TWI302165B - - Google Patents
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- TWI302165B TWI302165B TW091108458A TW91108458A TWI302165B TW I302165 B TWI302165 B TW I302165B TW 091108458 A TW091108458 A TW 091108458A TW 91108458 A TW91108458 A TW 91108458A TW I302165 B TWI302165 B TW I302165B
- Authority
- TW
- Taiwan
- Prior art keywords
- water
- group
- oil repellent
- surfactant
- polymerization
- Prior art date
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 85
- 238000006116 polymerization reaction Methods 0.000 claims description 74
- 239000000203 mixture Substances 0.000 claims description 54
- 239000005871 repellent Substances 0.000 claims description 54
- 230000002940 repellent Effects 0.000 claims description 41
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 39
- 239000004094 surface-active agent Substances 0.000 claims description 39
- -1 oxime ester Chemical class 0.000 claims description 37
- 229920000642 polymer Polymers 0.000 claims description 34
- 125000000217 alkyl group Chemical group 0.000 claims description 28
- 229910052799 carbon Inorganic materials 0.000 claims description 23
- 150000001875 compounds Chemical class 0.000 claims description 22
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 21
- 239000002736 nonionic surfactant Substances 0.000 claims description 21
- 239000012736 aqueous medium Substances 0.000 claims description 14
- 239000012948 isocyanate Substances 0.000 claims description 12
- 230000002079 cooperative effect Effects 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 239000000126 substance Substances 0.000 claims description 8
- 239000003093 cationic surfactant Substances 0.000 claims description 7
- 150000002009 diols Chemical class 0.000 claims description 7
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 125000001153 fluoro group Chemical group F* 0.000 claims description 6
- SDXAWLJRERMRKF-UHFFFAOYSA-N 3,5-dimethyl-1h-pyrazole Chemical compound CC=1C=C(C)NN=1 SDXAWLJRERMRKF-UHFFFAOYSA-N 0.000 claims description 5
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 claims description 5
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 claims description 3
- XKVUYEYANWFIJX-UHFFFAOYSA-N 5-methyl-1h-pyrazole Chemical compound CC1=CC=NN1 XKVUYEYANWFIJX-UHFFFAOYSA-N 0.000 claims description 3
- 239000013543 active substance Substances 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 238000007720 emulsion polymerization reaction Methods 0.000 claims description 2
- 239000002609 medium Substances 0.000 claims description 2
- 125000000962 organic group Chemical group 0.000 claims description 2
- 150000002896 organic halogen compounds Chemical class 0.000 claims description 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims 1
- 125000005250 alkyl acrylate group Chemical group 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- BDHMBGHSWFWYSP-UHFFFAOYSA-N cimemoxin Chemical compound NNCC1CCCCC1 BDHMBGHSWFWYSP-UHFFFAOYSA-N 0.000 claims 1
- 229920001577 copolymer Polymers 0.000 claims 1
- 239000004643 cyanate ester Substances 0.000 claims 1
- MALGCDOKXMEUNO-UHFFFAOYSA-N cyanic acid;prop-2-enoic acid Chemical compound OC#N.OC(=O)C=C MALGCDOKXMEUNO-UHFFFAOYSA-N 0.000 claims 1
- QPMJENKZJUFOON-PLNGDYQASA-N ethyl (z)-3-chloro-2-cyano-4,4,4-trifluorobut-2-enoate Chemical compound CCOC(=O)C(\C#N)=C(/Cl)C(F)(F)F QPMJENKZJUFOON-PLNGDYQASA-N 0.000 claims 1
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 claims 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims 1
- 239000003921 oil Substances 0.000 description 64
- 239000000178 monomer Substances 0.000 description 43
- 239000004744 fabric Substances 0.000 description 28
- 238000011156 evaluation Methods 0.000 description 21
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 19
- 239000000123 paper Substances 0.000 description 19
- 238000012545 processing Methods 0.000 description 18
- 239000003795 chemical substances by application Substances 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 13
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 12
- 239000000835 fiber Substances 0.000 description 12
- KWIUHFFTVRNATP-UHFFFAOYSA-N glycine betaine Chemical compound C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 12
- 238000000034 method Methods 0.000 description 12
- 238000005406 washing Methods 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
- 229920000233 poly(alkylene oxides) Polymers 0.000 description 11
- 239000000047 product Substances 0.000 description 10
- 229920000742 Cotton Polymers 0.000 description 9
- 125000001931 aliphatic group Chemical group 0.000 description 9
- 125000003342 alkenyl group Chemical group 0.000 description 9
- 238000001035 drying Methods 0.000 description 9
- 239000002245 particle Substances 0.000 description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 8
- 150000002148 esters Chemical class 0.000 description 8
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 7
- 239000003995 emulsifying agent Substances 0.000 description 7
- 229910052731 fluorine Inorganic materials 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 125000002347 octyl 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])[H] 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- 239000002280 amphoteric surfactant Substances 0.000 description 6
- 229960003237 betaine Drugs 0.000 description 6
- 239000003431 cross linking reagent Substances 0.000 description 6
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 5
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 5
- 239000004677 Nylon Substances 0.000 description 5
- 238000007605 air drying Methods 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 239000006185 dispersion Substances 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 229920001778 nylon Polymers 0.000 description 5
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- 239000003021 water soluble solvent Substances 0.000 description 5
- 238000004383 yellowing Methods 0.000 description 5
- FKTXDTWDCPTPHK-UHFFFAOYSA-N 1,1,1,2,3,3,3-heptafluoropropane Chemical compound FC(F)(F)[C](F)C(F)(F)F FKTXDTWDCPTPHK-UHFFFAOYSA-N 0.000 description 4
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 239000004305 biphenyl Substances 0.000 description 4
- 238000004043 dyeing Methods 0.000 description 4
- 201000003373 familial cold autoinflammatory syndrome 3 Diseases 0.000 description 4
- 239000011737 fluorine Substances 0.000 description 4
- 150000002513 isocyanates Chemical class 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- WHIVNJATOVLWBW-SNAWJCMRSA-N methylethyl ketone oxime Chemical compound CC\C(C)=N\O WHIVNJATOVLWBW-SNAWJCMRSA-N 0.000 description 4
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 4
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 4
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 3
- ZRPAUEVGEGEPFQ-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]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 ZRPAUEVGEGEPFQ-UHFFFAOYSA-N 0.000 description 3
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
- DCXXMTOCNZCJGO-UHFFFAOYSA-N Glycerol trioctadecanoate Natural products CCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCC DCXXMTOCNZCJGO-UHFFFAOYSA-N 0.000 description 3
- 239000004640 Melamine resin Substances 0.000 description 3
- 229920000877 Melamine resin Polymers 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- 239000004698 Polyethylene Substances 0.000 description 3
- 239000002202 Polyethylene glycol Substances 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- MBHRHUJRKGNOKX-UHFFFAOYSA-N [(4,6-diamino-1,3,5-triazin-2-yl)amino]methanol Chemical compound NC1=NC(N)=NC(NCO)=N1 MBHRHUJRKGNOKX-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 150000001335 aliphatic alkanes Chemical class 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 description 3
- 235000001159 dosh Nutrition 0.000 description 3
- 244000245171 dosh Species 0.000 description 3
- 238000004945 emulsification Methods 0.000 description 3
- 238000010556 emulsion polymerization method Methods 0.000 description 3
- 230000007613 environmental effect Effects 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 229920000573 polyethylene Polymers 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 239000003505 polymerization initiator Substances 0.000 description 3
- 229920001451 polypropylene glycol Polymers 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 230000035807 sensation Effects 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 125000005504 styryl group Chemical group 0.000 description 3
- 229920002994 synthetic fiber Polymers 0.000 description 3
- 239000012209 synthetic fiber Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- 239000002759 woven fabric Substances 0.000 description 3
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 2
- FFJCNSLCJOQHKM-CLFAGFIQSA-N (z)-1-[(z)-octadec-9-enoxy]octadec-9-ene Chemical compound CCCCCCCC\C=C/CCCCCCCCOCCCCCCCC\C=C/CCCCCCCC FFJCNSLCJOQHKM-CLFAGFIQSA-N 0.000 description 2
- MPNXSZJPSVBLHP-UHFFFAOYSA-N 2-chloro-n-phenylpyridine-3-carboxamide Chemical compound ClC1=NC=CC=C1C(=O)NC1=CC=CC=C1 MPNXSZJPSVBLHP-UHFFFAOYSA-N 0.000 description 2
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 2
- NECRQCBKTGZNMH-UHFFFAOYSA-N 3,5-dimethylhex-1-yn-3-ol Chemical compound CC(C)CC(C)(O)C#C NECRQCBKTGZNMH-UHFFFAOYSA-N 0.000 description 2
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- CNWGPEVNWVZJAN-UHFFFAOYSA-N CCC(C)=NO.N=C=O Chemical group CCC(C)=NO.N=C=O CNWGPEVNWVZJAN-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 2
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- 239000005642 Oleic acid Substances 0.000 description 2
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 2
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical class CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 2
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 150000001346 alkyl aryl ethers Chemical class 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 239000010425 asbestos Substances 0.000 description 2
- 125000002511 behenyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 229920001400 block copolymer Polymers 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000012986 chain transfer agent Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- VEZUQRBDRNJBJY-UHFFFAOYSA-N cyclohexanone oxime Chemical compound ON=C1CCCCC1 VEZUQRBDRNJBJY-UHFFFAOYSA-N 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- 210000003298 dental enamel Anatomy 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-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
- 230000000694 effects Effects 0.000 description 2
- 230000001804 emulsifying effect Effects 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- 229960002446 octanoic acid Drugs 0.000 description 2
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 2
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 2
- 239000012188 paraffin wax Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 229910052895 riebeckite Inorganic materials 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000000600 sorbitol Substances 0.000 description 2
- 239000003039 volatile agent Substances 0.000 description 2
- 210000002268 wool Anatomy 0.000 description 2
- RGHNJXZEOKUKBD-NRXMZTRTSA-N (2r,3r,4r,5s)-2,3,4,5,6-pentahydroxyhexanoic acid Chemical compound OC[C@H](O)[C@@H](O)[C@@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-NRXMZTRTSA-N 0.000 description 1
- NKJOXAZJBOMXID-UHFFFAOYSA-N 1,1'-Oxybisoctane Chemical compound CCCCCCCCOCCCCCCCC NKJOXAZJBOMXID-UHFFFAOYSA-N 0.000 description 1
- BQCIDUSAKPWEOX-UHFFFAOYSA-N 1,1-Difluoroethene Chemical compound FC(F)=C BQCIDUSAKPWEOX-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
- D06M15/21—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/356—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of other unsaturated compounds containing nitrogen, sulfur, silicon or phosphorus atoms
- D06M15/3562—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of other unsaturated compounds containing nitrogen, sulfur, silicon or phosphorus atoms containing nitrogen
-
- 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
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K3/00—Materials not provided for elsewhere
- C09K3/18—Materials not provided for elsewhere for application to surfaces to minimize adherence of ice, mist or water thereto; Thawing or antifreeze materials for application to surfaces
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
- D06M15/21—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/263—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acids; Salts or esters thereof
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
- D06M15/21—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/263—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acids; Salts or esters thereof
- D06M15/277—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acids; Salts or esters thereof containing fluorine
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- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
- D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/564—Polyureas, polyurethanes or other polymers having ureide or urethane links; Precondensation products forming them
- D06M15/576—Polyureas, polyurethanes or other polymers having ureide or urethane links; Precondensation products forming them containing fluorine
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- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M23/00—Treatment of fibres, threads, yarns, fabrics or fibrous goods made from such materials, characterised by the process
- D06M23/10—Processes in which the treating agent is dissolved or dispersed in organic solvents; Processes for the recovery of organic solvents thereof
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- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Textile Engineering (AREA)
- Organic Chemistry (AREA)
- Combustion & Propulsion (AREA)
- Materials Engineering (AREA)
- Medicinal Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Polymers & Plastics (AREA)
- Dispersion Chemistry (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Materials Applied To Surfaces To Minimize Adherence Of Mist Or Water (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Paper (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2001127977A JP5040046B2 (ja) | 2001-04-25 | 2001-04-25 | 撥水撥油剤組成物 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TWI302165B true TWI302165B (cg-RX-API-DMAC7.html) | 2008-10-21 |
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| Country | Link |
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| EP (1) | EP1394232B1 (cg-RX-API-DMAC7.html) |
| JP (1) | JP5040046B2 (cg-RX-API-DMAC7.html) |
| KR (2) | KR100988182B1 (cg-RX-API-DMAC7.html) |
| CN (1) | CN1245425C (cg-RX-API-DMAC7.html) |
| TW (1) | TWI302165B (cg-RX-API-DMAC7.html) |
| WO (1) | WO2002088272A1 (cg-RX-API-DMAC7.html) |
Families Citing this family (41)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2003221406A (ja) | 2002-01-31 | 2003-08-05 | Asahi Glass Co Ltd | 水性分散液 |
| TW200416277A (en) * | 2002-10-15 | 2004-09-01 | Asahi Glass Co Ltd | Water-and-oil repellant composition |
| JP4206767B2 (ja) * | 2003-02-07 | 2009-01-14 | 旭硝子株式会社 | 撥水撥油剤水性組成物 |
| US7728064B2 (en) | 2003-11-13 | 2010-06-01 | Daikin Industries, Ltd. | Aqueous liquid dispersion of water and oil repellent agent containing nonionic surfactant |
| EP1728806B1 (en) * | 2004-03-23 | 2011-01-19 | Asahi Glass Company, Limited | Waterproofing/oilproofing agent composition |
| JP4752197B2 (ja) * | 2004-06-04 | 2011-08-17 | ユニマテック株式会社 | 撥水撥油剤の製造法 |
| US7345123B2 (en) * | 2004-12-28 | 2008-03-18 | 3M Innovative Properties Company | Fluoroacrylate-multifunctional acrylate copolymer compositions |
| JP2006307129A (ja) * | 2005-03-30 | 2006-11-09 | Asahi Glass Co Ltd | 撥油性組成物および撥油膜 |
| CN101248147A (zh) * | 2005-08-30 | 2008-08-20 | 旭硝子株式会社 | 水基表面处理剂以及经表面处理的结构体 |
| US20070265412A1 (en) * | 2006-05-09 | 2007-11-15 | 3M Innovative Properties Company | Extenders for fluorochemical treatment of fibrous substrates |
| WO2008087915A1 (ja) * | 2007-01-17 | 2008-07-24 | Asahi Glass Company, Limited | 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 |
| US7964657B2 (en) * | 2007-03-23 | 2011-06-21 | Peach State Labs, Inc. | Polymeric dispersions and applications thereof |
| JP5572385B2 (ja) * | 2007-04-27 | 2014-08-13 | 旭硝子株式会社 | 撥水撥油剤組成物、その製造方法および物品 |
| JP5394003B2 (ja) * | 2007-08-30 | 2014-01-22 | 株式会社ダイセル | 共重合体 |
| ATE533800T1 (de) * | 2007-09-15 | 2011-12-15 | Huntsman Textile Effects Ger | Fluorhaltiges polymer und siloxan enthaltende zusammensetzungen |
| US20090256103A1 (en) * | 2008-04-10 | 2009-10-15 | Punjab University | Aqueous water and oil repellent composition |
| JP5177225B2 (ja) * | 2008-06-17 | 2013-04-03 | ダイキン工業株式会社 | 繊維製品の撥水撥油処理方法 |
| CN102197106A (zh) * | 2008-10-24 | 2011-09-21 | 旭硝子株式会社 | 斥水斥油剂组合物及其制造方法 |
| JP5216554B2 (ja) * | 2008-11-28 | 2013-06-19 | 株式会社ダイセル | 共重合体 |
| KR101579846B1 (ko) * | 2008-12-24 | 2015-12-24 | 주식회사 이엔에프테크놀로지 | 포토레지스트 패턴 제거용 조성물 및 이를 이용한 금속 패턴의 형성 방법 |
| US7901589B2 (en) * | 2009-06-29 | 2011-03-08 | E.I. Du Pont De Nemours And Company | Propanediol soil resist compositions |
| US8357621B2 (en) | 2009-06-29 | 2013-01-22 | E.I. Du Pont De Nemours And Company | Soil resist method |
| US9677220B2 (en) | 2009-11-20 | 2017-06-13 | Daikin Industries, Ltd. | Fluoropolymers and treatment agent |
| EP2501851B1 (en) * | 2009-11-20 | 2015-03-25 | Daikin Industries, Ltd. | Fluoropolymers and surface treatment agent |
| CN101736582B (zh) * | 2009-12-31 | 2012-07-11 | 安徽中天印染股份有限公司 | 一种取得多功能性纺织物的整理方法 |
| KR101142133B1 (ko) * | 2010-06-08 | 2012-05-10 | 박형준 | 점토블록용 발수제 조성물 및 이를 이용한 발수성 점토블록의 제조방법 |
| JP5789090B2 (ja) * | 2010-07-30 | 2015-10-07 | 日華化学株式会社 | 撥水撥油剤組成物、機能性繊維製品及び機能性繊維製品の製造方法 |
| TWI402396B (zh) * | 2010-10-06 | 2013-07-21 | Univ Dayeh | Application of sericite in oil - resistant paper |
| CN102174143B (zh) * | 2011-01-29 | 2013-01-09 | 锦州惠发天合化学有限公司 | 一种含氟丙烯酸酯乳液的制备方法 |
| CN102321978A (zh) * | 2011-08-16 | 2012-01-18 | 苏州铭辰无纺布有限公司 | 多功能性sms无纺布的制作方法 |
| US8771470B2 (en) | 2012-01-17 | 2014-07-08 | Agc Chemicals Americas, Inc. | Method of preparing a treated article and treated article formed therefrom |
| EP2826918B1 (en) | 2012-03-16 | 2020-02-12 | Daikin Industries, Ltd. | Water-resistant/oil-resistant agent for paper |
| CN102643396B (zh) * | 2012-03-28 | 2014-02-26 | 成都德美精英化工有限公司 | 一种防水防油含氟硅丙烯酸整理剂的制备方法及其应用 |
| CN102634980B (zh) * | 2012-04-19 | 2014-07-23 | 常州大学 | 用于织物的含氟防水剂及其制备方法 |
| US20160251468A1 (en) * | 2013-11-01 | 2016-09-01 | Unimatec Co., Ltd. | Fluorine-containing polymer and surface-modifying agent containing the same as active ingredient |
| CN107207689B (zh) * | 2015-01-20 | 2021-09-24 | 宣伟投资管理有限公司 | 聚合物、涂料组合物、经涂布制品及其相关方法 |
| CN106563619A (zh) * | 2016-10-14 | 2017-04-19 | 上海稷以科技有限公司 | 在物体表面形成保护层的方法及表面形成有保护层的产品 |
| US20210261706A1 (en) * | 2018-07-26 | 2021-08-26 | Showa Denko Materials Co., Ltd. | Resin composition, heat storage material, and article |
| CN113490552A (zh) * | 2019-01-03 | 2021-10-08 | Gcp应用技术有限公司 | 隧道防水组合物和体系 |
| WO2021161593A1 (ja) * | 2020-02-10 | 2021-08-19 | ユニマテック株式会社 | 含フッ素重合体を有効成分とする柔軟性撥水撥油剤 |
| CN111286982B (zh) * | 2020-04-14 | 2021-12-14 | 北京邦维高科特种纺织品有限责任公司 | 拒水拒油整理剂及制备方法和用途，拒水拒油处理方法 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0247489B1 (en) | 1986-05-28 | 1993-08-25 | Daikin Industries, Limited | Fluorine containing water and oil repellent composition |
| JPS6375082A (ja) | 1986-09-18 | 1988-04-05 | Daikin Ind Ltd | エアゾル型撥水撥油剤組成物 |
| JPH01153784A (ja) | 1987-12-11 | 1989-06-15 | Daikin Ind Ltd | 撥水撥油剤組成物 |
| JP3151905B2 (ja) * | 1992-01-31 | 2001-04-03 | 大日本インキ化学工業株式会社 | 安定性の優れたパーフルオロアルキル基含有共重合体非水分散液及び撥水撥油剤 |
| JP3601062B2 (ja) * | 1993-02-24 | 2004-12-15 | 旭硝子株式会社 | 溶剤型表面処理剤組成物 |
| JP3320491B2 (ja) * | 1993-03-24 | 2002-09-03 | 旭硝子株式会社 | 防汚加工剤 |
| JPH07188339A (ja) * | 1993-12-27 | 1995-07-25 | Asahi Glass Co Ltd | 紙用の撥水耐油剤組成物 |
| CA2243772C (en) | 1997-07-23 | 2008-04-15 | Asahi Glass Company Ltd. | Water and oil repellent composition |
| JP3896693B2 (ja) * | 1997-07-23 | 2007-03-22 | 旭硝子株式会社 | 撥水撥油剤組成物 |
| JP2000136377A (ja) | 1998-08-24 | 2000-05-16 | Asahi Glass Co Ltd | 水分散型撥水撥油剤組成物 |
| JP3864591B2 (ja) | 1998-11-26 | 2007-01-10 | 旭硝子株式会社 | 撥水撥油加工剤 |
| JP4510169B2 (ja) * | 1999-03-11 | 2010-07-21 | 石原薬品株式会社 | フルオロ飽和炭化水素基含有化合物、その製造方法、及び表面処理剤及び塗料添加剤 |
| JP2001107031A (ja) * | 1999-10-12 | 2001-04-17 | Asahi Glass Co Ltd | 動的表面張力が低い撥水撥油剤組成物および撥水撥油処理方法 |
| DE60041121D1 (de) | 1999-10-29 | 2009-01-29 | Asahi Glass Co Ltd | In wasser dispergierte wasser- und ölabweisende zusammensetzung und verfahren zu ihrer herstellung |
-
2001
- 2001-04-25 JP JP2001127977A patent/JP5040046B2/ja not_active Expired - Fee Related
-
2002
- 2002-04-19 KR KR1020037013957A patent/KR100988182B1/ko not_active Expired - Fee Related
- 2002-04-19 CN CNB028087259A patent/CN1245425C/zh not_active Expired - Fee Related
- 2002-04-19 EP EP02720538A patent/EP1394232B1/en not_active Expired - Lifetime
- 2002-04-19 KR KR1020087029387A patent/KR101001127B1/ko not_active Expired - Fee Related
- 2002-04-19 WO PCT/JP2002/003956 patent/WO2002088272A1/ja not_active Ceased
- 2002-04-24 TW TW091108458A patent/TWI302165B/zh not_active IP Right Cessation
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2003
- 2003-10-27 US US10/692,691 patent/US6933338B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| WO2002088272A1 (en) | 2002-11-07 |
| KR100988182B1 (ko) | 2010-10-18 |
| CN1245425C (zh) | 2006-03-15 |
| JP5040046B2 (ja) | 2012-10-03 |
| CN1503833A (zh) | 2004-06-09 |
| US6933338B2 (en) | 2005-08-23 |
| EP1394232A4 (en) | 2006-05-31 |
| KR20080112423A (ko) | 2008-12-24 |
| KR20040015150A (ko) | 2004-02-18 |
| KR101001127B1 (ko) | 2010-12-14 |
| JP2002322465A (ja) | 2002-11-08 |
| EP1394232A1 (en) | 2004-03-03 |
| US20040087695A1 (en) | 2004-05-06 |
| EP1394232B1 (en) | 2012-08-29 |
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