compositions of monomeric surfactants |
| US7531730B2 (en) * | 2005-02-08 | 2009-05-12 | Phillip Jason Everly | Non-toxic chemical musical instrument string coating and preservative |
| US7576099B2 (en) * | 2005-02-28 | 2009-08-18 | Renovis, Inc. | Amide derivatives as ion-channel ligands and pharmaceutical compositions and methods of using the same |
| WO2007061329A1 (fr) * | 2005-11-25 | 2007-05-31 | Pfc-Tec Llc | Procede pour produire un composant filmogene fluore a faible poids moleculaire et composition sur cette base |
| US7385089B2 (en) * | 2005-12-23 | 2008-06-10 | 3M Innovative Properties Company | Fluorochemical ketone compounds and processes for their use |
| KR100838345B1 (ko) * | 2006-02-17 | 2008-06-13 | 에스케이씨하스디스플레이필름(유) | 표면보호용 코팅 조성물 및 이를 이용한 표면보호필름 |
| US7629298B2 (en) | 2006-02-21 | 2009-12-08 | 3M Innovative Properties Company | Sandstone having a modified wettability and a method for modifying the surface energy of sandstone |
| US8034532B2 (en) * | 2006-04-28 | 2011-10-11 | International Business Machines Corporation | High contact angle topcoat material and use thereof in lithography process |
| US8945808B2 (en) | 2006-04-28 | 2015-02-03 | International Business Machines Corporation | Self-topcoating resist for photolithography |
| US7951524B2 (en) | 2006-04-28 | 2011-05-31 | International Business Machines Corporation | Self-topcoating photoresist for photolithography |
| JP2009203247A (ja) * | 2006-06-16 | 2009-09-10 | Asahi Glass Co Ltd | 含フッ素重合体溶液組成物 |
| US7569715B2 (en) | 2006-07-05 | 2009-08-04 | 3M Innovative Properties Company | Compositions containing silanes |
| WO2008089391A1 (en) | 2007-01-19 | 2008-07-24 | 3M Innovative Properties Company | Fluorinated surfactants and methods of using the same |
| CA2678751C (en) * | 2007-03-26 | 2016-05-17 | Egene, Inc. | Capillary electrophoresis using clear coated capillary tubes |
| CN101679548B (zh) | 2007-06-06 | 2012-07-18 | 3M创新有限公司 | 氟化组合物以及由其制备的表面处理剂 |
| TW200920752A (en) * | 2007-07-11 | 2009-05-16 | Asahi Glass Co Ltd | Method for production of water-repellant/oil-repellant composition, and article |
| US8319095B2 (en) * | 2007-11-27 | 2012-11-27 | Guardian Industries Corp. | Method of making an antireflective silica coating, resulting product, and photovoltaic device comprising same |
| US7923133B2 (en) | 2007-12-21 | 2011-04-12 | 3M Innovative Properties Company | Coatings and methods for particle reduction |
| US8202579B2 (en) | 2008-03-31 | 2012-06-19 | Cooley Group Holdings, Inc. | Water-resistant fabrics and methods of preparation thereof |
| MX2010012161A (es) | 2008-05-05 | 2010-11-30 | 3M Innovative Porperties Company | Metodos para tratar formaciones que producen hidrocarburos que tienen salmuera. |
| BRPI0915952A2 (pt) | 2008-07-18 | 2019-11-26 | 3M Innovative Properties Co | composições de polímero catiônico we método para tratamento de formações contendo hidrocarbonetos com uso das mesmas |
| US9057012B2 (en) | 2008-12-18 | 2015-06-16 | 3M Innovative Properties Company | Method of contacting hydrocarbon-bearing formations with fluorinated phosphate and phosphonate compositions |
| JP5423227B2 (ja) | 2009-08-11 | 2014-02-19 | 富士ゼロックス株式会社 | 画像形成装置及びプログラム |
| JP5413508B2 (ja) * | 2009-09-01 | 2014-02-12 | ダイキン工業株式会社 | 紙用耐水耐油剤、紙処理方法および加工紙 |
| JP5546184B2 (ja) * | 2009-09-08 | 2014-07-09 | 株式会社ネオス | 含フッ素ノニオン系界面活性剤 |
| CN102762618B (zh) * | 2010-02-15 | 2014-10-22 | 大金工业株式会社 | 纸张用防水防油剂以及纸张处理方法 |
| US9290596B2 (en) | 2010-05-27 | 2016-03-22 | The Chemours Company Fc, Llc | Solvent-based fluoropolymer additives and their use in coating compositions |
| US9029452B2 (en) | 2010-05-27 | 2015-05-12 | E I Du Pont De Nemours And Company | Fluoropolymer additive for coatings |
| KR101145439B1 (ko) * | 2010-06-28 | 2012-05-15 | 한국생산기술연구원 | 초발수 표면 및 그 제조방법 |
| WO2012061021A1 (en) | 2010-11-04 | 2012-05-10 | 3M Innovative Properties Company | Fluorinated composition comprising phosphorus containing acid group and alkoxy silane group |
| US9296904B2 (en) | 2010-12-20 | 2016-03-29 | 3M Innovative Properties Company | Coating compositions comprising non-ionic surfactant exhibiting reduced fingerprint visibility |
| US8742022B2 (en) | 2010-12-20 | 2014-06-03 | 3M Innovative Properties Company | Coating compositions comprising non-ionic surfactant exhibiting reduced fingerprint visibility |
| WO2012088216A2 (en) | 2010-12-21 | 2012-06-28 | 3M Innovative Properties Company | Method for treating hydrocarbon-bearing formations with fluorinated amine |
| CN102153902B (zh) * | 2011-03-11 | 2013-05-29 | 安徽嘉智信诺化工有限公司 | 一种涂料油墨用氟碳抗缩孔流平剂 |
| US20120285645A1 (en) * | 2011-03-29 | 2012-11-15 | Daikin Industries, Ltd. | Water- and oil-resistant agent having a decreased content of vinyl pyrrolidone monomer |
| CN103717625B (zh) * | 2011-08-04 | 2016-05-04 | 株式会社Lg化学 | 氟树脂和包含其的光敏树脂组合物 |
| CN104662105B (zh) | 2012-06-19 | 2017-06-13 | 3M创新有限公司 | 包含表现出降低的指纹可见度的可聚合非离子型表面活性剂的涂料组合物 |
| WO2013191861A1 (en) | 2012-06-19 | 2013-12-27 | 3M Innovative Properties Company | Additive comprising low surface energy group and hydroxyl groups and coating compositions |
| WO2014078825A1 (en) | 2012-11-19 | 2014-05-22 | 3M Innovative Properties Company | Composition including a fluorinated polymer and a non-fluorinated polymer and methods of making and using the same |
| US10106724B2 (en) | 2012-11-19 | 2018-10-23 | 3M Innovative Properties Company | Method of contacting hydrocarbon-bearing formations with fluorinated ionic polymers |
| SG11201504914SA (en) | 2012-12-20 | 2015-07-30 | 3M Innovative Properties Co | Copolymers including ultraviolet absorbing groups and fluoropolymer compositions including them |
| CN105073909B (zh) | 2012-12-20 | 2019-05-21 | 3M创新有限公司 | 包含具有紫外线吸收基团的低聚物的含氟聚合物组合物 |
| US9988536B2 (en) * | 2013-11-05 | 2018-06-05 | E I Du Pont De Nemours And Company | Compositions for surface treatments |
| US9777170B2 (en) | 2014-02-25 | 2017-10-03 | The Chemours Company Tt, Llc | Fluorinated polymer additives derived using hydrophilic chain transfer agents for architectural coatings |
| CN104926966A (zh) * | 2014-03-19 | 2015-09-23 | 中国科学院上海有机化学研究所 | 一种低能表面涂层用的含氟聚合物及其制备方法 |
| US10917982B2 (en) | 2014-05-28 | 2021-02-09 | Nitto Denko Corporation | Metal housing and ventilation structure employing same |
| US10836883B2 (en) | 2014-06-18 | 2020-11-17 | 3M Innovative Properties Company | Light transparent fluoropolymer composition and article |
| JP6294513B2 (ja) | 2014-06-25 | 2018-03-14 | スリーエム イノベイティブ プロパティズ カンパニー | 少なくとも１つのオリゴマーを含むフルオロポリマー組成物 |
| US11110689B2 (en) | 2014-06-25 | 2021-09-07 | 3M Innovative Properties Company | Pressure sensitive adhesive composition including ultraviolet light-absorbing oligomer |
| CN104830192A (zh) * | 2015-04-29 | 2015-08-12 | 广德嘉宝莉化工有限公司 | 一种高耐候性高韧性水性涂料 |
| CN107709385B (zh) | 2015-06-25 | 2020-06-12 | 3M创新有限公司 | 包含紫外光吸收基团的共聚物和包含该共聚物的组合物 |
| CN109072113B (zh) * | 2016-01-27 | 2022-01-18 | Nippeco株式会社 | 异物去除润滑组合物、异物去除润滑组合物的涂布构件和异物去除润滑组合物的使用方法 |
| WO2017189388A1 (en) | 2016-04-25 | 2017-11-02 | 3M Innovative Properties Company | Composite particles for curing epoxy resin compositions and curable and cured epoxy resin compositions prepared using the particles |
| CN114671985A (zh) * | 2016-07-08 | 2022-06-28 | 大金工业株式会社 | 固化性组合物、其制造方法以及使用该固化性组合物的物品 |
| JP6753280B2 (ja) | 2016-11-24 | 2020-09-09 | コニカミノルタ株式会社 | 電子写真感光体 |
| EP3336112A1 (en) * | 2016-12-19 | 2018-06-20 | 3M Innovative Properties Company | Fluoroalkyl (meth)acrylate polymers and compositions |
| US20200017623A1 (en) | 2017-03-08 | 2020-01-16 | 3M Innovative Properties Company | Blue led cure on demand compositions |
| WO2019022185A1 (ja) * | 2017-07-27 | 2019-01-31 | 日産化学株式会社 | 剥離層形成用組成物及び剥離層 |
| WO2019028271A1 (en) * | 2017-08-02 | 2019-02-07 | Massachusetts Institute Of Technology | SUSTAINABLE, WATER RESISTANT COATINGS |
| JP2019061003A (ja) * | 2017-09-26 | 2019-04-18 | コニカミノルタ株式会社 | 電子写真感光体及び画像形成装置 |
| WO2019067394A1 (en) * | 2017-09-27 | 2019-04-04 | Arkema Inc. | HALOGENATED ORGANIC HETEROALKENYL AND HETEROALKYL COMPOUNDS AND METHODS OF PREPARATION THEREOF |
| JP7157307B2 (ja) * | 2018-05-11 | 2022-10-20 | ダイキン工業株式会社 | 撥水撥油剤および繊維製品 |
| US12476052B2 (en) * | 2018-06-21 | 2025-11-18 | KYOCERA AVX Components Corporation | Delamination-resistant solid electrolytic capacitor |
| WO2020016708A2 (en) | 2018-07-18 | 2020-01-23 | 3M Innovative Properties Company | Vehicle sensors comprising repellent surface, protective films, repellent coating compositions, and methods |
| WO2020100113A1 (en) | 2018-11-16 | 2020-05-22 | 3M Innovative Properties Company | Composition including solvent and fluorinated polymer and method of treating a hydrocarbon-bearing formation |
| KR102852297B1 (ko) | 2019-03-22 | 2025-09-01 | 헨켈 아게 운트 코. 카게아아 | 전자 부품 방수를 위한 코팅물 |
| BE1027888B1 (nl) * | 2019-12-19 | 2021-07-27 | Unilin Bv | Gebruik van een coating materiaal op de randen van decoratieve panelen en werkwijze |
| EP4200064A1 (en) * | 2020-08-18 | 2023-06-28 | Donaldson Company, Inc. | Article including filtration media and fluoropolymer and methods of making and using same |
| US11837415B2 (en) | 2021-01-15 | 2023-12-05 | KYOCERA AVX Components Corpration | Solid electrolytic capacitor |
| EP4288466A1 (en) | 2021-02-03 | 2023-12-13 | Donaldson Company, Inc. | Compositions and articles including perfluoropolyether bottlebrush polymers and methods of making and using same |
| KR102571576B1 (ko) * | 2021-05-17 | 2023-08-28 | 이근수 | 불소계 공중합체, 제조 방법, 이를 포함하는 반사방지막 및 응용 |
| CN119954619A (zh) * | 2023-11-07 | 2025-05-09 | 三明市海斯福化工有限责任公司 | 一种氢氟醚化合物及其应用和制备方法 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2592055A1 (fr) * | 1985-12-24 | 1987-06-26 | Charbonnages Ste Chimique | Vernis de protection |
| EP0889092A1 (en) * | 1996-03-22 | 1999-01-07 | Nippon Zeon Co., Ltd. | Lubricative polymer containing liquid and method of forming film of lubricative polymer |
Family Cites Families (39)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2666797A (en) | 1950-05-26 | 1954-01-19 | Minnesota Mining & Mfg | Fluorinated alcohols and acetate esters |
| US2841573A (en) | 1955-12-29 | 1958-07-01 | Minnesota Mining & Mfg | Fluorocarbon vinyl-type esters and polymers |
| US2803615A (en) | 1956-01-23 | 1957-08-20 | Minnesota Mining & Mfg | Fluorocarbon acrylate and methacrylate esters and polymers |
| US3398182A (en) | 1962-06-22 | 1968-08-20 | Minnesota Mining & Mfg | Fluorocarbon urethane compounds |
| US3177185A (en) | 1963-10-28 | 1965-04-06 | Allied Chem | Sym-hexafluoroisopropyl acrylate compounds and polymers thereof |
| US3341497A (en) | 1966-01-21 | 1967-09-12 | Minnesota Mining & Mfg | Organic solvent soluble perfluorocarbon copolymers |
| US3462296A (en) | 1966-07-22 | 1969-08-19 | Du Pont | Fluorinated oil- and water-repellent copolymer and process for treating fibrous materials with said copolymer |
| DE1595696A1 (de) * | 1966-11-29 | 1970-04-23 | Hoechst Ag | Polymere Acrylsaeure-perfluor-2,3-dimethyl-buthylester als oel- und wasserabweisende UEberzuege |
| US3811933A (en) * | 1969-12-15 | 1974-05-21 | Air Prod & Chem | Oil and grease resistant paper products and process for treating cellulosic materials |
| US3792128A (en) * | 1969-12-15 | 1974-02-12 | Air Prod & Chem | Fluoropolymer-carboxylated styrene-butadiene functional surface coating compositions |
| US3770685A (en) * | 1972-01-24 | 1973-11-06 | Air Prod & Chem | Functional surface coating compositions for cellulosic material |
| CH320273A4 (https=) | 1972-03-06 | 1976-09-15 | ||
| ZA738419B (en) | 1972-11-06 | 1974-09-25 | Christiaens Sa A | New derivatives of 2-aminoindane,the preparation and use thereof |
| US4001305A (en) | 1974-02-04 | 1977-01-04 | Ciba-Geigy Corporation | Rf-glycols containing two perfluoroalkylthio groups and useful compositions therefrom |
| US4029585A (en) | 1975-07-26 | 1977-06-14 | E. I. Du Pont De Nemours And Company | Aqueous dispersions of perfluoroalkyl esters for treating textiles |
| US4264484A (en) | 1979-01-24 | 1981-04-28 | Minnesota Mining And Manufacturing Company | Carpet treatment |
| JP2578735B2 (ja) * | 1985-12-24 | 1997-02-05 | ソシエテ シミツク デ シヤルボナ−ジユ エス．ア− | 保護ワニス |
| JP2502059B2 (ja) | 1986-02-05 | 1996-05-29 | 旭硝子株式会社 | 汚れ除去性の高い撥水撥油剤 |
| EP0250996A3 (en) * | 1986-06-21 | 1988-06-01 | Daikin Industries, Limited | Optical fibers |
| JPH01106001A (ja) * | 1987-10-20 | 1989-04-24 | Mitsubishi Rayon Co Ltd | 光フアイバー鞘材用樹脂組成物 |
| US4849291A (en) | 1987-12-02 | 1989-07-18 | Eastman Kodak Company | Magnetic recording element |
| JPH02298384A (ja) * | 1989-05-12 | 1990-12-10 | Mitsubishi Rayon Co Ltd | 塗膜の形成方法 |
| JPH0312269A (ja) * | 1989-06-12 | 1991-01-21 | Mitsubishi Rayon Co Ltd | 塗膜の形成方法 |
| US5410073A (en) | 1989-12-29 | 1995-04-25 | E. I. Du Pont De Nemours And Company | Manufacture of polyfluoro nitrogen containing organic compounds |
| JPH0425569A (ja) * | 1990-05-22 | 1992-01-29 | Mitsubishi Rayon Co Ltd | 紙艶出し加工用塗料組成物 |
| US5223593A (en) | 1991-08-08 | 1993-06-29 | Minnesota Mining And Manufacturing Company | Fluorine containing plastic optical fiber cores |
| US5274159A (en) | 1993-02-18 | 1993-12-28 | Minnesota Mining And Manufacturing Company | Destructable fluorinated alkoxysilane surfactants and repellent coatings derived therefrom |
| US5488142A (en) | 1993-10-04 | 1996-01-30 | Minnesota Mining And Manufacturing Company | Fluorination in tubular reactor system |
| US6037429A (en) | 1995-06-16 | 2000-03-14 | 3M Innovative Properties Company | Water-soluble fluorochemical polymers for use in water and oil repellent masonry treatments |
| US5641844A (en) | 1995-12-13 | 1997-06-24 | W. L. Gore & Associates, Inc. | Polymers with crystallizable fluoropolymers |
| US5688884A (en) | 1995-08-31 | 1997-11-18 | E. I. Du Pont De Nemours And Company | Polymerization process |
| US5772817A (en) | 1997-02-10 | 1998-06-30 | Micro Lithography, Inc. | Optical pellicle mounting system |
| US6005137A (en) | 1997-06-10 | 1999-12-21 | 3M Innovative Properties Company | Halogenated acrylates and polymers derived therefrom |
| JPH1143641A (ja) * | 1997-07-29 | 1999-02-16 | Nagoya Gosei Kk | 切り刃用フッ素樹脂コーティング剤 |
| US6197426B1 (en) * | 1998-01-12 | 2001-03-06 | 3M Innovative Properties Company | Fluorochemical copolymer and fluorochemical copolymer compositions useful for imparting repellency properties to a substrate |
| JP4035892B2 (ja) * | 1998-06-05 | 2008-01-23 | 旭硝子株式会社 | コーティング用組成物 |
| US6238798B1 (en) | 1999-02-22 | 2001-05-29 | 3M Innovative Properties Company | Ceramer composition and composite comprising free radically curable fluorochemical component |
| ES2230125T5 (es) | 1999-07-20 | 2016-10-04 | 3M Innovative Properties Company | Uso de cetonas fluoradas en composiciones extintoras de incendios |
| EP1246856B1 (en) | 1999-10-27 | 2009-07-15 | 3M Innovative Properties Company | Fluorochemical sulfonamide surfactants |
-
2001
- 2001-08-15 AU AU2001283381A patent/AU2001283381A1/en not_active Abandoned
- 2001-08-15 AT AT01962184T patent/ATE322524T1/de not_active IP Right Cessation
- 2001-08-15 EP EP01962184A patent/EP1311637B8/en not_active Expired - Lifetime
- 2001-08-15 KR KR1020037002284A patent/KR100807896B1/ko not_active Expired - Lifetime
- 2001-08-15 WO PCT/US2001/025527 patent/WO2002016517A2/en not_active Ceased
- 2001-08-15 JP JP2002521601A patent/JP5220978B2/ja not_active Expired - Lifetime
- 2001-08-15 DE DE60118576T patent/DE60118576T2/de not_active Expired - Lifetime
- 2001-08-16 US US09/931,215 patent/US6649719B2/en not_active Expired - Lifetime
- 2001-08-16 EP EP01962202A patent/EP1326902B1/en not_active Expired - Lifetime
- 2001-08-16 JP JP2002521182A patent/JP2004506784A/ja active Pending
- 2001-08-16 KR KR1020037002285A patent/KR100808711B1/ko not_active Expired - Lifetime
- 2001-08-16 AU AU2001283399A patent/AU2001283399A1/en not_active Abandoned
- 2001-08-16 WO PCT/US2001/025626 patent/WO2002016306A2/en not_active Ceased
- 2001-08-16 DE DE60131671T patent/DE60131671T2/de not_active Expired - Lifetime
-
2012
- 2012-08-17 JP JP2012180827A patent/JP2013028807A/ja active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2592055A1 (fr) * | 1985-12-24 | 1987-06-26 | Charbonnages Ste Chimique | Vernis de protection |
| EP0889092A1 (en) * | 1996-03-22 | 1999-01-07 | Nippon Zeon Co., Ltd. | Lubricative polymer containing liquid and method of forming film of lubricative polymer |
Also Published As
| Publication number | Publication date |
|---|---|
| ATE322524T1 (de) | 2006-04-15 |
| KR100808711B1 (ko) | 2008-02-29 |
| WO2002016306A2 (en) | 2002-02-28 |
| EP1311637B8 (en) | 2006-06-28 |
| KR20030027034A (ko) | 2003-04-03 |
| JP5220978B2 (ja) | 2013-06-26 |
| DE60131671D1 (en) | 2008-01-10 |
| JP2013028807A (ja) | 2013-02-07 |
| KR20030031981A (ko) | 2003-04-23 |
| DE60118576T2 (de) | 2006-11-02 |
| EP1311637B1 (en) | 2006-04-05 |
| DE60131671T2 (de) | 2008-10-30 |
| US6649719B2 (en) | 2003-11-18 |
| EP1326902A2 (en) | 2003-07-16 |
| WO2002016306A3 (en) | 2003-03-20 |
| JP2004506784A (ja) | 2004-03-04 |
| EP1326902B1 (en) | 2007-11-28 |
| WO2002016517A3 (en) | 2002-05-23 |
| AU2001283399A1 (en) | 2002-03-04 |
| JP2004506810A (ja) | 2004-03-04 |
| EP1311637A2 (en) | 2003-05-21 |
| AU2001283381A1 (en) | 2002-03-04 |
| DE60118576D1 (de) | 2006-05-18 |
| US20020042470A1 (en) | 2002-04-11 |
| WO2002016517A2 (en) | 2002-02-28 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR100807896B1 (ko) | 플루오로알킬 (메트)아크릴레이트 공중합체 코팅 조성물 | |
| US6291704B1 (en) | Polymerizable halogenated vinyl ethers | |
| KR102743634B1 (ko) | 막 및 이것으로 표면이 피복된 기재 | |
| KR20140139604A (ko) | 내구형 방수·방습성 코팅 조성물 | |
| JP2023100621A (ja) | 光架橋性フルオロポリマーコーティング組成物及びそれから形成されるコーティング層 | |
| WO2011001846A1 (ja) | 表面処理剤、物品および含フッ素エーテル化合物 | |
| WO2002040603A2 (en) | Water-repellent, oil-repellent and soil resistant coating composition | |
| US20060149012A1 (en) | Fluorochemical polymeric surfactants | |
| WO2002004534A2 (en) | Coating composition for optical device parts or electrical device parts, and coating method | |
| EP2009499A1 (en) | Material of the resist-protecting membrane for immersion lithography | |
| JP5362246B2 (ja) | 潤滑オイルのバリア剤組成物、それを製造する方法およびその用途 | |
| US20040028914A1 (en) | Water-repellent, oil-repellent and soil resistant coating composition | |
| JP5309622B2 (ja) | 表面処理剤 | |
| JP5040499B2 (ja) | 撥油性共重合体およびその製造方法ならびに撥油性処理液 | |
| JP5145262B2 (ja) | 電子部品用樹脂付着防止剤、それを含む電子部材および電子部品 | |
| JP5171452B2 (ja) | 電子部品用樹脂付着防止組成物 | |
| KR20230037593A (ko) | 가교결합성 플루오로중합체 및 이로부터 형성된 코팅 | |
| JP5124441B2 (ja) | 半田用フラックス這い上がり防止組成物 | |
| JP6670615B2 (ja) | 防水・防湿コーティング剤 | |
| JP4661140B2 (ja) | 撥水撥油剤用溶液組成物、基材およびその製造方法 | |
| TW202110910A (zh) | 含氟密封材形成用組成物 | |
| JPH04247337A (ja) | 光ディスク | |
| JP5491417B2 (ja) | 電子部品用樹脂付着防止剤、それを含む電子部材および電子部品 | |
| JP2007056134A (ja) | レジスト保護膜 | |
| JP2010085637A (ja) | 液浸露光用レジスト保護膜組成物およびレジストパターンの形成方法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PA0105 | International application |
Patent event date: 20030217 Patent event code: PA01051R01D Comment text: International Patent Application |
|
| PG1501 | Laying open of application | ||
| A201 | Request for examination | ||
| PA0201 | Request for examination |
Patent event code: PA02012R01D Patent event date: 20060816 Comment text: Request for Examination of Application |
|
| E902 | Notification of reason for refusal | ||
| PE0902 | Notice of grounds for rejection |
Comment text: Notification of reason for refusal Patent event date: 20070921 Patent event code: PE09021S01D |
|
| E701 | Decision to grant or registration of patent right | ||
| PE0701 | Decision of registration |
Patent event code: PE07011S01D Comment text: Decision to Grant Registration Patent event date: 20071127 |
|
| GRNT | Written decision to grant | ||
| PR0701 | Registration of establishment |
Comment text: Registration of Establishment Patent event date: 20080220 Patent event code: PR07011E01D |
|
| PR1002 | Payment of registration fee |
Payment date: 20080220 End annual number: 3 Start annual number: 1 |
|
| PG1601 | Publication of registration | ||
| PR1001 | Payment of annual fee |
Payment date: 20110208 Start annual number: 4 End annual number: 4 |
|
| PR1001 | Payment of annual fee |
Payment date: 20120207 Start annual number: 5 End annual number: 5 |
|
| FPAY | Annual fee payment |
Payment date: 20130201 Year of fee payment: 6 |
|
| PR1001 | Payment of annual fee |
Payment date: 20130201 Start annual number: 6 End annual number: 6 |
|
| FPAY | Annual fee payment |
Payment date: 20140204 Year of fee payment: 7 |
|
| PR1001 | Payment of annual fee |
Payment date: 20140204 Start annual number: 7 End annual number: 7 |
|
| FPAY | Annual fee payment |
Payment date: 20150119 Year of fee payment: 8 |
|
| PR1001 | Payment of annual fee |
Payment date: 20150119 Start annual number: 8 End annual number: 8 |
|
| FPAY | Annual fee payment |
Payment date: 20160119 Year of fee payment: 9 |
|
| PR1001 | Payment of annual fee |
Payment date: 20160119 Start annual number: 9 End annual number: 9 |
|
| FPAY | Annual fee payment |
Payment date: 20170119 Year of fee payment: 10 |
|
| PR1001 | Payment of annual fee |
Payment date: 20170119 Start annual number: 10 End annual number: 10 |
|
| FPAY | Annual fee payment |
Payment date: 20180118 Year of fee payment: 11 |
|
| PR1001 | Payment of annual fee |
Payment date: 20180118 Start annual number: 11 End annual number: 11 |
|
| FPAY | Annual fee payment |
Payment date: 20190116 Year of fee payment: 12 |
|
| PR1001 | Payment of annual fee |
Payment date: 20190116 Start annual number: 12 End annual number: 12 |
|
| FPAY | Annual fee payment |
Payment date: 20200115 Year of fee payment: 13 |
|
| PR1001 | Payment of annual fee |
Payment date: 20200115 Start annual number: 13 End annual number: 13 |
|
| PR1001 | Payment of annual fee |
Payment date: 20210115 Start annual number: 14 End annual number: 14 |
|
| PC1801 | Expiration of term |
Termination date: 20220215 Termination category: Expiration of duration |