JP5536663B2 - フルオロポリマーエマルション - Google Patents
フルオロポリマーエマルション Download PDFInfo
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- JP5536663B2 JP5536663B2 JP2010537022A JP2010537022A JP5536663B2 JP 5536663 B2 JP5536663 B2 JP 5536663B2 JP 2010537022 A JP2010537022 A JP 2010537022A JP 2010537022 A JP2010537022 A JP 2010537022A JP 5536663 B2 JP5536663 B2 JP 5536663B2
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- Japan
- Prior art keywords
- group
- alkyl
- mixture
- acrylate
- integer
- Prior art date
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- 229920002313 fluoropolymer Polymers 0.000 title claims abstract description 20
- 239000004811 fluoropolymer Substances 0.000 title claims abstract description 13
- 239000000839 emulsion Substances 0.000 title description 27
- 239000000203 mixture Substances 0.000 claims abstract description 185
- 239000000178 monomer Substances 0.000 claims abstract description 68
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims abstract description 52
- 239000002105 nanoparticle Substances 0.000 claims abstract description 48
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 35
- 125000003709 fluoroalkyl group Chemical group 0.000 claims abstract description 9
- 125000006165 cyclic alkyl group Chemical group 0.000 claims abstract description 6
- -1 phenylene, ethylene Chemical class 0.000 claims description 51
- 229910052739 hydrogen Inorganic materials 0.000 claims description 44
- 239000002245 particle Substances 0.000 claims description 43
- 239000000758 substrate Substances 0.000 claims description 36
- 125000004432 carbon atom Chemical group C* 0.000 claims description 34
- 239000004744 fabric Substances 0.000 claims description 28
- 229910052731 fluorine Inorganic materials 0.000 claims description 27
- 239000001257 hydrogen Substances 0.000 claims description 27
- 239000000835 fiber Substances 0.000 claims description 23
- 238000000034 method Methods 0.000 claims description 21
- 229910052799 carbon Inorganic materials 0.000 claims description 19
- 150000002431 hydrogen Chemical group 0.000 claims description 17
- 239000005977 Ethylene Substances 0.000 claims description 16
- 229910052801 chlorine Inorganic materials 0.000 claims description 16
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 claims description 15
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 15
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 14
- 229910052809 inorganic oxide Inorganic materials 0.000 claims description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 125000005647 linker group Chemical group 0.000 claims description 10
- 239000000463 material Substances 0.000 claims description 10
- 125000005842 heteroatom Chemical group 0.000 claims description 8
- 239000004753 textile Substances 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 6
- 150000003926 acrylamides Chemical class 0.000 claims description 5
- 229910052782 aluminium Inorganic materials 0.000 claims description 5
- 125000004429 atom Chemical group 0.000 claims description 5
- 229910052748 manganese Inorganic materials 0.000 claims description 5
- 229910052710 silicon Inorganic materials 0.000 claims description 5
- 229910052719 titanium Inorganic materials 0.000 claims description 5
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 5
- 229910052725 zinc Inorganic materials 0.000 claims description 5
- 125000003903 2-propenyl group Chemical class [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 4
- 150000001768 cations Chemical class 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- 239000010985 leather Substances 0.000 claims description 4
- 238000006116 polymerization reaction Methods 0.000 claims description 4
- 125000000391 vinyl group Chemical class [H]C([*])=C([H])[H] 0.000 claims description 4
- 229910052726 zirconium Inorganic materials 0.000 claims description 4
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 3
- 229910008423 Si—B Inorganic materials 0.000 claims description 3
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims description 3
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- 125000000743 hydrocarbylene group Chemical group 0.000 claims description 3
- 125000000962 organic group Chemical group 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 3
- 150000003440 styrenes Chemical class 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 229930195735 unsaturated hydrocarbon Natural products 0.000 claims description 3
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 claims description 2
- 150000001993 dienes Chemical class 0.000 claims description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 2
- 229920002554 vinyl polymer Chemical class 0.000 claims description 2
- 239000011248 coating agent Substances 0.000 claims 1
- 238000000576 coating method Methods 0.000 claims 1
- 238000003672 processing method Methods 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 115
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 104
- 239000008367 deionised water Substances 0.000 description 63
- 229910021641 deionized water Inorganic materials 0.000 description 63
- 229910052757 nitrogen Inorganic materials 0.000 description 52
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 49
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 48
- 239000011541 reaction mixture Substances 0.000 description 45
- 239000000243 solution Substances 0.000 description 36
- 235000019441 ethanol Nutrition 0.000 description 29
- 239000004908 Emulsion polymer Substances 0.000 description 26
- 230000000052 comparative effect Effects 0.000 description 26
- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
- 239000000460 chlorine Substances 0.000 description 19
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 17
- 239000007787 solid Substances 0.000 description 17
- 238000010998 test method Methods 0.000 description 16
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 15
- 239000004743 Polypropylene Substances 0.000 description 14
- 229920001155 polypropylene Polymers 0.000 description 14
- JTHZUSWLNCPZLX-UHFFFAOYSA-N 6-fluoro-3-methyl-2h-indazole Chemical compound FC1=CC=C2C(C)=NNC2=C1 JTHZUSWLNCPZLX-UHFFFAOYSA-N 0.000 description 13
- 230000015572 biosynthetic process Effects 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 13
- 239000004745 nonwoven fabric Substances 0.000 description 13
- 229920000642 polymer Polymers 0.000 description 13
- NLMKTBGFQGKQEV-UHFFFAOYSA-N 2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-(2-hexadecoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethanol Chemical compound CCCCCCCCCCCCCCCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCO NLMKTBGFQGKQEV-UHFFFAOYSA-N 0.000 description 12
- WDQMWEYDKDCEHT-UHFFFAOYSA-N 2-ethylhexyl 2-methylprop-2-enoate Chemical compound CCCCC(CC)COC(=O)C(C)=C WDQMWEYDKDCEHT-UHFFFAOYSA-N 0.000 description 12
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 12
- 239000002202 Polyethylene glycol Substances 0.000 description 12
- 239000003795 chemical substances by application Substances 0.000 description 12
- 230000005484 gravity Effects 0.000 description 12
- 229940051250 hexylene glycol Drugs 0.000 description 12
- 238000002347 injection Methods 0.000 description 12
- 239000007924 injection Substances 0.000 description 12
- 239000008267 milk Substances 0.000 description 12
- 210000004080 milk Anatomy 0.000 description 12
- 235000013336 milk Nutrition 0.000 description 12
- 229920001223 polyethylene glycol Polymers 0.000 description 12
- 150000001298 alcohols Chemical class 0.000 description 11
- 239000003921 oil Substances 0.000 description 11
- ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 10
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 10
- 229920000728 polyester Polymers 0.000 description 10
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 9
- GBBZLMLLFVFKJM-UHFFFAOYSA-N 1,2-diiodoethane Chemical compound ICCI GBBZLMLLFVFKJM-UHFFFAOYSA-N 0.000 description 8
- 239000002585 base Substances 0.000 description 8
- 238000004817 gas chromatography Methods 0.000 description 8
- 230000002706 hydrostatic effect Effects 0.000 description 8
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical class O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 229920001577 copolymer Polymers 0.000 description 7
- 238000002156 mixing Methods 0.000 description 7
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 6
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 5
- 229910052783 alkali metal Inorganic materials 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 238000007598 dipping method Methods 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- 239000011737 fluorine Substances 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 230000002940 repellent Effects 0.000 description 5
- 239000005871 repellent Substances 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- 238000011282 treatment Methods 0.000 description 5
- BQCIDUSAKPWEOX-UHFFFAOYSA-N 1,1-Difluoroethene Chemical compound FC(F)=C BQCIDUSAKPWEOX-UHFFFAOYSA-N 0.000 description 4
- BZPCMSSQHRAJCC-UHFFFAOYSA-N 1,2,3,3,4,4,5,5,5-nonafluoro-1-(1,2,3,3,4,4,5,5,5-nonafluoropent-1-enoxy)pent-1-ene Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)=C(F)OC(F)=C(F)C(F)(F)C(F)(F)C(F)(F)F BZPCMSSQHRAJCC-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 229920000840 ethylene tetrafluoroethylene copolymer Polymers 0.000 description 4
- 229910021485 fumed silica Inorganic materials 0.000 description 4
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 4
- 229910052751 metal Chemical class 0.000 description 4
- 239000002184 metal Chemical class 0.000 description 4
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 4
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 4
- 238000012545 processing Methods 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- PPXVPFPTMXFUDE-UHFFFAOYSA-N 1,1,1,2,2-pentafluoro-4-iodobutane Chemical compound FC(F)(F)C(F)(F)CCI PPXVPFPTMXFUDE-UHFFFAOYSA-N 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 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 3
- CDXFIRXEAJABAZ-UHFFFAOYSA-N 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F CDXFIRXEAJABAZ-UHFFFAOYSA-N 0.000 description 3
- 0 C*CCC(C)CC1CC=C2C(CC3(*C4)C4C3CCCC3CC3)(*C)C2C1 Chemical compound C*CCC(C)CC1CC=C2C(CC3(*C4)C4C3CCCC3CC3)(*C)C2C1 0.000 description 3
- 229920000742 Cotton Polymers 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 150000002009 diols Chemical class 0.000 description 3
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 239000000123 paper Substances 0.000 description 3
- 230000001846 repelling effect Effects 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 229920002994 synthetic fiber Polymers 0.000 description 3
- 239000012209 synthetic fiber Substances 0.000 description 3
- XMGQYMWWDOXHJM-JTQLQIEISA-N (+)-α-limonene Chemical compound CC(=C)[C@@H]1CCC(C)=CC1 XMGQYMWWDOXHJM-JTQLQIEISA-N 0.000 description 2
- YXBZHGLURYLFOB-UHFFFAOYSA-N 1,1,1,2,2,3,3,4,4,6,6,8,8-tridecafluoro-10-iododecane Chemical compound [H]C([H])(I)C([H])([H])C(F)(F)C([H])([H])C(F)(F)C([H])([H])C(F)(F)C(F)(F)C(F)(F)C(F)(F)F YXBZHGLURYLFOB-UHFFFAOYSA-N 0.000 description 2
- MAGFQRLKWCCTQJ-UHFFFAOYSA-N 4-ethenylbenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=C(C=C)C=C1 MAGFQRLKWCCTQJ-UHFFFAOYSA-N 0.000 description 2
- 239000004342 Benzoyl peroxide Substances 0.000 description 2
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- YIVJZNGAASQVEM-UHFFFAOYSA-N Lauroyl peroxide Chemical compound CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCC YIVJZNGAASQVEM-UHFFFAOYSA-N 0.000 description 2
- 239000004677 Nylon Substances 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 150000001339 alkali metal compounds Chemical class 0.000 description 2
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 2
- 150000008046 alkali metal hydrides Chemical class 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 235000019400 benzoyl peroxide Nutrition 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000007334 copolymerization reaction Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 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 2
- ZQMIGQNCOMNODD-UHFFFAOYSA-N diacetyl peroxide Chemical compound CC(=O)OOC(C)=O ZQMIGQNCOMNODD-UHFFFAOYSA-N 0.000 description 2
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- AQYSYJUIMQTRMV-UHFFFAOYSA-N hypofluorous acid Chemical compound FO AQYSYJUIMQTRMV-UHFFFAOYSA-N 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 238000011005 laboratory method Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 229920001778 nylon Polymers 0.000 description 2
- 150000002978 peroxides Chemical group 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical class [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- 239000010452 phosphate Chemical class 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000012085 test solution Substances 0.000 description 2
- 150000003573 thiols Chemical class 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 238000009736 wetting Methods 0.000 description 2
- CWERFXDMOOJRLD-UHFFFAOYSA-N 1-(2-prop-2-enoyloxypropyl)cyclohexane-1,2-dicarboxylic acid Chemical compound C=CC(=O)OC(C)CC1(C(O)=O)CCCCC1C(O)=O CWERFXDMOOJRLD-UHFFFAOYSA-N 0.000 description 1
- YUTHQCGFZNYPIG-UHFFFAOYSA-N 1-[2-(2-methylprop-2-enoyloxy)ethyl]cyclohexane-1,2-dicarboxylic acid Chemical compound CC(=C)C(=O)OCCC1(C(O)=O)CCCCC1C(O)=O YUTHQCGFZNYPIG-UHFFFAOYSA-N 0.000 description 1
- NKIIKKAXXDXYJS-UHFFFAOYSA-N 1-prop-2-enoyloxypropane-2-sulfonic acid Chemical compound OS(=O)(=O)C(C)COC(=O)C=C NKIIKKAXXDXYJS-UHFFFAOYSA-N 0.000 description 1
- QZFZPVVDBGXQTB-UHFFFAOYSA-N 2,2,3,3,4,4,5,5,6,6,6-undecafluorohexan-1-ol Chemical compound OCC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F QZFZPVVDBGXQTB-UHFFFAOYSA-N 0.000 description 1
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- AKQHUJRZKBYZLC-UHFFFAOYSA-N tri(propan-2-yl)-prop-2-enylsilane Chemical compound CC(C)[Si](C(C)C)(C(C)C)CC=C AKQHUJRZKBYZLC-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- 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
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- 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
- C08F220/00—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
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/22—Esters containing halogen
- C08F220/24—Esters containing halogen containing perhaloalkyl radicals
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- 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
- C08F14/00—Homopolymers and 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 a halogen
- C08F14/18—Monomers containing fluorine
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- 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
- C08F2/00—Processes of polymerisation
- C08F2/44—Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
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- 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
- C08F22/00—Homopolymers and 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 a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides or nitriles thereof
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
- C08K3/20—Oxides; Hydroxides
- C08K3/22—Oxides; Hydroxides of metals
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L27/00—Compositions of 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 a halogen; Compositions of derivatives of such polymers
- C08L27/02—Compositions of 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 a halogen; Compositions of derivatives of such polymers not modified by chemical after-treatment
- C08L27/12—Compositions of 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 a halogen; Compositions of derivatives of such polymers not modified by chemical after-treatment containing fluorine atoms
-
- 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
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- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
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- 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
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- 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]
- Y10T428/3154—Of fluorinated addition polymer from unsaturated monomers
-
- 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]
- Y10T428/31971—Of carbohydrate
- Y10T428/31993—Of paper
-
- 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
- Y10T442/00—Fabric [woven, knitted, or nonwoven textile or cloth, etc.]
- Y10T442/20—Coated or impregnated woven, knit, or nonwoven fabric which is not [a] associated with another preformed layer or fiber layer or, [b] with respect to woven and knit, characterized, respectively, by a particular or differential weave or knit, wherein the coating or impregnation is neither a foamed material nor a free metal or alloy layer
-
- 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
- Y10T442/00—Fabric [woven, knitted, or nonwoven textile or cloth, etc.]
- Y10T442/20—Coated or impregnated woven, knit, or nonwoven fabric which is not [a] associated with another preformed layer or fiber layer or, [b] with respect to woven and knit, characterized, respectively, by a particular or differential weave or knit, wherein the coating or impregnation is neither a foamed material nor a free metal or alloy layer
- Y10T442/2164—Coating or impregnation specified as water repellent
- Y10T442/2172—Also specified as oil repellent
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US574407P | 2007-12-07 | 2007-12-07 | |
| US61/005,744 | 2007-12-07 | ||
| US12/268,470 US8314037B2 (en) | 2007-12-07 | 2008-11-11 | Fluoropolymer emulsions |
| US12/268,470 | 2008-11-11 | ||
| PCT/US2008/085298 WO2009076109A1 (en) | 2007-12-07 | 2008-12-03 | Fluoropolymer emulsions |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2011506640A JP2011506640A (ja) | 2011-03-03 |
| JP2011506640A5 JP2011506640A5 (enExample) | 2012-01-26 |
| JP5536663B2 true JP5536663B2 (ja) | 2014-07-02 |
Family
ID=40721959
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010537022A Expired - Fee Related JP5536663B2 (ja) | 2007-12-07 | 2008-12-03 | フルオロポリマーエマルション |
Country Status (11)
| Country | Link |
|---|---|
| US (2) | US20090148653A1 (enExample) |
| EP (1) | EP2217630B1 (enExample) |
| JP (1) | JP5536663B2 (enExample) |
| KR (1) | KR101589319B1 (enExample) |
| CN (1) | CN101889035B (enExample) |
| AT (1) | ATE547444T1 (enExample) |
| AU (1) | AU2008335494B2 (enExample) |
| CA (1) | CA2705600C (enExample) |
| NZ (1) | NZ585162A (enExample) |
| TW (1) | TWI434886B (enExample) |
| WO (1) | WO2009076109A1 (enExample) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2008252105B2 (en) * | 2007-05-15 | 2011-05-19 | Daikin Industries, Ltd. | Water-repellent oil-repellent antifouling agent having good solubility in solvent |
| US20090148653A1 (en) * | 2007-12-07 | 2009-06-11 | E.I. Du Pont De Nemours And Company | Fluoropolymer emulsions |
| US8212064B2 (en) * | 2008-05-14 | 2012-07-03 | E.I. Du Pont De Nemours And Company | Ethylene tetrafluoroethylene intermediates |
| US8318877B2 (en) * | 2008-05-20 | 2012-11-27 | E.I. Du Pont De Nemours And Company | Ethylene tetrafluoroethylene (meth)acrylate copolymers |
| JP2012530195A (ja) * | 2009-06-12 | 2012-11-29 | フェデラル−モーグル パワートレイン インコーポレイテッド | 高温耐磨耗性コーティングを有する織物スリーブ、ならびにその組立、構築および硬化方法 |
| US8329822B2 (en) | 2009-11-09 | 2012-12-11 | E.I. Du Pont De Nemours And Company | Fluoropolymer emulsions |
| CN102597101B (zh) * | 2009-11-09 | 2014-09-17 | 纳幕尔杜邦公司 | 含氟聚合物乳液 |
| CN102906204B (zh) * | 2010-05-19 | 2016-05-25 | 索尔维公司 | Pvdf涂覆组合物 |
| US8551895B2 (en) * | 2010-12-22 | 2013-10-08 | Kimberly-Clark Worldwide, Inc. | Nonwoven webs having improved barrier properties |
| US9708755B2 (en) * | 2011-07-05 | 2017-07-18 | Luna Innovations Incorporated | Fluid-resistant textile fabrics and methods |
| MX366743B (es) * | 2012-04-13 | 2019-07-04 | Sigma Alimentos Sa De Cv | Papel o cartón hidrofóbico con nanopartículas auto-ensambladas y método para elaborarlo. |
| US20140106165A1 (en) * | 2012-10-12 | 2014-04-17 | Georgia-Pacific Chemicals Llc | Paper with higher oil repellency |
| WO2014136895A1 (ja) * | 2013-03-06 | 2014-09-12 | ユニマテック株式会社 | 含フッ素オリゴマー、それを用いたナノシリカコンポジット粒子およびそれらの製造法 |
| EP2966101B1 (en) * | 2013-03-06 | 2021-12-29 | Unimatec Co., Ltd. | Fluorine-containing oligomer, nano-silica composite particles using same, and preparation method for both |
| US9688797B2 (en) * | 2013-06-28 | 2017-06-27 | Daikin Industries, Ltd. | Surface treatment agent |
| WO2016176394A1 (en) * | 2015-04-30 | 2016-11-03 | The Chemours Company Tt, Llc | Ethylenically crosslinkable fluorinated polymer additives for architectural coatings |
| PL3332441T3 (pl) * | 2015-08-04 | 2024-02-12 | Solvay Sa | Niewodne kompozycje elektrolitowe zawierające szczawianofosforany litu |
| JP7239846B2 (ja) * | 2018-11-08 | 2023-03-15 | ダイキン工業株式会社 | 被覆粒子、正極、負極、全固体電池、及び、硫化物系全固体電池用コーティング組成物 |
| TWI682084B (zh) * | 2019-01-04 | 2020-01-11 | 遠東新世紀股份有限公司 | 無氟撥水劑的製造方法與撥水織物 |
| CN113913008B (zh) * | 2021-11-15 | 2022-06-24 | 聊城鲁西聚碳酸酯有限公司 | 一种光扩散剂和阻燃型光扩散聚碳酸酯组合物及其制备方法 |
Family Cites Families (56)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3282905A (en) * | 1961-05-03 | 1966-11-01 | Du Pont | Fluorine containing esters and polymers thereof |
| US3592679A (en) * | 1969-05-29 | 1971-07-13 | Cabot Corp | Surface treatment of polymeric materials |
| CA1022182A (en) * | 1972-09-19 | 1977-12-06 | Horst Jager | Process for the manufacture of perfluoroalkyl esters |
| CA1023768A (en) * | 1972-12-21 | 1978-01-03 | Horst Jager | Polyfluoroalkyl iodides, process for their manufacture, and their use |
| US4742140A (en) * | 1986-01-23 | 1988-05-03 | E. I. Du Pont De Nemours And Company | Oil- and water-repellent copolymers |
| US4795793A (en) * | 1986-12-05 | 1989-01-03 | Daikin Industries Ltd. | Fluorine-containing copolymer and oil and water repellent composition containing the same |
| JPH03244996A (ja) | 1990-02-22 | 1991-10-31 | Matsushita Refrig Co Ltd | 撥水性コーティング用組成物及び撥水性コーティング用組成物を用いた熱交換器 |
| US4983459A (en) * | 1990-04-03 | 1991-01-08 | Ppg Industries, Inc. | Chemically reacted glass surface |
| US5308705A (en) * | 1990-04-03 | 1994-05-03 | Ppg Industries, Inc. | Water repellent surface treatment |
| KR100231226B1 (ko) * | 1991-07-10 | 1999-11-15 | 스프레이그 로버트 월터 | 발수 처리용 및 발유 처리용 플루오로케미칼 조성물 |
| DE69413985T2 (de) * | 1993-07-29 | 1999-04-22 | E.I. Du Pont De Nemours And Co., Wilmington, Del. | Verfahren zur herstellung von perfluoroalkyljodid |
| WO1995011877A1 (fr) | 1993-10-27 | 1995-05-04 | Elf Atochem S.A. | Alcools polyfluores et leurs procedes de preparation |
| JP3239645B2 (ja) * | 1994-10-24 | 2001-12-17 | ダイキン工業株式会社 | 含フッ素系重合体水性分散液 |
| JP2986011B2 (ja) | 1995-03-30 | 1999-12-06 | 株式会社神戸製鋼所 | アルミニウムフィン用撥水性塗料及び撥水性が優れたフィン用アルミニウム板材 |
| US5888290A (en) * | 1996-05-24 | 1999-03-30 | Minnesota Mining And Manufacturing Company | Composition and process for imparting durable repellency to substrates |
| US5908663A (en) * | 1996-02-01 | 1999-06-01 | Minnesota Mining And Manufacturing Company | Topical carpet treatment |
| JPH09296134A (ja) | 1996-04-26 | 1997-11-18 | Shin Etsu Chem Co Ltd | 撥水撥油性を有する粉体及びその製造方法 |
| TW494125B (en) * | 1997-07-11 | 2002-07-11 | Rohm And Haas Compary | Preparation of fluorinated polymers |
| US6121372A (en) * | 1998-03-06 | 2000-09-19 | Nippon Mektron Limited | Aqueous emulsion component for a water- and oil-repellant agent |
| US6326447B1 (en) * | 1998-06-19 | 2001-12-04 | E. I. Du Pont De Nemours And Company | Polymeric compositions for soil release on fabrics |
| JP4215889B2 (ja) | 1999-03-15 | 2009-01-28 | 東レ・ダウコーニング株式会社 | 含フッ素シラン化合物、防汚性組成物及び防汚性物品 |
| US6653511B2 (en) * | 2001-07-10 | 2003-11-25 | E. I. Du Pont De Nemours And Company | Perfluoropolyether primary bromides and iodides |
| JP3867548B2 (ja) | 2001-10-26 | 2007-01-10 | 日本曹達株式会社 | 撥水性膜及びその製造方法 |
| JP2003147340A (ja) | 2001-11-16 | 2003-05-21 | Toto Ltd | 超撥水剤およびそれを用いて作製される超撥水材 |
| JP4329559B2 (ja) | 2003-05-02 | 2009-09-09 | ダイキン工業株式会社 | 含フッ素重合体を含んでなる表面処理剤 |
| JP4329760B2 (ja) * | 2003-06-09 | 2009-09-09 | ダイキン工業株式会社 | ケイ素を含有する含フッ素表面処理剤 |
| EP1650261A4 (en) * | 2003-07-18 | 2008-02-27 | Kaneka Corp | HARDENING COMPOSITION |
| CN1493601A (zh) * | 2003-07-23 | 2004-05-05 | 华东理工大学 | 一种水乳型含氟拒水拒油剂及其制备方法 |
| JP2005097369A (ja) | 2003-09-22 | 2005-04-14 | Shin Etsu Chem Co Ltd | 硬化性フルオロポリエーテル系ゴム組成物及びゴム製品 |
| JP2004107673A (ja) * | 2003-09-29 | 2004-04-08 | Kao Corp | 含フッ素高分子物質及び化粧料 |
| US20050095933A1 (en) * | 2003-11-03 | 2005-05-05 | Kimbrell William C. | Textile substrates, compositions useful for treating textile substrates, and related methods |
| JP2005208290A (ja) | 2004-01-22 | 2005-08-04 | Konica Minolta Opto Inc | 防汚性光学薄膜、防汚性反射防止フィルム及びそれを用いた偏光板、表示装置 |
| DE102004008772A1 (de) * | 2004-02-23 | 2005-09-08 | Institut für Neue Materialien Gemeinnützige GmbH | Abriebbeständige und alkalibeständige Beschichtungen oder Formkörper mit Niedrigenergieoberfläche |
| FR2868443B1 (fr) * | 2004-03-31 | 2006-06-02 | Rhodia Chimie Sa | Composition mixte silicone-compose organique fluore pour conferer de l'oleophobie et/ou de l'hydrophobie a un materiau textile |
| CN1690142A (zh) | 2004-04-19 | 2005-11-02 | 河南大学 | 含氟纳米SiO2复合不粘性涂层材料制备方法 |
| WO2005103175A1 (en) * | 2004-04-22 | 2005-11-03 | Jsr Corporation | Low refractive index coating composition |
| US7037966B2 (en) * | 2004-06-23 | 2006-05-02 | Arkema Inc. | Stain resistant coating |
| CN100558754C (zh) * | 2004-06-25 | 2009-11-11 | 大金工业株式会社 | 含有含氟共聚物的污垢脱离剂及其制造方法 |
| EP2028228B1 (en) | 2004-10-25 | 2018-12-12 | IGM Group B.V. | Functionalized nanoparticles |
| KR101220567B1 (ko) | 2004-11-15 | 2013-01-10 | 제이에스알 가부시끼가이샤 | 경화성 수지 조성물 및 이를 포함하는 경화막 및 적층체 |
| WO2006051634A1 (ja) | 2004-11-15 | 2006-05-18 | Jsr Corporation | 液状硬化性樹脂組成物及びそれを用いた積層体の製造方法 |
| KR101213367B1 (ko) | 2004-11-15 | 2012-12-17 | 제이에스알 가부시끼가이샤 | 경화성 수지 조성물, 이를 포함하는 경화막 및 적층체 |
| EP1841819A1 (en) | 2004-12-07 | 2007-10-10 | Yissum Research Development Company Of The Hebrew University Of Jerusalem | Spherical composites entrapping nanoparticles, processes of preparing same and uses thereof |
| JP2006219657A (ja) | 2005-01-13 | 2006-08-24 | Mitsubishi Rayon Co Ltd | 活性エネルギー線硬化性組成物 |
| TW200700510A (en) | 2005-02-25 | 2007-01-01 | Optimax Tech Corp | Inorganic-organic hybrid nanocomposite antiglare and antireflection coatings |
| US20060216524A1 (en) * | 2005-03-23 | 2006-09-28 | 3M Innovative Properties Company | Perfluoropolyether urethane additives having (meth)acryl groups and hard coats |
| US8029871B2 (en) * | 2005-06-09 | 2011-10-04 | Hoya Corporation | Method for producing silica aerogel coating |
| JP4726118B2 (ja) | 2005-06-14 | 2011-07-20 | 三菱レイヨン株式会社 | 変性無機微粒子、それを含む硬化性組成物及び積層物 |
| US20060287559A1 (en) * | 2005-06-17 | 2006-12-21 | Friesen Chadron M | Insulated perfluoropolyether alkyl alcohols |
| KR100661806B1 (ko) | 2005-07-21 | 2006-12-28 | 도레이새한 주식회사 | 대전방지 폴리에스테르필름 |
| US20070049676A1 (en) * | 2005-08-26 | 2007-03-01 | Xerox Corporation | Thick electrophotographic imaging member undercoat layers |
| JP4937556B2 (ja) | 2005-09-08 | 2012-05-23 | エスケー化研株式会社 | 塗料組成物 |
| CN1958937A (zh) * | 2005-11-02 | 2007-05-09 | 巨化集团公司 | 一种含氟织物整理剂水乳液 |
| CN101312909B (zh) * | 2005-11-25 | 2011-11-16 | 日挥触媒化成株式会社 | 中空二氧化硅微粒、含有该微粒的透明涂膜形成用组合物、及覆有透明涂膜的基材 |
| DE102006030060A1 (de) | 2006-06-29 | 2008-01-03 | Volkswagen Ag | Verfahren zum stirnseitigen Schweißen von Blechen |
| US20090148653A1 (en) * | 2007-12-07 | 2009-06-11 | E.I. Du Pont De Nemours And Company | Fluoropolymer emulsions |
-
2008
- 2008-09-25 US US12/237,446 patent/US20090148653A1/en not_active Abandoned
- 2008-11-11 US US12/268,470 patent/US8314037B2/en not_active Expired - Fee Related
- 2008-11-24 TW TW97145374A patent/TWI434886B/zh not_active IP Right Cessation
- 2008-12-03 AU AU2008335494A patent/AU2008335494B2/en not_active Ceased
- 2008-12-03 CN CN200880119194XA patent/CN101889035B/zh not_active Expired - Fee Related
- 2008-12-03 NZ NZ585162A patent/NZ585162A/en not_active IP Right Cessation
- 2008-12-03 JP JP2010537022A patent/JP5536663B2/ja not_active Expired - Fee Related
- 2008-12-03 AT AT08860216T patent/ATE547444T1/de active
- 2008-12-03 WO PCT/US2008/085298 patent/WO2009076109A1/en not_active Ceased
- 2008-12-03 CA CA2705600A patent/CA2705600C/en not_active Expired - Fee Related
- 2008-12-03 KR KR1020107014741A patent/KR101589319B1/ko not_active Expired - Fee Related
- 2008-12-03 EP EP20080860216 patent/EP2217630B1/en not_active Not-in-force
Also Published As
| Publication number | Publication date |
|---|---|
| TWI434886B (zh) | 2014-04-21 |
| AU2008335494A1 (en) | 2009-06-18 |
| HK1150619A1 (en) | 2012-01-06 |
| TW200934820A (en) | 2009-08-16 |
| ATE547444T1 (de) | 2012-03-15 |
| US8314037B2 (en) | 2012-11-20 |
| CN101889035A (zh) | 2010-11-17 |
| EP2217630B1 (en) | 2012-02-29 |
| CA2705600C (en) | 2016-06-21 |
| WO2009076109A1 (en) | 2009-06-18 |
| CN101889035B (zh) | 2013-03-13 |
| CA2705600A1 (en) | 2009-06-18 |
| JP2011506640A (ja) | 2011-03-03 |
| US20090149096A1 (en) | 2009-06-11 |
| EP2217630A1 (en) | 2010-08-18 |
| KR101589319B1 (ko) | 2016-01-27 |
| US20090148653A1 (en) | 2009-06-11 |
| AU2008335494B2 (en) | 2013-10-10 |
| NZ585162A (en) | 2011-11-25 |
| KR20100110810A (ko) | 2010-10-13 |
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Free format text: JAPANESE INTERMEDIATE CODE: R250 |
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| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
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| LAPS | Cancellation because of no payment of annual fees |