NZ583941A - Perfluoroalkyl sulphonamide polymers prepared by free-radical polymerisation of vinylic monomers - Google Patents
Perfluoroalkyl sulphonamide polymers prepared by free-radical polymerisation of vinylic monomersInfo
- Publication number
- NZ583941A NZ583941A NZ583941A NZ58394108A NZ583941A NZ 583941 A NZ583941 A NZ 583941A NZ 583941 A NZ583941 A NZ 583941A NZ 58394108 A NZ58394108 A NZ 58394108A NZ 583941 A NZ583941 A NZ 583941A
- Authority
- NZ
- New Zealand
- Prior art keywords
- fluoropolymer
- water
- units
- repellency
- substrate
- Prior art date
Links
- 239000000178 monomer Substances 0.000 title claims abstract description 112
- 125000002348 vinylic group Chemical group 0.000 title claims abstract description 19
- 229940124530 sulfonamide Drugs 0.000 title abstract 2
- -1 Perfluoroalkyl sulphonamide Chemical compound 0.000 title description 42
- 229920000642 polymer Polymers 0.000 title description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 173
- 229920002313 fluoropolymer Polymers 0.000 claims abstract description 171
- 239000004811 fluoropolymer Substances 0.000 claims abstract description 171
- 239000000758 substrate Substances 0.000 claims abstract description 97
- 238000000034 method Methods 0.000 claims abstract description 74
- 239000011737 fluorine Substances 0.000 claims abstract description 72
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 72
- 239000010985 leather Substances 0.000 claims abstract description 64
- 239000001257 hydrogen Substances 0.000 claims abstract description 36
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 36
- 230000002209 hydrophobic effect Effects 0.000 claims abstract description 35
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims abstract description 28
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 24
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 24
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 15
- 239000001301 oxygen Substances 0.000 claims abstract description 15
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 15
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 13
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 11
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 10
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract 4
- 238000011282 treatment Methods 0.000 claims description 88
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 71
- 238000012360 testing method Methods 0.000 claims description 42
- 238000007865 diluting Methods 0.000 claims description 35
- 230000000052 comparative effect Effects 0.000 claims description 28
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 21
- 238000010348 incorporation Methods 0.000 claims description 17
- 239000006185 dispersion Substances 0.000 claims description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
- 239000012986 chain transfer agent Substances 0.000 claims description 12
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 10
- 239000003960 organic solvent Substances 0.000 claims description 10
- 125000006659 (C1-C20) hydrocarbyl group Chemical group 0.000 claims description 6
- 239000000839 emulsion Substances 0.000 claims description 2
- 125000000743 hydrocarbylene group Chemical group 0.000 claims description 2
- 230000002940 repellent Effects 0.000 claims 1
- 239000005871 repellent Substances 0.000 claims 1
- 229920001577 copolymer Polymers 0.000 abstract description 8
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 111
- 239000003921 oil Substances 0.000 description 65
- 241000283690 Bos taurus Species 0.000 description 58
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 51
- 239000000203 mixture Substances 0.000 description 34
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 32
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 30
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 30
- 238000011156 evaluation Methods 0.000 description 29
- 239000007787 solid Substances 0.000 description 26
- 229920002554 vinyl polymer Polymers 0.000 description 25
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 24
- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 description 20
- 239000003999 initiator Substances 0.000 description 20
- 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 16
- 229910052757 nitrogen Inorganic materials 0.000 description 15
- 239000007921 spray Substances 0.000 description 15
- 235000019687 Lamb Nutrition 0.000 description 14
- 238000003756 stirring Methods 0.000 description 13
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 12
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 12
- 235000019253 formic acid Nutrition 0.000 description 12
- 238000004821 distillation Methods 0.000 description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
- 230000008569 process Effects 0.000 description 10
- 238000006116 polymerization reaction Methods 0.000 description 9
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 8
- 150000003254 radicals Chemical class 0.000 description 8
- 238000012546 transfer Methods 0.000 description 8
- CCJAYIGMMRQRAO-UHFFFAOYSA-N 2-[4-[(2-hydroxyphenyl)methylideneamino]butyliminomethyl]phenol Chemical compound OC1=CC=CC=C1C=NCCCCN=CC1=CC=CC=C1O CCJAYIGMMRQRAO-UHFFFAOYSA-N 0.000 description 7
- 238000007720 emulsion polymerization reaction Methods 0.000 description 7
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 150000001298 alcohols Chemical class 0.000 description 5
- 229910021529 ammonia Inorganic materials 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 239000000975 dye Substances 0.000 description 5
- 238000004043 dyeing Methods 0.000 description 5
- 150000002430 hydrocarbons Chemical group 0.000 description 5
- 238000006386 neutralization reaction Methods 0.000 description 5
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 5
- 238000009736 wetting Methods 0.000 description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 4
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 4
- 150000004996 alkyl benzenes Chemical class 0.000 description 4
- 150000008064 anhydrides Chemical class 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 150000001735 carboxylic acids Chemical class 0.000 description 4
- 239000004359 castor oil Substances 0.000 description 4
- 235000019438 castor oil Nutrition 0.000 description 4
- 235000014113 dietary fatty acids Nutrition 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 229930195729 fatty acid Natural products 0.000 description 4
- 239000000194 fatty acid Substances 0.000 description 4
- 150000004665 fatty acids Chemical class 0.000 description 4
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 4
- 238000010526 radical polymerization reaction Methods 0.000 description 4
- 238000012712 reversible addition−fragmentation chain-transfer polymerization Methods 0.000 description 4
- WBHHMMIMDMUBKC-XLNAKTSKSA-N ricinelaidic acid Chemical compound CCCCCC[C@@H](O)C\C=C\CCCCCCCC(O)=O WBHHMMIMDMUBKC-XLNAKTSKSA-N 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 4
- 238000002604 ultrasonography Methods 0.000 description 4
- BULLJMKUVKYZDJ-UHFFFAOYSA-N 1,1,1,2,2,3,3,4,4,5,5,6,6-tridecafluoro-6-iodohexane Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)I BULLJMKUVKYZDJ-UHFFFAOYSA-N 0.000 description 3
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 239000004280 Sodium formate Substances 0.000 description 3
- 238000007792 addition Methods 0.000 description 3
- 125000005250 alkyl acrylate group Chemical group 0.000 description 3
- 230000007246 mechanism Effects 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- HLBBKKJFGFRGMU-UHFFFAOYSA-M sodium formate Chemical compound [Na+].[O-]C=O HLBBKKJFGFRGMU-UHFFFAOYSA-M 0.000 description 3
- 235000019254 sodium formate Nutrition 0.000 description 3
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 3
- 238000010998 test method Methods 0.000 description 3
- BFSUQRCCKXZXEX-UHFFFAOYSA-N 2-methoxypropan-2-ol Chemical compound COC(C)(C)O BFSUQRCCKXZXEX-UHFFFAOYSA-N 0.000 description 2
- FRQQKWGDKVGLFI-UHFFFAOYSA-N 2-methylundecane-2-thiol Chemical compound CCCCCCCCCC(C)(C)S FRQQKWGDKVGLFI-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 150000001242 acetic acid derivatives Chemical class 0.000 description 2
- 238000010560 atom transfer radical polymerization reaction Methods 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 229960001701 chloroform Drugs 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- 150000001991 dicarboxylic acids Chemical class 0.000 description 2
- NXWVPIWRMPQYEX-UHFFFAOYSA-N ethyl 2-(benzenecarbonothioylsulfanyl)propanoate Chemical compound CCOC(=O)C(C)SC(=S)C1=CC=CC=C1 NXWVPIWRMPQYEX-UHFFFAOYSA-N 0.000 description 2
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethyl mercaptane Natural products CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 2
- 229940011051 isopropyl acetate Drugs 0.000 description 2
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- PBOSTUDLECTMNL-UHFFFAOYSA-N lauryl acrylate Chemical compound CCCCCCCCCCCCOC(=O)C=C PBOSTUDLECTMNL-UHFFFAOYSA-N 0.000 description 2
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 2
- 238000012705 nitroxide-mediated radical polymerization Methods 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 2
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 2
- ZBZICERRZIMWGX-UHFFFAOYSA-N 1,1,1,2,3,3,4,4,5,5,6,6,6-tridecafluorohexan-2-yl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(F)(C(F)(F)F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F ZBZICERRZIMWGX-UHFFFAOYSA-N 0.000 description 1
- DVQHBFNANVWOEE-UHFFFAOYSA-N 1,1,1,2,3,3,4,4,5,5,6,6,6-tridecafluorohexan-2-yl prop-2-enoate Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(C(F)(F)F)OC(=O)C=C DVQHBFNANVWOEE-UHFFFAOYSA-N 0.000 description 1
- STYXVTBFUKQEKM-UHFFFAOYSA-N 1,1,1,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluorooctan-2-yl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(F)(C(F)(F)F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F STYXVTBFUKQEKM-UHFFFAOYSA-N 0.000 description 1
- WJNKJKGZKFOLOJ-UHFFFAOYSA-N 1-dodecyl-4-ethenylbenzene Chemical compound CCCCCCCCCCCCC1=CC=C(C=C)C=C1 WJNKJKGZKFOLOJ-UHFFFAOYSA-N 0.000 description 1
- LGJCFVYMIJLQJO-UHFFFAOYSA-N 1-dodecylperoxydodecane Chemical compound CCCCCCCCCCCCOOCCCCCCCCCCCC LGJCFVYMIJLQJO-UHFFFAOYSA-N 0.000 description 1
- HLRQDIVVLOCZPH-UHFFFAOYSA-N 1-ethenyl-4-octylbenzene Chemical compound CCCCCCCCC1=CC=C(C=C)C=C1 HLRQDIVVLOCZPH-UHFFFAOYSA-N 0.000 description 1
- ADOYKPDOFQXKEF-UHFFFAOYSA-N 1-ethenyl-4-pentylbenzene Chemical compound CCCCCC1=CC=C(C=C)C=C1 ADOYKPDOFQXKEF-UHFFFAOYSA-N 0.000 description 1
- NNQPQJLMERNWGN-UHFFFAOYSA-N 11-methyldodecyl prop-2-enoate Chemical compound CC(C)CCCCCCCCCCOC(=O)C=C NNQPQJLMERNWGN-UHFFFAOYSA-N 0.000 description 1
- LCPVQAHEFVXVKT-UHFFFAOYSA-N 2-(2,4-difluorophenoxy)pyridin-3-amine Chemical compound NC1=CC=CN=C1OC1=CC=C(F)C=C1F LCPVQAHEFVXVKT-UHFFFAOYSA-N 0.000 description 1
- 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 1
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 1
- HMZGGKJDNBZAEW-UHFFFAOYSA-N 2-[methyl(3,3,4,4,5,5,6,6,6-nonafluorohexylsulfonyl)amino]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCN(C)S(=O)(=O)CCC(F)(F)C(F)(F)C(F)(F)C(F)(F)F HMZGGKJDNBZAEW-UHFFFAOYSA-N 0.000 description 1
- HGKQBLOWECOSMR-UHFFFAOYSA-N 2-[methyl(3,3,4,4,5,5,6,6,6-nonafluorohexylsulfonyl)amino]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCN(C)S(=O)(=O)CCC(F)(F)C(F)(F)C(F)(F)C(F)(F)F HGKQBLOWECOSMR-UHFFFAOYSA-N 0.000 description 1
- HATNGDPVYXXGKR-UHFFFAOYSA-N 2-[methyl(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctylsulfonyl)amino]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCN(C)S(=O)(=O)CCC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F HATNGDPVYXXGKR-UHFFFAOYSA-N 0.000 description 1
- XRXANEMIFVRKLN-UHFFFAOYSA-N 2-hydroperoxy-2-methylbutane Chemical compound CCC(C)(C)OO XRXANEMIFVRKLN-UHFFFAOYSA-N 0.000 description 1
- PABGQABTFFNYFH-UHFFFAOYSA-N 2-methyl-n-octadecylprop-2-enamide Chemical compound CCCCCCCCCCCCCCCCCCNC(=O)C(C)=C PABGQABTFFNYFH-UHFFFAOYSA-N 0.000 description 1
- ROKFKDSZHILENP-UHFFFAOYSA-N 2-methylidenedodecanamide Chemical compound CCCCCCCCCCC(=C)C(N)=O ROKFKDSZHILENP-UHFFFAOYSA-N 0.000 description 1
- RALDEEUHNXQFIN-UHFFFAOYSA-N 2-methylideneicosanamide Chemical compound CCCCCCCCCCCCCCCCCCC(=C)C(N)=O RALDEEUHNXQFIN-UHFFFAOYSA-N 0.000 description 1
- UHQADSBKMJUJEK-UHFFFAOYSA-N 2-methylidenetetradecanamide Chemical compound CCCCCCCCCCCCC(=C)C(N)=O UHQADSBKMJUJEK-UHFFFAOYSA-N 0.000 description 1
- VPKQPPJQTZJZDB-UHFFFAOYSA-N 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl prop-2-enoate Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)CCOC(=O)C=C VPKQPPJQTZJZDB-UHFFFAOYSA-N 0.000 description 1
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 1
- CNCOEDDPFOAUMB-UHFFFAOYSA-N N-Methylolacrylamide Chemical compound OCNC(=O)C=C CNCOEDDPFOAUMB-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000003926 acrylamides Chemical class 0.000 description 1
- 238000012644 addition polymerization Methods 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium peroxydisulfate Substances [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 1
- VAZSKTXWXKYQJF-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)OOS([O-])=O VAZSKTXWXKYQJF-UHFFFAOYSA-N 0.000 description 1
- 229910001870 ammonium persulfate Inorganic materials 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910021538 borax Inorganic materials 0.000 description 1
- UPIWXMRIPODGLE-UHFFFAOYSA-N butyl benzenecarboperoxoate Chemical compound CCCCOOC(=O)C1=CC=CC=C1 UPIWXMRIPODGLE-UHFFFAOYSA-N 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- GRWVQDDAKZFPFI-UHFFFAOYSA-H chromium(III) sulfate Chemical compound [Cr+3].[Cr+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O GRWVQDDAKZFPFI-UHFFFAOYSA-H 0.000 description 1
- FWLDHHJLVGRRHD-UHFFFAOYSA-N decyl prop-2-enoate Chemical compound CCCCCCCCCCOC(=O)C=C FWLDHHJLVGRRHD-UHFFFAOYSA-N 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical group CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 1
- 239000012933 diacyl peroxide Substances 0.000 description 1
- UCQFCFPECQILOL-UHFFFAOYSA-N diethyl hydrogen phosphate Chemical compound CCOP(O)(=O)OCC UCQFCFPECQILOL-UHFFFAOYSA-N 0.000 description 1
- AJFXNBUVIBKWBT-UHFFFAOYSA-N disodium;boric acid;hydrogen borate Chemical compound [Na+].[Na+].OB(O)O.OB(O)O.OB(O)O.OB([O-])[O-] AJFXNBUVIBKWBT-UHFFFAOYSA-N 0.000 description 1
- 125000005022 dithioester group Chemical group 0.000 description 1
- 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 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 1
- RCSQUPAILZWQLY-UHFFFAOYSA-N ethyl 3-(benzenecarbonothioylsulfanyl)propanoate Chemical compound CCOC(=O)CCSC(=S)C1=CC=CC=C1 RCSQUPAILZWQLY-UHFFFAOYSA-N 0.000 description 1
- MHYCRLGKOZWVEF-UHFFFAOYSA-N ethyl acetate;hydrate Chemical compound O.CCOC(C)=O MHYCRLGKOZWVEF-UHFFFAOYSA-N 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 150000002432 hydroperoxides Chemical class 0.000 description 1
- NGYRYRBDIPYKTL-UHFFFAOYSA-N icosyl prop-2-enoate Chemical compound CCCCCCCCCCCCCCCCCCCCOC(=O)C=C NGYRYRBDIPYKTL-UHFFFAOYSA-N 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- SNPAMTGUOWHTMN-UHFFFAOYSA-N n-decyl-2-methylprop-2-enamide Chemical compound CCCCCCCCCCNC(=O)C(C)=C SNPAMTGUOWHTMN-UHFFFAOYSA-N 0.000 description 1
- HOZLHJIPBBRFGM-UHFFFAOYSA-N n-dodecyl-2-methylprop-2-enamide Chemical compound CCCCCCCCCCCCNC(=O)C(C)=C HOZLHJIPBBRFGM-UHFFFAOYSA-N 0.000 description 1
- YRGCLADHMAKURN-UHFFFAOYSA-N n-hexadecyl-2-methylprop-2-enamide Chemical compound CCCCCCCCCCCCCCCCNC(=O)C(C)=C YRGCLADHMAKURN-UHFFFAOYSA-N 0.000 description 1
- FSAJWMJJORKPKS-UHFFFAOYSA-N octadecyl prop-2-enoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)C=C FSAJWMJJORKPKS-UHFFFAOYSA-N 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 239000006174 pH buffer Substances 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 150000004968 peroxymonosulfuric acids Chemical class 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 239000012966 redox initiator Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Substances [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- XZHNPVKXBNDGJD-UHFFFAOYSA-N tetradecyl prop-2-enoate Chemical compound CCCCCCCCCCCCCCOC(=O)C=C XZHNPVKXBNDGJD-UHFFFAOYSA-N 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000012991 xanthate Substances 0.000 description 1
Classifications
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C14—SKINS; HIDES; PELTS; LEATHER
- C14C—CHEMICAL TREATMENT OF HIDES, SKINS OR LEATHER, e.g. TANNING, IMPREGNATING, FINISHING; APPARATUS THEREFOR; COMPOSITIONS FOR TANNING
- C14C9/00—Impregnating leather for preserving, waterproofing, making resistant to heat or similar purposes
-
- 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
-
- 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
-
- 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
- C08F220/62—Monocarboxylic acids having ten or more carbon atoms; Derivatives thereof
- C08F220/68—Esters
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Chemical & Material Sciences (AREA)
- Treatment And Processing Of Natural Fur Or Leather (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Materials Applied To Surfaces To Minimize Adherence Of Mist Or Water (AREA)
- Dispersion Chemistry (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP07117935A EP2045276A1 (en) | 2007-10-05 | 2007-10-05 | Fluoropolymer |
| PCT/US2008/078289 WO2009046016A1 (en) | 2007-10-05 | 2008-09-30 | Fluoropolymer |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NZ583941A true NZ583941A (en) | 2011-07-29 |
Family
ID=38805804
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NZ583941A NZ583941A (en) | 2007-10-05 | 2008-09-30 | Perfluoroalkyl sulphonamide polymers prepared by free-radical polymerisation of vinylic monomers |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US9029471B2 (https=) |
| EP (1) | EP2045276A1 (https=) |
| JP (1) | JP5671342B2 (https=) |
| KR (2) | KR20100072065A (https=) |
| CN (1) | CN101815796A (https=) |
| AU (1) | AU2008308832B2 (https=) |
| CA (1) | CA2700142C (https=) |
| NZ (1) | NZ583941A (https=) |
| WO (1) | WO2009046016A1 (https=) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5855749B2 (ja) * | 2012-07-06 | 2016-02-09 | ダイキン工業株式会社 | 含フッ素重合体の製造方法 |
| EP3279639B1 (en) * | 2015-04-02 | 2020-04-15 | Toray Research Center, Inc. | Method of fabricating sample stage for microspectrometric analysis |
| CN113372475B (zh) * | 2021-06-24 | 2023-03-24 | 齐鲁工业大学 | 一种制备防水聚合物加脂剂的方法 |
| CN120718200B (zh) * | 2025-08-26 | 2025-11-21 | 广州凯恒科塑有限公司 | 一种亲水含氟共聚物助剂、亲水pvdf热收缩材料及其制备方法和应用 |
Family Cites Families (42)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2803615A (en) | 1956-01-23 | 1957-08-20 | Minnesota Mining & Mfg | Fluorocarbon acrylate and methacrylate esters and polymers |
| US3256231A (en) | 1961-05-03 | 1966-06-14 | Du Pont | Polymeric water and oil repellents |
| US3532659A (en) * | 1967-04-26 | 1970-10-06 | Pennsalt Chemicals Corp | Fluorinated organic compounds and polymers thereof |
| FR2034142B1 (https=) | 1969-02-11 | 1975-07-04 | Ugine Kuhlmann | |
| FR2175332A5 (https=) * | 1972-03-10 | 1973-10-19 | Ugine Kuhlmann | |
| US4032495A (en) * | 1972-03-10 | 1977-06-28 | Produits Chimiques Ugine Kuhlmann | Water-repellent and oil-repellent compositions based on fluorine compound |
| FR2319668A1 (fr) | 1975-07-31 | 1977-02-25 | Ugine Kuhlmann | Compositions fluorees a caractere oleofuge et hydrofuge |
| FR2476097A1 (https=) * | 1980-02-19 | 1981-08-21 | Ugine Kuhlmann | |
| FR2579211B1 (fr) * | 1985-03-20 | 1987-09-18 | Atochem | Copolymeres fluores et leur application au traitement hydrophobe et oleophobe de substrats divers |
| FR2588555B1 (fr) * | 1985-10-16 | 1987-12-11 | Atochem | Monomeres acryliques fluores, polymeres en derivant et leur application au traitement hydrofuge et oleofuge de substrats divers |
| US4795793A (en) * | 1986-12-05 | 1989-01-03 | Daikin Industries Ltd. | Fluorine-containing copolymer and oil and water repellent composition containing the same |
| DE3877261T2 (de) * | 1987-05-25 | 1993-05-19 | Daikin Ind Ltd | Copolymer und diesen enthaltende oel- und wasserabweisende zusammensetzung. |
| TNSN89128A1 (fr) | 1988-12-02 | 1991-02-04 | Rohn And Haas Company Independance Mall West | Traitement du cuir avec des copolymeres amphiphites choisis |
| JP2895850B2 (ja) * | 1989-04-12 | 1999-05-24 | 株式会社リコー | 含弗素樹脂分散液の製造方法 |
| DE3931039A1 (de) | 1989-09-16 | 1991-03-28 | Basf Ag | Verwendung von copolymerisaten auf basis von langkettigen ungesaettigten estern und ethylenisch ungesaettigten carbonsaeuren zum hydrophobieren von leder und pelzfellen |
| FR2653772B1 (fr) | 1989-11-02 | 1992-01-17 | Atochem | Telomeres acryliques fluores et leur application au traitement hydrofuge et oleofuge de substrats divers. |
| DE69129371D1 (de) | 1990-10-03 | 1998-06-10 | Commw Scient Ind Res Org | Epoxydharzen auf der basis von makrocyclischen verbindungen |
| US6048952A (en) | 1991-07-10 | 2000-04-11 | 3M Innovative Properties Company | Perfluoroalkyl halides and derivatives |
| FR2683535B1 (fr) * | 1991-11-12 | 1994-10-28 | Atochem | Nouveaux copolymeres fluores et leur utilisation pour le revetement et l'impregnation de substrats divers. |
| DE4223111A1 (de) | 1992-07-14 | 1994-01-20 | Henkel Kgaa | Neue Lederfettungsmittel und ihre Verwendung |
| DE4416415A1 (de) | 1994-05-10 | 1995-11-16 | Hoechst Ag | Copolymere auf Basis von ethylenisch ungesättigten Dicarbonsäureanhydriden, langkettigen Olefinen und Fluorolefinen |
| FR2722791B1 (fr) * | 1994-07-22 | 1996-09-06 | Atochem Elf Sa | Procede de fabrication d'emulsions aqueuses de copolymeres fluores |
| US5725789A (en) | 1995-03-31 | 1998-03-10 | Minnesota Mining And Manufacturing Company | Aqueous oil and water repellent compositions |
| JP3277092B2 (ja) * | 1995-04-05 | 2002-04-22 | アヴェンティス・リサーチ・ウント・テクノロジーズ・ゲーエムベーハー・ウント・コー・カーゲー | 有機ガス検知用ポリマーフィルム |
| US6294103B1 (en) | 1996-11-07 | 2001-09-25 | 3M Innovative Properties Company | Use of amphiphilic copolymers containing a fluorinated monomer to impart waterproofness to leather |
| US8653213B2 (en) * | 1997-02-03 | 2014-02-18 | Cytonix, Llc | Hydrophobic coating compositions and articles coated with said compositions |
| US6380336B1 (en) * | 1998-03-24 | 2002-04-30 | Nano-Tex, Llc | Copolymers and oil-and water-repellent compositions containing them |
| FR2785904B1 (fr) | 1998-11-13 | 2000-12-15 | Atochem Elf Sa | Polymeres fluores par polymerisation en miniemulsion |
| US6353051B1 (en) * | 1999-03-10 | 2002-03-05 | E. I. Du Pont De Nemours And Company | Top coating for synthetic leathers |
| US7049379B2 (en) * | 1999-05-11 | 2006-05-23 | 3M Innovative Properties Company | Alkylated fluorochemical oligomers and use thereof in the treatment of fibrous substrates |
| EP1201815B1 (en) * | 2000-10-31 | 2006-04-26 | Asahi Glass Co., Ltd. | Water repellent composition |
| KR100889714B1 (ko) * | 2001-04-13 | 2009-03-23 | 아사히 가라스 가부시키가이샤 | 발수발유제 조성물 |
| JP2003221406A (ja) * | 2002-01-31 | 2003-08-05 | Asahi Glass Co Ltd | 水性分散液 |
| US7078454B2 (en) * | 2002-04-17 | 2006-07-18 | 3M Innovative Properties Company | Repellent fluorochemical compositions |
| JP4483582B2 (ja) * | 2002-10-15 | 2010-06-16 | 旭硝子株式会社 | 撥水撥油剤組成物 |
| 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 |
| EP1493761A1 (en) | 2003-07-02 | 2005-01-05 | 3M Innovative Properties Company | Fluoropolymer of fluorinated short chain acrylates or methacrylates and oil- and water repellent compositions based thereon |
| US7196133B2 (en) * | 2003-07-08 | 2007-03-27 | Kyoeisha Chemical Co., Ltd. | Surface tension control agent for coating material and coating material containing same |
| JP2007525604A (ja) * | 2004-02-04 | 2007-09-06 | ダウ・コーニング・コーポレイション | シリコーン樹脂を含有するエマルジョンによる織物の処理 |
| WO2008089391A1 (en) * | 2007-01-19 | 2008-07-24 | 3M Innovative Properties Company | Fluorinated surfactants and methods of using the same |
| DE602007003186D1 (de) | 2007-03-21 | 2009-12-24 | Du Pont | Fluorobetain-copolymer und Löschschaumkonzentrate daraus |
| US7829477B2 (en) * | 2007-10-29 | 2010-11-09 | E.I. Dupont De Nemours And Company | Fluorinated water soluble copolymers |
-
2007
- 2007-10-05 EP EP07117935A patent/EP2045276A1/en not_active Withdrawn
-
2008
- 2008-09-30 US US12/679,039 patent/US9029471B2/en not_active Expired - Fee Related
- 2008-09-30 JP JP2010528083A patent/JP5671342B2/ja not_active Expired - Fee Related
- 2008-09-30 CN CN200880109938A patent/CN101815796A/zh active Pending
- 2008-09-30 AU AU2008308832A patent/AU2008308832B2/en not_active Ceased
- 2008-09-30 KR KR1020107009893A patent/KR20100072065A/ko not_active Abandoned
- 2008-09-30 CA CA2700142A patent/CA2700142C/en not_active Expired - Fee Related
- 2008-09-30 NZ NZ583941A patent/NZ583941A/en not_active IP Right Cessation
- 2008-09-30 KR KR1020157034171A patent/KR20150140866A/ko not_active Ceased
- 2008-09-30 WO PCT/US2008/078289 patent/WO2009046016A1/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| US20100288962A1 (en) | 2010-11-18 |
| US9029471B2 (en) | 2015-05-12 |
| JP2011511848A (ja) | 2011-04-14 |
| EP2045276A1 (en) | 2009-04-08 |
| AU2008308832B2 (en) | 2013-08-15 |
| CA2700142A1 (en) | 2009-04-09 |
| CA2700142C (en) | 2015-03-31 |
| KR20100072065A (ko) | 2010-06-29 |
| CN101815796A (zh) | 2010-08-25 |
| WO2009046016A1 (en) | 2009-04-09 |
| JP5671342B2 (ja) | 2015-02-18 |
| KR20150140866A (ko) | 2015-12-16 |
| AU2008308832A1 (en) | 2009-04-09 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PSEA | Patent sealed | ||
| RENW | Renewal (renewal fees accepted) | ||
| RENW | Renewal (renewal fees accepted) |
Free format text: PATENT RENEWED FOR 1 YEAR UNTIL 30 SEP 2016 BY CPA GLOBAL Effective date: 20150815 |
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| LAPS | Patent lapsed |